3-O-[(2,3,4-triacetyl-alpha-L-rhamnopyranosyl)-(1→6)]-beta-D-galactopyranoside - Compound Card

3-O-[(2,3,4-triacetyl-alpha-L-rhamnopyranosyl)-(1→6)]-beta-D-galactopyranoside

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3-O-[(2,3,4-triacetyl-alpha-L-rhamnopyranosyl)-(1→6)]-beta-D-galactopyranoside

Structure
Zoomed Structure
  • Family: Gentianaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles CC(=O)O[C@H]1[C@@H](OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(c(c3)O)O)[C@@H]([C@H]([C@H]2O)O)O)O[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)C
InChI InChI=1S/C33H36O19/c1-11-27(47-12(2)34)30(48-13(3)35)31(49-14(4)36)33(46-11)45-10-21-23(41)25(43)26(44)32(51-21)52-29-24(42)22-19(40)8-16(37)9-20(22)50-28(29)15-5-6-17(38)18(39)7-15/h5-9,11,21,23,25-27,30-33,37-41,43-44H,10H2,1-4H3/t11-,21+,23-,25-,26+,27-,30+,31+,32-,33-/m0/s1
InChIKey YAKTXSHIHZXYIW-SWGKFXEASA-N
Formula C33H36O19
HBA 19
HBD 7
MW 736.63
Rotatable Bonds 9
TPSA 287.64
LogP 0.03
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 52
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 736.19
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurium spicatum Gentianaceae Plantae 172074

Showing of synonyms

  • Allam AE, El-Shanawany MA, et al. (2012). Two new acetylated flavonoid glycosides from Centaurium spicatum L. Journal of Natural Medicines,2012,66,388-393. [View] [PubMed]
Pubchem: 162966685
Nmrshiftdb2: 70066686

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 436.5 g/mol

Structure

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

Level: 2

Mol. Weight: 360.41 g/mol

Structure

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

Level: 2

Mol. Weight: 322.36 g/mol

Structure

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

Level: 1

Mol. Weight: 246.26 g/mol

Structure

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

Level: 1

Mol. Weight: 222.24 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 200.28 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-2.98
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
367.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
72.11
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
13.48
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.28
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.98
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.86
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
-665674.09
Rat (Acute)
2.4
Rat (Chronic Oral)
3.9
Fathead Minnow
851.78
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
66197.19
Hydration Free Energy
-2.92
Log(D) at pH=7.4
0.09
Log(P)
1.37
Log S
-4.58
Log(Vapor Pressure)
-2248.51
Melting Point
201.3
pKa Acid
0.61
pKa Basic
2.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9749
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9749
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9039
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9039
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8979
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8979
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8917
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8917
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8891
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8891
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8840
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8840
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8789
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8789
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8602
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8602
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8500
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8500
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8490
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8490
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8451
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8451
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8447
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8447
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8433
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8433
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8393
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8393
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8292
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8292
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8253
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8253
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8104
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8104
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8097
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8097
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8006
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8006
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7979
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7979
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7976
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7976
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7924
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7924
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7908
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7908
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7901
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7901
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7899
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7899
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7889
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7889
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7865
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7865
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7824
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7824
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7800
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7800
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7773
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7773
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7756
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7756
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7750
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7750
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7742
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7742
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7707
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7707
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7698
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7698
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7668
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7668
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7556
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7556
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7454
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7454
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7431
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7431
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7412
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7412
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7334
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7334
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7328
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7328
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7290
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7290
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7283
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7283
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7272
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7272
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7269
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7269
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7240
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7240
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7234
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7234
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7215
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7215
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7200
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7200
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7196
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7196
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7186
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7186
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7149
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7149
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7134
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7134
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7123
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7123
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7080
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7080
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7066
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7066
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7062
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7062
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7061
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7061
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7018
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7018
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7016
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7016

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