2,3-dihydroxywithaferin A-3beta-O-sulfate - Compound Card

2,3-dihydroxywithaferin A-3beta-O-sulfate

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2,3-dihydroxywithaferin A-3beta-O-sulfate

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Withanolide-Type Steroid
Canonical Smiles OCC1=C(C)CC(OC1=O)[C@@H](C1CCC2[C@]1(C)CCC1C2C[C@@H]2[C@]3([C@]1(C)C(=O)CC([C@@H]3O)OS(=O)(=O)O)O2)C
InChI InChI=1S/C28H40O10S/c1-13-9-20(36-25(32)16(13)12-29)14(2)17-5-6-18-15-10-23-28(37-23)24(31)21(38-39(33,34)35)11-22(30)27(28,4)19(15)7-8-26(17,18)3/h14-15,17-21,23-24,29,31H,5-12H2,1-4H3,(H,33,34,35)/t14-,15?,17?,18?,19?,20?,21?,23-,24+,26-,27+,28+/m1/s1
InChIKey DVTZXBWRHRFDEE-IHKKPUHSSA-N
Formula C28H40O10S
HBA 9
HBD 3
MW 568.69
Rotatable Bonds 5
TPSA 159.96
LogP 2.37
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 568.23
Number of Lipinski Rule Violations 1
# 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: 162844888
Nmrshiftdb2: 70038243

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCC(O1)CC(CC2)C(C2C3CC(C456)O6)CCC3C4C(=O)CCC5

Level: 1

Mol. Weight: 568.69 g/mol

Structure

SMILES: C123C(O3)CC4C5C(CCC5)CCC4C1C(=O)CCC2

Level: 0

Mol. Weight: 568.69 g/mol

Structure

SMILES: O=C1C=CCCO1

Level: 0

Mol. Weight: 568.69 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.08
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
67.39
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
6.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.41
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.88
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-2596.08
Rat (Acute)
1.84
Rat (Chronic Oral)
2.74
Fathead Minnow
7.58
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
479.39
Hydration Free Energy
-3.02
Log(D) at pH=7.4
1.53
Log(P)
-1.15
Log S
-3.85
Log(Vapor Pressure)
-11.4
Melting Point
260.36
pKa Acid
3.04
pKa Basic
4.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7873
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7873
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7841
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7841
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7122
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7122
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7106
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7106
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7069
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7069
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7050
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7050

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