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Aurasperone A

Family: Fungi - Dematiaceae
Kingdom: Fungi
Class: Lactone
- Subclass: Pyrone Derivative

Canonical Smiles	COc1cc(OC)c2c(c1)c(c1c(OC)cc3c(c1OC)c(O)c1c(c3)oc(cc1=O)C)c1c(c2O)c(=O)cc(o1)C
InChI	InChI=1S/C32H26O10/c1-13-7-18(33)26-22(41-13)10-15-9-20(38-4)28(31(40-6)23(15)29(26)35)25-17-11-16(37-3)12-21(39-5)24(17)30(36)27-19(34)8-14(2)42-32(25)27/h7-12,35-36H,1-6H3
InChIKey	QAHRSPAZSGMZMT-UHFFFAOYSA-N
Formula	C₃₂H₂₆O₁₀
HBA	10
HBD	2
MW	570.55
Rotatable Bonds	5
TPSA	137.8
LogP	5.94
Number Rings	6
Number Aromatic Rings	6
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	570.15
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Alternaria alternata	Dematiaceae	Fungi	5599

Showing of synonyms

Shaaban M, Shaaban KA, et al. (2012). Seven naphtho-gamma-pyrones from the marine derived fungus Alternaria alternata: structure elucidation and biological properties. Organic and Medicinal Chemistry Letters,2012,2,6. [View] [PubMed]

Pubchem: 3084216

Cas: 15085-74-2

Zinc: ZINC000044351309

Chebi: 133760

Nmrshiftdb2: 70014563

Metabolights: MTBLC133760

Chembl: CHEMBL450763

Comptox: DTXSID30164629

CPRiL: 278466

SMILES: c1cccc(c12)cc3c(occc3=O)c2-c(cc4)cc(c5)c4cc(c56)occc6=O

Level: 1

Mol. Weight: 570.55 g/mol

SMILES: O=c1ccoc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 570.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.25
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.800
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 7.91

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.870
Plasma Protein Binding: 69.04
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: 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: Non-Inhibitor

Excretion

Clearance: 4.060
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.050
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.510
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.870
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: -13311.180
Rat (Acute): 2.950
Rat (Chronic Oral): 3.000
Fathead Minnow: 37.610
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 518.490
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 3.940
Log(P): 5.57
Log S: -8.02
Log(Vapor Pressure): -14.6
Melting Point: 280.0
pKa Acid: 9.73
pKa Basic: 2.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9622
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9622
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9274
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9274
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8952
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8952
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8931
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8931
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8922
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8922
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8871
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8871
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8648
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8648
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8599
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8599
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	4	0.8111
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	4	0.8111
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8086
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8086
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7973
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7973
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7854
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7854
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7831
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7831
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7828
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7828
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7798
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7798
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7600
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7600
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7589
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7589
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7587
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7587
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7581
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7581
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7514
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7514
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7476
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7476
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7455
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7455
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7417
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7417
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7400
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7400
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7395
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7395
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7358
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7358
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7341
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7341
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7287
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7287
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7284
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7284
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	4	0.7282
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	4	0.7282
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7274
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7274
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7271
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7271
Caspase-7	P55210	CASP7_HUMAN	Homo sapiens	3	0.7268
Caspase-7	P55210	CASP7_HUMAN	Homo sapiens	3	0.7268
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7232
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7232
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7215
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7215
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7211
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7211
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7204
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7204
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7159
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7159
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7120
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7120
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7108
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7108
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7067
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7067
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7028
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7028
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7008
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7008

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