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Deacetylated sclerotiorin

Family: Fungi - Chaetomiaceae
Kingdom: Fungi
Class: Azaphilone

Canonical Smiles	CC[C@@H](/C=C(/C=C/C1=CC2=C(Cl)C(=O)[C@](C(=O)C2=CO1)(C)O)\C)C
InChI	InChI=1S/C19H21ClO4/c1-5-11(2)8-12(3)6-7-13-9-14-15(10-24-13)17(21)19(4,23)18(22)16(14)20/h6-11,23H,5H2,1-4H3/b7-6+,12-8+/t11-,19+/m0/s1
InChIKey	SBUBEONHXLXYBK-GFYBKASGSA-N
Formula	C₁₉H₂₁ClO₄
HBA	4
HBD	1
MW	348.83
Rotatable Bonds	4
TPSA	63.6
LogP	3.73
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.37
Exact Mass	348.11
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: 6476027

Cas: 34696-50-9

Zinc: ZINC000034073633

Nmrshiftdb2: 60047542

Chembl: CHEMBL3353800

No compound-protein relationship available.

SMILES: C1OC=CC(C=12)=CC(=O)CC2=O

Level: 0

Mol. Weight: 348.83 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.75
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.74
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.73

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.08
Plasma Protein Binding: 64.33
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: 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: 2.64
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: 0.12
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.46
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 0.72
Rat (Acute): 2.26
Rat (Chronic Oral): 2.15
Fathead Minnow: 5.14
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 374.93
Hydration Free Energy: -8.86
Log(D) at pH=7.4: 3.62
Log(P): 3.77
Log S: -4.95
Log(Vapor Pressure): -6.45
Melting Point: 143.3
pKa Acid: 5.5
pKa Basic: 3.7

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9129
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9129
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.8924
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.8924
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8915
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8915
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8809
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8809
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7946
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7946
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7839
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7839
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7828
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7828
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7730
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7730
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7718
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7718
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7711
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7711
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7698
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7698
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7696
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7696
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7657
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7657
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7617
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7617
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7616
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7616
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7614
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7614
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7612
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7612
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7585
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7585
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7579
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7579
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7563
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7563
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7562
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7562
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	2	0.7560
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	2	0.7560
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7543
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7543
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7538
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7538
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7526
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7526
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7489
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7489
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7461
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7461
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7427
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7427
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7420
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7420
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7405
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7405
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7404
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7404
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7386
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7386
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7348
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7348
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7344
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7344
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7340
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7340
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7334
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7334
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7326
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7326
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7324
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7324
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7321
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7321
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7284
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7284
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7274
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7274
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7268
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7268
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7255
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7255
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7231
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7231
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7215
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7215
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7207
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7207
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7197
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7197
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7184
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7184
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7180
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7180
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7168
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7168
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7155
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7155
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	3	0.7143
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	3	0.7143
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7111
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7111
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7108
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7108
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7098
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7098
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7068
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7068
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7038
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7038
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7037
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7037
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7034
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7034
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7019
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7019
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7015
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7015
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7005
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7005
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7001
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7001

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