2-hydroxy-6-deacetoxyswietenine - Compound Card

2-hydroxy-6-deacetoxyswietenine

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2-hydroxy-6-deacetoxyswietenine

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)C[C@H]1C(C)(C)C(OC(=O)/C(=C/C)/C)[C@]2(C(=O)[C@]1(C)C1CC[C@@]3(C(C1=C2)CC(=O)O[C@H]3c1ccoc1)C)O
InChI InChI=1S/C32H40O9/c1-8-17(2)26(35)41-28-29(3,4)22(14-23(33)38-7)31(6)20-9-11-30(5)21(19(20)15-32(28,37)27(31)36)13-24(34)40-25(30)18-10-12-39-16-18/h8,10,12,15-16,20-22,25,28,37H,9,11,13-14H2,1-7H3/b17-8+/t20?,21?,22-,25-,28?,30+,31+,32-/m0/s1
InChIKey JJTOVDGWVPPWNZ-XTFJBBBGSA-N
Formula C32H40O9
HBA 9
HBD 1
MW 568.66
Rotatable Bonds 5
TPSA 129.34
LogP 4.64
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 568.27
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Swietenia mahogani Meliaceae Plantae 459165

Showing of synonyms

  • Abdelgaleil SA, Doe M, et al. (2013). Rings B,D-seco limonoid antifeedants from Swietenia mahogani. Phytochemistry,2013,96,312-317. [View] [PubMed]
Pubchem: 162917518
Nmrshiftdb2: 70038168

No compound-protein relationship available.

Structure

SMILES: c1occc1C2OC(=O)CC3C2CCC(C3=4)C5C(=O)C(C4)CCC5

Level: 1

Mol. Weight: 568.66 g/mol

Structure

SMILES: C1CCC(C2)C(=O)C1C(C=23)CCC4C3CC(=O)OC4

Level: 0

Mol. Weight: 568.66 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 568.66 g/mol

Antifeedant

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.800
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.070
Plasma Protein Binding
86.26
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
Inhibitor

Excretion

Clearance
11.100
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.160
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.810
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
-5257.480
Rat (Acute)
3.950
Rat (Chronic Oral)
2.430
Fathead Minnow
17.830
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
397.630
Hydration Free Energy
-2.870
Log(D) at pH=7.4
3.990
Log(P)
3.78
Log S
-5.55
Log(Vapor Pressure)
-9.61
Melting Point
231.87
pKa Acid
6.84
pKa Basic
3.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8754
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8754
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8429
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8429
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8420
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8420
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8338
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8338
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8333
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8333
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8187
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8187
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8139
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8139
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7896
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7896
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7811
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7811
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7770
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7770
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7738
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7738
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7736
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7736
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7687
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7687
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7652
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7652
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7621
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7621
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7610
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7610
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7590
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7590
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7587
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7587
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7584
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7584
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7523
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7523
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7513
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7513
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7499
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7499
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7433
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7433
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7396
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7396
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7381
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7381
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7366
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7366
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7362
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7362
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7356
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7356
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7336
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7336
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7323
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7323
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7300
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7300
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7286
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7286
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7262
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7262
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7256
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7256
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7228
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7228
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7228
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7228
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7217
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7217
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 2 0.7212
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 2 0.7212
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7201
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7201
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7195
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7195
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7184
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7184
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7177
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7177
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7161
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7161
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7160
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7160
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7159
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7159
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7148
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7148
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7148
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7148
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7111
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7111
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7104
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7104
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7101
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7101
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7077
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7077
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7061
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7061
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7055
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7055
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7049
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7049
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7041
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7041
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7040
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7040
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7036
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7036
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7024
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7024
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 2 0.7004
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7004
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7004
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 2 0.7004
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7003
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7003

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