14alpha,15alpha,17beta,20beta-tetrahydroxy-1-oxo-(22R)-witha-2,5,24-trienolide - Compound Card

14alpha,15alpha,17beta,20beta-tetrahydroxy-1-oxo-(22R)-witha-2,5,24-trienolide

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14alpha,15alpha,17beta,20beta-tetrahydroxy-1-oxo-(22R)-witha-2,5,24-trienolide

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)C[C@@H]([C@@]2([C@]1(C)CCC1C2CC=C2[C@]1(C)C(=O)C=CC2)O)O)(O)C
InChI InChI=1S/C28H38O7/c1-15-13-22(35-23(31)16(15)2)26(5,32)27(33)14-21(30)28(34)19-10-9-17-7-6-8-20(29)25(17,4)18(19)11-12-24(27,28)3/h6,8-9,18-19,21-22,30,32-34H,7,10-14H2,1-5H3/t18?,19?,21-,22+,24+,25-,26-,27-,28-/m0/s1
InChIKey XAEUKOBJPRGERY-RGGIALPMSA-N
Formula C28H38O7
HBA 7
HBD 4
MW 486.61
Rotatable Bonds 2
TPSA 124.29
LogP 2.51
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 486.26
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 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]
Pubchem: 163005443
Nmrshiftdb2: 70111554

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 486.61 g/mol

Structure

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

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)
-5.19
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
78.45
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
3.75
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.92
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.06
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.53
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
-250.31
Rat (Acute)
3.96
Rat (Chronic Oral)
2.4
Fathead Minnow
4.05
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
482.34
Hydration Free Energy
-3.18
Log(D) at pH=7.4
2.43
Log(P)
2.22
Log S
-3.44
Log(Vapor Pressure)
-10.01
Melting Point
241.66
pKa Acid
6.04
pKa Basic
5.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8219
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8219
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7888
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7888
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7610
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7610
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7530
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7530
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7477
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7477
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7366
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7366
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7331
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7331
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7287
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7287
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7186
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7186

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