UCSF

ZINC03871576

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
October 4th, 2005 20 Yes

Popular Name: Apigenin Apigenin

Find On: PubMed — Wikipedia — Google

CAS Numbers: 263711-74-6 , 520-36-5 , 8002-66-2 , [520-36-5]

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 2.46 1.12 -12.82 3 5 0 91 270.24 1 ↓
Mid Mid (pH 6-8) 2.72 1.4 -45.92 2 5 -1 94 269.232 1 ↓

Vendor Notes

Note Type Comments Provided By
biological_source Found free or as glycosides in the stems, roots, leaves, seeds or fruit of a very wide range of plant spp. Found also in some fossil leaf tissues ZereneX Building Blocks
biological_use Shows antineoplastic activity in vitro ZereneX Building Blocks
ALOGPS_SOLUBILITY 1.18e-01 g/l DrugBank-experimental
MP 345 - 350 °C Fluorochem
MP 345-350o C Indofine
MP 355-358o C Indofine
M.P. >350C (dec) Indofine
Purity >95% Fluorochem
therap antispasmodic, antineoplastic, topoisomerase I inhibitor MicroSource Spectrum
biological_use Antispasmolytic agent IBScreen Bioactives
Melting_Point ca 315? dec. Alfa-Aesar
Melting_Point ca 315° dec. Alfa-Aesar
Patent Database Links EP1523982; EP1550462; EP1600061; EP1808169; EP1808172; EP1834636; EP1842541; EP1911358; EP1925311; US2002048798; US2006135585; US2007184133; US2007191330; US2007202195; US2007212393; US2007224296; US2007232698; US2008262080; WO2005020981; WO2006121518; WO ChEBI
UniProt Database Links FNSI_PETCR; FOMT2_WHEAT; GBA3_HUMAN; I7GT1_SOYBN; OMT15_ORYSJ; OMT17_ORYSJ; OMT1_CHRAE; OMT2_CHRAE; SOMT2_SOYBN; SOT5_ARATH; TPS3_MATRE; U73B2_ARATH; UBGAT_SCUBA; UGFGT_MEDTR ChEBI
UniProt Database Links FNSI_PETCR; FOMT2_WHEAT; GBA3_HUMAN; I7GT1_SOYBN; OMT15_ORYSJ; OMT17_ORYSJ; OMT1_CHRAE; OMT2_CHRAE; SOMT2_SOYBN; SOT5_ARATH; U73B2_ARATH; UBGAT_SCUBA; UGFGT_MEDTR ChEBI
Target G1/S-specific cyclin-D1(P24385)&Cyclin-dependent kinase inhibitor 1(P38936)&Cell division protein kinase 4(P11802)&NAD(P)H dehydrogenase [quinone] 1(P15559)&DNA topoisomerase 1(P11387)&Transcription factor AP-1(P05412)&Cyclic AMP-responsive element-bindin Herbal Ingredients Targets
Target P450 Selleck Chemicals
biological_use Shows antineoplastic activity in vitro IBScreen Bioactives IBScreen Bioactives
SOLUBILITY Soluble in Ethylformiate/acetone/toluene Indofine
SOLUBILITY Soluble in Methanol Indofine
mechanism Tyrosine kinase inhibitor IBScreen Bioactives
APPEARANCE Yellow crystals Indofine

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
AA1R-2-E Adenosine A1 Receptor (cluster #2 Of 4), Eukaryotic Eukaryotes 3000 0.39 Binding ≤ 10μM
AA2AR-3-E Adenosine A2a Receptor (cluster #3 Of 4), Eukaryotic Eukaryotes 7580 0.36 Binding ≤ 10μM
ABCG2-1-E ATP-binding Cassette Sub-family G Member 2 (cluster #1 Of 2), Eukaryotic Eukaryotes 5900 0.37 Binding ≤ 10μM
ALDR-1-E Aldose Reductase (cluster #1 Of 5), Eukaryotic Eukaryotes 6670 0.36 Binding ≤ 10μM
AOFA-4-E Monoamine Oxidase A (cluster #4 Of 8), Eukaryotic Eukaryotes 1700 0.40 Binding ≤ 10μM
BGLR-1-E Beta-glucuronidase (cluster #1 Of 2), Eukaryotic Eukaryotes 2800 0.39 Binding ≤ 10μM
CCNB1-1-E G2/mitotic-specific Cyclin B1 (cluster #1 Of 2), Eukaryotic Eukaryotes 4000 0.38 Binding ≤ 10μM
CCNB2-1-E G2/mitotic-specific Cyclin B2 (cluster #1 Of 2), Eukaryotic Eukaryotes 4000 0.38 Binding ≤ 10μM
CCNB3-1-E G2/mitotic-specific Cyclin B3 (cluster #1 Of 2), Eukaryotic Eukaryotes 4000 0.38 Binding ≤ 10μM
CDK1-1-E Cyclin-dependent Kinase 1 (cluster #1 Of 4), Eukaryotic Eukaryotes 4000 0.38 Binding ≤ 10μM
CDK6-1-E Cyclin-dependent Kinase 6 (cluster #1 Of 1), Eukaryotic Eukaryotes 1700 0.40 Binding ≤ 10μM
CP19A-3-E Cytochrome P450 19A1 (cluster #3 Of 3), Eukaryotic Eukaryotes 900 0.42 Binding ≤ 10μM
CP1B1-1-E Cytochrome P450 1B1 (cluster #1 Of 1), Eukaryotic Eukaryotes 25 0.53 Binding ≤ 10μM
CSK21-2-E Casein Kinase II Alpha (cluster #2 Of 3), Eukaryotic Eukaryotes 800 0.43 Binding ≤ 10μM
CSK2B-3-E Casein Kinase II Beta (cluster #3 Of 3), Eukaryotic Eukaryotes 4290 0.38 Binding ≤ 10μM
DHB1-1-E Estradiol 17-beta-dehydrogenase 1 (cluster #1 Of 1), Eukaryotic Eukaryotes 710 0.43 Binding ≤ 10μM
ESR1-1-E Estrogen Receptor Alpha (cluster #1 Of 5), Eukaryotic Eukaryotes 660 0.43 Binding ≤ 10μM
ESR2-4-E Estrogen Receptor Beta (cluster #4 Of 4), Eukaryotic Eukaryotes 660 0.43 Binding ≤ 10μM
GBRA1-1-E GABA Receptor Alpha-1 Subunit (cluster #1 Of 8), Eukaryotic Eukaryotes 3020 0.39 Binding ≤ 10μM
GBRA2-1-E GABA Receptor Alpha-2 Subunit (cluster #1 Of 8), Eukaryotic Eukaryotes 3020 0.39 Binding ≤ 10μM
GBRA3-1-E GABA Receptor Alpha-3 Subunit (cluster #1 Of 8), Eukaryotic Eukaryotes 3020 0.39 Binding ≤ 10μM
GBRA4-1-E GABA Receptor Alpha-4 Subunit (cluster #1 Of 7), Eukaryotic Eukaryotes 3020 0.39 Binding ≤ 10μM
GBRA5-1-E GABA Receptor Alpha-5 Subunit (cluster #1 Of 8), Eukaryotic Eukaryotes 3020 0.39 Binding ≤ 10μM
GBRA6-6-E GABA Receptor Alpha-6 Subunit (cluster #6 Of 8), Eukaryotic Eukaryotes 3020 0.39 Binding ≤ 10μM
GSK3A-1-E Glycogen Synthase Kinase-3 Alpha (cluster #1 Of 3), Eukaryotic Eukaryotes 1400 0.41 Binding ≤ 10μM
GSK3B-7-E Glycogen Synthase Kinase-3 Beta (cluster #7 Of 7), Eukaryotic Eukaryotes 1400 0.41 Binding ≤ 10μM
MRP1-1-E Multidrug Resistance-associated Protein 1 (cluster #1 Of 1), Eukaryotic Eukaryotes 2400 0.39 Binding ≤ 10μM
NOX4-1-E NADPH Oxidase 4 (cluster #1 Of 1), Eukaryotic Eukaryotes 1130 0.42 Binding ≤ 10μM
P90584-1-E Protein Kinase Pfmrk (cluster #1 Of 2), Eukaryotic Eukaryotes 7000 0.36 Binding ≤ 10μM
PGH2-4-E Cyclooxygenase-2 (cluster #4 Of 8), Eukaryotic Eukaryotes 8000 0.36 Binding ≤ 10μM
XDH-2-E Xanthine Dehydrogenase (cluster #2 Of 2), Eukaryotic Eukaryotes 700 0.43 Binding ≤ 10μM
ANDR-1-E Androgen Receptor (cluster #1 Of 3), Eukaryotic Eukaryotes 5200 0.37 Functional ≤ 10μM
CP1A1-1-E Cytochrome P450 1A1 (cluster #1 Of 3), Eukaryotic Eukaryotes 427 0.45 ADME/T ≤ 10μM
CP1A2-1-E Cytochrome P450 1A2 (cluster #1 Of 3), Eukaryotic Eukaryotes 795 0.43 ADME/T ≤ 10μM
CP1B1-1-E Cytochrome P450 1B1 (cluster #1 Of 3), Eukaryotic Eukaryotes 64 0.50 ADME/T ≤ 10μM
Z104294-2-O Cyclin-dependent Kinase 5/CDK5 Activator 1 (cluster #2 Of 2), Other Other 1600 0.41 Binding ≤ 10μM
Z104301-4-O GABA-A Receptor; Anion Channel (cluster #4 Of 8), Other Other 770 0.43 Binding ≤ 10μM
Z50597-1-O Rattus Norvegicus (cluster #1 Of 12), Other Other 3400 0.38 Functional ≤ 10μM
Z50607-3-O Human Immunodeficiency Virus 1 (cluster #3 Of 10), Other Other 9000 0.35 Functional ≤ 10μM
Z50652-3-O Influenza A Virus (cluster #3 Of 4), Other Other 4740 0.37 Functional ≤ 10μM
Z80418-2-O RAW264.7 (Monocytic-macrophage Leukemia Cells) (cluster #2 Of 9), Other Other 7700 0.36 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
CSK21_HUMAN P68400 Casein Kinase II Alpha, Human 740 0.43 Binding ≤ 1μM
CP19A_HUMAN P11511 Cytochrome P450 19A1, Human 1000 0.42 Binding ≤ 1μM
CP1B1_HUMAN Q16678 Cytochrome P450 1B1, Human 25 0.53 Binding ≤ 1μM
DHB1_HUMAN P14061 Estradiol 17-beta-dehydrogenase 1, Human 710 0.43 Binding ≤ 1μM
ESR1_HUMAN P03372 Estrogen Receptor Alpha, Human 660 0.43 Binding ≤ 1μM
ESR2_HUMAN Q92731 Estrogen Receptor Beta, Human 130 0.48 Binding ≤ 1μM
Z104301 Z104301 GABA-A Receptor; Anion Channel 770 0.43 Binding ≤ 1μM
XDH_HUMAN P47989 Xanthine Dehydrogenase, Human 700 0.43 Binding ≤ 1μM
AA1R_RAT P25099 Adenosine A1 Receptor, Rat 3000 0.39 Binding ≤ 10μM
AA2AR_RAT P30543 Adenosine A2a Receptor, Rat 7580 0.36 Binding ≤ 10μM
ALDR_RAT P07943 Aldose Reductase, Rat 6670 0.36 Binding ≤ 10μM
ABCG2_HUMAN Q9UNQ0 ATP-binding Cassette Sub-family G Member 2, Human 3100 0.39 Binding ≤ 10μM
BGLR_RAT P06760 Beta-glucuronidase, Rat 2800 0.39 Binding ≤ 10μM
CSK21_HUMAN P68400 Casein Kinase II Alpha, Human 10000 0.35 Binding ≤ 10μM
CSK2B_HUMAN P67870 Casein Kinase II Beta, Human 10000 0.35 Binding ≤ 10μM
CDK1_HUMAN P06493 Cyclin-dependent Kinase 1, Human 4000 0.38 Binding ≤ 10μM
Z104294 Z104294 Cyclin-dependent Kinase 5/CDK5 Activator 1 1600 0.41 Binding ≤ 10μM
CDK6_HUMAN Q00534 Cyclin-dependent Kinase 6, Human 1700 0.40 Binding ≤ 10μM
PGH2_HUMAN P35354 Cyclooxygenase-2, Human 8000 0.36 Binding ≤ 10μM
CP19A_HUMAN P11511 Cytochrome P450 19A1, Human 1000 0.42 Binding ≤ 10μM
CP1B1_HUMAN Q16678 Cytochrome P450 1B1, Human 25 0.53 Binding ≤ 10μM
DHB1_HUMAN P14061 Estradiol 17-beta-dehydrogenase 1, Human 710 0.43 Binding ≤ 10μM
ESR1_HUMAN P03372 Estrogen Receptor Alpha, Human 1253 0.41 Binding ≤ 10μM
ESR2_HUMAN Q92731 Estrogen Receptor Beta, Human 130 0.48 Binding ≤ 10μM
CCNB1_HUMAN P14635 G2/mitotic-specific Cyclin B1, Human 4000 0.38 Binding ≤ 10μM
CCNB2_HUMAN O95067 G2/mitotic-specific Cyclin B2, Human 4000 0.38 Binding ≤ 10μM
CCNB3_HUMAN Q8WWL7 G2/mitotic-specific Cyclin B3, Human 4000 0.38 Binding ≤ 10μM
GBRA1_HUMAN P14867 GABA Receptor Alpha-1 Subunit, Human 3019.95172 0.39 Binding ≤ 10μM
GBRA2_HUMAN P47869 GABA Receptor Alpha-2 Subunit, Human 3019.95172 0.39 Binding ≤ 10μM
GBRA3_HUMAN P34903 GABA Receptor Alpha-3 Subunit, Human 3019.95172 0.39 Binding ≤ 10μM
GBRA4_HUMAN P48169 GABA Receptor Alpha-4 Subunit, Human 3019.95172 0.39 Binding ≤ 10μM
GBRA5_HUMAN P31644 GABA Receptor Alpha-5 Subunit, Human 3019.95172 0.39 Binding ≤ 10μM
GBRA6_HUMAN Q16445 GABA Receptor Alpha-6 Subunit, Human 3019.95172 0.39 Binding ≤ 10μM
Z104301 Z104301 GABA-A Receptor; Anion Channel 770 0.43 Binding ≤ 10μM
GSK3A_HUMAN P49840 Glycogen Synthase Kinase-3 Alpha, Human 1400 0.41 Binding ≤ 10μM
GSK3B_HUMAN P49841 Glycogen Synthase Kinase-3 Beta, Human 1400 0.41 Binding ≤ 10μM
AOFA_HUMAN P21397 Monoamine Oxidase A, Human 1700 0.40 Binding ≤ 10μM
MRP1_HUMAN P33527 Multidrug Resistance-associated Protein 1, Human 2400 0.39 Binding ≤ 10μM
NOX4_HUMAN Q9NPH5 NADPH Oxidase 4, Human 1130 0.42 Binding ≤ 10μM
P90584_PLAFA P90584 Protein Kinase Pfmrk, Plafa 7000 0.36 Binding ≤ 10μM
XDH_HUMAN P47989 Xanthine Dehydrogenase, Human 700 0.43 Binding ≤ 10μM
ANDR_HUMAN P10275 Androgen Receptor, Human 5200 0.37 Functional ≤ 10μM
Z50607 Z50607 Human Immunodeficiency Virus 1 9000 0.35 Functional ≤ 10μM
Z50652 Z50652 Influenza A Virus 4740 0.37 Functional ≤ 10μM
Z50597 Z50597 Rattus Norvegicus 3400 0.38 Functional ≤ 10μM
Z80418 Z80418 RAW264.7 (Monocytic-macrophage Leukemia Cells) 500 0.44 Functional ≤ 10μM
CP1A1_HUMAN P04798 Cytochrome P450 1A1, Human 390 0.45 ADME/T ≤ 10μM
CP1A2_HUMAN P05177 Cytochrome P450 1A2, Human 795 0.43 ADME/T ≤ 10μM
CP1B1_HUMAN Q16678 Cytochrome P450 1B1, Human 64 0.50 ADME/T ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
Abacavir transmembrane transport
ABC-family proteins mediated transport
Activation of NIMA Kinases NEK9, NEK6, NEK7
Adenosine P1 receptors
Aflatoxin activation and detoxification
AKT phosphorylates targets in the cytosol
APC truncation mutants have impaired AXIN binding
APC/C:Cdc20 mediated degradation of Cyclin B
Aromatic amines can be N-hydroxylated or N-dealkylated by CYP1A2
AXIN missense mutants destabilize the destruction complex
Beta-catenin phosphorylation cascade
Chk1/Chk2(Cds1) mediated inactivation of Cyclin B:Cdk1 complex
Cobalamin (Cbl, vitamin B12) transport and metabolism
Condensation of Prometaphase Chromosomes
Condensation of Prophase Chromosomes
Constitutive PI3K/AKT Signaling in Cancer
CRMPs in Sema3A signaling
Cyclin A/B1 associated events during G2/M transition
Cyclin B2 mediated events
Cyclin D associated events in G1
Degradation of beta-catenin by the destruction complex
Depolymerisation of the Nuclear Lamina
disassembly of the destruction complex and recruitment of AXIN to the membrane
E2F mediated regulation of DNA replication
E2F-enabled inhibition of pre-replication complex formation
Endogenous sterols
Enzymatic degradation of dopamine by COMT
Enzymatic degradation of Dopamine by monoamine oxidase
ERK1 activation
Estrogen biosynthesis
G alpha (i) signalling events
G alpha (s) signalling events
G0 and Early G1
G1/S-Specific Transcription
G2/M DNA replication checkpoint
GABA A receptor activation
Golgi Cisternae Pericentriolar Stack Reorganization
Iron uptake and transport
Ligand-gated ion channel transport
Loss of Nlp from mitotic centrosomes
Loss of proteins required for interphase microtubule organization from the ce
MASTL Facilitates Mitotic Progression
Metabolism of serotonin
Methylation
misspliced GSK3beta mutants stabilize beta-catenin
Monoamines are oxidized to aldehydes by MAOA and MAOB, producing NH3 and H2O2
NGF-independant TRKA activation
Nicotinamide salvaging
Norepinephrine Neurotransmitter Release Cycle
Nuclear Pore Complex (NPC) Disassembly
Nuclear Receptor transcription pathway
Nuclear signaling by ERBB4
Oncogene Induced Senescence
Oxidative Stress Induced Senescence
Phosphorylation of Emi1
Phosphorylation of proteins involved in the G2/M transition by Cyclin A:Cdc2 com
Phosphorylation of the APC/C
Polo-like kinase mediated events
PPARA activates gene expression
Pregnenolone biosynthesis
Purine catabolism
Recruitment of mitotic centrosome proteins and complexes
Recruitment of NuMA to mitotic centrosomes
Regulation of APC/C activators between G1/S and early anaphase
Regulation of HSF1-mediated heat shock response
Regulation of PLK1 Activity at G2/M Transition
Resolution of Sister Chromatid Cohesion
S33 mutants of beta-catenin aren't phosphorylated
S37 mutants of beta-catenin aren't phosphorylated
S45 mutants of beta-catenin aren't phosphorylated
Senescence-Associated Secretory Phenotype (SASP)
Signal transduction by L1
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE)
Synthesis of 15-eicosatetraenoic acid derivatives
Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET)
Synthesis of Leukotrienes (LT) and Eoxins (EX)
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)
T41 mutants of beta-catenin aren't phosphorylated
The canonical retinoid cycle in rods (twilight vision)
truncations of AMER1 destabilize the destruction complex
WNT mediated activation of DVL
XBP1(S) activates chaperone genes
Xenobiotics

Analogs ( Draw Identity 99% 90% 80% 70% )

No pre-computed analogs available. Try a structural similarity search.