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Lucenin-2

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

Canonical Smiles	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)c([C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c(c2c1oc(cc2=O)c1ccc(c(c1)O)O)O
InChI	InChI=1S/C27H30O16/c28-5-12-17(33)21(37)23(39)26(42-12)15-19(35)14-10(32)4-11(7-1-2-8(30)9(31)3-7)41-25(14)16(20(15)36)27-24(40)22(38)18(34)13(6-29)43-27/h1-4,12-13,17-18,21-24,26-31,33-40H,5-6H2/t12-,13-,17-,18-,21+,22+,23-,24-,26+,27+/m1/s1
InChIKey	ZLPSOQFIIQIIAX-VQVVXJKKSA-N
Formula	C₂₇H₃₀O₁₆
HBA	16
HBD	12
MW	610.52
Rotatable Bonds	5
TPSA	291.43
LogP	-2.69
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	Artemisia herba-alba	Asteraceae	Plantae	72329
2	Artemisia monosperma	Asteraceae	Plantae	72348
3	Artemisia monosperma	Asteraceae	Plantae	72348
4	Phlomis aurea	Lamiaceae	Plantae	997702
5	Phlomis floccosa	Lamiaceae	Plantae	572125
6	Phlomis floccosa	Labiateae	Plantae	572125
7	Stachys aegyptiaca	Lamiaceae	Plantae	1391947

Showing of synonyms

El-Ansari M, Abdalla M, et al. (1991). Flavonoid constituents of Stachys aegyptiaca. Phytochemistry, 1991,30(4),1169-1173. [View]
Saleh NAM, El-Newumy SI, et al. (1985). Flavonoid glycosides of Artemisia monosperma and A. herba-alba.. Phytochemistry,1985,24(1),201-203. [View]
Saleh NAM, El-Negoumy SI, et al. (1987). Flavonoids of Artemisia judaica, A. monosperma and A. Herba-alba.. Phytochemistry,1987,26(11),3059-3064. [View]
El-Negoumy S, Abdalla M, et al. (1986). Flavonoids of Phlomis Aurea and P. Floccosa. Phytochemistry, 1986, 25(3), 772-774.. [View]

Pubchem: 442615

Cas: 29428-58-8

Zinc: ZINC000004098553

Kegg Ligand: C10102

Chebi: 6553

Nmrshiftdb2: 60025354

Comptox: DTXSID00331881

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(C4CCCCO4)cc(c3)C5CCCCO5

Level: 3

Mol. Weight: 610.52 g/mol

SMILES: O=c1ccoc(c12)c(C3CCCCO3)cc(c2)C4CCCCO4

Level: 2

Mol. Weight: 610.52 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 610.52 g/mol

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 610.52 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 610.52 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 610.52 g/mol

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

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): -6.38
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -6.420
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 12.16

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.490
Plasma Protein Binding: 61.74
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: 8.810
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.750
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.770
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.630
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: -13854.860
Rat (Acute): 2.390
Rat (Chronic Oral): 5.020
Fathead Minnow: 27.190
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 580.700
Hydration Free Energy: -3.130
Log(D) at pH=7.4: -2.210
Log(P): -0.82
Log S: -3.28
Log(Vapor Pressure): -15.28
Melting Point: 212.92
pKa Acid: 0.77
pKa Basic: 12.46

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8728
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8728
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8304
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8304
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8301
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8301
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8265
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8265
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8242
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8242
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8201
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8201
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8019
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8019
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7679
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7679
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7641
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7641
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7593
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7593
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7529
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7529
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7479
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7479
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7373
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7373
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7372
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7372
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7206
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7206
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7203
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7203
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7093
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7093
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7045
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7045
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7030
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7030
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7012
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7012

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