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6-hydroxyluteoline glucosylglucuronide

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

Canonical Smiles	Oc1ccc(cc1O)c1c(c(=O)c2c(o1)cc(c(c2O)O)O)O[C@@H]1O[C@H](COC2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C27H28O19/c28-7-2-1-6(3-8(7)29)22-23(16(34)12-10(43-22)4-9(30)13(31)15(12)33)45-27-21(39)17(35)14(32)11(44-27)5-42-26-20(38)18(36)19(37)24(46-26)25(40)41/h1-4,11,14,17-21,24,26-33,35-39H,5H2,(H,40,41)/t11-,14-,17+,18+,19+,20-,21-,24+,26?,27+/m1/s1
InChIKey	RWJSCBIRXWFMEU-RJXGKAPQSA-N
Formula	C₂₇H₂₈O₁₉
HBA	18
HBD	12
MW	656.5
Rotatable Bonds	7
TPSA	326.96
LogP	-2.92
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.41
Exact Mass	656.12
Number of Lipinski Rule Violations	3

#	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: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 656.5 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 656.5 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 656.5 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 656.5 g/mol

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

Level: 1

Mol. Weight: 656.5 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 656.5 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 656.5 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 656.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 656.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.67
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.670
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 29.69

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.670
Plasma Protein Binding: 55.91
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: 11.020
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.980
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.990
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.470
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: -49087.530
Rat (Acute): 2.030
Rat (Chronic Oral): 4.770
Fathead Minnow: 80.730
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: 343.770
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -3.640
Log(P): -1.25
Log S: -3.94
Log(Vapor Pressure): -33.41
Melting Point: 211.85
pKa Acid: 0.63
pKa Basic: 10.65

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9625
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.9035
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8852
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8747
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8479
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8467
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.8461
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8435
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8354
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.8353
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8215
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8161
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8112
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7985
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7982
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7956
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7902
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7895
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7893
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7892
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7891
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7839
Ficolin-2	Q15485	FCN2_HUMAN	Homo sapiens	3	0.7833
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7832
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7777
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	5	0.7773
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7673
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7665
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7654
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7608
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7595
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7568
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7452
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7397
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7388
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7375
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7363
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7359
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7274
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7273
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7273
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7270
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7264
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7227
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7225
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7203
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7194
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7172
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7158
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7147
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7115
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7038
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7005

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