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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0000995

Secondary Accession Numbers

HMDB00995

Metabolite Identification

Common Name

16-Dehydroprogesterone

Description

16-Dehydroprogesterone, also known as delta.16-progesterone, belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton. Thus, 16-dehydroprogesterone is considered to be a steroid lipid molecule. 16-Dehydroprogesterone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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


  Mrv1652305261923522D          

 26 29  0  0  0  0            999 V2000
   -0.3804   -0.1956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3341   -0.6080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0915   -0.6115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3662    0.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524   -0.1885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3448   -1.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -1.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1377    0.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306    1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559    0.6435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4887   -0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3733   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5064   -0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    1.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0346    1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    0.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5064   -1.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7812    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2068   -1.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0772    2.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4816    2.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -1.0026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3412    0.2595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524   -0.9955    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 15  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  1  0  0  0
 12 18  1  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
  7 13  1  0  0  0  0
 10 11  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  2  0  0  0  0
  1 24  1  6  0  0  0
  2 25  1  1  0  0  0
  5 26  1  6  0  0  0
M  END

HMDB0000995
     RDKit          3D
16-Dehydroprogesterone
 51 54  0  0  0  0  0  0  0  0999 V2000
    4.7118    1.8178   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    0.4220   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -0.0618   -0.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -0.4254   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.6868   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142   -2.2726   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.0379   -0.7659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0508   -1.0664   -0.1369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9280   -2.2072   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -2.1560    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311   -0.8445   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424   -0.8396   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9111    0.3500   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815    0.3177   -0.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1960    1.6240   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7729    1.3322   -1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    0.4065   -0.1580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1556    1.1445    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697    0.2827   -0.5401 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1589    1.3886    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378    1.2897   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -0.0579    0.0497 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0488   -0.3749    1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462    1.8663    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965    2.1271    0.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    2.5239   -0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201   -2.2081   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -2.9408   -1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832   -2.8377    0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -0.6599   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -1.0556    0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -2.0026   -1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816   -3.1433   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -2.1337    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497   -2.9901    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6925   -1.7844   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6756    2.1686   -1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2218    2.2595    0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7764    0.8763   -2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    2.3001   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.6177    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2157    1.0869    1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8994    2.2136    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796    0.3126   -1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452    1.5512    1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1936    2.3435   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    1.4749   -1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1165    2.0698    0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2878    0.2323    2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543   -0.1774    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -1.4353    1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  6
  8 31  1  1
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  6
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END


  Mrv1652305261923522D          

 26 29  0  0  0  0            999 V2000
   -0.3804   -0.1956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3341   -0.6080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0915   -0.6115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3662    0.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524   -0.1885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3448   -1.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -1.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1377    0.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306    1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559    0.6435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4887   -0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3733   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5064   -0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    1.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0346    1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    0.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5064   -1.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7812    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2068   -1.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0772    2.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4816    2.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -1.0026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3412    0.2595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524   -0.9955    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 15  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  1  0  0  0
 12 18  1  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
  7 13  1  0  0  0  0
 10 11  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  2  0  0  0  0
  1 24  1  6  0  0  0
  2 25  1  1  0  0  0
  5 26  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000995

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h6,12,16,18-19H,4-5,7-11H2,1-3H3/t16-,18-,19-,20-,21+/m0/s1

> <INCHI_KEY>
VRRHHTISESGZFN-RKFFNLMFSA-N

> <FORMULA>
C21H28O2

> <MOLECULAR_WEIGHT>
312.4458

> <EXACT_MASS>
312.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.76985950027387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.998992101333335

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.742459518430817

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.978722918838034

> <JCHEM_PKA_STRONGEST_BASIC>
-4.564489189297514

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
93.58119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000995
     RDKit          3D
16-Dehydroprogesterone
 51 54  0  0  0  0  0  0  0  0999 V2000
    4.7118    1.8178   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    0.4220   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -0.0618   -0.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -0.4254   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.6868   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142   -2.2726   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.0379   -0.7659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0508   -1.0664   -0.1369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9280   -2.2072   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -2.1560    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311   -0.8445   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424   -0.8396   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9111    0.3500   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815    0.3177   -0.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1960    1.6240   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7729    1.3322   -1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    0.4065   -0.1580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1556    1.1445    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697    0.2827   -0.5401 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1589    1.3886    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378    1.2897   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -0.0579    0.0497 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0488   -0.3749    1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462    1.8663    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965    2.1271    0.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    2.5239   -0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201   -2.2081   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -2.9408   -1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832   -2.8377    0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -0.6599   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -1.0556    0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -2.0026   -1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816   -3.1433   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -2.1337    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497   -2.9901    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6925   -1.7844   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6756    2.1686   -1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2218    2.2595    0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7764    0.8763   -2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    2.3001   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.6177    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2157    1.0869    1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8994    2.2136    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796    0.3126   -1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452    1.5512    1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1936    2.3435   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    1.4749   -1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1165    2.0698    0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2878    0.2323    2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543   -0.1774    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -1.4353    1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  6
  8 31  1  1
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  6
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.710  -0.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.624  -1.135   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.037  -1.141   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.684   1.214   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.964  -0.352   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.644  -2.661   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.037  -2.675   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.358  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.124   0.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.617   1.971   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.971   1.201   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.646  -0.365   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.697  -3.438   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.358  -3.445   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.679  -1.141   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.318   1.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.931   3.026   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.652   1.188   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.679  -2.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.325   3.484   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.986  -3.424   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.011   4.241   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.632   4.234   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.717  -1.872   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.637   0.484   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.964  -1.858   0.000  0.00  0.00           H+0
CONECT    1    2    3    4   24                                             
CONECT    2    1    5    6   25                                             
CONECT    3    1    7    8    9                                             
CONECT    4    1   10                                                       
CONECT    5    2   11   12   26                                             
CONECT    6    2   13                                                       
CONECT    7    3   14   13                                                  
CONECT    8    3   15                                                       
CONECT    9    3                                                            
CONECT   10    4   11                                                       
CONECT   11    5   16   17   10                                             
CONECT   12    5   18                                                       
CONECT   13    6    7                                                       
CONECT   14    7   19                                                       
CONECT   15    8   19                                                       
CONECT   16   11   20   18                                                  
CONECT   17   11                                                            
CONECT   18   12   16                                                       
CONECT   19   14   21   15                                                  
CONECT   20   16   22   23                                                  
CONECT   21   19                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24    1                                                            
CONECT   25    2                                                            
CONECT   26    5                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0000995
HETATM    1  C1  UNL     1       4.712   1.818  -0.019  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.663   0.422  -0.461  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.762  -0.062  -0.912  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.478  -0.425  -0.422  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.472  -1.687  -0.825  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.114  -2.273  -0.657  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.283  -1.038  -0.766  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.051  -1.066  -0.137  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.928  -2.207  -0.589  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.174  -2.156   0.306  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.831  -0.845  -0.026  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.142  -0.840  -0.204  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.911   0.350  -0.528  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.181   0.318  -0.630  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.196   1.624  -0.744  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.773   1.332  -1.163  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.088   0.406  -0.158  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.156   1.144   1.182  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.670   0.283  -0.540  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.159   1.389   0.014  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.638   1.290  -0.298  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.148  -0.058   0.050  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.049  -0.375   1.525  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.346   1.866   1.050  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.797   2.127   0.065  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.191   2.524  -0.677  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.320  -2.208  -1.214  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.846  -2.941  -1.502  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.983  -2.838   0.261  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.280  -0.660  -1.792  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.022  -1.056   0.964  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.243  -2.003  -1.629  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.382  -3.143  -0.467  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.779  -2.134   1.356  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.850  -2.990   0.126  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.693  -1.784  -0.102  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.676   2.169  -1.574  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.222   2.259   0.174  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.776   0.876  -2.160  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.212   2.300  -1.122  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.555   0.618   1.946  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.216   1.087   1.529  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.899   2.214   1.072  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.580   0.313  -1.651  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.045   1.551   1.093  1.00  0.00           H  
HETATM   46  H23 UNL     1      -0.194   2.344  -0.474  1.00  0.00           H  
HETATM   47  H24 UNL     1       1.824   1.475  -1.368  1.00  0.00           H  
HETATM   48  H25 UNL     1       2.117   2.070   0.343  1.00  0.00           H  
HETATM   49  H26 UNL     1       1.288   0.232   2.044  1.00  0.00           H  
HETATM   50  H27 UNL     1       3.054  -0.177   1.966  1.00  0.00           H  
HETATM   51  H28 UNL     1       1.829  -1.435   1.732  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5    5   22
CONECT    5    6   27
CONECT    6    7   28   29
CONECT    7    8   22   30
CONECT    8    9   19   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   12   17
CONECT   12   13   36
CONECT   13   14   14   15
CONECT   15   16   37   38
CONECT   16   17   39   40
CONECT   17   18   19
CONECT   18   41   42   43
CONECT   19   20   44
CONECT   20   21   45   46
CONECT   21   22   47   48
CONECT   22   23
CONECT   23   49   50   51
END

HMDB0000995
     RDKit          3D
16-Dehydroprogesterone
 51 54  0  0  0  0  0  0  0  0999 V2000
    4.7118    1.8178   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    0.4220   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -0.0618   -0.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -0.4254   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.6868   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142   -2.2726   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.0379   -0.7659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0508   -1.0664   -0.1369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9280   -2.2072   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -2.1560    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311   -0.8445   -0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424   -0.8396   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9111    0.3500   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815    0.3177   -0.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1960    1.6240   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7729    1.3322   -1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    0.4065   -0.1580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1556    1.1445    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697    0.2827   -0.5401 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1589    1.3886    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378    1.2897   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -0.0579    0.0497 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0488   -0.3749    1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462    1.8663    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965    2.1271    0.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    2.5239   -0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201   -2.2081   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -2.9408   -1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832   -2.8377    0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -0.6599   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -1.0556    0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -2.0026   -1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816   -3.1433   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -2.1337    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497   -2.9901    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6925   -1.7844   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6756    2.1686   -1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2218    2.2595    0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7764    0.8763   -2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    2.3001   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.6177    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2157    1.0869    1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8994    2.2136    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796    0.3126   -1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452    1.5512    1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1936    2.3435   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    1.4749   -1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1165    2.0698    0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2878    0.2323    2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543   -0.1774    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -1.4353    1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  6
  8 31  1  1
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  6
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,20-Dioxopregna-4,16-diene	ChEBI
Delta(4,16)-Pregnadiene-3,20-dione	ChEBI
16,17-Didehydroprogesterone	Kegg
Δ(4,16)-pregnadiene-3,20-dione	Generator
4,16-Pregnadiene-3,20-dione	HMDB
D16-Progesterone	HMDB
D4,16-Pregnadiene-3,20-dione	HMDB
Delta.16-progesterone	HMDB
Delta4,16-Pregnadiene-3,20-dione	HMDB
Pregna-4,16-diene-3,20-dione	HMDB
delta(16)-Progesterone	HMDB
16-Dehydroprogesterone	ChEBI

Chemical Formula

C₂₁H₂₈O₂

Average Molecular Weight

312.4458

Monoisotopic Molecular Weight

312.20893014

IUPAC Name

(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one

Traditional Name

(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one

CAS Registry Number

1096-38-4

SMILES

[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h6,12,16,18-19H,4-5,7-11H2,1-3H3/t16-,18-,19-,20-,21+/m0/s1

InChI Key

VRRHHTISESGZFN-RKFFNLMFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

20-oxosteroids

Alternative Parents

Substituents

20-oxosteroid
Androgen-skeleton
Androstane-skeleton
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

enone (CHEBI:18204 )
3-oxo Delta(4)-steroid (CHEBI:18204 )
20-oxo steroid (CHEBI:18204 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030163 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000995)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000995)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000995)

Source

Endogenous

Endogenous (HMDB: HMDB0000995)

Animal

Animal (HMDB: HMDB0000995)

Exogenous

Food

Food (HMDB: HMDB0000995)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000995)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000995)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000995)

Lipid metabolism pathway (HMDB: HMDB0000995)

Cellular process

Cell signaling (HMDB: HMDB0000995)

Biochemical process

Lipid transport (HMDB: HMDB0000995)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000995)

Molecular messenger

Hormone (HMDB: HMDB0000995)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000995)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	185 - 187 °C	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	0.0097 g/L	ALOGPS
logP	3.8	ALOGPS
logP	4	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	18.98	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.58 m³·mol⁻¹	ChemAxon
Polarizability	36.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	177.124	31661259
DarkChem	[M-H]-	173.447	31661259
AllCCS	[M+H]+	179.293	32859911
AllCCS	[M-H]-	186.436	32859911
DeepCCS	[M-2H]-	210.907	30932474
DeepCCS	[M+Na]+	185.365	30932474
AllCCS	[M+H]+	179.3	32859911
AllCCS	[M+H-H2O]+	176.2	32859911
AllCCS	[M+NH4]+	182.1	32859911
AllCCS	[M+Na]+	182.9	32859911
AllCCS	[M-H]-	186.4	32859911
AllCCS	[M+Na-2H]-	186.7	32859911
AllCCS	[M+HCOO]-	187.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.98 minutes	32390414
Predicted by Siyang on May 30, 2022	18.8085 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2759.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	536.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	234.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	243.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	465.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	698.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	807.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1538.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	499.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1580.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	519.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	475.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	339.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	562.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16-Dehydroprogesterone	[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3823.0	Standard polar	33892256
16-Dehydroprogesterone	[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2641.7	Standard non polar	33892256
16-Dehydroprogesterone	[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2913.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16-Dehydroprogesterone,1TMS,isomer #1	CC(=O)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2840.6	Semi standard non polar	33892256
16-Dehydroprogesterone,1TMS,isomer #1	CC(=O)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2631.0	Standard non polar	33892256
16-Dehydroprogesterone,1TMS,isomer #1	CC(=O)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3101.5	Standard polar	33892256
16-Dehydroprogesterone,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2889.2	Semi standard non polar	33892256
16-Dehydroprogesterone,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2674.6	Standard non polar	33892256
16-Dehydroprogesterone,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3207.3	Standard polar	33892256
16-Dehydroprogesterone,2TMS,isomer #1	C=C(O[Si](C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2871.0	Semi standard non polar	33892256
16-Dehydroprogesterone,2TMS,isomer #1	C=C(O[Si](C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2738.4	Standard non polar	33892256
16-Dehydroprogesterone,2TMS,isomer #1	C=C(O[Si](C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3253.7	Standard polar	33892256
16-Dehydroprogesterone,1TBDMS,isomer #1	CC(=O)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3104.3	Semi standard non polar	33892256
16-Dehydroprogesterone,1TBDMS,isomer #1	CC(=O)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2861.7	Standard non polar	33892256
16-Dehydroprogesterone,1TBDMS,isomer #1	CC(=O)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3255.8	Standard polar	33892256
16-Dehydroprogesterone,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3137.8	Semi standard non polar	33892256
16-Dehydroprogesterone,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2917.4	Standard non polar	33892256
16-Dehydroprogesterone,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3357.9	Standard polar	33892256
16-Dehydroprogesterone,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3386.6	Semi standard non polar	33892256
16-Dehydroprogesterone,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3167.9	Standard non polar	33892256
16-Dehydroprogesterone,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3476.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Dehydroprogesterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-007k-0790000000-587e2010759d04be79da	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Dehydroprogesterone 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 - 16-Dehydroprogesterone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-03di-0009000000-70101cfe59fde51a8ff9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 16-Dehydroprogesterone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4j-5900000000-8c5e3f1358c9efe68931	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 16-Dehydroprogesterone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4j-9500000000-1fa651a1bfd23c37c15b	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 10V, Positive-QTOF	splash10-03di-0179000000-67a5fd6afc1237e6f0c5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 20V, Positive-QTOF	splash10-01vt-0391000000-73037a7fa24c2f096328	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 40V, Positive-QTOF	splash10-0f7a-2490000000-162c2aa3fd60d3279a3c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 10V, Negative-QTOF	splash10-03di-0019000000-f49571271662f7a5da14	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 20V, Negative-QTOF	splash10-03xr-0098000000-4d72f69ebbb13d5f7c4e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 40V, Negative-QTOF	splash10-0gbd-0090000000-4cd4d8acb44933c4d831	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 10V, Positive-QTOF	splash10-03di-0029000000-753e4d201cfb7cc7b807	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 20V, Positive-QTOF	splash10-01ow-1493000000-67e624229aa746721027	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 40V, Positive-QTOF	splash10-052f-7920000000-6f3d42fcb774cf571fa5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 10V, Negative-QTOF	splash10-03di-0009000000-152b659b4891e36b54f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 20V, Negative-QTOF	splash10-03di-0049000000-4d4a6f7ba007f9c34c62	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Dehydroprogesterone 40V, Negative-QTOF	splash10-07fu-0192000000-c9494d220d3973cd4385	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	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

FDB022357

KNApSAcK ID

Not Available

Chemspider ID

92118

KEGG Compound ID

C03207

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5926

PubChem Compound

101964

PDB ID

Not Available

ChEBI ID

18204

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Johnson, William S. Intermediates in total synthesis of 16-dehydroprogesterone. U.S. (1973), 15 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Schindler AE, Wuchter J: Studies on steroids in urine of the male newborn. Biol Neonate. 1975;27(3-4):192-207. [PubMed:126703 ]

Showing metabocard for 16-Dehydroprogesterone (HMDB0000995)

MOL for HMDB0000995 (16-Dehydroprogesterone)

3D MOL for HMDB0000995 (16-Dehydroprogesterone)

3D SDF for HMDB0000995 (16-Dehydroprogesterone)

3D-SDF for HMDB0000995 (16-Dehydroprogesterone)

PDB for HMDB0000995 (16-Dehydroprogesterone)

3D PDB for HMDB0000995 (16-Dehydroprogesterone)

SMILES for HMDB0000995 (16-Dehydroprogesterone)

INCHI for HMDB0000995 (16-Dehydroprogesterone)

Structure for HMDB0000995 (16-Dehydroprogesterone)

3D Structure for HMDB0000995 (16-Dehydroprogesterone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra