(S)-3,5-dihydroxy-2',7-dimethoxy-2'',2''-dimethylpyrano[5'',6'':3',4']isoflavanone - Compound Card

(S)-3,5-dihydroxy-2',7-dimethoxy-2'',2''-dimethylpyrano[5'',6'':3',4']isoflavanone

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(S)-3,5-dihydroxy-2',7-dimethoxy-2'',2''-dimethylpyrano[5'',6'':3',4']isoflavanone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1cc(O)c2c(c1)OC[C@@](C2=O)(O)c1ccc2c(c1OC)C=CC(O2)(C)C
InChI InChI=1S/C22H22O7/c1-21(2)8-7-13-16(29-21)6-5-14(19(13)27-4)22(25)11-28-17-10-12(26-3)9-15(23)18(17)20(22)24/h5-10,23,25H,11H2,1-4H3/t22-/m1/s1
InChIKey DBYYEVTTXJMFLT-JOCHJYFZSA-N
Formula C22H22O7
HBA 7
HBD 2
MW 398.41
Rotatable Bonds 3
TPSA 94.45
LogP 3.06
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 398.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dalbergia melanoxylon Leguminosae/Fabaceae Plantae 114981

Showing of synonyms

  • Mutai P, Heydenreich M, et al. (2013). 3-Hydroxyisoflavanones from the stem bark of Dalbergia melanoxylon: Isolation, antimycobacterial evaluation and molecular docking studies.. Phytochemistry Letters,2013,30,6(4),671-675. [View] [PubMed]
Pubchem: 102105358

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OCC(C2=O)c(c3)ccc(c34)OCC=C4

Level: 1

Mol. Weight: 398.41 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 398.41 g/mol

Structure

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 398.41 g/mol

Antimycobacterial

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.140
Plasma Protein Binding
66.95
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.990
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.710
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-13.460
Rat (Acute)
2.510
Rat (Chronic Oral)
2.370
Fathead Minnow
4.710
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
443.800
Hydration Free Energy
-7.100
Log(D) at pH=7.4
3.280
Log(P)
3.94
Log S
-5.08
Log(Vapor Pressure)
-8.24
Melting Point
172.43
pKa Acid
7.73
pKa Basic
3.85
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 0.9402
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9402
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9343
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9343
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9114
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9114
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8751
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8751
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8647
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8647
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8573
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8573
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8497
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8497
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8490
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8490
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8485
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8485
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8474
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8474
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8320
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8320
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8289
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8289
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8228
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8228
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8170
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8170
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8088
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8088
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8080
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8080
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8071
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8071
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8053
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8053
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8045
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8045
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8023
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8023
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8022
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8022
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8006
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8006
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7961
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7961
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7960
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7960
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7843
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7843
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7837
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7837
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7798
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7798
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7772
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7772
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7764
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7764
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7731
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7731
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7715
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7715
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7681
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7681
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7676
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7676
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7659
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7659
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 3 0.7655
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 3 0.7655
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7637
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7637
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7634
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7634
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7592
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7592
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7572
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7572
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7569
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7569
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7533
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7533
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7530
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7530
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7519
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7519
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7493
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7493
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7479
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7479
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7374
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7374
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7361
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7361
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7337
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7337
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7333
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7333
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7300
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7300
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7298
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7298
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7286
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7286
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7285
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7285
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7281
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7281
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7259
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7259
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7253
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7253
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7251
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7251
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7242
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7242
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7221
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7221
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7203
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7203
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7200
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7200
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7160
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7160
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7156
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7156
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7136
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7136
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7135
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7135
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7132
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7132
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7114
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7114
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7095
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7095
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7089
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7089
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7083
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7083
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7062
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7062
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7053
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7053
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7032
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7032
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7032
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7032
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7028
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7028
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7017
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7017

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