4,4'-diydroxypulvinone - Compound Card

4,4'-diydroxypulvinone

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4,4'-diydroxypulvinone

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Lactone
    • Subclass: Butyrolactone Derivative
Canonical Smiles Oc1ccc(cc1)/C=C/1\OC(=O)C(=C1O)c1ccc(cc1)O
InChI InChI=1S/C17H12O5/c18-12-5-1-10(2-6-12)9-14-16(20)15(17(21)22-14)11-3-7-13(19)8-4-11/h1-9,18-20H/b14-9-
InChIKey BNNVVTQUWNGKPH-ZROIWOOFSA-N
Formula C17H12O5
HBA 5
HBD 3
MW 296.28
Rotatable Bonds 2
TPSA 86.99
LogP 2.96
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 296.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus terreus Trichocomaceae Fungi 33178
2 Aspergillus flavipes Trichocomaceae Fungi 41900

Showing of synonyms

  • Nagia MM, El-Metwally MM, et al. (2012). Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Organic and Medicinal Chemistry Letters,2012,2(1),9. [View] [PubMed]
  • Chen H, Daletos G, et al. (2015). Inducing secondary metabolite production by the soil-dwelling fungus Aspergillus terreus through bacterial co-culture. Phytochemistry Letters,2015,12,35-41. [View]
Pubchem: 54675753
Kegg Ligand: C02006
Chebi: 17704
Nmrshiftdb2: 70022010
Metabolights: MTBLC17704
Bindingdb: 50453556

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=C(OC2=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 296.28 g/mol

Structure

SMILES: O=C1OC(=C)C=C1c2ccccc2

Level: 1

Mol. Weight: 296.28 g/mol

Structure

SMILES: O=C(O1)C=CC1=Cc2ccccc2

Level: 1

Mol. Weight: 296.28 g/mol

Structure

SMILES: C=C1C=CC(=O)O1

Level: 0

Mol. Weight: 296.28 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 296.28 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.990
Plasma Protein Binding
52.87
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.140
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.580
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.600
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.600
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.080
Rat (Acute)
2.210
Rat (Chronic Oral)
2.770
Fathead Minnow
4.440
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
448.530
Hydration Free Energy
-10.340
Log(D) at pH=7.4
2.250
Log(P)
1.92
Log S
-3.63
Log(Vapor Pressure)
-8.15
Melting Point
237.55
pKa Acid
7.61
pKa Basic
2.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.9440
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.9440
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9333
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9333
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9238
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9238
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 3 0.9178
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 3 0.9178
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8928
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8928
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.8862
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.8862
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8852
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8852
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 3 0.8776
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 3 0.8776
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8660
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8660
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8569
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8569
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8475
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8475
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8383
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8383
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8319
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8319
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8312
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8312
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8239
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8239
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.8146
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.8146
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7823
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7823
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7821
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7821
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7814
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7814
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7794
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7794
Carbonic anhydrase 5A, mitochondrial P23589 CAH5A_MOUSE Mus musculus 3 0.7765
Carbonic anhydrase 5A, mitochondrial P23589 CAH5A_MOUSE Mus musculus 3 0.7765
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 3 0.7728
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 3 0.7728
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.7590
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.7590
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7500
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7500
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7489
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7489
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7404
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7404
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7336
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7336
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7257
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7257
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7253
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7253
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7238
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7238
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7218
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7218
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7205
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7205
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7159
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7159
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7122
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7122
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7115
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7115
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7100
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7100
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7099
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7099
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7082
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7082
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7077
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7077
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7061
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7061
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.7040
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.7040

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