Stachyose

Details

• Internal ID: 6bfc91a1-f512-4f01-820f-f40413f874d6
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: (2S,3R,4S,5R,6R)-2-[[(2R,3R,4S,5R,6S)-6-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)OCC3C(C(C(C(O3)OC4(C(C(C(O4)CO)O)O)CO)O)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC[C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)OC[C@@H]3[C@H]([C@@H]([C@H]([C@H](O3)O[C@]4([C@H]([C@@H]([C@H](O4)CO)O)O)CO)O)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C24H42O21/c25-1-6-10(28)14(32)17(35)21(41-6)39-3-8-11(29)15(33)18(36)22(42-8)40-4-9-12(30)16(34)19(37)23(43-9)45-24(5-27)20(38)13(31)7(2-26)44-24/h6-23,25-38H,1-5H2/t6-,7-,8-,9-,10+,11+,12-,13-,14+,15+,16+,17-,18-,19-,20+,21+,22+,23-,24+/m1/s1
• InChI Key: UQZIYBXSHAGNOE-XNSRJBNMSA-N
• Popularity: 2,406 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₂O₂₁
• Molecular Weight: 666.60 g/mol
• Exact Mass: 666.22185834 g/mol
• Topological Polar Surface Area (TPSA): 348.00 Ų
• XlogP: -8.00
• Atomic LogP (AlogP): -9.75
• H-Bond Acceptor: 21
• H-Bond Donor: 14
• Rotatable Bonds: 11

Synonyms

• D-Stachyose
• 470-55-3
• Lupeose
• CHEBI:17164
• stachyose hydrate
• UNII-25VX64653N
• EINECS 207-427-3
• 10094-58-3
• O-alpha-D-galactopyranosyl-(1->6)o-alpha-D-galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-beta-D-fructofuranoside
• Manneotetrose
• alpha-D-Galp-(1->6)-alpha-D-Galp-(1->6)-alpha-D-Glcp-(1->2)-beta-D-Fruf
• alpha-D-Galp-(1->6)-alpha-D-Galp-(1->6)-alpha-D-Glcp-(1<->2)-beta-D-Fruf
• beta-D-fructofuranosyl alpha-D-galactopyranosyl-(1->6)-alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranoside
• 54261-98-2
• Stachyose hydrate from Stachys tuberifera
• DTXSID30889345
• (2R,3R,4S,5S,6R)-2-(((2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-((2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl)oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxy-3,4,5-trihydroxy-oxan-2-yl)methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• .alpha.-D-Glucopyranoside, .beta.-D-fructofuranosyl O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-, hydrate
• bmse000240
• Epitope ID:150068
• C01613
• SCHEMBL32922
• CHEMBL1625803
• UQZIYBXSHAGNOE-XNSRJBNMSA-N
• DTXCID601324144
• .alpha.-D-Glucopyranoside, .beta.-D-fructofuranosyl O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-
• alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1->6)-O-alpha-D-galactopyranosyl-(1->6)-
• HY-N7910
• MFCD00006631
• AKOS016009597
• NCGC00246978-01
• CS-0138789
• S0397
• F77877
• Q283435
• GAL(alpha1->6)GAL(alpha1->6)GLC(alpha1->2beta)FRU
• alpha-D-Gal-(1->6)-alpha-D-Gal-(1->6)-alpha-D-Glc-(1->2)-beta-D-Fru
• alpha-D-Galp-(1->6)-alpha-D-Galp-(1->6)-alpha-D-Glcp-(12)-beta-D-Fruf
• (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-((((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
• (2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1->6)-O-alpha-D-galactopyranosyl-(1->6)-alpha-D-Glucopyranoside
• beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1-6)-O-alpha-D-galactopyranosyl-(1-6)-alpha-D-galactopyranoside
• beta-D-Fructofuranosyl O-alpha-D-Galactopyranosyl-(1-6)-O-alpha-D-galactopyranosyl-(1-6)-alpha-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9685	96.85%
Caco-2	-	0.8995	89.95%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7796	77.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9202	92.02%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6420	64.20%
P-glycoprotein inhibitior	-	0.5055	50.55%
P-glycoprotein substrate	-	0.9446	94.46%
CYP3A4 substrate	+	0.5137	51.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8378	83.78%
CYP3A4 inhibition	-	0.9410	94.10%
CYP2C9 inhibition	-	0.9095	90.95%
CYP2C19 inhibition	-	0.8373	83.73%
CYP2D6 inhibition	-	0.9278	92.78%
CYP1A2 inhibition	-	0.9418	94.18%
CYP2C8 inhibition	-	0.8004	80.04%
CYP inhibitory promiscuity	-	0.8369	83.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6497	64.97%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9193	91.93%
Skin irritation	-	0.8917	89.17%
Skin corrosion	-	0.9712	97.12%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7482	74.82%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.9425	94.25%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.5831	58.31%
Acute Oral Toxicity (c)	IV	0.5888	58.88%
Estrogen receptor binding	+	0.6532	65.32%
Androgen receptor binding	-	0.4843	48.43%
Thyroid receptor binding	-	0.5230	52.30%
Glucocorticoid receptor binding	-	0.6716	67.16%
Aromatase binding	+	0.7040	70.40%
PPAR gamma	+	0.6110	61.10%
Honey bee toxicity	-	0.7051	70.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	-	0.7319	73.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2094128	P24941	Cyclin-dependent kinase 2/cyclin A	16 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.71%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	90.45%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.21%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.80%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	85.32%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.19%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.75%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.65%	95.83%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.41%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.66%	94.00%

Plants that contains it

• Allium sativum
• Allium stipitatum
• Alstonia longifolia
• Amaranthus cruentus
• Angiopteris evecta
• Artemisia argentea
• Asphodeline damascena
• Brodiaea californica
• Cajanus cajan
• Centella asiatica
• Cyathula tomentosa
• Echinostephia aculeata
• Eucalyptus kitsoniana
• Euphorbia antiquorum
• Exochorda racemosa subsp. giraldii
• Glycine max
• Gossypium hirsutum
• Hemionitis lemmonii
• Himantoglossum hircinum
• Kopsia arborea
• Lepidophorum repandum
• Lonicera caerulea
• Lupinus albus
• Lupinus mutabilis
• Myristica malabarica
• Nicotiana tabacum
• Odontites vernus
• Olea europaea
• Phaseolus coccineus
• Plagiomnium cuspidatum
• Plantago asiatica
• Plectranthus lanuginosus
• Populus yunnanensis
• Rehmannia glutinosa
• Rhodanthe maryonii
• Rhododendron campylocarpum
• Rosulabryum capillare
• Sagina japonica
• Scabiosa comosa
• Scapania aequiloba
• Solanum dulcamara
• Spartium junceum
• Toddalia asiatica
• Trigonella foenum-graecum
• Vachellia lasiopetala
• Vigna unguiculata
• Xerosicyos danguyi

Cross-Links

• PubChem: 439531
• NPASS: NPC83963
• LOTUS: LTS0062089
• wikiData: Q283435