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Record Information
Version2.0
Created at2021-01-06 07:30:58 UTC
Updated at2021-07-15 17:38:41 UTC
NP-MRD IDNP0022308
Secondary Accession NumbersNone
Natural Product Identification
Common NameCalditol
Provided ByNPAtlasNPAtlas Logo
Description Calditol is found in Sulfolobus sp. Calditol was first documented in 1995 (PMID: 7609602). Based on a literature review very few articles have been published on 5-(2,3-dihydroxypropoxy)-1-(hydroxymethyl)cyclopentane-1,2,3,4-tetrol (PMID: 18339312) (PMID: 30518563) (PMID: 28214513).
Structure
Data?1624507067
SynonymsNot Available
Chemical FormulaC9H18O8
Average Mass254.2350 Da
Monoisotopic Mass254.10017 Da
IUPAC Name(1S,2S,3S,4R,5R)-5-[(2R)-2,3-dihydroxypropoxy]-1-(hydroxymethyl)cyclopentane-1,2,3,4-tetrol
Traditional Name(1S,2S,3S,4R,5R)-5-[(2R)-2,3-dihydroxypropoxy]-1-(hydroxymethyl)cyclopentane-1,2,3,4-tetrol
CAS Registry NumberNot Available
SMILES
OCC(O)COC1C(O)C(O)C(O)C1(O)CO
InChI Identifier
InChI=1S/C9H18O8/c10-1-4(12)2-17-8-6(14)5(13)7(15)9(8,16)3-11/h4-8,10-16H,1-3H2
InChI KeyJOKFCZVUUMLXSM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sulfolobus sp.NPAtlas
Chemical Taxonomy
ClassificationNot classified
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
logP-2.7ALOGPS
logP-4.6ChemAxon
logS0.33ALOGPS
pKa (Strongest Acidic)11.88ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area150.84 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53 m³·mol⁻¹ChemAxon
Polarizability23.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA013219
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78444840
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101918438
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bode ML, Buddoo SR, Minnaar SH, du Plessis CA: Extraction, isolation and NMR data of the tetraether lipid calditoglycerocaldarchaeol (GDNT) from Sulfolobus metallicus harvested from a bioleaching reactor. Chem Phys Lipids. 2008 Aug;154(2):94-104. doi: 10.1016/j.chemphyslip.2008.02.005. Epub 2008 Mar 11. [PubMed:18339312 ]
  2. Sugai A, Sakuma R, Fukuda I, Kurosawa N, Itoh YH, Kon K, Ando S, Itoh T: The structure of the core polyol of the ether lipids from Sulfolobus acidocaldarius. Lipids. 1995 Apr;30(4):339-44. doi: 10.1007/BF02536042. [PubMed:7609602 ]
  3. Zeng Z, Liu XL, Wei JH, Summons RE, Welander PV: Calditol-linked membrane lipids are required for acid tolerance in Sulfolobus acidocaldarius. Proc Natl Acad Sci U S A. 2018 Dec 18;115(51):12932-12937. doi: 10.1073/pnas.1814048115. Epub 2018 Dec 5. [PubMed:30518563 ]
  4. Huguet C, Fietz S, Rosell-Mele A, Daura X, Costenaro L: Molecular dynamics simulation study of the effect of glycerol dialkyl glycerol tetraether hydroxylation on membrane thermostability. Biochim Biophys Acta Biomembr. 2017 May;1859(5):966-974. doi: 10.1016/j.bbamem.2017.02.009. Epub 2017 Feb 16. [PubMed:28214513 ]