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Piceid
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenol Glycoside Derivative
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc(/C=C/c3ccc(cc3)O)cc(c2)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1 |
| InChIKey | HSTZMXCBWJGKHG-CUYWLFDKSA-N |
| Formula | C20H22O8 |
| HBA | 8 |
| HBD | 6 |
| MW | 390.39 |
| Rotatable Bonds | 5 |
| TPSA | 139.84 |
| LogP | 0.45 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.3 |
| Exact Mass | 390.13 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ficus bubu | Moraceae | Plantae | 378014 |
| 2 | Nauclea pobeguinii | Rubiaceae | Plantae | 43525 |
Showing of synonyms
Piceid
27208-80-6
65914-17-2
Trans-Piceid
3,4,5-Trihydroxystilbene-3-beta-monoglucoside
3,4,5-Tsg
Resveratrol 3-beta-mono-D-glucoside
Resveratrol 3-O-beta-glucopyranoside
Resveratrol 3-O-beta-D-glucoside
UNII-XM261C37CQ
CHEBI:8198
XM261C37CQ
3,4'-5-Trihydroxystilbene-3-beta-D-glucopyranoside
Trans-resveratrol 3-beta-glucoside
Trans-resveratrol 3-beta-D-glucoside
Trans-resveratrol 3-O-beta-D-glucoside
3,4',5-trihydroxystilbene-3-beta-D-glucoside
3-Hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenyl-beta-D-glucoside
Resveratrol-3-O-b-mono-D-glucoside
5,4'-dihydroxystilbene-3-O-beta-D-glucopyranoside
Beta-D-Glucopyranoside, 3-hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenyl
Beta-D-Glucopyranoside, 3-hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenyl-, (E)-
Resveratrol-3-O-glucoside
DTXSID20897454
3-hydroxy-5-((E)-2-(4-hydroxyphenyl)ethenyl)phenyl beta-D-glucopyranoside
3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl beta-D-glucopyranoside
5,4'-dihydroxystilbene-3-O-beta-D-Glcp
Sooryehan Pure-Whitening
Sooryehan Pure-Whitening Essence
DTXCID101326795
Sooryehan Pure Whitening Spot Treatment
GLUCOPYRANOSIDE, 3-HYDROXY-5-(P-HYDROXYSTYRYL)PHENYL, beta-D-
5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)-1,3-BENZENEDIOL-3-beta-MONO-D-GLUCOSIDE
Beta-D-GLUCOPYRANOSIDE, 3-HYDROXY-5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)PHENYL
(2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-(4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
(2S,3R,4S,5S,6R)-2-(3-hydroxy-5-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
MLS001424114
B-D-Glucopyranoside, 3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenyl
3,5,4'-Trihydroxystilbene 3-glucoside
SMR000466371
MFCD00210592
(E/Z)-Piceid
Resveratrol 3-Glucoside
5-Tsg
Trans Resveratrol 3-O-b-D-glucopyranoside, 98%
E/Z-Polydatin
E/Z-Piceid
(E)-Piceid
5-Trihydroxystilbene-3-beta-monoglucoside
Resveratrol 3-O-glucoside
Resveratrol 5-O-glucoside
SCHEMBL41411
MLS000759499
Trans-Resveratrol 3-glucoside
CHEMBL142652
Resveratrol 3-beta-D-glucoside
Trans-Resveratrol 3-O-glucoside
BDBM60919
CHEBI:94610
Cid_5281718
DTXSID001030555
HMS2051A20
HY-N0120
MSK40284
LMPK13090012
S2390
AKOS015961013
CCG-100895
DB11263
KS-5384
MT06138
NC00145
Resveratrol 3-.beta.-mono-d-glucoside
NCGC00246971-01
NCGC00246971-04
NCGC00246971-10
(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
AS-13910
DA-69167
Trans-resveratrol 3-beta-d-glucopyranoside
1ST157306
CS-0007830
NS00069817
AB00639953-07
EN300-7416763
3,4',5-Trihydroxystilbene-3-b-D-glucopyranoside
Q3902665
RESVERATROL 3-.BETA.-MONO-D-GLUCOSIDE [MI]
Trans Resveratrol 3-O-beta-D-glucopyranoside, 98%
BRD-K43236057-001-07-1
3,4'-5-Trihydroxystilbene-3-beta-D-glucopyranoside, 97%
3,4'-5-TRIHYDROXYSTILBENE-3-.BETA.-D-GLUCOPYRANOSIDE
3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl-beta-D-glucopyranoside
3-Hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenyl beta-D-glucopyranoside
GLUCOPYRANOSIDE, 3-HYDROXY-5-(P-HYDROXYSTYRYL)PHENYL, .BETA.-D-
.BETA.-D-GLUCOPYRANOSIDE, 3-HYDROXY-5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)PHENYL
.BETA.-D-GLUCOPYRANOSIDE, 3-HYDROXY-5-(2-(4-HYDROXYPHENYL)ETHENYL)PHENYL
5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)-1,3-BENZENEDIOL-3-.BETA.-MONO-D-GLUCOSIDE
Polydatin
Resveratrol 3-O-b-D-glucopyranoside
Reservatrol-3-b-mono-D-glucoside
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-oxidanyl-phenoxy]oxane-3,4,5-triol
(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)vinyl]phenoxy]-6-methylol-tetrahydropyran-3,4,5-triol
(2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
.beta.-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl3,5,4'-Trihydroxystilbene 3-glucoside
- Kuete V, Sandjo LP, et al. (2015). Cytotoxicity of selected Cameroonian medicinal plants and Nauclea pobeguinii towards multi-factorial drug-resistant cancer cells.. BMC complementary and alternative medicine,2015, 15, 309. [View] [PubMed]
- Mbosso ETJ, Kamdem ML, et al. (2015). In Vitro Evaluation of Antimicrobial and Antiproliferative Activities for Compounds Isolated from the Ficus Bubu Warb. (Moraceae) Fruits: Chemotaxonomic Significance. Drug Delivery Letters,2015, 5(2), 122-131. [View]
Pubchem:
5281718
Cas:
27208-80-6
Zinc:
ZINC000004098633
Kegg Ligand:
C10275
Chebi:
8198
Nmrshiftdb2:
60021301
Metabolights:
MTBLC8198
Chembl:
CHEMBL142652
Comptox:
DTXSID20897454
Drugbank:
DB11263
Bindingdb:
60919
Selleck:
Polydatin(Piceid)
CPRiL:
55313
SMILES: c1ccccc1C=Cc2cc(ccc2)OC3CCCCO3
Level: 2
Mol. Weight: 390.39 g/mol
SMILES: c1ccccc1C=Cc2ccccc2
Level: 1
Mol. Weight: 390.39 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 390.39 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 390.39 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 390.39 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -6.56
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- 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)
- 0.980
- Plasma Protein Binding
- 81.69
- 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
- 11.630
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.170
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.840
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.620
- 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
- -10.040
- Rat (Acute)
- 2.220
- Rat (Chronic Oral)
- 3.880
- Fathead Minnow
- 4.160
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 507.940
- Hydration Free Energy
- -11.080
- Log(D) at pH=7.4
- 1.230
- Log(P)
- 0.73
- Log S
- -3.39
- Log(Vapor Pressure)
- -11.79
- Melting Point
- 193.31
- pKa Acid
- 6.23
- pKa Basic
- 4.01
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9599 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.9116 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9103 |
| Heat shock protein HSP 90-beta | P08238 | HS90B_HUMAN | Homo sapiens | 3 | 0.9011 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.9009 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.9009 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8974 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8761 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8744 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8727 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8705 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.8507 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.8329 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8312 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8238 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.8193 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8113 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8070 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7990 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7973 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7938 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7929 |
| Beta-secretase 2 | Q9Y5Z0 | BACE2_HUMAN | Homo sapiens | 3 | 0.7884 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7849 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7824 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7769 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7682 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.7678 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7659 |
| IOMT 3 | Q06YR3 | Q06YR3_MEDTR | Medicago truncatula | 3 | 0.7626 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7607 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7484 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 3 | 0.7480 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7473 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7435 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7410 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7386 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7384 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7346 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7336 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7309 |
| 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase | O33877 | FABA_PSEAE | Pseudomonas aeruginosa | 3 | 0.7296 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7288 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7237 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7224 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7216 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7216 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7213 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7211 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7211 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7209 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7126 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7119 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7110 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7090 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7089 |
| Glutathione S-transferase F2 | P46422 | GSTF2_ARATH | Arabidopsis thaliana | 3 | 0.7075 |
| 72 kDa type IV collagenase | P08253 | MMP2_HUMAN | Homo sapiens | 3 | 0.7042 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7015 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7010 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7008 |