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Cis-1-p-coumaroyl-beta-D-glucopyranoside

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Polyphenol

Canonical Smiles	OC[C@H]1O[C@](O)(C(=O)/C=C\c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(22,23-10)11(18)6-3-8-1-4-9(17)5-2-8/h1-6,10,12-14,16-17,19-22H,7H2/b6-3-/t10-,12-,13+,14-,15-/m1/s1
InChIKey	MJJGRZPNGCFWQB-LSSWKVNRSA-N
Formula	C₁₅H₁₈O₈
HBA	8
HBD	6
MW	326.3
Rotatable Bonds	4
TPSA	147.68
LogP	-1.86
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	326.1
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Joannesia princeps	Euphorbiaceae	Plantae	179690

Showing of synonyms

Camero C, Temraz A, et al. (2017). Phytochemical study of Joannesia princeps Vell. (Euphorbiaceae) leaves.. Biochemical Systematics and Ecology, 2017, 70, 69-72. [View]

No compound-protein relationship available.

SMILES: O1CCCCC1C(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 326.3 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 326.3 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 326.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.42
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.0
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.69
Plasma Protein Binding: 63.35
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: 5.1
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.07
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.26
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.03
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: -3.1
Rat (Acute): 2.21
Rat (Chronic Oral): 3.6
Fathead Minnow: 3.65
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: 508.5
Hydration Free Energy: -19.61
Log(D) at pH=7.4: -0.64
Log(P): -1.01
Log S: -1.46
Log(Vapor Pressure): -14.34
Melting Point: 170.08
pKa Acid: 4.23
pKa Basic: 7.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9518
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9038
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8952
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8939
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8901
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8819
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8807
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8736
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8731
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8729
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8709
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8702
Leucine--tRNA ligase	P07813	SYL_ECOLI	Escherichia coli	4	0.8690
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8688
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8678
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8642
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8511
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8412
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8399
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8395
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8348
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8272
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8270
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.8257
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8201
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8194
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8190
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8188
tRNA(Phe) (4-demethylwyosine(37)-C(7)) aminocarboxypropyltransferase	O58523	TYW2_PYRHO	Pyrococcus horikoshii	3	0.8113
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.8066
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7912
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7907
Putative adenosine kinase	G4V7G8	G4V7G8_SCHMA	Schistosoma mansoni	5	0.7819
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7762
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7749
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7732
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7686
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7663
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7647
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7616
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7576
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7566
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7519
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7502
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7499
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7498
Type II methyltransferase M.RsrI	P14751	MTR1_RHOSH	Cereibacter sphaeroides	4	0.7495
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7473
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7446
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7440
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7432
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7418
7-methylguanosine phosphate-specific 5'-nucleotidase	Q9W197	5NT3B_DROME	Drosophila melanogaster	4	0.7413
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7409
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7405
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7399
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7378
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7373
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	3	0.7371
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7355
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7351
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7344
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7319
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7316
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7295
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7288
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7284
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7271
Genome polyprotein	Q9WLZ5	Q9WLZ5_9FLAV	dengue virus type 2	3	0.7257
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7255
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7206
Serine/threonine-protein kinase RAD53	P22216	RAD53_YEAST	Saccharomyces cerevisiae	4	0.7191
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7189
Genome polyprotein	Q8QL64	Q8QL64_9FLAV	Modoc virus	3	0.7188
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7184
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7173
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7171
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7166
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.7160
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7159
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7156
Myosin heavy chain, striated muscle	P24733	MYS_ARGIR	Argopecten irradians	3	0.7155
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7154
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7154
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7139
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7137
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7129
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7125
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein	Q5SHN1	Q5SHN1_THET8	Thermus thermophilus	3	0.7123
Histone acetyltransferase GCN5	Q27198	Q27198_TETTH	Tetrahymena thermophila	3	0.7121
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7119
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7118
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7103
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7101
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7101
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	2	0.7096
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7077
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7070
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7067
Genome polyprotein	P03314	POLG_YEFV1	Yellow fever virus	4	0.7059
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7055
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7054
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7050
Glutamate--cysteine ligase	P32477	GSH1_YEAST	Saccharomyces cerevisiae	3	0.7035
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7032
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7030
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7027
Genome polyprotein	A9LIE0	A9LIE0_9FLAV	dengue virus type 3	3	0.7017
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7016
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7006
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7002

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