MiMeDB: Showing metabocard for Inositol 1,4,5-trisphosphate (MMDBc0032957)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:28:51 UTC

Update Date

2024-10-13 13:55:44 UTC

Metabolite ID

MMDBc0032957

Metabolite Identification

Common Name

Inositol 1,4,5-trisphosphate

Description

myo-Inositol 1,4,5-trisphosphate (CAS: 20298-95-7), also known as Ins(1,4,5)P3 or InsP3, is an intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane (PMID: 22453946 ). It is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin (PMID: 15189149 ). Its transient accumulation is due both to the enhanced metabolism via the Ca2+-calmodulin-sensitive Ins(1,4,5)P3 kinase, as well as a down-regulation of phosphatidylinositol 4,5-bisphosphate hydrolysis (PMID: 3041962 ). It is a major regulator of apoptotic signalling driving calcium (Ca2+) transients from the endoplasmic reticulum to mitochondria, thereby establishing a functional and physical link between these organelles. It also regulates autophagy through the interaction with Beclin 1 complex, and in particular, its inhibition/depletion strongly induces macroautophagy (PMID: 19325567 ). In addition, recent evidence suggests that the penetrating sperm delivers into mammalian eggs a novel isoform of phospholipase C (PLC), which promotes the formation of inositol 1,4,5-trisphosphate (PMID: 15362223 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4,5-Insp3	ChEBI
D-Myo-inositol 1,4,5-trisphosphate	ChEBI
D-MYO-inositol-1,4,5-triphosphATE	ChEBI
Ins(1,4,5)P3	ChEBI
InsP3	ChEBI
IP3	ChEBI
1D-Myo-inositol 1,4,5-trisphosphate	Kegg
D-Myo-inositol 1,4,5-trisphosphoric acid	Generator
D-MYO-inositol-1,4,5-triphosphoric acid	Generator
1D-Myo-inositol 1,4,5-trisphosphoric acid	Generator
Inositol 1,4,5-trisphosphoric acid	Generator
Myo-inositol 1,4,5-trisphosphate	HMDB
1,4,5-IP3	HMDB
Inositol 1,4,5-triphosphate	HMDB
Myoinositol 1,4,5-triphosphate	HMDB
D-myo-Inositol 1,4,5-triphosphate	HMDB
IP 3	HMDB
Inositol 1,4,5-trisphosphate	HMDB
Inositol triphosphate	HMDB
Inositol trisphosphate	HMDB
Triphosphoinositol	HMDB
myo-Inositol 1,4,5-triphosphate	HMDB
myo-Inositol triphosphate	HMDB
myo-Inositol trisphosphate	HMDB

Molecular Formula

C₆H₁₅O₁₅P₃

Average Mass

420.0956

Monoisotopic Mass

419.962379346

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

88269-39-0

SMILES

Not Available

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 Key

MMWCIQZXVOZEGG-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.

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
Monoalkyl phosphate
Cyclohexanol
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Polyol
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

myo-inositol trisphosphate (CHEBI:16595 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Nucleus

Biospecimen Locations

Epidermis
Feces
Neuron
Pancreas
Platelet
Spleen

Tissue Locations

Epidermis
Neuron
Pancreas
Platelet
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191892	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1	Unknown	Q9NQ66	Homo sapiens
MMDBp0191893	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4	Unknown	Q15147	Homo sapiens
MMDBp0191894	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2	Unknown	Q00722	Homo sapiens
MMDBp0191898	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3	Unknown	Q01970	Homo sapiens
MMDBp0191900	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2	Unknown	P16885	Homo sapiens
MMDBp0191914	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1	Unknown	P19174	Homo sapiens
MMDBp0191917	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1	Unknown	P51178	Homo sapiens
MMDBp0192029	Type I inositol 1,4,5-trisphosphate 5-phosphatase	Unknown	Q14642	Homo sapiens
MMDBp0192031	Phosphatidylinositol 4,5-bisphosphate 5-phosphatase A	Enzyme	Q15735	Homo sapiens
MMDBp0192032	Inositol polyphosphate 5-phosphatase K	Enzyme	Q9BT40	Homo sapiens
MMDBp0192595	Inositol-trisphosphate 3-kinase B	Unknown	P27987	Homo sapiens
MMDBp0192596	Inositol-trisphosphate 3-kinase A	Enzyme	P23677	Homo sapiens
MMDBp0192877	Inositol polyphosphate multikinase	Enzyme	Q8NFU5	Homo sapiens
MMDBp0193297	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-2	Unknown	O75038	Homo sapiens
MMDBp0193700	Inositol 1,4,5-trisphosphate receptor type 1	Unknown	Q14643	Homo sapiens
MMDBp0193859	Inositol-trisphosphate 3-kinase C	Unknown	Q96DU7	Homo sapiens
MMDBp0193888	Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2	Enzyme	O15357	Homo sapiens
MMDBp0193974	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-4	Unknown	Q9BRC7	Homo sapiens
MMDBp0193975	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-1	Unknown	Q4KWH8	Homo sapiens
MMDBp0193976	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase epsilon-1	Unknown	Q9P212	Homo sapiens
MMDBp0193977	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3	Unknown	Q8N3E9	Homo sapiens
MMDBp0194136	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase zeta-1	Unknown	Q86YW0	Homo sapiens
MMDBp0194174	Multiple inositol polyphosphate phosphatase 1	Enzyme	Q9UNW1	Homo sapiens
MMDBp0194517	Inositol 1,4,5-trisphosphate receptor type 2	Unknown	Q14571	Homo sapiens
MMDBp0194518	Inositol 1,4,5-trisphosphate receptor type 3	Unknown	Q14573	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Chlorphenamine H1-Antihistamine Action
Pheniramine H1-Antihistamine Action
Dexchlorpheniramine H1-Antihistamine Action
Brompheniramine H1-Antihistamine Action
Dexbrompheniramine H1-Antihistamine Action

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001666	Inositol 1,4,5-trisphosphate	1D-Myo-inositol 1,4,5,6-tetrakisphosphate	inositol polyphosphate multikinase	VMH	12027805 12223481 2906139
MMDBr0001667	Inositol 1,4,5-trisphosphate	1D-Myo-Inositol 1,3,4,5-tetrakisphosphate	inositol-trisphosphate 3-kinase A	VMH	11085927 1654894 2906139
MMDBr0001668	Inositol 1,4,5-trisphosphate	1D-Myo-Inositol 1,3,4,5-tetrakisphosphate	inositol polyphosphate multikinase	VMH	12027805 12223481 2906139
MMDBr0001669	Inositol 1,4,5-trisphosphate	1D-myo-inositol 1,4-bisphosphate	inositol polyphosphate-5-phosphatase, 40kDa	VMH	10593988 10764818 15261714 2906139 7721860 8006039 8013665 8530088 8769125 9428629 9824312
MMDBr0001946	Phosphatidylinositol 4,5-bisphosphate	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
MMDBr0001947	Phosphatidylinositol 4,5-bisphosphate	Diglyceride	phospholipase C, beta 1 (phosphoinositide-specific)	VMH	10760467 11118617 12213492 12728269
MMDBr0010380	1D-Myo-Inositol 1,3,4,5-tetrakisphosphate	Inositol 1,4,5-trisphosphate	multiple inositol-polyphosphate phosphatase 1	VMH; KEGG	30371894
MMDBr0010384	Inositol 1,4,5-trisphosphate	1D-Myo-inositol 1,4,5,6-tetrakisphosphate	inositol polyphosphate multikinase	VMH; KEGG	30371894

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	3	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Epidermis	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001498

DrugBank ID

DB03401

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

INOSITOL-1-4-5-TRISPHOSPHATE

BiGG ID

1485108

Wikipedia Link

Inositol trisphosphate

METLIN ID

6282

PubChem Compound

439456

PDB ID

Not Available

ChEBI ID

16595

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Suganuma A, Nakashima S, Okano Y, Nozawa Y: Mass contents of inositol 1,4,5-trisphosphate and 1,2-diacylglycerol in human platelets stimulated with a thromboxane analogue and thrombin. Thromb Haemost. 1992 Sep 7;68(3):341-5. [PubMed:1440502 ]
Nibbering PH, Zomerdijk TP, van Haastert PJ, van Furth R: A competition binding assay for determination of the inositol (1,4,5)-trisphosphate content of human leucocytes. Biochem Biophys Res Commun. 1990 Jul 31;170(2):755-62. doi: 10.1016/0006-291x(90)92155-s. [PubMed:2383266 ]
Biden TJ, Vallar L, Wollheim CB: Regulation of inositol 1,4,5-trisphosphate metabolism in insulin-secreting RINm5F cells. Biochem J. 1988 Apr 15;251(2):435-40. doi: 10.1042/bj2510435. [PubMed:3041962 ]
Eberhard M, Erne P: Inositol 1,4,5-trisphosphate-induced calcium release in permeabilized platelets is coupled to hydrolysis of inositol 1,4,5-trisphosphate to inositol 1,4-bisphosphate. Biochem Biophys Res Commun. 1993 Aug 31;195(1):19-24. doi: 10.1006/bbrc.1993.2003. [PubMed:8363599 ]
Laffi G, Marra F, Failli P, Ruggiero M, Cecchi E, Carloni V, Giotti A, Gentilini P: Defective signal transduction in platelets from cirrhotics is associated with increased cyclic nucleotides. Gastroenterology. 1993 Jul;105(1):148-56. doi: 10.1016/0016-5085(93)90020-d. [PubMed:8390377 ]
Smith RJ, Justen JM, Nidy EG, Sam LM, Bleasdale JE: Transmembrane signaling in human polymorphonuclear neutrophils: 15(S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid modulates receptor agonist-triggered cell activation. Proc Natl Acad Sci U S A. 1993 Aug 1;90(15):7270-4. doi: 10.1073/pnas.90.15.7270. [PubMed:8394015 ]
Saito H, Nishida A, Shimizu M, Motohashi N, Yamawaki S: Decreased inositol 1,4,5-trisphosphate-specific binding in platelets from alcoholic subjects. Biol Psychiatry. 1996 Nov 1;40(9):886-91. doi: 10.1016/0006-3223(95)00548-X. [PubMed:8896775 ]
Eberhard M, Erne P: Regulation of inositol 1,4,5-trisphosphate-induced calcium release by inositol 1,4,5-trisphosphate and calcium in human platelets. J Recept Signal Transduct Res. 1995 Jan-Mar;15(1-4):297-309. doi: 10.3109/10799899509045222. [PubMed:8903946 ]
Koizumi H, Tanaka H, Ohkawara A: beta-Adrenergic stimulation induces activation of protein kinase C and inositol 1,4,5-trisphosphate increase in epidermis. Exp Dermatol. 1997 Jun;6(3):128-32. doi: 10.1111/j.1600-0625.1997.tb00159.x. [PubMed:9226135 ]
Garlind A, Wiehager B, Winblad B, Fowler CJ: Intracellular inositol (1,4,5)-trisphosphate receptor levels are preserved in Alzheimer's disease platelets. Neurobiol Aging. 1997 Sep-Oct;18(5):559-61. doi: 10.1016/s0197-4580(97)00039-0. [PubMed:9390785 ]
Dwivedi Y, Janicak PG, Pandey GN: Elevated [3H]inositol 1,4,5-trisphosphate binding sites and expressed inositol 1,4,5-trisphosphate receptor protein level in platelets of depressed patients. Psychopharmacology (Berl). 1998 Jul;138(1):47-54. doi: 10.1007/s002130050644. [PubMed:9694526 ]
Vanags DM, Lloyd JV, Rodgers SE, Bochner F: ADP, adrenaline and serotonin stimulate inositol 1,4,5-trisphosphate production in human platelets. Eur J Pharmacol. 1998 Sep 25;358(1):93-100. doi: 10.1016/s0014-2999(98)00595-0. [PubMed:9809874 ]
Petersen OH, Burdakov D, Tepikin AV: Polarity in intracellular calcium signaling. Bioessays. 1999 Oct;21(10):851-60. doi: 10.1002/(SICI)1521-1878(199910)21:10<851::AID-BIES7>3.0.CO;2-F. [PubMed:10497335 ]
Kalra R, Singh SP, Kracko D, Matta SG, Sharp BM, Sopori ML: Chronic self-administration of nicotine in rats impairs T cell responsiveness. J Pharmacol Exp Ther. 2002 Sep;302(3):935-9. doi: 10.1124/jpet.302.3.935. [PubMed:12183649 ]
Brann JH, Dennis JC, Morrison EE, Fadool DA: Type-specific inositol 1,4,5-trisphosphate receptor localization in the vomeronasal organ and its interaction with a transient receptor potential channel, TRPC2. J Neurochem. 2002 Dec;83(6):1452-60. doi: 10.1046/j.1471-4159.2002.01266.x. [PubMed:12472899 ]
Arranz B, Rosel P, Sarro S, Ramirez N, Duenas R, Cano R, Maria Sanchez J, San L: Altered platelet serotonin 5-HT2A receptor density but not second messenger inositol trisphosphate levels in drug-free schizophrenic patients. Psychiatry Res. 2003 May 30;118(2):165-74. doi: 10.1016/s0165-1781(03)00073-8. [PubMed:12798981 ]
Goncalves I, Hughan SC, Schoenwaelder SM, Yap CL, Yuan Y, Jackson SP: Integrin alpha IIb beta 3-dependent calcium signals regulate platelet-fibrinogen interactions under flow. Involvement of phospholipase C gamma 2. J Biol Chem. 2003 Sep 12;278(37):34812-22. doi: 10.1074/jbc.M306504200. Epub 2003 Jun 27. [PubMed:12832405 ]
Patterson RL, Boehning D, Snyder SH: Inositol 1,4,5-trisphosphate receptors as signal integrators. Annu Rev Biochem. 2004;73:437-65. doi: 10.1146/annurev.biochem.73.071403.161303. [PubMed:15189149 ]
Santella L, Lim D, Moccia F: Calcium and fertilization: the beginning of life. Trends Biochem Sci. 2004 Aug;29(8):400-8. doi: 10.1016/j.tibs.2004.06.009. [PubMed:15362223 ]
Willets JM, Nahorski SR, Challiss RA: Roles of phosphorylation-dependent and -independent mechanisms in the regulation of M1 muscarinic acetylcholine receptors by G protein-coupled receptor kinase 2 in hippocampal neurons. J Biol Chem. 2005 May 13;280(19):18950-8. doi: 10.1074/jbc.M412682200. Epub 2005 Mar 2. [PubMed:15743771 ]
Poeckel D, Tausch L, Altmann A, Feisst C, Klinkhardt U, Graff J, Harder S, Werz O: Induction of central signalling pathways and select functional effects in human platelets by beta-boswellic acid. Br J Pharmacol. 2005 Oct;146(4):514-24. doi: 10.1038/sj.bjp.0706366. [PubMed:16086030 ]
Vicencio JM, Ortiz C, Criollo A, Jones AW, Kepp O, Galluzzi L, Joza N, Vitale I, Morselli E, Tailler M, Castedo M, Maiuri MC, Molgo J, Szabadkai G, Lavandero S, Kroemer G: The inositol 1,4,5-trisphosphate receptor regulates autophagy through its interaction with Beclin 1. Cell Death Differ. 2009 Jul;16(7):1006-17. doi: 10.1038/cdd.2009.34. Epub 2009 Mar 27. [PubMed:19325567 ]
Parys JB, De Smedt H: Inositol 1,4,5-trisphosphate and its receptors. Adv Exp Med Biol. 2012;740:255-79. doi: 10.1007/978-94-007-2888-2_11. [PubMed:22453946 ]

Showing metabocard for Inositol 1,4,5-trisphosphate (MMDBc0032957)

MOL for #<Metabolite:0x00007fdaf3bdbf98>

3D MOL for #<Metabolite:0x00007fdaf3bdbf98>

3D SDF for #<Metabolite:0x00007fdaf3bdbf98>

3D-SDF for #<Metabolite:0x00007fdaf3bdbf98>

PDB for #<Metabolite:0x00007fdaf3bdbf98>

3D PDB for #<Metabolite:0x00007fdaf3bdbf98>

SMILES for #<Metabolite:0x00007fdaf3bdbf98>

INCHI for #<Metabolite:0x00007fdaf3bdbf98>

Structure for #<Metabolite:0x00007fdaf3bdbf98>

3D Structure for #<Metabolite:0x00007fdaf3bdbf98>