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6-O-deacetylsecomahoganin
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | COC(=O)[C@]1(C)[C@H](CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1ccoc1)C)[C@@]1(C)C=CC(=O)C([C@@H]1CO)(C)C |
|---|---|
| InChI | InChI=1S/C27H34O8/c1-23(2)17(13-28)24(3,10-8-18(23)29)16-7-11-25(4)19(15-9-12-33-14-15)34-21(30)20-27(25,35-20)26(16,5)22(31)32-6/h8-10,12,14,16-17,19-20,28H,7,11,13H2,1-6H3/t16-,17+,19+,20-,24-,25+,26+,27-/m1/s1 |
| InChIKey | FRQQICZGMXISSV-LAMXMUIOSA-N |
| Formula | C27H34O8 |
| HBA | 8 |
| HBD | 1 |
| MW | 486.56 |
| Rotatable Bonds | 4 |
| TPSA | 115.57 |
| LogP | 3.39 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 486.23 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Swietenia mahogani | Meliaceae | Plantae | 459165 |
Showing of synonyms
6-O-deacetylsecomahoganin
No compound-protein relationship available.
SMILES: c1occc1C(OC(=O)C(C234)O4)C2CCC(C3)C(CC5)C=CC5=O
Level: 2
Mol. Weight: 486.56 g/mol
SMILES: C123C(O3)C(=O)OCC1CCC(C2)C(CC4)C=CC4=O
Level: 1
Mol. Weight: 486.56 g/mol
SMILES: C1CCCC2C(OC(=O)C(C123)O3)c4ccoc4
Level: 1
Mol. Weight: 486.56 g/mol
SMILES: C123C(O3)C(=O)OCC1CCCC2
Level: 0
Mol. Weight: 486.56 g/mol
SMILES: O=C1C=CCCC1
Level: 0
Mol. Weight: 486.56 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 486.56 g/mol
Antifeedant
Absorption
- Caco-2 (logPapp)
- -5.21
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.810
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.650
- Plasma Protein Binding
- 55.59
- 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
- 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
- 13.990
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.980
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.330
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.170
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- 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
- -351.590
- Rat (Acute)
- 4.360
- Rat (Chronic Oral)
- 2.010
- Fathead Minnow
- 4.030
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 474.990
- Hydration Free Energy
- -2.950
- Log(D) at pH=7.4
- 2.870
- Log(P)
- 2.65
- Log S
- -5.01
- Log(Vapor Pressure)
- -9.28
- Melting Point
- 204.08
- pKa Acid
- 4.99
- pKa Basic
- 3.34
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8578 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8578 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7945 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7945 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7928 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7928 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7796 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7796 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7786 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7786 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7635 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7635 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7462 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7462 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7432 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7432 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7413 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7413 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7392 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7392 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7386 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7386 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7375 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7375 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7357 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7357 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7318 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7318 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.7297 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.7297 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.7283 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.7283 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7271 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7271 |
| Cyclic AMP receptor protein | Q5SID7 | CRP_THET8 | Thermus thermophilus | 2 | 0.7242 |
| Cyclic AMP receptor protein | Q5SID7 | CRP_THET8 | Thermus thermophilus | 2 | 0.7242 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7221 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7221 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7195 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7195 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7171 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7171 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7170 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7170 |
| Alanine racemase | Q180W0 | Q180W0_CLOD6 | Clostridioides difficile | 2 | 0.7132 |
| Alanine racemase | Q180W0 | Q180W0_CLOD6 | Clostridioides difficile | 2 | 0.7132 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7129 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7129 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7123 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7123 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 2 | 0.7106 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 2 | 0.7106 |
| Adenosine kinase | Q9TVW2 | ADK_TOXGO | Toxoplasma gondii | 3 | 0.7070 |
| Adenosine kinase | Q9TVW2 | ADK_TOXGO | Toxoplasma gondii | 3 | 0.7070 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7046 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7046 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7045 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7045 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7044 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7044 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7030 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7030 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 2 | 0.7018 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 2 | 0.7018 |