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Luteolin-7-O-beta-D-glucopyranoside

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Stachydrine Alkaloid

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)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C27H30O16/c28-7-17-20(33)22(35)24(37)26(42-17)39-8-18-21(34)23(36)25(38)27(43-18)40-10-4-13(31)19-14(32)6-15(41-16(19)5-10)9-1-2-11(29)12(30)3-9/h1-6,17-18,20-31,33-38H,7-8H2/t17-,18-,20-,21-,22+,23+,24-,25-,26-,27-/m1/s1
InChIKey	LDTDRTSKWGQBAA-IPOZFMEPSA-N
Formula	C₂₇H₃₀O₁₆
HBA	16
HBD	10
MW	610.52
Rotatable Bonds	7
TPSA	269.43
LogP	-2.42
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	Moluccella laevis	Lamiaceae	Plantae	483851

Showing of synonyms

Hamed A.N.E, Abdelaty N.A, et al. (2022). Antiproliferative potential of Moluccella laevis L. aerial parts family Lamiaceae (Labiatae), supported by phytochemical investigation and molecular docking study. Natural product research, 2022, 36(5), 1391-1395. [View] [PubMed]

Pubchem: 14032967

Cas: 70855-41-3

Zinc: ZINC000095913375

Nmrshiftdb2: 60073370

CPRiL: 20200

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

Level: 3

Mol. Weight: 610.52 g/mol

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

Level: 2

Mol. Weight: 610.52 g/mol

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

Level: 2

Mol. Weight: 610.52 g/mol

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

Level: 1

Mol. Weight: 610.52 g/mol

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

Level: 1

Mol. Weight: 610.52 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 610.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 610.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.400
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 10.03

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.750
Plasma Protein Binding: 69.09
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: 10.370
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.220
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.740
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.310
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: -15052.790
Rat (Acute): 2.310
Rat (Chronic Oral): 4.390
Fathead Minnow: 32.860
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: 466.090
Hydration Free Energy: -2.940
Log(D) at pH=7.4: -0.620
Log(P): -1.12
Log S: -4.31
Log(Vapor Pressure): -15.23
Melting Point: 235.02
pKa Acid: 3.58
pKa Basic: 8.28

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9310
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9199
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.9053
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8999
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8993
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8975
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8892
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8887
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8848
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8737
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8706
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8701
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8676
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8656
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8611
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8580
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8549
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8517
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	4	0.8477
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8361
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8337
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8332
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8286
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8277
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8260
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8221
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8210
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8188
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8167
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8167
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.8154
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	4	0.8050
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8008
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8002
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7991
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7974
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7934
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7909
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7909
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7908
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7892
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7888
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7863
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7813
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7813
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7782
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7753
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7751
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7738
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7737
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7719
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7716
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7694
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7683
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7670
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7668
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7654
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7650
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7640
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7638
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7628
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7622
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7621
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7616
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7616
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7609
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7606
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.7593
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7574
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7568
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7547
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7520
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7518
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7512
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7498
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7495
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7421
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7366
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7362
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.7350
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7328
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7306
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7302
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7300
Cytosine-specific methyltransferase	Q8EVR5	Q8EVR5_MYCPE	Mycoplasma penetrans	4	0.7287
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7284
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7283
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7275
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7272
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7262
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7259
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7242
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7230
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7222
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7219
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7216
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7201
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7200
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7191
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7188
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7187
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7174
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7173
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7171
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	3	0.7167
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7157
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7156
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7155
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7145
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7143
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7139
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7138
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7130
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7130
Replicase polyprotein 1ab	P0C6X7	R1AB_CVHSA	Human SARS coronavirus	4	0.7124
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7109
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.7102
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7102
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7101
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7095
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7085
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7075
Methyltransferase domain-containing protein	O57965	O57965_PYRHO	Pyrococcus horikoshii	4	0.7067
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7063
Ribosomal protein S6 kinase alpha-1	Q15418	KS6A1_HUMAN	Homo sapiens	3	0.7060
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7054
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7040
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7035
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7033
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7031
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7024
Ribosomal protein L11 methyltransferase, putative	C3MWA1	C3MWA1_SULIM	Sulfolobus islandicus	4	0.7022
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7020
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7019
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7018
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7016

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