Validamycin A

Details

• Internal ID: 00782b27-bf26-462f-861d-d98ffe8d386f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(C(C1NC2C=C(C(C(C2O)O)O)CO)O)O)OC3C(C(C(C(O3)CO)O)O)O)CO
• SMILES (Isomeric): C1[C@@H]([C@H]([C@@H]([C@H]([C@H]1N[C@H]2C=C([C@H]([C@@H]([C@H]2O)O)O)CO)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO
• InChI: InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1
• InChI Key: JARYYMUOCXVXNK-CSLFJTBJSA-N
• Popularity: 80 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₅NO₁₃
• Molecular Weight: 497.50 g/mol
• Exact Mass: 497.21084017 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: -6.30
• Atomic LogP (AlogP): -6.75
• H-Bond Acceptor: 14
• H-Bond Donor: 12
• Rotatable Bonds: 7

Synonyms

• VALIDAMYCIN A
• 37248-47-8
• Valimon
• jinggangmycin
• T-7545-A
• 313E9620QS
• (2R,3R,4S,5S,6R)-2-[(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• DTXSID4058073
• CHEBI:29703
• (1S-(1alpha,4alpha,5beta,6alpha))-1,5,6-trideoxy-4-O-beta-D-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-D-chiro-inositol
• 1L-(1,3,4/2,6)-2,3-Dihydroxy-6-hydroxymethyl-4-((1S,4R,5S,6S)-4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-enylamino)cyclohexyl beta-D-glucopyranoside
• D-1,5,6-Trideoxy-3-O-beta-D-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-D-chiroinositol
• (1S-(1a,4a,5B,6a))-1,5,6-Trideoxy-3-O-B-D-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-d-chiro-inositol
• 1L-(1,3,4/2,6)-2,3-Dihydroxy-6-hydromethyl-4-((1S,4R,5S,6S)-4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-enylamino)cyclohexyl beta-D-glucopyranoside
• (1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexyl beta-D-glucopyranoside
• (2R,3R,4S,5S,6R)-2-[(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]cyclohexoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• D-chiro-Inositol, 1,5,6-trideoxy-3-O-beta-D-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-, (1S-(1-alpha,4-alpha,5-beta,6-alpha))-
• (1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl)amino)cyclohexyl beta-D-glucopyranoside
• (2R,3R,4S,5S,6R)-2-((1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl)amino)cyclohexoxy)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-((1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl)amino)cyclohexyl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• RefChem:193569
• DTXCID0031841
• (2R,5S)-2-((1R,2R,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl)amino)cyclohexyl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 609-372-4
• D-CHIRO-INOSITOL, 1,5,6-TRIDEOXY-4-O-BETA-D-GLUCOPYRANOSYL-5-(HYDROXYMETHYL)-1-(((1S,4R,5S,6S)-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOHEXEN-1-YL)AMINO)-
• Validacin
• MFCD09028089
• (2R,3R,4S,5S,6R)-2-(((1R,2R,3S,4S,6R)-2,3-Dihydroxy-6-(hydroxymethyl)-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl)amino)cyclohexyl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• Validamycin A (>70%) Hydrochloride Salt
• Cepex 10SL; Validacin
• jinganmycin A
• UNII-313E9620QS
• HSDB 6745
• C20H35NO13
• D-CHIRO-INOSITOL, 1,5,6-TRIDEOXY-4-O-.BETA.-D-GLUCOPYRANOSYL-5-(HYDROXYMETHYL)-1-(((1S,4R,5S,6S)-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOHEXEN-1-YL)AMINO)-
• D-chiro-Inositol, 1,5,6-trideoxy-4-O-.beta.-D-glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-
• (+)-validamycin A
• Validamycin A (Standard)
• VALIDAMYCIN A [HSDB]
• orb1692160
• orb3024953
• SCHEMBL3121491
• CHEMBL1923413
• HY-B0856R
• JARYYMUOCXVXNK-CSLFJTBJSA-N
• HY-B0856
• AKOS016012982
• AG-F-30599
• AV59477
• VALIDAMYCINS VALIDAMYCIN A [MI]
• AC-32607
• AS-15281
• CS-0012869
• 248V478
• Validamycin A, PESTANAL(R), analytical standard
• Validamycin; CE30; JARYYMUOCXVXNK-CSLFJTBJSA-N
• D-Chiro-inositol,1,5,6-trideoxy-3-O-beta-D-glucopyranosyl-
• (1S-(1.ALPHA.,4.ALPHA.,5.BETA.,6.ALPHA.))-1,5,6-TRIDEOXY-4-O-.BETA.-D- GLUCOPYRANOSYL-5-(HYDROXYMETHYL)-1-((4,5,6-TRIHYDROXY-3- (HYDROXYMETHYL)-2-CYCLOHEXEN-1-YL)AMINO)-D-CHIRO-INOSITOL
• (1S-(1A,4A,5B,6A))-1,5,6-TRIDEOXY-3-O-B-D-GLUCOPYRANOSYL-5- (HYDROXYMETHYL)-1-((4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2- CYCLOHEXEN-1-YL)AMINO)-D-CHIRO-INOSITOL
• 1,5,6-trideoxy-4-O-beta-D-glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-D-chiro-inositol
• 1L-(1,3,4/2,6)-2,3-DIHYDROXY-6-HYDROMETHYL-4-((1S,4R,5S,6S)- 4,5,6-TRIHYDROXY-3-HYDROXYMETHYLCYCLOHEX-2- ENYLAMINO)CYCLOHEXYL .BETA.-D-GLUCOPYRANOSIDE
• 1L-(1,3,4/2,6)-2,3-DIHYDROXY-6-HYDROXYMETHYL-4- ((1S,4R,5S,6S)-4,5,6-TRIHYDROXY-3-HYDROXYMETHYLCYCLOHEX-2- ENYLAMINO)CYCLOHEXYL .BETA.-D-GLUCOPYRANOSIDE
• 58194-43-7
• D-1,5,6-TRIDEOXY-3-O-.BETA.-D-GLUCOPYRANOSYL-5- (HYDROXYMETHYL)-1-((4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2- CYCLOHEXEN-1-YL)AMINO)-D-CHIROINOSITOL
• D-CHIRO-INOSITOL, 1,5,6-TRIDEOXY-3-O-.BETA.-D-GLUCOPYRANOSYL- 5-(HYDROXYMETHYL)-1-((4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2- CYCLOHEXEN-1-YL)AMINO)-, (1S-(1-.ALPHA.,4-.ALPHA.,5-.BETA.,6- .ALPHA.))-
• D-CHIRO-INOSITOL, 1,5,6-TRIDEOXY-4-O-.BETA.-D-GLUCOPYRANOSYL-5-(HYDROXYMETHYL)-1-((4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOHEXEN-1-YL)AMINO)-, (1S-(1.ALPHA.,4.ALPHA.,5.BETA.,6.ALPHA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9144	91.44%
Caco-2	-	0.9180	91.80%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.9429	94.29%
Subcellular localzation	Lysosomes	0.3608	36.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8902	89.02%
OATP1B3 inhibitior	+	0.9452	94.52%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8832	88.32%
P-glycoprotein inhibitior	-	0.7730	77.30%
P-glycoprotein substrate	-	0.8045	80.45%
CYP3A4 substrate	+	0.5874	58.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7634	76.34%
CYP3A4 inhibition	-	0.9764	97.64%
CYP2C9 inhibition	-	0.8842	88.42%
CYP2C19 inhibition	-	0.8581	85.81%
CYP2D6 inhibition	-	0.8856	88.56%
CYP1A2 inhibition	-	0.8702	87.02%
CYP2C8 inhibition	-	0.6836	68.36%
CYP inhibitory promiscuity	-	0.8251	82.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6908	69.08%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9631	96.31%
Skin irritation	-	0.8012	80.12%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6647	66.47%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8842	88.42%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7269	72.69%
Acute Oral Toxicity (c)	IV	0.5170	51.70%
Estrogen receptor binding	+	0.5675	56.75%
Androgen receptor binding	+	0.5193	51.93%
Thyroid receptor binding	+	0.5838	58.38%
Glucocorticoid receptor binding	-	0.6518	65.18%
Aromatase binding	+	0.7000	70.00%
PPAR gamma	+	0.5395	53.95%
Honey bee toxicity	-	0.6881	68.81%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.8699	86.99%

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	98.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.34%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.03%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.90%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.37%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.18%	95.83%
CHEMBL4208	P20618	Proteasome component C5	84.99%	90.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.85%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.57%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.57%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 443629
• LOTUS: LTS0123861
• wikiData: Q7911668