Select a section from the left sidebar
Betulin
- Family: Plantae - Sapotaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | OC[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@@H](C3(C)C)O)C(=C)C |
|---|---|
| InChI | InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1 |
| InChIKey | FVWJYYTZTCVBKE-ROUWMTJPSA-N |
| Formula | C30H50O2 |
| HBA | 2 |
| HBD | 2 |
| MW | 442.73 |
| Rotatable Bonds | 2 |
| TPSA | 40.46 |
| LogP | 7.0 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 442.38 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Diospyros mespiliformis | Euphorbiaceae | Plantae | 413760 |
| 2 | Croton zambiescus | Euphorbiaceae | Plantae | 323089 |
| 3 | Melaleuca ericifolia | Myrtaceae | Plantae | 73757 |
| 4 | Platycelyphium voënse | Leguminosae/Fabaceae | Plantae | 149667 |
| 5 | Croton zambesicus | Euphorbiaceae | Plantae | 323089 |
| 6 | Croton zambesicus | Euphorbiaceae | Plantae | 323089 |
| 7 | Baillonella toxisperma (Pierre) | Sapotaceae | Plantae | 568230 |
Showing of synonyms
Betulin
473-98-3
Betulinol
Betuline
Trochol
Betulol
Betulinic alcohol
(+)-betulin
Lup-20(30)-ene-3beta,28-diol
NSC 4644
NSC-4644
EINECS 207-475-5
Lup-20(29)-ene-3 beta,28-diol
6W70HN7X7O
CHEBI:3086
ORISTRACT BTL
CP BETULIN
AI3-62999
Lup-20(29)-ene-3,28-diol, (3beta)-
BETULIN [MI]
(3beta)-lup-20(29)-ene-3,28-diol
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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]chrysen-9-ol
DTXSID101019934
Lup-20(29)-ene-3,28-diol, (3.beta.)-
Lup-20(30)-ene-3.beta.,28-diol
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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)chrysen-9-ol
BETULIN [INCI]
DTXCID801477793
207-475-5
Lup-20(29)-ene-3beta,28-diol
Lup-20(29)-ene-3b,28-diol
MFCD00016802
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-(hydroxymethyl)-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}]henicosan-17-ol
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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]chrysen-9-ol
SR-05000002167
NSC4644
UNII-6W70HN7X7O
NSC692218
Lup-20(29)-ene-3.beta.,28-diol
Betulin (Standard)
Betulinol (obsol.)
Betulin, 23
Betulin, >=98%
Prestwick3_000990
Betulin, analytical standard
BSPBio_001059
CHEMBL23236
SCHEMBL131739
BPBio1_001165
MEGxp0_001726
ACon1_000091
BDBM23207
HY-N0083R
HMS2098E21
7372-31-8
EX-A3354
HY-N0083
S4754
Lup-20(29)-ene-3 ,28-diol
AKOS005267212
Lup-20(29)-ene-3beta ,28-diol
Lup-20(30)-ene-3beta ,28-diol
CCG-208619
CS-6156
FB29605
GS-3254
LMPR0106140005
NSC-692218
NCGC00168803-01
NCGC00168803-02
NCGC00168803-04
AB00513988
B0803
NS00018049
(3.beta.)-Lup-20(29)-ene-3,28-diol
C08618
Lup-20(29)-ene-3,28-diol, (3beta )-
Q419726
SR-05000002167-2
SR-05000002167-3
BRD-K64874225-001-01-3
BRD-K64874225-001-04-7
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3 a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol
(1R,3AS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,1 1a-pentamethyl-1-(prop-1-en-2-y l)icosahydro-1H-cyclopenta[a]chrysen-9-ol
- Abdel Bar FM, Zaghloul AM, et al. (2008). Antiproliferative triterpenes from Melaleuca ericifolia. Journal of Natural Products,2008,71(10),1787-1790. [View] [PubMed]
- Mohamed LE, El-Nur EE, et al. (2009). Bioactive natural products from two Sudanese medicinal plants Diospyros mespiliformis and Croton zambesicus. Records of Natural Products,2009,3(4),198-203. [View]
- Ngadjui BT, Abegaz BM, et al. (2002). Diterpenoids from the stem bark of Croton zambesicus.. Phytochemistry,2002, 60(4), 345-349. [View] [PubMed]
- Ngadjui BT, Abegaz BM, et al. (2002). Diterpenoids from the stem bark of Croton zambesicus.. Phytochemistry,2002, 60(4), 345-349. [View] [PubMed]
- Gumula I, Heydenreic M, et al. (2012). Four isoflavanones from the stem bark of Platycelphium voënse.. Phytochemistry Letters,2012,5(1),150–154. [View] [PubMed]
- Pierre Yemback, Kenneth O. Eyong, et al. (2023). Lupane derivatives: Design, isolation, synthesis and evaluation of antiplasmodial activity against Plasmodium falciparum 3D7 strain. Phytochemistry Letters, 2023, 57, 26-35. [View]
Pubchem:
72326
Cas:
473-98-3
Gnps:
CCMSLIB00006412342
Zinc:
ZINC000003978650
Kegg Ligand:
C08618
Chebi:
3086
Nmrshiftdb2:
70127540
Metabolights:
MTBLC3086
Chembl:
CHEMBL23236
Drugbank:
DB16890
Bindingdb:
23207
CPRiL:
55778
SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5
Level: 0
Mol. Weight: 442.73 g/mol
Alpha-glucosidase inhibitory
Absorption
- Caco-2 (logPapp)
- -4.83
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.45
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.9
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.48
- Plasma Protein Binding
- 85.42
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.18
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.24
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.63
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.54
- 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
- Toxic
- T. Pyriformis
- -77.85
- Rat (Acute)
- 2.46
- Rat (Chronic Oral)
- 1.49
- Fathead Minnow
- 3.91
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 407.9
- Hydration Free Energy
- -2.57
- Log(D) at pH=7.4
- 6.94
- Log(P)
- 7.41
- Log S
- -6.68
- Log(Vapor Pressure)
- -8.95
- Melting Point
- 231.41
- pKa Acid
- 12.64
- pKa Basic
- 7.78
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8342 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8342 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7811 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7811 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7717 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7717 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7302 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7302 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7044 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7044 |