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Lanceoloside A

Family: Plantae - Ochnaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Benzoylglucoside

Canonical Smiles	Oc1ccc(cc1)O[C@H]1O[C@@H](COC(=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C19H20O9/c20-11-3-1-10(2-4-11)18(25)26-9-14-15(22)16(23)17(24)19(28-14)27-13-7-5-12(21)6-8-13/h1-8,14-17,19-24H,9H2/t14-,15-,16+,17-,19-/m0/s1
InChIKey	FTFZXPBVBBJTHV-LVEJAMMSSA-N
Formula	C₁₉H₂₀O₉
HBA	9
HBD	5
MW	392.36
Rotatable Bonds	5
TPSA	145.91
LogP	0.14
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	392.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rhabdophyllum arnoldianum	Ochnaceae	Plantae	1501067

Showing of synonyms

Mbing JN, Missi MB, et al. (2014). New flavonoids C-glycosides from Rhabdophyllum arnoldianum.. Natural product research,2014, 28(8), 539-544. [View] [PubMed]

Pubchem: 133556315

Cas: 63555-02-2

Nmrshiftdb2: 70128409

CPRiL: 422438

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 392.36 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 392.36 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 392.36 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 392.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 392.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.53
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.110
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.8

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.890
Plasma Protein Binding: 76.75
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: 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: 12.560
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.640
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.990
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.610
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: -8.680
Rat (Acute): 2.160
Rat (Chronic Oral): 3.530
Fathead Minnow: 4.130
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 494.030
Hydration Free Energy: -11.210
Log(D) at pH=7.4: 1.460
Log(P): 0.84
Log S: -3.59
Log(Vapor Pressure): -9.92
Melting Point: 193.82
pKa Acid: 6.3
pKa Basic: 2.63

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9583
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9540
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9268
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9174
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8816
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8816
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8699
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8678
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8637
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8536
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8524
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8487
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8450
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8408
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8367
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8305
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8302
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8280
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8279
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8272
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8201
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8156
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8138
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8101
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	3	0.8091
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8049
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8012
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8009
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7926
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7915
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	4	0.7881
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7826
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7820
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7817
Flavonoid 3-O-glucosyltransferase	A6XNC6	UGFGT_MEDTR	Medicago truncatula	3	0.7803
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7796
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7776
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7764
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	2	0.7753
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7744
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7736
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7720
Protein UshA	P07024	USHA_ECOLI	Escherichia coli	3	0.7720
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7702
Coniferyl alcohol 9-O-methyltransferase	A6XNE6	A6XNE6_9ROSI	Linum nodiflorum	3	0.7682
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7641
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7629
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7613
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7607
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7593
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7590
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7587
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7552
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7526
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7506
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7504
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7494
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7478
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7463
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7451
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7440
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7386
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7350
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7349
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7339
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7330
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7320
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7317
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7316
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7312
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7308
Repressor protein	Q7X0D9	Q7X0D9_ACIAD	Acinetobacter baylyi	3	0.7288
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7283
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7281
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7261
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7259
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7258
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7255
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7244
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7236
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7225
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7208
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7197
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7196
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7187
Gag-Pol polyprotein	P04587	POL_HV1B5	Human immunodeficiency virus type 1 group M subtype B	3	0.7184
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7176
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7173
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7168
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7156
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7150
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7150
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	3	0.7144
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7135
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7132
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7123
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	4	0.7116
Sensor histidine kinase EnvZ	P0AEJ4	ENVZ_ECOLI	Escherichia coli	3	0.7116
Polymerase basic protein 2	Q2LG68	Q2LG68_9INFA	Influenza A virus)	4	0.7114
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7105
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7098
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7094
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7088
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	3	0.7087
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7080
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7077
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7071
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7056
Exotoxin A	P11439	TOXA_PSEAE	Pseudomonas aeruginosa	3	0.7051
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7048
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7039
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7028
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7021
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7006
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7005
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7000

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