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Assafoetidnol A

Family: Plantae - Apiaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Sesquiterpene Coumarin

Canonical Smiles	C=C1C[C@@H](O)[C@H]2[C@@]([C@H]1COc1ccc3c(c1)oc(=O)cc3)(C)CC[C@H](C2(C)C)O
InChI	InChI=1S/C24H30O5/c1-14-11-18(25)22-23(2,3)20(26)9-10-24(22,4)17(14)13-28-16-7-5-15-6-8-21(27)29-19(15)12-16/h5-8,12,17-18,20,22,25-26H,1,9-11,13H2,2-4H3/t17-,18+,20+,22+,24-/m0/s1
InChIKey	DPUIHKUQXKLJMN-AVPXBJHFSA-N
Formula	C₂₄H₃₀O₅
HBA	5
HBD	2
MW	398.5
Rotatable Bonds	3
TPSA	79.9
LogP	3.91
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	398.21
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ferula assa-foetida	Apiaceae	Plantae	52471

Showing of synonyms

El-Razek MHA, Ohta S, et al. (2001). Sesquiterpene coumarins from the roots of Ferula assa-foetida. Phytochemistry,2001,58(8),1289-1295. [View]

Pubchem: 12041593

Cas: 403642-10-4

Zinc: ZINC000013384209

Nmrshiftdb2: 70037184

Comptox: DTXSID70193352

No compound-protein relationship available.

SMILES: C1CCCC(C12)CCC(=C)C2COc(cc3)cc(c34)oc(=O)cc4

Level: 1

Mol. Weight: 398.5 g/mol

SMILES: C=C(C1)CCC(C12)CCCC2

Level: 0

Mol. Weight: 398.5 g/mol

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 398.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.92
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.38
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.88
Plasma Protein Binding: 88.36
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: 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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.25
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.71
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.33
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.95
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: Toxic
T. Pyriformis: -14.23
Rat (Acute): 3.98
Rat (Chronic Oral): 1.71
Fathead Minnow: 3.98
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 459.4
Hydration Free Energy: -5.39
Log(D) at pH=7.4: 3.34
Log(P): 3.86
Log S: -4.71
Log(Vapor Pressure): -8.85
Melting Point: 170.14
pKa Acid: 6.6
pKa Basic: 6.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.9705
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.9705
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.9639
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.9639
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9531
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9531
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9457
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9457
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.9429
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.9429
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9174
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9174
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8772
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8772
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8747
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8747
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8625
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8625
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8559
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8559
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8420
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8420
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.8346
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.8346
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8204
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8204
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8113
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8113
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7979
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7979
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7919
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7919
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7874
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7874
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7842
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7842
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7805
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7805
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7805
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7805
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	3	0.7793
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	3	0.7793
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7741
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7741
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7728
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7728
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7701
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7701
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7693
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7693
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7673
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7673
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7671
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7671
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7669
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7669
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7669
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7669
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7654
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7654
Cytochrome P450 2E1	P05181	CP2E1_HUMAN	Homo sapiens	3	0.7637
Cytochrome P450 2E1	P05181	CP2E1_HUMAN	Homo sapiens	3	0.7637
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7622
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7622
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7543
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7543
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7540
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7540
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7533
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7533
DNA topoisomerase 1	P06612	TOP1_ECOLI	Escherichia coli	3	0.7526
DNA topoisomerase 1	P06612	TOP1_ECOLI	Escherichia coli	3	0.7526
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7498
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7498
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7484
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7484
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7480
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7480
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7418
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7418
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7397
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7397
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7392
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7392
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7390
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7390
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7387
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7387
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7375
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7375
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7348
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7348
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7343
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7343
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7320
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7320
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7287
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7287
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7254
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7254
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7251
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7251
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7231
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7231
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	4	0.7228
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	4	0.7228
Dicamba O-demethylase, oxygenase component	Q5S3I3	DDMC_STEMA	Stenotrophomonas maltophilia	2	0.7222
Dicamba O-demethylase, oxygenase component	Q5S3I3	DDMC_STEMA	Stenotrophomonas maltophilia	2	0.7222
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7220
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7220
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7213
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7213
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7210
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7210
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7188
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7188
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	2	0.7187
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	2	0.7187
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7183
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7183
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7157
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7157
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7155
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7155
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7152
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7152
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7151
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7151
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	2	0.7118
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	2	0.7118
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7117
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7117
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7112
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7112
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7091
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7091
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7075
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7075
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7067
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7067
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7052
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7052
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	2	0.7032
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	2	0.7032
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7031
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7031
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	2	0.7022
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	2	0.7022

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