NP-MRD: Showing NP-Card for 17alpha,21-Dihydroxypreg-nenolone (NP0087624)

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Record Information

Version

2.0

Created at

2022-05-11 16:55:06 UTC

Updated at

2022-05-11 16:55:07 UTC

NP-MRD ID

NP0087624

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17alpha,21-Dihydroxypreg-nenolone

Description

17Alpha,21-Dihydroxypregnenolone, also known as 3β,17,21-trihydroxy-pregn-5-en-20-one, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, 17alpha,21-dihydroxypregnenolone is considered to be a steroid lipid molecule. 17Alpha,21-Dihydroxypregnenolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 17Alpha,21-Dihydroxypregnenolone exists in all living organisms, ranging from bacteria to humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652311161719222D          

 28 31  0  0  0  0            999 V2000
 2501.0687 2501.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9312 2499.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7899 2497.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2498.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3563 2499.9979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7811 2501.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2502.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2100 2501.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0666 2502.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2501.2487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0687 2498.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2181 2499.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5036 2499.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5036 2498.3447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.2181 2497.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2499.5843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9291 2499.1718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.9291 2498.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2497.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3581 2498.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3581 2499.1718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.3555 2500.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6410 2500.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0700 2499.5930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.0700 2500.4181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.7811 2500.8314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2502.4956 2499.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2500.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 24 25  1  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 26  6  1  0  0  0  0
 26 10  1  6  0  0  0
 26 25  1  0  0  0  0
 24 27  1  0  0  0  0
 24 11  1  6  0  0  0
 25  1  1  1  0  0  0
 14  3  1  1  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 23 16  1  0  0  0  0
 21 24  1  0  0  0  0
 16  4  1  6  0  0  0
 21  5  1  1  0  0  0
 17  2  1  1  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -1.6822   -1.9576   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231   -0.4914   -0.1632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4852    0.3430   -1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248    0.0276   -1.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556    0.4963   -0.3819 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3031   -0.0641    0.9247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9160    0.7789    2.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455    1.3240    1.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8602    1.0981    0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1809    1.6722    0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0118    0.7539   -0.6412 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3418   -0.3597    0.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705    0.4062   -1.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959    0.6610   -1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2467    0.2239   -0.5095 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4785   -1.2315   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772    0.0514    1.0677 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8137   -0.7446    2.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868   -0.8035    1.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3332   -0.2164    0.3049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4460    1.1694    0.4805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3828   -0.7678   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4216   -1.9505   -0.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4227    0.1146   -1.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3349   -0.6056   -1.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151   -2.2323   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7119   -2.3049    0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4474   -2.4944    0.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060    1.4150   -0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077    0.2498   -2.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761    0.6575   -2.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1382   -1.0152   -1.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6551    1.6047   -0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895   -1.1038    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2510    1.6569    2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286    0.2166    2.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    1.9703    2.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613    2.6257   -0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7267    1.9976    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750    1.2580   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2416   -0.6535   -0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7303    0.9420   -2.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5168   -0.6731   -2.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3275    0.0398   -2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454    1.7464   -2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2275   -1.7010   -0.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547   -1.4896    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -1.7720   -0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256    1.1097    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4006   -1.7666    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7238   -0.2253    3.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7032   -1.8074    1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8785   -0.1425    2.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2171    1.2969    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9050    0.8862   -1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9066    0.6589   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1092   -0.8781   -1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 20  2  1  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  2 17  1  0
 15  5  1  0
  6 17  1  0
 15  9  1  0
 17 49  1  1
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 21 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  1
  6 34  1  1
  7 35  1  0
  7 36  1  0
  8 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
M  END

  Mrv1652311161719222D          

 28 31  0  0  0  0            999 V2000
 2501.0687 2501.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9312 2499.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7899 2497.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2498.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3563 2499.9979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7811 2501.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2502.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2100 2501.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0666 2502.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2501.2487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0687 2498.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2181 2499.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5036 2499.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5036 2498.3447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.2181 2497.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2499.5843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9291 2499.1718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.9291 2498.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2497.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3581 2498.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3581 2499.1718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.3555 2500.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6410 2500.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0700 2499.5930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.0700 2500.4181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.7811 2500.8314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2502.4956 2499.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2500.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 24 25  1  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 26  6  1  0  0  0  0
 26 10  1  6  0  0  0
 26 25  1  0  0  0  0
 24 27  1  0  0  0  0
 24 11  1  6  0  0  0
 25  1  1  1  0  0  0
 14  3  1  1  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 23 16  1  0  0  0  0
 21 24  1  0  0  0  0
 16  4  1  6  0  0  0
 21  5  1  1  0  0  0
 17  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0087624

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1

> <INCHI_KEY>
JNHJGXQUDOYJAK-IYRCEVNGSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.4764

> <EXACT_MASS>
348.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.63040943997079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethan-1-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.016685283666667

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.905650428318339

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.591023870838399

> <JCHEM_PKA_STRONGEST_BASIC>
-1.397243740261139

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
96.85889999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-NOV-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-NOV-17         0                                  
HETATM    1  C   UNK     0    4668.6624668.994   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4664.6724666.663   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    4660.6744662.803   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    4666.0014664.358   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    4667.3324666.663   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    4669.9914669.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4671.3254670.538   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4672.6594669.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4668.6584670.538   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4671.3254668.998   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0    4668.6624664.358   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    4663.3404665.887   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4662.0074665.117   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4662.0074663.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4663.3404662.807   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4666.0014665.891   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4664.6684665.121   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4664.6684663.581   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4666.0014662.811   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4667.3354663.581   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4667.3354665.121   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    4667.3304668.217   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    4665.9974667.447   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    4668.6644665.907   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    4668.6644667.447   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    4669.9914668.219   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    4671.3254665.909   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    4671.3254667.449   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   17                                                            
CONECT    3   14                                                            
CONECT    4   16                                                            
CONECT    5   21                                                            
CONECT    6    7    9   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10   26                                                            
CONECT   11   24                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    3                                                  
CONECT   15   14   18                                                       
CONECT   16   17   21   23    4                                             
CONECT   17   16   18   12    2                                             
CONECT   18   17   19   15                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   16   20   24    5                                             
CONECT   22   23   25                                                       
CONECT   23   22   16                                                       
CONECT   24   25   27   11   21                                             
CONECT   25   22   24   26    1                                             
CONECT   26   28    6   10   25                                             
CONECT   27   28   24                                                       
CONECT   28   26   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
17a,21-Dihydroxypregnenolone	Generator
17Α,21-dihydroxypregnenolone	Generator
17alpha,21-Dihydroxypreg-nenolone	HMDB
17, 21-Dihydroxypregnenolone	HMDB
3Β,17α,21-trihydroxypregnenone	HMDB
3beta,17alpha,21-Trihydroxypregnenone	HMDB
17,21-Dihydroxypregnenolone	HMDB
3Β,17,21-trihydroxy-pregn-5-en-20-one	HMDB
3beta,17,21-Trihydroxy-pregn-5-en-20-one	HMDB
(3Β)-3,17,21-trihydroxypregn-5-en-20-one	HMDB
(3beta)-3,17,21-Trihydroxypregn-5-en-20-one	HMDB
3Β,17α,21-trihydroxypregn-5-en-20-one	HMDB
3beta,17alpha,21-Trihydroxypregn-5-en-20-one	HMDB
17alpha,21-Dihydroxypregnenolone	HMDB

Chemical Formula

C₂₁H₃₂O₄

Average Mass

348.4764 Da

Monoisotopic Mass

348.23006 Da

IUPAC Name

1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethan-1-one

Traditional Name

1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethanone

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1

InChI Key

JNHJGXQUDOYJAK-IYRCEVNGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
20-oxosteroid
Pregnane-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Oxosteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
17-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Tertiary alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:27832 )
17alpha-hydroxy steroid (CHEBI:27832 )
21-hydroxy steroid (CHEBI:27832 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030141 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.6	ALOGPS
logP	2.02	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.86 m³·mol⁻¹	ChemAxon
Polarizability	39.63 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

External Links

HMDB ID

HMDB0006762

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024065

KNApSAcK ID

Not Available

Chemspider ID

167253

KEGG Compound ID

C05487

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

192735

PDB ID

Not Available

ChEBI ID

27832

Good Scents ID

Not Available

References

General References

Showing NP-Card for 17alpha,21-Dihydroxypreg-nenolone (NP0087624)

MOL for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

3D MOL for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

3D SDF for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

3D-SDF for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

PDB for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

3D PDB for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

SMILES for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

INCHI for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

Structure for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)

3D Structure for NP0087624 (17alpha,21-Dihydroxypreg-nenolone)