MiMeDB: Showing metabocard for 1-Phosphatidyl-D-myo-inositol (MMDBc0032948)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:28:30 UTC

Update Date

2022-08-31 21:48:55 UTC

MiMeDB ID

MMDBc0032948

Metabolite Identification

Common Name

1-Phosphatidyl-D-myo-inositol

Description

Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231220562D          

 25 25  0  0  1  0            999 V2000
   14.9650  -10.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2505   -9.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2505   -9.0480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5361   -8.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8216   -9.0480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8216   -9.8730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5361  -10.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361  -11.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1071  -10.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1071   -8.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361   -7.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9650   -8.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2505   -7.3980    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.9650   -7.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361   -6.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9650   -6.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9650   -6.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6795   -5.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3918   -6.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1085   -5.7558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8207   -6.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5374   -5.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6818   -4.9230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3973   -4.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3996   -3.6874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 12  1  1  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  1  0  0  0
  6  7  1  0  0  0  0
  6  9  1  6  0  0  0
  7  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  2  0  0  0  0
 23 18  1  6  0  0  0
 24 23  1  0  0  0  0
 25 24  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032948

> <DATABASE_NAME>
MIME

> <SMILES>
OC1C(O)[C@H](O)C(OP(O)(=O)OCC(COC=O)OC=O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H19O13P/c12-3-21-1-5(22-4-13)2-23-25(19,20)24-11-9(17)7(15)6(14)8(16)10(11)18/h3-11,14-18H,1-2H2,(H,19,20)/t5?,6?,7-,8?,9+,10-,11?/m0/s1

> <INCHI_KEY>
GUBXYMKIJFOYOA-WSRCIYAPSA-N

> <FORMULA>
C11H19O13P

> <MOLECULAR_WEIGHT>
390.2345

> <EXACT_MASS>
390.056327206

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
32.846154765050215

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2,3-bis(formyloxy)propoxy]({[(2R,3S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-1.66

> <JCHEM_LOGP>
-4.063198509999999

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.360530531715526

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.833256856862767

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6458130204247565

> <JCHEM_POLAR_SURFACE_AREA>
209.50999999999996

> <JCHEM_REFRACTIVITY>
72.707

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.70e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-bis(formyloxy)propoxy[(2R,3S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      27.935 -19.200   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      26.601 -18.430   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.601 -16.890   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.267 -16.120   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.934 -16.890   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.934 -18.430   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.267 -19.200   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      25.267 -20.740   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      22.600 -19.200   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.600 -16.120   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      25.267 -14.580   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      27.935 -16.120   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0      26.601 -13.810   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      27.935 -14.580   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      25.267 -13.040   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      27.935 -13.040   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      27.935 -11.500   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.268 -10.730   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.598 -11.507   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      31.936 -10.744   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      33.265 -11.521   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      34.603 -10.758   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      29.273  -9.190   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      30.608  -8.423   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.613  -6.883   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7    9                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10    5                                                            
CONECT   11    4   13                                                       
CONECT   12    3                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

Synonyms

Value	Source
(3-Phosphatidyl)-1-D-inositol	HMDB
1,2-Diacyl-sn-glycero-3-phosphoinositol	HMDB
1-Phosphatidyl-1D-myo-inositol	HMDB
1-Phosphatidyl-myo-inositol	HMDB
Phosphatidyl-1D-myo-inositol	HMDB
Phosphatidylinositol	HMDB
Phosphoinositides	HMDB
Inositol phospholipids	HMDB
Phosphatidylinositols	HMDB
Phospholipids, inositide	HMDB
PtdIns	HMDB
Inositide phospholipids	HMDB
Inositol, phosphatidyl	HMDB
Phosphoglycerides, inositol	HMDB
Phospholipids, inositol	HMDB
Inositol phosphoglycerides	HMDB
Phosphatidyl inositol	HMDB

Chemical Formula

C₁₁H₁₉O₁₃P

Average Molecular Weight

390.2345

Monoisotopic Molecular Weight

390.056327206

IUPAC Name

[2,3-bis(formyloxy)propoxy]({[(2R,3S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

Traditional Name

2,3-bis(formyloxy)propoxy[(2R,3S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid

CAS Registry Number

Not Available

SMILES

OC1C(O)[C@H](O)C(OP(O)(=O)OCC(COC=O)OC=O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C11H19O13P/c12-3-21-1-5(22-4-13)2-23-25(19,20)24-11-9(17)7(15)6(14)8(16)10(11)18/h3-11,14-18H,1-2H2,(H,19,20)/t5?,6?,7-,8?,9+,10-,11?/m0/s1

InChI Key

GUBXYMKIJFOYOA-WSRCIYAPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylinositols. These are glycerophosphoinositols where the glycerol is esterified with two fatty acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositols

Direct Parent

Phosphatidylinositols

Alternative Parents

Substituents

Diacylglycerophosphoinositol
Inositol phosphate
Cyclohexanol
Dialkyl phosphate
Cyclitol or derivatives
Alkyl phosphate
Dicarboxylic acid or derivatives
Phosphoric acid ester
Organic phosphoric acid derivative
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	27 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-4.1	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	72.71 m³·mol⁻¹	ChemAxon
Polarizability	32.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-03y1-1352149000-d88efb76f7886b51159a	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-2429000000-eb25eae6f367048dab43	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001d-9786000000-ef9de9b6628c1ae3f1d0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000b-8900000000-b353f13d30710ab1440f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-3039000000-ebc2bd0d92a4b2183e67	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-9263000000-6deaf9eca5534628df3c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9110000000-46ead7f49d30ae57b126	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details
Animal	Milk	Bos taurus	FooDB	31437929	details
Animal	Milk	Bos taurus	FooDB	31437929	details
Plant	Leaves	Lactuca sativa	FooDB	31437929	details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0006953

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024159

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01194

BioCyc ID

1-PHOSPHATIDYL-MYO-INOSITOL

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477912

PDB ID

Not Available

ChEBI ID

16749

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for 1-Phosphatidyl-D-myo-inositol (MMDBc0032948)

MOL for #<Metabolite:0x00007f09201cf680>

3D MOL for #<Metabolite:0x00007f09201cf680>

3D SDF for #<Metabolite:0x00007f09201cf680>

3D-SDF for #<Metabolite:0x00007f09201cf680>

PDB for #<Metabolite:0x00007f09201cf680>

3D PDB for #<Metabolite:0x00007f09201cf680>

SMILES for #<Metabolite:0x00007f09201cf680>

INCHI for #<Metabolite:0x00007f09201cf680>

Structure for #<Metabolite:0x00007f09201cf680>

3D Structure for #<Metabolite:0x00007f09201cf680>