Isorhamnetin-3-rutinoside - Compound Card

Isorhamnetin-3-rutinoside

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Isorhamnetin-3-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]1O[C@H](CO[C@H]2O[C@H](C)[C@H]([C@@H]([C@@H]2O)O)O)[C@H]([C@@H]([C@H]1O)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+/m1/s1
InChIKey UIDGLYUNOUKLBM-OPUWVCDQSA-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 Cleome species Capparaceae Plantae 25782
2 Tribulus terrestris Tribulaceae Plantae 210369
3 Ammi visnaga Apiaceae Plantae 1053409
4 Bupleurum montanum Apiaceae Plantae 198847
5 Senecio gallicus Asteraceae Plantae 121545
6 Senecio hoggariensis Asteraceae Plantae 352207

Showing of synonyms

  • Benahmed M, Akkal S, et al. (2014). Constituents from Bupleurum montanum (Coss. & Dur.) (Apiaceae). Arabian Journal of Chemistry,2014,7,1065-1069. [View]
  • Saleh NAM, Ahmed AA, et al. (1982). Flavonoid glycosides of Tribulus pentandrus and T. terrestris. Phytochemistry,1982,21(8),1995-2000. [View]
  • Sharaf M, El-Ansari MA, et al. (1997). Flavonoids of four Cleome and three Capparis species.. Biochemical Systematics and Ecology,1997,25(2),161-166. [View]
  • Mansour RMA, Saleh NAM (1981). Flavonoids of three local Senecio species. Phytochemistry, 1981,20(5),1180-1181. [View]
  • Bencheraiet R, Kherrab H, et al. (2011). Flavonols and antioxidant activity of Ammi visnaga L. (Apiaceae). Records of Natural Products,2011,5(1),52-55. [View]
Pubchem: 17751019
Nmrshiftdb2: 60049396

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

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.64
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
13.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
68.05
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
12.420
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.220
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
-22491.990
Rat (Acute)
2.270
Rat (Chronic Oral)
4.410
Fathead Minnow
45.730
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
362.240
Hydration Free Energy
-2.930
Log(D) at pH=7.4
-0.220
Log(P)
-0.27
Log S
-4.93
Log(Vapor Pressure)
-16.99
Melting Point
208.93
pKa Acid
4.16
pKa Basic
5.95
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 0.9188
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9188
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8917
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8917
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8800
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8800
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8709
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8709
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8666
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8666
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8575
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8575
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8473
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8473
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8468
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8468
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8449
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8449
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8393
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8393
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8277
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8277
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8253
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8253
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8242
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8242
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8238
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8238
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8113
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8113
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8058
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8058
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7982
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7982
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7971
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7971
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7858
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7858
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7800
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7800
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7770
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7770
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7726
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7726
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7695
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7695
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7693
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7693
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7680
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7680
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7645
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7645
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7634
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7634
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7605
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7605
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7564
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7564
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7512
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7512
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7396
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7396
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7305
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7305
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7285
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7285
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7244
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7244
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7228
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7228
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7193
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7193
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7193
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7193
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7175
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7175
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7166
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7166
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7121
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7121
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7112
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7112
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7110
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7110
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7102
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7102
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7096
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7096
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7056
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7056
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7050
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7050
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7025
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7025
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7022
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7022
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7003
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7003

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