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Neobulgarone E

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

Canonical Smiles	COc1cc(C)cc2c1C(=O)c1c([C@H]2[C@H]2c3cc(C)cc(c3C(=O)c3c2c(Cl)c(O)cc3O)OC)c(Cl)c(cc1O)O
InChI	InChI=1S/C32H24Cl2O8/c1-11-5-13-21(19(7-11)41-3)31(39)25-15(35)9-17(37)29(33)27(25)23(13)24-14-6-12(2)8-20(42-4)22(14)32(40)26-16(36)10-18(38)30(34)28(24)26/h5-10,23-24,35-38H,1-4H3/t23-,24-/m1/s1
InChIKey	QAZZAQNQJFRMEL-DNQXCXABSA-N
Formula	C₃₂H₂₄Cl₂O₈
HBA	8
HBD	4
MW	607.44
Rotatable Bonds	3
TPSA	133.52
LogP	6.5
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	606.08
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: 10531758

Cas: 315209-19-9

Zinc: ZINC000066102002

Nmrshiftdb2: 70010996

Chembl: CHEMBL1643637

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: 607.44 g/mol

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

Level: 0

Mol. Weight: 607.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.61
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.940
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 5.87

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.370
Plasma Protein Binding: 95.01
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: 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: 6.250
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.190
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.610
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.810
Micronucleos: Toxic
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: Toxic
T. Pyriformis: -10642.980
Rat (Acute): 2.260
Rat (Chronic Oral): 3.670
Fathead Minnow: 30.710
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: 486.370
Hydration Free Energy: -3.080
Log(D) at pH=7.4: 4.600
Log(P): 7.51
Log S: -7.64
Log(Vapor Pressure): -13.01
Melting Point: 260.18
pKa Acid: 7.81
pKa Basic: 2.84

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8848
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8848
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8695
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8695
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8310
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8310
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.8006
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.8006
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7917
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7917
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7914
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7914
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7896
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7896
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7883
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7883
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7824
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7824
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7409
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7409
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7194
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7194
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7158
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7158
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7092
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7092
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7085
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7085
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7061
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7061

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