Kaempferol 3-O-galactoside - Compound Card

Kaempferol 3-O-galactoside

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Kaempferol 3-O-galactoside

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17+,18-,21+/m1/s1
InChIKey JPUKWEQWGBDDQB-DTGCRPNFSA-N
Formula C21H20O11
HBA 11
HBD 7
MW 448.38
Rotatable Bonds 4
TPSA 190.28
LogP -0.24
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 448.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Borago officinalis Boraginaceae Plantae 13363
2 Ficus vallis-choudae Moraceae Plantae 182131
3 Ficus barteri Moraceae Plantae 1191361

Showing of synonyms

  • Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]
  • Samy M.N, Hamed A.N, et al. (2016). Officinalioside, a new lignan glucoside from Borago officinalis L. Natural product research, 2016, 30(8), 967-72. [View] [PubMed]
Pubchem: 5282149
Kegg Ligand: C12626
Chebi: 31742
Nmrshiftdb2: 60022409
Metabolights: MTBLC31742
CPRiL: 170629
Structure

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

Level: 2

Mol. Weight: 448.38 g/mol

Structure

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

Level: 1

Mol. Weight: 448.38 g/mol

Structure

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

Level: 1

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.33
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.540
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
82.21
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.960
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.590
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-74.230
Rat (Acute)
2.420
Rat (Chronic Oral)
3.730
Fathead Minnow
3.920
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
605.730
Hydration Free Energy
-5.350
Log(D) at pH=7.4
0.390
Log(P)
0.96
Log S
-4.2
Log(Vapor Pressure)
-11.52
Melting Point
207.84
pKa Acid
5.74
pKa Basic
7.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9374
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9374
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9171
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9171
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9036
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9036
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8986
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8986
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8876
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8876
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8854
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8854
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8810
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8810
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8708
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8708
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8704
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8704
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8517
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8517
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8425
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8425
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8387
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8387
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8341
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8341
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8328
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8328
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8312
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8312
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8256
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8256
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8250
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8250
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8140
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8140
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8098
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8098
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8064
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8064
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8046
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8046
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8034
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8034
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8016
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8016
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8004
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8004
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7998
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7998
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7983
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7983
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7939
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7939
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7930
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7930
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7875
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7875
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7872
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7872
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7820
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7820
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7785
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7785
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7778
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7778
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7769
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7769
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7768
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7768
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7705
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7705
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7667
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7667
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 4 0.7658
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 4 0.7658
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7608
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7608
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7600
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7600
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 5 0.7538
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 5 0.7538
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7527
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7527
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7514
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7514
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7496
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7496
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7484
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7484
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7472
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7472
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7427
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7427
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7407
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7407
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7372
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7372
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7369
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7369
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7369
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7369
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7337
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7337
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7331
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7331
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7310
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7310
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7306
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7306
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7298
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7298
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7261
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7261
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7257
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7257
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7254
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7254
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7229
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7229
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7207
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7207
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7183
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7183
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7145
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7145
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7106
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7106
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7102
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7102
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7072
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7072
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7069
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7069
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7068
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7068
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7056
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7056
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7042
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7042
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7038
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7038
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7004
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7004

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