Isorhamnetin 3-O-rutinoside - Compound Card

Isorhamnetin 3-O-rutinoside

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Isorhamnetin 3-O-rutinoside

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • 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-/m0/s1
InChIKey UIDGLYUNOUKLBM-GEBJFKNCSA-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 Gomphocarpus sinaicus Apocynaceae Plantae 2291033
2 Atractylis flava Asteraceae Plantae 41483
3 Nitraria retusa Nitrariaceae Plantae 43875
4 Galium brunneum Rubiaceae Plantae 25168

Showing of synonyms

  • Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]
  • Chabani S, Haba H, et al. (2013). Flavonoid glycosides and triterpenoids from Atractylis flava.. Phytochemistry Letters,2013,6,9-13. [View]
  • Heneidak S, Grayer RJ, et al. (2006). Flavonoid glycosides from Egyptian species of the tribe Asclepiadeae (Apocynaceae, subfamily Asclepiadoideae). Biochemical Systematics and Ecology,2006,34(7),575-584. [View]
  • Halim AF, Saad HE, et al. (1995). Flavonol glycosides from Nitraria retusa. Phytochemistry,1995,40(1),349-351. [View] [PubMed]
Pubchem: 45933931
CPRiL: 243898
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)
-6.63
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
68.13
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
12.400
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
5.670
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
-22491.810
Rat (Acute)
2.270
Rat (Chronic Oral)
4.410
Fathead Minnow
45.710
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
362.710
Hydration Free Energy
-2.930
Log(D) at pH=7.4
-0.230
Log(P)
-0.11
Log S
-4.94
Log(Vapor Pressure)
-16.99
Melting Point
212.44
pKa Acid
4.2
pKa Basic
5.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9318
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9318
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9143
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9143
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8858
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8858
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8673
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8673
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8496
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8496
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8492
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8492
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8469
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8469
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8402
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8402
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8393
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8393
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8205
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8205
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8144
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8144
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8130
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8130
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7981
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7981
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7962
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7962
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7945
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7945
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7939
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7939
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7904
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7904
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7868
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7868
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7856
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7856
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7803
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7803
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7754
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7754
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7731
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7731
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7649
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7649
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7601
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7601
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7559
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7559
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7530
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7530
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7490
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7490
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7471
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7471
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7427
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7427
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7410
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7410
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7382
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7382
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7339
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7339
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7301
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7301
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7239
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7239
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7170
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7170
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7164
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7164
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7153
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7153
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7151
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7151
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7132
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7132
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7130
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7130
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7116
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7116
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7098
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7098
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7095
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7095
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7082
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7082
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7055
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7055
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7053
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7053
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7002
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7002

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