Cannabis Compound Database: Showing Compound Card for D-arabitol (CDB000142)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:26:21 UTC

Updated at

2020-11-18 16:34:50 UTC

CannabisDB ID

CDB000142

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

D-arabitol

Description

D-Arabitol or D-arabinitol, also known as klinit or lyxitol, belongs to the class of organic compounds known as sugar alcohols, a type of polyols. These are hydrogenated forms of carbohydrates in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. A polyol is an organic compound containing many hydroxyls. D-Arabitol is neutral compound. D-Arabitol is one of the sugar alcohols and cyclitols found in cannabis plant (PMID: 6991645 ). Polyols, classified by the number of carbon atoms and include the sugar alcohols, are linked to the pentose phosphate pathway (PPP). The PPP generates¬†NADPH¬†and¬†pentoses¬†(5-carbon¬†sugars) as well as¬†ribose 5-phosphate, a precursor for the synthesis of¬†nucleotides. While the pentose phosphate pathway oxidizes¬†glucose, its primary role is¬†anabolic¬†rather than¬†catabolic. Polyols, including D-arabitol, accumulates in body fluids in individuals with two defects in PPP, involving the enzymes ribose-5-phosphate isomerase (RPI) and transaldolase (PMID: 18987987 ). A patient with leukoencephalopathy and peripheral neuropathy, with a strong brain-CSF-plasma gradient of C5 polyols such as D-arabitol, was identified as suffering from RPI deficiency. Another patient displaying mainly liver problems and increased concentrations of polyols, mainly D-arabitol, was diagnosed with transaldolase deficiency. However, the mechanism of pathophysiology of polyols in patients with defects in the PPP is poorly understood. It is thought that D-arabitol is a metabolic end-product in humans. The mechanisms of brain and neuronal damage in RPI deficiency may result from polyol accumulation, causing secondary brain dysfunction (PMID: 16435225 ). D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the pentose and glucuronate interconversion pathway. D-Arabitol accumulated in a Penicillium rubens strain deleted of four highly expressed biosynthetic gene clusters that produce penicillin, roquefortine, chrysogine and fungisporin. The transcriptome of the P. rubens strain had changed when the gene cluster was removed, resulting in increased expression of D-arabinitol 4-dehydrogenase (PMID: 32376967 ). D-Arabitol, a fungal metabolite, is used as a marker for invasive candidiasis or infection by Candida fungal species (PMID: 15183861 ; PMID: 10647119 ). It is also a metabolite of Debaryomyces, Pichia and Zygosaccharomyces (PMID: 25809659 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-Arabinol	ChEBI
D-Lyxitol	ChEBI
D-Arabinitol	Kegg
Arabitol, (D)-isomer	HMDB
Arabitol	HMDB
D-(+)-Arabitol	HMDB
(+--)-Arabitol	HMDB
DL-Arabitol	HMDB
Arabino-pentitol	HMDB
Lyxitol	HMDB
D-Arabitol	ChEBI

Chemical Formula

C₅H₁₂O₅

Average Molecular Weight

152.15

Monoisotopic Molecular Weight

152.0685

IUPAC Name

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

Traditional Name

arabitol

CAS Registry Number

488-81-3

SMILES

OC[C@H](O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-

InChI Key

HEBKCHPVOIAQTA-ZXFHETKHSA-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

arabinitol (CHEBI:18333 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	102 - 105 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	936 mg/mL	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	14.28 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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-01vo-9000000000-f065454e8412613f8ecd	2018-05-25	View Spectrum
GC-MS	, 5 TMS, GC-MS Spectrum	splash10-0gb9-0982000000-4e5007f03273cea8b23e	Spectrum
Predicted GC-MS	, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_4_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_4_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_4_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TMS_5_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_2_1, 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)	splash10-01ba-9500000000-67233150807800e941f0	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01b9-9000000000-1ff17a8b87bbab9a3622	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-044i-9000000000-e0e330c8a899be718f60	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00m0-2900000000-c6b1101b88fa522fabd0	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0zmr-9500000000-164d598431954fc1aeae	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0uki-9600000000-b90e9cee04cd0631b599	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00e9-2900000000-75413a29e8c6b3d9a6a1	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0900000000-c5cc931b9156365c4ca7	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a5a-0900000000-94cf956e3f47a633d572	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03k9-0900000000-f0634d5b1d1f523b3caa	2018-05-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00do-9000000000-564c4ccf05ac119a3ac2	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-4f856d537cc8252ecc47	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-403bacad5117a30582df	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-eb879b27e7b182cfe7c0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udu-9400000000-3db6454ab3e2315aa744	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0btl-9200000000-b84c400427c7e44eb4dd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-c37624fb31a8cb33b163	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-d02566d106f64f56452d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-94760e1883352d4864b5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-a22bb5556fa857db4c5c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zmr-9500000000-1887747b16d168b09609	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-83f8fb1c321a951b0e7e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-ad178d7c96ba63131c18	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Transaldolase	TALDO1	11p15.5-p15.4	P37837	details
Ribose-5-phosphate isomerase	RPIA	2p11.2	P49247	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000568

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

D-arabinitol

METLIN ID

5551

PubChem Compound

94154

PDB ID

Not Available

ChEBI ID

18333

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Pohl C, Polli F, Schutze T, Viggiano A, Mozsik L, Jung S, de Vries M, Bovenberg RAL, Meyer V, Driessen AJM: A Penicillium rubens platform strain for secondary metabolite production. Sci Rep. 2020 May 6;10(1):7630. doi: 10.1038/s41598-020-64893-6. [PubMed:32376967 ]
Wamelink MM, Struys EA, Jakobs C: The biochemistry, metabolism and inherited defects of the pentose phosphate pathway: a review. J Inherit Metab Dis. 2008 Dec;31(6):703-17. doi: 10.1007/s10545-008-1015-6. Epub 2008 Nov 8. [PubMed:18987987 ]
Klusmann A, Fleischer W, Waldhaus A, Siebler M, Mayatepek E: Influence of D-arabitol and ribitol on neuronal network activity. J Inherit Metab Dis. 2005;28(6):1181-3. doi: 10.1007/s10545-005-0073-2. [PubMed:16435225 ]
Hui M, Cheung SW, Chin ML, Chu KC, Chan RC, Cheng AF: Development and application of a rapid diagnostic method for invasive Candidiasis by the detection of D-/L-arabinitol using gas chromatography/mass spectrometry. Diagn Microbiol Infect Dis. 2004 Jun;49(2):117-23. doi: 10.1016/j.diagmicrobio.2004.02.006. [PubMed:15183861 ]
Christensson B, Sigmundsdottir G, Larsson L: D-arabinitol--a marker for invasive candidiasis. Med Mycol. 1999 Dec;37(6):391-6. doi: 10.1046/j.1365-280x.1999.00249.x. [PubMed:10647119 ]
Kordowska-Wiater M: Production of arabitol by yeasts: current status and future prospects. J Appl Microbiol. 2015 Aug;119(2):303-14. doi: 10.1111/jam.12807. Epub 2015 Apr 8. [PubMed:25809659 ]

Enzymes

Enzyme Details

1. Transaldolase

General function:: Involved in catalytic activity
Specific function:: Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
Gene Name:: TALDO1
Uniprot ID:: P37837
Molecular weight:: 37539.74

Enzyme Details

2. Ribose-5-phosphate isomerase

General function:: Involved in ribose-5-phosphate isomerase activity
Specific function:: Not Available
Gene Name:: RPIA
Uniprot ID:: P49247
Molecular weight:: 33268.72

Showing Compound Card for D-arabitol (CDB000142)

Structure for CDB000142 (D-arabitol)

Enzymes