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Taraxasterol
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
| Canonical Smiles | C=C1CC[C@]2([C@H]([C@@H]1C)[C@H]1CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C |
|---|---|
| InChI | InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22+,23-,24+,25-,27-,28+,29-,30-/m1/s1 |
| InChIKey | XWMMEBCFHUKHEX-ZJJHUPNDSA-N |
| Formula | C30H50O |
| HBA | 1 |
| HBD | 1 |
| MW | 426.73 |
| Rotatable Bonds | 0 |
| TPSA | 20.23 |
| LogP | 8.02 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 426.39 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Carthamus mareoticus | Asteraceae | Plantae | 123811 |
| 2 | Centaurea omphalotricha | Asteraceae | Plantae | 41503 |
| 3 | Reichardia tingitana | Asteraceae | Plantae | 43208 |
Showing of synonyms
Taraxasterol
1059-14-9
Isolactucerol
Anthesterin
Lactucerol
UNII-64SK2ERN9P
64SK2ERN9P
Saussurol
Alpha-lactucerol
Taraxasterin
CHEBI:9401
18alpha,19betaH-Urs-20(30)-en-3beta-ol
Urs-20(30)-en-3-ol, (3beta,18alpha,19alpha)-
(3beta,18alpha,19alpha)-urs-20(30)-en-3-ol
Taraxast-20(30)-en-3beta-ol
(3S,4aR,6aR,6aR,6bR,8aR,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-ol
18alpha,19alpha-urs-20(30)-en-3beta-ol
(+)-Taraxasterol
TARAXASTEROL [MI]
.ALPHA.-LACTUCEROL
SCHEMBL222272
EX-A8003F
XWMMEBCFHUKHEX-ZJJHUPNDSA-N
Urs-20(30)-en-3-ol, (3.beta.,18.alpha.,19.alpha.)-
HY-N1178
AKOS016009424
FT65570
LMPR0106180006
AC-31291
DA-67930
TARAXAST-20(30)-EN-3.BETA.-OL
CS-0016469
Q27108380
(3.BETA.,18.ALPHA.,19.ALPHA.)-URS-20(30)-EN-3-OL
- Abdel-Mogib M, Awad SN, et al. (1993). A sesquiterpene glucoside from Reichardia tingitana. Phytochemistry,1993,34(5),1434-1435. [View]
- Mouffok S, Haba H, et al. (2012). Chemical constituents of Centaurea omphalotricha Coss. & Durieu ex Batt. & Trab.. Records of Natural Products,2012,6(3),292-295. [View]
- Amer ME, Abdallah RM, et al. (1989). Two sesquiterpene fucopyranosides from Carthamus mareoticus. Phytochemistry,1989,28(4),1263-1264. [View]
Pubchem:
115250
Cas:
1059-14-9
Gnps:
CCMSLIB00006502589
Zinc:
ZINC000004027386
Chebi:
9401
Nmrshiftdb2:
60060256
Metabolights:
MTBLC9401
CPRiL:
77096
SMILES: C=C(C1)CCC(CC2)C1C3CCC(C4C23)C5C(CC4)CCCC5
Level: 0
Mol. Weight: 426.73 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.78
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.42
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.81
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.73
- Plasma Protein Binding
- 87.78
- 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
- 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
- 11.68
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.59
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.86
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.87
- 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
- -38.35
- Rat (Acute)
- 2.34
- Rat (Chronic Oral)
- 1.41
- Fathead Minnow
- 3.92
- 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
- 401.52
- Hydration Free Energy
- -3.42
- Log(D) at pH=7.4
- 7.59
- Log(P)
- 8.33
- Log S
- -7.15
- Log(Vapor Pressure)
- -7.97
- Melting Point
- 210.63
- pKa Acid
- 13.2
- pKa Basic
- 7.85
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7525 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7525 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7164 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7164 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7151 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7151 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7076 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7076 |