Isorhamnetin-3-O-rutinoside - Compound Card

Isorhamnetin-3-O-rutinoside

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Isorhamnetin-3-O-rutinoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1OC(CO[C@@H]2OC(C)[C@@H]([C@H](C2O)O)O)[C@H]([C@H](C1O)O)O)O
InChI InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9?,16?,18-,19+,21+,22+,23?,24?,27+,28-/m0/s1
InChIKey UIDGLYUNOUKLBM-ZJNQJRHWSA-N
Formula C28H32O16
HBA 16
HBD 9
MW 624.55
Rotatable Bonds 7
TPSA 258.43
LogP -1.38
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 624.17
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Opuntia dillenii Cactaceae Plantae 308223
2 Pituranthos scoparius Apiaceae Plantae 489362
3 Calendula officinalis Asteraceae Plantae 41496

Showing of synonyms

  • Ukiya M, Akihisa T, et al. (2006). Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of Marigold (Calendula officinalis) flowers. Journal of Natural Products,2006,69,1692-1696. [View] [PubMed]
  • Ahmed MS, El Tanbouly ND, et al. (2005). Antiinflammatory flavonoids from Opuntia dillenii (Ker-Gawl) Haw. flowers growing in Egypt.. Phytotherapy Research,2005,19(9),807-809. [View] [PubMed]
  • Dahia M, Siracusa L, et al. (2009). Constituents of the polar extracts from Algerian Pituranthos scoparius. Natural Product Communications,2009,4(12),1691-1692. [View] [PubMed]
Pubchem: 45933931

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 624.55 g/mol

Structure

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

Level: 2

Mol. Weight: 624.55 g/mol

Structure

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

Level: 2

Mol. Weight: 624.55 g/mol

Structure

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

Level: 1

Mol. Weight: 624.55 g/mol

Structure

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

Level: 1

Mol. Weight: 624.55 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 624.55 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 624.55 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 624.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 624.55 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-6.59
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.200
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
13.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
47.45
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
12.390
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.980
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.900
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.660
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
-22490.860
Rat (Acute)
2.260
Rat (Chronic Oral)
4.430
Fathead Minnow
45.580
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
360.740
Hydration Free Energy
-2.930
Log(D) at pH=7.4
-0.210
Log(P)
-0.11
Log S
-4.88
Log(Vapor Pressure)
-16.73
Melting Point
215.07
pKa Acid
4.23
pKa Basic
5.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9168
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9168
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8845
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8845
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8705
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8705
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8692
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8692
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8655
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8655
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8546
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8546
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8296
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8296
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8288
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8288
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8199
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8199
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8158
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8158
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8143
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8143
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.8105
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.8105
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8036
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8036
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7986
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7986
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7920
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7920
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7873
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7873
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7814
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7814
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7804
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7804
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7768
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7768
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7759
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7759
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7720
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7720
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7674
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7674
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 4 0.7634
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 4 0.7634
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7572
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7572
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7515
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7515
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7414
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7414
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7348
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7348
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7335
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7335
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7278
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7278
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7247
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7247
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7235
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7235
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7233
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7233
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7176
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7176
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7168
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7168
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7157
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7157
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7141
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7141
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7123
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7123
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7116
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7116
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7111
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7111
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7095
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7095
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7048
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7048
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7018
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7018

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