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Vanillic acid 4-O-beta-D-glucopyranoside

Family: Plantae - Iridaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2ccc(cc2OC)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C14H18O9/c1-21-8-4-6(13(19)20)2-3-7(8)22-14-12(18)11(17)10(16)9(5-15)23-14/h2-4,9-12,14-18H,5H2,1H3,(H,19,20)/t9-,10-,11+,12-,14-/m1/s1
InChIKey	JYFOSWJYZIVJPO-YGEZULPYSA-N
Formula	C₁₄H₁₈O₉
HBA	8
HBD	5
MW	330.29
Rotatable Bonds	5
TPSA	145.91
LogP	-1.43
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	330.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Iris spuria	Iridaceae	Plantae	93026

Showing of synonyms

Farag SF, Kimura Y, et al. (2009). New isoflavone glycosides from Iris spuria L. (Calizona) cultivated in Egypt. Journal of Natural Medicines,2009,63(1),91-95. [View] [PubMed]

Pubchem: 14132337

Cas: 32142-31-7

Zinc: ZINC000013514036

Chebi: 68950

Nmrshiftdb2: 60024568

Metabolights: MTBLC68950

Comptox: DTXSID80556358

No compound-protein relationship available.

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 330.29 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 330.29 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 330.29 g/mol

Antiviral

Absorption

Caco-2 (logPapp): -6.03
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.020
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.820
Plasma Protein Binding: 71.97
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: 8.210
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.450
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.270
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.450
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: -0.830
Rat (Acute): 1.710
Rat (Chronic Oral): 3.830
Fathead Minnow: 3.860
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: 437.120
Hydration Free Energy: -18.530
Log(D) at pH=7.4: -1.820
Log(P): -0.89
Log S: -1.8
Log(Vapor Pressure): -11.4
Melting Point: 178.57
pKa Acid: 3.78
pKa Basic: 4.93

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.9406
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.9406
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.9041
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.9041
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8963
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8963
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8651
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8651
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8536
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8536
L-lactate dehydrogenase (cytochrome)	P00175	CYB2_YEAST	Saccharomyces cerevisiae	3	0.8488
L-lactate dehydrogenase (cytochrome)	P00175	CYB2_YEAST	Saccharomyces cerevisiae	3	0.8488
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8379
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8379
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.8314
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.8314
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	3	0.8266
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	3	0.8266
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8106
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8106
Bile salt hydrolase/transferase	P54965	CBH_CLOPE	Clostridium perfringens	3	0.8086
Bile salt hydrolase/transferase	P54965	CBH_CLOPE	Clostridium perfringens	3	0.8086
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8050
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8050
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7892
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7892
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7870
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7870
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7793
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7793
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7697
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7697
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7663
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7663
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.7544
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.7544
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7374
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7374
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7358
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7358
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7321
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7321
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7304
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7304
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7272
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7272
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7266
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7266
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7256
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7256
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7214
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7214
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7211
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7211
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7199
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7199
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7183
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7183
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7143
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7143
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7128
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7128
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.7122
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.7122
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7083
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7083
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7013
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7013
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7000
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7000

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