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Luteolin 3'-O-glucuronide

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

Canonical Smiles	Oc1cc(O)c2c(c1)oc(cc2=O)c1ccc(c(c1)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O)O
InChI	InChI=1S/C21H18O12/c22-8-4-10(24)15-11(25)6-12(31-14(15)5-8)7-1-2-9(23)13(3-7)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
InChIKey	JDOFZOKGCYYUER-ZFORQUDYSA-N
Formula	C₂₁H₁₈O₁₂
HBA	11
HBD	7
MW	462.36
Rotatable Bonds	4
TPSA	207.35
LogP	-0.15
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	462.08
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rosmarinuseriocalyx	Lamiaceae	Plantae	—

Showing of synonyms

Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]

Pubchem: 10253785

Cas: 53527-42-7

Gnps: CCMSLIB00006480789

Zinc: ZINC000034541040

Chebi: 75726

Nmrshiftdb2: 60022917

Metabolights: MTBLC75726

CPRiL: 98101

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

Level: 2

Mol. Weight: 462.36 g/mol

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

Level: 1

Mol. Weight: 462.36 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 462.36 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 462.36 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.87
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.56
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.03
Plasma Protein Binding: 88.11
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: 10.62
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.84
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.1
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.67
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: -100.93
Rat (Acute): 2.23
Rat (Chronic Oral): 4.41
Fathead Minnow: 4.08
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: 631.43
Hydration Free Energy: -4.05
Log(D) at pH=7.4: -1.03
Log(P): 0.78
Log S: -4.68
Log(Vapor Pressure): -13.11
Melting Point: 246.23
pKa Acid: 4.32
pKa Basic: 6.85

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	0.9300
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9140
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.9118
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9077
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8975
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8962
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8876
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8867
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8863
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.8641
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.8629
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8533
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8520
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8516
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8507
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8504
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8479
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	4	0.8475
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8468
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8463
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8458
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8453
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8439
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8424
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8418
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8390
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8357
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.8261
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8255
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8242
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8233
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8209
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8138
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8086
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8085
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8076
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8041
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8019
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8009
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7988
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7987
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7969
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7961
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7958
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7893
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7892
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7891
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7869
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7854
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7830
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7827
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7817
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7804
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7779
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7767
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7767
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7752
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7750
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7737
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7670
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7667
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7655
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7645
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7640
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7630
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7610
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7550
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7534
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7510
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	5	0.7490
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	4	0.7468
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	4	0.7467
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	3	0.7457
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7445
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7407
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7405
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7380
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7376
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7376
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7373
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7372
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7366
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7353
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7350
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7343
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7328
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7319
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7310
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7308
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7307
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7307
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7286
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7285
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7278
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7277
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7268
Antiviral helicase SKI2	P35207	SKI2_YEAST	Saccharomyces cerevisiae	3	0.7257
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7242
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7227
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7210
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7201
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7175
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7169
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	5	0.7160
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7150
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7150
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7130
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7129
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7129
Ficolin-2	Q15485	FCN2_HUMAN	Homo sapiens	3	0.7127
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7124
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7121
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7120
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7116
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7108
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7102
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7098
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7095
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7089
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7081
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7076
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7068
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7068
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7043
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7039
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7023
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7022
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7022
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7021
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7020
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7019
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7015
BMP-2-inducible protein kinase	Q9NSY1	BMP2K_HUMAN	Homo sapiens	3	0.7002

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