Orientin - Compound Card

Orientin

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Orientin

Structure
Zoomed Structure
  • Family: Plantae - Arecaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles OCC1O[C@@H]([C@H](C([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-QIBCFILWSA-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 Livistona australis Arecaceae Plantae 115491

Showing of synonyms

  • Kassem MES, Shoela S, et al. (2012). A sulphated flavone glycoside from Livistona australis and its antioxidant and cytotoxic activity. Natural Product Research,2012,26(15),1381-1387. [View] [PubMed]
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)
-6.48
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-6.03
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.72
Plasma Protein Binding
73.4
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
13.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.84
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.61
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
-67.9
Rat (Acute)
2.44
Rat (Chronic Oral)
4.35
Fathead Minnow
3.69
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
661.86
Hydration Free Energy
-5.86
Log(D) at pH=7.4
-0.2
Log(P)
0.85
Log S
-3.66
Log(Vapor Pressure)
-13.04
Melting Point
230.81
pKa Acid
4.1
pKa Basic
9.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9138
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9138
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8966
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8966
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8894
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8894
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8881
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8881
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8823
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8823
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8517
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8517
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8463
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8463
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8455
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8455
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8412
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8412
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8368
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8368
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8330
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8330
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8326
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8326
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8300
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8300
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8265
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8265
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8215
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8215
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7943
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7943
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7943
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7943
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7909
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7909
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7883
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7883
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7883
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7883
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7871
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7871
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7864
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7864
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7820
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7820
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 4 0.7803
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 4 0.7803
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7801
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7801
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7746
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7746
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7717
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7717
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7713
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7713
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7687
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7687
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7685
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7685
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7680
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7680
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7611
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7611
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7606
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7606
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7587
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7587
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7500
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7500
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7491
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7491
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7473
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7473
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7451
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7451
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7425
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7425
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7409
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7409
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7363
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7363
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7347
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7347
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7346
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7346
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7335
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7335
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7291
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7291
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7270
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7270
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7264
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7264
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7243
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7243
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7243
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7243
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7240
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7240
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7231
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7231
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7195
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7195
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7166
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7166
Alpha-2,3/2,6-sialyltransferase/sialidase Q15KI8 Q15KI8_PASMD Pasteurella multocida 4 0.7116
Alpha-2,3/2,6-sialyltransferase/sialidase Q15KI8 Q15KI8_PASMD Pasteurella multocida 4 0.7116
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7080
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7080
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7033
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7033
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7026
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7026
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7024
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7024
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7019
Casein kinase II subunit alpha P68400 CSK21_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
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7012
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7012
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7007
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7007
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7002
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7002

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