Aspvanicin A - Compound Card

Aspvanicin A

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Aspvanicin A

Structure
Zoomed Structure
  • Family: Trichocomaceae
  • Kingdom: Fungi
  • Class: Naphthalenone
Canonical Smiles CO[C@@H]1[C@H](CC(=O)C)CC(=O)c2c1c(O)c(cc2O)OC
InChI InChI=1S/C15H18O6/c1-7(16)4-8-5-9(17)12-10(18)6-11(20-2)14(19)13(12)15(8)21-3/h6,8,15,18-19H,4-5H2,1-3H3/t8-,15-/m1/s1
InChIKey JVMMJSVRBNRJIB-ANRSDYALSA-N
Formula C15H18O6
HBA 6
HBD 2
MW 294.3
Rotatable Bonds 4
TPSA 93.06
LogP 1.98
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 294.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus versicolor Trichocomaceae Fungi 46472

Showing of synonyms

  • Abdelwahab M, Kurtán T, et al. (2018). Induced secondary metabolites from the endophytic fungus Aspergillus versicolor through bacterial co-culture and OSMAC approaches. Tetrahedron Letters,2018,59(27),2647-2652. [View]
Pubchem: 139591253

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CCCC2=O

Level: 0

Mol. Weight: 146.19 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
57.32
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.980
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.580
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.550
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.890
Rat (Acute)
2.430
Rat (Chronic Oral)
2.820
Fathead Minnow
3.950
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
380.050
Hydration Free Energy
-8.370
Log(D) at pH=7.4
1.200
Log(P)
0.91
Log S
-3.56
Log(Vapor Pressure)
-6.13
Melting Point
147.11
pKa Acid
5.87
pKa Basic
4.41
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.9593
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9564
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9537
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9532
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9466
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9456
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9429
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9382
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9285
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9241
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9169
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9153
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.9011
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8908
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8862
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8850
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8846
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8818
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8808
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8785
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8783
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8719
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8716
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8692
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8691
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8682
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8654
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8613
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8591
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8583
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8535
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8389
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 4 0.8331
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8301
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8289
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8283
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.8272
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8263
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8224
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8214
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8166
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 4 0.8115
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.8104
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7953
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7934
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7863
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7840
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7835
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7834
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7800
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7786
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7749
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7720
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7715
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7686
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7686
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7669
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7661
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7659
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7616
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7547
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7541
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7540
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7532
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7513
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7508
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7504
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7500
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7495
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7483
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7482
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7473
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7472
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7463
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7459
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7435
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7426
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7383
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7382
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7369
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7366
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7366
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7363
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7361
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7355
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7346
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7328
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7325
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7318
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7308
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7307
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7293
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7289
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7260
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7259
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7252
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7240
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7224
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7207
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7206
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7200
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7179
Thymidylate synthase P07607 TYSY_MOUSE Mus musculus 4 0.7151
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7147
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7146
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7139
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7138
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7126
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7121
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7114
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7113
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7102
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7101
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7101
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7095
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7095
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7086
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7081
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7079
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7071
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7068
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7055
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7050
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7050
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7040
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7039
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7036
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7033
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7033
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7031
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7027
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7022
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7019
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7017
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7012
Cytosolic IMP-GMP specific 5'-nucleotidase Q5ZZB6 Q5ZZB6_LEGPH Legionella pneumophila subsp. pneumophila 3 0.7004
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7003
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 4 0.7002
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7001
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7001

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