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(+)-isochromophilone VII

Family: Fungi - Chaetomiaceae
Kingdom: Fungi
Class: Azaphilone

Canonical Smiles	CCC(/C=C(/C=C/C1=CC2=C(Cl)C(=O)C(C(=O)C2(CO1)O)(C)OC(=O)C)\C)C
InChI	InChI=1S/C21H25ClO6/c1-6-12(2)9-13(3)7-8-15-10-16-17(22)18(24)20(5,28-14(4)23)19(25)21(16,26)11-27-15/h7-10,12,26H,6,11H2,1-5H3/b8-7+,13-9+
InChIKey	AJQIMDBOBJADCM-NJHPPEEMSA-N
Formula	C₂₁H₂₅ClO₆
HBA	6
HBD	1
MW	408.88
Rotatable Bonds	5
TPSA	89.9
LogP	3.15
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.48
Exact Mass	408.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chaetomium aureum	Chaetomiaceae	Fungi	79815

Showing of synonyms

Kabbaj FZ, Lu S, et al. (2015). Bioactive metabolites from Chaetomium aureum: Structure elucidation and inhibition of the Hsp90 machine chaperoning activity. Bioorganic and Medicinal Chemistry,2015,23(1),126-131. [View] [PubMed]

Pubchem: 6443571

Cas: 175448-30-3

Nmrshiftdb2: 60047538

No compound-protein relationship available.

SMILES: C1=COCC(C1=2)C(=O)CC(=O)C2

Level: 0

Mol. Weight: 408.88 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.55
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.76
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.83
Plasma Protein Binding: 42.56
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: 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: 3.87
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.58
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.44
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.95
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 1.01
Rat (Acute): 2.06
Rat (Chronic Oral): 2.23
Fathead Minnow: 5.07
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 368.09
Hydration Free Energy: -7.56
Log(D) at pH=7.4: 2.78
Log(P): 3.8
Log S: -4.28
Log(Vapor Pressure): -6.45
Melting Point: 128.86
pKa Acid: 4.62
pKa Basic: 3.6

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	3	0.9215
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	3	0.9215
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9059
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9059
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9042
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9042
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9024
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9024
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8561
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8561
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8494
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8494
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7945
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7945
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7836
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7836
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7814
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7814
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7803
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7803
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7794
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7794
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7758
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7758
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7756
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7756
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7753
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7753
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7733
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7733
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7732
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7732
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7723
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7723
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7720
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7720
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7691
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7691
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7682
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7682
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7676
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7676
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7676
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7676
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7675
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7675
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7620
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7620
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7607
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7607
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7604
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7604
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.7592
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.7592
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7563
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7563
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	2	0.7520
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	2	0.7520
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7520
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7520
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7491
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7491
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7485
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7485
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7480
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7480
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	2	0.7478
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	2	0.7478
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7466
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7466
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7455
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7455
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7441
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7441
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7431
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7431
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.7367
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.7367
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7365
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7365
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7306
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7306
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7293
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7293
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7290
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7290
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7255
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7255
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7248
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7248
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7232
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7232
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7226
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7226
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7208
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7208
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7183
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7183
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7178
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7178
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7168
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7168
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	2	0.7163
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	2	0.7163
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7119
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7119
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7108
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7108
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7102
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7102
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7061
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7061
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7027
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7027
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7019
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7019

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