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Cyanidin-3-O-glucoside
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Anthocyanin Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2ccc(c(c2)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16-,17-,18+,19-,21-/m1/s1 |
| InChIKey | RKWHWFONKJEUEF-GQUPQBGVSA-O |
| Formula | C21H21O11+ |
| HBA | 10 |
| HBD | 8 |
| MW | 449.39 |
| Rotatable Bonds | 4 |
| TPSA | 191.6 |
| LogP | 0.38 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 32 |
| Formal Charge | 1 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 449.11 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Crataegus monogyna | Rosaceae | Plantae | 140997 |
Showing of synonyms
Cyanidin-3-O-glucoside
Cyanidin 3-glucoside
KUROMANIN
Chrysanthemin cation
UNII-Q6NK5V5B5O
Q6NK5V5B5O
Cyanidin 3-beta-glucoside cation
CHEBI:28426
Chrysanthemin
Cyanidin 3-O-beta-D-glucoside
(2S,3R,4S,5S,6R)-2-(2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
47705-70-4
7084-24-4
1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-
(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Kuromamine
Asterin?
C08604
SCHEMBL409593
CHEMBL257839
CYANIDIN 3-GLUCOSIDE CATION
CYANIDIN 3-GLUCOSIDE CATION [WHO-DD]
BRD-K51337109-003-01-3
Q63399306
2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl beta-D-glucopyranoside
1-BENZOPYRYLIUM, 2-(3,4-DIHYDROXYPHENYL)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-
InChI=1/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16-,17-,18+,19-,21-/m1/s
- Mraihi F, Hidalgo M, et al. (2015). Wild grown red and yellow hawthorn fruits from Tunisia as source of antioxidants. Arabian Journal of Chemistry, 2015, 8(4), 570-578. [View]
Pubchem:
441667
Cas:
47705-70-4
Gnps:
CCMSLIB00000210356
Zinc:
ZINC000004097706
Kegg Ligand:
C08604
Chebi:
28426
Nmrshiftdb2:
20051775
Metabolights:
MTBLC28426
Chembl:
CHEMBL257839
CPRiL:
61842
SMILES: c1cccc(c12)[o+]c(-c3ccccc3)c(c2)OC4CCCCO4
Level: 2
Mol. Weight: 449.39 g/mol
SMILES: c1cccc(c12)[o+]cc(c2)OC3CCCCO3
Level: 1
Mol. Weight: 449.39 g/mol
SMILES: c1cccc(c12)[o+]c(cc2)-c3ccccc3
Level: 1
Mol. Weight: 449.39 g/mol
SMILES: c1cc[o+]c(c12)cccc2
Level: 0
Mol. Weight: 449.39 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 449.39 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 449.39 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.7
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.680
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 0.4
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.910
- Plasma Protein Binding
- 81.28
- 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
- 13.830
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.200
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.160
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.510
- 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
- -72.790
- Rat (Acute)
- 2.310
- Rat (Chronic Oral)
- 3.840
- Fathead Minnow
- 3.700
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 626.820
- Hydration Free Energy
- -5.390
- Log(D) at pH=7.4
- 0.320
- Log(P)
- -2.05
- Log S
- -2.9
- Log(Vapor Pressure)
- -12.53
- Melting Point
- 213.81
- pKa Acid
- 4.63
- pKa Basic
- 7.72
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9332 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9307 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 4 | 0.9034 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8902 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8882 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8809 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.8802 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8795 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8786 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8731 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8647 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8633 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8628 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8618 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8599 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8592 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8581 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.8577 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8572 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8487 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.8483 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8473 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8456 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8449 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8354 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8338 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.8251 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8213 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8193 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8170 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.8135 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8127 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8066 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8058 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.8052 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8042 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8000 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7954 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 4 | 0.7834 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7832 |
| Beta-glucuronidase | P05804 | BGLR_ECOLI | Escherichia coli | 3 | 0.7787 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7785 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7745 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7745 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7737 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7709 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7632 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7631 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7588 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7582 |
| Cyclic dipeptide N-prenyltransferase | D1D8L6 | D1D8L6_ASPFM | Neosartorya fumigata | 3 | 0.7522 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7504 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7502 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7460 |
| Secoisolariciresinol dehydrogenase | Q94KL8 | SILD_PODPE | Podophyllum peltatum | 4 | 0.7458 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7427 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7418 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7379 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7321 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7227 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7226 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7226 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7225 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7212 |
| GTPase KRas | P01116 | RASK_HUMAN | Homo sapiens | 5 | 0.7206 |
| Beta-hexosaminidase | Q9KU37 | NAGZ_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7188 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.7168 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7162 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7146 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7138 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 3 | 0.7114 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7098 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7066 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7055 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7051 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7049 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7048 |
| GTPase KRas | P01116 | RASK_HUMAN | Homo sapiens | 5 | 0.7047 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7046 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7033 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7032 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7027 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7009 |