Betulinic acid

  • GreenMolBD CID : 718
  • Molecular Formula : C30H48O3
  • Molecular Weight : 456.711
  • Exact Molecular Mass : 456.36
  • IUPAC Name : (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
  • InChI : InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
  • InChI Key : QGJZLNKBHJESQX-FZFNOLFKSA-N
  • Canonical SMILES : CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O
  • Isomeric SMILES : CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

1.2. Taxonomy Tree

1.3. Alternative Parent

18-hydroxysteroids; Oxosteroids; Secondary alcohols; Cyclic alcohols and derivatives; Monocarboxylic acids and derivatives; Carboxylic acids; Organic oxides; Hydrocarbon derivatives; Carbonyl compounds;

1.4. Molecular Framework

Aliphatic homopolycyclic compounds

1.5. Substituents

Triterpenoid; 18-oxosteroid; 18-hydroxysteroid; Oxosteroid; Hydroxysteroid; Steroid; Cyclic alcohol; Secondary alcohol; Monocarboxylic acid or derivatives; Carboxylic acid; Carboxylic acid derivative; Hydrocarbon derivative; Organic oxygen compound; Alcohol; Organooxygen compound; Carbonyl group; Organic oxide; Aliphatic homopolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
7.0895 57.53 2 3 33 2 0 0 13.2612 689.613 489.581 0.662272

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-293.820282 2.14 -4.434 -9.84316 0.97513 5.409

4. Compound Reactivity

DLP nRFG nLMR
2 0 3

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 2.81853 2785.43 0.00437385 Moderate Weak Severe Degradable 3.27E-5 0.852853

6. Drug-Likeliness Test

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

7. Synonyms

Name
betulinic acid
472-15-1
Mairin
Betulic acid
NSC 113090
CCRIS 6748
3-Hydroxylup-20(29)-en-28-oic acid
UNII-4G6A18707N
3beta-Hydroxy-20(29)-lupaene-28-oic acid
EINECS 207-448-8
NSC677578
NSC 677578
CHEBI:3087
CHEMBL269277
3beta-Hydroxy-lup-20(29)-en-28-oic acid
MFCD00009619
Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-
AK-72848
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
SMR000445624
BIDF1001
Betulinicacid
Lupatic Acid
Prestwick_95
beta-betulinic acid
(+)-Betulinic acid
Betulinic Acid, 24
PubChem16912
Prestwick0_000417
Prestwick1_000417
Prestwick2_000417
Prestwick3_000417
als-357
D0R9YR
AC1L22BQ
Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-
SCHEMBL61767
BSPBio_000374
BSPBio_001587
cid_64971
MLS000728510
MLS006011257
SPBio_002313
BIDF1011
BPBio1_000412
GTPL3945
BDBM23208
AOB5668
MolPort-003-939-279
QGJZLNKBHJESQX-FZFNOLFKSA-N
ZX-AFC002755
ZX-AFC002764
HMS1569C16
HMS1791P09
HMS1989P09
HMS2096C16
HMS2232K03
HMS3402P09
Betulinic acid, analytical standard
Betulinic acid, >=98% (HPLC)
ZINC4097714
2267AH
s3603
AKOS015920276
Betulinic acid, technical grade, 90%
4G6A18707N
ACN-035194
API0005116
CCG-208159
CS-1216
DB12480
EBD2184748
LMPR0106140004
NSC-677578
RL03745
RL9-080
SMP2_000205
3-Hydroxy-20(29)-lupen-28-oic acid
NCGC00163409-02
NCGC00163409-03
AJ-48006
BR-72848
BT000817
DR002826
HY-10529
PL057097
SC-19742
3|A-Hydroxylup-20(29)-en-28-oic Acid
3beta-hydroxylup-20(29)-en-28-oic acid
AX8001981
LS-175037
FT-0082693
N1343
ST24030165
C08619
Lup-20(29)-en-28-oic acid, 3beta-hydroxy-
M-9067
Lup-20(29)-en-28-oic acid, 3beta -hydroxy-
(3|A)-3-HydroxyLup-20(29)-en-28-oic Acid
3-Hydroxy-(3beta)-Lup-20(29)-en-28-oic acid
472B151
Q-100500
BRD-K45401373-001-05-0
Lup-20(29)-en-28-oic acid, 3-hydroxy-, 3 beta
Lup-20(29)-en-28-oic acid, 3beta-hydroxy- (8CI)
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-HYDROXY-1,2,14,18,18-PENTAMETHYL-8-(PROP-1-EN-2-YL)PENTACYCLO[11.8.0.0(2),(1)?.0?,?.0(1)?,(1)?]HENICOSANE-5-CARBOXYLIC ACID
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid
(1R,3 aS,5aR,5bR,7aR,9S,11aR,11bR,13 aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-eicosahydro-cyclopenta[a]chrysene-3a-carboxylic acid
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
Butulinic Acid
DS-15257
BG01746469
SR-01000779609
SR-01000779609-3

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Betulinic acid
Ammannia baccifera L. Root; Aerial 3
Artocarpus heterophyllus Lamk. Leaf 2
Avicennia marina Aerial 3 , 14
Crataeva nurvala Stem Bark 4
Duabanga grandiflora Stem Bark; Stem 1
Ficus elastica Bark of Aerial Root 3
Juglans regia Stem Bark 17 , 20
Lumnitzera racemosa Stem 1
Melastoma malabathricum Leaf 3 , 4
Scoparia dulcia L Whole Plant; Aerial 6 , 2
Sesbania grandiflora Root 4

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
1015 albumin ALB Homo sapiens 0.593 1238544
1015 albumin ALB Homo sapiens 1.3 1238541
1015 albumin ALB Homo sapiens 4.5 1238540
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 11 697010
455 aldo-keto reductase family 1 member B10 AKR1B10 Homo sapiens 2 697009
456 Aldo-keto reductase family member 1B10 (AKR1B10) 2000 10.1021/np200118q 21561086
167 Aldose reductase (AR) 11000 10.1021/np200118q 21561086
733 apolipoprotein B mRNA editing enzyme catalytic subunit 3F APOBEC3F Homo sapiens 6.3096 602313
341 Botulinum neurotoxin type A Clostridium botulinum 20000 10.1016/j.bmcl.2011.02.115 21421315
341 Botulinum neurotoxin type A Clostridium botulinum 14300 10.1016/j.bmcl.2011.02.115 21421315
491 cystic fibrosis transmembrane conductance regulator CFTR Homo sapiens 40.9 624344
159 dipeptidyl peptidase 4 DPP4 Homo sapiens 55.82 1118023
11 DNA polymerase beta Rattus norvegicus 14000 10654414
11 DNA polymerase beta Rattus norvegicus 6500 10654414
11 DNA polymerase beta Homo sapiens 33700 10.1016/j.bmc.2008.02.071 18343122
11 DNA polymerase beta Homo sapiens 46250 10.1016/j.bmc.2008.02.071 18343122
11 DNA polymerase beta Homo sapiens 43600 10.1021/np0301893 14640519
11 DNA polymerase beta Polb Rattus norvegicus 6.5 376700
11 DNA polymerase beta Polb Rattus norvegicus 14 376699
11 DNA polymerase beta POLB Homo sapiens 3.1623 485314
84 geminin, DNA replication inhibitor GMNN Homo sapiens 0.92 624296
321 glycogen phosphorylase, muscle associated PYGM Oryctolagus cuniculus 43 404873
321 glycogen phosphorylase, muscle associated PYGM Oryctolagus cuniculus 43 603224
322 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 43000 10.1021/jm8000949 18517260
322 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 43000 10.1016/j.ejmech.2011.02.053 21439694
458 GP41 >100000 10.1021/jm500763m 25156906
459 G-protein coupled bile acid receptor 1 Homo sapiens 1040 10.1021/jm900872z 19911773
1140 Human immunodeficiency virus type 1 protease Human immunodeficiency virus 1 >219000 10.1021/jm950922q 8676334
1141 Liver X receptor beta (LXRB) >50000 10.1021/np050182g 16124770
1142 LXR-alpha Homo sapiens >50000 10.1021/np050182g 16124770
1143 nuclear receptor subfamily 1 group H member 2 NR1H2 Homo sapiens 25 403097
1143 nuclear receptor subfamily 1 group H member 2 NR1H2 Homo sapiens 50 403100
1144 nuclear receptor subfamily 1 group H member 3 NR1H3 Homo sapiens 25 403095
1144 nuclear receptor subfamily 1 group H member 3 NR1H3 Homo sapiens 50 403099
361 parathyroid hormone 1 receptor PTH1R Homo sapiens 7.0795 743266
72 peroxisome proliferator activated receptor gamma Pparg Mus musculus 100 1180479
372 Peroxisome proliferator-activated receptor gamma Mus musculus >100000 10.1021/np500150f 24955889
125 Rap guanine nucleotide exchange factor 4 RAPGEF4 Homo sapiens 100 720708
1097 Serum albumin Homo sapiens 0.45 26112446
1097 Serum albumin Homo sapiens 0.593 26112446
1097 Serum albumin Homo sapiens 0.13 26112446
1145 SUMO1 activating enzyme subunit 1 Homo sapiens 9240 2006
1145 SUMO1 activating enzyme subunit 1 SAE1 Homo sapiens 9.24 2006
1145 SUMO1 activating enzyme subunit 1 SAE1 Homo sapiens 13.16 2018
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 3.6626 686978
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 5.8048 686979
1146 ubiquitin conjugating enzyme E2 I UBE2I Homo sapiens 9.24 2006
1146 ubiquitin conjugating enzyme E2 I UBE2I Homo sapiens 13.16 2018
1147 ubiquitin like modifier activating enzyme 2 UBA2 Homo sapiens 9.24 2006
1147 ubiquitin like modifier activating enzyme 2 UBA2 Homo sapiens 13.16 2018
1148 Zinc finger protein GLI1 Homo sapiens 32000 10.1016/j.bmc.2008.09.053 18842418
1148 Zinc finger protein GLI1 Homo sapiens 32000 10.1021/jm801420y 19309080

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
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251915309AvaChem ScientificSource URLSource Detail472-15-1Source Record URL
255345086BiosynthSource URLSource DetailQ-100500Source Record URL
252039686Bide Pharmatech Ltd.Source URLSource DetailBD1981Source Record URL
152059695AKos Consulting & SolutionsSource URLSource DetailAKOS015920276Source Record URL
319552767AbovChem LLCSource URLSource DetailHY-10529Source Record URL
310267793Glentham Life Sciences Ltd.Source URLSource DetailGP1450Source Record URL
163620710MedChemexpress MCESource URLSource DetailHY-10529Source Record URL
57315217NovoSeekSource URLSource Detail64971Source Record URL
3570957381717 CheMall CorporationSource URLSource DetailBG01746469Source Record URL
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104332531ABI ChemSource URLSource DetailAC1L22BQSource Record URL
346689747LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00188803Source Record URL
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319451804eNovation ChemicalsSource URLSource DetailD380994Source Record URL
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318356576CambridgeChemSource URLSource DetailB1981Source Record URL
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163688533EMD MilliporeSource URLSource Detail200498Source Record URL