Kaempferol 3-O-{3'',6''-di-O-[(E)-p-coumaroyl]-beta-D-glucopyranoside} - Compound Card

Kaempferol 3-O-{3'',6''-di-O-[(E)-p-coumaroyl]-beta-D-glucopyranoside}

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Kaempferol 3-O-{3'',6''-di-O-[(E)-p-coumaroyl]-beta-D-glucopyranoside}

Structure
Zoomed Structure
  • Family: Plantae - Thymelaeaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1OC1OC(OC(=O)/C=C/c2ccc(cc2)O)C(C(C1O)OC(=O)/C=C/c1ccc(cc1)O)O)O
InChI InChI=1S/C38H30O15/c39-22-9-1-19(2-10-22)5-15-28(44)50-35-32(47)37(51-29(45)16-6-20-3-11-23(40)12-4-20)53-38(33(35)48)52-36-31(46)30-26(43)17-25(42)18-27(30)49-34(36)21-7-13-24(41)14-8-21/h1-18,32-33,35,37-43,47-48H/b15-5+,16-6+
InChIKey JKXKHEWLIURKHG-IAGONARPSA-N
Formula C38H30O15
HBA 15
HBD 7
MW 726.64
Rotatable Bonds 9
TPSA 242.88
LogP 3.65
Number Rings 6
Number Aromatic Rings 5
Heavy Atom Count 53
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 726.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Thymelaea microphylla Thymelaeaceae Plantae 224056

Showing of synonyms

  • Kerbab K, Mekhelfi T, et al. (2015). Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. Et Dur. Nat Prod Res,2015,29(7),671-5. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OC(=O)C=Cc3ccccc3)OC(C2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OC(=O)C=Cc3ccccc3)OC(C2)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 726.64 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 726.64 g/mol

Structure

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 726.64 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 726.64 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 726.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.59
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
4.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1355.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.050
Plasma Protein Binding
53.39
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
9.950
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-33.190
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.350
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.830
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2461341.170
Rat (Acute)
2.410
Rat (Chronic Oral)
4.000
Fathead Minnow
3114.390
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
269122.700
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.960
Log(P)
4.79
Log S
-6.35
Log(Vapor Pressure)
-8892.6
Melting Point
267.81
pKa Acid
-33.8
pKa Basic
2.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9763
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9420
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9249
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9063
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.9062
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8959
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8930
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8836
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8683
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8571
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.8517
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8483
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8470
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8467
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8461
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.8428
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8388
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8325
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8241
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8239
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.8229
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8213
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8191
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8173
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8166
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 3 0.8063
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8040
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8018
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7998
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7978
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7933
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7908
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7838
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7837
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7797
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7746
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7726
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7725
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7696
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7658
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7622
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7612
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7577
Protease Q5RTL1 Q5RTL1_9HIV1 Human immunodeficiency virus 1 4 0.7564
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7534
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7532
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7518
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7514
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7495
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7476
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7476
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7447
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.7408
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7377
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7371
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7359
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7351
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7347
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7344
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7328
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7316
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7273
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7258
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7257
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7257
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7257
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7234
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7232
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7226
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7203
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7192
Chromosome partitioning protein ParA B0ZE06 B0ZE06_ECOLX Escherichia coli 3 0.7187
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7179
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7170
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7169
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7156
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7153
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7141
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7133
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.7132
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7122
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7116
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7114
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7082
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7080
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7077
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7075
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7070
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7061
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7048
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7042
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7039
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7034
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7020
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7019
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7012
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7003
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7002

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