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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 19:01:21 UTC

Update Date

2023-02-21 17:24:02 UTC

HMDB ID

HMDB0034220

Secondary Accession Numbers

HMDB34220

Metabolite Identification

Common Name

Levoinositol

Description

Levoinositol (also known as 1L-chiro-Inositol or L-chiro-inositol, abbreviated LCI) is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol and cis-inositol. In humans, most inositol is synthesized in the kidneys, typically in amounts of a few grams per day. Levoinositol is found in dandelion and is widely distributed in higher plants predominantly as its monomethyl ether. Inositol is a cyclic polyalcohol that plays an important role as a second messenger in a cell, in the form of inositol phosphates. It is found in many foods, particularly in cereals with high bran content. It is an isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed., p1379) Inositol phospholipids are important in signal transduction.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 31-OCT-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-OCT-17         0                                  
HETATM    1  O   UNK     0       4.295  -8.033   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       1.628  -6.493   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.981  -6.506   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.981  -3.401   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.628  -3.413   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.295  -1.873   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.295  -6.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.965  -5.723   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.632  -5.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.632  -4.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.965  -4.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.295  -3.413   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5   11                                                            
CONECT    6   12                                                            
CONECT    7    1    8    9                                                  
CONECT    8    2    7   11                                                  
CONECT    9    3    7   10                                                  
CONECT   10    4    9   12                                                  
CONECT   11    5    8   12                                                  
CONECT   12    6   10   11                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Inositol	ChEBI
(1R,2R,3R,4R,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexol	ChEBI
1,2,4/3,5,6-cyclohexanehexol	ChEBI
L-Inositol	ChEBI

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

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

Traditional Name

L-chiro-inositol

CAS Registry Number

551-72-4

SMILES

O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m1/s1

InChI Key

CDAISMWEOUEBRE-SHFUYGGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

Alternative Parents

Substituents

Cyclohexanol
Sugar alcohol
Cyclitol or derivatives
Cyclic alcohol
Polyol
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

chiro-inositol (CHEBI:27374 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034220)
Cytoplasm (HMDB: HMDB0034220)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24740205)
Saliva (HMDB: HMDB0034220)

Excreta

Biofluid or Excreta

Feces (PMID: 20669995)
Urine (PMID: 27510537)

Dandelion (FooDB: FOOD00181)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	246 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	485 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.8	ChemAxon
logS	0.43	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3.6	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	0	ChemAxon
Refractivity	35.78 m³·mol⁻¹	ChemAxon
Polarizability	15.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	143.909	30932474
DeepCCS	[M-H]-	141.514	30932474
DeepCCS	[M-2H]-	176.118	30932474
DeepCCS	[M+Na]+	150.495	30932474
AllCCS	[M+H]+	142.3	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	129.5	32859911
AllCCS	[M+Na-2H]-	130.5	32859911
AllCCS	[M+HCOO]-	131.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levoinositol	O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O	3553.7	Standard polar	33892256
Levoinositol	O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O	2007.7	Standard non polar	33892256
Levoinositol	O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O	1920.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levoinositol,1TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O	1743.3	Semi standard non polar	33892256
Levoinositol,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@H]1O	1743.3	Semi standard non polar	33892256
Levoinositol,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	1743.3	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C	1708.2	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	1721.1	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1735.0	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O	1721.1	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #5	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1708.2	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O)[C@@H](O)[C@H]1O	1708.2	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #7	C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O	1735.0	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #8	C[Si](C)(C)O[C@H]1[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)[C@@H]1O	1721.1	Semi standard non polar	33892256
Levoinositol,2TMS,isomer #9	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	1708.2	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1686.0	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #10	C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C	1735.6	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1735.6	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O	1735.6	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)[C@@H]1O	1686.0	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #5	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	1780.1	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #6	C[Si](C)(C)O[C@H]1[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1735.6	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1735.6	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #8	C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1686.0	Semi standard non polar	33892256
Levoinositol,3TMS,isomer #9	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O	1735.6	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C	1804.7	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O	1858.6	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1804.7	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	1858.6	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #5	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	1854.5	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #6	C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1804.7	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #7	C[Si](C)(C)O[C@H]1[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1858.6	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #8	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	1804.7	Semi standard non polar	33892256
Levoinositol,4TMS,isomer #9	C[Si](C)(C)O[C@H]1[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1854.5	Semi standard non polar	33892256
Levoinositol,5TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1934.2	Semi standard non polar	33892256
Levoinositol,5TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1934.2	Semi standard non polar	33892256
Levoinositol,5TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1934.2	Semi standard non polar	33892256
Levoinositol,6TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2009.2	Semi standard non polar	33892256
Levoinositol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O	2020.4	Semi standard non polar	33892256
Levoinositol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@H]1O	2020.4	Semi standard non polar	33892256
Levoinositol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	2020.4	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2193.7	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2206.2	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2236.9	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2206.2	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2193.7	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@@H](O)[C@H]1O	2193.7	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O	2236.9	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)[C@@H]1O	2206.2	Semi standard non polar	33892256
Levoinositol,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	2193.7	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2456.9	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2490.3	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2490.3	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2490.3	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)[C@@H]1O	2456.9	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2511.9	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2490.3	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2490.3	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2456.9	Semi standard non polar	33892256
Levoinositol,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	2490.3	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2713.4	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2733.1	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2713.4	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2733.1	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2735.3	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2713.4	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2733.1	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2713.4	Semi standard non polar	33892256
Levoinositol,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2735.3	Semi standard non polar	33892256
Levoinositol,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2931.4	Semi standard non polar	33892256
Levoinositol,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2931.4	Semi standard non polar	33892256
Levoinositol,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2931.4	Semi standard non polar	33892256
Levoinositol,6TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3172.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Levoinositol GC-MS (Non-derivatized)	splash10-014i-0359000000-cec32f7b73a366b3f067	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levoinositol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dr-9700000000-6cc8567e1b238f96f926	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levoinositol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 10V, Positive-QTOF	splash10-001i-0900000000-5cb39f92646251665ebf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 20V, Positive-QTOF	splash10-001i-0900000000-2aeb7708f31c772e2d95	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 40V, Positive-QTOF	splash10-08gi-8900000000-74f89711a1c6891808a4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 10V, Negative-QTOF	splash10-004i-0900000000-8b68ff47f846a8ca1ddd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 20V, Negative-QTOF	splash10-004i-1900000000-03ef8572289795275d9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 40V, Negative-QTOF	splash10-0570-9300000000-950a37bd331028801e9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 10V, Negative-QTOF	splash10-004i-0900000000-c98742ed2c27fed8805b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 20V, Negative-QTOF	splash10-0570-9700000000-4e8df481dc1f1c124743	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 40V, Negative-QTOF	splash10-0a4i-9000000000-ea5996664694b27554a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 10V, Positive-QTOF	splash10-001i-0900000000-a3b1806f4d2d4bc9e470	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 20V, Positive-QTOF	splash10-03e9-9500000000-40e1f34ad1ad2b894cd9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoinositol 40V, Positive-QTOF	splash10-03dl-9000000000-5d72027b1e4acffd4c29	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

266600 (Crohn's disease)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001138

KNApSAcK ID

Not Available

Chemspider ID

10199754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27374

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Dai X, Zhang L, Hong T: Host cellular signaling induced by influenza virus. Sci China Life Sci. 2011 Jan;54(1):68-74. doi: 10.1007/s11427-010-4116-z. Epub 2011 Jan 21. [PubMed:21253874 ]
Cadman ED, Naugles DD, Lee CM: cAMP is not involved in interleukin-1-induced interleukin-6 release from human astrocytoma cells. Neurosci Lett. 1994 Sep 12;178(2):251-4. [PubMed:7529912 ]
Chen G, Kirby M, Zeng W, Young NS, Maciejewski JP: Superior growth of glycophosphatidy linositol-anchored protein-deficient progenitor cells in vitro is due to the higher apoptotic rate of progenitors with normal phenotype in vivo. Exp Hematol. 2002 Jul;30(7):774-82. [PubMed:12135676 ]
Kim CH, Park YS, Chung KN, Elwood PC: Sorting of the human folate receptor in MDCK cells. J Biochem Mol Biol. 2004 May 31;37(3):362-9. [PubMed:15469720 ]
Butlen D, Bernard C, Ammar A, Ferrary E: Purine and pyrimidine nucleotide-sensitive phosphoinositidase C in ampulla from frog semicircular canal. Am J Physiol. 1997 Jan;272(1 Pt 2):R51-8. [PubMed:9038990 ]
Pak Y, Huang LC, Lilley KJ, Larner J: In vivo conversion of [3H]myoinositol to [3H]chiroinositol in rat tissues. J Biol Chem. 1992 Aug 25;267(24):16904-10. [PubMed:1387397 ]
Matsumoto T, Kawanobe Y, Morita K, Ogata E: Effect of 1,25-dihydroxyvitamin D3 on phospholipid metabolism in a clonal osteoblast-like rat osteogenic sarcoma cell line. J Biol Chem. 1985 Nov 5;260(25):13704-9. [PubMed:2997179 ]
Takeuchi K, Shibamoto S, Nagamine K, Shigemori I, Omura S, Kitamura N, Ito F: Signaling pathways leading to transcription and translation cooperatively regulate the transient increase in expression of c-Fos protein. J Biol Chem. 2001 Jul 13;276(28):26077-83. Epub 2001 May 14. [PubMed:11352916 ]
Bates SH, Jones RB, Bailey CJ: Insulin-like effect of pinitol. Br J Pharmacol. 2000 Aug;130(8):1944-8. [PubMed:10952686 ]
Warita H, Manabe Y, Murakami T, Shiro Y, Nagano I, Abe K: Early decrease of survival signal-related proteins in spinal motor neurons of presymptomatic transgenic mice with a mutant SOD1 gene. Apoptosis. 2001 Oct;6(5):345-52. [PubMed:11483858 ]
Pampillo M, Camuso N, Taylor JE, Szereszewski JM, Ahow MR, Zajac M, Millar RP, Bhattacharya M, Babwah AV: Regulation of GPR54 signaling by GRK2 and {beta}-arrestin. Mol Endocrinol. 2009 Dec;23(12):2060-74. doi: 10.1210/me.2009-0013. Epub 2009 Oct 21. [PubMed:19846537 ]
Anzai-Takeda Y, Takeda Y, Sendo F, Araki Y: Inhibition of cell spreading in CHO cells transfected with cDNA of a glycosylphosphatidyl inositol-anchored protein, GPI-80. Immunobiology. 2005;210(1):1-10. [PubMed:16076029 ]
Pak Y, Larner J: Identification and characterization of chiroinositol-containing phospholipids from bovine liver. Biochem Biophys Res Commun. 1992 Apr 30;184(2):1042-7. [PubMed:1575723 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Levoinositol (HMDB0034220)

MOL for HMDB0034220 (Levoinositol)

3D MOL for HMDB0034220 (Levoinositol)

3D SDF for HMDB0034220 (Levoinositol)

3D-SDF for HMDB0034220 (Levoinositol)

PDB for HMDB0034220 (Levoinositol)

3D PDB for HMDB0034220 (Levoinositol)

SMILES for HMDB0034220 (Levoinositol)

INCHI for HMDB0034220 (Levoinositol)

Structure for HMDB0034220 (Levoinositol)

3D Structure for HMDB0034220 (Levoinositol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra