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Neobulgarone G

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Quinone
- Subclass: Dianthrone

Canonical Smiles	OCc1cc(OC)c2c(c1)[C@@H](c1c(C2=O)c(O)cc(c1Cl)O)[C@H]1c2cc(C)cc(c2C(=O)c2c1c(Cl)c(O)cc2O)OC
InChI	InChI=1S/C32H24Cl2O9/c1-11-4-13-21(19(5-11)42-2)31(40)25-15(36)8-17(38)29(33)27(25)23(13)24-14-6-12(10-35)7-20(43-3)22(14)32(41)26-16(37)9-18(39)30(34)28(24)26/h4-9,23-24,35-39H,10H2,1-3H3/t23-,24-/m1/s1
InChIKey	MQMWBFUKNWTRJV-DNQXCXABSA-N
Formula	C₃₂H₂₄Cl₂O₉
HBA	9
HBD	5
MW	623.44
Rotatable Bonds	4
TPSA	153.75
LogP	5.69
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	622.08
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Penicillium species	Trichocomaceae	Fungi	5073

Showing of synonyms

Aly AH, Debbab A, et al. (2011). NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum. Bioorganic and Medicinal Chemistry,2011,19(1),414-421. [View] [PubMed]

Pubchem: 53317590

Zinc: ZINC000072123724

Nmrshiftdb2: 80008151

Chembl: CHEMBL1643636

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1C(c(c23)cccc3)C(c(c45)cccc5)c6c(C4=O)cccc6

Level: 1

Mol. Weight: 623.44 g/mol

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 623.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.83
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.02
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 10.19

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.2
Plasma Protein Binding: 90.78
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.57
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.91
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.62
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.84
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -18496.09
Rat (Acute): 2.24
Rat (Chronic Oral): 3.95
Fathead Minnow: 44.57
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 464.53
Hydration Free Energy: -2.99
Log(D) at pH=7.4: 3.9
Log(P): 6.16
Log S: -6.66
Log(Vapor Pressure): -17.22
Melting Point: 234.56
pKa Acid: 7.93
pKa Basic: 2.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.9250
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.9250
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8831
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8831
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8698
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8698
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8477
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8477
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8235
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8235
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	3	0.8037
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	3	0.8037
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7983
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7983
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7961
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7961
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7938
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7938
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.7808
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.7808
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7429
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7429
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7345
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7345
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7307
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7307
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7104
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7104
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7084
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7084
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7038
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7038

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