Luteolin

  • GreenMolBD CID : 368
  • Molecular Formula : C15H10O6
  • Molecular Weight : 286.239
  • Exact Molecular Mass : 286.048
  • IUPAC Name : 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
  • InChI : InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
  • InChI Key : IQPNAANSBPBGFQ-UHFFFAOYSA-N
  • Canonical SMILES : C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
  • Isomeric SMILES : c1cc(c(cc1c2cc(=O)c3c(cc(cc3o2)O)O)O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

1.2. Taxonomy Tree

1.3. Alternative Parent

3'-hydroxyflavonoids; 4'-hydroxyflavonoids; 5-hydroxyflavonoids; 7-hydroxyflavonoids; Chromones; Catechols; 1-hydroxy-2-unsubstituted benzenoids; Pyranones and derivatives; 1-hydroxy-4-unsubstituted benzenoids; Benzene and substituted derivatives; Heteroaromatic compounds; Vinylogous acids; Oxacyclic compounds; Hydrocarbon derivatives; Organooxygen compounds; Organic oxides;

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

3'-hydroxyflavonoid; 4'-hydroxyflavonoid; 5-hydroxyflavonoid; 7-hydroxyflavonoid; Flavone; Hydroxyflavonoid; Chromone; Benzopyran; 1-benzopyran; Catechol; 1-hydroxy-4-unsubstituted benzenoid; 1-hydroxy-2-unsubstituted benzenoid; Phenol; Pyranone; Monocyclic benzene moiety; Pyran; Benzenoid; Vinylogous acid; Heteroaromatic compound; Organoheterocyclic compound; Oxacycle; Organooxygen compound; Hydrocarbon derivative; Organic oxygen compound; Organic oxide; Aromatic heteropolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
2.1252 107.22 4 6 21 1 12 12 7.24787 343.263 251.186 0.833878

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-179.411055 2.48 -4.77 -8.8533 -0.68705 4.083

4. Compound Reactivity

DLP nRFG nLMR
0 0 4

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Toxic 0.77039 1387.9 0.114167 None Strong Mild Non-Degradable 0.00899037 5.4543

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes Yes Yes Yes No Yes

7. Synonyms

Name
luteolin
491-70-3
3',4',5,7-Tetrahydroxyflavone
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Digitoflavone
Luteolol
Flacitran
Luteoline
Weld Lake
Cyanidenon 1470
Salifazide
5,7,3',4'-Tetrahydroxyflavone
Yama kariyasu
C.I. Natural Yellow 2
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
7-Tetrahydroxyflavone
CCRIS 3790
EINECS 207-741-0
CHEMBL151
BRN 0292084
2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone
C.I. 75590
FLAVONE, 3',4',5,7-TETRAHYDROXY-
CHEBI:15864
IQPNAANSBPBGFQ-UHFFFAOYSA-N
IN1269
MFCD00017309
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one
AK-73099
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
3&prime
,4&prime
,5,7-Tetrahydroxyflavone
Q-100551
SMR000326896
UNII-KUX1ZNC9J2
B-Lactams
4dew
4dgn
4hkn
2-?(3,?4-?DIHYDROXYPHENYL)-?5,?7-?DIHYDROXY-?4H-?1-?BENZOPYRAN-?4-?ONE
LU2
Prestwick_122
PubChem18249
AC1NQX1A
Prestwick0_000870
Prestwick1_000870
Prestwick2_000870
Prestwick3_000870
KUX1ZNC9J2
ACMC-209kf3
D01OBV
D04AIT
BIDD:PXR0059
Lopac0_000660
Oprea1_849964
SCHEMBL20426
BSPBio_000919
Luteolin, analytical standard
MLS000697655
MLS000860038
MLS002154043
MLS006011917
BIDD:ER0122
SPBio_002840
BDBM7459
BPBio1_001011
GTPL5215
MEGxp0_000143
DTXSID4074988
ACon1_000223
cid_5280445
CTK8B1741
KS-00000MHI
AOB5669
MolPort-000-706-683
BB_NC-1244
HMS1570N21
HMS2097N21
HMS2220C06
HMS3356L02
HMS3561N09
HMS3649N21
HMS3656A05
Luteolin, >=99.0% (TLC)
HY-N0162
TNP00073
Luteolin, >=98% (TLC), powder
ANW-30733
BBL027837
BS0245
CL0029
GP5376
LMPK12110006
s2320
SBB066117
STK801923
ZINC18185774
AKOS002140588
AC-1125
BCP9000865
CCG-208309
CS-4611
KS-5202
MCULE-6874646775
RTR-017772
SMP2_000042
NCGC00016467-01
NCGC00016467-02
NCGC00016467-03
NCGC00016467-04
NCGC00016467-05
NCGC00016467-06
NCGC00016467-07
NCGC00142375-01
NCGC00142375-02
NCGC00142375-03
NCGC00179375-01
NCGC00179375-02
4CN-0710
AJ-70437
AN-15217
BC208070
BR-73099
BT000417
CAS-491-70-3
CJ-15855
HE020496
HE280300
HE345267
HE345268
HE375519
HE375520
LS-69039
SC-17258
ST024703
BCP0726000198
AB0010480
AX8006331
KB-221427
ST2416056
FT-0600053
N1831
91L703
C01514
J10229
L 9283
S-1623
S00110
Luteolin, primary pharmaceutical reference standard
I06-0436
BRD-K05236810-001-05-9
23A002A4-B47B-46CD-848C-65042EACF3FF
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyrone-4-one
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one #
4H-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- (9CI)
PHENOXY, 4-[5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-2-YL]-2-HYDROXY-
PHENOXY, 5-[5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-2-YL]-2-HYDROXY-
Leutolin
SR-01000779333
HMS3714N21
BG00623695
BG01578502
SR-01000779333-4
SR-01000779333-5
SR-01000779333-7
1318-21-4

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Luteolin
Abrus precatorius L. Seed 5
Abutilon indicum (L.) Sw. Flower 7
Andrographis paniculata Aerial 2 , 30
Areca catechu L. Nut; Fruit 2 , 13 , 14
Argemone maxicana L. Seed 3
Coix lachryma Linn. Seed 2
Coriandrum sativum Linn. Grass 9
Cuscuta reflexa 5
Cyperus rotundus L Rhizome 19 , 3
Hygrophila auriculata 4 , 2
Ichnocarpus frutescens Leaf 8
Ipomoea aquatica Whole Plant 11 , 12
Ixora coccinea L.  Aerial 6 , 8
Ludwigia octovalvis 1
Ricinus communis 4
Scoparia dulcia L Aerial; Whole Plant 2 , 16
Tamarindus indica Pericarp and Seed 6 , 7

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
165 15-hydroxyprostaglandin dehydrogenase HPGD Homo sapiens 11.2202 894
218 1-deoxy-D-xylulose 5-phosphate reductoisomerase Escherichia coli 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 3.40E+3 10.1016/j.bioorg.2015.02.008 25800132
219 3-oxoacyl-acyl-carrier protein reductase Plasmodium falciparum 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 4000 10.1021/jm0600545 16722653
219 3-oxoacyl-acyl-carrier protein reductase Plasmodium falciparum 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 1800 10.1021/jm0600545 16722653
219 3-oxoacyl-acyl-carrier protein reductase Plasmodium falciparum 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 800 10.1021/jm0600545 16722653
166 5-lipoxygenase/FLAP Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 1600 10.1016/j.ejmech.2013.11.030 24368208
1 Acetylcholinesterase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 65800 10.1016/j.ejmech.2009.09.041 19879672
33 acetylcholinesterase (Cartwright blood group) ACHE Homo sapiens 65.8 441660
192 adenosine A1 receptor Adora1 Rattus norvegicus 1.55 379300
192 adenosine A1 receptor Adora1 Rattus norvegicus 1.66 379299
193 Adenosine receptor Rattus norvegicus 1660 10757709
193 Adenosine receptor Rattus norvegicus 1550 10757709
69 aldehyde dehydrogenase 1 family member A1 ALDH1A1 Homo sapiens 8.9125 1030
69 aldehyde dehydrogenase 1 family member A1 ALDH1A1 Homo sapiens 19.9526 1030
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 0.6 760685
2 aldo-keto reductase family 1 member B Akr1b1 Rattus norvegicus 1.54 385353
477 aldo-keto reductase family 1, member B1 (aldose reductase) AKR1B1 Bos taurus 0.754 760688
477 aldo-keto reductase family 1, member B1 (aldose reductase) AKR1B1 Bos taurus 9.57 34338
160 Aldose reductase Rattus norvegicus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 1540 10.1021/np070489a 18298080
478 Aldose reductase (ALR2) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 9570 10.1021/jm980441h 10354396
478 Aldose reductase (ALR2) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 754 10.1016/j.bmc.2013.04.066 23683835
167 Aldose reductase (AR) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 600 10.1016/j.bmc.2013.04.066 23683835
225 alpha-Amylase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 18400 10.1021/jm800115x 18507367
479 angiotensin I converting enzyme ACE Oryctolagus cuniculus 290 464081
479 angiotensin I converting enzyme ACE Oryctolagus cuniculus 290 612411
429 Angiotensin-converting enzyme Oryctolagus cuniculus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 290000 10.1016/j.bmcl.2010.01.113 20167484
429 Angiotensin-converting enzyme Oryctolagus cuniculus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 290000 10.1016/j.bmc.2011.06.085 21782455
117 ankyrin-like protein B18R Vaccinia virus 8.9125 720579
117 ankyrin-like protein B18R Vaccinia virus 11.2202 720580
59 arachidonate 12-lipoxygenase, 12S type ALOX12 Homo sapiens 2.5119 1452
59 arachidonate 12-lipoxygenase, 12S type ALOX12 Homo sapiens 15.8489 1452
93 arachidonate 15-lipoxygenase ALOX15 Homo sapiens 1.5849 887
93 arachidonate 15-lipoxygenase ALOX15 Homo sapiens 2.5119 887
232 arachidonate 15-lipoxygenase, type B ALOX15B Homo sapiens 10 881
232 arachidonate 15-lipoxygenase, type B ALOX15B Homo sapiens 15.8489 881
168 arachidonate 5-lipoxygenase ALOX5 Homo sapiens 1.6 1063904
118 ataxin 2 ATXN2 Homo sapiens 11.2202 651635
118 ataxin 2 ATXN2 Homo sapiens 19.9526 651635
480 ATP binding cassette subfamily B member 1 ABCB1 Homo sapiens 19.6 681162
190 ATPase family, AAA domain containing 5 ATAD5 Homo sapiens 7.3048 504466
190 ATPase family, AAA domain containing 5 ATAD5 Homo sapiens 9.1962 504467
481 ATP-binding cassette sub-family G member 2 Homo sapiens 8900 10.1021/np100797y 21275386
6 ATP-dependent phosphofructokinase Tb927.3.3270 Trypanosoma brucei brucei TREU927 10.691 485367
6 ATP-dependent phosphofructokinase Tb927.3.3270 Trypanosoma brucei brucei TREU927 13.4591 504636
6 ATP-dependent phosphofructokinase Tb927.3.3270 Trypanosoma brucei brucei TREU927 23.9341 504637
482 Beta amyloid A4 protein Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 6400 10.1016/j.bmcl.2014.05.008 24878198
236 BLM RecQ like helicase BLM Homo sapiens 3.8273 720503
236 BLM RecQ like helicase BLM Homo sapiens 15.8489 2528
236 BLM RecQ like helicase BLM Homo sapiens 19.9526 2528
236 BLM RecQ like helicase BLM Homo sapiens 35.4813 2528
483 BRCA1, DNA repair associated BRCA1 Homo sapiens 35.4813 624202
119 bromodomain adjacent to zinc finger domain 2B BAZ2B Homo sapiens 79.4328 504333
36 Butyrylcholine esterase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 166100 10.1016/j.ejmech.2009.09.041 19879672
37 butyrylcholinesterase BCHE Homo sapiens 166.1 441659
431 Carbonic anhydrase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 293 26498393
7 carbonic anhydrase 1 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 2200 10.3109/14756366.2011.643303 22168126
7 carbonic anhydrase 1 CA1 Homo sapiens 10 1254155
8 carbonic anhydrase 12 CA12 Homo sapiens 0.0603 1254159
9 carbonic anhydrase 2 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 740 10.3109/14756366.2011.643303 22168126
9 carbonic anhydrase 2 CA2 Homo sapiens 3.6916 1254156
484 Carbonic anhydrase 3 (CA III) 5400 10.3109/14756366.2011.643303 22168126
10 carbonic anhydrase 4 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 4400 10.3109/14756366.2011.643303 22168126
10 carbonic anhydrase 4 CA4 Homo sapiens 0.293 1254162
130 carbonic anhydrase 7 CA7 Homo sapiens 0.0047 1254158
99 Carbonic Anhydrase I Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU >10000 26498393
100 Carbonic Anhydrase II Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 3692 26498393
133 Carbonic Anhydrase VII Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 4.7 26498393
134 Carbonic Anhydrase XII Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 60 26498393
238 cationic trypsin LOC780933 Bos taurus 35.3 214874
239 CD38 molecule CD38 Homo sapiens 8.2 603318
240 Cell division protein kinase 5 Rattus norvegicus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU >250000 10.1021/np034011s 15043421
485 Cruzipain Trypanosoma cruzi 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 155700 10.1021/jm301749y 23437772
485 Cruzipain Trypanosoma cruzi 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 27300 10.1021/jm301749y 23437772
486 cyclin dependent kinase 6 CDK6 Homo sapiens 300 242481
486 cyclin dependent kinase 6 CDK6 Homo sapiens 300 1095229
487 Cyclin-Dependent Kinase 1 (CDK1) Marthasterias glacialis 6200 10.1021/jm049353p 15689157
488 Cyclin-dependent kinase 2 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 20000 10.1016/j.bmcl.2006.12.011 17178224
241 cyclin-dependent kinase 5 Cdk5 Rattus norvegicus 250 400266
489 Cyclin-Dependent Kinase 5 (CDK5) Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 3800 10.1021/jm049353p 15689157
490 Cyclin-Dependent Kinase 6 (CDK6) Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU >300000 10.1021/jm049353p 15689157
112 Cyclooxygenase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 2.5 12444669
112 Cyclooxygenase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 <100 12444669
491 cystic fibrosis transmembrane conductance regulator CFTR Homo sapiens 29.27 743267
242 Cytochrome P450 1A1 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 1249 10.1016/j.bmc.2010.07.020 20696580
242 Cytochrome P450 1A1 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 890 10.1016/j.bmc.2011.03.042 21482471
107 Cytochrome P450 1A2 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 3370 10.1016/j.bmc.2010.07.020 20696580
243 Cytochrome P450 1B1 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 79 10.1016/j.bmc.2010.07.020 20696580
243 Cytochrome P450 1B1 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 56 10.1016/j.bmc.2011.03.042 21482471
492 cytochrome P450 family 1 subfamily A member 1 CYP1A1 Homo sapiens 1.249 502474
108 cytochrome P450 family 1 subfamily A member 2 CYP1A2 Homo sapiens 3.37 502473
493 cytochrome P450 family 1 subfamily B member 1 CYP1B1 Homo sapiens 0.079 502475
244 cytochrome P450 family 2 subfamily C member 19 CYP2C19 Homo sapiens 15.8489 899
245 cytochrome P450 family 2 subfamily C member 9 CYP2C9 Homo sapiens 31.6228 883
158 cytochrome P450 family 2 subfamily D member 6 CYP2D6 Homo sapiens 31.6228 891
114 cytochrome P450 family 3 subfamily A member 4 CYP3A4 Homo sapiens 5.0119 884
114 cytochrome P450 family 3 subfamily A member 4 CYP3A4 Homo sapiens 5.0119 885
114 cytochrome P450 family 3 subfamily A member 4 CYP3A4 Homo sapiens 15.8489 884
114 cytochrome P450 family 3 subfamily A member 4 CYP3A4 Homo sapiens 15.8489 885
494 Cytosol aminopeptidase Sus scrofa 49600 10.1021/np50120a001
246 death associated protein kinase 1 DAPK1 Homo sapiens 21 1247840
247 Death-associated protein kinase 1 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 21000 26322379
495 Dipeptidyl peptidase III Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 2.20E+4 27754592
11 DNA polymerase beta POLB Homo sapiens 7.0795 485314
249 DNA polymerase eta POLH Homo sapiens 3.1623 588591
65 DNA polymerase iota POLI Homo sapiens 3.9811 588590
65 DNA polymerase iota POLI Homo sapiens 56.2341 588590
197 DNA polymerase kappa POLK Homo sapiens 0.2668 588579
197 DNA polymerase kappa POLK Homo sapiens 0.8913 588579
197 DNA polymerase kappa POLK Homo sapiens 1.5003 588579
197 DNA polymerase kappa POLK Homo sapiens 6.3096 588579
197 DNA polymerase kappa POLK Homo sapiens 14.1254 588579
496 DNA topoisomerase 1 Rattus norvegicus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 660 10.1016/j.bmcl.2010.03.063 20371180
496 DNA topoisomerase 1 Rattus norvegicus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 5000 10.1016/j.bmcl.2010.03.063 20371180
210 DNA topoisomerase I Top1 Rattus norvegicus 0.66 481004
210 DNA topoisomerase I Top1 Rattus norvegicus 5 481006
497 Dopamine Transporter (DAT) Rattus norvegicus 1450 10.1016/j.bmc.2010.09.049 20971650
498 Enoyl-ACP Reductase (FabI) Escherichia coli 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 7050 10.1016/j.bmcl.2009.11.042 19959361
253 Enoyl-acyl-carrier protein reductase Plasmodium falciparum 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 2000 10.1021/jm0600545 16722653
253 Enoyl-acyl-carrier protein reductase Plasmodium falciparum 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 2100 10.1021/jm0600545 16722653
254 Fatty acid synthase 6.25E+4
254 Fatty acid synthase Plasmodium falciparum 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 5000 10.1021/jm0600545 16722653
254 Fatty acid synthase Plasmodium falciparum 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 11500 10.1021/jm0600545 16722653
254 Fatty acid synthase FASN Homo sapiens 62.5 270726
499 Fatty acid synthase (FAS) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 62500 10.1016/j.bmcl.2006.07.018 16870425
256 flap structure-specific endonuclease 1 FEN1 Homo sapiens 11.2202 588795
256 flap structure-specific endonuclease 1 FEN1 Homo sapiens 15.8489 588795
13 fms related tyrosine kinase 3 FLT3 Homo sapiens 0.83 730328
258 G protein-coupled receptor 35 GPR35 Homo sapiens 3.2 663956
258 G protein-coupled receptor 35 GPR35 Homo sapiens 7.24 663955
258 G protein-coupled receptor 35 GPR35 Homo sapiens 18.6 663960
500 galactokinase 1 GALK1 Homo sapiens 47.269 2015
164 galactosidase alpha GLA Homo sapiens 50.1187 2107
84 geminin, DNA replication inhibitor GMNN Homo sapiens 0.0184 624297
84 geminin, DNA replication inhibitor GMNN Homo sapiens 3.6626 624296
14 glucosidase alpha, acid GAA Homo sapiens 25.1189 2100
73 glucosylceramidase beta GBA Homo sapiens 12.5893 2101
73 glucosylceramidase beta GBA Homo sapiens 28.1838 2101
43 glutaminase GLS Homo sapiens 35.4813 624170
15 glycogen synthase kinase 3 beta GSK3B Homo sapiens 1.5 1115335
15 glycogen synthase kinase 3 beta GSK3B Homo sapiens 3.812 434954
128 Glycogen Synthase Kinase-3, beta Rattus norvegicus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 800 10.1021/jm049353p 15689157
128 Glycogen Synthase Kinase-3, beta Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 3812 434954
260 Glyoxalase I Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 7700 10.1016/j.bmc.2008.01.031 18258440
260 Glyoxalase I GLO1 Homo sapiens 7.7 381802
261 G-protein coupled receptor 35 Homo sapiens 7240 10.1021/ml2003058
261 G-protein coupled receptor 35 Homo sapiens 3200 10.1021/ml2003058
261 G-protein coupled receptor 35 Homo sapiens 18600 10.1021/ml2003058
501 Human diphtheria toxin-like ADP-ribosyltransferase (ARTD5 or PARP5a) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 2400 10.1021/jm3018783 23574272
502 Human diphtheria toxin-like ADP-ribosyltransferase (ARTD6 or PARP5b) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 1100 10.1021/jm3018783 23574272
265 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 32900 7699704
265 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 450 10.1016/j.bmc.2014.04.016 24794743
265 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 >20000 10.1016/j.bmc.2014.04.016 24794743
265 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 8900 10.1016/j.bmc.2014.04.016 24794743
265 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 25000 7699704
82 hypoxia inducible factor 1 subunit alpha HIF1A Homo sapiens 0.3981 914
82 hypoxia inducible factor 1 subunit alpha HIF1A Homo sapiens 0.3981 915
90 karyopherin subunit beta 1 KPNB1 Homo sapiens 44.6684 540263
90 karyopherin subunit beta 1 KPNB1 Homo sapiens 50.1187 540253
28 lamin A/C LMNA Homo sapiens 3.1623 1487
503 large T antigen Simian virus 40 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 47930 2102
503 large T antigen SV40gp6 Macaca mulatta polyomavirus 1 11.9 1903
503 large T antigen SV40gp6 Macaca mulatta polyomavirus 1 47.93 2102
504 Lck Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 1 10.1021/np50089a001
268 lens epithelium-derived growth factor p75 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 14730 1053171
268 lens epithelium-derived growth factor p75 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 1059 1053172
204 lipoxygenase LOX1.1 Glycine max 3.2 254906
204 lipoxygenase LOX1.1 Glycine max 3.2 261407
204 lipoxygenase LOX1.1 Glycine max 121.7 1063896
204 lipoxygenase LOX1.1 Glycine max 148.5 1063898
204 lipoxygenase LOX1.1 Glycine max 189.6 1063900
205 Lipoxygenase-1 Glycine max 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 3200 10.1021/jm0510474 16509583
205 Lipoxygenase-1 Glycine max 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 3200 10.1016/j.bmcl.2005.07.036 16143531
205 Lipoxygenase-1 Glycine max 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 121700 10.1016/j.ejmech.2013.11.030 24368208
269 Lymphocyte differentiation antigen CD38 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 8200 10.1016/j.bmcl.2011.05.022 21641214
115 lysine methyltransferase 2A KMT2A Homo sapiens 12.5893 1766
115 lysine methyltransferase 2A KMT2A Homo sapiens 14.1254 1768
115 lysine methyltransferase 2A KMT2A Homo sapiens 19.9526 1768
115 lysine methyltransferase 2A KMT2A Homo sapiens 31.6228 1768
115 lysine methyltransferase 2A KMT2A Homo sapiens 35.4813 1766
271 Lysyl-tRNA synthetase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 4500 10.1021/jm201271b 22257213
271 Lysyl-tRNA synthetase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 12000 10.1021/jm201271b 22257213
505 M1-family alanyl aminopeptidase MAL13P1.56 Plasmodium falciparum 3D7 22.86 1445
506 matrix metallopeptidase 12 MMP12 Homo sapiens 0.98 670314
507 matrix metallopeptidase 13 MMP13 Homo sapiens 10.05 670315
348 matrix metallopeptidase 2 MMP2 Homo sapiens 3.61 670311
508 matrix metallopeptidase 3 MMP3 Homo sapiens 16.2 670312
509 matrix metallopeptidase 9 MMP9 Homo sapiens 5.62 670313
272 Matrix metalloproteinase-1 (cd-MMP-1) 3.03E+3
510 Matrix metalloproteinase-12 (MMP12) Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 980 10.1016/j.bmc.2012.04.063 22658537
511 Matrix Metalloproteinase-13 (MMP-13) Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 10050 10.1016/j.bmc.2012.04.063 22658537
349 Matrix metalloproteinase-2 (MMP-2) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 3610 10.1016/j.bmc.2012.04.063 22658537
304 Matrix metalloproteinase-3 (MMP3) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 16200 10.1016/j.bmc.2012.04.063 22658537
512 Matrix metalloproteinase-9 (MMP-9) Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 5620 10.1016/j.bmc.2012.04.063 22658537
116 menin 1 MEN1 Homo sapiens 12.5893 1766
116 menin 1 MEN1 Homo sapiens 14.1254 1768
116 menin 1 MEN1 Homo sapiens 19.9526 1768
116 menin 1 MEN1 Homo sapiens 31.6228 1768
116 menin 1 MEN1 Homo sapiens 35.4813 1766
16 microtubule associated protein tau MAPT Homo sapiens 12.5893 1460
274 Mitogen-activated protein kinase 10 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 2.30E+3 10.1002/cbic.201000487 21108268
275 Mitogen-activated protein kinase 14 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 1.80E+4 10.1002/cbic.201000487 21108268
211 Monoamine oxidase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 4900 10.1016/j.bmc.2009.12.029 20045650
211 Monoamine oxidase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 59700 10.1016/j.bmc.2009.12.029 20045650
17 muscleblind like splicing regulator 1 MBNL1 Homo sapiens 17.7828 2675
513 NADPH oxidase 4 Homo sapiens 850 10.1021/jm1004368 20731357
279 neuraminidase 2 NEU2 Homo sapiens 130 466938
30 nuclear factor, erythroid 2 like 2 NFE2L2 Homo sapiens 20.5962 504444
280 PC4 and SFRS1 interacting protein 1 PSIP1 Homo sapiens 1.059 1053172
280 PC4 and SFRS1 interacting protein 1 PSIP1 Homo sapiens 14.73 1053171
180 peptidylprolyl cis/trans isomerase, NIMA-interacting 1 PIN1 Homo sapiens 63.0957 504891
72 peroxisome proliferator activated receptor gamma Pparg Mus musculus 2.3 1180479
372 Peroxisome proliferator-activated receptor gamma Mus musculus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 2300 10.1021/np500150f 24955889
514 P-glycoprotein 1 (Pgp/MDR1) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 19600 10.1016/j.bbrc.2004.06.020 15240100
282 phosphoglycerate kinase PGKC Trypanosoma brucei brucei TREU927 28.1838 602233
284 PIM-1 Kinase (PIM1) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 1600 10.1158/1535-7163.MCT-06-0397 17218638
374 plasminogen Plg Mus musculus 7.9433 540303
375 plasminogen activator, urokinase Plau Mus musculus 7.9433 540303
376 plasminogen activator, urokinase receptor Plaur Mus musculus 7.9433 540303
515 poly(ADP-ribose) polymerase 1 PARP1 Homo sapiens 4.2658 735783
516 poly-ADP-ribose polymerase 1 (PARP1) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 4200 10.1021/jm3018783 23574272
517 POsterior Segregation pos-1 Caenorhabditis elegans 60.374 1964
518 POsterior Segregation family member (pos-1) Caenorhabditis elegans 60374 1964
181 RAN, member RAS oncogene family RAN Homo sapiens 50.1187 540253
185 Rap guanine nucleotide exchange factor 3 RAPGEF3 Homo sapiens 44.6684 720709
50 RAR-related orphan receptor gamma Rorc Mus musculus 11.2202 2546
50 RAR-related orphan receptor gamma Rorc Mus musculus 14.1254 2551
50 RAR-related orphan receptor gamma Rorc Mus musculus 17.7828 2546
50 RAR-related orphan receptor gamma Rorc Mus musculus 22.3872 2551
50 RAR-related orphan receptor gamma Rorc Mus musculus 35.4813 2546
50 RAR-related orphan receptor gamma Rorc Mus musculus 35.4813 2551
289 Receptor-type tyrosine-protein kinase FLT3 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 830 10.1016/j.bmcl.2013.01.049 23411073
519 RecName: Full=Zinc finger protein mex-5 Caenorhabditis elegans 31000 1960
20 Serine/threonine-protein kinase Aurora-B Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 3.88E+3 10.1111/cbdd.12445 25298094
294 Serine/threonine-protein kinase PIM 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 1585 10.1016/j.bmc.2007.06.025 17637507
520 Sialidase Clostridium perfringens 4300 10.1016/j.bmc.2009.08.036 19729316
295 Sialidase 2 Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 130000 10.1016/j.bmc.2009.12.062 20097567
66 SMAD family member 3 SMAD3 Homo sapiens 11.2202 588855
91 snurportin 1 SNUPN Homo sapiens 44.6684 540263
91 snurportin 1 SNUPN Homo sapiens 50.1187 540253
521 solute carrier family 6 member 3 Slc6a3 Rattus norvegicus 1.45 536224
297 spleen associated tyrosine kinase SYK Homo sapiens 4.5 701064
297 spleen associated tyrosine kinase SYK Homo sapiens 12 701071
453 survival of motor neuron 2, centromeric SMN2 Homo sapiens 8.9125 1458
522 tankyrase TNKS Homo sapiens 2.39883 735786
523 tankyrase 2 TNKS2 Homo sapiens 1.07152 735784
47 thyroid hormone receptor beta THRB Homo sapiens 44.6684 1479
32 thyroid stimulating hormone receptor TSHR Homo sapiens 39.8107 926
524 transthyretin TTR Homo sapiens 0.07 1239060
524 transthyretin TTR Homo sapiens 7 1239061
525 Transthyretin (TTR) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 7000 26214366
525 Transthyretin (TTR) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 70 26214366
209 Trypsin Bos taurus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU,5II2 35300 10.1021/jm970245v 9406602
81 tumor protein p53 TP53 Homo sapiens 3.1623 902
81 tumor protein p53 TP53 Homo sapiens 5.0119 924
81 tumor protein p53 TP53 Homo sapiens 12.5893 924
81 tumor protein p53 TP53 Homo sapiens 28.1838 504706
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 29.0929 686978
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 29.0929 686979
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 33.4983 686978
126 ubiquitin specific peptidase 1 USP1 Homo sapiens 35.4813 504865
126 ubiquitin specific peptidase 1 USP1 Homo sapiens 44.6684 743255
301 Werner syndrome RecQ like helicase WRN Homo sapiens 3.0402 720497
526 xanthine dehydrogenase XDH Bos taurus 1.9 424726
526 xanthine dehydrogenase XDH Homo sapiens 2.9 1183551
526 xanthine dehydrogenase XDH Homo sapiens 7.8 1238319
527 Xanthine dehydrogenase/oxidase (XO) Bos taurus 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 1900 10.1021/np8007123 19388706
302 Xanthine oxidase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 2900 10.1016/j.ejmech.2014.07.013 25019478
302 Xanthine oxidase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 7.8 26096677
302 Xanthine oxidase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 11540 10.1021/np800643n 19476336
302 Xanthine oxidase Homo sapiens 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 550 10.1021/np970237h 9461655
528 Zinc aminopeptidase Plasmodium falciparum (isolate FcB1 / Columbia) 3SZ1,4DEW,4DGN,4HKN,4QXV,4QYA,5AUU 22860 1445
529 Zinc finger protein mex-5 mex-5 Caenorhabditis elegans 31 1960

10. Chemical Vendors

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