2-methyl-4-oxo-4H-1-benzopyrane 5-carboxylic acid - Compound Card

2-methyl-4-oxo-4H-1-benzopyrane 5-carboxylic acid

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2-methyl-4-oxo-4H-1-benzopyrane 5-carboxylic acid

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles Cc1cc(=O)c2c(o1)cccc2C(=O)O
InChI InChI=1S/C11H8O4/c1-6-5-8(12)10-7(11(13)14)3-2-4-9(10)15-6/h2-5H,1H3,(H,13,14)
InChIKey QUYWIJNQKYUNLY-UHFFFAOYSA-N
Formula C11H8O4
HBA 3
HBD 1
MW 204.18
Rotatable Bonds 1
TPSA 67.51
LogP 1.8
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.09
Exact Mass 204.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus congolensis Ancistrocladaceae Plantae 714097

Showing of synonyms

  • Bringmann G, Spuziak J, et al. (2008). Six naphthylisoquinoline alkaloids and a related benzopyranone from a Congolese Ancistrocladus species related to Ancistrocladus congolensis. Phytochemistry,2008, 69(4), 1065-1075. [View] [PubMed]
Pubchem: 24814732

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 204.18 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
52.58
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
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
7.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.32
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.36
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
1.93
Micronucleos
Toxic
NR-AhR
Safe
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
Safe
T. Pyriformis
3.82
Rat (Acute)
1.91
Rat (Chronic Oral)
3.27
Fathead Minnow
3.87
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
342.81
Hydration Free Energy
-10.11
Log(D) at pH=7.4
-0.79
Log(P)
1.23
Log S
-2.53
Log(Vapor Pressure)
-5.51
Melting Point
208.77
pKa Acid
5.23
pKa Basic
5.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.9599
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.9599
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9349
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9349
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.9326
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.9326
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9173
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9173
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9129
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9129
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9060
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9060
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8981
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8981
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8937
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8937
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8937
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8937
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8928
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8928
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8927
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8927
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8862
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8862
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8826
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8826
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8702
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8702
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8597
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8597
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.8367
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.8367
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8281
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8281
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.8273
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.8273
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8204
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8204
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8069
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8069
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8062
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8062
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7988
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7988
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7960
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7960
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7867
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7867
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7803
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7803
Carbonic anhydrase 13 Q8N1Q1 CAH13_HUMAN Homo sapiens 3 0.7800
Carbonic anhydrase 13 Q8N1Q1 CAH13_HUMAN Homo sapiens 3 0.7800
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7799
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7799
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7786
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7786
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7602
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7602
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7453
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7453
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7416
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7416
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7390
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7390
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7388
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7388
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7382
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7382
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7354
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7354
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7350
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7350
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7314
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7314
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7285
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7285
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7282
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7282
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7262
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7262
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7224
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7224
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7213
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7213
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7190
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7190
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7172
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7172
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7154
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7154
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7140
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7140
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7116
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7116
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7073
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7073
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7073
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7073
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7069
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7069
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7052
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7052
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7051
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7051
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7050
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7050
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7050
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7050
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7046
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7046
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7018
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7018
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7013
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7013
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7001
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7001

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