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Assafoetidnol B
- Family: Plantae - Apiaceae
- Kingdom: Plantae
-
Class: Coumarin
- Subclass: Sesquiterpene Coumarin
| Canonical Smiles | CC(=O)O[C@H]1CC[C@@]2([C@@H](C1(C)C)[C@H](O)[C@H](C(=C)[C@@H]2COc1ccc2c(c1)oc(=O)cc2)O)C |
|---|---|
| InChI | InChI=1S/C26H32O7/c1-14-18(13-31-17-8-6-16-7-9-21(28)33-19(16)12-17)26(5)11-10-20(32-15(2)27)25(3,4)24(26)23(30)22(14)29/h6-9,12,18,20,22-24,29-30H,1,10-11,13H2,2-5H3/t18-,20-,22-,23+,24+,26-/m0/s1 |
| InChIKey | CKPWNMFJQJVNER-DVITTYBWSA-N |
| Formula | C26H32O7 |
| HBA | 7 |
| HBD | 2 |
| MW | 456.54 |
| Rotatable Bonds | 4 |
| TPSA | 106.2 |
| LogP | 3.45 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.54 |
| Exact Mass | 456.21 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ferula assa-foetida | Apiaceae | Plantae | 52471 |
Showing of synonyms
Assafoetidnol B
403642-11-5
UNII-18842MRL1M
18842MRL1M
[(2S,4aS,5R,7S,8S,8aS)-7,8-dihydroxy-1,1,4a-trimethyl-6-methylidene-5-[(2-oxochromen-7-yl)oxymethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalen-2-yl] acetate
DTXSID30193353
(2R,4aR,5S,7R,8R,8aR)-7,8-dihydroxy-1,1,4a-trimethyl-6-methylene-5-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}decahydronaphthalen-2-yl rel-acetate
2H-1-BENZOPYRAN-2-ONE, 7-(((1R,3S,4S,4AS,6S,8AS)-6-(ACETYLOXY)DECAHYDRO-3,4-DIHYDROXY-5,5,8A-TRIMETHYL-2-METHYLENE-1-NAPHTHALENYL)METHOXY)-
2H-1-benzopyran-2-one, 7-[[(1R,3S,4S,4aS,6S,8aS)-6-(acetyloxy)decahydro-3,4-dihydroxy-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methoxy]-
Acetic acid 7,8-dihydroxy-1,1,4a-trimethyl-6-methylene-5-(2-oxo-2H-chromen-7-yloxymethyl)-decahydro-naphthalen-2-yl ester
((2S,4aS,5R,7S,8S,8aS)-7,8-dihydroxy-1,1,4a-trimethyl-6-methylidene-5-((2-oxochromen-7-yl)oxymethyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalen-2-yl) acetate
(2R,4aR,5S,7R,8R,8aR)-7,8-dihydroxy-1,1,4a-trimethyl-6-methylene-5-(((2-oxo-2H-chromen-7-yl)oxy)methyl)decahydronaphthalen-2-yl rel-acetate
DTXCID40115844
Inchi=1/c26h32o7/c1-14-18(13-31-17-8-6-16-7-9-21(28)33-19(16)12-17)26(5)11-10-20(32-15(2)27)25(3,4)24(26)23(30)22(14)29/h6-9,12,18,20,22-24,29-30h,1,10-11,13h2,2-5h3/t18-,20-,22-,23+,24+,26-/m0/s
Q27251977
- El-Razek MHA, Ohta S, et al. (2001). Sesquiterpene coumarins from the roots of Ferula assa-foetida. Phytochemistry,2001,58(8),1289-1295. [View]
No compound-protein relationship available.
SMILES: C1CCCC(C12)CCC(=C)C2COc(cc3)cc(c34)oc(=O)cc4
Level: 1
Mol. Weight: 456.54 g/mol
SMILES: C=C(C1)CCC(C12)CCCC2
Level: 0
Mol. Weight: 456.54 g/mol
SMILES: c1cccc(c12)oc(=O)cc2
Level: 0
Mol. Weight: 456.54 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.91
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.61
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.25
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.89
- Plasma Protein Binding
- 88.66
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.51
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.17
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.05
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.98
- 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
- -87.43
- Rat (Acute)
- 4.07
- Rat (Chronic Oral)
- 1.94
- Fathead Minnow
- 4.03
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 482.36
- Hydration Free Energy
- -2.79
- Log(D) at pH=7.4
- 3.19
- Log(P)
- 3.44
- Log S
- -4.5
- Log(Vapor Pressure)
- -9.88
- Melting Point
- 165.93
- pKa Acid
- 6.6
- pKa Basic
- 5.39
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.9823 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.9823 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.9651 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.9651 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.9561 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.9561 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9534 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9534 |
| Metapyrocatechase | Q7WYF5 | Q7WYF5_9PSED | Pseudomonas alkylphenolica | 3 | 0.9464 |
| Metapyrocatechase | Q7WYF5 | Q7WYF5_9PSED | Pseudomonas alkylphenolica | 3 | 0.9464 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.9151 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.9151 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8733 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8733 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8546 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8546 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.8355 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.8355 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8346 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8346 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8301 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8301 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8260 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8260 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8144 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8144 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8092 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8092 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 2 | 0.8071 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 2 | 0.8071 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 2 | 0.7997 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 2 | 0.7997 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7903 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7903 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7885 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7885 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7827 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7827 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7813 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7813 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7772 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7772 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7767 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7767 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7748 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7748 |
| cGMP-dependent protein kinase 1 | P00516 | KGP1_BOVIN | Bos taurus | 3 | 0.7735 |
| cGMP-dependent protein kinase 1 | P00516 | KGP1_BOVIN | Bos taurus | 3 | 0.7735 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7678 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7678 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7625 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7625 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7618 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7618 |
| Eugenol synthase 1 | Q15GI4 | EGS1_OCIBA | Ocimum basilicum | 3 | 0.7549 |
| Eugenol synthase 1 | Q15GI4 | EGS1_OCIBA | Ocimum basilicum | 3 | 0.7549 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7484 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7484 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7468 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7468 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 2 | 0.7465 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 2 | 0.7465 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7430 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7430 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7430 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7430 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7393 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7393 |
| Trichosurin | Q29147 | TRIC_TRIVU | Trichosurus vulpecula | 2 | 0.7388 |
| Trichosurin | Q29147 | TRIC_TRIVU | Trichosurus vulpecula | 2 | 0.7388 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 2 | 0.7364 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 2 | 0.7364 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7342 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7342 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7327 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7327 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7309 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7309 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7305 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7305 |
| Cytochrome P450 2E1 | P05181 | CP2E1_HUMAN | Homo sapiens | 3 | 0.7300 |
| Cytochrome P450 2E1 | P05181 | CP2E1_HUMAN | Homo sapiens | 3 | 0.7300 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7273 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7273 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 2 | 0.7260 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 2 | 0.7260 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7242 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7242 |
| DNA topoisomerase 1 | P06612 | TOP1_ECOLI | Escherichia coli | 3 | 0.7235 |
| DNA topoisomerase 1 | P06612 | TOP1_ECOLI | Escherichia coli | 3 | 0.7235 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7234 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7234 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7227 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7227 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7188 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7188 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7162 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7162 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7162 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7162 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7159 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7159 |
| Aldo-keto reductase family 1 member A1 | P50578 | AK1A1_PIG | Sus scrofa | 3 | 0.7157 |
| Aldo-keto reductase family 1 member A1 | P50578 | AK1A1_PIG | Sus scrofa | 3 | 0.7157 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7108 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7108 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 2 | 0.7106 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 2 | 0.7106 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7102 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7102 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 2 | 0.7080 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 2 | 0.7080 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7022 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7022 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7012 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7012 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7005 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7005 |