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Feselol

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

Canonical Smiles	CC1=CC[C@H]2[C@@]([C@@H]1COc1ccc3c(c1)oc(=O)cc3)(C)CC[C@H](C2(C)C)O
InChI	InChI=1S/C24H30O4/c1-15-5-9-20-23(2,3)21(25)11-12-24(20,4)18(15)14-27-17-8-6-16-7-10-22(26)28-19(16)13-17/h5-8,10,13,18,20-21,25H,9,11-12,14H2,1-4H3/t18-,20-,21-,24+/m1/s1
InChIKey	MCTDXPDDZLFJHR-XLRKYUMYSA-N
Formula	C₂₄H₃₀O₄
HBA	4
HBD	1
MW	382.5
Rotatable Bonds	3
TPSA	59.67
LogP	4.94
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	382.21
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ferula sinaica	Apiaceae	Plantae	1514050
2	Ferula sinaica	Apiaceae	Plantae	1514050
3	Ferula vesceritensis	Apiaceae	Plantae	1514058

Showing of synonyms

Ahmed AA, Hegazy MEF, et al. (2007). Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species. Phytochemistry,2007,68(5),680-686. [View]
Ahmed AA (1990). New Sesquiterpenes from Ferula sinaica. Journal of Natural Products,1990,53(2),483-486. [View] [PubMed]
Oughlissi-Dehak K, Lawton P, et al. (2008). Sesquiterpenes from aerial parts of Ferula vesceritensis. Phytochemistry,2008,69(9),1933-1938. [View] [PubMed]

Pubchem: 179577

Cas: 51020-36-1

Zinc: ZINC000000704424

Chebi: 70609

Nmrshiftdb2: 60076448

Metabolights: MTBLC70609

Chembl: CHEMBL1651079

Comptox: DTXSID80199022

No compound-protein relationship available.

SMILES: c1cc(=O)oc(c12)cc(cc2)OCC3C=CCC(C34)CCCC4

Level: 1

Mol. Weight: 382.5 g/mol

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

Level: 0

Mol. Weight: 382.5 g/mol

SMILES: C1C=CCC(C12)CCCC2

Level: 0

Mol. Weight: 382.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.93
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.32
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.31

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.31
Plasma Protein Binding: 91.59
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.12
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.83
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.17
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.23
Micronucleos: Safe
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: -9.75
Rat (Acute): 2.4
Rat (Chronic Oral): 1.5
Fathead Minnow: 4.03
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 455.67
Hydration Free Energy: -5.37
Log(D) at pH=7.4: 4.4
Log(P): 5.16
Log S: -5.72
Log(Vapor Pressure): -8.15
Melting Point: 158.71
pKa Acid: 7.88
pKa Basic: 7.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9548
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9548
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9437
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9437
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.9430
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.9430
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8894
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8894
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8889
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8889
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8824
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8824
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.8708
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.8708
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8393
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8393
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8227
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8227
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8072
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8072
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8065
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8065
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8045
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8045
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.8034
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.8034
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7919
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7919
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7883
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7883
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7878
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7878
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7864
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7864
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7854
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7854
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7853
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7853
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7793
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7793
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7713
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7713
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7696
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7696
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7687
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7687
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7653
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7653
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7620
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7620
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7594
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7594
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7561
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7561
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7554
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7554
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7526
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7526
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7505
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7505
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7501
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7501
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7495
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7495
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7472
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7472
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7461
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7461
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7458
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7458
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7453
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7453
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7437
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7437
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7433
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7433
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7428
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7428
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	2	0.7388
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7388
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	2	0.7388
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7388
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7388
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7388
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7382
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7382
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7292
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7292
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7274
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7274
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7270
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7270
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7250
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7250
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
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7195
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7195
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7189
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7189
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7163
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7163
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7151
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7151
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7124
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7124
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7123
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7123
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7118
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7118
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7084
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7084
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7061
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7061
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7059
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7059
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7058
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7058
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	2	0.7026
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	2	0.7026
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7024
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7024
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7014
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7014
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7008
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7008

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