Aspvanicin B - Compound Card

Aspvanicin B

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Aspvanicin B

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-GLEZIHRCSA-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: 139591254

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)
-4.5
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
-2.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
56.44
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
15.000
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.510
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
1.800
Rat (Acute)
2.420
Rat (Chronic Oral)
2.830
Fathead Minnow
3.950
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
380.460
Hydration Free Energy
-8.420
Log(D) at pH=7.4
1.270
Log(P)
0.86
Log S
-3.53
Log(Vapor Pressure)
-6.14
Melting Point
141.78
pKa Acid
5.85
pKa Basic
4.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9680
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9511
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9213
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9148
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9147
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9054
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9018
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9000
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8987
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8982
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8895
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8890
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8889
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8862
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8854
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8848
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 4 0.8791
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8727
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8700
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8639
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.8633
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8624
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8582
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8559
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8552
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8499
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8496
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8495
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8489
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8461
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8438
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8380
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.8340
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8298
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8196
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8184
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8121
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8116
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8099
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8087
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8050
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8024
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7946
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7911
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7897
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7883
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7838
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7831
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7773
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7757
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7647
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7611
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7592
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7581
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7576
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7573
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7543
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7525
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7523
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7505
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7504
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7484
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7476
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7471
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7471
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7463
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7452
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7448
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7432
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7413
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7409
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7385
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7368
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7358
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7350
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7347
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7343
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7332
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7314
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7301
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7300
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7299
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7295
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7293
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7281
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7281
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7270
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7270
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7241
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7232
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7223
Threonine synthase 1, chloroplastic Q9S7B5 THRC1_ARATH Arabidopsis thaliana 3 0.7208
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7201
Cytidine deaminase P19079 CDD_BACSU Bacillus subtilis 4 0.7199
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7177
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7169
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7167
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7161
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7158
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7154
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7142
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7140
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7135
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7118
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7115
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7109
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7096
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7096
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7095
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7092
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7079
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7079
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7071
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7067
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7066
NAD-dependent protein deacetylase sirtuin-3, mitochondrial Q9NTG7 SIR3_HUMAN Homo sapiens 4 0.7065
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7039
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7036
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7034
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7034
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7031
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 3 0.7031
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7027
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7019
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7015

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