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Luteolin 7-gentiobioside-4'-glucoside

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3cc(O)c4c(c3)oc(cc4=O)c3ccc(c(c3)O)OC3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C33H40O21/c34-7-18-22(39)25(42)28(45)31(52-18)48-9-20-24(41)27(44)29(46)32(54-20)49-11-4-13(37)21-14(38)6-16(50-17(21)5-11)10-1-2-15(12(36)3-10)51-33-30(47)26(43)23(40)19(8-35)53-33/h1-6,18-20,22-37,39-47H,7-9H2/t18-,19-,20-,22-,23-,24-,25+,26+,27+,28-,29-,30-,31-,32-,33?/m1/s1
InChIKey	QULQFSQMGIQIPK-QTEAGBNPSA-N
Formula	C₃₃H₄₀O₂₁
HBA	21
HBD	13
MW	772.66
Rotatable Bonds	10
TPSA	348.58
LogP	-4.95
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	54
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	772.21
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Launaea resedifolia	Asteraceae	Plantae	43198
2	Launaea nudicaulis	Asteraceae	Plantae	43200
3	Launaea capitata	Asteraceae	Plantae	1423390
4	Launaea cassiniana	Asteraceae	Plantae	43198
5	Launaea spinosa	Asteraceae	Plantae	2948567
6	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]

Pubchem: 162869689

Nmrshiftdb2: 60054152

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccc(cc5)OC6CCCCO6

Level: 4

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(cc3=O)-c4ccc(cc4)OC5CCCCO5

Level: 3

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 772.66 g/mol

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

Level: 2

Mol. Weight: 772.66 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 772.66 g/mol

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

Level: 1

Mol. Weight: 772.66 g/mol

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

Level: 1

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 772.66 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 772.66 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 772.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 772.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 772.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.6
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 6.640
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1726.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.660
Plasma Protein Binding: 55.58
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: 4.740
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -40.640
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.640
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.980
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: -3128837.440
Rat (Acute): 2.540
Rat (Chronic Oral): 5.100
Fathead Minnow: 3957.720
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 344979.270
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1.830
Log(P): -3.13
Log S: -3.78
Log(Vapor Pressure): -11302.67
Melting Point: 264.47
pKa Acid: -46.87
pKa Basic: 8.85

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	0.8504
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8504
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8443
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8443
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8393
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8393
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8390
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8390
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8264
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8264
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8147
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8147
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8117
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8117
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.8102
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.8102
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8029
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8029
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7869
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7869
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7720
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7720
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7703
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7703
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7574
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7574
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7555
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7555
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7494
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7494
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	4	0.7406
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	4	0.7406
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7260
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7260
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7213
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7213
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7194
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7194
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7121
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7121
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7108
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7108
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7107
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7107
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7072
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7072
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7069
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7069
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7017
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7017

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