3-O-acetyl-12beta-acetoxy-25-O-ethylcleocarpanol - Compound Card

3-O-acetyl-12beta-acetoxy-25-O-ethylcleocarpanol

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3-O-acetyl-12beta-acetoxy-25-O-ethylcleocarpanol

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dammarane Triterpenoid
Canonical Smiles CCOC([C@]12CC[C@](O1)([C@@]1(O2)CC[C@@]2([C@@H]1[C@H](OC(=O)C)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)OC(=O)C)C)C)(C)C
InChI InChI=1S/C36H58O7/c1-12-39-30(6,7)36-20-18-34(11,42-36)35(43-36)19-17-33(10)28(35)24(40-22(2)37)21-26-31(8)15-14-27(41-23(3)38)29(4,5)25(31)13-16-32(26,33)9/h24-28H,12-21H2,1-11H3/t24-,25+,26-,27-,28+,31+,32-,33-,34+,35-,36-/m1/s1
InChIKey QVKYLQCSMQSINY-SAAGHGFTSA-N
Formula C36H58O7
HBA 7
HBD 0
MW 602.85
Rotatable Bonds 5
TPSA 80.29
LogP 7.38
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 602.42
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Cleome africana Capparaceae Plantae 860685

Showing of synonyms

  • Nagaya H, Tobita Y, et al. (1997). Cytotoxic triterpenes from Cleome africana.. Phytochemistry,1997,44(6),1115-1119. [View] [PubMed]
Pubchem: 102066547
Nmrshiftdb2: 70083773

No compound-protein relationship available.

Structure

SMILES: O1C(O2)CCC2C13C4C(CC3)C5C(CC4)C6C(CC5)CCCC6

Level: 0

Mol. Weight: 602.85 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
4.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.16
Plasma Protein Binding
98.6
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Non-Inhibitor

Excretion

Clearance
7.16
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.08
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.36
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.11
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-10565.67
Rat (Acute)
2.0
Rat (Chronic Oral)
1.4
Fathead Minnow
28.33
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
323.4
Hydration Free Energy
-2.91
Log(D) at pH=7.4
5.93
Log(P)
6.94
Log S
-7.4
Log(Vapor Pressure)
-11.01
Melting Point
195.47
pKa Acid
11.27
pKa Basic
6.59
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 0.8133
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7336
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7336
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7275
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7275
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7235
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7235

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