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Oxaline

Family: Fungi - Eurotiomycetidae
Kingdom: Fungi
Class: Alkaloid

Canonical Smiles	COC1=C[C@@]2(c3ccccc3N(C32N(C1=O)/C(=C/c1cnc[nH]1)/C(=O)N3)OC)C(C=C)(C)C
InChI	InChI=1S/C24H25N5O4/c1-6-22(2,3)23-12-19(32-4)21(31)28-18(11-15-13-25-14-26-15)20(30)27-24(23,28)29(33-5)17-10-8-7-9-16(17)23/h6-14H,1H2,2-5H3,(H,25,26)(H,27,30)/b18-11+/t23-,24?/m1/s1
InChIKey	SOHAVULMGIITDH-WNYKETQYSA-N
Formula	C₂₄H₂₅N₅O₄
HBA	6
HBD	2
MW	447.5
Rotatable Bonds	5
TPSA	99.79
LogP	2.44
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	447.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus austroafricanus	Eurotiomycetidae	Fungi	1220192

Showing of synonyms

Ebrahim W, El-Neketi M, et al. (2016). Metabolites from the fungal endophyte Aspergillus austroafricanus in axenic culture and in fungal−bacterial mixed cultures. Journal of Natural Products,2016,79,914-922. [View] [PubMed]

Pubchem: 6438440

Nmrshiftdb2: 80005658

Comptox: DTXSID60893990

CPRiL: 320131

SMILES: [nH]1cncc1C=C(C(=O)N2)N3C(=O)C=CC(C234)c5c(N4)cccc5

Level: 1

Mol. Weight: 447.5 g/mol

SMILES: N1C(=O)C(=C)N2C(=O)C=CC(C123)c4c(N3)cccc4

Level: 0

Mol. Weight: 447.5 g/mol

SMILES: c1c[nH]cn1

Level: 0

Mol. Weight: 447.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.07
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.060
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.120
Plasma Protein Binding: 82.37
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.170
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.310
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.230
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 9.680
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: -224.020
Rat (Acute): 2.370
Rat (Chronic Oral): 2.120
Fathead Minnow: 4.760
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 538.150
Hydration Free Energy: -3.540
Log(D) at pH=7.4: 2.330
Log(P): 1.43
Log S: -3.61
Log(Vapor Pressure): -10.38
Melting Point: 234.0
pKa Acid: 7.41
pKa Basic: 5.14

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9210
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9210
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9108
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9108
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8332
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8332
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8154
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8154
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8074
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8074
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7990
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7990
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7881
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7881
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7741
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7741
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7678
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7678
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7624
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7624
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7607
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7607
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7512
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7512
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7511
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7511
Kelch-like ECH-associated protein 1	Q14145	KEAP1_HUMAN	Homo sapiens	3	0.7449
Kelch-like ECH-associated protein 1	Q14145	KEAP1_HUMAN	Homo sapiens	3	0.7449
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7332
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7332
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7318
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7318
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7283
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7283
Protein-tyrosine kinase 2-beta	Q14289	FAK2_HUMAN	Homo sapiens	4	0.7272
Protein-tyrosine kinase 2-beta	Q14289	FAK2_HUMAN	Homo sapiens	4	0.7272
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7239
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7239
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7175
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7175
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7171
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7171
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7155
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7155
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7145
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7145
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7126
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7126
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7116
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7116
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7103
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7103
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7082
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7082
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7029
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7029
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7020
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7020

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