Isoorientin 7-O-rhamnoside - Compound Card

Isoorientin 7-O-rhamnoside

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Isoorientin 7-O-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Poaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OC[C@H]1OC([C@@H]([C@H]([C@@H]1O)O)O)c1c(O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O
InChI InChI=1S/C27H30O15/c1-8-19(32)22(35)25(38)27(39-8)42-15-6-14-17(12(31)5-13(40-14)9-2-3-10(29)11(30)4-9)21(34)18(15)26-24(37)23(36)20(33)16(7-28)41-26/h2-6,8,16,19-20,22-30,32-38H,7H2,1H3/t8-,16+,19-,20+,22+,23-,24+,25+,26?,27-/m0/s1
InChIKey BWFNSKPHIOFUMZ-WHGHPVCESA-N
Formula C27H30O15
HBA 15
HBD 10
MW 594.52
Rotatable Bonds 5
TPSA 260.2
LogP -1.7
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 594.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Hyparrhenia hirta Poaceae Plantae 42079

Showing of synonyms

  • Bouaziz M, Simmonds MS, et al. (2001). Flavonoids from Hyparrhenia hirta Stapf (Poaceae) growing in Tunisia. Biochemical Systematics and Ecology,2001,29(8),849-851. [View] [PubMed]
Pubchem: 162834054

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(c(c3)C4CCCCO4)OC5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(c(c2)C3CCCCO3)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

Structure

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

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.62
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.610
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
7.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.770
Plasma Protein Binding
67.94
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
11.270
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.780
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.950
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
-8676.370
Rat (Acute)
2.420
Rat (Chronic Oral)
4.670
Fathead Minnow
17.640
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
598.000
Hydration Free Energy
-3.160
Log(D) at pH=7.4
-0.960
Log(P)
-0.51
Log S
-4.19
Log(Vapor Pressure)
-13.28
Melting Point
221.8
pKa Acid
2.38
pKa Basic
9.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9621
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9621
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9392
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9392
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9192
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9192
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9050
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9050
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8878
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8878
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8733
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8733
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8648
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8648
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8645
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8645
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8584
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8584
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8430
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8430
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8364
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8364
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8345
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8345
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8309
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8309
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8174
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8174
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8170
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8170
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8030
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8030
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8007
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8007
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7991
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7991
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7897
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7897
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7835
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7835
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7741
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7741
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7711
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7711
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7694
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7694
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7692
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7692
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7654
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7654
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7605
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7605
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7583
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7583
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7577
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7577
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7506
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7506
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7469
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7469
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7459
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7459
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7439
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7439
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7438
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7438
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7424
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7424
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7387
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7387
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7387
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7387
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7384
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7384
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7344
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7344
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7295
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7295
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7268
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7268
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7252
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7252
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7186
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7186
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7173
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7173
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7168
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7168
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7161
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7161
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7140
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7140
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7135
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7135
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7129
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7129
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7127
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7127
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7120
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7120
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7118
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7118
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7110
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7110
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7058
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7058
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7055
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7055
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7055
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7055
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7044
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7044
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7021
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7021
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7019
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7019
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7019
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7019
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7015
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7015
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7010
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7010
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7004
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7004

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