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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:51 UTC

Update Date

2022-03-07 02:49:15 UTC

HMDB ID

HMDB0002394

Secondary Accession Numbers

HMDB02394

Metabolite Identification

Common Name

Cholesta-4,6-dien-3-one

Description

Cholesta-4,6-dien-3-one is a product of the oxidation of cholesteral. It may be metabolized to 4-cholesten-3-one and cholestanol by liver, adrenals and brain. An accumulation of cholesta-4,6-dien-3-one is found in serum of patients with cerebrotendinous xanthomatosis, and it is possible that accumulation of cholesterol in these patients is secondary to accumulation of cholesta-4,6-dien-3-one (PMID: 3557306 ; 16757819; 3676336).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Untitled Document-11
  Mrv0541 02231219312D          

 31 34  0  0  0  0            999 V2000
   -3.4141   -1.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141   -2.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996   -3.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9852   -2.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9852   -1.7676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6996   -1.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -3.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -2.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -1.7676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2707   -1.3551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1582   -1.3551    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1582   -0.5301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5562   -0.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -0.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -1.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -0.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -0.2752    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1978    0.5095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0048    0.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597    1.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    2.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286    2.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    3.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9852   -0.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2445    0.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271   -2.3510    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -0.9426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718   -2.1520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    1.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286   -3.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  5 25  1  1  0  0  0
 12 26  1  1  0  0  0
  9 27  1  1  0  0  0
 10 28  1  6  0  0  0
 11 29  1  6  0  0  0
 18 30  1  6  0  0  0
  2 31  2  0  0  0  0
M  END

HMDB0002394
     RDKit          3D
Cholesta-4,6-dien-3-one
 70 73  0  0  0  0  0  0  0  0999 V2000
    7.0276   -0.3115    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1404   -1.2987   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9397    0.7898   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2375    0.7177   -1.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0007   -0.3696   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0115   -0.8357   -1.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5679   -0.9316    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1800   -0.4240    1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3085   -0.2710   -0.1066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3492   -1.5568   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9275    0.1373    0.3302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1328   -1.0037    0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -0.4491    1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0482    0.1395    0.4383 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4315   -0.8734   -0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1407   -0.5465    1.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5886    0.7211   -0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0286   -0.2622   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7083   -2.2228   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0020   -1.4087   -2.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4149    0.2958   -1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606   -0.7613   -2.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219   -1.9623    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2879   -2.3646   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8379    0.3491    1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9249    0.1734   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -1.6319    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4930   -1.0451    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4055    2.0974    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022    0.8503    3.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2081    1.9655    3.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078    1.7477    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460    2.9308    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    1.6001   -0.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2957    1.2448   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    2.8948   -1.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1151    1.9576    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -0.0439   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143    2.7124   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7167    1.4844   -1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
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 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
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 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
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  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
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 28 68  1  0
 28 69  1  0
 28 70  1  0
M  END

Untitled Document-11
  Mrv0541 02231219312D          

 31 34  0  0  0  0            999 V2000
   -3.4141   -1.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141   -2.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996   -3.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9852   -2.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9852   -0.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 31  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002394

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,17-19,22-25H,6-8,11-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
XIWMRKFKSRYSIJ-GYKMGIIDSA-N

> <FORMULA>
C27H42O

> <MOLECULAR_WEIGHT>
382.6218

> <EXACT_MASS>
382.323565966

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
49.21199077135376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

> <ALOGPS_LOGP>
6.31

> <JCHEM_LOGP>
7.318213321999998

> <ALOGPS_LOGS>
-7.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.938628620851844

> <JCHEM_PKA_STRONGEST_BASIC>
-4.773828935718656

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
120.68169999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.22e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cholesta-4,6-dien-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0002394
     RDKit          3D
Cholesta-4,6-dien-3-one
 70 73  0  0  0  0  0  0  0  0999 V2000
    7.0276   -0.3115    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1404   -1.2987   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7655   -0.7399   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9457   -1.5837    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1506   -0.2967    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9808   -0.6815    1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    0.3674    1.7465 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9193    1.3854    2.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970    1.0426    0.9341 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3903    1.8403   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155    1.8597   -1.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    1.2422   -0.2194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1376    0.7601   -0.8129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8438    1.8612   -1.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1584    1.8674   -1.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9397    0.7898   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2375    0.7177   -1.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0007   -0.3696   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0115   -0.8357   -1.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5679   -0.9316    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1800   -0.4240    1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3085   -0.2710   -0.1066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3492   -1.5568   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9275    0.1373    0.3302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1328   -1.0037    0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -0.4491    1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0482    0.1395    0.4383 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4315   -0.8734   -0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1407   -0.5465    1.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5886    0.7211   -0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0286   -0.2622   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7083   -2.2228   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0020   -1.4087   -2.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4149    0.2958   -1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606   -0.7613   -2.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219   -1.9623    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2879   -2.3646   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8379    0.3491    1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9249    0.1734   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -1.6319    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4930   -1.0451    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704   -0.1134    2.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4055    2.0974    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022    0.8503    3.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2081    1.9655    3.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078    1.7477    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460    2.9308    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    1.6001   -0.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2957    1.2448   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    2.8948   -1.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1151    1.9576    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -0.0439   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143    2.7124   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7177    2.6816   -2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7167    1.4844   -1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6311   -2.0289    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2571   -0.4943    1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7737   -1.1865    1.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2504    0.5766    1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8976   -2.3647   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9338   -1.4518   -1.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817   -1.9715   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0062    0.9165    1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455   -1.5602    1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7767   -1.7042    0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -1.2855    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636    0.3645    2.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086   -0.9638   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876   -1.8761   -0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4534   -0.6981   -0.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  6
 14 53  1  0
 15 54  1  0
 17 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  1
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-11                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.373  -3.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.373  -4.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.039  -5.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.706  -4.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.706  -3.300   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.039  -2.530   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.372  -5.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.038  -4.840   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.038  -3.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.372  -2.530   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.295  -2.530   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.295  -0.990   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.038  -0.220   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.372  -0.990   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.760  -3.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.665  -1.760   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.760  -0.514   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.236   0.951   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.742   1.271   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.218   2.736   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.725   3.056   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.200   4.521   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.707   4.841   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.111   5.610   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.706  -1.760   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.456   0.542   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       0.051  -4.389   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.038  -1.760   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.694  -4.017   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       1.147   2.040   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -7.707  -5.610   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   25                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   27                                             
CONECT   10    9    5   14   28                                             
CONECT   11    9   12   15   29                                             
CONECT   12   11   13   17   26                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    5                                                            
CONECT   26   12                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   18                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0002394
HETATM    1  C1  UNL     1       7.028  -0.311   0.035  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.140  -1.299  -0.695  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.765  -0.740  -2.044  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.946  -1.584   0.166  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.151  -0.297   0.448  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.981  -0.681   1.311  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.065   0.367   1.747  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.919   1.385   2.554  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.097   1.043   0.934  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.390   1.840  -0.252  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.115   1.860  -1.122  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.870   1.242  -0.219  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.138   0.760  -0.813  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.844   1.861  -1.466  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.158   1.867  -1.525  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.940   0.790  -0.946  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.238   0.718  -1.147  1.00  0.00           C  
HETATM   18  C18 UNL     1      -7.001  -0.370  -0.557  1.00  0.00           C  
HETATM   19  O1  UNL     1      -8.012  -0.836  -1.121  1.00  0.00           O  
HETATM   20  C19 UNL     1      -6.568  -0.932   0.736  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.180  -0.424   1.121  1.00  0.00           C  
HETATM   22  C21 UNL     1      -4.308  -0.271  -0.107  1.00  0.00           C  
HETATM   23  C22 UNL     1      -4.349  -1.557  -0.864  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.928   0.137   0.330  1.00  0.00           C  
HETATM   25  C24 UNL     1      -2.133  -1.004   0.898  1.00  0.00           C  
HETATM   26  C25 UNL     1      -0.867  -0.449   1.523  1.00  0.00           C  
HETATM   27  C26 UNL     1      -0.048   0.139   0.438  1.00  0.00           C  
HETATM   28  C27 UNL     1       0.431  -0.873  -0.533  1.00  0.00           C  
HETATM   29  H1  UNL     1       7.141  -0.546   1.102  1.00  0.00           H  
HETATM   30  H2  UNL     1       6.589   0.721  -0.085  1.00  0.00           H  
HETATM   31  H3  UNL     1       8.029  -0.262  -0.451  1.00  0.00           H  
HETATM   32  H4  UNL     1       6.708  -2.223  -0.811  1.00  0.00           H  
HETATM   33  H5  UNL     1       5.002  -1.409  -2.473  1.00  0.00           H  
HETATM   34  H6  UNL     1       5.415   0.296  -1.890  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.661  -0.761  -2.690  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.322  -1.962   1.139  1.00  0.00           H  
HETATM   37  H9  UNL     1       4.288  -2.365  -0.273  1.00  0.00           H  
HETATM   38  H10 UNL     1       4.838   0.349   1.027  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.925   0.173  -0.499  1.00  0.00           H  
HETATM   40  H12 UNL     1       2.505  -1.632   0.972  1.00  0.00           H  
HETATM   41  H13 UNL     1       3.493  -1.045   2.278  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.470  -0.113   2.624  1.00  0.00           H  
HETATM   43  H15 UNL     1       3.405   2.097   1.874  1.00  0.00           H  
HETATM   44  H16 UNL     1       3.602   0.850   3.223  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.208   1.966   3.181  1.00  0.00           H  
HETATM   46  H18 UNL     1       0.508   1.748   1.647  1.00  0.00           H  
HETATM   47  H19 UNL     1       1.546   2.931   0.032  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.204   1.600  -0.908  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.296   1.245  -2.048  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.157   2.895  -1.407  1.00  0.00           H  
HETATM   51  H23 UNL     1      -1.115   1.958   0.593  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.016  -0.044  -1.567  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.314   2.712  -1.926  1.00  0.00           H  
HETATM   54  H26 UNL     1      -4.718   2.682  -2.010  1.00  0.00           H  
HETATM   55  H27 UNL     1      -6.717   1.484  -1.760  1.00  0.00           H  
HETATM   56  H28 UNL     1      -6.631  -2.029   0.778  1.00  0.00           H  
HETATM   57  H29 UNL     1      -7.257  -0.494   1.516  1.00  0.00           H  
HETATM   58  H30 UNL     1      -4.774  -1.187   1.826  1.00  0.00           H  
HETATM   59  H31 UNL     1      -5.250   0.577   1.614  1.00  0.00           H  
HETATM   60  H32 UNL     1      -4.898  -2.365  -0.297  1.00  0.00           H  
HETATM   61  H33 UNL     1      -4.934  -1.452  -1.825  1.00  0.00           H  
HETATM   62  H34 UNL     1      -3.382  -1.971  -1.143  1.00  0.00           H  
HETATM   63  H35 UNL     1      -3.006   0.917   1.116  1.00  0.00           H  
HETATM   64  H36 UNL     1      -2.746  -1.560   1.634  1.00  0.00           H  
HETATM   65  H37 UNL     1      -1.777  -1.704   0.086  1.00  0.00           H  
HETATM   66  H38 UNL     1      -0.381  -1.285   2.062  1.00  0.00           H  
HETATM   67  H39 UNL     1      -1.164   0.364   2.239  1.00  0.00           H  
HETATM   68  H40 UNL     1      -0.209  -0.964  -1.441  1.00  0.00           H  
HETATM   69  H41 UNL     1       0.388  -1.876  -0.061  1.00  0.00           H  
HETATM   70  H42 UNL     1       1.453  -0.698  -0.931  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4   32
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    9   42
CONECT    8   43   44   45
CONECT    9   10   27   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   27   51
CONECT   13   14   24   52
CONECT   14   15   15   53
CONECT   15   16   54
CONECT   16   17   17   22
CONECT   17   18   55
CONECT   18   19   19   20
CONECT   20   21   56   57
CONECT   21   22   58   59
CONECT   22   23   24
CONECT   23   60   61   62
CONECT   24   25   63
CONECT   25   26   64   65
CONECT   26   27   66   67
CONECT   27   28
CONECT   28   68   69   70
END

HMDB0002394
     RDKit          3D
Cholesta-4,6-dien-3-one
 70 73  0  0  0  0  0  0  0  0999 V2000
    7.0276   -0.3115    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1404   -1.2987   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7655   -0.7399   -2.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9457   -1.5837    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1506   -0.2967    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9808   -0.6815    1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    0.3674    1.7465 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9193    1.3854    2.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970    1.0426    0.9341 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3903    1.8403   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155    1.8597   -1.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    1.2422   -0.2194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1376    0.7601   -0.8129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8438    1.8612   -1.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1584    1.8674   -1.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9397    0.7898   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2375    0.7177   -1.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0007   -0.3696   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0115   -0.8357   -1.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5679   -0.9316    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1800   -0.4240    1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3085   -0.2710   -0.1066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3492   -1.5568   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9275    0.1373    0.3302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1328   -1.0037    0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -0.4491    1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0482    0.1395    0.4383 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4315   -0.8734   -0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1407   -0.5465    1.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5886    0.7211   -0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0286   -0.2622   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7083   -2.2228   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0020   -1.4087   -2.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4149    0.2958   -1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606   -0.7613   -2.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219   -1.9623    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2879   -2.3646   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8379    0.3491    1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9249    0.1734   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -1.6319    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4930   -1.0451    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704   -0.1134    2.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4055    2.0974    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022    0.8503    3.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2081    1.9655    3.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078    1.7477    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460    2.9308    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    1.6001   -0.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2957    1.2448   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    2.8948   -1.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1151    1.9576    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -0.0439   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143    2.7124   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7177    2.6816   -2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7167    1.4844   -1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6311   -2.0289    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2571   -0.4943    1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7737   -1.1865    1.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2504    0.5766    1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8976   -2.3647   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9338   -1.4518   -1.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817   -1.9715   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0062    0.9165    1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455   -1.5602    1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7767   -1.7042    0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -1.2855    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636    0.3645    2.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086   -0.9638   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876   -1.8761   -0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4534   -0.6981   -0.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  6
 14 53  1  0
 15 54  1  0
 17 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  1
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,6-Cholestadien-3-one	HMDB, MeSH
4,6-Cholestadiene-3-one	HMDB
Cholest-4,6-dien-3-one	MeSH, HMDB
Cholesta-4,6-diene-3-one	MeSH, HMDB

Chemical Formula

C₂₇H₄₂O

Average Molecular Weight

382.6218

Monoisotopic Molecular Weight

382.323565966

IUPAC Name

(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

Traditional Name

cholesta-4,6-dien-3-one

CAS Registry Number

566-93-8

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,17-19,22-25H,6-8,11-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

XIWMRKFKSRYSIJ-GYKMGIIDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Oxosteroid
3-oxosteroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010059 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	208.318	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001242

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.2e-05 g/L	ALOGPS
logP	6.31	ALOGPS
logP	7.32	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	19.94	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.68 m³·mol⁻¹	ChemAxon
Polarizability	49.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	194.588	31661259
DarkChem	[M-H]-	192.516	31661259
DeepCCS	[M-2H]-	241.965	30932474
DeepCCS	[M+Na]+	217.824	30932474
AllCCS	[M+H]+	201.8	32859911
AllCCS	[M+H-H2O]+	199.6	32859911
AllCCS	[M+NH4]+	203.9	32859911
AllCCS	[M+Na]+	204.5	32859911
AllCCS	[M-H]-	204.3	32859911
AllCCS	[M+Na-2H]-	205.8	32859911
AllCCS	[M+HCOO]-	207.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cholesta-4,6-dien-3-one	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	3740.6	Standard polar	33892256
Cholesta-4,6-dien-3-one	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	3168.6	Standard non polar	33892256
Cholesta-4,6-dien-3-one	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	3300.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cholesta-4,6-dien-3-one,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3235.1	Semi standard non polar	33892256
Cholesta-4,6-dien-3-one,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3197.3	Standard non polar	33892256
Cholesta-4,6-dien-3-one,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3504.7	Standard polar	33892256
Cholesta-4,6-dien-3-one,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3476.4	Semi standard non polar	33892256
Cholesta-4,6-dien-3-one,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3386.4	Standard non polar	33892256
Cholesta-4,6-dien-3-one,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3642.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cholesta-4,6-dien-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-2239000000-553c810e1d19e3831e2b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholesta-4,6-dien-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Positive-QTOF	splash10-0bt9-0900000000-75bf7772949652267282	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Positive-QTOF	splash10-001i-0519000000-d3546c4987360df326ab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Positive-QTOF	splash10-001i-0009000000-17d134ad7478d2eabf41	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Positive-QTOF	splash10-001i-0019000000-976c7ec9b4ecd0f35ce1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Positive-QTOF	splash10-0api-3119000000-4c6c7aa38dc7223607b0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Positive-QTOF	splash10-0a4i-6239000000-e36074a482541cfecb97	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Negative-QTOF	splash10-001i-0009000000-ab162bbf77e93fdedda9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Negative-QTOF	splash10-001i-0009000000-8854ae94fc792ba973a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Negative-QTOF	splash10-0gba-2019000000-166d4a573bdfe5e55125	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Positive-QTOF	splash10-001i-0009000000-dcbeb6d0adb3f1962146	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Positive-QTOF	splash10-066r-6594000000-093e658315d31d30c0c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Positive-QTOF	splash10-0ab9-3921000000-1fa63eae5ed59c0d9041	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 10V, Negative-QTOF	splash10-001i-0009000000-334e990fc728bf944c79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 20V, Negative-QTOF	splash10-001i-0009000000-334e990fc728bf944c79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholesta-4,6-dien-3-one 40V, Negative-QTOF	splash10-001i-0049000000-c2d8d78e4aa615befe08	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022993

KNApSAcK ID

Not Available

Chemspider ID

2299095

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6663

PubChem Compound

3034666

PDB ID

Not Available

ChEBI ID

205734

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Parish, Edward J.; Sun, Hang; Lu, Ding; Kizito, Stephen A.; Qiu, Zhihai. New chemical syntheses of cholest-4,6-dien-3-one. Lipids (2002), 37(12), 1197-1200.

Material Safety Data Sheet (MSDS)

Not Available

General References

Buchmann MS, Bjorkhem I, Skrede S: Metabolism of the cholestanol precursor cholesta-4,6-dien-3-one in different tissues. Biochim Biophys Acta. 1987 Nov 21;922(2):111-7. [PubMed:3676336 ]
Bjorkhem I, Skrede S, Buchmann MS, East C, Grundy S: Accumulation of 7 alpha-hydroxy-4-cholesten-3-one and cholesta-4,6-dien-3-one in patients with cerebrotendinous xanthomatosis: effect of treatment with chenodeoxycholic acid. Hepatology. 1987 Mar-Apr;7(2):266-71. [PubMed:3557306 ]
Liu ZQ, Shan HY: Cholesterol, not polyunsaturated fatty acids, is target molecule in oxidation induced by reactive oxygen species in membrane of human erythrocytes. Cell Biochem Biophys. 2006;45(2):185-93. [PubMed:16757819 ]

Showing metabocard for Cholesta-4,6-dien-3-one (HMDB0002394)

MOL for HMDB0002394 (Cholesta-4,6-dien-3-one)

3D MOL for HMDB0002394 (Cholesta-4,6-dien-3-one)

3D SDF for HMDB0002394 (Cholesta-4,6-dien-3-one)

3D-SDF for HMDB0002394 (Cholesta-4,6-dien-3-one)

PDB for HMDB0002394 (Cholesta-4,6-dien-3-one)

3D PDB for HMDB0002394 (Cholesta-4,6-dien-3-one)

SMILES for HMDB0002394 (Cholesta-4,6-dien-3-one)

INCHI for HMDB0002394 (Cholesta-4,6-dien-3-one)

Structure for HMDB0002394 (Cholesta-4,6-dien-3-one)

3D Structure for HMDB0002394 (Cholesta-4,6-dien-3-one)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra