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Luteolin 7-[6′′′-acetylallosyl-(1→2)glucoside]

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

Canonical Smiles	OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)O)C([C@H]([C@@H]1O)O)O[C@@H]1OC(COC(=O)C)[C@H]([C@@H](C1O)O)O
InChI	InChI=1S/C29H32O17/c1-10(31)41-9-20-23(37)24(38)26(40)28(45-20)46-27-25(39)22(36)19(8-30)44-29(27)42-12-5-15(34)21-16(35)7-17(43-18(21)6-12)11-2-3-13(32)14(33)4-11/h2-7,19-20,22-30,32-34,36-40H,8-9H2,1H3/t19?,20?,22-,23-,24+,25+,26?,27?,28+,29-/m1/s1
InChIKey	SDLRUUXTNVUGJL-WJBWUEBSSA-N
Formula	C₂₉H₃₂O₁₇
HBA	17
HBD	9
MW	652.56
Rotatable Bonds	8
TPSA	275.5
LogP	-1.85
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	652.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Stachys aegyptiaca	Lamiaceae	Plantae	1391947

Showing of synonyms

El-Ansari M, Abdalla M, et al. (1991). Flavonoid constituents of Stachys aegyptiaca. Phytochemistry, 1991,30(4),1169-1173. [View]

Pubchem: 44258116

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 652.56 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 652.56 g/mol

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

Level: 2

Mol. Weight: 652.56 g/mol

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

Level: 1

Mol. Weight: 652.56 g/mol

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

Level: 1

Mol. Weight: 652.56 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 652.56 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 652.56 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 652.56 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 652.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.65
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.12
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 32.42

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.8
Plasma Protein Binding: 48.05
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: 10.9
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.41
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.92
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.83
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: -55925.51
Rat (Acute): 2.21
Rat (Chronic Oral): 4.05
Fathead Minnow: 89.0
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: 695.93
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.21
Log(P): -0.33
Log S: -4.94
Log(Vapor Pressure): -51.92
Melting Point: 212.58
pKa Acid: 4.22
pKa Basic: 6.14

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	0.9387
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9048
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8870
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8865
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8835
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8777
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8766
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8761
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8682
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8625
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8559
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8506
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8430
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.8382
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8357
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8356
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8308
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8299
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8268
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.8180
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8179
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8164
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8143
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	5	0.8040
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7999
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7919
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7917
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7854
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7758
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7749
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7738
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7702
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7700
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7699
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7695
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7679
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7678
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7663
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7663
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7633
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7623
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7623
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7602
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7601
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7568
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	4	0.7495
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7494
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7483
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7482
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7474
Cytosine-specific methyltransferase	Q8EVR5	Q8EVR5_MYCPE	Mycoplasma penetrans	4	0.7473
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7452
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7447
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7443
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7427
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7400
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7393
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7359
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7347
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7344
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7309
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7298
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7297
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7285
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7263
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7259
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7243
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7232
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7219
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7215
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7172
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7159
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7153
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7150
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7141
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7129
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7108
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7106
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7101
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7099
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7098
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7095
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7084
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7079
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7075
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7074
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7066
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7066
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7043
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7043
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7042
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7040
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7034
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	3	0.7029
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7023
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7017
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7013
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7010
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7002
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7001
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7001

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