5,4′-dihydroxy-8-(3,3-dimethylallyl)-2′′-hydroxymethyl-2′′-methylpyrano[5,6:6,7]isoflavone - Compound Card

5,4′-dihydroxy-8-(3,3-dimethylallyl)-2′′-hydroxymethyl-2′′-methylpyrano[5,6:6,7]isoflavone

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5,4′-dihydroxy-8-(3,3-dimethylallyl)-2′′-hydroxymethyl-2′′-methylpyrano[5,6:6,7]isoflavone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles OCC1(C)C=Cc2c(O1)c(CC=C(C)C)c1c(c2O)c(=O)c(co1)c1ccc(cc1)O
InChI InChI=1S/C25H24O6/c1-14(2)4-9-18-23-17(10-11-25(3,13-26)31-23)21(28)20-22(29)19(12-30-24(18)20)15-5-7-16(27)8-6-15/h4-8,10-12,26-28H,9,13H2,1-3H3
InChIKey HXAFJEIIUGRXPL-UHFFFAOYSA-N
Formula C25H24O6
HBA 6
HBD 3
MW 420.46
Rotatable Bonds 4
TPSA 100.13
LogP 4.54
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 420.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina mildbraedii Leguminosae/Fabaceae Plantae 2708827

Showing of synonyms

  • Tchokouaha RF, Alexi X, et al. (2010). Erymildbraedin A and B, two novel cytotoxic dimethylpyrano-isoflavones from the stem bark of Erythrina mildbraedii: evaluation of their activity toward endocrine cancer cells.. Journal of enzyme inhibition and medicinal chemistry,2010, 25(2), 228-233. [View] [PubMed]
Pubchem: 11718712

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c2)c1cc(c23)occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 420.46 g/mol

Structure

SMILES: O=c1ccoc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 420.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 420.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.32
Plasma Protein Binding
71.09
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.79
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.01
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
-42.46
Rat (Acute)
2.55
Rat (Chronic Oral)
2.48
Fathead Minnow
5.33
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
531.46
Hydration Free Energy
-4.53
Log(D) at pH=7.4
3.69
Log(P)
4.95
Log S
-5.63
Log(Vapor Pressure)
-10.5
Melting Point
220.99
pKa Acid
7.79
pKa Basic
6.91
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 0.9729
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9500
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9227
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9170
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9087
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8857
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8849
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.8714
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8656
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8623
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8622
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8447
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8384
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8377
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8276
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8261
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8165
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8093
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8022
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.8015
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7993
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7941
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7841
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7827
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7823
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7812
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7792
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7753
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7746
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7727
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7724
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7674
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7666
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7645
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7620
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7589
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7552
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7552
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7537
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7528
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7502
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7488
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7436
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7425
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7406
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7388
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7378
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7373
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7363
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7357
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7328
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7324
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7316
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7308
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7297
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7287
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7275
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7274
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7272
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7262
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7239
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.7225
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7192
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7187
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7155
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7124
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7095
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7094
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7094
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7070
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7067
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7057
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7055
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7053
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7044
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7037
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7025
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7007
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7002

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