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Luteolin diglucuronide

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

Canonical Smiles	OC(=O)[C@H]1OC(Oc2cc(OC3O[C@H](C(=O)O)[C@H]([C@@H]([C@H]3O)O)O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C27H26O18/c28-9-2-1-7(3-10(9)29)12-6-11(30)15-13(42-12)4-8(41-26-20(35)16(31)18(33)22(44-26)24(37)38)5-14(15)43-27-21(36)17(32)19(34)23(45-27)25(39)40/h1-6,16-23,26-29,31-36H,(H,37,38)(H,39,40)/t16-,17-,18-,19-,20+,21+,22-,23-,26?,27?/m0/s1
InChIKey	JMMARVBBPNTRDQ-GKKHVXDVSA-N
Formula	C₂₇H₂₆O₁₈
HBA	16
HBD	10
MW	638.49
Rotatable Bonds	7
TPSA	303.57
LogP	-2.59
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.37
Exact Mass	638.11
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Convolvulus althaeoides	Convolvulaceae	Plantae	267570

Showing of synonyms

Hrichi S, Chaabane-Banaoues R, et al. (2020). Effect of seasonal variation on the chemical composition and antioxidant and antifungal activities of Convolvulus althaeoides L. leaf extract. Arabian Journal of Chemistry, 2020, 13(6), 5651-5668. [View]

Pubchem: 21309398

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(OC4CCCCO4)cc3OC5CCCCO5

Level: 3

Mol. Weight: 638.49 g/mol

SMILES: O=c1ccoc(c12)cc(OC3CCCCO3)cc2OC4CCCCO4

Level: 2

Mol. Weight: 638.49 g/mol

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

Level: 2

Mol. Weight: 638.49 g/mol

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

Level: 2

Mol. Weight: 638.49 g/mol

SMILES: O=c1ccoc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 638.49 g/mol

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

Level: 1

Mol. Weight: 638.49 g/mol

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

Level: 1

Mol. Weight: 638.49 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 638.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 638.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 638.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.68
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.45
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 18.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.01
Plasma Protein Binding: 73.51
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: 1.59
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.27
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.82
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.49
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: -31008.41
Rat (Acute): 1.96
Rat (Chronic Oral): 4.97
Fathead Minnow: 56.58
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 460.6
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -3.64
Log(P): -2.32
Log S: -4.01
Log(Vapor Pressure): -20.03
Melting Point: 261.66
pKa Acid: 2.33
pKa Basic: 7.02

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	0.9410
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9286
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9198
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9052
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8848
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8698
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8654
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8529
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8506
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8438
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8362
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8250
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8241
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8193
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8164
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8047
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7973
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7897
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7873
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7809
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7760
6-phosphogluconate dehydrogenase, decarboxylating	P96789	6PGD_LACLM	Lactococcus lactis subsp. cremoris	4	0.7748
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7733
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7692
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7623
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7609
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7586
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7563
Ficolin-2	Q15485	FCN2_HUMAN	Homo sapiens	3	0.7561
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7537
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7519
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	3	0.7452
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7434
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7367
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7308
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7305
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	3	0.7302
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7291
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7282
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7249
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7248
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7205
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7122
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7087
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7077
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7072
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7066
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7050
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7014
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7006
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7005

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