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14-hydroxyvaginatin

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

Canonical Smiles	Oc1ccc(cc1)C(=O)O[C@H]1C[C@](C)(O)[C@H](C[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C)O
InChI	InChI=1S/C22H32O6/c1-13(2)22(27)10-9-20(3)12-17(24)21(4,26)11-16(18(20)22)28-19(25)14-5-7-15(23)8-6-14/h5-8,13,16-18,23-24,26-27H,9-12H2,1-4H3/t16-,17-,18+,20+,21-,22+/m0/s1
InChIKey	QCLJCHLNAUUSNX-DJNRTHQISA-N
Formula	C₂₂H₃₂O₆
HBA	6
HBD	4
MW	392.49
Rotatable Bonds	3
TPSA	107.22
LogP	2.63
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.68
Exact Mass	392.22
Number of Lipinski Rule Violations	0

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

Showing of synonyms

Ahmed AA (1990). New Sesquiterpenes from Ferula sinaica. Journal of Natural Products,1990,53(2),483-486. [View] [PubMed]

Pubchem: 14681668

Zinc: ZINC000238755936

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2CCCCC(C23)CCC3

Level: 1

Mol. Weight: 392.49 g/mol

SMILES: C1CCC(C12)CCCCC2

Level: 0

Mol. Weight: 392.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 392.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.74
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.730
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.98

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.520
Plasma Protein Binding: 78.91
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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.380
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.580
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.160
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.660
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -6.670
Rat (Acute): 3.610
Rat (Chronic Oral): 2.410
Fathead Minnow: 4.030
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: 401.230
Hydration Free Energy: -8.700
Log(D) at pH=7.4: 2.610
Log(P): 3.17
Log S: -3.32
Log(Vapor Pressure): -8.01
Melting Point: 191.44
pKa Acid: 6.06
pKa Basic: 5.66

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7974
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7974
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7964
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7964
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7626
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7626
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7499
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7499
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7444
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7444
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7255
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7255
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7231
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7231
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7188
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7188
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7061
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7061
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7014
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7014

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