MiMeDB: Showing metabocard for 3-Hydroxy-3-methylglutaryl-CoA (MMDBc0033091)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:34:21 UTC

Update Date

2022-12-15 22:51:53 UTC

Metabolite ID

MMDBc0033091

Metabolite Identification

Common Name

3-Hydroxy-3-methylglutaryl-CoA

Description

3-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

MOL SDF PDB SMILES InChI

ChEBI
  Mrv0541 02241222322D          

 58 60  0  0  1  0            999 V2000
   29.2704   -9.6492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   28.6030   -9.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0155  -10.4338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.9355   -9.6492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.1905  -10.4338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.5004  -11.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5247  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2675  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8102  -14.1027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0958  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3813  -14.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8386  -12.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0958  -12.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8386  -11.6277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4097  -11.6277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1241  -11.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5531  -10.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4261   -9.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8386   -9.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2511   -9.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1241  -10.3901    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.4096   -9.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2675   -9.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9175   -9.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5675   -9.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0925   -9.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0925  -10.8026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7425   -9.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7425  -10.8026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0925   -9.9776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.7425   -9.9776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.1509   -9.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7055  -11.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8805  -11.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5305  -11.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7055  -11.9263    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.7055  -12.7513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0550   -9.3943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6682   -9.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3906   -8.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3826   -9.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6682  -10.7713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2111   -8.7268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0971   -9.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3827  -11.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0971  -10.7712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8115   -9.5337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9820  -13.6902    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.6965  -14.9277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6965  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4110  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8399  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5544  -14.9277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5544  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2689  -13.6902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5379  -14.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1254  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7129  -14.8172    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  0  0  0  0
 57 58  1  0  0  0  0
M  END

ChEBI
  Mrv0541 02241222322D          

 58 60  0  0  1  0            999 V2000
   29.2704   -9.6492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   28.6030   -9.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0155  -10.4338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.9355   -9.6492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.1905  -10.4338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.5004  -11.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5247  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2675  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8102  -14.1027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0958  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3813  -14.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8386  -12.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0958  -12.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8386  -11.6277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4097  -11.6277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1241  -11.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5531  -10.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4261   -9.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8386   -9.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2511   -9.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1241  -10.3901    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.4096   -9.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2675   -9.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9175   -9.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5675   -9.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0925   -9.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0925  -10.8026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7425   -9.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7425  -10.8026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0925   -9.9776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.7425   -9.9776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.1509   -9.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7055  -11.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8805  -11.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5305  -11.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7055  -11.9263    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.7055  -12.7513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0550   -9.3943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6682   -9.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3906   -8.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3826   -9.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6682  -10.7713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2111   -8.7268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0971   -9.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3827  -11.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0971  -10.7712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8115   -9.5337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9820  -13.6902    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.6965  -14.9277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6965  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4110  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8399  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5544  -14.9277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5544  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2689  -13.6902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5379  -14.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1254  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7129  -14.8172    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  0  0  0  0
 57 58  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033091

> <DATABASE_NAME>
MIME

> <SMILES>
CC(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-SJBCKIPMSA-N

> <FORMULA>
C27H44N7O20P3S

> <MOLECULAR_WEIGHT>
911.659

> <EXACT_MASS>
911.157467109

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
81.75063632923668

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
-7.502320448744017

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.8314326310000433

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8250358493029446

> <JCHEM_PKA_STRONGEST_BASIC>
5.001361103990641

> <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>
3-hydroxy-3-methylglutaryl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      54.638 -18.012   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      53.392 -17.107   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      54.162 -19.476   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      52.146 -18.012   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      52.622 -19.476   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      55.067 -20.722   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      42.046 -25.555   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.433 -26.325   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      40.712 -26.325   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      39.379 -25.555   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      38.045 -26.325   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      40.765 -23.245   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.379 -24.015   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      40.765 -21.705   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      38.098 -21.705   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      39.432 -20.935   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.099 -19.395   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.995 -17.291   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.765 -18.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.535 -17.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.432 -19.395   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      38.098 -18.625   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      43.433 -18.625   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      46.513 -18.625   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      49.593 -18.625   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      44.973 -17.085   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      44.973 -20.165   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      48.053 -17.085   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      48.053 -20.165   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      44.973 -18.625   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      48.053 -18.625   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      50.682 -17.536   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      51.717 -20.722   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      50.177 -22.262   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      53.257 -22.262   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      51.717 -22.262   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      51.717 -23.802   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      56.103 -17.536   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      57.247 -18.566   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      56.729 -16.129   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      58.581 -17.796   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      57.247 -20.106   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      58.261 -16.290   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      59.915 -18.566   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      58.581 -20.876   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      59.915 -20.106   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      61.248 -17.796   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      44.766 -25.555   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      46.100 -27.865   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      46.100 -26.325   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      47.434 -25.555   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      50.101 -25.555   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      51.435 -27.865   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      51.435 -26.325   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      52.769 -25.555   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      49.537 -27.659   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      48.767 -26.325   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      47.997 -27.659   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

Synonyms

Value	Source
(4-Carboxy-3-hydroxy-3-methylbutanoyl)-CoA	ChEBI
(4-Carboxy-3-hydroxy-3-methylbutanoyl)-coenzyme A	ChEBI
3-Hydroxy-3-methylglutaryl-coenzyme A	ChEBI

Molecular Formula

C₂₇H₄₄N₇O₂₀P₃S

Average Mass

911.659

Monoisotopic Mass

911.157467109

IUPAC Name

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 Name

3-hydroxy-3-methylglutaryl-coa

CAS Registry Number

1553-55-5

SMILES

CC(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-SJBCKIPMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-hydroxy-3-alkylglutaryl coas. These are alpha, omega dicarboxyacyl-CoA that result from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-alkylglutaric acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

3-hydroxy fatty acyl-CoA (CHEBI:11814 )
omega-carboxyacyl-CoA (CHEBI:11814 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.1 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-7.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	5	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	421.16 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	193.7 m³·mol⁻¹	ChemAxon
Polarizability	81.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0891000250-052d51ef28faa9ab5b73	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0971100000-dc16942c0a4531c8cb60	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1950000000-12dcb50a3caaf20a9aa5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00o4-4901031462-49fbf273ff8df18347bb	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900110010-0be1f0212b5d814ea24c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-fffa063c59d4fcd54e7a	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Adrenal Gland
Feces
Fibroblasts
Intestine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001446	Hydrogen Ion	Coenzyme A	3-hydroxy-3-methylglutaryl-coa reductase	Hydroxymethylglutaryl Coenzyme A Reductase (Ir)	VMH	2991281
MMDBr0001447	Acetoacetyl-CoA	Coenzyme A	3-hydroxy-3-methylglutaryl-coa synthase 1 (soluble)	Hydroxymethylglutaryl Coenzyme A Synthase (Ir)	VMH	1358203
MMDBr0001448	Acetoacetyl-CoA	Coenzyme A	3-hydroxy-3-methylglutaryl-coa synthase 2 (mitochondrial)	Hydroxymethylglutaryl Coenzyme A Synthase (Ir)	VMH	7893153
MMDBr0001449	3-Hydroxy-3-methylglutaryl-CoA	3-Hydroxy-3-methylglutaryl-CoA	Not Available	Hydroxymethylglutaryl Coenzyme A Reversible Mitochondrial Transport	VMH	14713247
MMDBr0001450	3-Hydroxy-3-methylglutaryl-CoA	3-Hydroxy-3-methylglutaryl-CoA	Not Available	Hydroxymethylglutaryl Coenzyme A Reversible Peroxisomal Transport	VMH	14713247
MMDBr0001451	3-Hydroxy-3-methylglutaryl-CoA	Acetoacetic acid	3-hydroxymethyl-3-methylglutaryl-coa lyase	Hydroxymethylglutaryl Coenzyme A Lyase	VMH	11129331
MMDBr0001452	3-Hydroxy-3-methylglutaryl-CoA	Acetoacetic acid	3-hydroxymethyl-3-methylglutaryl-coa lyase	Hydroxymethylglutaryl Coenzyme A Lyase	VMH	11111079
MMDBr0001651	3-Methylglutaconyl-CoA	3-Hydroxy-3-methylglutaryl-CoA	Au rna binding protein/enoyl-coa hydratase	Methylglutaconyl Coenzyme A Hydratase (Reversible), Mitochondrial	VMH	12434311 3082934
MMDBr0002566	Coenzyme A	Acetoacetyl-CoA	3-hydroxy-3-methylglutaryl-coa synthase 1 (soluble)	(S)-3-Hydroxy-3-Methylglutaryl Coenzyme A Acetoacetyl Coenzyme A-Lyase (Coa-Acetylating) Synthesis And Degradation of Ketone Bodies Valine, Leucine And Isoleucine Degradation	VMH	11087424 11108725 1358203 7893153
MMDBr0002572	Coenzyme A	Hydrogen Ion	Not Available	(R)-Mevalonate:NADP+ Oxidoreductase (Coa Acylating)	VMH	10698924 11108725 12454262 3745272 3883347
MMDBr0005488	Hydrogen Ion	Coenzyme A	3-hydroxy-3-methylglutaryl-coa reductase	Hydroxymethylglutaryl Coenzyme A Reductase (Ir) in Cytosol	VMH	30371894
MMDBr0007869	3-Hydroxy-3-methylglutaryl-CoA	Acetoacetic acid	Not Available	Hydroxymethylglutaryl-CoA lyase	VMH	30371894
MMDBr0008103	Coenzyme A	Acetoacetyl-CoA	Not Available	Hydroxymethylglutaryl CoA synthase	VMH	30371894
MMDBr0008330	3-Hydroxy-3-methylglutaryl-CoA	3-Methylglutaconyl-CoA	Not Available	(S)-3-Hydroxy-3-methylglutaryl-CoA hydro-lyase	VMH	30371894
MMDBr0008469	Hydrogen Ion	Coenzyme A	Not Available	Hydroxymethylglutaryl CoA reductase (ir)	VMH	30371894
MMDBr0008589	Water	3-Hydroxymethylglutaric acid	Not Available	Formation of 3-Hydroxy-3-Methyl-Glutarate	VMH	30371894
MMDBr0010292	Hydrogen Ion	Coenzyme A	3-hydroxy-3-methylglutaryl-coa reductase	(R)-Mevalonate:NADP+ Oxidoreductase (Coa Acylating)	VMH	30371894
MMDBr0019902	Water	Coenzyme A	Hydroxymethylglutaryl-CoA synthase	Synthesis	PathBank	31602464
MMDBr0019914	NADPH	Mevalonic acid	3-hydroxy-3-methylglutaryl-coenzyme A reductase 1	Reduction	PathBank	31602464
MMDBr0038803	3-Hydroxy-3-methylglutaryl-CoA	3-Hydroxymethylglutaric acid	Thioesterase TesA	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Proteobacteria	66	Human feces; Human sputum; Human ; Human unknown; Human pleural fluid plaque	Metabolic reconstruction
Bacteria	Firmicutes	211	Human feces; Human ; Human saliva; Pig ; Human subgingival plaque; Cattle	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	32	Human feces; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	10	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Fusobacteria	5	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Adrenal gland	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91506

PDB ID

Not Available

ChEBI ID

11814

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0009-8981(76)90353-3. [PubMed:947633 ]
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. doi: 10.1073/pnas.84.7.1863. [PubMed:3470763 ]
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. doi: 10.1016/s0006-291x(87)80508-9. [PubMed:3579907 ]
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. doi: 10.1042/bj2100523. [PubMed:6305342 ]
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. doi: 10.1515/bchm2.1983.364.1.135. [PubMed:6840702 ]
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Showing metabocard for 3-Hydroxy-3-methylglutaryl-CoA (MMDBc0033091)

MOL for #<Metabolite:0x00007fe29a62dd18>

3D MOL for #<Metabolite:0x00007fe29a62dd18>

3D SDF for #<Metabolite:0x00007fe29a62dd18>

3D-SDF for #<Metabolite:0x00007fe29a62dd18>

PDB for #<Metabolite:0x00007fe29a62dd18>

3D PDB for #<Metabolite:0x00007fe29a62dd18>

SMILES for #<Metabolite:0x00007fe29a62dd18>

INCHI for #<Metabolite:0x00007fe29a62dd18>

Structure for #<Metabolite:0x00007fe29a62dd18>

3D Structure for #<Metabolite:0x00007fe29a62dd18>