1(12),22(23)-tetradehydrocabralealactone - Compound Card

1(12),22(23)-tetradehydrocabralealactone

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1(12),22(23)-tetradehydrocabralealactone

Structure
Zoomed Structure
  • Family: Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dammarane Triterpenoid
Canonical Smiles O=C1C=C[C@@](O1)(C)C1CC[C@@]2(C1CCC1[C@@]2(C)CCC2[C@]1(C)C=CC(=O)C2(C)C)C
InChI InChI=1S/C27H38O3/c1-23(2)19-10-15-26(5)20(24(19,3)13-11-21(23)28)8-7-17-18(9-14-25(17,26)4)27(6)16-12-22(29)30-27/h11-13,16-20H,7-10,14-15H2,1-6H3/t17?,18?,19?,20?,24-,25+,26+,27-/m0/s1
InChIKey UNLHOZSQJSDBQS-DDLHVKBFSA-N
Formula C27H38O3
HBA 3
HBD 0
MW 410.6
Rotatable Bonds 1
TPSA 43.37
LogP 5.89
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 410.28
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: 162961478

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: 326.44 g/mol

Structure

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

Level: 0

Mol. Weight: 244.38 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 84.07 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.92
Plasma Protein Binding
78.28
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.93
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.44
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.58
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
-31.38
Rat (Acute)
2.05
Rat (Chronic Oral)
1.32
Fathead Minnow
4.27
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
461.7
Hydration Free Energy
-3.99
Log(D) at pH=7.4
4.7
Log(P)
4.68
Log S
-6.25
Log(Vapor Pressure)
-7.38
Melting Point
223.77
pKa Acid
9.31
pKa Basic
6.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8133
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8123
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8123
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8033
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8033
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7714
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7714
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7563
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7563
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7146
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7146
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7125
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7125
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7024
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7024

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