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Luteolin di-O-acetyl-beta-D-glucuronide

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

Canonical Smiles	CC(=O)O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1OC(=O)C)O)C(=O)O)Oc1cc(O)cc2c1c(=O)cc(o2)c1ccc(c(c1)O)O
InChI	InChI=1S/C25H22O14/c1-9(26)35-21-20(32)22(24(33)34)39-25(23(21)36-10(2)27)38-18-7-12(28)6-17-19(18)15(31)8-16(37-17)11-3-4-13(29)14(30)5-11/h3-8,20-23,25,28-30,32H,1-2H3,(H,33,34)/t20-,21-,22-,23+,25+/m0/s1
InChIKey	CMSBJWWVFGGBLP-FPDJOHNTSA-N
Formula	C₂₅H₂₂O₁₄
HBA	13
HBD	5
MW	546.44
Rotatable Bonds	6
TPSA	219.49
LogP	0.99
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	39
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	546.1
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]

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cccc3OC4CCCCO4

Level: 2

Mol. Weight: 546.44 g/mol

SMILES: O=c1ccoc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 546.44 g/mol

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

Level: 1

Mol. Weight: 546.44 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 546.44 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 546.44 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 546.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.35
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.94
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.07
Plasma Protein Binding: 90.63
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: Inhibitor

Excretion

Clearance: 9.23
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.27
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.77
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.94
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: -1400.43
Rat (Acute): 2.22
Rat (Chronic Oral): 2.81
Fathead Minnow: 4.97
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 588.38
Hydration Free Energy: -3.41
Log(D) at pH=7.4: 0.38
Log(P): 1.07
Log S: -3.27
Log(Vapor Pressure): -13.21
Melting Point: 253.62
pKa Acid: 6.34
pKa Basic: 1.5

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9634
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.9497
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9399
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9323
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9050
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.9031
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8984
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8943
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8720
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8716
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8617
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8615
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8482
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8467
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8429
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8362
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8345
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8314
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8252
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8162
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8151
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.8105
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8097
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8086
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8035
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7995
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7986
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7924
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7916
Lipoprotein E	P26093	HEL_HAEIN	Haemophilus influenzae	4	0.7913
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7887
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7839
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7796
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7764
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7756
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7729
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7714
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7691
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7690
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7668
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7660
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7647
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7643
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7598
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7596
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7580
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7566
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7566
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7551
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7537
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7527
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7497
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7492
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7476
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7468
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7438
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.7426
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7426
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7391
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7376
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7374
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7371
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7347
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7347
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.7330
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7322
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7317
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.7316
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7308
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7302
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7301
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7282
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7279
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	4	0.7245
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7245
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7210
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7194
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7194
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7188
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7186
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7168
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7155
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.7136
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7136
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7130
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7114
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7097
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7088
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7072
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7070
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7064
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7061
Probable enoyl-CoA hydratase EchA8	P9WNN9	ECHA8_MYCTU	Mycobacterium tuberculosis	4	0.7041
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7036
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7027
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7027
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7023
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7012
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7012
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7002
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7002

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