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4-epi-isoinuviscolide

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

Canonical Smiles	CC1=C[C@@H]2OC(=O)C(=C)[C@H]2C[C@@H]2[C@H]1CC[C@]2(C)O
InChI	InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h6,10-13,17H,2,4-5,7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1
InChIKey	APMKESKZWHNIDJ-PFFFPCNUSA-N
Formula	C₁₅H₂₀O₃
HBA	3
HBD	1
MW	248.32
Rotatable Bonds	0
TPSA	46.53
LogP	2.21
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	18
Formal Charge	0
Fraction CSP3	0.67
Exact Mass	248.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dittrichia graveolens	Asteraceae	Plantae	1532790

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]

Pubchem: 53320574

Cas: 68832-39-3

Zinc: ZINC000066100070

Chebi: 69347

Nmrshiftdb2: 60073932

Metabolights: MTBLC69347

Chembl: CHEMBL1644107

No compound-protein relationship available.

SMILES: C=C1C(=O)OC(C12)C=CC3C(C2)CCC3

Level: 0

Mol. Weight: 248.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.84
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.45
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.55
Plasma Protein Binding: 44.4
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: 10.68
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.26
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.47
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.03
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: 0.76
Rat (Acute): 2.34
Rat (Chronic Oral): 1.72
Fathead Minnow: 3.92
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 325.81
Hydration Free Energy: -5.86
Log(D) at pH=7.4: 1.8
Log(P): 1.86
Log S: -2.86
Log(Vapor Pressure): -4.99
Melting Point: 136.12
pKa Acid: 9.23
pKa Basic: 6.77

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9472
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9472
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.9295
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.9295
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9247
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9247
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8974
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8974
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8837
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8837
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8749
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8749
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8658
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8658
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8511
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8511
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8448
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8448
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8435
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8435
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7908
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7908
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7889
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7889
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7784
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7784
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7777
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7777
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7757
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7757
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7728
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7728
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7634
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7634
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7612
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7612
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7594
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7594
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7569
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7569
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7535
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7535
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7458
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7458
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7431
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7431
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7422
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7422
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7336
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7336
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7331
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7331
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7301
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7301
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7289
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7289
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7258
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7258
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7194
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7194
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7190
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7190
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7146
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7146
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7145
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7145
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7093
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7093
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7017
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7017
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7010
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7010
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7008
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7008

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