3'-epi-afroside - Compound Card

3'-epi-afroside

Select a section from the left sidebar

3'-epi-afroside

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Glycoside
    • Subclass: Cardenolide Glycoside
Canonical Smiles C[C@@H]1C[C@H](O)[C@]2([C@@H](O1)O[C@H]1[C@H](O2)C[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)[C@H](O)C[C@@H]2C1=CC(=O)OC1)C)C)O
InChI InChI=1S/C29H42O9/c1-14-8-23(31)29(34)25(36-14)37-20-10-16-4-5-18-17(26(16,2)12-21(20)38-29)6-7-27(3)19(11-22(30)28(18,27)33)15-9-24(32)35-13-15/h9,14,16-23,25,30-31,33-34H,4-8,10-13H2,1-3H3/t14-,16+,17+,18-,19-,20-,21-,22-,23+,25+,26+,27-,28-,29+/m1/s1
InChIKey HNOFNBVWCFKUEQ-GMPNGYBSSA-N
Formula C29H42O9
HBA 9
HBD 4
MW 534.65
Rotatable Bonds 1
TPSA 134.91
LogP 1.79
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 534.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Gomphocarpus sinaicus Apocynaceae Plantae 2291033
2 Gomphocarpus sinaicus Apocynaceae Plantae 2291033

Showing of synonyms

  • El-Askary H, Holzl J, et al. (1993). Cardenolide glycosides with doubly linked sugars from Gomphocarpus sinaicus. Phytochemistry,1993,34(5),1399-1402. [View]
  • Abdel-Azim NS, Hammouda FM, et al. (1996). Re-investigation of the cardenolide glycosides from Gomphocarpus sinaicus. Phytochemistry,1996,42(2),523-529. [View]
Pubchem: 14134967
Nmrshiftdb2: 70013530

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7

Level: 1

Mol. Weight: 534.65 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CC5C(C4)OC6C(O5)CCCO6

Level: 0

Mol. Weight: 534.65 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 534.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.53
Human Oral Bioavailability 20%
Non-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
-0.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
70.0
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
2.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.35
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-2.97
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.94
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Toxic
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2469.12
Rat (Acute)
4.17
Rat (Chronic Oral)
2.17
Fathead Minnow
7.22
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
463.38
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.21
Log(P)
1.38
Log S
-3.76
Log(Vapor Pressure)
-10.75
Melting Point
244.39
pKa Acid
6.8
pKa Basic
6.1

No predicted protein targets found for this compound.

Download SDF