Euscaphic acid - Compound Card

Euscaphic acid

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Euscaphic acid

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Pentacyclic Triterpenoid
Canonical Smiles O[C@@H]1C[C@@]2(C)[C@H](C([C@@H]1O)(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C
InChI InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1
InChIKey OXVUXGFZHDKYLS-QUFHAEKXSA-N
Formula C30H48O5
HBA 4
HBD 4
MW 488.71
Rotatable Bonds 1
TPSA 97.99
LogP 5.18
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 488.35
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Myrianthus arboreus Cecropiaceae Plantae 1781621
2 Plectranthus alpinus Lamiaceae Plantae 2485368

Showing of synonyms

  • Ngounou FN, Lontsi D, et al. (1990). Myrianthiphyllin, The First Lignan Cinnamate from Myrianthus arboreus.. Planta medica,1990, 56(2), 227-229. [View] [PubMed]
  • Djuidje FEK, Songue JL, et al. (2021). Triterpenoids and Flavones of Cameroonian Plectranthus alpinus. Chem Nat Compd, 2021, 57, 982–984. [View]
Pubchem: 471426
Kegg Ligand: C17890
Chebi: 67914
Nmrshiftdb2: 60023873
Metabolights: MTBLC67914
Bindingdb: 50543759
CPRiL: 13976
Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 488.71 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.19
Plasma Protein Binding
89.12
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
2.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.98
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.13
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.95
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
-179.86
Rat (Acute)
2.67
Rat (Chronic Oral)
2.41
Fathead Minnow
3.89
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
491.62
Hydration Free Energy
-3.01
Log(D) at pH=7.4
3.25
Log(P)
4.68
Log S
-5.03
Log(Vapor Pressure)
-10.15
Melting Point
233.51
pKa Acid
4.71
pKa Basic
8.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7096

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