7-deacetoxy-7-oxogedunin - Compound Card

7-deacetoxy-7-oxogedunin

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7-deacetoxy-7-oxogedunin

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles O=C1O[C@@H](c2ccoc2)[C@]2([C@]3([C@@H]1O3)[C@]1(C)C(=O)C[C@@H]3[C@](C1CC2)(C)C=CC(=O)C3(C)C)C
InChI InChI=1S/C26H30O6/c1-22(2)16-12-18(28)25(5)15(23(16,3)9-7-17(22)27)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)32-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15?,16-,19-,20+,23+,24-,25-,26+/m0/s1
InChIKey PMISPNORJONCHB-LLWDQIFWSA-N
Formula C26H30O6
HBA 6
HBD 0
MW 438.52
Rotatable Bonds 1
TPSA 86.11
LogP 4.2
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 438.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Swietenia mahogani Meliaceae Plantae 459165
2 Swietenia mahogani Meliaceae Plantae 459165
3 Ekebergia capensis Meliaceae Plantae 124949

Showing of synonyms

  • Murata T, Miyase T, et al. (2008). Antiplasmodial triterpenoids from Ekebergia capensis.. Journal of Natural Products,2008,71(2),167-174. [View] [PubMed]
  • Abdelgaleil SA, Doe M, et al. (2013). Rings B,D-seco limonoid antifeedants from Swietenia mahogani. Phytochemistry,2013,96,312-317. [View] [PubMed]
  • Abdelgaleil SA, Doe M, et al. (2006). Rings B,D-seco limonoids from the leaves of Swietenia mahogani. Phytochemistry,2006,67(5),452-458. [View] [PubMed]
Pubchem: 71300386
Nmrshiftdb2: 70019872
CPRiL: 415930
Structure

SMILES: c1occc1C(OC(=O)C(C234)O4)C3CCC5C2C(=O)CC6C5C=CC(=O)C6

Level: 1

Mol. Weight: 438.52 g/mol

Structure

SMILES: C123C(O3)C(=O)OCC2CCC4C1C(=O)CC5C4C=CC(=O)C5

Level: 0

Mol. Weight: 438.52 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 438.52 g/mol

Anti-plasmodial
Antifeedant

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.79
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
56.27
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.52
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.89
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.19
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.54
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-112.3
Rat (Acute)
3.2
Rat (Chronic Oral)
1.86
Fathead Minnow
3.95
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
476.93
Hydration Free Energy
-2.59
Log(D) at pH=7.4
3.29
Log(P)
2.69
Log S
-5.02
Log(Vapor Pressure)
-8.88
Melting Point
283.3
pKa Acid
4.24
pKa Basic
3.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8051
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8051
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7820
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7820
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7761
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7761
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7639
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7639
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7632
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7632
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7610
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7610
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7357
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7357
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7330
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7330
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7319
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7319
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7222
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7222
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7121
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7121
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7067
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7067
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7064
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7064
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7050
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7050
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7008
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7008

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