16alpha-hydroxytaraxasterol-3-acetate - Compound Card

16alpha-hydroxytaraxasterol-3-acetate

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16alpha-hydroxytaraxasterol-3-acetate

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Taraxasterol-Type Triterpene
Canonical Smiles CC(=O)OC1CC[C@]2(C(C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@]1([C@H]2C(C)C(=C)CC1)O)C)C
InChI InChI=1S/C31H50O3/c1-19-11-16-31(33)18-17-29(7)22(26(31)20(19)2)9-10-24-28(6)14-13-25(34-21(3)32)27(4,5)23(28)12-15-30(24,29)8/h20,22-26,33H,1,9-18H2,2-8H3/t20?,22-,23?,24-,25?,26+,28+,29-,30-,31-/m1/s1
InChIKey KYHNPYRBOLQIRD-IJAVIMASSA-N
Formula C31H50O3
HBA 3
HBD 1
MW 470.74
Rotatable Bonds 1
TPSA 46.53
LogP 7.32
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 470.38
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: 162909502

No compound-protein relationship available.

Structure

SMILES: C=C(C1)CCC(CC2)C1C3CCC(C4C23)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 470.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.65
Plasma Protein Binding
84.23
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.34
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.21
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.32
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
-135.13
Rat (Acute)
2.12
Rat (Chronic Oral)
1.36
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
456.92
Hydration Free Energy
-2.57
Log(D) at pH=7.4
6.68
Log(P)
7.42
Log S
-6.91
Log(Vapor Pressure)
-7.91
Melting Point
203.2
pKa Acid
11.85
pKa Basic
7.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8153
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8153
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7871
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7871
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7799
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7799
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7388
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7388
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7354
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7354
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7345
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7345
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7200
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7200

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