3-O-acetyl-12beta-acetoxy-17alpha-hydroxycabraleahydroxylactone - Compound Card

3-O-acetyl-12beta-acetoxy-17alpha-hydroxycabraleahydroxylactone

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3-O-acetyl-12beta-acetoxy-17alpha-hydroxycabraleahydroxylactone

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dammarane Triterpenoid
Canonical Smiles CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@H](C([C@@H]3CC[C@]2([C@]2([C@H]1[C@](O)(CC2)[C@]1(C)CCC(=O)O1)C)C)(C)C)OC(=O)C
InChI InChI=1S/C31H48O7/c1-18(32)36-20-17-22-27(5)12-10-23(37-19(2)33)26(3,4)21(27)9-13-28(22,6)29(7)15-16-31(35,25(20)29)30(8)14-11-24(34)38-30/h20-23,25,35H,9-17H2,1-8H3/t20-,21+,22-,23-,25+,27+,28-,29-,30+,31-/m1/s1
InChIKey HZLWOGKTVDZVAN-DZNQXZFQSA-N
Formula C31H48O7
HBA 7
HBD 1
MW 532.72
Rotatable Bonds 3
TPSA 99.13
LogP 5.36
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 532.34
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Cleome africana Capparaceae Plantae 860685
2 Cleome africana Capparaceae Plantae 860685

Showing of synonyms

  • Nagaya H, Tobita Y, et al. (1997). Cytotoxic triterpenes from Cleome africana. Phytochemistry, 1997, 44(6), 1115-9. [View] [PubMed]
  • Nagaya H, Tobita Y, et al. (1997). Cytotoxic triterpenes from Cleome africana.. Phytochemistry,1997,44(6),1115-1119. [View] [PubMed]
Pubchem: 102066397
Nmrshiftdb2: 70083763

No compound-protein relationship available.

Structure

SMILES: O=C1CCC(O1)C2CCC(C23)C4C(CC3)C5C(CC4)CCCC5

Level: 1

Mol. Weight: 532.72 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 532.72 g/mol

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 532.72 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.07
Plasma Protein Binding
85.4
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.71
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.45
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.41
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
-856.14
Rat (Acute)
2.34
Rat (Chronic Oral)
1.66
Fathead Minnow
4.0
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
494.83
Hydration Free Energy
-2.86
Log(D) at pH=7.4
3.74
Log(P)
4.45
Log S
-6.01
Log(Vapor Pressure)
-8.62
Melting Point
225.98
pKa Acid
9.52
pKa Basic
5.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9482
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9482
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8284
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8284
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7661
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7661
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7470
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7470
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7433
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7433
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7417
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7417
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7263
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7263
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7217
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7217
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7204
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7204

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