Withanolide J - Compound Card

Withanolide J

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Withanolide J

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Withanolide-Type Steroid
Canonical Smiles CC1=C(C)C(=O)O[C@H](C1)[C@@]([C@@]1(O)CC[C@@]2([C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)C(=O)C=CC2)O)(O)C
InChI InChI=1S/C28H38O6/c1-16-15-22(34-23(30)17(16)2)26(5,31)28(33)14-13-27(32)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6,8-9,19-20,22,31-33H,7,10-15H2,1-5H3/t19-,20+,22+,24-,25-,26-,27+,28+/m0/s1
InChIKey GQHHHBATDOXAEP-WEJNEFSASA-N
Formula C28H38O6
HBA 6
HBD 3
MW 470.61
Rotatable Bonds 2
TPSA 104.06
LogP 3.54
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 470.27
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Withania adpressa Solanaceae Plantae 2201923
2 Withania adpressa Solanaceae Plantae 2201923

Showing of synonyms

  • Abdeljebbar LH, Benjouad A, et al. (2009). Antiproliferative effects of withanolides from Withania adpressa. Therapie,2009,64(2),121-127. [View] [PubMed]
  • Abdeljebbar LH, Humam M, et al. (2007). Withanolides from Withania adpressa. Helvetica Chimica Acta,2007,90,346-352. [View]
Pubchem: 21679022
Nmrshiftdb2: 70064873

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 470.61 g/mol

Structure

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

Level: 0

Mol. Weight: 470.61 g/mol

Structure

SMILES: O=C1C=CCCO1

Level: 0

Mol. Weight: 470.61 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
78.51
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
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
4.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.99
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.44
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.03
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-174.6
Rat (Acute)
3.65
Rat (Chronic Oral)
1.83
Fathead Minnow
4.03
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
481.1
Hydration Free Energy
-3.13
Log(D) at pH=7.4
2.75
Log(P)
3.14
Log S
-4.44
Log(Vapor Pressure)
-9.05
Melting Point
253.98
pKa Acid
6.97
pKa Basic
5.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9021
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9021
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8526
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8526
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7323
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7323
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7246
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7246
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7164
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7164

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