Aurasperone C - Compound Card

Aurasperone C

Select a section from the left sidebar

Aurasperone C

Structure
Zoomed Structure
  • Family: Fungi - Dematiaceae
  • Kingdom: Fungi
  • Class: Lactone
    • Subclass: Pyrone Derivative
Canonical Smiles COc1cc(OC)c2c(c1)c(c1c(O)cc3c(c1OC)c(O)c1c(c3)OC(CC1=O)(C)O)c1c(c2O)C(=O)CC(O1)(C)O
InChI InChI=1S/C31H28O12/c1-30(37)10-16(33)23-19(42-30)7-12-6-15(32)24(28(41-5)20(12)26(23)35)22-14-8-13(39-3)9-18(40-4)21(14)27(36)25-17(34)11-31(2,38)43-29(22)25/h6-9,32,35-38H,10-11H2,1-5H3
InChIKey BAIJEJFONPISHA-UHFFFAOYSA-N
Formula C31H28O12
HBA 12
HBD 5
MW 592.55
Rotatable Bonds 4
TPSA 181.44
LogP 4.15
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 592.16
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: 179521
Chebi: 133815
Nmrshiftdb2: 70073802
Metabolights: MTBLC133815
CPRiL: 421472
Structure

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

Level: 1

Mol. Weight: 592.55 g/mol

Structure

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

Level: 0

Mol. Weight: 592.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.66
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.860
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
7.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
60.85
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
10.760
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.750
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.900
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.730
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
-12698.550
Rat (Acute)
2.780
Rat (Chronic Oral)
3.670
Fathead Minnow
33.690
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
489.180
Hydration Free Energy
-2.930
Log(D) at pH=7.4
3.230
Log(P)
4.8
Log S
-7.44
Log(Vapor Pressure)
-13.67
Melting Point
233.42
pKa Acid
7.04
pKa Basic
3.0
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 0.9597
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9597
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9261
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9261
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.9168
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.9168
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8868
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8868
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8684
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8684
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8371
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8371
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8357
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8357
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8235
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8235
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7741
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7741
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 5 0.7544
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 5 0.7544
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7536
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7536
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7301
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7301
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 4 0.7276
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 4 0.7276
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7273
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7273
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7273
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7273
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7268
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7268
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7193
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7193
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7124
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7124

Download SDF