Showing Compound Card for Ribitol (CDB006169)

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Record Information
Version1.0
Created at2020-03-18 23:22:22 UTC
Updated at2020-12-07 19:06:58 UTC
CannabisDB IDCDB006169
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameRibitol
DescriptionRibitol, also known as adonitol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Ribitol is formed by the reduction of the 5-carbon sugar ribose. Ribitol occurs naturally in some plants such as the pheasant’s eye (Adonis vernalis) and in the cell walls of some Gram-positive bacteria (in the form of ribitol phosphate). In humans, ribitol is a metabolic end product formed by the reduction of ribose in human fibroblasts and erythrocytes (pentitol, sugar alcohol, polyol). Industrially, tibitol can be used as a cryopreservative and has a strong protective effect on lactic acid bacteria during freeze-drying. Ribitol has been reported as one of the sugar alcohols present in cannabis plants (PMID: 4688907 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3S,4S)-Pentane-1,2,3,4,5-pentolChEBI
AdonitolChEBI
D-AdonitolChEBI
D-RibitolChEBI
L-RibitolChEBI
1,2,3,4,5-PentanepentolHMDB
AdonitHMDB
AdoniteHMDB
PentitolHMDB
Chemical FormulaC10H18
Average Molecular Weight138.25
Monoisotopic Molecular Weight138.1409
IUPAC Name(2R,3s,4S)-pentane-1,2,3,4,5-pentol
Traditional Nameribitol
CAS Registry Number87-99-0
SMILES
CC=C(C)CCC=C(C)C
InChI Identifier
InChI=1S/C10H18/c1-5-10(4)8-6-7-9(2)3/h5,7H,6,8H2,1-4H3
InChI KeyMZPDTOMKQCMETI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point102 °CWikipedia
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.5ALOGPS
logP-3.1ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability14.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSD-arabitol, 5 TMS, GC-MS Spectrumsplash10-0fr2-0930000000-5a1a8471040df361537cSpectrum
GC-MSD-arabitol, non-derivatized, GC-MS Spectrumsplash10-0gba-0940000000-39c5ee90545f38856669Spectrum
GC-MSD-arabitol, 5 TMS, GC-MS Spectrumsplash10-00di-8941000000-a1eac40beaba679b545bSpectrum
GC-MSD-arabitol, 5 TMS, GC-MS Spectrumsplash10-00di-8930000000-85527d43cd5f10f959a8Spectrum
GC-MSD-arabitol, 5 TMS, GC-MS Spectrumsplash10-0gb9-0962000000-9c177252fb79fd04ff8cSpectrum
GC-MSD-arabitol, non-derivatized, GC-MS Spectrumsplash10-0fr2-0930000000-5a1a8471040df361537cSpectrum
GC-MSD-arabitol, non-derivatized, GC-MS Spectrumsplash10-0gba-0940000000-39c5ee90545f38856669Spectrum
GC-MSD-arabitol, non-derivatized, GC-MS Spectrumsplash10-00di-8941000000-a1eac40beaba679b545bSpectrum
GC-MSD-arabitol, non-derivatized, GC-MS Spectrumsplash10-00di-8930000000-85527d43cd5f10f959a8Spectrum
GC-MSD-arabitol, non-derivatized, GC-MS Spectrumsplash10-0gb9-0962000000-9c177252fb79fd04ff8cSpectrum
Predicted GC-MSD-arabitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-9100000000-738016d8bd07caed9cccSpectrum
Predicted GC-MSD-arabitol, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6033900000-a5ac27dc62580d112ccdSpectrum
Predicted GC-MSD-arabitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-arabitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kb-9200000000-1c9444c33ee213e4aa4f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05mo-9000000000-baf46067df2ebf3b854c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-3276d3005611fd3d415c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0901000000-7db5e452cb762f33fd3a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-8900000000-5ee7c2252ae88c5c01982012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-47c7512c4671bb121a012012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-1900000000-b984613919de5add093c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0ufr-0901000000-616311fa40559ac618da2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-7900000000-c947bd6b615b2019d2552012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-c7e6bce3675a8cd1566b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-419f37e184ec82e4c1232012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-8900000000-e69cc8758936cd2cbcea2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-d6447ee4c80f85c44fef2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1900000000-67203d89ca337c3cd9d12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-7900000000-867bbfc363a4790dadc12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c7e6bce3675a8cd1566b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-419f37e184ec82e4c1232017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-fd63152f503ab1d4aa192017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-d230735907e604c9d45a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-91a543c0d92a8d8d3c3d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9300000000-e06ed1bf8e262afac25a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9100000000-b459e90a751cabc2a2312017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-4943c8a982ad5101e46f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zmr-9500000000-1887747b16d168b096092021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-83f8fb1c321a951b0e7e2021-09-21View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000508
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022083
KNApSAcK IDC00001171
Chemspider ID10254628
KEGG Compound IDC00474
BioCyc IDRIBITOL
BiGG ID35086
Wikipedia LinkRibitol
METLIN ID316
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15963
References
General References
  1. Groce JW, Jones LA: Carbohydrate and cyclitol content of cannabis. J Agric Food Chem. 1973 Mar-Apr;21(2):211-4. doi: 10.1021/jf60186a003. [PubMed:4688907 ]