7-Hydroxy-6-methoxychromen-2-one

  • GreenMolBD CID : 130
  • Molecular Formula : C10H8O4
  • Molecular Weight : 192.17
  • Exact Molecular Mass : 192.042
  • IUPAC Name : 7-hydroxy-6-methoxychromen-2-one
  • InChI : InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3
  • InChI Key : RODXRVNMMDRFIK-UHFFFAOYSA-N
  • Canonical SMILES : COC1=C(C=C2C(=C1)C=CC(=O)O2)O
  • Isomeric SMILES : COc1cc2ccc(=O)oc2cc1O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

1.2. Taxonomy Tree

1.3. Alternative Parent

1-benzopyrans; Anisoles; Pyranones and derivatives; Alkyl aryl ethers; 1-hydroxy-2-unsubstituted benzenoids; Heteroaromatic compounds; Lactones; Oxacyclic compounds; Organic oxides; Hydrocarbon derivatives;

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

7-hydroxycoumarin; Benzopyran; 1-benzopyran; Anisole; 1-hydroxy-2-unsubstituted benzenoid; Alkyl aryl ether; Pyranone; Pyran; Benzenoid; Heteroaromatic compound; Lactone; Oxacycle; Ether; Organoheterocyclic compound; Organic oxygen compound; Organooxygen compound; Hydrocarbon derivative; Organic oxide; Aromatic heteropolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
1.333 55.76 1 4 14 1 6 6 4.93278 237.813 182.834 0.808073

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-119.389076 3.99 -4.871 -8.82102 -0.92115 3.95

4. Compound Reactivity

DLP nRFG nLMR
0 1 2

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)
Carcinogen Non-Mutagen Toxic 0.544609 13428.3 0.0337515 Mild None Mild Degradable 0.00530664 18.0165

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 Yes Yes

7. Synonyms

Name
scopoletin
92-61-5
Gelseminic acid
6-Methylesculetin
7-Hydroxy-6-methoxy-2H-chromen-2-one
Chrysatropic acid
Scopoletine
Murrayetin
Scopoletol
7-Hydroxy-6-methoxycoumarin
6-O-Methylesculetin
Escopoletin
6-Methoxy-7-hydroxycoumarin
7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one
6-Methoxyumbelliferone
2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy-
Esculetin 6-methyl ether
beta-Methylesculetin
Esculetin-6-methyl ether
.beta.-Methylesculetin
Buxuletin
COUMARIN, 7-HYDROXY-6-METHOXY-
NSC 405647
CCRIS 3592
7-hydroxy-6-methoxychromen-2-one
EINECS 202-171-9
NSC405647
BRN 0156296
CHEMBL71851
CHEBI:17488
RODXRVNMMDRFIK-UHFFFAOYSA-N
7-hydroxy-6-methoxy-chromen-2-one
TNP00096
MFCD00006872
NSC-405647
AK111291
S-2000
2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy- (9CI)
Chrysotropic Acid
Acid, Gelseminic
Acid, Chrysotropic
SMR000112541
UNII-KLF1HS0SXJ
Baogongteng B
b-Methylaesculetin
beta -methylesculetin
PubChem15777
Scopoletin, >=99%
KLF1HS0SXJ
Prestwick0_000962
Prestwick1_000962
Prestwick2_000962
Prestwick3_000962
Spectrum2_001207
Spectrum3_001532
Spectrum4_001054
Spectrum5_000654
Aesculetin 6-methyl ether
D05QOR
AC1NQX27
BIDD:PXR0125
BSPBio_000963
BSPBio_002944
KBioGR_001348
5-18-03-00203 (Beilstein Handbook Reference)
7-hydroxy-6-methoxy-coumarin
MLS002154074
MLS002472878
Bio-0208
DivK1c_000720
SCHEMBL147702
SPECTRUM1502242
7-hydroxy 6-methoxy coumarine
SPBio_000994
SPBio_002884
Scopoletin, analytical standard
BPBio1_001061
MEGxp0_001192
DTXSID0075368
ACon1_000143
HMS502D22
KBio1_000720
KBio3_002444
KS-00000YGS
ZINC57733
BIS1402
MolPort-000-707-493
NINDS_000720
ZX-AFC000681
HMS1571A05
HMS1921N16
HMS2098A05
HMS2268G04
ALBB-023369
HY-N0342
ZX-AN021883
ZX-AT021192
6-methoxy-7-oxidanyl-chromen-2-one
BDBM50156693
CCG-39140
TD8126
AKOS000277133
CS-5791
FCH1115349
MCULE-6077230919
OR22352
RTR-029034
CAS-92-61-5
IDI1_000720
7-hydroxy-6-methoxy-1-benzopyran-2-one
NCGC00016349-01
NCGC00016349-02
NCGC00016349-03
NCGC00016349-04
NCGC00016349-05
NCGC00016349-06
NCGC00016349-07
NCGC00016349-08
NCGC00094973-01
NCGC00094973-02
NCGC00094973-03
4CN-0905
AJ-09778
AN-42608
CC-34387
HE019424
HE416790
LS-55217
NCI60_003834
SC-90283
ST056287
ZB002243
7-Hydroxy-6-methoxy-2H-chromen-2-one #
AB0019688
AX8035441
KB-249948
TR-029034
AB00443525
FT-0631451
S0367
ST24045669
V0141
C01752
W-3522
006S872
A844290
C-30831
BRD-K96163925-001-06-5
I14-14171
0B4B9FAA-686D-4977-AA08-65F8E4F1977C
Scopoletin, United States Pharmacopeia (USP) Reference Standard
7-Hydroxy-5-methoxycoumarin
SR-01000841273
BG01509594
SR-01000841273-3
SR-01000841273-4

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
7-Hydroxy-6-methoxychromen-2-one
Abelmoschus esculentus (L.) Moench 6
Abutilon indicum (L.) Sw. Whole Plant 10
Apium graveolens Seed 3
Coriandrum sativum Linn. Grass 9
Impatiens balsamina L.  Flower 19
Ipomoea cairica (L.) Sweet Aerial 2
Ixora coccinea L.  Aerial 6 , 8
Jasminum graniflorum Flower bud 17
Kleinhovia hospita L.  Leaf 1 , 2
Litchi chinensis Seed 2
Magnolia grandiflora Leaf 8
Manihot esculenta
Ricinus communis Leaf 4 , 27
Zanthoxylum rhetsa Stem 6

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 3.5481 894
165 15-hydroxyprostaglandin dehydrogenase HPGD Homo sapiens 12.5893 894
165 15-hydroxyprostaglandin dehydrogenase HPGD Homo sapiens 22.3872 894
166 5-lipoxygenase/FLAP Homo sapiens >100000 10.1021/np0605539 17378609
1 Acetylcholinesterase Homo sapiens 168600 10.1021/jm049655r 15566295
1 Acetylcholinesterase Mus musculus 476370 10.1016/j.bmc.2014.01.010 24485122
1 Acetylcholinesterase Ache Mus musculus 476.37 1066955
33 acetylcholinesterase (Cartwright blood group) ACHE Homo sapiens 168.6 1066956
69 aldehyde dehydrogenase 1 family member A1 ALDH1A1 Homo sapiens 3.1623 1030
69 aldehyde dehydrogenase 1 family member A1 ALDH1A1 Homo sapiens 3.5481 1030
69 aldehyde dehydrogenase 1 family member A1 ALDH1A1 Homo sapiens 28.1838 1030
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 74.4 516862
167 Aldose reductase (AR) 74400 10.1016/j.bmcl.2010.08.038 20805028
93 arachidonate 15-lipoxygenase Oryctolagus cuniculus 16500 10.1021/np0605539 17378609
93 arachidonate 15-lipoxygenase ALOX15 Oryctolagus cuniculus 16.5 286229
168 arachidonate 5-lipoxygenase ALOX5 Homo sapiens 100 286228
118 ataxin 2 ATXN2 Homo sapiens 10 651635
118 ataxin 2 ATXN2 Homo sapiens 26.6795 651635
7 carbonic anhydrase 1 CA1 Homo sapiens 10.56 729563
8 carbonic anhydrase 12 CA12 Homo sapiens 4.05 729559
169 carbonic anhydrase 13 CA13 Homo sapiens 17.8 729558
170 Carbonic anhydrase 13 (CA XIII) Homo sapiens 17800 10.1016/j.bmc.2012.07.021 22892213
9 carbonic anhydrase 2 CA2 Homo sapiens 100 729562
130 carbonic anhydrase 7 CA7 Homo sapiens 8.71 729561
131 carbonic anhydrase 9 CA9 Homo sapiens 0.96 729560
99 Carbonic Anhydrase I Homo sapiens 10560 10.1016/j.bmc.2012.07.021 22892213
100 Carbonic Anhydrase II Homo sapiens >100000 10.1016/j.bmc.2012.07.021 22892213
132 Carbonic Anhydrase IX Homo sapiens 960 10.1016/j.bmc.2012.07.021 22892213
133 Carbonic Anhydrase VII Homo sapiens 8710 10.1016/j.bmc.2012.07.021 22892213
134 Carbonic Anhydrase XII Homo sapiens 4050 10.1016/j.bmc.2012.07.021 22892213
171 caspase 1 CASP1 Homo sapiens 1.9953 900
171 caspase 1 CASP1 Homo sapiens 3.9811 900
171 caspase 1 CASP1 Homo sapiens 5.0119 900
172 caspase 7 CASP7 Homo sapiens 1.2589 889
172 caspase 7 CASP7 Homo sapiens 3.9811 889
172 caspase 7 CASP7 Homo sapiens 5.0119 889
112 Cyclooxygenase Homo sapiens >100000 10.1021/np0605539 17378609
173 endoplasmic reticulum aminopeptidase 1 ERAP1 Homo sapiens 5.79 743314
174 endoplasmic reticulum aminopeptidase 2 ERAP2 Homo sapiens 0.678 743319
164 galactosidase alpha GLA Homo sapiens 3.9811 2107
164 galactosidase alpha GLA Homo sapiens 31.6228 1467
164 galactosidase alpha GLA Homo sapiens 35.4813 1467
164 galactosidase alpha GLA Homo sapiens 35.4813 2107
164 galactosidase alpha GLA Homo sapiens 44.6684 2107
84 geminin, DNA replication inhibitor GMNN Homo sapiens 14.581 624297
84 geminin, DNA replication inhibitor GMNN Homo sapiens 25.929 624296
14 glucosidase alpha, acid GAA Homo sapiens 35.4813 2112
14 glucosidase alpha, acid GAA Homo sapiens 44.6684 2112
14 glucosidase alpha, acid GAA Homo sapiens 7.0795 2112
73 glucosylceramidase beta GBA Homo sapiens 25.1189 2101
73 glucosylceramidase beta GBA Homo sapiens 28.1838 2101
175 Glyceraldehyde-3-phosphate dehydrogenase liver Homo sapiens 257039.58 10.1016/j.bmcl.2004.02.025 15081008
176 GNAS complex locus GNAS Homo sapiens 22.3872 624287
177 growth factor, augmenter of liver regeneration GFER Homo sapiens 4.403 493248
82 hypoxia inducible factor 1 subunit alpha HIF1A Homo sapiens 12.5893 914
82 hypoxia inducible factor 1 subunit alpha HIF1A Homo sapiens 12.5893 915
44 inositol monophosphatase 1 Impa1 Rattus norvegicus 10 1457
44 inositol monophosphatase 1 Impa1 Rattus norvegicus 11.2202 1457
90 karyopherin subunit beta 1 KPNB1 Homo sapiens 35.4813 540253
178 leucyl/cystinyl aminopeptidase Lnpep Mus musculus 0.348 743339
179 lysine acetyltransferase 2A KAT2A Homo sapiens 31.6228 504327
115 lysine methyltransferase 2A KMT2A Homo sapiens 3.9811 1766
116 menin 1 MEN1 Homo sapiens 3.9811 1766
180 peptidylprolyl cis/trans isomerase, NIMA-interacting 1 PIN1 Homo sapiens 63.0957 504891
152 prostaglandin-endoperoxide synthase 2 PTGS2 Homo sapiens 100 286230
181 RAN, member RAS oncogene family RAN Homo sapiens 35.4813 540253
182 RELA proto-oncogene, NF-kB subunit RELA Homo sapiens 20 733967
91 snurportin 1 SNUPN Homo sapiens 35.4813 540253
183 Sorbitol dehydrogenase Homo sapiens 137000 10.1016/j.bmcl.2010.08.038 20805028
184 thioredoxin reductase 1 Txnrd1 Rattus norvegicus 28.1838 588456
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 29.0929 686979

10. Chemical Vendors

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