17alpha-hydroxycabralealactone - Compound Card

17alpha-hydroxycabralealactone

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17alpha-hydroxycabralealactone

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dammarane Triterpenoid
Canonical Smiles O=C1CC[C@@](O1)(C)[C@@]1(O)CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C
InChI InChI=1S/C27H42O4/c1-22(2)17-9-13-24(4)18(23(17,3)12-10-20(22)28)7-8-19-25(24,5)15-16-27(19,30)26(6)14-11-21(29)31-26/h17-19,30H,7-16H2,1-6H3/t17-,18+,19-,23-,24+,25+,26-,27+/m0/s1
InChIKey LTEAFAQTORTAOW-JHKVIMLZSA-N
Formula C27H42O4
HBA 4
HBD 1
MW 430.63
Rotatable Bonds 1
TPSA 63.6
LogP 5.45
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 430.31
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: 102066396
Nmrshiftdb2: 70083756

No compound-protein relationship available.

Structure

SMILES: O=C1CCC(O1)C2CCC(C23)C4C(CC3)C5C(CC4)CC(=O)CC5

Level: 1

Mol. Weight: 430.63 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(=O)C4

Level: 0

Mol. Weight: 430.63 g/mol

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 430.63 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.39
Plasma Protein Binding
77.84
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.28
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.08
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.95
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-44.87
Rat (Acute)
1.93
Rat (Chronic Oral)
1.43
Fathead Minnow
3.92
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
476.89
Hydration Free Energy
-3.45
Log(D) at pH=7.4
4.09
Log(P)
4.03
Log S
-5.84
Log(Vapor Pressure)
-8.25
Melting Point
240.55
pKa Acid
9.41
pKa Basic
6.62
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 0.8416
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8416
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8344
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8344
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8122
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8122
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7562
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7562
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7493
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7493
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7242
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7242
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7216
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7216
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7209
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7209

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