12beta-acetoxyl(2),22(23)-tetradehydrocabralea-lactone - Compound Card

12beta-acetoxyl(2),22(23)-tetradehydrocabralea-lactone

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12beta-acetoxyl(2),22(23)-tetradehydrocabralea-lactone

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dammarane Triterpenoid
Canonical Smiles CC(=O)O[C@@H]1CC2[C@@]3(C)C=CC(=O)C(C3CC[C@]2([C@]2(C1C(CC2)[C@]1(C)C=CC(=O)O1)C)C)(C)C
InChI InChI=1S/C29H40O5/c1-17(30)33-19-16-21-26(4)12-10-22(31)25(2,3)20(26)9-14-27(21,5)28(6)13-8-18(24(19)28)29(7)15-11-23(32)34-29/h10-12,15,18-21,24H,8-9,13-14,16H2,1-7H3/t18?,19-,20?,21?,24?,26+,27-,28-,29+/m1/s1
InChIKey HHADFXKLJQYGKX-KZEHPBANSA-N
Formula C29H40O5
HBA 5
HBD 0
MW 468.63
Rotatable Bonds 2
TPSA 69.67
LogP 5.43
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 468.29
Number of Lipinski Rule Violations 1
# 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: 162927960

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(O1)C2CCC(C23)C4C(CC3)C5C(CC4)CC(=O)C=C5

Level: 1

Mol. Weight: 468.63 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3C=CC(=O)C4

Level: 0

Mol. Weight: 468.63 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 468.63 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.77
Plasma Protein Binding
82.2
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
8.54
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.41
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.16
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.23
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-168.49
Rat (Acute)
2.14
Rat (Chronic Oral)
1.64
Fathead Minnow
4.26
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
488.08
Hydration Free Energy
-2.82
Log(D) at pH=7.4
4.2
Log(P)
4.01
Log S
-6.09
Log(Vapor Pressure)
-7.64
Melting Point
225.76
pKa Acid
9.03
pKa Basic
5.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8370
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8370
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7801
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7801
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7760
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7760
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7490
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7490

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