MiMeDB: Showing metabocard for 1-phosphatidyl-1D-myo-inositol 4-phosphate (MMDBc0047840)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:45:20 UTC

Update Date

2022-09-01 01:59:38 UTC

Metabolite ID

MMDBc0047840

Metabolite Identification

Common Name

1-phosphatidyl-1D-myo-inositol 4-phosphate

Description

1-phosphatidyl-1D-myo-inositol 4-phosphate belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety. Phosphatidylinositol-4-phosphate (PtdIns4P, PI-4-P, PI4P, or PIP) is a precursor of phosphatidylinositol (4,5)-bisphosphate. 1-phosphatidyl-1D-myo-inositol 4-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, 1-phosphatidyl-1D-myo-inositol 4-phosphate is involved in mercaptopurine metabolism pathway. In the Golgi apparatus, PtdIns4P binds to the GTP-binding protein ARF and to effector proteins, including four-phosphate-adaptor protein 1 and 2 (FAPP1 and FAPP2). This three molecule complex recruits proteins that need to be carried to the cell membrane. There is now evidence that PI-4-P is capable of deforming lipid systems into tightly curved assemblies, this is consistent with similar behaviour observed in phosphatidylinositol. PtdIns4P is prevalent in the membrane of the Golgi apparatus.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10031311002D          

 25 25  0  0  0  0            999 V2000
   -0.9601    0.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2674   -0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3802    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160    1.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0023    0.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1313   -0.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9170    1.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3226    1.9261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592   -1.2450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.4001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7512    1.0216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4066    2.6304    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.0348    2.1617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795    3.2164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9489    3.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0229    4.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774    4.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687    5.1868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    5.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034    6.4142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020    5.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0448    5.4385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7347    4.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4775    5.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  2 10  1  0  0  0  0
  1 11  1  0  0  0  0
  6 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047840

> <DATABASE_NAME>
MIME

> <SMILES>
OC1C(O)C(O)C(OP(O)(=O)OCCOC(=O)COC=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H19O13P/c12-4-21-3-5(13)22-1-2-23-25(19,20)24-11-9(17)7(15)6(14)8(16)10(11)18/h4,6-11,14-18H,1-3H2,(H,19,20)

> <INCHI_KEY>
YDHAXCHJTOHGPB-UHFFFAOYSA-N

> <FORMULA>
C11H19O13P

> <MOLECULAR_WEIGHT>
390.2345

> <EXACT_MASS>
390.056327206

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
33.251093012724226

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[2-(formyloxy)acetyl]oxy}ethoxy)[(2,3,4,5,6-pentahydroxycyclohexyl)oxy]phosphinic acid

> <ALOGPS_LOGP>
-1.89

> <JCHEM_LOGP>
-4.201412906

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.360530532250554

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8368013046311256

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6458130204247503

> <JCHEM_POLAR_SURFACE_AREA>
209.50999999999996

> <JCHEM_REFRACTIVITY>
72.9372

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[2-(formyloxy)acetyl]oxy}ethoxy(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-OCT-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-OCT-13         0                                  
HETATM    1  C   UNK     0      -1.792   0.043   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.499  -0.777   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.710   0.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.634   1.403   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.590   2.159   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.871   1.244   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.112  -0.524   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.712   2.435   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.602   3.595   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.484  -2.324   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.123  -0.747   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.269   1.907   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0       0.759   4.910   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0       1.932   4.035   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.335   6.004   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.771   6.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.909   7.502   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.318   8.142   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.302   9.682   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.876  10.323   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.860  11.973   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.164   9.465   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.550  10.152   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.838   9.295   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.225   9.981   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1   12                                                  
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    5   13                                                       
CONECT   10    2                                                            
CONECT   11    1                                                            
CONECT   12    6                                                            
CONECT   13    9   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   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
1-Phosphatidyl-1D-myo-inositol 4-phosphoric acid	Generator

Molecular Formula

C₁₁H₁₉O₁₃P

Average Mass

390.2345

Monoisotopic Mass

390.056327206

IUPAC Name

(2-{[2-(formyloxy)acetyl]oxy}ethoxy)[(2,3,4,5,6-pentahydroxycyclohexyl)oxy]phosphinic acid

Traditional Name

2-{[2-(formyloxy)acetyl]oxy}ethoxy(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphinic acid

CAS Registry Number

Not Available

SMILES

OC1C(O)C(O)C(OP(O)(=O)OCCOC(=O)COC=O)C(O)C1O

InChI Identifier

InChI=1S/C11H19O13P/c12-4-21-3-5(13)22-1-2-23-25(19,20)24-11-9(17)7(15)6(14)8(16)10(11)18/h4,6-11,14-18H,1-3H2,(H,19,20)

InChI Key

YDHAXCHJTOHGPB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Inositol phosphates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	25 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-4.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.84	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	72.94 m³·mol⁻¹	ChemAxon
Polarizability	33.25 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 (Non-derivatized) - 70eV, Positive	splash10-01w1-9376000000-2233d1f51ef132d8c0c7	2017-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01p5-6879000000-904a77ecf0da5cf04f4f	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rm-6493000000-558a925ca37b04d01239	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9700000000-b6a8b8f1924d97b52ef6	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uel-7549000000-a805f2a1f1f1c18486de	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-054o-9342000000-214f716f80b679b4bf12	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9110000000-745aa369b663eb9938f4	2016-09-14	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001944	Phosphatidylinositol 4,5-bisphosphate	1-phosphatidyl-1D-myo-inositol 4-phosphate	inositol polyphosphate-5-phosphatase, 75kDa	VMH	10764818 12915445 7721860 7761412
MMDBr0001945	Phosphatidylinositol 4,5-bisphosphate	1-phosphatidyl-1D-myo-inositol 4-phosphate	Not Available	VMH	12728269
MMDBr0001948	1-phosphatidyl-1D-myo-inositol 4-phosphate	Phosphatidylinositol 4,5-bisphosphate	phosphoinositide kinase, FYVE finger containing	VMH	164238 7852364 8841185 8955136
MMDBr0001949	1-phosphatidyl-1D-myo-inositol 4-phosphate	Phosphatidylinositol 4,5-bisphosphate	Not Available	VMH	12728269
MMDBr0001950	1-phosphatidyl-1D-myo-inositol 4-phosphate	Diglyceride	phospholipase C, beta 1 (phosphoinositide-specific)	VMH	10702670 10702683 10760467 11022047 11022048 11118617 12117804 12213492 12416999 13333955 15140260 1644792 2167438 7607669 7612006 7633416 7789993 7835906 7849701 7890667 8530101 9345909
MMDBr0001951	1-phosphatidyl-1D-myo-inositol 4-phosphate	Diglyceride	phospholipase C, beta 1 (phosphoinositide-specific)	VMH	10760467 11118617 12213492

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0061341

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phosphatidylinositol 4-phosphate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Irvine RF: Nuclear lipid signalling. Nat Rev Mol Cell Biol. 2003 May;4(5):349-60. doi: 10.1038/nrm1100. [PubMed:12728269 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
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-1D-myo-inositol 4-phosphate (MMDBc0047840)

MOL for #<Metabolite:0x00007fdb5176eab0>

3D MOL for #<Metabolite:0x00007fdb5176eab0>

3D SDF for #<Metabolite:0x00007fdb5176eab0>

3D-SDF for #<Metabolite:0x00007fdb5176eab0>

PDB for #<Metabolite:0x00007fdb5176eab0>

3D PDB for #<Metabolite:0x00007fdb5176eab0>

SMILES for #<Metabolite:0x00007fdb5176eab0>

INCHI for #<Metabolite:0x00007fdb5176eab0>

Structure for #<Metabolite:0x00007fdb5176eab0>

3D Structure for #<Metabolite:0x00007fdb5176eab0>