(R)-5-hydroxy-2',4',5'-trimethoxy-2",2"-dimethylpyrano[5",6":6,7]isoflavanone - Compound Card

(R)-5-hydroxy-2',4',5'-trimethoxy-2",2"-dimethylpyrano[5",6":6,7]isoflavanone

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(R)-5-hydroxy-2',4',5'-trimethoxy-2",2"-dimethylpyrano[5",6":6,7]isoflavanone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavonoid
Canonical Smiles COc1cc(OC)c(cc1[C@@H]1COc2c(C1=O)c(O)c1c(c2)OC(C=C1)(C)C)OC
InChI InChI=1S/C23H24O7/c1-23(2)7-6-12-16(30-23)10-19-20(21(12)24)22(25)14(11-29-19)13-8-17(27-4)18(28-5)9-15(13)26-3/h6-10,14,24H,11H2,1-5H3/t14-/m0/s1
InChIKey IFQCOXCDQXGBFK-AWEZNQCLSA-N
Formula C23H24O7
HBA 7
HBD 1
MW 412.44
Rotatable Bonds 4
TPSA 83.45
LogP 3.96
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 412.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina sacleuxii Leguminosae/Fabaceae Plantae 1899109
2 Erythrina sacleuxii Leguminosae/Fabaceae Plantae 1899109
3 Erythrina schliebenii Leguminosae/Fabaceae Plantae 2590720

Showing of synonyms

  • Andayi AW, Yenesew A, et al. (2006). Antiplasmodial flavonoids from Erythrina sacleuxii.. Planta Medica,2006,72(2),187-189. [View] [PubMed]
  • Nyandoro SS, Munissi JJ, et al. (2017). Flavonoids from Erythrina schliebenii.. Journal of Natural Products,2017,80(2),377-383. [View] [PubMed]
  • Yenesew A, Midiwo JO, et al. (2000). Two isoflavanones from the stem bark of Erythrina sacleuxii.. Phytochemistry,2000,55(5),457-459. [View] [PubMed]
Pubchem: 12971611
Nmrshiftdb2: 60073003

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c2)c1cc(c23)OCC(C3=O)c4ccccc4

Level: 1

Mol. Weight: 412.44 g/mol

Structure

SMILES: O=C1CCOc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 412.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 412.44 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
67.74
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
8.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.540
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.670
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.070
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
-25.100
Rat (Acute)
2.600
Rat (Chronic Oral)
2.260
Fathead Minnow
5.090
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
471.840
Hydration Free Energy
-5.230
Log(D) at pH=7.4
3.600
Log(P)
4.44
Log S
-5.77
Log(Vapor Pressure)
-8.27
Melting Point
168.21
pKa Acid
7.89
pKa Basic
3.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9201
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9201
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.9110
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.9110
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8875
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8875
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8866
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8866
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8670
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8670
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8625
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8625
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8623
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8623
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8587
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8587
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8339
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8339
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8274
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8274
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8166
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8166
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8112
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8112
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8086
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8086
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8028
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8028
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7995
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7995
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7922
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7922
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7890
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7890
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7880
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7880
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7865
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7865
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7720
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7720
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7704
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7704
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7694
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7694
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7553
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7553
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7515
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7515
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7491
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7491
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7488
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7488
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7469
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7469
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7427
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7427
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7416
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7416
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7374
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7374
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7371
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7371
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7353
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7353
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7282
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7282
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7270
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7270
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7268
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7268
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7264
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7264
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7226
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7226
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7216
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7216
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7200
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7200
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7194
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7194
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7173
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7173
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7149
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7149
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7116
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7116
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7096
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7096
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7096
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7096
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7071
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7071
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7020
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7020
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7007
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7007
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7000
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7000

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