6-O-acetyl-2-hydroxyswietenin - Compound Card

6-O-acetyl-2-hydroxyswietenin

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6-O-acetyl-2-hydroxyswietenin

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)[C@@H]([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)OC(=O)C
InChI InChI=1S/C34H42O11/c1-9-17(2)27(37)45-30-31(4,5)25(24(28(38)41-8)43-18(3)35)33(7)21-10-12-32(6)22(20(21)15-34(30,40)29(33)39)14-23(36)44-26(32)19-11-13-42-16-19/h9,11,13,15-16,21-22,24-26,30,40H,10,12,14H2,1-8H3/b17-9+/t21?,22?,24-,25+,26+,30?,32-,33-,34+/m1/s1
InChIKey KQJNENMKRYMNJO-HDEPKMHESA-N
Formula C34H42O11
HBA 11
HBD 1
MW 626.7
Rotatable Bonds 6
TPSA 155.64
LogP 4.19
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 626.27
Number of Lipinski Rule Violations 2
# 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: 162949087
Nmrshiftdb2: 70038170

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 626.7 g/mol

Structure

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

Level: 0

Mol. Weight: 626.7 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 626.7 g/mol

Antifeedant

Absorption

Caco-2 (logPapp)
-5.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
14.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.730
Plasma Protein Binding
88.34
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
11.230
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
0.060
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.030
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
-29264.770
Rat (Acute)
4.020
Rat (Chronic Oral)
2.560
Fathead Minnow
58.340
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
294.870
Hydration Free Energy
-2.920
Log(D) at pH=7.4
3.570
Log(P)
3.64
Log S
-5.38
Log(Vapor Pressure)
-15.56
Melting Point
238.54
pKa Acid
6.21
pKa Basic
2.6
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 0.8588
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8588
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8515
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8515
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8439
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8439
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8421
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8421
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8353
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8353
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8210
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8210
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8113
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8113
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8046
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8046
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7914
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7914
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7822
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7822
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7792
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7792
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7789
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7789
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7761
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7761
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7747
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7747
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7678
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7678
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7628
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7628
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7608
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7608
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7580
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7580
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7553
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7553
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7551
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7551
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7548
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7548
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7509
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7509
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7502
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7502
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7475
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7475
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7453
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7453
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7391
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7391
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7384
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7384
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7381
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7381
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7328
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7328
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7315
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7315
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7286
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7286
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7270
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7270
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7252
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7252
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7234
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7234
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7233
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7233
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7226
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7226
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7224
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7224
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7192
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7192
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7181
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7181
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7158
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7158
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7147
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7147
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7127
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7127
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7123
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7123
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7104
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7104
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7090
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7090
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7082
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7082
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7052
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7052
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7019
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7019
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7017
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7017
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7016
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7016
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7010
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7010
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
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7006
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7006

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