Luteolin 7,3'-diglucoside - Compound Card

Luteolin 7,3'-diglucoside

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Luteolin 7,3'-diglucoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O[C@@H]2OC(CO)[C@H]([C@@H](C2O)O)O)O)C([C@H]([C@@H]1O)O)O
InChI InChI=1S/C27H30O16/c28-7-17-20(33)22(35)24(37)26(42-17)39-10-4-12(31)19-13(32)6-14(40-16(19)5-10)9-1-2-11(30)15(3-9)41-27-25(38)23(36)21(34)18(8-29)43-27/h1-6,17-18,20-31,33-38H,7-8H2/t17?,18?,20-,21-,22+,23+,24?,25?,26-,27-/m1/s1
InChIKey BISZYPSIZGKOFA-QYCDPOAQSA-N
Formula C27H30O16
HBA 16
HBD 10
MW 610.52
Rotatable Bonds 7
TPSA 269.43
LogP -2.77
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 610.15
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia judaica Asteraceae Plantae 205369
2 Launaea resedifolia Asteraceae Plantae 43198
3 Launaea nudicaulis Asteraceae Plantae 43200
4 Launaea capitata Asteraceae Plantae 1423390
5 Launaea cassiniana Asteraceae Plantae 43198
6 Launaea spinosa Asteraceae Plantae 2948567
7 Launaea enuiloba Asteraceae Plantae 43198

Showing of synonyms

  • Mansour RMA, Ahmed AA, et al. (1983). Flavone glycosides of some Launaea species. Phytochemistry,1983,22(11),2630-2631. [View]
  • Saleh NAM, El-Negoumy SI, et al. (1987). Flavonoids of Artemisia judaica, A. monosperma and A. Herba-alba.. Phytochemistry,1987,26(11),3059-3064. [View]
Pubchem: 44258089
Nmrshiftdb2: 60054149

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(cc3=O)-c4cc(ccc4)OC5CCCCO5

Level: 3

Mol. Weight: 610.52 g/mol

Structure

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

Level: 2

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3cc(ccc3)OC4CCCCO4

Level: 2

Mol. Weight: 610.52 g/mol

Structure

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

Level: 1

Mol. Weight: 610.52 g/mol

Structure

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

Level: 1

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 610.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.52 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
-5.46
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
10.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.76
Plasma Protein Binding
55.04
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
7.62
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.99
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.75
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.19
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
-15600.5
Rat (Acute)
2.38
Rat (Chronic Oral)
4.81
Fathead Minnow
33.62
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
468.86
Hydration Free Energy
-2.98
Log(D) at pH=7.4
-0.84
Log(P)
-1.6
Log S
-3.96
Log(Vapor Pressure)
-16.14
Melting Point
260.56
pKa Acid
3.11
pKa Basic
7.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9111
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9111
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8970
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8970
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8669
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8669
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8042
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8042
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7888
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7888
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7812
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7812
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7769
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7769
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7717
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7717
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7653
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7653
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7518
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7518
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7432
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7432
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7324
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7324
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7193
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7193
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7148
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7148
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7132
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7132
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7094
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7094
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7088
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7088
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7053
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7053
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7029
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7029

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