Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2020-09-23 01:56:38 UTC
Updated at2021-08-10 02:55:17 UTC
NP-MRD IDNP0001565
Secondary Accession NumbersNone
Natural Product Identification
Common NameActinotetraose hexatiglate
Provided ByNPAtlasNPAtlas Logo
Description[(2R,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}-6-({[(2E)-2-methylbut-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydroxy-5-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}oxan-2-yl]methyl (2E)-2-methylbut-2-enoate belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. Actinotetraose hexatiglate is found in Amycolatopsis. It was first documented in 1998 (PMID: 10048568). Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}-6-({[(2E)-2-methylbut-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydroxy-5-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}oxan-2-yl]methyl (2E)-2-methylbut-2-enoate.
Structure
Data?1628564117
Synonyms
ValueSource
[(2R,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}-6-({[(2E)-2-methylbut-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydroxy-5-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}oxan-2-yl]methyl (2E)-2-methylbut-2-enoic acidGenerator
Actinotetraose hexatiglic acidGenerator
Chemical FormulaC54H78O27
Average Mass1159.1910 Da
Monoisotopic Mass1158.47305 Da
IUPAC Name[(2R,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}-6-({[(2E)-2-methylbut-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydroxy-5-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}oxan-2-yl]methyl (2E)-2-methylbut-2-enoate
Traditional Name[(2R,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}-6-({[(2E)-2-methylbut-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydroxy-5-{[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis({[(2E)-2-methylbut-2-enoyl]oxy})oxan-2-yl]oxy}oxan-2-yl]methyl (2E)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@@]2([H])[C@@]([H])(O[C@@]3([H])O[C@]([H])(C([H])([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@@]3([H])O[H])O[C@]([H])(C([H])([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@@]([H])(O[H])[C@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@]1([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H]
InChI Identifier
InChI=1S/C54H78O27/c1-13-23(7)45(63)69-21-31-33(57)35(59)43(79-51-37(61)41(77-49(67)27(11)17-5)39(29(19-55)71-51)75-47(65)25(9)15-3)53(73-31)81-54-44(36(60)34(58)32(74-54)22-70-46(64)24(8)14-2)80-52-38(62)42(78-50(68)28(12)18-6)40(30(20-56)72-52)76-48(66)26(10)16-4/h13-18,29-44,51-62H,19-22H2,1-12H3/b23-13+,24-14+,25-15+,26-16+,27-17+,28-18+/t29-,30-,31-,32-,33-,34-,35+,36+,37-,38-,39-,40-,41-,42-,43-,44-,51+,52+,53-,54-/m1/s1
InChI KeyBHAUYHDLIURVPC-ZNKXWPPQSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Amycolatopsis
Chemical Taxonomy
Description Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSaccharolipids
Sub ClassNot Available
Direct ParentSaccharolipids
Alternative Parents
Substituents
  • Oligosaccharide
  • Hexacarboxylic acid or derivatives
  • Saccharolipid
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acid ester
  • Fatty acyl
  • Oxane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10(2.6) g/LALOGPS
logP10(5.03) g/LChemAxon
logS10(-3.6) g/LALOGPS
pKa (Strongest Acidic)11.88ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area384.25 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity276.14 m³·mol⁻¹ChemAxon
Polarizability119.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA018382
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9019190
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10843896
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rickards RW, Rothschild JM, Lacey E: Structure of actinotetraose hexatiglate, a unique glucotetraose from an actinomycete bacterium. J Antibiot (Tokyo). 1998 Dec;51(12):1093-8. doi: 10.7164/antibiotics.51.1093. [PubMed:10048568 ]