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Aspernolide G

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Terpenoid

Canonical Smiles	CCOC1=C(c2ccc(cc2)O)[C@](OC1=O)(Cc1ccc(c(c1)C[C@@H](C(O)(C)C)O)O)C(=O)OC
InChI	InChI=1S/C26H30O9/c1-5-34-22-21(16-7-9-18(27)10-8-16)26(24(31)33-4,35-23(22)30)14-15-6-11-19(28)17(12-15)13-20(29)25(2,3)32/h6-12,20,27-29,32H,5,13-14H2,1-4H3/t20-,26+/m0/s1
InChIKey	QUSUCMRGJBZSBW-RXFWQSSRSA-N
Formula	C₂₆H₃₀O₉
HBA	9
HBD	4
MW	486.52
Rotatable Bonds	9
TPSA	142.75
LogP	2.23
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	486.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus terreus	Trichocomaceae	Fungi	33178

Showing of synonyms

Ibrahim S, Elkhayat E, et al. (2015). Aspernolides F and G, new butyrolactones from the endophytic fungus Aspergillus terreus. Phytochemistry Letters, 2015,14,84–90. [View]

Pubchem: 132556698

Nmrshiftdb2: 70110048

No compound-protein relationship available.

SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 486.52 g/mol

SMILES: O=C1C=CC(O1)Cc2ccccc2

Level: 1

Mol. Weight: 486.52 g/mol

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 486.52 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 486.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 486.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.12
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.94
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.64

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.95
Plasma Protein Binding: 62.14
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-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: 10.33
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.07
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.64
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.45
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -202.25
Rat (Acute): 2.26
Rat (Chronic Oral): 2.86
Fathead Minnow: 5.01
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 508.5
Hydration Free Energy: -2.91
Log(D) at pH=7.4: 2.5
Log(P): 1.51
Log S: -3.19
Log(Vapor Pressure): -9.65
Melting Point: 189.52
pKa Acid: 6.73
pKa Basic: 5.81

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9535
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.9236
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8822
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8784
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8723
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8711
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8688
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8646
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8580
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8439
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8394
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8250
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8104
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8091
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8085
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8000
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7942
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7926
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7849
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7799
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7698
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7603
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7569
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7532
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7514
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7469
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7462
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7454
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7438
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	3	0.7411
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7400
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7379
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7317
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7232
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7225
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7211
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7207
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7185
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7179
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7177
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7166
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7134
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7107
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7104
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7063
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7042
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7029
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7015

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