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Viscic acid

Family: Asteraceae-Compositae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene

Canonical Smiles	C=C1[C@H](O)CC[C@]2([C@H]1C[C@@H](CC2)C(=C)C(=O)O)C
InChI	InChI=1S/C15H22O3/c1-9(14(17)18)11-4-6-15(3)7-5-13(16)10(2)12(15)8-11/h11-13,16H,1-2,4-8H2,3H3,(H,17,18)/t11-,12+,13-,15+/m1/s1
InChIKey	GQDFYCPPHMEHJL-COMQUAJESA-N
Formula	C₁₅H₂₂O₃
HBA	2
HBD	2
MW	250.34
Rotatable Bonds	2
TPSA	57.53
LogP	2.76
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	18
Formal Charge	0
Fraction CSP3	0.67
Exact Mass	250.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dittrichia graveolens	Asteraceae-Compositae	Plantae	1532790
2	Tarchonanthus camphoratus	Asteraceae-Compositae	Plantae	41650

Showing of synonyms

Abou-Douh AM (2008). New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens. Chemical and Pharmaceutical Bulletin,2008,56(11),1535-1545. [View] [PubMed]
Hegazy MEF, Tawfik WA, et al. (2015). Sesquiterpene acid derivatives from Tarchonanthus camphoratus. Research Journal of Pharmaceutical, Biological and Chemical Sciences,2015,6(1),659-663. [View]

Pubchem: 38348725

Zinc: ZINC000031157123

Nmrshiftdb2: 60022688

No compound-protein relationship available.

SMILES: C=C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 150.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.71
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.51
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.51
Plasma Protein Binding: 56.28
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: 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: 4.63
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.52
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.37
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.03
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -1.6
Rat (Acute): 2.76
Rat (Chronic Oral): 2.48
Fathead Minnow: 3.94
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 331.9
Hydration Free Energy: -7.52
Log(D) at pH=7.4: 0.0
Log(P): 2.56
Log S: -2.74
Log(Vapor Pressure): -6.11
Melting Point: 138.54
pKa Acid: 4.1
pKa Basic: 8.11

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9180
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9180
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9161
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9161
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.9059
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.9059
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.9058
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.9058
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8978
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8978
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8934
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8934
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8833
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8833
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8792
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8792
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8724
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8724
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8657
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8657
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8341
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8341
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8332
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8332
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8291
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8291
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8105
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8105
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8017
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8017
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7970
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7970
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7923
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7923
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7749
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7749
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7732
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7732
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7629
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7629
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7553
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7553
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7523
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7523
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7505
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7505
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7505
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7505
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7489
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7489
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7486
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7486
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7483
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7483
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7474
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7474
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7472
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7472
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7419
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7419
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7398
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7398
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7384
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7384
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7384
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7384
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7383
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7383
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7380
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7380
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7379
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7379
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7373
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7373
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7368
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7368
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7365
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7365
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7323
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7323
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7319
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7319
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7314
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7314
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7314
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7314
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7306
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7306
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7296
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7296
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7292
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7292
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7291
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7291
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7281
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7281
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7257
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7257
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7245
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7245
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7243
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7243
Corticosteroid-binding globulin	P31211	CBG_RAT	Rattus norvegicus	3	0.7227
Corticosteroid-binding globulin	P31211	CBG_RAT	Rattus norvegicus	3	0.7227
Glucocorticoid receptor	P04150	GCR_HUMAN	Homo sapiens	3	0.7220
Glucocorticoid receptor	P04150	GCR_HUMAN	Homo sapiens	3	0.7220
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7213
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7213
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7208
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7208
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7203
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7203
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7202
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7202
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7201
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7201
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7197
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7197
Androgen receptor	P19091	ANDR_MOUSE	Mus musculus	3	0.7194
Androgen receptor	P19091	ANDR_MOUSE	Mus musculus	3	0.7194
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7189
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7189
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7186
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7186
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7184
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7184
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7180
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7180
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7176
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7176
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7174
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7174
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7169
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7169
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7163
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7163
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7162
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7162
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7160
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7160
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7154
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7154
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7150
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7150
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7142
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7142
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7126
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7126
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7126
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7126
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7123
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7123
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7112
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7112
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7111
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7111
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7055
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7055

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