ANPDB

Select a section from the left sidebar

Verproside

Family: Plantae - Scrophulariaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Iridoid Glucoside

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3OC(=O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C22H26O13/c23-6-12-14(27)15(28)16(29)21(32-12)34-20-13-9(3-4-31-20)17(18-22(13,7-24)35-18)33-19(30)8-1-2-10(25)11(26)5-8/h1-5,9,12-18,20-21,23-29H,6-7H2/t9-,12-,13-,14-,15+,16-,17+,18+,20+,21+,22-/m1/s1
InChIKey	DBUOUVZMYWYRRI-YWEKDMGLSA-N
Formula	C₂₂H₂₆O₁₃
HBA	13
HBD	7
MW	498.44
Rotatable Bonds	6
TPSA	208.13
LogP	-2.31
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.59
Exact Mass	498.14
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Veronica anagalIis-aquatica	Scrophulariaceae	Plantae	1421714

Showing of synonyms

Lahloub M, Zaghloul M, et al. (1993). Iridoid glycosides from veronica anagallis-aquatica. Phytochemistry, 1993, 33(2), 401-405. [View]

Pubchem: 12000799

Cas: 50932-20-2

Gnps: CCMSLIB00004687155

Zinc: ZINC000049777014

Chebi: 69798

Nmrshiftdb2: 60075193

Metabolights: MTBLC69798

Chembl: CHEMBL1082144

CPRiL: 159750

SMILES: c1ccccc1C(=O)OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5

Level: 2

Mol. Weight: 498.44 g/mol

SMILES: c1ccccc1C(=O)OC(C(O2)C23)C4C3COC=C4

Level: 1

Mol. Weight: 498.44 g/mol

SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 498.44 g/mol

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 498.44 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 498.44 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 498.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.82
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.210
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.93

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.670
Plasma Protein Binding: 41.4
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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.800
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.950
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.560
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.100
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: -621.490
Rat (Acute): 2.610
Rat (Chronic Oral): 3.720
Fathead Minnow: 3.830
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 568.430
Hydration Free Energy: -3.170
Log(D) at pH=7.4: -1.340
Log(P): -1.21
Log S: -2.15
Log(Vapor Pressure): -13.01
Melting Point: 168.08
pKa Acid: 4.85
pKa Basic: 3.63

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.9284
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9192
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9079
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9058
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8876
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8678
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8515
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8285
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8244
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8218
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8155
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8153
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7962
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7951
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7929
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7896
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7864
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7857
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7798
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7783
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7744
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7739
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7739
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7725
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7699
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7614
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7571
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7533
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7525
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7515
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7462
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7431
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7430
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7371
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7351
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7317
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7315
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7307
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7278
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7278
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7278
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7270
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7257
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7255
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7248
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7246
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7222
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7179
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.7177
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7177
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7163
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7156
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7152
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7151
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7137
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7136
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7134
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7134
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7120
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7110
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7100
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7097
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7093
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7079
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7069
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7067
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7066
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7048
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7040
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7039
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7017
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7017

Download SDF