5beta,6beta-epoxy-4beta,17alpha,27-trihydroxy-1-oxowitha-2,24-dienolide - Compound Card

5beta,6beta-epoxy-4beta,17alpha,27-trihydroxy-1-oxowitha-2,24-dienolide

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5beta,6beta-epoxy-4beta,17alpha,27-trihydroxy-1-oxowitha-2,24-dienolide

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Withanolide-Type Steroid
Canonical Smiles OCC1=C(C)CC(OC1=O)[C@@H]([C@@]1(O)CCC2[C@]1(C)CCC1C2C[C@@H]2[C@]3([C@]1(C)C(=O)C=C[C@@H]3O)O2)C
InChI InChI=1S/C28H38O7/c1-14-11-20(34-24(32)17(14)13-29)15(2)27(33)10-8-18-16-12-23-28(35-23)22(31)6-5-21(30)26(28,4)19(16)7-9-25(18,27)3/h5-6,15-16,18-20,22-23,29,31,33H,7-13H2,1-4H3/t15-,16?,18?,19?,20?,22-,23+,25-,26-,27-,28+/m0/s1
InChIKey HLZVPWRVYKJCMY-QDKFTSETSA-N
Formula C28H38O7
HBA 7
HBD 3
MW 486.61
Rotatable Bonds 3
TPSA 116.59
LogP 2.47
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 486.26
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: 162842864
Nmrshiftdb2: 70038241

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCC(O1)CC(CC2)C(C2C3CC(C456)O6)CCC3C4C(=O)C=CC5

Level: 1

Mol. Weight: 486.61 g/mol

Structure

SMILES: C123C(O3)CC4C5C(CCC5)CCC4C1C(=O)C=CC2

Level: 0

Mol. Weight: 486.61 g/mol

Structure

SMILES: O=C1C=CCCO1

Level: 0

Mol. Weight: 486.61 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.14
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.34
Plasma Protein Binding
47.92
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
11.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.92
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.34
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.94
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
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
-554.16
Rat (Acute)
4.11
Rat (Chronic Oral)
2.26
Fathead Minnow
3.79
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
507.18
Hydration Free Energy
-2.97
Log(D) at pH=7.4
1.72
Log(P)
1.59
Log S
-4.17
Log(Vapor Pressure)
-9.25
Melting Point
230.31
pKa Acid
4.82
pKa Basic
4.67
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 0.9086
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9086
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9045
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9045
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8739
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8739
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8419
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8419
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8280
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8280
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8217
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8217
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8102
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8102
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7979
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7979
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7945
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7945
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7743
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7743
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7511
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7511
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7464
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7464
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7365
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7365
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7272
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7272
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7190
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7190
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7009
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7009

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