16-acetoxy-11-hydroxyoctadeca-17-ene-12,14-diynyl ethanoate - Compound Card

16-acetoxy-11-hydroxyoctadeca-17-ene-12,14-diynyl ethanoate

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16-acetoxy-11-hydroxyoctadeca-17-ene-12,14-diynyl ethanoate

Structure
Zoomed Structure
  • Family: Plantae - Araliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Polyacetylene
Canonical Smiles C=CC(OC(=O)C)C#CC#CC(CCCCCCCCCCOC(=O)C)O
InChI InChI=1S/C22H32O5/c1-4-22(27-20(3)24)17-13-12-16-21(25)15-11-9-7-5-6-8-10-14-18-26-19(2)23/h4,21-22,25H,1,5-11,14-15,18H2,2-3H3
InChIKey AVKOLTWNMGUSAT-UHFFFAOYSA-N
Formula C22H32O5
HBA 5
HBD 1
MW 376.49
Rotatable Bonds 13
TPSA 72.83
LogP 3.55
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 376.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cussonia zimmermannii Araliaceae Plantae 1899105

Showing of synonyms

  • Senn M, Gunzenhauser S, et al. (2007). Antiprotozoal polyacetylenes from the Tanzanian medicinal plant Cussonia zimmermannii. Journal of Natural Products,2007,70(10),1565-1569. [View] [PubMed]
Pubchem: 11632231
Nmrshiftdb2: 70126533

No compound-protein relationship available.

No scaffolds available.

Antiprotozoal

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.24
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
11.04
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.83
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.18
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.23
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.42
Rat (Acute)
2.39
Rat (Chronic Oral)
2.07
Fathead Minnow
4.44
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
386.51
Hydration Free Energy
-4.46
Log(D) at pH=7.4
3.38
Log(P)
5.32
Log S
-4.45
Log(Vapor Pressure)
-7.05
Melting Point
8.18
pKa Acid
8.54
pKa Basic
2.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
1,4-alpha-glucan branching enzyme GlgB A7ZSW5 GLGB_ECO24 Escherichia coli O139:H28 3 0.9447
1,4-alpha-glucan branching enzyme GlgB A7ZSW5 GLGB_ECO24 Escherichia coli O139:H28 3 0.9447
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.8013
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.8013
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7073
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7073

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