ANPDB

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Aurasperone B

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)O)c1c(c2O)C(=O)CC(O1)(C)O
InChI	InChI=1S/C32H30O12/c1-31(37)11-16(33)24-20(43-31)8-13-7-18(40-4)26(29(42-6)21(13)27(24)35)23-15-9-14(39-3)10-19(41-5)22(15)28(36)25-17(34)12-32(2,38)44-30(23)25/h7-10,35-38H,11-12H2,1-6H3
InChIKey	VIFQAHKDYKZMMS-UHFFFAOYSA-N
Formula	C₃₂H₃₀O₁₂
HBA	12
HBD	4
MW	606.58
Rotatable Bonds	5
TPSA	170.44
LogP	4.45
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.31
Exact Mass	606.17
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: 179522

Cas: 41689-67-2

Chebi: 133756

Nmrshiftdb2: 70073803

Metabolights: MTBLC133756

No compound-protein relationship available.

SMILES: c1cccc(c12)cc3c(OCCC3=O)c2-c(cc4)cc(c5)c4cc(c56)OCCC6=O

Level: 1

Mol. Weight: 606.58 g/mol

SMILES: O=C1CCOc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 606.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.31
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.790
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 11.81

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.170
Plasma Protein Binding: 58.54
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.170
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.230
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.820
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.100
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: Toxic
T. Pyriformis: -21824.860
Rat (Acute): 3.210
Rat (Chronic Oral): 3.460
Fathead Minnow: 48.850
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 414.700
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 3.420
Log(P): 4.68
Log S: -7.42
Log(Vapor Pressure): -13.37
Melting Point: 227.91
pKa Acid: 7.07
pKa Basic: 2.32

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	0.9678
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9678
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9326
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9326
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8925
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8925
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8902
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8902
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8874
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8874
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8657
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8657
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8566
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8566
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8161
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8161
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7971
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7971
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7743
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7743
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7644
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7644
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7541
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7541
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7510
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7510
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7484
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7484
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7326
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7326
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7323
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7323
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7266
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7266
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7252
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7252
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7250
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7250
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7168
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7168
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7122
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7122
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7076
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7076
Genome polyprotein	P29991	POLG_DEN27	Dengue virus type 2	3	0.7016
Genome polyprotein	P29991	POLG_DEN27	Dengue virus type 2	3	0.7016
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7004
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7004

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