18-nor-4alpha-carbomethoxy-11beta-acetoxy-12alpha-(2-methylbutanoyloxy)-14,15-deoxyhavanensin-1-acetate - Compound Card

18-nor-4alpha-carbomethoxy-11beta-acetoxy-12alpha-(2-methylbutanoyloxy)-14,15-deoxyhavanensin-1-acetate

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18-nor-4alpha-carbomethoxy-11beta-acetoxy-12alpha-(2-methylbutanoyloxy)-14,15-deoxyhavanensin-1-acetate

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles CCC(C(=O)O[C@H]1[C@H](OC(=O)C)C2[C@@]3(C)[C@@H](OC(=O)C)C[C@H]([C@@](C3C[C@H]([C@]2(C2[C@]1(C)[C@@H](CC2)c1ccoc1)C)O)(C)OC(=O)C)O)C
InChI InChI=1S/C36H52O11/c1-10-18(2)32(42)46-31-29(45-20(4)38)30-34(7,24-12-11-23(33(24,31)6)22-13-14-43-17-22)26(40)15-25-35(30,8)28(44-19(3)37)16-27(41)36(25,9)47-21(5)39/h13-14,17-18,23-31,40-41H,10-12,15-16H2,1-9H3/t18?,23-,24?,25?,26+,27+,28-,29+,30?,31-,33-,34+,35+,36-/m0/s1
InChIKey OQOLKKFJTDGKEH-NZPSDZLNSA-N
Formula C36H52O11
HBA 11
HBD 2
MW 660.8
Rotatable Bonds 7
TPSA 158.8
LogP 4.71
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 660.35
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Turraea floribunda Meliaceae Plantae 992802

Showing of synonyms

  • Torto B, Bentley MD, et al. (1995). Limonoids from Turraea floribunda.. Phytochemistry,1995,40(1),239-243. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1occc1C2CCC(C23)C4C(CC3)C5C(CC4)CCCC5

Level: 1

Mol. Weight: 660.8 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 660.8 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 660.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
35.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
91.99
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
7.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.02
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
8.21
Micronucleos
Toxic
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
-68392.71
Rat (Acute)
4.98
Rat (Chronic Oral)
2.51
Fathead Minnow
100.87
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
3492.45
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.31
Log(P)
4.7
Log S
-5.19
Log(Vapor Pressure)
-122.47
Melting Point
175.49
pKa Acid
8.19
pKa Basic
2.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 4 0.8865
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 4 0.8865
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8575
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8575
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7888
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7888
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7783
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7783
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7744
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7744
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7614
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7614
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7428
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7428
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7297
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7297
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7293
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7293
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7235
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7235
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7041
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7041

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