Orientin - Compound Card

Orientin

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Orientin

Structure
Zoomed Structure
  • Family: Plantae - Onagraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: 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 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

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

Level: 2

Mol. Weight: 448.38 g/mol

Structure

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

Level: 1

Mol. Weight: 448.38 g/mol

Structure

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

Level: 1

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 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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