12beta-acetoxy-1(2),22(23) tetradehydrocabralealactone - Compound Card

12beta-acetoxy-1(2),22(23) tetradehydrocabralealactone

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12beta-acetoxy-1(2),22(23) tetradehydrocabralealactone

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dammarane Triterpene
Canonical Smiles CC(=O)OC1(CCC2(C1CCC3C2(CCC4C3(C=CC(=O)C4(C)C)C)C)C)C5(C=CC(=O)O5)C
InChI InChI=1S/C29H40O5/c1-18(30)33-29(28(7)15-12-23(32)34-28)17-16-27(6)21(29)9-8-20-25(4)13-11-22(31)24(2,3)19(25)10-14-26(20,27)5/h11-13,15,19-21H,8-10,14,16-17H2,1-7H3
InChIKey IASRRVSSAUBZNO-UHFFFAOYSA-N
Formula C29H40O5
HBA 5
HBD 0
MW 468.63
Rotatable Bonds 2
TPSA 69.67
LogP 5.57
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 arabica Capparaceae Plantae 511509

Showing of synonyms

  • Ladhari A, Tufano I, et al. (2020). Influence of new effective allelochemicals on the distribution of Cleome arabica L. community in nature. Natural product research, 2020, 34(6), 773-781. [View] [PubMed]

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

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.75
Plasma Protein Binding
39.65
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
9.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.45
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.05
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
-157.09
Rat (Acute)
1.91
Rat (Chronic Oral)
1.63
Fathead Minnow
4.91
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
473.66
Hydration Free Energy
-2.73
Log(D) at pH=7.4
4.1
Log(P)
4.21
Log S
-6.3
Log(Vapor Pressure)
-7.31
Melting Point
216.42
pKa Acid
9.05
pKa Basic
5.6
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 0.9021
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8777
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8572
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8414
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8276
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8245
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8190
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7797
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7769
Abscisic acid receptor PYL9 Q5Z8S0 PYL9_ORYSJ Oryza sativa subsp. japonica 4 0.7621
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7318
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7304
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.7293
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 4 0.7233
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7179
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 4 0.7083
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7055

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