3-taraxasterol - Compound Card

3-taraxasterol

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3-taraxasterol

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Taraxasterol-Type Triterpene
Canonical Smiles C=C1CC[C@]2([C@@H](C1C)[C@H]1CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CCC1[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-RWRSZONCSA-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 Pergularia tomentosa Apocynaceae Plantae 264979

Showing of synonyms

  • Babaamer ZY, Sakhri L, et al. (2012). Two new taraxasterol-type triterpenes from Pergularia tomentosa growing wild in Algeria. Journal of Asian Natural Products Research,2012,14(12),1137-1143. [View] [PubMed]
Pubchem: 162988003

No compound-protein relationship available.

Structure

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)
-4.8
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
-2.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.73
Plasma Protein Binding
82.73
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
11.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.91
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
5.91
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
-36.23
Rat (Acute)
2.35
Rat (Chronic Oral)
1.4
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
400.92
Hydration Free Energy
-3.46
Log(D) at pH=7.4
7.56
Log(P)
8.16
Log S
-7.17
Log(Vapor Pressure)
-7.84
Melting Point
217.33
pKa Acid
13.19
pKa Basic
7.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8559
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8559
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7722
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7722
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7661
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7661
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7619
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7619
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7046
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7046

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