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Showing metabocard for myo-Inositol 1,4,5-trisphosphate (HMDB0001498)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:18:17 UTC
HMDB IDHMDB0001498
Secondary Accession Numbers
  • HMDB01498
Metabolite Identification
Common Namemyo-Inositol 1,4,5-trisphosphate
Descriptionmyo-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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001498 (myo-Inositol 1,4,5-trisphosphate)

  Mrv1652309042000242D          

 24 24  0  0  0  0            999 V2000
    0.3552    1.6476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836    0.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    2.0604    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6576    2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814    2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -0.8238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0713   -0.4111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0713    0.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3567    0.8264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3578    0.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3578   -0.4111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0765    0.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755   -1.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3614   -2.0596    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -1.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518   -2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    0.4156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -0.4092    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -0.4100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1968   -1.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833   -0.8201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10  1  1  6  0  0  0
  9  2  1  6  0  0  0
 11 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
  7 17  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 12 22  1  6  0  0  0
  8 24  1  6  0  0  0
M  END
Download

3D MOL for HMDB0001498 (myo-Inositol 1,4,5-trisphosphate)

HMDB0001498
     RDKit          3D
myo-Inositol 1,4,5-trisphosphate
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.0612    1.7223   -0.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2889    0.2461   -0.1430 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.6370   -0.5673   -1.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    0.1135    0.9073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9592   -0.4466    0.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065   -0.3918   -0.1876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8529    0.5204    0.5008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3559    1.8369    0.4081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4721    0.5213   -0.2107 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3219    1.3716    0.5353 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269    2.6165   -0.4037 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.9786    2.1496   -1.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793    2.9993    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806    4.0226   -0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0472   -0.8561   -0.1253 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2498   -0.7982   -0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054   -0.9851    0.0641 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3996   -0.7205    1.5295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7696    0.1479   -0.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518   -2.5235   -0.2133 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544   -1.9393   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5220   -3.1152    0.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -1.7500   -0.4962 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8474   -2.6359    0.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -0.0905   -1.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2937   -0.0536    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188    0.1289   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865    0.2375    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7053    2.1618    1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122    0.8879   -1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157    3.7978   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276    4.8354   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3597   -1.0213    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5126    0.2147    0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5919   -3.1520   -0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638   -2.1652   -1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246   -2.9327    1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801   -2.0827   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -2.3047    1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 15 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23  6  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  6
  7 28  1  1
  8 29  1  0
  9 30  1  6
 13 31  1  0
 14 32  1  0
 15 33  1  1
 19 34  1  0
 20 35  1  0
 21 36  1  6
 22 37  1  0
 23 38  1  6
 24 39  1  0
M  END
Download

3D SDF for HMDB0001498 (myo-Inositol 1,4,5-trisphosphate)

  Mrv1652309042000242D          

 24 24  0  0  0  0            999 V2000
    0.3552    1.6476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836    0.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    2.0604    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6576    2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814    2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -0.8238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0713   -0.4111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0713    0.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3567    0.8264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3578    0.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3578   -0.4111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0765    0.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755   -1.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3614   -2.0596    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -1.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518   -2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    0.4156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -0.4092    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -0.4100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1968   -1.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833   -0.8201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10  1  1  6  0  0  0
  9  2  1  6  0  0  0
 11 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
  7 17  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 12 22  1  6  0  0  0
  8 24  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001498

> <DATABASE_NAME>
hmdb

> <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_KEY>
MMWCIQZXVOZEGG-XJTPDSDZSA-N

> <FORMULA>
C6H15O15P3

> <MOLECULAR_WEIGHT>
420.0956

> <EXACT_MASS>
419.962379346

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.607530919943862

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.86

> <JCHEM_LOGP>
-4.152707746

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-6

> <JCHEM_PKA>
1.036823557327442

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.5363206524866495

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6688996734755257

> <JCHEM_POLAR_SURFACE_AREA>
260.96999999999997

> <JCHEM_REFRACTIVITY>
68.3937

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
InsP3

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001498 (myo-Inositol 1,4,5-trisphosphate)

HMDB0001498
     RDKit          3D
myo-Inositol 1,4,5-trisphosphate
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.0612    1.7223   -0.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2889    0.2461   -0.1430 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.6370   -0.5673   -1.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    0.1135    0.9073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9592   -0.4466    0.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065   -0.3918   -0.1876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8529    0.5204    0.5008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3559    1.8369    0.4081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4721    0.5213   -0.2107 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3219    1.3716    0.5353 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269    2.6165   -0.4037 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.9786    2.1496   -1.8402 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793    2.9993    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806    4.0226   -0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0472   -0.8561   -0.1253 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2498   -0.7982   -0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054   -0.9851    0.0641 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3996   -0.7205    1.5295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7696    0.1479   -0.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518   -2.5235   -0.2133 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544   -1.9393   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5220   -3.1152    0.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -1.7500   -0.4962 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8474   -2.6359    0.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -0.0905   -1.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2937   -0.0536    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188    0.1289   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865    0.2375    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7053    2.1618    1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122    0.8879   -1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157    3.7978   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276    4.8354   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3597   -1.0213    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5126    0.2147    0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5919   -3.1520   -0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638   -2.1652   -1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246   -2.9327    1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801   -2.0827   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -2.3047    1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 15 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23  6  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  6
  7 28  1  1
  8 29  1  0
  9 30  1  6
 13 31  1  0
 14 32  1  0
 15 33  1  1
 19 34  1  0
 20 35  1  0
 21 36  1  6
 22 37  1  0
 23 38  1  6
 24 39  1  0
M  END
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PDB for HMDB0001498 (myo-Inositol 1,4,5-trisphosphate)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       0.663   3.076   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.329   1.539   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0       1.994   3.846   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0       1.228   5.177   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.333   3.072   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.765   5.177   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.666  -1.538   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.000  -0.767   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.000   0.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.666   1.543   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.668   0.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.668  -0.767   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.009   1.515   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.008  -3.073   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0      -0.675  -3.845   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0      -1.442  -5.177   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.666  -3.069   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.097  -5.177   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.331   0.776   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      -3.332  -0.764   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0      -4.870  -0.765   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.990  -1.537   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.101  -2.099   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.329  -1.531   0.000  0.00  0.00           O+0
CONECT    1    3   10                                                       
CONECT    2    9                                                            
CONECT    3    1    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    8   12   17                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10    2                                                  
CONECT   10    9   11    1                                                  
CONECT   11   10   12   13                                                  
CONECT   12    7   11   22                                                  
CONECT   13   11                                                            
CONECT   14   15                                                            
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15    7                                                       
CONECT   18   15                                                            
CONECT   19   20                                                            
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20   12                                                       
CONECT   23   20                                                            
CONECT   24    8                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END
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3D PDB for HMDB0001498 (myo-Inositol 1,4,5-trisphosphate)

COMPND    HMDB0001498
HETATM    1  O1  UNL     1      -4.061   1.722  -0.429  1.00  0.00           O  
HETATM    2  P1  UNL     1      -4.289   0.246  -0.143  1.00  0.00           P  
HETATM    3  O2  UNL     1      -4.637  -0.567  -1.587  1.00  0.00           O  
HETATM    4  O3  UNL     1      -5.603   0.114   0.907  1.00  0.00           O  
HETATM    5  O4  UNL     1      -2.959  -0.447   0.598  1.00  0.00           O  
HETATM    6  C1  UNL     1      -1.807  -0.392  -0.188  1.00  0.00           C  
HETATM    7  C2  UNL     1      -0.853   0.520   0.501  1.00  0.00           C  
HETATM    8  O5  UNL     1      -1.356   1.837   0.408  1.00  0.00           O  
HETATM    9  C3  UNL     1       0.472   0.521  -0.211  1.00  0.00           C  
HETATM   10  O6  UNL     1       1.322   1.372   0.535  1.00  0.00           O  
HETATM   11  P2  UNL     1       1.927   2.617  -0.404  1.00  0.00           P  
HETATM   12  O7  UNL     1       1.979   2.150  -1.840  1.00  0.00           O  
HETATM   13  O8  UNL     1       3.479   2.999   0.139  1.00  0.00           O  
HETATM   14  O9  UNL     1       0.981   4.023  -0.242  1.00  0.00           O  
HETATM   15  C4  UNL     1       1.047  -0.856  -0.125  1.00  0.00           C  
HETATM   16  O10 UNL     1       2.250  -0.798  -0.862  1.00  0.00           O  
HETATM   17  P3  UNL     1       3.605  -0.985   0.064  1.00  0.00           P  
HETATM   18  O11 UNL     1       3.400  -0.721   1.530  1.00  0.00           O  
HETATM   19  O12 UNL     1       4.770   0.148  -0.476  1.00  0.00           O  
HETATM   20  O13 UNL     1       4.252  -2.523  -0.213  1.00  0.00           O  
HETATM   21  C5  UNL     1       0.154  -1.939  -0.604  1.00  0.00           C  
HETATM   22  O14 UNL     1       0.522  -3.115   0.096  1.00  0.00           O  
HETATM   23  C6  UNL     1      -1.289  -1.750  -0.496  1.00  0.00           C  
HETATM   24  O15 UNL     1      -1.847  -2.636   0.460  1.00  0.00           O  
HETATM   25  H1  UNL     1      -5.416  -0.091  -1.989  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.294  -0.054   1.840  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.119   0.129  -1.141  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.686   0.238   1.538  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.705   2.162   1.261  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.412   0.888  -1.243  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.816   3.798  -0.364  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.528   4.835  -0.371  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.360  -1.021   0.940  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.513   0.215   0.162  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.592  -3.152  -0.547  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.464  -2.165  -1.669  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.525  -2.933   1.087  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.780  -2.083  -1.461  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.666  -2.305   1.374  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    3   25
CONECT    4   26
CONECT    5    6
CONECT    6    7   23   27
CONECT    7    8    9   28
CONECT    8   29
CONECT    9   10   15   30
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   31
CONECT   14   32
CONECT   15   16   21   33
CONECT   16   17
CONECT   17   18   18   19   20
CONECT   19   34
CONECT   20   35
CONECT   21   22   23   36
CONECT   22   37
CONECT   23   24   38
CONECT   24   39
END
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SMILES for HMDB0001498 (myo-Inositol 1,4,5-trisphosphate)

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
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INCHI for HMDB0001498 (myo-Inositol 1,4,5-trisphosphate)

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
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H15O15P3
Average Molecular Weight420.0956
Monoisotopic Molecular Weight419.962379346
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
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
  • Neuron
  • Pancreas
  • Platelet
  • Spleen
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03401
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDMI145P
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceCooke, Allan M.; Potter, Barry V. L.; Gigg, Roy. Synthesis of DL-myo-inositol 1,4,5-trisphosphate. Tetrahedron Letters (1987), 28(20), 2305-8.
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1
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
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)details
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + 1,2-Diacyl-sn-glyceroldetails
Enzyme Details
2. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4
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
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)details
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + 1,2-Diacyl-sn-glyceroldetails
Enzyme Details
3. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2
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
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)details
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + 1,2-Diacyl-sn-glyceroldetails
Enzyme Details
4. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3
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
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)details
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + 1,2-Diacyl-sn-glyceroldetails
Enzyme Details
5. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2
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
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)details
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + 1,2-Diacyl-sn-glyceroldetails
Enzyme Details
6. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1
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
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)details
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + 1,2-Diacyl-sn-glyceroldetails
Enzyme Details
7. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1
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
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)details
1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate + Water → myo-Inositol 1,4,5-trisphosphate + 1,2-Diacyl-sn-glyceroldetails
Enzyme Details
8. Type I inositol 1,4,5-trisphosphate 5-phosphatase
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
Reactions
myo-Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
myo-Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
Enzyme Details
9. Phosphatidylinositol 4,5-bisphosphate 5-phosphatase A
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
Reactions
myo-Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
myo-Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
Enzyme Details
10. Inositol polyphosphate 5-phosphatase K
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
Reactions
myo-Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
myo-Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters