Luteolin 6-c-beta-d-glucopyranoside, 8-c-alpha-l-arabinopyranoside - Compound Card

Luteolin 6-c-beta-d-glucopyranoside, 8-c-alpha-l-arabinopyranoside

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Luteolin 6-c-beta-d-glucopyranoside, 8-c-alpha-l-arabinopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2c(O)c(O[C@@H]3OC[C@@H]([C@@H]([C@H]3O)O)O)c3c(c2O)c(=O)cc(o3)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C26H28O17/c27-5-13-16(33)18(35)20(37)26(41-13)42-23-17(34)14-10(30)4-12(7-1-2-8(28)9(29)3-7)40-22(14)24(21(23)38)43-25-19(36)15(32)11(31)6-39-25/h1-4,11,13,15-16,18-20,25-29,31-38H,5-6H2/t11-,13+,15-,16+,18-,19+,20+,25-,26-/m0/s1
InChIKey KHLMVFJKNYZTSV-AJHWVGOQSA-N
Formula C26H28O17
HBA 17
HBD 11
MW 612.49
Rotatable Bonds 6
TPSA 289.66
LogP -2.72
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 612.13
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Premna odorata Lamiaceae Plantae 1037421

Showing of synonyms

  • Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]
Pubchem: 102210457

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(OC4CCCCO4)cc(c3)OC5CCCCO5

Level: 3

Mol. Weight: 612.49 g/mol

Structure

SMILES: O1CCCCC1Oc(c(c23)occc2=O)cc(c3)OC4CCCCO4

Level: 2

Mol. Weight: 612.49 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)OC4CCCCO4

Level: 2

Mol. Weight: 612.49 g/mol

Structure

SMILES: O1CCCCC1Oc(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 612.49 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)OC3CCCCO3

Level: 1

Mol. Weight: 612.49 g/mol

Structure

SMILES: O=c1ccoc(c12)c(ccc2)OC3CCCCO3

Level: 1

Mol. Weight: 612.49 g/mol

Structure

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

Level: 1

Mol. Weight: 612.49 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 612.49 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 612.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 612.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.850
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
10.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.590
Plasma Protein Binding
63.65
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
11.230
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.860
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
6.150
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
-14432.620
Rat (Acute)
2.240
Rat (Chronic Oral)
4.920
Fathead Minnow
29.890
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
517.860
Hydration Free Energy
-3.070
Log(D) at pH=7.4
-1.800
Log(P)
-1.43
Log S
-3.8
Log(Vapor Pressure)
-15.1
Melting Point
222.97
pKa Acid
1.86
pKa Basic
9.4
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 0.9161
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8778
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8303
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8225
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8212
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.8161
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8132
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8016
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7949
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7750
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7601
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7600
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7399
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7355
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7287
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7226
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7220
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7212
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7166
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7090
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7077
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7038
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7031
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7002

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