4'',5''-dihydro-2'-methoxy-5,4'-dihydroxy-5''-isopropenylfurano-(2'',3'';7,6)-isoflavanone - Compound Card

4'',5''-dihydro-2'-methoxy-5,4'-dihydroxy-5''-isopropenylfurano-(2'',3'';7,6)-isoflavanone

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4'',5''-dihydro-2'-methoxy-5,4'-dihydroxy-5''-isopropenylfurano-(2'',3'';7,6)-isoflavanone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavanone
Canonical Smiles COc1cc(O)ccc1C1COc2c(C1=O)c(O)c1c(c2)OC(C1)C(=C)C
InChI InChI=1S/C21H20O6/c1-10(2)15-7-13-17(27-15)8-18-19(20(13)23)21(24)14(9-26-18)12-5-4-11(22)6-16(12)25-3/h4-6,8,14-15,22-23H,1,7,9H2,2-3H3
InChIKey HRRLYEDDDAJRSW-UHFFFAOYSA-N
Formula C21H20O6
HBA 6
HBD 2
MW 368.39
Rotatable Bonds 3
TPSA 85.22
LogP 3.34
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 368.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Desmodium uncinatum Leguminosae/Fabaceae Plantae 225101
2 Desmodium uncinatum Leguminosae/Fabaceae Plantae 225101

Showing of synonyms

  • Guchu SM, Yenesew A, et al. (2007). C-methylated and C-prenylated isoflavonoids from root extract of Desmodium uncinatum.. Phytochemistry,2007,68(5),646-651. [View] [PubMed]
  • Tsanuo MK, Hassanali A, et al. (2003). Isoflavanones from the allelopathic aqueous root exudate of Desmodium uncinatum. Phytochemistry,2003,64(1),265-273. [View] [PubMed]
Pubchem: 10981449
Nmrshiftdb2: 20000540

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)cc3c(c2)C(=O)C(CO3)c4ccccc4

Level: 1

Mol. Weight: 368.39 g/mol

Structure

SMILES: C1COc(c12)cc3c(c2)C(=O)CCO3

Level: 0

Mol. Weight: 368.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 368.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.780
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
51.81
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
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.160
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.230
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.890
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.160
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
Toxic
T. Pyriformis
-3.920
Rat (Acute)
2.540
Rat (Chronic Oral)
2.430
Fathead Minnow
4.850
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
450.000
Hydration Free Energy
-7.260
Log(D) at pH=7.4
3.210
Log(P)
4.43
Log S
-5.56
Log(Vapor Pressure)
-9.02
Melting Point
180.31
pKa Acid
7.2
pKa Basic
4.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9251
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9251
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9213
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9213
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9044
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9044
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.9015
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.9015
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9003
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9003
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8966
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8966
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8850
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8850
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8793
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8793
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8791
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8791
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8771
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8771
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8689
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8689
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8499
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8499
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8459
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8459
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8445
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8445
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8404
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8404
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8389
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8389
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8377
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8377
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8299
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8299
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8144
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8144
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8135
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8135
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8112
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8112
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8105
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8105
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8057
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8057
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8039
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8039
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7948
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7948
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7937
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7937
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7924
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7924
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7914
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7914
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7887
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7887
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7863
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7863
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7845
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7845
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7736
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7736
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7582
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7582
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7543
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7543
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7516
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7516
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7453
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7453
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7446
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7446
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7404
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7404
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7359
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7359
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7354
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7354
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7307
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7307
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7303
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7303
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7287
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7287
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7269
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7269
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7260
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7260
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7239
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7239
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7211
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7211
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7210
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7210
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7160
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7160
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7137
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7137
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7136
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7136
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7096
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7096
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7090
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7090
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7060
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7060
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7045
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7045
dTDP-fucosamine acetyltransferase Q8FBQ3 WECD_ECOL6 Escherichia coli O6:H1 3 0.7023
dTDP-fucosamine acetyltransferase Q8FBQ3 WECD_ECOL6 Escherichia coli O6:H1 3 0.7023
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7016
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7016

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