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5-O-methylsulochrin

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Benzophenone

Canonical Smiles	COc1cc(OC)c(c(c1)C(=O)OC)C(=O)c1c(O)cc(cc1O)C
InChI	InChI=1S/C18H18O7/c1-9-5-12(19)16(13(20)6-9)17(21)15-11(18(22)25-4)7-10(23-2)8-14(15)24-3/h5-8,19-20H,1-4H3
InChIKey	YLCJNMGKCHGJRF-UHFFFAOYSA-N
Formula	C₁₈H₁₈O₇
HBA	7
HBD	2
MW	346.34
Rotatable Bonds	5
TPSA	102.29
LogP	2.44
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.22
Exact Mass	346.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus wentii	Trichocomaceae	Fungi	5066

Showing of synonyms

Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]

Pubchem: 23983701

Cas: 77282-69-0

Gnps: CCMSLIB00004700879

Zinc: ZINC000014761004

Nmrshiftdb2: 70035937

Chembl: CHEMBL4529755

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 346.34 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 346.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.74
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.750
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.030
Plasma Protein Binding: 44.92
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.100
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.440
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.460
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.980
Micronucleos: Toxic
NR-AhR: Toxic
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: 3.550
Rat (Acute): 2.280
Rat (Chronic Oral): 3.220
Fathead Minnow: 4.560
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 412.700
Hydration Free Energy: -9.660
Log(D) at pH=7.4: 4.280
Log(P): 3.77
Log S: -6.5
Log(Vapor Pressure): -6.86
Melting Point: 135.1
pKa Acid: 7.97
pKa Basic: 2.12

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9186
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8779
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8770
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8722
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8639
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8593
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.8481
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8479
Enoyl-acyl carrier reductase	Q6UCJ9	Q6UCJ9_TOXGO	Toxoplasma gondii	4	0.8389
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8372
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8359
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8353
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.8296
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	4	0.8240
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8145
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8138
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8056
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8054
Enoyl-acyl carrier protein reductase	Q6TEI5	Q6TEI5_PLABE	Plasmodium berghei	4	0.7959
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.7873
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7855
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7805
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7751
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7688
Enoyl-ACP reductase	Q9BH77	Q9BH77_PLAFA	Plasmodium falciparum	4	0.7683
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7638
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7538
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7529
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	3	0.7490
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7447
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7440
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7423
Prostaglandin E synthase 2	Q9N0A4	PGES2_MACFA	Macaca fascicularis	3	0.7413
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7359
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic	P80030	FABI_BRANA	Brassica napus	4	0.7355
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7346
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7326
Enoyl-ACP reductase	Q9BH77	Q9BH77_PLAFA	Plasmodium falciparum	4	0.7310
Peptide deformylase 1B, chloroplastic/mitochondrial	Q9FUZ2	DEF1B_ARATH	Arabidopsis thaliana	3	0.7310
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7297
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7266
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7252
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7246
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7243
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7204
Protein S100-A4	P26447	S10A4_HUMAN	Homo sapiens	3	0.7196
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7137
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7133
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7133
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7120
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7117
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7093
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7074
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7044
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7038
Pentalenic acid synthase	Q825I8	CYP28_STRAW	Streptomyces avermitilis	2	0.7019

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