Kaempferol-3-gentiobioside - Compound Card

Kaempferol-3-gentiobioside

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Kaempferol-3-gentiobioside

Structure
Zoomed Structure
  • Family: Plantae - Rosaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(cc3)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-8-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-12(31)5-11(30)6-13(16)40-24(25)9-1-3-10(29)4-2-9/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1
InChIKey BITPRCODIALMOV-DEFKTLOSSA-N
Formula C27H30O16
HBA 16
HBD 10
MW 610.52
Rotatable Bonds 7
TPSA 269.43
LogP -2.42
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 610.15
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Tribulus pentandrus Tribulaceae Plantae 1965241
2 Tribulus terrestris Tribulaceae Plantae 210369
3 Eriobotrya japonica Rosaceae Plantae 32224

Showing of synonyms

  • Saleh NAM, Ahmed AA, et al. (1982). Flavonoid glycosides of Tribulus pentandrus and T. terrestris. Phytochemistry,1982,21(8),1995-2000. [View]
  • (2003). Flavonoids from Eriobotrya japonica (Rosaceae) growing in Tunisia. Biochemical Systematics and Ecology, 2003, 31(1), 99-101. [View]
CPRiL: 449541
Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 610.52 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 610.52 g/mol

Structure

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

Level: 2

Mol. Weight: 610.52 g/mol

Structure

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

Level: 1

Mol. Weight: 610.52 g/mol

Structure

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

Level: 1

Mol. Weight: 610.52 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 610.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.52
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.380
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
10.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.760
Plasma Protein Binding
67.43
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
8.440
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.810
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.900
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.930
Micronucleos
Toxic
NR-AhR
Safe
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
-15326.520
Rat (Acute)
2.340
Rat (Chronic Oral)
4.060
Fathead Minnow
33.590
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
477.410
Hydration Free Energy
-2.930
Log(D) at pH=7.4
-0.650
Log(P)
-0.69
Log S
-4.29
Log(Vapor Pressure)
-15.63
Melting Point
208.88
pKa Acid
3.68
pKa Basic
8.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8932
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8932
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8913
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8913
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8889
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8889
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8873
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8873
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8805
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8805
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8560
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8560
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8551
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8551
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8410
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8410
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8376
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8376
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8340
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8340
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8339
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8339
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8327
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8327
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8273
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8273
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8195
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8195
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8145
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8145
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8140
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8140
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8133
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8133
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8030
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8030
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7988
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7988
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7929
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7929
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7891
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7891
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7749
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7749
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7719
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7719
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7614
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7614
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7586
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7586
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7569
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7569
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7563
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7563
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7511
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7511
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7458
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7458
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7446
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7446
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7417
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7417
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7414
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7414
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7393
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7393
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7366
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7366
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7363
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7363
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7315
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7315
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7275
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7275
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7262
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7262
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7245
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7245
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7232
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7232
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7216
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7216
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7194
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7194
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7182
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7182
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7174
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7174
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7167
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7167
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 4 0.7149
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 4 0.7149
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7100
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7100
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7077
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7077
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7066
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7066
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7050
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7050
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7016
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7016
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7004
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7004

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