Gastrodin

Details

• Internal ID: 7152e8b9-0740-4d03-bac3-2b5d490a1586
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• InChI: InChI=1S/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
• InChI Key: PUQSUZTXKPLAPR-UJPOAAIJSA-N
• Popularity: 767 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₈O₇
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.10525291 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.64
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 62499-27-8
• Gastrodine
• 5YS9U2W3RQ
• DTXSID30978086
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• beta-D-Glucopyranoside, 4-(hydroxymethyl)phenyl
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)oxane-3,4,5-triol
• RefChem:37313
• DTXCID301405414
• Gastrodin Hemihydrate
• b-D-Glucopyranoside, 4-(hydroxymethyl)phenyl
• 4-(Hydroxymethyl)phenyl beta-D-Glucopyranoside
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol
• CHEMBL274739
• CHEBI:80828
• MFCD00272169
• UNII-5YS9U2W3RQ
• ss-D-Glucopyranoside, 4-(hydroxymethyl)phenyl; 4-(Hydroxymethyl)phenyl ss-D-glucopyranoside; 4-(ss-D-Glucopyranosyl)-benzylalcohol; 4-(ss-D-Glucopyranosyloxy)benzyl alcohol; 4-Hydroxybenzyl alcohol 4-O-ss-D-glucopyranoside; Gastrodin
• Gastrodin (Standard)
• Gastrodin (Gastrodine)
• GASTRODIN [MI]
• (-)-GASTRODIN
• 4-(Hydroxymethyl)phenyl-beta-D-glucopyranoside
• GASTRODIN [WHO-DD]
• orb1304755
• SCHEMBL1076037
• Gastrodin, >=98% (HPLC)
• HY-N0115R
• GLXC-03177
• HMS3884L15
• HY-N0115
• MSK40094
• 2424AH
• BDBM50177403
• s2383
• AKOS015951256
• AC-8028
• BCP9000710
• CCG-267336
• CS-7969
• MG11579
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]tetrahydropyran-3,4,5-triol
• NCGC00346601-02
• 4Hydroxybenzyl alcohol 4-O-b-D-glucoside
• AS-17473
• DA-53519
• Gastrodin, from Gastrodia alata, >=98%
• SY076539
• 4-[beta-d-glucopyranosyloxy] benzyl alcohol
• AB1009350
• b-D-Glucopyranoside,4-(hydroxymethyl)phenyl
• NS00124520
• 4-(Hydroxymethyl)phenylbeta-D-Glucopyranoside
• C16964
• 4-(.BETA.-D-GLUCOPYRANOSYL)-BENZYLALCOHOL
• 499G278
• A833810
• F808012
• Q5526833
• 4-(.BETA.-D-GLUCOPYRANOSYLOXY)BENZYL ALCOHOL
• .BETA.-D-GLUCOPYRANOSIDE, 4-(HYDROXYMETHYL)PHENYL
• .BETA.-D-GLUCOPYRANOSIDE, 4-(HYDROXYMETHYL)PHENYL-
• 4-HYDROXYBENZYL ALCOHOL 4-O-.BETA.-D-GLUCOPYRANOSIDE
• NCGC00346601-02_C13H18O7_beta-D-Glucopyranoside, 4-(hydroxymethyl)phenyl
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triol
• 4-(Hydroxymethyl)phenyl beta-D-glucopyranoside; (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8854	88.54%
Caco-2	-	0.7988	79.88%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6608	66.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9460	94.60%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9099	90.99%
P-glycoprotein inhibitior	-	0.9502	95.02%
P-glycoprotein substrate	-	0.9811	98.11%
CYP3A4 substrate	-	0.5703	57.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8134	81.34%
CYP3A4 inhibition	-	0.9261	92.61%
CYP2C9 inhibition	-	0.8929	89.29%
CYP2C19 inhibition	-	0.8794	87.94%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.9425	94.25%
CYP2C8 inhibition	-	0.8091	80.91%
CYP inhibitory promiscuity	-	0.7107	71.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5832	58.32%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.8928	89.28%
Skin irritation	-	0.8432	84.32%
Skin corrosion	-	0.9721	97.21%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6820	68.20%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.8706	87.06%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	-	0.8098	80.98%
Acute Oral Toxicity (c)	III	0.6096	60.96%
Estrogen receptor binding	-	0.7450	74.50%
Androgen receptor binding	-	0.6201	62.01%
Thyroid receptor binding	-	0.5121	51.21%
Glucocorticoid receptor binding	-	0.6107	61.07%
Aromatase binding	-	0.6215	62.15%
PPAR gamma	+	0.6678	66.78%
Honey bee toxicity	-	0.7870	78.70%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7050	70.50%
Fish aquatic toxicity	-	0.5754	57.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.68%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.59%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.37%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.32%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.99%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.30%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.33%	86.92%
CHEMBL2581	P07339	Cathepsin D	84.95%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	82.02%	94.73%
CHEMBL4208	P20618	Proteasome component C5	81.54%	90.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.47%	83.57%

Plants that contains it

• Anethum graveolens
• Anoectochilus formosanus
• Anoectochilus koshunensis
• Artemisia dracunculus
• Astilbe rubra
• Bletilla formosana
• Boronia muelleri
• Citrullus colocynthis
• Colchicum macedonicum
• Coprosma acerosa
• Coptis deltoidea
• Cranfillia vulcanica
• Cremastra appendiculata
• Cyrtosia septentrionalis
• Dactylorhiza hatagirea
• Dalbergia frutescens
• Dicliptera riparia
• Dillenia papuana
• Euphorbia caducifolia
• Ficus elastica
• Galeola faberi
• Gastrodia elata
• Gymnadenia conopsea
• Hypericum papuanum
• Ilex kaushue
• Inula thapsoides
• Kaunia longipetiolata
• Limeum pterocarpum
• Lupinus formosus
• Oxandra xylopioides
• Palicourea alpina
• Pleione bulbocodioides
• Pleione yunnanensis
• Polygonum thunbergii
• Posoqueria latifolia
• Pyrus communis
• Rhodomyrtus tomentosa
• Salix sieboldiana
• Salvia xalapensis
• Sambucus ebulus
• Scrophularia smithii
• Senna spectabilis var. spectabilis
• Sicana odorifera
• Solanum torvum
• Tanacetum sinaicum
• Trifolium alexandrinum
• Trifolium pratense
• Vincetoxicum indicum var. glabrum
• Wunderlichia mirabilis
• Zilla spinosa

Cross-Links

• PubChem: 115067
• NPASS: NPC269242
• LOTUS: LTS0027222
• wikiData: Q5526833