5, 4'-dihydroxy-6-(3"'-methylbut-2"'-enyl)-2"-hydroxyisopropyl dihydrofurano [4",5":8,7] isoflavone - Compound Card

5, 4'-dihydroxy-6-(3"'-methylbut-2"'-enyl)-2"-hydroxyisopropyl dihydrofurano [4",5":8,7] isoflavone

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5, 4'-dihydroxy-6-(3"'-methylbut-2"'-enyl)-2"-hydroxyisopropyl dihydrofurano [4",5":8,7] isoflavone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles CC(=CCc1c2OC(Cc2c2c(c1O)c(=O)c(co2)c1ccc(cc1)O)C(O)(C)C)C
InChI InChI=1S/C25H26O6/c1-13(2)5-10-16-21(27)20-22(28)18(14-6-8-15(26)9-7-14)12-30-24(20)17-11-19(25(3,4)29)31-23(16)17/h5-9,12,19,26-27,29H,10-11H2,1-4H3
InChIKey KQLMUJOKBRYEHR-UHFFFAOYSA-N
Formula C25H26O6
HBA 6
HBD 3
MW 422.48
Rotatable Bonds 4
TPSA 100.13
LogP 4.45
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 422.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina lysistemon Leguminosae/Fabaceae Plantae 347910

Showing of synonyms

  • El-Masry S, Amer ME, et al. (2002). Prenylated flavonoids of Erythrina lysistemon grown in Egypt. Phytochemistry,2002,60(8),783-787. [View] [PubMed]
Pubchem: 402594
Nmrshiftdb2: 70015543

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)ccc3c2occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 422.48 g/mol

Structure

SMILES: C1COc(c12)ccc3c2occc3=O

Level: 0

Mol. Weight: 422.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 422.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.07
Plasma Protein Binding
79.71
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
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.81
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.7
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.15
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.67
Micronucleos
Toxic
NR-AhR
Safe
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
-42.43
Rat (Acute)
2.59
Rat (Chronic Oral)
1.87
Fathead Minnow
5.26
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
529.48
Hydration Free Energy
-4.78
Log(D) at pH=7.4
3.67
Log(P)
5.13
Log S
-5.66
Log(Vapor Pressure)
-10.62
Melting Point
245.85
pKa Acid
7.78
pKa Basic
6.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9741
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9741
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9502
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9502
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9247
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9247
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9102
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9102
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8944
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8944
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8851
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8851
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 4 0.8738
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 4 0.8738
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8661
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8661
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8639
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8639
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8387
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8387
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8369
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8369
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8248
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8248
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8163
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8163
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8156
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8156
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8016
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8016
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7983
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7983
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7963
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7963
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7868
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7868
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7855
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7855
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7845
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7845
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7740
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7740
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7735
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7735
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7724
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7724
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.7718
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.7718
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7678
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7678
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7632
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7632
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7621
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7621
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7605
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7605
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7563
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7563
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7535
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7535
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7526
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7526
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7504
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7504
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7496
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7496
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7476
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7476
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7455
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7455
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7418
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7418
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7415
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7415
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7414
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7414
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7406
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7406
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7397
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7397
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7395
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7395
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7395
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7395
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7394
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7394
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7381
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7381
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7365
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7365
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7361
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7361
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7355
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7355
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7346
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7346
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7318
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7318
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7315
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7315
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7313
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7313
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7310
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7310
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7253
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7253
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7243
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7243
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7243
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7243
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7230
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7230
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7223
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7223
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7219
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7219
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7217
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7217
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7207
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7207
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7206
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7206
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7200
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7200
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7191
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7191
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7187
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7187
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7185
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7185
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7165
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7165
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7142
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7142
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7116
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7116
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7093
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7093
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7092
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7092
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7087
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7087
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7074
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7074
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7056
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7056
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7054
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7054
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7018
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7018
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7004
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7004

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