Record Information
Version1.0
Created at2020-04-17 19:20:04 UTC
Updated at2020-12-07 19:11:46 UTC
CannabisDB IDCDB005207
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameInositol 1,4,5-trisphosphate
DescriptionInositol 1,4,5-trisphosphate, also known as 1,4,5-insp3 or IP3, 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. Inositol 1,4,5-trisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Inositol 1,4,5-trisphosphate exists in all eukaryotes, ranging from yeast to humans. DG(16:0/18:1(9Z)/0:0) and inositol 1,4,5-trisphosphate can be biosynthesized from pip2[4,5](16:0/18:1(9Z)); which is catalyzed by the enzyme 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1. In humans, inositol 1,4,5-trisphosphate is involved in the metabolic disorder called the joubert syndrome pathway. Inositol 1,4,5-trisphosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
1,4,5-Insp3ChEBI
D-Myo-inositol 1,4,5-trisphosphateChEBI
D-MYO-inositol-1,4,5-triphosphATEChEBI
Ins(1,4,5)P3ChEBI
InsP3ChEBI
IP3ChEBI
1D-Myo-inositol 1,4,5-trisphosphateKegg
D-Myo-inositol 1,4,5-trisphosphoric acidGenerator
D-MYO-inositol-1,4,5-triphosphoric acidGenerator
1D-Myo-inositol 1,4,5-trisphosphoric acidGenerator
Inositol 1,4,5-trisphosphoric acidGenerator
Myo-inositol 1,4,5-trisphosphateHMDB
1,4,5-IP3HMDB
Inositol 1,4,5-triphosphateHMDB
Myoinositol 1,4,5-triphosphateHMDB
D-myo-Inositol 1,4,5-triphosphateHMDB
IP 3HMDB
Inositol 1,4,5-trisphosphateHMDB
Inositol triphosphateHMDB
Inositol trisphosphateHMDB
TriphosphoinositolHMDB
myo-Inositol 1,4,5-triphosphateHMDB
myo-Inositol triphosphateHMDB
myo-Inositol trisphosphateHMDB
Chemical FormulaC6H15O15P3
Average Molecular Weight420.1
Monoisotopic Molecular Weight419.9624
IUPAC Name{[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional NameInsP3
CAS Registry Number85166-31-0
SMILES
O[C@@H]1[C@H](O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H](O)[C@@H]1OP(O)(O)=O
InChI Identifier
InChI=1S/C6H15O15P3/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2+,3+,4-,5-,6-/m1/s1
InChI KeyMMWCIQZXVOZEGG-XJTPDSDZSA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Monoalkyl phosphate
  • Cyclohexanol
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.86ALOGPS
logP-4.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)0.54ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area260.97 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity68.39 m³·mol⁻¹ChemAxon
Polarizability29.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSInositol 1,4,5-trisphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002b-7195200000-2871156f7c1e00704088Spectrum
Predicted GC-MSInositol 1,4,5-trisphosphate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9052133000-5094b6ef55759c5a19ddSpectrum
Predicted GC-MSInositol 1,4,5-trisphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0006-0091000000-66258d5943e8e34a4f1b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-00ba-9030000000-9567cb0f36d067bd98e82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-0udi-0000900000-a08362b50609e78681132020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-0udi-0205900000-c9a653bc0177b1f5ec0c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0udi-1509800000-0c58a55629c8bdde91c42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-0zi0-2709200000-f834442aa900d5925ee02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-0kk9-6908000000-bce10d89581b945182c82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-056r-9603000000-b83a25f979d90dcaacec2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 40V, negativesplash10-004i-9300000000-83996fe12a20b170e2dc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 47V, negativesplash10-004i-9100000000-9c6fa50af864d3ab9ccc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0udi-0109000000-f750488015579ddac3952020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-004i-9000000000-0ae8d2338f48c17984cd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0zfr-0970000000-d129d480332834af86312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-004r-5900000000-4dffa7896e57b68d360e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-08fr-0639000000-1fc55e97bbb62fd985062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0a4i-0943000000-4b6820f7da0e5d5591672020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-014i-0000900000-4422ae3f5c5cbce0813d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-014i-0103900000-60bb04a7db68b52b301a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-05fr-1409300000-c28e47a55145868de89d2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3008900000-e987cfb2603d94f1a6a42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2006900000-95047338604f8928313f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-4291000000-8e9bb388f01ec6d535ab2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4001900000-395b5e207aa26dd43f272016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9003200000-5e6369906fdedd08ad602016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4b72b937fe3bf7fe817e2016-09-12View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1PLCB120p12Q9NQ66 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4PLCB420p12Q15147 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2PLCB215q15Q00722 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3PLCB311q13Q01970 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2PLCG216q24.1P16885 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1PLCG120q12-q13.1P19174 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1PLCD13p22-p21.3P51178 details
Type I inositol 1,4,5-trisphosphate 5-phosphataseINPP5A10q26.3Q14642 details
Phosphatidylinositol 4,5-bisphosphate 5-phosphatase AINPP5J22q12.2Q15735 details
Inositol polyphosphate 5-phosphatase KINPP5K17p13.3Q9BT40 details
Inositol-trisphosphate 3-kinase BITPKB1q42.13P27987 details
Inositol-trisphosphate 3-kinase AITPKA15q15.1P23677 details
Inositol polyphosphate multikinaseIPMK10q21.1Q8NFU5 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-2PLCH21p36.32O75038 details
Inositol-trisphosphate 3-kinase CITPKC19q13.1Q96DU7 details
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2INPPL111q13O15357 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-4PLCD42q35Q9BRC7 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-1PLCH13q25.31Q4KWH8 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase epsilon-1PLCE110q23Q9P212 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3PLCD317q21.31Q8N3E9 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase zeta-1PLCZ112p12.3Q86YW0 details
Multiple inositol polyphosphate phosphatase 1MINPP110q23Q9UNW1 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Inositol 1,4,5-trisphosphate receptor type 1ITPR13p26.1Q14643 details
Inositol 1,4,5-trisphosphate receptor type 2ITPR212p11Q14571 details
Inositol 1,4,5-trisphosphate receptor type 3ITPR36p21Q14573 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1PLCB120p12Q9NQ66 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4PLCB420p12Q15147 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2PLCB215q15Q00722 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3PLCB311q13Q01970 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1PLCD13p22-p21.3P51178 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-2PLCH21p36.32O75038 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-4PLCD42q35Q9BRC7 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-1PLCH13q25.31Q4KWH8 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase epsilon-1PLCE110q23Q9P212 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3PLCD317q21.31Q8N3E9 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase zeta-1PLCZ112p12.3Q86YW0 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1PLCB120p12Q9NQ66 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3PLCB311q13Q01970 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2PLCG216q24.1P16885 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1PLCG120q12-q13.1P19174 details
Inositol polyphosphate 5-phosphatase KINPP5K17p13.3Q9BT40 details
Inositol-trisphosphate 3-kinase BITPKB1q42.13P27987 details
Inositol 1,4,5-trisphosphate receptor type 1ITPR13p26.1Q14643 details
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2INPPL111q13O15357 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase epsilon-1PLCE110q23Q9P212 details
Inositol 1,4,5-trisphosphate receptor type 2ITPR212p11Q14571 details
Inositol 1,4,5-trisphosphate receptor type 3ITPR36p21Q14573 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1PLCB120p12Q9NQ66 details
Inositol polyphosphate 5-phosphatase KINPP5K17p13.3Q9BT40 details
Concentrations Data
Not Available
HMDB IDHMDB0001498
DrugBank IDDB03401
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022657
KNApSAcK IDC00007460
Chemspider ID388562
KEGG Compound IDC01245
BioCyc IDINOSITOL-1-4-5-TRISPHOSPHATE
BiGG ID1485108
Wikipedia LinkInositol trisphosphate
METLIN ID6282
PubChem Compound439456
PDB IDNot Available
ChEBI ID16595
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 49 proteins in total.

Enzymes

General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB1
Uniprot ID:
Q9NQ66
Molecular weight:
138565.805
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. This form has a role in retina signal transduction.
Gene Name:
PLCB4
Uniprot ID:
Q15147
Molecular weight:
136105.065
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB2
Uniprot ID:
Q00722
Molecular weight:
134023.21
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB3
Uniprot ID:
Q01970
Molecular weight:
138797.725
General function:
Involved in phosphoinositide phospholipase C activity
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. It is a crucial enzyme in transmembrane signaling.
Gene Name:
PLCG2
Uniprot ID:
P16885
Molecular weight:
147868.67
General function:
Involved in calcium ion binding
Specific function:
Mediates the production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). Plays an important role in the regulation of intracellular signaling cascades. Becomes activated in response to ligand-mediated activation of receptor-type tyrosine kinases, such as PDGFRA, PDGFRB, FGFR1, FGFR2, FGFR3 and FGFR4. Plays a role in actin reorganization and cell migration.
Gene Name:
PLCG1
Uniprot ID:
P19174
Molecular weight:
148658.92
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. Essential for trophoblast and placental development.
Gene Name:
PLCD1
Uniprot ID:
P51178
Molecular weight:
88134.23
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Major isoenzyme hydrolyzing the calcium-mobilizing second messenger Ins(1,4,5)P3, this is a signal-terminating reaction.
Gene Name:
INPP5A
Uniprot ID:
Q14642
Molecular weight:
47819.155
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Inositol 5-phosphatase, which converts inositol 1,4,5-trisphosphate to inositol 1,4-bisphosphate. Also converts phosphatidylinositol 4,5-bisphosphate to phosphatidylinositol 4-phosphate and inositol 1,3,4,5-tetrakisphosphate to inositol 1,3,4-trisphosphate in vitro. May be involved in modulation of the function of inositol and phosphatidylinositol polyphosphate-binding proteins that are present at membranes ruffles (By similarity).
Gene Name:
INPP5J
Uniprot ID:
Q15735
Molecular weight:
70238.575
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Inositol 5-phosphatase which acts on inositol 1,4,5-trisphosphate, inositol 1,3,4,5-tetrakisphosphate, phosphatidylinositol 4,5-bisphosphate and phosphatidylinositol 3,4,5-trisphosphate. Has 6-fold higher affinity for phosphatidylinositol 4,5-bisphosphate than for inositol 1,4,5-trisphosphate. May negatively regulate assembly of the actin cytoskeleton.
Gene Name:
INPP5K
Uniprot ID:
Q9BT40
Molecular weight:
42783.425

Transporters

General function:
Involved in calcium channel activity
Specific function:
Intracellular channel that mediates calcium release from the endoplasmic reticulum following stimulation by inositol 1,4,5- trisphosphate
Gene Name:
ITPR1
Uniprot ID:
Q14643
Molecular weight:
313942.4
General function:
Involved in calcium channel activity
Specific function:
Receptor for inositol 1,4,5-trisphosphate, a second messenger that mediates the release of intracellular calcium
Gene Name:
ITPR2
Uniprot ID:
Q14571
Molecular weight:
308061.1
General function:
Involved in calcium channel activity
Specific function:
Receptor for inositol 1,4,5-trisphosphate, a second messenger that mediates the release of intracellular calcium
Gene Name:
ITPR3
Uniprot ID:
Q14573
Molecular weight:
304104.0

Only showing the first 10 proteins. There are 49 proteins in total.