Cannabis Compound Database: Showing Compound Card for Ribitol (CDB006169)

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Record Information

Version

1.0

Created at

2020-03-18 23:22:22 UTC

Updated at

2020-12-07 19:06:58 UTC

CannabisDB ID

CDB006169

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Ribitol

Description

Ribitol, 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‚Äôs 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3S,4S)-Pentane-1,2,3,4,5-pentol	ChEBI
Adonitol	ChEBI
D-Adonitol	ChEBI
D-Ribitol	ChEBI
L-Ribitol	ChEBI
1,2,3,4,5-Pentanepentol	HMDB
Adonit	HMDB
Adonite	HMDB
Pentitol	HMDB

Chemical Formula

C₁₀H₁₈

Average Molecular Weight

138.25

Monoisotopic Molecular Weight

138.1409

IUPAC Name

(2R,3s,4S)-pentane-1,2,3,4,5-pentol

Traditional Name

ribitol

CAS Registry Number

87-99-0

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 Key

MZPDTOMKQCMETI-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Monosaccharide
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ribitol (CHEBI:15963 )

Ontology

Role

Industrial application:

Household products:

Antimicrobial agent:

Antibacterial

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	102 °C	Wikipedia
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.5	ALOGPS
logP	-3.1	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	32.44 m³·mol⁻¹	ChemAxon
Polarizability	14.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	D-arabitol, 5 TMS, GC-MS Spectrum	splash10-0fr2-0930000000-5a1a8471040df361537c	Spectrum
GC-MS	D-arabitol, non-derivatized, GC-MS Spectrum	splash10-0gba-0940000000-39c5ee90545f38856669	Spectrum
GC-MS	D-arabitol, 5 TMS, GC-MS Spectrum	splash10-00di-8941000000-a1eac40beaba679b545b	Spectrum
GC-MS	D-arabitol, 5 TMS, GC-MS Spectrum	splash10-00di-8930000000-85527d43cd5f10f959a8	Spectrum
GC-MS	D-arabitol, 5 TMS, GC-MS Spectrum	splash10-0gb9-0962000000-9c177252fb79fd04ff8c	Spectrum
GC-MS	D-arabitol, non-derivatized, GC-MS Spectrum	splash10-0fr2-0930000000-5a1a8471040df361537c	Spectrum
GC-MS	D-arabitol, non-derivatized, GC-MS Spectrum	splash10-0gba-0940000000-39c5ee90545f38856669	Spectrum
GC-MS	D-arabitol, non-derivatized, GC-MS Spectrum	splash10-00di-8941000000-a1eac40beaba679b545b	Spectrum
GC-MS	D-arabitol, non-derivatized, GC-MS Spectrum	splash10-00di-8930000000-85527d43cd5f10f959a8	Spectrum
GC-MS	D-arabitol, non-derivatized, GC-MS Spectrum	splash10-0gb9-0962000000-9c177252fb79fd04ff8c	Spectrum
Predicted GC-MS	D-arabitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dl-9100000000-738016d8bd07caed9ccc	Spectrum
Predicted GC-MS	D-arabitol, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-6033900000-a5ac27dc62580d112ccd	Spectrum
Predicted GC-MS	D-arabitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-arabitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00kb-9200000000-1c9444c33ee213e4aa4f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05mo-9000000000-baf46067df2ebf3b854c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-3276d3005611fd3d415c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0901000000-7db5e452cb762f33fd3a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014j-8900000000-5ee7c2252ae88c5c0198	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-47c7512c4671bb121a01	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-1900000000-b984613919de5add093c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0ufr-0901000000-616311fa40559ac618da	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014j-7900000000-c947bd6b615b2019d255	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-c7e6bce3675a8cd1566b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-419f37e184ec82e4c123	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014j-8900000000-e69cc8758936cd2cbcea	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-d6447ee4c80f85c44fef	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-1900000000-67203d89ca337c3cd9d1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014j-7900000000-867bbfc363a4790dadc1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-c7e6bce3675a8cd1566b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0900000000-419f37e184ec82e4c123	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-fd63152f503ab1d4aa19	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-d230735907e604c9d45a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-91a543c0d92a8d8d3c3d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udu-9300000000-e06ed1bf8e262afac25a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0btl-9100000000-b459e90a751cabc2a231	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9000000000-4943c8a982ad5101e46f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zmr-9500000000-1887747b16d168b09609	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-83f8fb1c321a951b0e7e	2021-09-21	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000508

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15963

References

General References

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 ]

Showing Compound Card for Ribitol (CDB006169)

Structure for CDB006169 (Ribitol)