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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Gentianaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles CC(=O)O[C@H]1[C@@H](O)[C@@H](CO[C@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)OC(=O)C)O[C@H]([C@@H]1O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O
InChI InChI=1S/C35H38O20/c1-12-28(49-13(2)36)32(51-15(4)38)33(52-16(5)39)35(48-12)47-11-23-25(44)30(50-14(3)37)27(46)34(54-23)55-31-26(45)24-21(43)9-18(40)10-22(24)53-29(31)17-6-7-19(41)20(42)8-17/h6-10,12,23,25,27-28,30,32-35,40-44,46H,11H2,1-5H3/t12-,23+,25-,27+,28-,30-,32+,33+,34-,35-/m0/s1
InChIKey YYJHXDJUYFZIJA-MCGBXFDNSA-N
Formula C35H38O20
HBA 20
HBD 6
MW 778.67
Rotatable Bonds 10
TPSA 293.71
LogP 0.6
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 55
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 778.2
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: 162986211
Nmrshiftdb2: 70066687

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 778.67 g/mol

Structure

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

Level: 2

Mol. Weight: 778.67 g/mol

Structure

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

Level: 2

Mol. Weight: 778.67 g/mol

Structure

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

Level: 1

Mol. Weight: 778.67 g/mol

Structure

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

Level: 1

Mol. Weight: 778.67 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 778.67 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 778.67 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 778.67 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 778.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.43
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
4.58
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1351.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
72.08
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
14.44
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-33.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.72
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2453636.53
Rat (Acute)
2.54
Rat (Chronic Oral)
3.53
Fathead Minnow
3103.48
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
268717.21
Hydration Free Energy
-2.92
Log(D) at pH=7.4
0.53
Log(P)
2.37
Log S
-4.33
Log(Vapor Pressure)
-8851.55
Melting Point
203.02
pKa Acid
-36.63
pKa Basic
-1.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9761
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9761
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8986
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8986
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8946
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8946
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8918
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8918
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8887
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8887
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8821
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8821
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8397
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8397
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8380
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8380
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8268
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8268
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8247
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8247
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8128
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8128
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8125
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8125
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8125
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8125
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8101
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8101
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8012
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8012
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7996
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7996
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7956
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7956
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7859
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7859
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7761
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7761
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7753
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7753
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7728
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7728
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7709
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7709
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7702
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7702
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7690
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7690
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7677
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7677
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7631
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7631
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7555
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7555
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7451
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7451
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7449
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7449
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7376
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7376
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7369
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7369
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7348
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7348
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7333
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7333
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7324
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7324
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7306
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7306
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7286
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7286
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7285
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7285
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7241
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7241
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7182
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7182
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7154
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7154
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7140
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7140
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7137
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7137
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7120
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7120
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7117
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7117
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7075
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7075
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7065
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7065
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7030
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7030
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7018
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7018

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