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Showing metabocard for 3-Hydroxy-3-methylglutaryl-CoA (HMDB0001375)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:37:24 UTC
HMDB IDHMDB0001375
Secondary Accession Numbers
  • HMDB01375
Metabolite Identification
Common Name3-Hydroxy-3-methylglutaryl-CoA
Description3-Hydroxy-3-methylglutaryl-CoA (HMG-CoA) (CAS: 1553-55-5) is formed when acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes (PMID: 14689582 ).
Structure
Data?1583445288
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)


  Mrv1652303102018232D          

 58 60  0  0  1  0            999 V2000
   27.2588   -1.4900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.5913   -1.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0039   -2.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.9239   -1.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1788   -2.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.4888   -2.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5131   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2559   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7986   -5.9435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0842   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3697   -5.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -4.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0842   -4.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -3.4685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3981   -3.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -3.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5415   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4145   -1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -1.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2395   -1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -2.2309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3980   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2559   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9059   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5559   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -1.8184    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -1.8184    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.1393   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -2.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8689   -3.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5189   -3.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -3.7671    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -4.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0434   -1.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6566   -1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3790   -0.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3710   -1.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6566   -2.6121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1995   -0.5676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0855   -1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3711   -3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0855   -2.6120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7999   -1.3745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9704   -5.5310    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.6849   -6.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6849   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3994   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8283   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428   -6.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2573   -5.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5263   -6.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1138   -5.9435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7013   -6.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 57  1  0  0  0  0
 57 52  1  0  0  0  0
 52 54  1  0  0  0  0
 54 53  2  0  0  0  0
 54 55  1  0  0  0  0
 57 56  1  1  0  0  0
 57 58  1  6  0  0  0
M  END
Download

3D MOL for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

Download
3D SDF for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

  Mrv1652303102018232D          

 58 60  0  0  1  0            999 V2000
   27.2588   -1.4900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.5913   -1.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0039   -2.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.9239   -1.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1788   -2.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.4888   -2.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5131   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2559   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7986   -5.9435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0842   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3697   -5.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -4.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0842   -4.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -3.4685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3981   -3.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -3.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5415   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4145   -1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -1.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2395   -1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -2.2309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3980   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2559   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9059   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5559   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -1.8184    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -1.8184    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.1393   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -2.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8689   -3.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5189   -3.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -3.7671    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -4.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0434   -1.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6566   -1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3790   -0.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3710   -1.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6566   -2.6121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1995   -0.5676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0855   -1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3711   -3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0855   -2.6120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7999   -1.3745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9704   -5.5310    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.6849   -6.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6849   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3994   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8283   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428   -6.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2573   -5.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5263   -6.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1138   -5.9435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7013   -6.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 57  1  0  0  0  0
 57 52  1  0  0  0  0
 52 54  1  0  0  0  0
 54 53  2  0  0  0  0
 54 55  1  0  0  0  0
 57 56  1  1  0  0  0
 57 58  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001375

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1

> <INCHI_KEY>
CABVTRNMFUVUDM-VRHQGPGLSA-N

> <FORMULA>
C27H44N7O20P3S

> <MOLECULAR_WEIGHT>
911.659

> <EXACT_MASS>
911.157467109

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
82.3702140669648

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-6.406678756765139

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.8977913368307053

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8207666712061181

> <JCHEM_PKA_STRONGEST_BASIC>
3.810786962925538

> <JCHEM_POLAR_SURFACE_AREA>
421.1599999999999

> <JCHEM_REFRACTIVITY>
193.70200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
HMG-CoA

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)
https://cactus.nci.nih.gov/chemical/structure/C%5BC@%5D(O)(CC(O)=O)CC(=O)SCCN...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:101})
102104  0  0  0  0  0  0  0  0999 V2000
  -16.6455   -3.0540    0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3889   -2.3508    0.3839 C   0  0  2  0  0  0  0  0  0  0  0  0
  -15.7661   -1.2264   -0.4132 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5712   -3.3264   -0.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4014   -3.7941   -1.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8857   -4.6610   -2.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1271    3.1036   -3.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8372    3.6713   -1.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9105    1.2689   -0.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3193    1.0744   -0.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7858   -2.4839    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7757    1.0280    1.7769 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5121   -3.5995   -1.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5682   -4.8386   -2.0189 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7334   -7.4173    0.3227 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2808   -6.9867   -0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0617   -7.8707   -1.8923 N   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  2  0  0  0  0
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 26 84  1  0  0  0  0
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 28 91  1  0  0  0  0
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 54 58  1  0  0  0  0
 55 56  2  0  0  0  0
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 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
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 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 63101  1  0  0  0  0
 63102  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      50.883  -2.781   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      49.637  -1.876   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      50.407  -4.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      48.391  -2.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      48.867  -4.246   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      51.312  -5.492   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      38.291 -10.325   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.678 -11.095   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      36.957 -11.095   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      35.624 -10.325   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      34.290 -11.095   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      37.010  -8.015   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.624  -8.785   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      37.010  -6.475   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      34.343  -6.475   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      35.677  -5.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.344  -4.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.240  -2.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.010  -3.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.780  -2.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.677  -4.164   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      34.343  -3.394   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      39.678  -3.394   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      42.758  -3.394   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      45.838  -3.394   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      41.218  -1.854   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      41.218  -4.934   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      44.297  -1.854   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      44.297  -4.934   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      41.218  -3.394   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      44.297  -3.394   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      46.927  -2.306   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      47.962  -5.492   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      46.422  -7.032   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      49.502  -7.032   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      47.962  -7.032   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      47.962  -8.572   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      52.348  -2.306   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      53.492  -3.336   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      52.974  -0.899   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      54.826  -2.566   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      53.492  -4.876   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      54.506  -1.060   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      56.160  -3.336   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      54.826  -5.646   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      56.160  -4.876   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      57.493  -2.566   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      41.011 -10.325   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      42.345 -12.635   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      42.345 -11.095   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      43.679 -10.325   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      46.346 -10.325   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      47.680 -12.635   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      47.680 -11.095   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      49.014 -10.325   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      45.782 -12.428   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      45.012 -11.095   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      44.242 -12.428   0.000  0.00  0.00           O+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   48                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   50                                                       
CONECT   49   50                                                            
CONECT   50   48   49   51                                                  
CONECT   51   50   57                                                       
CONECT   52   57   54                                                       
CONECT   53   54                                                            
CONECT   54   52   53   55                                                  
CONECT   55   54                                                            
CONECT   56   57                                                            
CONECT   57   51   52   56   58                                             
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

Download
3D PDB for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)
COMPND    https://cactus.nci.nih.gov/chemical/structure/C%5BC@%5D(O)(CC(O)=O)CC(=O)SCCN... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1     -16.645  -3.054   0.901  1.00  0.00           C  
HETATM    2  C   UNL     1     -15.389  -2.351   0.384  1.00  0.00           C  
HETATM    3  O   UNL     1     -15.766  -1.226  -0.413  1.00  0.00           O  
HETATM    4  C   UNL     1     -14.571  -3.326  -0.465  1.00  0.00           C  
HETATM    5  C   UNL     1     -15.401  -3.794  -1.633  1.00  0.00           C  
HETATM    6  O   UNL     1     -14.886  -4.661  -2.518  1.00  0.00           O  
HETATM    7  O   UNL     1     -16.531  -3.389  -1.771  1.00  0.00           O  
HETATM    8  C   UNL     1     -14.546  -1.876   1.569  1.00  0.00           C  
HETATM    9  C   UNL     1     -13.303  -1.193   1.060  1.00  0.00           C  
HETATM   10  O   UNL     1     -13.161  -0.999  -0.129  1.00  0.00           O  
HETATM   11  S   UNL     1     -12.091  -0.690   2.160  1.00  0.00           S  
HETATM   12  C   UNL     1     -10.900   0.034   1.005  1.00  0.00           C  
HETATM   13  C   UNL     1      -9.695   0.566   1.783  1.00  0.00           C  
HETATM   14  N   UNL     1      -8.730   1.152   0.849  1.00  0.00           N  
HETATM   15  C   UNL     1      -7.583   1.687   1.312  1.00  0.00           C  
HETATM   16  O   UNL     1      -7.349   1.684   2.502  1.00  0.00           O  
HETATM   17  C   UNL     1      -6.591   2.289   0.350  1.00  0.00           C  
HETATM   18  C   UNL     1      -5.386   2.822   1.128  1.00  0.00           C  
HETATM   19  N   UNL     1      -4.421   3.407   0.194  1.00  0.00           N  
HETATM   20  C   UNL     1      -3.274   3.942   0.656  1.00  0.00           C  
HETATM   21  O   UNL     1      -3.084   4.028   1.851  1.00  0.00           O  
HETATM   22  C   UNL     1      -2.229   4.435  -0.311  1.00  0.00           C  
HETATM   23  H   UNL     1      -1.963   5.463  -0.065  1.00  0.00           H  
HETATM   24  O   UNL     1      -2.748   4.382  -1.641  1.00  0.00           O  
HETATM   25  C   UNL     1      -0.985   3.549  -0.213  1.00  0.00           C  
HETATM   26  C   UNL     1      -0.398   3.648   1.197  1.00  0.00           C  
HETATM   27  C   UNL     1      -1.370   2.097  -0.504  1.00  0.00           C  
HETATM   28  C   UNL     1       0.055   4.016  -1.233  1.00  0.00           C  
HETATM   29  O   UNL     1       1.216   3.188  -1.141  1.00  0.00           O  
HETATM   30  P   UNL     1       2.515   3.393  -2.071  1.00  0.00           P  
HETATM   31  O   UNL     1       2.127   3.104  -3.606  1.00  0.00           O  
HETATM   32  O   UNL     1       3.001   4.785  -1.939  1.00  0.00           O  
HETATM   33  O   UNL     1       3.672   2.374  -1.608  1.00  0.00           O  
HETATM   34  P   UNL     1       5.269   2.329  -1.811  1.00  0.00           P  
HETATM   35  O   UNL     1       5.606   1.884  -3.321  1.00  0.00           O  
HETATM   36  O   UNL     1       5.837   3.671  -1.554  1.00  0.00           O  
HETATM   37  O   UNL     1       5.910   1.269  -0.783  1.00  0.00           O  
HETATM   38  C   UNL     1       7.319   1.074  -0.643  1.00  0.00           C  
HETATM   39  C   UNL     1       7.584   0.000   0.413  1.00  0.00           C  
HETATM   40  H   UNL     1       7.082   0.264   1.344  1.00  0.00           H  
HETATM   41  O   UNL     1       7.108  -1.273  -0.055  1.00  0.00           O  
HETATM   42  C   UNL     1       8.007  -2.276   0.466  1.00  0.00           C  
HETATM   43  H   UNL     1       7.786  -2.484   1.513  1.00  0.00           H  
HETATM   44  C   UNL     1       9.404  -1.619   0.323  1.00  0.00           C  
HETATM   45  H   UNL     1       9.780  -1.722  -0.694  1.00  0.00           H  
HETATM   46  O   UNL     1      10.326  -2.172   1.264  1.00  0.00           O  
HETATM   47  C   UNL     1       9.100  -0.134   0.656  1.00  0.00           C  
HETATM   48  H   UNL     1       9.652   0.527  -0.011  1.00  0.00           H  
HETATM   49  O   UNL     1       9.422   0.149   2.019  1.00  0.00           O  
HETATM   50  P   UNL     1      10.483   1.280   2.452  1.00  0.00           P  
HETATM   51  O   UNL     1       9.927   2.729   2.024  1.00  0.00           O  
HETATM   52  O   UNL     1      10.693   1.235   4.048  1.00  0.00           O  
HETATM   53  O   UNL     1      11.776   1.028   1.777  1.00  0.00           O  
HETATM   54  N   UNL     1       7.928  -3.503  -0.330  1.00  0.00           N  
HETATM   55  C   UNL     1       7.512  -3.599  -1.625  1.00  0.00           C  
HETATM   56  N   UNL     1       7.568  -4.839  -2.019  1.00  0.00           N  
HETATM   57  C   UNL     1       8.022  -5.614  -1.005  1.00  0.00           C  
HETATM   58  C   UNL     1       8.263  -4.766   0.089  1.00  0.00           C  
HETATM   59  N   UNL     1       8.720  -5.288   1.222  1.00  0.00           N  
HETATM   60  C   UNL     1       8.945  -6.581   1.323  1.00  0.00           C  
HETATM   61  N   UNL     1       8.733  -7.417   0.323  1.00  0.00           N  
HETATM   62  C   UNL     1       8.281  -6.987  -0.850  1.00  0.00           C  
HETATM   63  N   UNL     1       8.062  -7.871  -1.892  1.00  0.00           N  
HETATM   64  H   UNL     1     -17.314  -3.263   0.066  1.00  0.00           H  
HETATM   65  H   UNL     1     -16.365  -3.990   1.385  1.00  0.00           H  
HETATM   66  H   UNL     1     -17.152  -2.410   1.620  1.00  0.00           H  
HETATM   67  H   UNL     1     -15.018  -0.732  -0.775  1.00  0.00           H  
HETATM   68  H   UNL     1     -13.676  -2.825  -0.833  1.00  0.00           H  
HETATM   69  H   UNL     1     -14.284  -4.184   0.143  1.00  0.00           H  
HETATM   70  H   UNL     1     -15.456  -4.932  -3.250  1.00  0.00           H  
HETATM   71  H   UNL     1     -15.126  -1.175   2.170  1.00  0.00           H  
HETATM   72  H   UNL     1     -14.265  -2.733   2.182  1.00  0.00           H  
HETATM   73  H   UNL     1     -10.569  -0.728   0.300  1.00  0.00           H  
HETATM   74  H   UNL     1     -11.372   0.852   0.461  1.00  0.00           H  
HETATM   75  H   UNL     1     -10.026   1.328   2.489  1.00  0.00           H  
HETATM   76  H   UNL     1      -9.223  -0.252   2.327  1.00  0.00           H  
HETATM   77  H   UNL     1      -8.917   1.154  -0.103  1.00  0.00           H  
HETATM   78  H   UNL     1      -6.260   1.527  -0.355  1.00  0.00           H  
HETATM   79  H   UNL     1      -7.063   3.107  -0.194  1.00  0.00           H  
HETATM   80  H   UNL     1      -5.717   3.584   1.834  1.00  0.00           H  
HETATM   81  H   UNL     1      -4.914   2.003   1.672  1.00  0.00           H  
HETATM   82  H   UNL     1      -4.608   3.409  -0.758  1.00  0.00           H  
HETATM   83  H   UNL     1      -3.006   3.496  -1.927  1.00  0.00           H  
HETATM   84  H   UNL     1      -1.081   3.185   1.909  1.00  0.00           H  
HETATM   85  H   UNL     1       0.562   3.134   1.227  1.00  0.00           H  
HETATM   86  H   UNL     1      -0.257   4.697   1.458  1.00  0.00           H  
HETATM   87  H   UNL     1      -1.788   2.026  -1.508  1.00  0.00           H  
HETATM   88  H   UNL     1      -0.484   1.466  -0.434  1.00  0.00           H  
HETATM   89  H   UNL     1      -2.111   1.765   0.223  1.00  0.00           H  
HETATM   90  H   UNL     1      -0.363   3.945  -2.237  1.00  0.00           H  
HETATM   91  H   UNL     1       0.329   5.050  -1.025  1.00  0.00           H  
HETATM   92  H   UNL     1       1.800   2.208  -3.767  1.00  0.00           H  
HETATM   93  H   UNL     1       5.263   1.012  -3.559  1.00  0.00           H  
HETATM   94  H   UNL     1       7.738   0.756  -1.598  1.00  0.00           H  
HETATM   95  H   UNL     1       7.787   2.010  -0.335  1.00  0.00           H  
HETATM   96  H   UNL     1      10.479  -3.121   1.153  1.00  0.00           H  
HETATM   97  H   UNL     1       9.081   2.962   2.430  1.00  0.00           H  
HETATM   98  H   UNL     1      11.321   1.891   4.380  1.00  0.00           H  
HETATM   99  H   UNL     1       7.184  -2.770  -2.234  1.00  0.00           H  
HETATM  100  H   UNL     1       9.317  -6.973   2.258  1.00  0.00           H  
HETATM  101  H   UNL     1       8.239  -8.817  -1.771  1.00  0.00           H  
HETATM  102  H   UNL     1       7.731  -7.544  -2.744  1.00  0.00           H  
CONECT    1    2   64   65   66                                       
CONECT    2    1    3    4    8                                       
CONECT    3    2   67                                                 
CONECT    4    2    5   68   69                                       
CONECT    5    4    6    7    7                                       
CONECT    6    5   70                                                 
CONECT    7    5    5                                                 
CONECT    8    2    9   71   72                                       
CONECT    9    8   10   10   11                                       
CONECT   10    9    9                                                 
CONECT   11    9   12                                                 
CONECT   12   11   13   73   74                                       
CONECT   13   12   14   75   76                                       
CONECT   14   13   15   77                                            
CONECT   15   14   16   16   17                                       
CONECT   16   15   15                                                 
CONECT   17   15   18   78   79                                       
CONECT   18   17   19   80   81                                       
CONECT   19   18   20   82                                            
CONECT   20   19   21   21   22                                       
CONECT   21   20   20                                                 
CONECT   22   20   23   24   25                                       
CONECT   23   22                                                      
CONECT   24   22   83                                                 
CONECT   25   22   26   27   28                                       
CONECT   26   25   84   85   86                                       
CONECT   27   25   87   88   89                                       
CONECT   28   25   29   90   91                                       
CONECT   29   28   30                                                 
CONECT   30   29   31   32   32                                       
CONECT   30   33                                                      
CONECT   31   30   92                                                 
CONECT   32   30   30                                                 
CONECT   33   30   34                                                 
CONECT   34   33   35   36   36                                       
CONECT   34   37                                                      
CONECT   35   34   93                                                 
CONECT   36   34   34                                                 
CONECT   37   34   38                                                 
CONECT   38   37   39   94   95                                       
CONECT   39   38   40   41   47                                       
CONECT   40   39                                                      
CONECT   41   39   42                                                 
CONECT   42   41   43   44   54                                       
CONECT   43   42                                                      
CONECT   44   42   45   46   47                                       
CONECT   45   44                                                      
CONECT   46   44   96                                                 
CONECT   47   44   48   39   49                                       
CONECT   48   47                                                      
CONECT   49   47   50                                                 
CONECT   50   49   51   52   53                                       
CONECT   50   53                                                      
CONECT   51   50   97                                                 
CONECT   52   50   98                                                 
CONECT   53   50   50                                                 
CONECT   54   42   55   58                                            
CONECT   55   54   56   56   99                                       
CONECT   56   55   55   57                                            
CONECT   57   56   58   58   62                                       
CONECT   58   57   57   54   59                                       
CONECT   59   58   60   60                                            
CONECT   60   59   59   61  100                                       
CONECT   61   60   62   62                                            
CONECT   62   61   61   57   63                                       
CONECT   63   62  101  102                                            
CONECT   64    1                                                      
CONECT   65    1                                                      
CONECT   66    1                                                      
CONECT   67    3                                                      
CONECT   68    4                                                      
CONECT   69    4                                                      
CONECT   70    6                                                      
CONECT   71    8                                                      
CONECT   72    8                                                      
CONECT   73   12                                                      
CONECT   74   12                                                      
CONECT   75   13                                                      
CONECT   76   13                                                      
CONECT   77   14                                                      
CONECT   78   17                                                      
CONECT   79   17                                                      
CONECT   80   18                                                      
CONECT   81   18                                                      
CONECT   82   19                                                      
CONECT   83   24                                                      
CONECT   84   26                                                      
CONECT   85   26                                                      
CONECT   86   26                                                      
CONECT   87   27                                                      
CONECT   88   27                                                      
CONECT   89   27                                                      
CONECT   90   28                                                      
CONECT   91   28                                                      
CONECT   92   31                                                      
CONECT   93   35                                                      
CONECT   94   38                                                      
CONECT   95   38                                                      
CONECT   96   46                                                      
CONECT   97   51                                                      
CONECT   98   52                                                      
CONECT   99   55                                                      
CONECT  100   60                                                      
CONECT  101   63                                                      
CONECT  102   63                                                      
MASTER        0    0    0    0    0    0    0    0  102    0  102    0
END

Download
SMILES for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)
C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
Download
INCHI for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)
InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
(3S)-3-Hydroxy-3-methylglutaryl-coenzyme AChEBI
(S)-3-Hydroxy-3-methylglutaryl-coenzyme AChEBI
3-Hydroxy-3-methylglutaryl-CoAChEBI
HMG-CoAChEBI
HMG-coenzyme AChEBI
Hydroxymethylglutaroyl coenzyme AChEBI
Hydroxymethylglutaryl-CoAChEBI
(3S)-3-Hydroxy-3-methylglutaryl-CoAHMDB
(S)-3-Hydroxy-3-methylglutaryl coenzyme AHMDB
(S)-3-Hydroxy-3-methylglutaryl-CoAHMDB
3-Hydroxy-3-methylglutaryl CoAHMDB
3-Hydroxy-3-methylglutaryl coenzyme AHMDB
Hydroxymethylglutaryl CoAHMDB
Hydroxymethylglutaryl coenzyme AHMDB
beta-Hydroxy-beta-methylglutaryl CoAHMDB
beta-Hydroxy-beta-methylglutaryl-CoAHMDB
beta-Hydroxy-beta-methylglutaryl-coenzyme AHMDB
β-Hydroxy-β-methylglutaryl CoAHMDB
β-Hydroxy-β-methylglutaryl-CoAHMDB
β-Hydroxy-β-methylglutaryl-coenzyme AHMDB
Chemical FormulaC27H44N7O20P3S
Average Molecular Weight911.659
Monoisotopic Molecular Weight911.157467109
IUPAC Name(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid
Traditional NameHMG-CoA
CAS Registry Number26926-09-0
SMILES
C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1
InChI KeyCABVTRNMFUVUDM-VRHQGPGLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as (s)-3-hydroxy-3-alkylglutaryl coas. These are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acyl thioesters  
Direct Parent(S)-3-hydroxy-3-alkylglutaryl CoAs  
Alternative Parents
Substituents
  • Coenzyme a or derivatives
    • 

  • Purine ribonucleoside 3',5'-bisphosphate
    • 

  • Purine ribonucleoside bisphosphate
    • 

  • Purine ribonucleoside diphosphate
    • 

  • Ribonucleoside 3'-phosphate
    • 

  • Pentose phosphate
    • 

  • Pentose-5-phosphate
    • 

  • Beta amino acid or derivatives
    • 

  • Glycosyl compound
    • 

  • N-glycosyl compound
    • 

  • 6-aminopurine
    • 

  • Monosaccharide phosphate
    • 

  • Organic pyrophosphate
    • 

  • Pentose monosaccharide
    • 

  • Imidazopyrimidine
    • 

  • Purine
    • 

  • Monoalkyl phosphate
    • 

  • Aminopyrimidine
    • 

  • Alkyl phosphate
    • 

  • Imidolactam
    • 

  • N-acyl-amine
    • 

  • N-substituted imidazole
    • 

  • Organic phosphoric acid derivative
    • 

  • Monosaccharide
    • 

  • Fatty amide
    • 

  • Pyrimidine
    • 

  • Phosphoric acid ester
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Imidazole
    • 

  • Heteroaromatic compound
    • 

  • Azole
    • 

  • Secondary alcohol
    • 

  • Thiocarboxylic acid ester
    • 

  • Amino acid
    • 

  • Carboxamide group
    • 

  • Amino acid or derivatives
    • 

  • Carbothioic s-ester
    • 

  • Secondary carboxylic acid amide
    • 

  • Organoheterocyclic compound
    • 

  • Sulfenyl compound
    • 

  • Thiocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Primary amine
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organosulfur compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Alcohol
    • 

  • Amine
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition
Route of exposure:
Source:
Biological location:
Process
Naturally occurring process:
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
Water Solubility4.1 g/LALOGPS
logP-0.53ALOGPS
logP-6.4ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)3.81ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area421.16 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity193.7 m³·mol⁻¹ChemAxon
Polarizability82.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
MSMass Spectrum (Electron Ionization)splash10-0002-7201092120-9e7970777d7cce6dc6742021-09-05View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-000l-0891000250-052d51ef28faa9ab5b732016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-000i-0971100000-dc16942c0a4531c8cb602016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-000i-1950000000-12dcb50a3caaf20a9aa52016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-00o4-4901031462-49fbf273ff8df18347bb2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-001i-3900110010-0be1f0212b5d814ea24c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-057i-6900100000-fffa063c59d4fcd54e7a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-03dm-0000000094-b818de142848216a6af32021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0a4u-9500001521-8d0d8c41c4c284cc696f2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-004m-9202503430-001456d7b42e545847022021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-03di-0000000169-47d0ed82d5acca38b9e02021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-002r-1500000391-9d63a322b718612b85872021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0a4i-0011900000-766a56d8ca47934345902021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
    • 

  • Extracellular
    • 

  • Membrane
    • 

  • Mitochondria
    • 

  • Endoplasmic reticulum
    • 

  • Peroxisome
Biospecimen LocationsNot Available
Tissue Locations
  • Adrenal Gland
    • 

  • Fibroblasts
    • 

  • Intestine
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030158  
KNApSAcK IDC00007270  
Chemspider ID392859  
KEGG Compound IDC00356  
BioCyc ID3-HYDROXY-3-METHYL-GLUTARYL-COA  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound445127  
PDB IDNot Available
ChEBI ID15467  
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceWilliamson I P; Rodwell V W  Isolation and purification of 3-hydroxy-3-methylglutaryl-coenzyme A by ion-exchange chromatography.    Journal of lipid research  (1981),  22(1),  184-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Li X, Liu L, Tupper JC, Bannerman DD, Winn RK, Sebti SM, Hamilton AD, Harlan JM: Inhibition of protein geranylgeranylation and RhoA/RhoA kinase pathway induces apoptosis in human endothelial cells. J Biol Chem. 2002 May 3;277(18):15309-16. Epub 2002 Feb 11. [PubMed:11839765  ] 
  2. Mital BK, Garg SK: Anticarcinogenic, hypocholesterolemic, and antagonistic activities of Lactobacillus acidophilus. Crit Rev Microbiol. 1995;21(3):175-214. [PubMed:8845062  ] 
  3. Nozaki S, Nakagawa T, Nakata A, Yamashita S, Kameda-Takemura K, Nakamura T, Keno Y, Tokunaga K, Matsuzawa Y: Effects of pravastatin on plasma and urinary mevalonate concentrations in subjects with familial hypercholesterolaemia: a comparison of morning and evening administration. Eur J Clin Pharmacol. 1996;49(5):361-4. [PubMed:8866629  ] 
  4. Ubels FL, Muntinga JH, van Doormaal JJ, Reitsma WD, Smit AJ: Effects of initial and long-term lipid-lowering therapy on vascular wall characteristics. Atherosclerosis. 2001 Jan;154(1):155-61. [PubMed:11137095  ] 
  5. Huang L, Wang Y, Grimm S: ATP-dependent transport of rosuvastatin in membrane vesicles expressing breast cancer resistance protein. Drug Metab Dispos. 2006 May;34(5):738-42. Epub 2006 Jan 13. [PubMed:16415124  ] 
  6. Sato T, Oouchi M, Nagakubo H, Chiba T, Ogawa S, Sato C, Sugimura K, Fukuda M: Effect of pravastatin on plasma ketone bodies in diabetics with hypercholesterolemia. Tohoku J Exp Med. 1998 May;185(1):25-9. [PubMed:9710942  ] 
  7. Son BK, Kozaki K, Iijima K, Eto M, Kojima T, Ota H, Senda Y, Maemura K, Nakano T, Akishita M, Ouchi Y: Statins protect human aortic smooth muscle cells from inorganic phosphate-induced calcification by restoring Gas6-Axl survival pathway. Circ Res. 2006 Apr 28;98(8):1024-31. Epub 2006 Mar 23. [PubMed:16556867  ] 
  8. Gianni L, Di Padova F, Zuin M, Podda M: Bile acid-induced inhibition of the lymphoproliferative response to phytohemagglutinin and pokeweed mitogen: an in vitro study. Gastroenterology. 1980 Feb;78(2):231-5. [PubMed:7350045  ] 
  9. Jenke HS, Lowel M, Berndt J: Effect of alterations in vitro and in vivo of the cholesterol content in rat liver microsomes on the activity of 3-hydroxy-3-methylglutaryl-CoA reductase. Hoppe Seylers Z Physiol Chem. 1983 Feb;364(2):135-40. [PubMed:6840702  ] 
  10. Naseem SM, Heald FP: Sex mediated lipid metabolism in human aortic smooth muscle cells. Biochem Biophys Res Commun. 1987 Apr 14;144(1):284-91. [PubMed:3579907  ] 
  11. Wysocki SJ, Wilkinson SP, Hahnel R, Wong CY, Panegyres PK: 3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria. Clin Chim Acta. 1976 Aug 2;70(3):399-406. [PubMed:947633  ] 
  12. Knight BL, Patel DD, Soutar AK: The regulation of 3-hydroxy-3-methylglutaryl-CoA reductase activity, cholesterol esterification and the expression of low-density lipoprotein receptors in cultured monocyte-derived macrophages. Biochem J. 1983 Feb 15;210(2):523-32. [PubMed:6305342  ] 
  13. Lange Y, Ye J, Steck TL: Activation of membrane cholesterol by displacement from phospholipids. J Biol Chem. 2005 Oct 28;280(43):36126-31. Epub 2005 Aug 29. [PubMed:16129675  ] 
  14. Martin J, Denver R, Bailey M, Krum H: In vitro inhibitory effects of atorvastatin on cardiac fibroblasts: implications for ventricular remodelling. Clin Exp Pharmacol Physiol. 2005 Sep;32(9):697-701. [PubMed:16173924  ] 
  15. Plotkin D, Miller S, Nakajima S, Peskin E, Burkman R, Richardson D, Mitchel Y, Waldstreicher J, Liu M, Shapiro D, Santoro N: Lowering low density lipoprotein cholesterol with simvastatin, a hydroxy-3-methylglutaryl-coenzyme a reductase inhibitor, does not affect luteal function in premenopausal women. J Clin Endocrinol Metab. 2002 Jul;87(7):3155-61. [PubMed:12107216  ] 
  16. Gil G, Smith JR, Goldstein JL, Brown MS: Optional exon in the 5'-untranslated region of 3-hydroxy-3-methylglutaryl coenzyme A synthase gene: conserved sequence and splicing pattern in humans and hamsters. Proc Natl Acad Sci U S A. 1987 Apr;84(7):1863-6. [PubMed:3470763  ] 
  17. Freeman MR, Solomon KR: Cholesterol and prostate cancer. J Cell Biochem. 2004 Jan 1;91(1):54-69. [PubMed:14689582  ] 
Enzymes
  Enzyme Details
1. Hydroxymethylglutaryl-CoA lyase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Key enzyme in ketogenesis (ketone body formation). Terminal step in leucine catabolism.

Gene Name:
HMGCL
Uniprot ID:
P35914  
Molecular weight:
34359.84
Reactions
3-Hydroxy-3-methylglutaryl-CoA → Acetyl-CoA + Acetoacetic aciddetails
  Enzyme Details
2. Hydroxymethylglutaryl-CoA synthase, mitochondrial
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.

Gene Name:
HMGCS2
Uniprot ID:
P54868  
Molecular weight:
52481.065
Reactions
Acetyl-CoA + Water + Acetoacetyl-CoA → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme Adetails
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A → Acetyl-CoA + Water + Acetoacetyl-CoAdetails
  Enzyme Details
3. Hydroxymethylglutaryl-CoA synthase, cytoplasmic
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.

Gene Name:
HMGCS1
Uniprot ID:
Q01581  
Molecular weight:
57293.105
Reactions
Acetyl-CoA + Water + Acetoacetyl-CoA → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme Adetails
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A → Acetyl-CoA + Water + Acetoacetyl-CoAdetails
  Enzyme Details
4. 3-hydroxy-3-methylglutaryl-coenzyme A reductase
General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.

Gene Name:
HMGCR
Uniprot ID:
P04035  
Molecular weight:
97475.155
Reactions
Mevalonic acid + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPHdetails
Mevalonic acid + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPH + Hydrogen Iondetails
  Enzyme Details
5. Methylglutaconyl-CoA hydratase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of 3-methylglutaconyl-CoA to 3-hydroxy-3-methylglutaryl-CoA. Has very low enoyl-CoA hydratase activity. Was originally identified as RNA-binding protein that binds in vitro to clustered 5'-AUUUA-3' motifs.

Gene Name:
AUH
Uniprot ID:
Q13825  
Molecular weight:
35608.18
Reactions
3-Hydroxy-3-methylglutaryl-CoA → 3-Methylglutaconyl-CoA + Waterdetails
3-Hydroxy-3-methylglutaryl-CoA → 3-Methylglutaconyl-CoA + Waterdetails
  Enzyme Details
6. 3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic
General function:
Involved in catalytic activity
Specific function:
Non-mitochondrial 3-hydroxymethyl-3-methylglutaryl-CoA lyase that catalyzes a cation-dependent cleavage of (S)-3-hydroxy-3-methylglutaryl-CoA into acetyl-CoA and acetoacetate, a key step in ketogenesis, the products of which support energy production in nonhepatic animal tissues.

Gene Name:
HMGCLL1
Uniprot ID:
Q8TB92  
Molecular weight:
36327.465
Reactions
3-Hydroxy-3-methylglutaryl-CoA → Acetyl-CoA + Acetoacetic aciddetails