5,7,2',3''-tetrahydroxy-2'',2''-dimethyldihydropyrano-[5'',6'':3',4']-isoflavanone - Compound Card

5,7,2',3''-tetrahydroxy-2'',2''-dimethyldihydropyrano-[5'',6'':3',4']-isoflavanone

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5,7,2',3''-tetrahydroxy-2'',2''-dimethyldihydropyrano-[5'',6'':3',4']-isoflavanone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavanone
Canonical Smiles Oc1cc(O)c2c(c1)OC[C@@H](C2=O)c1ccc2c(c1O)CC(C(O2)(C)C)O
InChI InChI=1S/C20H20O7/c1-20(2)16(23)7-11-14(27-20)4-3-10(18(11)24)12-8-26-15-6-9(21)5-13(22)17(15)19(12)25/h3-6,12,16,21-24H,7-8H2,1-2H3/t12-,16?/m1/s1
InChIKey YACZUBKNMXSTQK-ZGTOLYCTSA-N
Formula C20H20O7
HBA 7
HBD 4
MW 372.37
Rotatable Bonds 1
TPSA 116.45
LogP 2.24
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 372.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Platycelyphium voënse Leguminosae/Fabaceae Plantae 149667

Showing of synonyms

  • Gumula I, Heydenreic M, et al. (2012). Four isoflavanones from the stem bark of Platycelphium voënse.. Phytochemistry Letters,2012,5(1),150–154. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OCC(C2=O)c(c3)ccc(c34)OCCC4

Level: 1

Mol. Weight: 372.37 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 372.37 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 372.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.19
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.01
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.99
Plasma Protein Binding
72.09
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
11.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.38
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.86
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.18
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
Toxic
T. Pyriformis
-1.69
Rat (Acute)
2.27
Rat (Chronic Oral)
2.72
Fathead Minnow
4.12
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
480.99
Hydration Free Energy
-9.6
Log(D) at pH=7.4
2.15
Log(P)
3.19
Log S
-5.42
Log(Vapor Pressure)
-8.61
Melting Point
210.08
pKa Acid
6.39
pKa Basic
5.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9470
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9470
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9258
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9258
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9187
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9187
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8852
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8852
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8821
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8821
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8727
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8727
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8727
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8727
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8707
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8707
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8682
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8682
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8666
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8666
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8612
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8612
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8533
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8533
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8517
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8517
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8401
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8401
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 4 0.8362
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 4 0.8362
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8348
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8348
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8320
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8320
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8270
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8270
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8225
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8225
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8181
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8181
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8170
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8170
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8128
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8128
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8071
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8071
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8058
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8058
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7966
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7966
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7926
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7926
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7918
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7918
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7897
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7897
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7885
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7885
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7883
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7883
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7810
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7810
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7792
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7792
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7789
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7789
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7765
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7765
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7763
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7763
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7751
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7751
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7734
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7734
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7716
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7716
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7702
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7702
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7698
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7698
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7691
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7691
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7690
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7690
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7652
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7652
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7648
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7648
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7624
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7624
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7602
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7602
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7599
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7599
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7568
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7568
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7519
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7519
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7466
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7466
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7430
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7430
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7421
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7421
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7411
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7411
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7390
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7390
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7381
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7381
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7370
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7370
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7364
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7364
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7355
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7355
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7342
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7342
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7337
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7337
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7306
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7306
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7302
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7302
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7289
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7289
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7255
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7255
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7237
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7237
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7230
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7230
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7229
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7229
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7218
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7218
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7189
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7189
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7167
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7167
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7125
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7125
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7100
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7100
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7083
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7083
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7081
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7081
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7063
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7063
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7057
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7057
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7036
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7036
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7032
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7032
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7030
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7030
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7019
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7019
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7003
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7003

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