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Betulinic acid
- Family: Plantae - Sterculiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Pentacyclic Triterpenoid
| Canonical Smiles | CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O |
|---|---|
| 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) |
| InChIKey | QGJZLNKBHJESQX-UHFFFAOYSA-N |
| Formula | C30H48O3 |
| HBA | 2 |
| HBD | 2 |
| MW | 456.71 |
| Rotatable Bonds | 2 |
| TPSA | 57.53 |
| LogP | 7.09 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 456.36 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cola lateritia | Sterculiaceae | Plantae | 577684 |
Showing of synonyms
Betulinic acid
472-15-1
Mairin
Betulic acid
Lupatic Acid
Als-357
3-Hydroxylup-20(29)-en-28-oic acid
CCRIS 6748
NSC 113090
EINECS 207-448-8
Beta-betulinic acid
NSC 677578
NSC-677578
CHEBI:3087
UNII-4G6A18707N
4G6A18707N
NSC-113090
Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-
Lup-20(29)-en-28-oic acid, 3beta-hydroxy-
(3beta)-3-hydroxylup-20(29)-en-28-oic acid
3beta-hydroxylup-20(29)-en-28-oic acid
NSC113090
(3beta)-3-Hydroxy-lup-20(29)-en-28-oic Acid
207-448-8
3beta-Hydroxy-20(29)-lupaene-28-oic acid
.beta.-betulinic acid
MFCD00009619
NSC677578
CHEMBL269277
3beta-Hydroxy-lup-20(29)-en-28-oic acid
Betulinicacid
(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
(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)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
SMR000445624
Betulinic-acid
Betulinic acid?
Prestwick_95
Betulinic Acid, 24
Prestwick0_000417
Prestwick1_000417
Prestwick2_000417
Prestwick3_000417
Betulinic acid (Standard)
BETULINIC ACID [MI]
Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-
SCHEMBL61767
BSPBio_000374
BSPBio_001587
Cid_64971
MLS000728510
MLS006011257
SPBio_002313
BPBio1_000412
GTPL3945
BDBM23208
DTXSID80861974
GLXC-06559
HMS1569C16
HMS1791P09
HMS1989P09
HMS2096C16
HMS2232K03
HMS3402P09
Betulinic acid, analytical standard
Betulinic acid, >=98% (HPLC)
MSK40138
HB3799
HY-10529R
S3603
STL570261
AKOS015920276
Betulinic acid, technical grade, 90%
CCG-208159
CS-1216
DB12480
FB16425
LMPR0106140004
RL9-080
SMP2_000205
NCGC00163409-02
NCGC00163409-03
NCGC00163409-09
NCGC00163409-12
BP-25391
DS-15257
HY-10529
3b-Hydroxy-20(29)-lupaene-28-oic acid
NS00042781
C08619
Lup-20(29)-en-28-oic acid, 3beta -hydroxy-
3-Hydroxy-(3beta)-Lup-20(29)-en-28-oic acid
Q384111
SR-01000779609
SR-01000779609-3
BRD-K45401373-001-05-0
BRD-K45401373-001-20-9
BRD-K45401373-001-22-5
(3.BETA.)-3-HYDROXYLUP-20(29)-EN-28-OIC 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-carboxylicacid
(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-carboxylicacid
06L
- Kamdem M, Ojo O, et al. (2022). Pentacyclic Triterpenoids, Phytosteroids and Fatty Acid Isolated from the Stem-bark of Cola lateritia K. Schum. (Sterculiaceae) of Cameroon origin; Evaluation of Their Antibacterial Activity. Arabian Journal of Chemistry, 2022, 15(1), 103506. [View]
Pubchem:
64971
Cas:
472-15-1
Gnps:
CCMSLIB00006400554
Zinc:
ZINC000004097714
Kegg Ligand:
C08619
Chebi:
3087
Nmrshiftdb2:
40265324
Metabolights:
MTBLC3087
Chembl:
CHEMBL269277
Drugbank:
DB12480
Pdb Ligand:
06L
Bindingdb:
23208
Selleck:
betulinic-acid
CPRiL:
55981
SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5
Level: 0
Mol. Weight: 456.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.46
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.67
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.97
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.02
- Plasma Protein Binding
- 23.65
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 2.49
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.05
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.94
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.66
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -103.76
- Rat (Acute)
- 2.47
- Rat (Chronic Oral)
- 2.11
- Fathead Minnow
- 4.31
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 436.63
- Hydration Free Energy
- -2.51
- Log(D) at pH=7.4
- 5.35
- Log(P)
- 6.43
- Log S
- -6.54
- Log(Vapor Pressure)
- -8.76
- Melting Point
- 273.41
- pKa Acid
- 5.97
- pKa Basic
- 8.58
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8557 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.7801 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.7771 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 3 | 0.7745 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7663 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7272 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7213 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7203 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7170 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7086 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7064 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7013 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7005 |