Alpinumisoflavone - Compound Card

Alpinumisoflavone

Select a section from the left sidebar

Alpinumisoflavone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles Oc1ccc(cc1)c1coc2c(c1=O)c(O)c1c(c2)OC(C=C1)(C)C
InChI InChI=1S/C20H16O5/c1-20(2)8-7-13-15(25-20)9-16-17(18(13)22)19(23)14(10-24-16)11-3-5-12(21)6-4-11/h3-10,21-22H,1-2H3
InChIKey RQAMSFTXEFSBPK-UHFFFAOYSA-N
Formula C20H16O5
HBA 5
HBD 2
MW 336.34
Rotatable Bonds 1
TPSA 79.9
LogP 4.06
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 336.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina lysistemon Leguminosae/Fabaceae Plantae 347910
2 Erythrina lysistemon Leguminosae/Fabaceae Plantae 347910
3 Erythrina lysistemon Leguminosae/Fabaceae Plantae 347910
4 Ficus thonningii Moraceae Plantae 309310

Showing of synonyms

  • Mvondo MA, Njamen D, et al. (2011). A postmenopause-like model of ovariectomized Wistar rats to identify active principles of Erythrina lysistemon (Fabaceae).. Fitoterapia,2011, 82(7), 939-949. [View] [PubMed]
  • Fongang Y, Bankeu J, et al. (2015). Flavonoids and other bioactive constituents from Ficus thonningii Blume (Moraceae). Phytochemistry Letters, 2015, 11, 139-145. [View]
  • Magne Nde CB, Njamen D, et al. (2012). In vitro estrogenic activity of two major compounds from the stem bark of Erythrina lysistemon (Fabaceae). European journal of pharmacology, 2012, 674(2-3), 87–94. [View]
  • 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: 5490139
Chebi: 69746
Nmrshiftdb2: 20146192
Metabolights: MTBLC69746
Bindingdb: 50200542
CPRiL: 56921
Structure

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

Level: 1

Mol. Weight: 336.34 g/mol

Structure

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

Level: 0

Mol. Weight: 336.34 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 336.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.070
Plasma Protein Binding
71.81
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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.010
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.860
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.450
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.030
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
2.300
Rat (Acute)
2.990
Rat (Chronic Oral)
2.220
Fathead Minnow
4.850
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
474.870
Hydration Free Energy
-11.820
Log(D) at pH=7.4
4.310
Log(P)
4.55
Log S
-5.77
Log(Vapor Pressure)
-9.33
Melting Point
266.25
pKa Acid
7.24
pKa Basic
4.79
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 0.9696
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9696
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9496
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9496
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.9376
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.9376
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9094
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9094
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8959
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8959
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8863
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8863
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8855
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8855
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8751
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8751
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8741
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8741
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8608
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8608
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8568
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8568
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8567
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8567
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8561
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8561
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8551
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8551
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8542
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8542
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8499
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8499
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8423
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8423
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8326
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8326
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8160
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8160
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8076
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8076
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8059
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8059
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8056
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8056
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7952
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7952
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7913
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7913
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7863
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7863
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7845
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7845
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7786
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7786
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7753
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7753
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7740
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7740
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7725
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7725
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7702
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7702
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7642
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7642
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7626
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7626
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7618
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7618
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7599
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7599
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7537
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7537
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7504
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7504
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7504
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7504
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7484
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7484
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7451
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7451
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7429
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7429
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7422
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7422
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7404
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7404
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7381
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7381
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7376
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7376
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7371
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7371
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7309
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7309
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7297
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7297
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7293
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7293
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7291
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7291
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7260
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7260
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7234
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7234
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7226
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7226
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7204
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7204
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7189
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7189
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7185
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7185
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7168
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7168
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7157
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7157
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7139
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7139
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7136
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7136
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7102
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7102
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7092
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7092
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7073
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7073
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7064
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7064
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7049
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7049
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7048
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7048
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7028
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7028

Download SDF