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6alpha-p-hydroxybenzoyloxy-4beta-hydroxydauc-8-ene-10-one

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

Canonical Smiles	CC([C@]1(O)C[C@H]([C@]2([C@H]1[C@@H](O)CC(=CC2=O)C)C)OC(=O)c1ccc(cc1)O)C
InChI	InChI=1S/C22H28O6/c1-12(2)22(27)11-18(28-20(26)14-5-7-15(23)8-6-14)21(4)17(25)10-13(3)9-16(24)19(21)22/h5-8,10,12,16,18-19,23-24,27H,9,11H2,1-4H3/t16-,18+,19+,21-,22+/m0/s1
InChIKey	QVHLMUNIPJCKOA-IHXMQYCKSA-N
Formula	C₂₂H₂₈O₆
HBA	6
HBD	3
MW	388.46
Rotatable Bonds	3
TPSA	104.06
LogP	2.61
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	388.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ferula sinaica	Apiaceae	Plantae	1514050

Showing of synonyms

Ahmed AA (1991). Daucanes and other constituents from Ferula sinaica. Phytochemistry,1991,30(4),1207-1210. [View]

Pubchem: 162843975

Nmrshiftdb2: 60044076

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC=CC3=O

Level: 1

Mol. Weight: 388.46 g/mol

SMILES: C1CCC(C12)CCC=CC2=O

Level: 0

Mol. Weight: 388.46 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 388.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.82
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.64
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.76

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.54
Plasma Protein Binding: 81.22
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: 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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.28
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.49
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.21
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.02
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: -4.85
Rat (Acute): 3.41
Rat (Chronic Oral): 2.62
Fathead Minnow: 4.05
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: 406.9
Hydration Free Energy: -8.37
Log(D) at pH=7.4: 2.49
Log(P): 3.3
Log S: -3.77
Log(Vapor Pressure): -8.15
Melting Point: 189.15
pKa Acid: 6.9
pKa Basic: 4.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9309
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9309
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8689
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8689
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8233
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8233
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8085
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8085
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7992
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7992
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7573
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7573
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7524
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7524
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7487
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7487
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7455
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7455
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7286
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7286
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7217
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7217
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7146
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7146
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7132
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7132
Formylmethanofuran--tetrahydromethanopterin formyltransferase	Q49610	FTR_METKA	Methanopyrus kandleri	3	0.7112
Formylmethanofuran--tetrahydromethanopterin formyltransferase	Q49610	FTR_METKA	Methanopyrus kandleri	3	0.7112
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7078
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7078
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7057
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7057
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7034
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7034
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7034
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7034
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7028
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7028
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7008
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7008
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7003
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7003

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