Epigouanic acid A - Compound Card

Epigouanic acid A

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Epigouanic acid A

Structure
Zoomed Structure
  • Family: Plantae - Vitaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ceanothane Triterpene
Canonical Smiles OC[C@H]1CC(C2[C@@]1(C)C1CCC3[C@@]([C@@]1(CC2)C)(CO)CC[C@@]1(C3[C@@H](CC1)C(=C)C)C(=O)O)(C)C
InChI InChI=1S/C30H48O4/c1-18(2)20-9-12-29(25(33)34)13-14-30(17-32)21(24(20)29)7-8-23-27(30,5)11-10-22-26(3,4)15-19(16-31)28(22,23)6/h19-24,31-32H,1,7-17H2,2-6H3,(H,33,34)/t19-,20+,21?,22?,23?,24?,27-,28+,29+,30+/m1/s1
InChIKey KRZWBMKZCTWIFL-MFXIJAKQSA-N
Formula C30H48O4
HBA 3
HBD 3
MW 472.71
Rotatable Bonds 4
TPSA 77.76
LogP 5.92
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 472.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Cyphostemma adenocaule Vitaceae Plantae 1236437

Showing of synonyms

  • Chouna JR, Nardella F, et al. (2016). Ceanothane-type triterpenoids from Cyphostemma adenocaule.. Archives of pharmacal research,2016. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C5C(CCC5)CCC34

Level: 0

Mol. Weight: 472.71 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.880
Plasma Protein Binding
78.81
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
3.860
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.130
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.520
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.410
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-198.640
Rat (Acute)
2.540
Rat (Chronic Oral)
2.510
Fathead Minnow
4.020
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
464.360
Hydration Free Energy
-2.490
Log(D) at pH=7.4
3.850
Log(P)
4.83
Log S
-5.71
Log(Vapor Pressure)
-9.86
Melting Point
262.01
pKa Acid
5.28
pKa Basic
8.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8028
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7653
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7385
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7319
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7140

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