Orientin - Compound Card

Orientin

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Orientin

Structure
Zoomed Structure
  • Family: Leguminosae, Poaceae, Euphorbiaceae, Iridaceae, Moraceae, Asteraceae-Compositae, Onagraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside, Flavonoid Glycoside
Canonical Smiles OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)cc(c2c1oc(cc2=O)c1ccc(c(c1)O)O)O
InChI InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1
InChIKey PLAPMLGJVGLZOV-VPRICQMDSA-N
Formula C21H20O11
HBA 11
HBD 8
MW 448.38
Rotatable Bonds 3
TPSA 201.28
LogP -0.2
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 448.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Croton zambezicus Euphorbiaceae Plantae 323089
2 Moraea sisyrinchium Iridaceae Plantae 148530
3 Hyparrhenia hirta Poaceae Plantae 42079
4 Psiadia punctulata Asteraceae-Compositae Plantae 72969
5 Ficus asperifolia Moraceae Plantae 182103
6 Ficus variifolia Moraceae Plantae 425835
7 Ficus sansibarica Moraceae Plantae 309319
8 Ficus thonningii Moraceae Plantae 309310
9 Ludwigia leptocarpa Onagraceae Plantae 1401410
10 Adenocarpus anagyrifolius Leguminosae Plantae
11 Adenocarpus anagyrifolius var. leiocarpa Leguminosae Plantae
12 Adenocarpus artemisifolius Leguminosae Plantae
13 Adenocarpus bacquei Leguminosae Plantae
14 Adenocarpus cincinnatus Leguminosae Plantae
15 Adenocarpus decorticans Leguminosae Plantae
16 Adenocarpus telonensis Leguminosae Plantae
17 Parkinsonin aculeata Leguminosae Plantae

Showing of synonyms

  • Mabou FD, Tamokou JD, et al. (2016). Complex secondary metabolites from Ludwigia leptocarpa with potent antibacterial and antioxidant activities.. Drug discoveries & therapeutics,2016, 10(3), 141-149. [View] [PubMed]
  • Wagner H, Horhammer L, et al. (1970). Flavone-C-glykoside in Croton zambezicus. Phytochemistry,1970,9,897-897. [View]
  • Rafaa S. Essokne, Renée J. Grayer, et al. (2012). Flavonoids as chemosystematic markers for the genus Adenocarpus. Biochemical Systematics and Ecology,2012,42,49–58. [View]
  • 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]
  • El-Shabrawy MOA Marzouk MM, Kawashty SA, et al. (2013). Flavonoids from Moraea sisyrinchium (L.) Ker Gawl. (Iridaceae) in Egypt. International Conference on Applied Life Sciences (ICALS2013),2013,UAE. September 15-17, 2013. [View]
  • Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]
  • Nabil H. El-Sayed, Ahmed A. Ahmed, et al. (1991). Luteolin 7,4'-dimethyl ether 6-C-glucoside from Parkinsonia aculeata. Phytochemistry,1991,30(7),2442. [View]
  • Abou-Zaid MM, El-Karemy Z, et al. (1991). The flavonoids of Psiadia punctulata. Bulletin of the Chemical Society of Ethiopia,1991,5(1),37-40. [View]
Pubchem: 5281675
Kegg Ligand: C10114
Chebi: 7781
Nmrshiftdb2: 60019472
Metabolights: MTBLC7781
Pdb Ligand: USE
Bindingdb: 84982
CPRiL: 54728
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Structure

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

Level: 1

Mol. Weight: 222.24 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 306.36 g/mol

Structure

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 230.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.46
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-6.030
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.720
Plasma Protein Binding
81.44
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
13.650
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.410
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.840
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.620
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
-68.680
Rat (Acute)
2.450
Rat (Chronic Oral)
4.340
Fathead Minnow
3.670
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
664.280
Hydration Free Energy
-5.850
Log(D) at pH=7.4
-0.160
Log(P)
0.81
Log S
-3.7
Log(Vapor Pressure)
-13.34
Melting Point
231.86
pKa Acid
4.13
pKa Basic
9.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8842
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8842
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8752
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8752
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8631
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8631
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8621
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8621
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8502
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8502
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8432
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8432
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8305
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8305
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8265
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8265
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8263
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8263
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8263
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8263
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8244
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8244
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8207
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8207
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8200
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8200
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8145
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8145
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.8140
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.8140
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8085
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8085
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8046
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8046
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8012
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8012
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7856
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7856
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7856
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7856
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7782
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7782
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7775
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7775
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7660
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7660
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7529
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7529
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7475
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7475
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7472
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7472
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 4 0.7466
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 4 0.7466
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7447
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7447
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7431
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7431
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7385
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7385
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7321
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7321
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7317
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7317
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7267
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7267
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7219
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7219
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7201
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7201
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7196
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7196
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7167
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7167
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7157
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7157
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7116
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7116
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7107
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7107
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7068
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7068
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7062
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7062
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7014
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7014
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7012
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7012

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