4beta,17alpha,27-trihydroxy-1-oxo-22-R-witha-2,5,24-trienolide - Compound Card

4beta,17alpha,27-trihydroxy-1-oxo-22-R-witha-2,5,24-trienolide

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4beta,17alpha,27-trihydroxy-1-oxo-22-R-witha-2,5,24-trienolide

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Withanolide-Type Steroid
Canonical Smiles OCC1=C(C)CC(OC1=O)C([C@@]1(O)CCC2[C@]1(C)CCC1C2CC=C2[C@]1(C)C(=O)C=C[C@@H]2O)(C)C
InChI InChI=1S/C29H40O6/c1-16-14-24(35-25(33)18(16)15-30)26(2,3)29(34)13-11-19-17-6-7-21-22(31)8-9-23(32)28(21,5)20(17)10-12-27(19,29)4/h7-9,17,19-20,22,24,30-31,34H,6,10-15H2,1-5H3/t17?,19?,20?,22-,24?,27-,28+,29-/m0/s1
InChIKey NENONOJDBHLHKY-VEUITRMFSA-N
Formula C29H40O6
HBA 6
HBD 3
MW 484.63
Rotatable Bonds 3
TPSA 104.06
LogP 3.65
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 484.28
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Withania frutescens Solanaceae Plantae 367782

Showing of synonyms

  • El Bouzidi L, Mahiou-Leddet V, et al. (2013). Cytotoxic withanolides from the leaves of Moroccan Withania frutescens. Pharmaceutical Biology,2013,51(8),1040-1046. [View] [PubMed]
Pubchem: 162817073
Nmrshiftdb2: 70038242

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCC(O1)CC2CCC(C23)C4C(CC3)C5C(=CC4)CC=CC5=O

Level: 1

Mol. Weight: 484.63 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3C(=O)C=CC4

Level: 0

Mol. Weight: 484.63 g/mol

Structure

SMILES: O=C1C=CCCO1

Level: 0

Mol. Weight: 484.63 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.11
Plasma Protein Binding
71.17
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.4
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.98
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.54
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.67
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-311.14
Rat (Acute)
3.14
Rat (Chronic Oral)
2.13
Fathead Minnow
4.35
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
499.7
Hydration Free Energy
-2.9
Log(D) at pH=7.4
2.95
Log(P)
2.23
Log S
-4.75
Log(Vapor Pressure)
-9.12
Melting Point
246.4
pKa Acid
6.45
pKa Basic
5.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8067
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8067
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7844
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7844
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7704
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7704
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7415
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7415
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7362
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7362
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7176
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7176
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7018
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7018

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