Rhamnetin-3-O-beta-D-glucopyranoside - Compound Card

Rhamnetin-3-O-beta-D-glucopyranoside

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Rhamnetin-3-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles OCC1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)OC)c2ccc(c(c2)O)O)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C22H22O12/c1-31-9-5-12(26)15-13(6-9)32-20(8-2-3-10(24)11(25)4-8)21(17(15)28)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14?,16-,18?,19+,22+/m1/s1
InChIKey PHEWILLIAJUBQE-OKCRKLNBSA-N
Formula C22H22O12
HBA 12
HBD 7
MW 478.41
Rotatable Bonds 5
TPSA 199.51
LogP -0.24
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 478.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Carissa edulis Apocynaceae Plantae 992661

Showing of synonyms

  • Al-Youssef HM and Hassan WHB. (2014). Chemical constituents of Carissa edulis Vahl. Arabian Journal of Chemistry,2014,in press. [View]
Pubchem: 162888321
Nmrshiftdb2: 70052200

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 478.41 g/mol

Structure

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

Level: 1

Mol. Weight: 478.41 g/mol

Structure

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

Level: 1

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 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
-5.43
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.94
Plasma Protein Binding
70.14
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
11.76
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.3
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
-188.58
Rat (Acute)
2.36
Rat (Chronic Oral)
3.81
Fathead Minnow
4.17
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
608.5
Hydration Free Energy
-3.68
Log(D) at pH=7.4
0.49
Log(P)
0.42
Log S
-4.71
Log(Vapor Pressure)
-11.05
Melting Point
194.05
pKa Acid
5.58
pKa Basic
6.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9795
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9795
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9460
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9460
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9368
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9368
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9046
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9046
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8992
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8992
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8922
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8922
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8728
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8728
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8451
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8451
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8440
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8440
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8400
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8400
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8364
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8364
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8352
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8352
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8342
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8342
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8195
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8195
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8152
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8152
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8086
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8086
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8075
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8075
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8068
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8068
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8048
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8048
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8030
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8030
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8025
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8025
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 4 0.8007
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 4 0.8007
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7942
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7942
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7898
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7898
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7897
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7897
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7857
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7857
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7846
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7846
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7837
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7837
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7835
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7835
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7811
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7811
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7793
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7793
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7760
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7760
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7746
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7746
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7744
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7744
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7725
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7725
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7679
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7679
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7633
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7633
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7602
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7602
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7595
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7595
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7579
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7579
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7571
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7571
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7566
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7566
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7550
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7550
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7471
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7471
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7466
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7466
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7434
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7434
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7411
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7411
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7402
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7402
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7365
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7365
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7353
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7353
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7335
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7335
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7287
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7287
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7262
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7262
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7218
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7218
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7218
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7218
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7217
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7217
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7198
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7198
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7180
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7180
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7170
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7170
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7163
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7163
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7140
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7140
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7125
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7125
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7120
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7120
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7119
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7119
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7115
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7115
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7112
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7112
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7100
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7100
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7096
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7096
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7091
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7091
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7085
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7085
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7066
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7066
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7054
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7054
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7010
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7010
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7007
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7007
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7001
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7001

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