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16beta-hydroxylupeol
- Family: Plantae - Guttiferae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)C[C@@H]2O)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C |
|---|---|
| InChI | InChI=1S/C30H50O2/c1-18(2)19-11-14-28(6)24(32)17-30(8)20(25(19)28)9-10-22-27(5)15-13-23(31)26(3,4)21(27)12-16-29(22,30)7/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20+,21-,22+,23-,24-,25+,27-,28+,29+,30+/m0/s1 |
| InChIKey | AJBZENLMTKDAEK-SKESNUHASA-N |
| Formula | C30H50O2 |
| HBA | 2 |
| HBD | 2 |
| MW | 442.73 |
| Rotatable Bonds | 1 |
| 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 | Garcinia epunctata | Guttiferae | Plantae | 2708839 |
Showing of synonyms
16beta-hydroxylupeol
Calenduladiol
Thurberin
UNII-5F669S8218
NSC 92227
5F669S8218
NSC-92227
NSC-133914
(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta(a)chrysene-4,9-diol
(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysene-4,9-diol
LUP-20(29)-ENE-3beta,16beta-DIOL
LUP-20(30)-ENE-3beta,16beta-DIOL
10070-48-1
Lup-20(29)-ene-3,16-diol, (3beta,16beta)-
NSC92227
SCHEMBL1251536
BDBM50019002
AKOS040750991
LUP-20(29)-ENE-3.BETA.,16.BETA.-DIOL
LUP-20(30)-ENE-3.BETA.,16.BETA.-DIOL
Q27261955
Lup-20(29)-ene-3,16-diol, (3.beta.,16.beta.)
LUP-20(29)-ENE-3,16-DIOL, (3.BETA.,16.BETA.)-
(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-4,9-diol
- Fotso GW, Ntumy AN, et al. (2014). Epunctanone, a New Benzophenone, and Further Secondary Metabolites from Garcinia epunctata Stapf (Guttiferae). Helvetica, 2014, 97(7), 957-964. [View]
Pubchem:
461835
Cas:
10070-48-1
Zinc:
ZINC000044386973
Nmrshiftdb2:
60029485
Chembl:
CHEMBL462795
Bindingdb:
50019002
CPRiL:
415542
SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5
Level: 0
Mol. Weight: 442.73 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.82
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.48
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.61
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.53
- Plasma Protein Binding
- 86.54
- 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
- 11.85
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.16
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.42
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.61
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -63.85
- Rat (Acute)
- 2.23
- Rat (Chronic Oral)
- 1.37
- Fathead Minnow
- 3.84
- 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
- 441.02
- Hydration Free Energy
- -3.03
- Log(D) at pH=7.4
- 6.87
- Log(P)
- 7.48
- Log S
- -6.82
- Log(Vapor Pressure)
- -8.84
- Melting Point
- 228.99
- pKa Acid
- 12.26
- pKa Basic
- 8.23
| 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 | 0.7968 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7814 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7811 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7483 |