14beta,15beta-dihydroxy-pregn-4-ene-3,20-dione-15beta-D-glucopyranoside - Compound Card

14beta,15beta-dihydroxy-pregn-4-ene-3,20-dione-15beta-D-glucopyranoside

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14beta,15beta-dihydroxy-pregn-4-ene-3,20-dione-15beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Pregnane Glycoside
Canonical Smiles OCC1OC(O[C@@H]2[C@@H](C[C@@]3([C@@]2(O)[C@@H]2CCC4=CC(=O)CC[C@@]4([C@H]2CC3)C)C)C(=O)C)C(C(C1O)O)O
InChI InChI=1S/C27H40O9/c1-13(29)16-11-25(2)8-7-17-18(5-4-14-10-15(30)6-9-26(14,17)3)27(25,34)23(16)36-24-22(33)21(32)20(31)19(12-28)35-24/h10,16-24,28,31-34H,4-9,11-12H2,1-3H3/t16-,17-,18+,19?,20?,21?,22?,23+,24?,25+,26-,27+/m0/s1
InChIKey WTZCIGSAQULEEF-ZXWHDBPWSA-N
Formula C27H40O9
HBA 9
HBD 5
MW 508.61
Rotatable Bonds 4
TPSA 153.75
LogP 0.63
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 508.27
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Solenostemma argel Apocynaceae Plantae 219273

Showing of synonyms

  • Ounaissia K, Pertuit D, et al. (2016). New pregnane and phenolic glycosides from Solenostemma argel. Fitoterapia, 2016, 114, 98-104. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC2CCC(C23)CCC4C3CCC=5C4CCC(=O)C5

Level: 1

Mol. Weight: 508.61 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(=O)C4

Level: 0

Mol. Weight: 508.61 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 508.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.0
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
74.89
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
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
-0.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.3
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.04
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-506.47
Rat (Acute)
3.45
Rat (Chronic Oral)
3.33
Fathead Minnow
3.5
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
519.53
Hydration Free Energy
-3.09
Log(D) at pH=7.4
1.75
Log(P)
0.28
Log S
-2.31
Log(Vapor Pressure)
-12.43
Melting Point
200.06
pKa Acid
6.79
pKa Basic
6.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8105
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7289
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7258
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7051

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