Cannabis Compound Database: Showing Compound Card for Mannitol (CDB006140)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References transporters (1) Show 3 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:21:29 UTC

Updated at

2020-12-07 19:06:54 UTC

CannabisDB ID

CDB006140

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Mannitol

Description

Mannitol, also known ashexan-1,2,3,4,5,6-hexol (C6H8(OH)6), osmitrol or tobrex, 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. Mannitol is one of the most abundant energy and carbon storage molecules in nature, and is produced by a plethora of organisms, including bacteria, fungi, algae, lichens, and many plants such as Cannabis (PMID:19578847 ). Mannitol is commonly used as a sweetener in diabetic foods as it is poorly absorbed by the intestines. Mannitol is also used as medication to decrease pressure in the eyes, (i.e. glaucoma) and to lower increased intracranial pressure. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. Mannitol can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function. Mannitol is commonly used as a research tool in cell biological studies, usually to control osmolarity. Chemically, mannitol as a sugar alcohol, is similar to xylitol or sorbitol and is considered an isomer of sorbitol. However, mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this reason, it is not uncommon to add a base to adjust its pH, such as sodium bicarbonate. Mannitol is a non-permeating molecule, meaning that it cannot cross biological membranes. Because of this inability to cross biological membranes, mannitol has been used for the determination of glomerular filtration rate (GFR). Altered levels of mannitol have been found to be associated with cytochrome c oxidase deficiency and ribose-5-phosphate isomerase deficiency, which are inborn errors of metabolism. Mannitol is also a microbial metabolite found in Aspergillus, Candida, Clostridium, Gluconobacter, Lactobacillus, Lactococcus, Leuconostoc, Pseudomonas, Rhodobacteraceae, Saccharomyces, Streptococcus, Torulaspora and Zymomonas (PMID: 15240312 ; PMID: 29480337 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexaol	ChEBI
(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol	ChEBI
D-(-)-Mannitol	ChEBI
Dulcite	ChEBI
e 421	ChEBI
e-421	ChEBI
e421	ChEBI
Manna sugar	ChEBI
Mannite	ChEBI
Osmitrol	ChEBI
D-Mannitol	Kegg
Tobrex	Kegg
Bronchitol	Kegg
1,2,3,4,5,6-Hexanehexol	HMDB
Cordycepate	HMDB
Cordycepic acid	HMDB
Diosmol	HMDB
Hexahydroxyhexane	HMDB
Hexanhexol	HMDB
Invenex	HMDB
Isotol	HMDB
Manicol	HMDB
Maniton S	HMDB
Maniton-S	HMDB
Mannazucker	HMDB
Mannidex	HMDB
Mannigen	HMDB
Mannistol	HMDB
Mannit	HMDB
Mannit p	HMDB
Mannogem 2080	HMDB
Marine crystal	HMDB
Mushroom sugar	HMDB
Osmofundin	HMDB
Osmosal	HMDB
Resectisol	HMDB
SDM No. 35	HMDB
(L)-Mannitol	HMDB
Mannitol	ChEBI

Chemical Formula

C₆H₁₄O₆

Average Molecular Weight

182.17

Monoisotopic Molecular Weight

182.079

IUPAC Name

(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol

Traditional Name

mannitol

CAS Registry Number

69-65-8

SMILES

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

InChI Identifier

InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1

InChI Key

FBPFZTCFMRRESA-KVTDHHQDSA-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

mannitol (CHEBI:16899 )

Ontology

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	166 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	216 mg/mL at 25 °C	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	-3.10	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-2.7	ALOGPS
logP	-3.7	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.4 m³·mol⁻¹	ChemAxon
Polarizability	17.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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)	splash10-00di-9000000000-d5db4fbf6c1eb9dd3564	2018-05-25	View Spectrum
GC-MS	Mannitol, 6 TMS, GC-MS Spectrum	splash10-0ktb-0931000000-b481d576c5f24dd1b1d5	Spectrum
GC-MS	Mannitol, non-derivatized, GC-MS Spectrum	splash10-066s-0942000000-20043a375d72ca08dce9	Spectrum
GC-MS	Mannitol, 6 TMS, GC-MS Spectrum	splash10-066r-1974000000-38a4beaca17ab8c750b6	Spectrum
GC-MS	Mannitol, non-derivatized, GC-MS Spectrum	splash10-0229-9100000000-5655e9df8e0fdcaa72a0	Spectrum
GC-MS	Mannitol, non-derivatized, GC-MS Spectrum	splash10-001i-9200000000-0dad802ab0000303cb33	Spectrum
GC-MS	Mannitol, non-derivatized, GC-MS Spectrum	splash10-0ktb-0931000000-b481d576c5f24dd1b1d5	Spectrum
GC-MS	Mannitol, non-derivatized, GC-MS Spectrum	splash10-066s-0942000000-20043a375d72ca08dce9	Spectrum
GC-MS	Mannitol, non-derivatized, GC-MS Spectrum	splash10-066r-1974000000-38a4beaca17ab8c750b6	Spectrum
GC-MS	Mannitol, non-derivatized, GC-MS Spectrum	splash10-066s-0942000000-f4df881aeebac32de5c7	Spectrum
Predicted GC-MS	Mannitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03k9-9500000000-97c5853d3e9b96f9d054	Spectrum
Predicted GC-MS	Mannitol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6s-7141193000-dcd9245e12314ee0ced4	Spectrum
Predicted GC-MS	Mannitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mannitol, TMS_3_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)	splash10-014j-9600000000-26f4335f7ef7c81ca261	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-066r-9000000000-73db1fbd51fb8c061bec	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05mo-9000000000-45a4dea1d21286c4b8da	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0089-6900000000-961d76d6550bc342ffa1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0089-6900000000-061f88989a6ac71321e3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0ik9-1900000000-eb8ea056f3b1dfe2fb1f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-1900000000-6768b4744e1a4e56b18b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00kb-1900000000-0765563624accf132d03	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00dr-0900000000-e159f4e76b7847313f35	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0900-0910000000-8d56394cbc78dd3b5ca0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0079-0900000000-63517bff4abfbf09e1ca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0w2l-0940000000-dc20c851073dcbc4dba9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-05ar-9500000000-c82bc4e2d1e173359c3e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-9000000000-47357f9a38864cba9668	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-066r-9000000000-9cd6979ccf800d067e03	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-02tj-9400000000-b72fa250b3caa4a87682	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9000000000-fc27b5c54b0dd6fc8a39	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9100000000-0436dafd7f39b7c910e9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-066u-9000000000-fb4a8654ee07a1dcc56c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-ef92b9091ecf5d15cdee	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-47f19bd4e51bff726536	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9100000000-60d5147d8e349337fe97	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-07ju-8900000000-36f0fe0f346a6424162a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0c0c-9200000000-36e85b5ec098a45204c3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9000000000-77703ee971336704163f	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, 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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Multidrug resistance protein 1	ABCB1	7q21.12	P08183	details

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000765

DrugBank ID

DB00742

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Mannitol

METLIN ID

142

PubChem Compound

6251

PDB ID

Not Available

ChEBI ID

16899

References

General References

Song SH, Vieille C: Recent advances in the biological production of mannitol. Appl Microbiol Biotechnol. 2009 Aug;84(1):55-62. doi: 10.1007/s00253-009-2086-5. Epub 2009 Jul 4. [PubMed:19578847 ]
Wisselink HW, Mars AE, van der Meer P, Eggink G, Hugenholtz J: Metabolic engineering of mannitol production in Lactococcus lactis: influence of overexpression of mannitol 1-phosphate dehydrogenase in different genetic backgrounds. Appl Environ Microbiol. 2004 Jul;70(7):4286-92. doi: 10.1128/AEM.70.7.4286-4292.2004. [PubMed:15240312 ]
Zhang M, Gu L, Cheng C, Ma J, Xin F, Liu J, Wu H, Jiang M: Recent advances in microbial production of mannitol: utilization of low-cost substrates, strain development and regulation strategies. World J Microbiol Biotechnol. 2018 Feb 26;34(3):41. doi: 10.1007/s11274-018-2425-8. [PubMed:29480337 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

Showing Compound Card for Mannitol (CDB006140)

Structure for CDB006140 (Mannitol)

Transporters