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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-02-03 10:00:23 UTC

Update Date

2022-03-07 02:51:12 UTC

HMDB ID

HMDB0011652

Secondary Accession Numbers

HMDB11652

Metabolite Identification

Common Name

11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid

Description

11b-hydroxy-3,20-dioxopregn-4-en-21-oic acid or HDOPA is a major metabolite of corticosterone that is typically elevated in the liver. The in vivo conversion of corticosterone to DHOPA and then to HDOPA is thought to proceed via the aldehyde intermediate 11b-hydroxy-3,20-dioxopregn-4-en-21-al. Cytochrome P450 3A4 (CYP3A4), is known to convert corticosterone to the gem-diol form of the aldehyde. Because CYP3A4 is highly abundant in the liver, the conversion of corticosterone to its aldehyde presumably occurs readily, and the formation of DHOPA by isomerization of the aldehyde. Subsequent dehydrogenation of DHOPA to HDOPA may be done by one of several liver specfici dehydrogenases. Possible candidates include aldehyde dehydrogenase type 3, lactate dehydrogenase A4, or 11b-hydroxysteroid dehydrogenase I. HDOPA has also been identified as a biomarker that is elevated (3700 X) in animals that have been treated with PPARalpha agonists. Peroxisome proliferator-activated receptor alpha (PPARalpha) is a nuclear receptor with manifold effects on intermediary metabolism (PMID: 17550978 ).

Structure

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


  Mrv0541 02241201492D          

 27 30  0  0  1  0            999 V2000
   14.3993   -2.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9220   -7.5925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2088   -5.1175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2088   -5.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9934   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4944   -6.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7798   -5.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4944   -4.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9934   -6.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4783   -5.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7798   -5.1175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0654   -6.3550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2484   -4.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3532   -4.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4944   -7.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0654   -7.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3509   -5.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6963   -3.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0654   -5.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7798   -7.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9513   -2.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6364   -6.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3509   -7.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6364   -7.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0553   -3.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0654   -4.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7583   -2.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  2  0  0  0  0
  2 24  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  3 14  1  1  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 19  1  1  0  0  0
 13 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 20  1  0  0  0  0
 16 23  2  0  0  0  0
 17 22  1  0  0  0  0
 18 21  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 11 26  1  1  0  0  0
 13 25  1  0  0  0  0
 27 21  1  0  0  0  0
M  END

HMDB0011652
     RDKit          3D
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid
 59 62  0  0  0  0  0  0  0  0999 V2000
    1.5921   -0.5555   -1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -0.4519   -0.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6361   -1.5713    0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8089   -1.5451   -0.0456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8759   -1.8506   -1.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425   -0.2384    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275    0.9393   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    2.2344    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3370    2.0370    1.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775    1.0788    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    1.2736    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5838    0.2699    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289    0.5639    0.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1565   -1.1395    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6840   -1.3245    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992   -0.1315    0.0888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2459    0.0908   -1.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6964    0.8618    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.8303   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024    1.1976   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223   -0.1795    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -1.2262    0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0052   -1.3228   -1.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9408   -1.1389    1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6573    0.1379    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6997    1.0375    1.7517 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473    0.4196   -0.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937   -0.2741   -2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.6084   -1.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284    0.0713   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -1.5583    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -2.5312   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200   -2.3497    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239   -2.6686   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714   -0.1142    1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    0.9235   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    2.8368   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243    2.9194    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459    1.7261    2.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    3.0017    1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0173    2.1761    1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6087   -1.7166   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6104   -1.6157    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -2.1792   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4014   -1.6374    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462   -0.3706   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2948   -0.2737   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502    1.1996   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    0.9387    1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643    2.8575   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6220    1.8344   -1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137    1.2442   -0.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    1.8171    0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -0.1279    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392   -2.2526    0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6380   -0.6301   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.2095    2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297   -2.0124    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3222    0.2870   -0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 27 59  1  0
M  END


  Mrv0541 02241201492D          

 27 30  0  0  1  0            999 V2000
   14.3993   -2.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9220   -7.5925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2088   -5.1175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2088   -5.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9934   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4944   -6.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7798   -5.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4944   -4.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9934   -6.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4783   -5.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7798   -5.1175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0654   -6.3550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2484   -4.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3532   -4.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4944   -7.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0654   -7.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3509   -5.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6963   -3.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0654   -5.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7798   -7.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9513   -2.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6364   -6.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3509   -7.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6364   -7.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0553   -3.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0654   -4.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7583   -2.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  2  0  0  0  0
  2 24  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  3 14  1  1  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 19  1  1  0  0  0
 13 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 20  1  0  0  0  0
 16 23  2  0  0  0  0
 17 22  1  0  0  0  0
 18 21  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 11 26  1  1  0  0  0
 13 25  1  0  0  0  0
 27 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011652

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O5/c1-21-8-7-13(23)9-12(21)3-4-14-15-5-6-16(17(24)10-19(26)27)22(15,2)11-18(25)20(14)21/h9,14-18,20,24-25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,17?,18-,20?,21-,22-/m0/s1

> <INCHI_KEY>
MSUMOHDXPKCNSB-ZUNXIJJCSA-N

> <FORMULA>
C22H32O5

> <MOLECULAR_WEIGHT>
376.4865

> <EXACT_MASS>
376.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.65950793047337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoic acid

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.9905268919999997

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.955646731416252

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.369656362907828

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2840874211345702

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
101.36129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011652
     RDKit          3D
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid
 59 62  0  0  0  0  0  0  0  0999 V2000
    1.5921   -0.5555   -1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -0.4519   -0.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6361   -1.5713    0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8089   -1.5451   -0.0456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8759   -1.8506   -1.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425   -0.2384    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275    0.9393   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    2.2344    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3370    2.0370    1.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775    1.0788    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    1.2736    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5838    0.2699    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289    0.5639    0.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1565   -1.1395    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6840   -1.3245    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992   -0.1315    0.0888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2459    0.0908   -1.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6964    0.8618    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.8303   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024    1.1976   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223   -0.1795    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -1.2262    0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0052   -1.3228   -1.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9408   -1.1389    1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6573    0.1379    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6997    1.0375    1.7517 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473    0.4196   -0.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937   -0.2741   -2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.6084   -1.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284    0.0713   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -1.5583    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -2.5312   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200   -2.3497    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239   -2.6686   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714   -0.1142    1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    0.9235   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    2.8368   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243    2.9194    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459    1.7261    2.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    3.0017    1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0173    2.1761    1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6087   -1.7166   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6104   -1.6157    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -2.1792   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4014   -1.6374    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462   -0.3706   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2948   -0.2737   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502    1.1996   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    0.9387    1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643    2.8575   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6220    1.8344   -1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137    1.2442   -0.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    1.8171    0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -0.1279    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392   -2.2526    0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6380   -0.6301   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.2095    2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297   -2.0124    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3222    0.2870   -0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 27 59  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      26.879  -3.859   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.521 -14.173   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      26.523  -9.553   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.523 -11.093   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.988  -9.077   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.190 -11.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.856 -11.093   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.190  -8.783   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.988 -11.568   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.893 -10.323   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.856  -9.553   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.522 -11.863   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.464  -7.612   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.793  -8.037   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.190 -13.403   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.522 -13.403   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.188 -11.093   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.433  -6.468   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.522 -10.323   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.856 -14.173   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.909  -5.003   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.855 -11.863   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.188 -14.173   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.855 -13.403   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      29.970  -7.292   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      22.522  -8.783   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      29.415  -4.683   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   24                                                            
CONECT    3    4    5    8   14                                             
CONECT    4    3    6    9                                                  
CONECT    5    3   10   13                                                  
CONECT    6    4    7   15                                                  
CONECT    7    6   11   12                                                  
CONECT    8    3   11                                                       
CONECT    9    4   10                                                       
CONECT   10    5    9                                                       
CONECT   11    7    8   26                                                  
CONECT   12    7   16   17   19                                             
CONECT   13    5   18   25                                                  
CONECT   14    3                                                            
CONECT   15    6   20                                                       
CONECT   16   12   20   23                                                  
CONECT   17   12   22                                                       
CONECT   18   13   21                                                       
CONECT   19   12                                                            
CONECT   20   15   16                                                       
CONECT   21    1   18   27                                                  
CONECT   22   17   24                                                       
CONECT   23   16   24                                                       
CONECT   24    2   22   23                                                  
CONECT   25   13                                                            
CONECT   26   11                                                            
CONECT   27   21                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0011652
HETATM    1  C1  UNL     1       1.592  -0.555  -1.705  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.378  -0.452  -0.242  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.636  -1.571   0.377  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.809  -1.545  -0.046  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.876  -1.851  -1.379  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.443  -0.238   0.329  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.728   0.939  -0.319  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.301   2.234   0.181  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.337   2.037   1.258  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.378   1.079   0.803  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.660   1.274   1.007  1.00  0.00           C  
HETATM   12  C11 UNL     1      -5.584   0.270   0.518  1.00  0.00           C  
HETATM   13  O2  UNL     1      -6.729   0.564   0.107  1.00  0.00           O  
HETATM   14  C12 UNL     1      -5.157  -1.139   0.511  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.684  -1.325   0.570  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.899  -0.131   0.089  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.246   0.091  -1.378  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.696   0.862   0.150  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.646   1.830  -0.452  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.002   1.198  -0.069  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.722  -0.180   0.435  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.725  -1.226   0.140  1.00  0.00           C  
HETATM   23  O3  UNL     1       4.005  -1.323  -1.203  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.941  -1.139   1.004  1.00  0.00           C  
HETATM   25  C22 UNL     1       5.657   0.138   0.862  1.00  0.00           C  
HETATM   26  O4  UNL     1       5.700   1.038   1.752  1.00  0.00           O  
HETATM   27  O5  UNL     1       6.347   0.420  -0.307  1.00  0.00           O  
HETATM   28  H1  UNL     1       0.694  -0.274  -2.309  1.00  0.00           H  
HETATM   29  H2  UNL     1       1.841  -1.608  -1.965  1.00  0.00           H  
HETATM   30  H3  UNL     1       2.428   0.071  -2.068  1.00  0.00           H  
HETATM   31  H4  UNL     1       0.770  -1.558   1.479  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.066  -2.531  -0.037  1.00  0.00           H  
HETATM   33  H6  UNL     1      -1.320  -2.350   0.526  1.00  0.00           H  
HETATM   34  H7  UNL     1      -1.424  -2.669  -1.543  1.00  0.00           H  
HETATM   35  H8  UNL     1      -1.271  -0.114   1.436  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.817   0.923  -1.409  1.00  0.00           H  
HETATM   37  H10 UNL     1      -1.782   2.837  -0.639  1.00  0.00           H  
HETATM   38  H11 UNL     1      -0.524   2.919   0.602  1.00  0.00           H  
HETATM   39  H12 UNL     1      -1.846   1.726   2.204  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.831   3.002   1.443  1.00  0.00           H  
HETATM   41  H14 UNL     1      -5.017   2.176   1.533  1.00  0.00           H  
HETATM   42  H15 UNL     1      -5.609  -1.717  -0.333  1.00  0.00           H  
HETATM   43  H16 UNL     1      -5.610  -1.616   1.430  1.00  0.00           H  
HETATM   44  H17 UNL     1      -3.419  -2.179  -0.114  1.00  0.00           H  
HETATM   45  H18 UNL     1      -3.401  -1.637   1.591  1.00  0.00           H  
HETATM   46  H19 UNL     1      -2.546  -0.371  -2.068  1.00  0.00           H  
HETATM   47  H20 UNL     1      -4.295  -0.274  -1.514  1.00  0.00           H  
HETATM   48  H21 UNL     1      -3.250   1.200  -1.600  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.724   0.939   1.237  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.564   2.857  -0.035  1.00  0.00           H  
HETATM   51  H24 UNL     1       1.622   1.834  -1.556  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.714   1.244  -0.915  1.00  0.00           H  
HETATM   53  H26 UNL     1       3.358   1.817   0.814  1.00  0.00           H  
HETATM   54  H27 UNL     1       2.467  -0.128   1.531  1.00  0.00           H  
HETATM   55  H28 UNL     1       3.239  -2.253   0.405  1.00  0.00           H  
HETATM   56  H29 UNL     1       4.638  -0.630  -1.481  1.00  0.00           H  
HETATM   57  H30 UNL     1       4.667  -1.210   2.100  1.00  0.00           H  
HETATM   58  H31 UNL     1       5.630  -2.012   0.849  1.00  0.00           H  
HETATM   59  H32 UNL     1       7.322   0.287  -0.453  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   18   21
CONECT    3    4   31   32
CONECT    4    5    6   33
CONECT    5   34
CONECT    6    7   16   35
CONECT    7    8   18   36
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   11   16
CONECT   11   12   41
CONECT   12   13   13   14
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17
CONECT   17   46   47   48
CONECT   18   19   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54
CONECT   22   23   24   55
CONECT   23   56
CONECT   24   25   57   58
CONECT   25   26   26   27
CONECT   27   59
END

HMDB0011652
     RDKit          3D
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid
 59 62  0  0  0  0  0  0  0  0999 V2000
    1.5921   -0.5555   -1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -0.4519   -0.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6361   -1.5713    0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8089   -1.5451   -0.0456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8759   -1.8506   -1.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425   -0.2384    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275    0.9393   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    2.2344    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3370    2.0370    1.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775    1.0788    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    1.2736    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5838    0.2699    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289    0.5639    0.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1565   -1.1395    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6840   -1.3245    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992   -0.1315    0.0888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2459    0.0908   -1.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6964    0.8618    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.8303   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024    1.1976   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223   -0.1795    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -1.2262    0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0052   -1.3228   -1.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9408   -1.1389    1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6573    0.1379    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6997    1.0375    1.7517 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473    0.4196   -0.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937   -0.2741   -2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.6084   -1.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284    0.0713   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -1.5583    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -2.5312   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200   -2.3497    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239   -2.6686   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714   -0.1142    1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    0.9235   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    2.8368   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243    2.9194    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459    1.7261    2.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    3.0017    1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0173    2.1761    1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6087   -1.7166   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6104   -1.6157    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -2.1792   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4014   -1.6374    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462   -0.3706   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2948   -0.2737   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502    1.1996   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    0.9387    1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643    2.8575   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6220    1.8344   -1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137    1.2442   -0.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    1.8171    0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -0.1279    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392   -2.2526    0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6380   -0.6301   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.2095    2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297   -2.0124    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3222    0.2870   -0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 27 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11b-Hydroxy-3,20-dioxopregn-4-en-21-Oate	Generator
11b-Hydroxy-3,20-dioxopregn-4-en-21-Oic acid	Generator
11beta-Hydroxy-3,20-dioxopregn-4-en-21-Oate	Generator
11Β-hydroxy-3,20-dioxopregn-4-en-21-Oate	Generator
11Β-hydroxy-3,20-dioxopregn-4-en-21-Oic acid	Generator
11beta-Hydroxy-3,20-dioxopregn-4-en-21-Oic acid	HMDB
HDOPA	HMDB
3-Hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoate	Generator

Chemical Formula

C₂₂H₃₂O₅

Average Molecular Weight

376.4865

Monoisotopic Molecular Weight

376.224974134

IUPAC Name

3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoic acid

Traditional Name

3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O

InChI Identifier

InChI=1S/C22H32O5/c1-21-8-7-13(23)9-12(21)3-4-14-15-5-6-16(17(24)10-19(26)27)22(15,2)11-18(25)20(14)21/h9,14-18,20,24-25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,17?,18-,20?,21-,22-/m0/s1

InChI Key

MSUMOHDXPKCNSB-ZUNXIJJCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

20-hydroxysteroid
Androgen-skeleton
Steroid acid
3-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	1.67	ALOGPS
logP	1.99	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.37	ChemAxon
pKa (Strongest Basic)	-0.28	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.36 m³·mol⁻¹	ChemAxon
Polarizability	41.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	187.877	31661259
DarkChem	[M-H]-	182.572	31661259
DeepCCS	[M-2H]-	224.465	30932474
DeepCCS	[M+Na]+	199.693	30932474
AllCCS	[M+H]+	194.5	32859911
AllCCS	[M+H-H2O]+	192.0	32859911
AllCCS	[M+NH4]+	196.7	32859911
AllCCS	[M+Na]+	197.4	32859911
AllCCS	[M-H]-	195.2	32859911
AllCCS	[M+Na-2H]-	196.0	32859911
AllCCS	[M+HCOO]-	196.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid	C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O	4514.7	Standard polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid	C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O	2977.5	Standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid	C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O	3582.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,1TMS,isomer #1	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(=O)CC[C@@]43C)C1CCC2C(O)CC(=O)O	3449.2	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,1TMS,isomer #2	C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@@]43C)C1CCC2C(CC(=O)O)O[Si](C)(C)C	3473.0	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,1TMS,isomer #3	C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@@]43C)C1CCC2C(O)CC(=O)O[Si](C)(C)C	3464.5	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,1TMS,isomer #4	C[C@]12C[C@H](O)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(O)CC(=O)O	3419.3	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TMS,isomer #1	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(=O)CC[C@@]43C)C1CCC2C(CC(=O)O)O[Si](C)(C)C	3385.7	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TMS,isomer #2	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(=O)CC[C@@]43C)C1CCC2C(O)CC(=O)O[Si](C)(C)C	3421.7	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TMS,isomer #3	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(O)CC(=O)O	3339.7	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TMS,isomer #4	C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@@]43C)C1CCC2C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3415.6	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TMS,isomer #5	C[C@]12C[C@H](O)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(CC(=O)O)O[Si](C)(C)C	3363.9	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TMS,isomer #6	C[C@]12C[C@H](O)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(O)CC(=O)O[Si](C)(C)C	3382.0	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,3TMS,isomer #1	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(=O)CC[C@@]43C)C1CCC2C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3368.1	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,3TMS,isomer #2	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(CC(=O)O)O[Si](C)(C)C	3266.4	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,3TMS,isomer #3	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(O)CC(=O)O[Si](C)(C)C	3279.1	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,3TMS,isomer #4	C[C@]12C[C@H](O)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3273.5	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,4TMS,isomer #1	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3233.8	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,4TMS,isomer #1	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3360.0	Standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,4TMS,isomer #1	C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CCC2C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3679.6	Standard polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@]2(C)C(C(O)CC(=O)O)CCC2C2CCC3=CC(=O)CC[C@]3(C)C21	3705.0	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CC(=O)O)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3[C@@H](O)C[C@]12C	3732.1	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC(O)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3[C@@H](O)C[C@]12C	3734.3	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CCC(C(O)CC(=O)O)[C@@]3(C)C[C@H](O)C12	3680.3	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CC(=O)O)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3851.2	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(O)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3880.7	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CCC(C(O)CC(=O)O)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)C12	3781.5	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3[C@@H](O)C[C@]12C	3924.8	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CCC(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O)C12	3859.0	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)CC(O)C1CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3[C@@H](O)C[C@]12C	3871.2	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	4024.9	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CCC(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)C12	3915.4	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC(O)C1CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3908.6	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3[C@@H](O)C[C@]12C	3969.3	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	4032.8	Semi standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	4185.0	Standard non polar	33892256
11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3928.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-2977000000-27268bc92fc1da6318e6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid GC-MS (3 TMS) - 70eV, Positive	splash10-004i-1222390000-2315ab9d57fe4b1f681c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 10V, Positive-QTOF	splash10-0a4l-0009000000-0be55a223dcf619eaae0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 20V, Positive-QTOF	splash10-052f-0129000000-414289ebfddf67823104	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 40V, Positive-QTOF	splash10-05mk-2294000000-148e328f6744f69fa40c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 10V, Negative-QTOF	splash10-056r-0009000000-ab9ab4fdc703478f4224	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 20V, Negative-QTOF	splash10-0bt9-1009000000-bf3af4253bf16f9d865a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 40V, Negative-QTOF	splash10-0a4u-9078000000-89ac73d149a47ed2d9d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 10V, Positive-QTOF	splash10-004i-0029000000-03104f89a8d4d9c813bb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 20V, Positive-QTOF	splash10-014r-1193000000-7ca203cc101cd5b2f299	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 40V, Positive-QTOF	splash10-02tc-7970000000-548e1ad3c19f451be943	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 10V, Negative-QTOF	splash10-004i-0009000000-363371b012935f191ffa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 20V, Negative-QTOF	splash10-0409-1029000000-712bfde25c75430d51a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 40V, Negative-QTOF	splash10-000f-8095000000-00d3a97b8f0768fd33e5	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB028343

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

53481012

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhen Y, Krausz KW, Chen C, Idle JR, Gonzalez FJ: Metabolomic and genetic analysis of biomarkers for peroxisome proliferator-activated receptor alpha expression and activation. Mol Endocrinol. 2007 Sep;21(9):2136-51. Epub 2007 Jun 5. [PubMed:17550978 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid (HMDB0011652)

MOL for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

3D MOL for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

3D SDF for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

3D-SDF for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

PDB for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

3D PDB for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

SMILES for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

INCHI for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

Structure for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

3D Structure for HMDB0011652 (11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra