Myricitrin - Compound Card

Myricitrin

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Myricitrin

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)c1cc(O)c(c(c1)O)O
InChI InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3/t6-,14-,17+,18+,21-/m0/s1
InChIKey DCYOADKBABEMIQ-OWMUPTOHSA-N
Formula C21H20O12
HBA 12
HBD 8
MW 464.38
Rotatable Bonds 3
TPSA 210.51
LogP 0.19
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 464.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Helianthemum sessiliflorum Cistaceae Plantae 2650562
2 Nymphaea lotus Nymphaeaceae Plantae 264924
3 Epilobium hirsutum Onagraceae Plantae 210355
4 Argania spinosa Sapotaceae Plantae 2945705
5 Tetraclinis articulata Cupressaceae Plantae 13717
6 Lannea alata Anacardiaceae Plantae 289715
7 Halimium halimifolium Cistaceae Plantae 632747
8 Euphorbia gaditana Euphorbiaceae Plantae 3990
9 Eugenia jambolana Myrtaceae Plantae 260142
10 Syzygium grande Myrtaceae Plantae 1042139
11 Syzygium samarangense Myrtaceae Plantae 260143

Showing of synonyms

  • Mahmoud I.I, Marzouk M.S, et al. (2001). Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry, 2001, 58(8), 1239-44. [View] [PubMed]
  • Okoth DA, Chenia HY, et al. (2013). Antibacterial and antioxidant activities of flavonoids from Lannea alata (Engl.) Engl. (Anacardiaceae). Phytochemistry Letters,2013,6(3),476-481. [View]
  • Badaoui M, Magid A, et al. (2020). Antioxidant activity-guided isolation of constituents from Euphorbia gaditana Coss. and their antioxidant and tyrosinase inhibitory activities. Phytochemistry Letters, 2020, 39, 99-104. [View]
  • Klika KD, Khallouki F, et al. (2015). Carboxy methyl and carboxy analogs argaminolics B and C. Records of Natural Products,2015,9(4),597-602. [View]
  • Kerbab K, Sansone F, et al. (2019). Halimium halimifolium: From the Chemical and Functional Characterization to a Nutraceutical Ingredient Design. Planta medica, 2019, 85(11-12), 1024-1033. [View] [PubMed]
  • Benabdelaziz I, Haba H, et al. (2015). Lignans and other constituents from Helianthemum sessiliflorum Pers.. Records of Natural Products,2015,9(3),342-348. [View]
  • Samy M.N, Sugimoto S, et al. (2014). One new flavonoid xyloside and one new natural triterpene rhamnoside from the leaves of Syzygium grande. Phytochemistry Letters, 2014, 10, 86-90. [View]
  • Zidane A, Tits M, et al. (2014). Phytochemical analysis of Tetraclinis articula in relation to its vasorelaxant property. Journal of Materials and Environmental Sciences,2014,5(5),1368-1375. [View]
  • Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]
  • Samy M.N, Sugimoto S, et al. (2014). Taxiphyllin 6-O-Gallate, Actinidioionoside 6-O-Gallate and Myricetrin 2-O-Sulfate from the Leaves of Syzygium samarangense and Their Biological Activities. Chemical & pharmaceutical bulletin,2014, 62(10), 1013-8. [View] [PubMed]
  • Elegami AA, Bates C, et al. (2003). Two very unusual macrocyclic flavonoids from the water lily Nymphaea lotus. Phytochemistry,2003,63(6),727-731. [View] [PubMed]
CPRiL: 50969
Structure

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

Level: 2

Mol. Weight: 464.38 g/mol

Structure

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

Level: 1

Mol. Weight: 464.38 g/mol

Structure

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

Level: 1

Mol. Weight: 464.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 464.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 464.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 464.38 g/mol

Anti-inflammatory
Antiallodynic
Antibacterial
Antinociceptive
Antioxidant
Antioxidative
Radical scavenging

Absorption

Caco-2 (logPapp)
-6.62
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.79
Plasma Protein Binding
80.57
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
14.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.42
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.05
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
-91.38
Rat (Acute)
2.35
Rat (Chronic Oral)
4.17
Fathead Minnow
3.49
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
668.83
Hydration Free Energy
-5.23
Log(D) at pH=7.4
-0.15
Log(P)
0.97
Log S
-4.0
Log(Vapor Pressure)
-11.87
Melting Point
203.02
pKa Acid
4.22
pKa Basic
8.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9180
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9180
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8915
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8915
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8809
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8809
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8777
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8777
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8410
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8410
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8311
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8311
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8255
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8255
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8234
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8234
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8209
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8209
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8190
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8190
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8050
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8050
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7958
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7958
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7928
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7928
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7918
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7918
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7843
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7843
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7837
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7837
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7747
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7747
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7699
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7699
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7689
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7689
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7677
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7677
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7656
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7656
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7649
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7649
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7640
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7640
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7637
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7637
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.7624
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.7624
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7622
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7622
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7618
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7618
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7613
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7613
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7605
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7605
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7578
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7578
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7573
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7573
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7512
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7512
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7502
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7502
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7451
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7451
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 5 0.7269
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 5 0.7269
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7257
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7257
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7215
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7215
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7181
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7181
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7153
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7153
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7150
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7150
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7122
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7122
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7104
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7104
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7087
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7087
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7074
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7074
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7061
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7061
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7056
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7056
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7036
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7036

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