NP-MRD: Showing NP-Card for Deoxycorticosterone (NP0000090)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:38:56 UTC

NP-MRD ID

NP0000090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deoxycorticosterone

Description

11-Deoxycorticosterone (also called desoxycortone, 21-hydroxyprogesterone, DOC, or simply deoxycorticosterone) is a steroid hormone produced by the adrenal gland that possesses mineralocorticoid activity and acts as a precursor to aldosterone. It is classified as a member of the 21-hydroxysteroids. 21-Hydroxysteroids are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Deoxycorticosterone is very hydrophobic, practically insoluble (in water), and relatively neutral. Deoxycorticosterone can be synthesized from progesterone by 21-beta-hydroxylase and is then converted to corticosterone by 11-beta-hydroxylase. Corticosterone is then converted to aldosterone by aldosterone synthase. Deoxycorticosterone stimulates the collecting tubules in the kidney to continue to excrete potassium in much the same way that aldosterone does. Deoxycorticosterone has about 1/20 of the sodium retaining power of aldosterone and about 1/5 the potassium excreting power of aldosterone (Wikipedia). Deoxycorticosterone can be found throughout all human tissues and has been detected in amniotic fluid and blood. When present in sufficiently high levels, deoxycorticosterone can act as a hypertensive agent and a metabotoxin. A hypertensive agent increases blood pressure and causes the production of more urine. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of deoxycorticosterone are associated with congenital adrenal hyperplasia (CAH) and with adrenal tumors producing deoxycorticosterone (PMID: 20671982 ). High levels of this mineralocorticoid are associated with resistant hypertension, which can result in polyuria, polydipsia, increased blood volume, edema, and cardiac enlargement. Deoxycorticosterone can be used to treat adrenal insufficiency. In particular, desoxycorticosterone acetate (DOCA) is used as replacement therapy in Addison's disease.

Structure

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


  Mrv1652303182019222D          

 27 30  0  0  0  0            999 V2000
10001.085210001.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.953410000.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8171 9997.9548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6642 9998.7859    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.375510000.0175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0852 9998.7859    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2420 9999.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5275 9999.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5275 9998.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2420 9997.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9509 9999.1923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9509 9998.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6654 9997.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3799 9998.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.375910000.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.661410000.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6614 9999.6107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3759 9999.1983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0904 9999.6107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.090410000.4358    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.8699 9999.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.354710000.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.869910000.6917    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.869910001.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.583410001.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.299010001.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.154210001.9291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 24 27  2  0  0  0  0
 25 26  1  0  0  0  0
 23 22  1  0  0  0  0
  9  3  2  0  0  0  0
  7 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11  2  1  1  0  0  0
 17 11  1  0  0  0  0
 14 18  1  0  0  0  0
 19 21  1  0  0  0  0
 23 20  1  0  0  0  0
 19  6  1  6  0  0  0
 20  1  1  1  0  0  0
 17  4  1  6  0  0  0
 18  5  1  1  0  0  0
M  END

HMDB0000016
     RDKit          3D
Deoxycorticosterone
 54 57  0  0  0  0  0  0  0  0999 V2000
    1.7911   -0.1685    1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792    0.2113    0.0873 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2010    1.5235   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498    1.4968   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9603    0.2752   -0.7247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2012   -0.9433   -0.1695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9750   -2.1569   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -2.1710    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -0.8669    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683   -0.8951    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.3584    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0137    0.5337    1.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5502    1.4384   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.2674   -1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3118    0.4355   -0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2591    1.2563    1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1441   -0.8005   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0308   -1.9705   -0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -1.2987   -1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    0.0806   -0.4189 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3545    0.1598    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0521   -0.8565    0.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674    1.3885    1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8386    2.4534    1.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6226   -1.2521    1.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714    0.1987    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146    0.3913    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8940    2.1199   -0.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657    2.0652    0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0669    1.8648   -1.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634    2.3230   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2167   -0.0534   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2299   -0.9251    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268   -2.1215   -1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206   -3.0687   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144   -2.9364   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -2.4822    1.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8077   -1.8400    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2764    1.5068   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6531    2.3980    0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    0.8145   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665    2.2749   -1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    1.1690    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597    2.3469    1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1416    0.9337    1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0929   -0.3965   -1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415   -2.6823   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -2.5338    0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3326   -1.1463   -2.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239   -1.8703   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    0.8689   -1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7280    1.6746    1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7729    1.2074    2.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518    2.9517    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  6
  6 33  1  1
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 23 52  1  0
 23 53  1  0
 24 54  1  0
M  END


  Mrv1652303182019222D          

 27 30  0  0  0  0            999 V2000
10001.085210001.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.953410000.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8171 9997.9548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6642 9998.7859    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.375510000.0175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0852 9998.7859    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2420 9999.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5275 9999.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5275 9998.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2420 9997.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9509 9999.1923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9509 9998.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6654 9997.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3799 9998.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.375910000.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.661410000.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6614 9999.6107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3759 9999.1983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0904 9999.6107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.090410000.4358    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.8699 9999.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.354710000.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.869910000.6917    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.869910001.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.583410001.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.299010001.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.154210001.9291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 24 27  2  0  0  0  0
 25 26  1  0  0  0  0
 23 22  1  0  0  0  0
  9  3  2  0  0  0  0
  7 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11  2  1  1  0  0  0
 17 11  1  0  0  0  0
 14 18  1  0  0  0  0
 19 21  1  0  0  0  0
 23 20  1  0  0  0  0
 19  6  1  6  0  0  0
 20  1  1  1  0  0  0
 17  4  1  6  0  0  0
 18  5  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0000090

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1

> <INCHI_KEY>
ZESRJSPZRDMNHY-YFWFAHHUSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.4611

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.18996451471434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.3313563546666676

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.087225406758208

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.864723909946662

> <JCHEM_PKA_STRONGEST_BASIC>
-3.295317874239208

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
94.40749999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000016
     RDKit          3D
Deoxycorticosterone
 54 57  0  0  0  0  0  0  0  0999 V2000
    1.7911   -0.1685    1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792    0.2113    0.0873 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2010    1.5235   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498    1.4968   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9603    0.2752   -0.7247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2012   -0.9433   -0.1695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9750   -2.1569   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -2.1710    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -0.8669    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683   -0.8951    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.3584    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0137    0.5337    1.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5502    1.4384   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.2674   -1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3118    0.4355   -0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2591    1.2563    1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1441   -0.8005   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0308   -1.9705   -0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -1.2987   -1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    0.0806   -0.4189 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3545    0.1598    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0521   -0.8565    0.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674    1.3885    1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8386    2.4534    1.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6226   -1.2521    1.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714    0.1987    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146    0.3913    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8940    2.1199   -0.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657    2.0652    0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0669    1.8648   -1.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634    2.3230   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2167   -0.0534   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2299   -0.9251    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268   -2.1215   -1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206   -3.0687   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144   -2.9364   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -2.4822    1.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8077   -1.8400    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2764    1.5068   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6531    2.3980    0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    0.8145   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665    2.2749   -1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    1.1690    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597    2.3469    1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1416    0.9337    1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0929   -0.3965   -1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415   -2.6823   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -2.5338    0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3326   -1.1463   -2.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239   -1.8703   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    0.8689   -1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7280    1.6746    1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7729    1.2074    2.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518    2.9517    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  6
  6 33  1  1
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 23 52  1  0
 23 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0    8668.6928669.027   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.7138666.699   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8660.7258662.849   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8666.0408664.400   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8667.3688666.699   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8668.6928664.400   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8663.3858665.929   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0518665.159   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.0518663.619   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3858662.849   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.7088665.159   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.7088663.619   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.0428662.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3768663.619   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.3688668.250   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.0358667.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.0358665.940   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.3688665.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.7028665.940   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.7028667.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.1578665.466   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.0628666.712   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.1578667.958   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8670.1578669.498   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.4898670.268   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8672.8258669.498   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0    8668.8218670.268   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   11                                                            
CONECT    3    9                                                            
CONECT    4   17                                                            
CONECT    5   18                                                            
CONECT    6   19                                                            
CONECT    7    8   11                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9   12                                                       
CONECT   11   12    7    2   17                                             
CONECT   12   11   13   10                                                  
CONECT   13   12   14                                                       
CONECT   14   13   18                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   11    4                                             
CONECT   18   17   19   14    5                                             
CONECT   19   18   20   21    6                                             
CONECT   20   15   19   23    1                                             
CONECT   21   22   19                                                       
CONECT   22   21   23                                                       
CONECT   23   24   22   20                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0000016
HETATM    1  C1  UNL     1       1.791  -0.169   1.533  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.879   0.211   0.087  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.201   1.524  -0.169  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.150   1.497  -0.771  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.960   0.275  -0.725  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.201  -0.943  -0.170  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.975  -2.157  -0.620  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.257  -2.171   0.199  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.964  -0.867   0.163  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.268  -0.895   0.347  1.00  0.00           C  
HETATM   11  C11 UNL     1      -5.001   0.358   0.320  1.00  0.00           C  
HETATM   12  O1  UNL     1      -6.014   0.534   1.039  1.00  0.00           O  
HETATM   13  C12 UNL     1      -4.550   1.438  -0.564  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.143   1.267  -1.049  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.312   0.435  -0.060  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.259   1.256   1.204  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.144  -0.801  -0.793  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.031  -1.970  -0.750  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.369  -1.299  -1.099  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.270   0.081  -0.419  1.00  0.00           C  
HETATM   21  C20 UNL     1       4.354   0.160   0.571  1.00  0.00           C  
HETATM   22  O2  UNL     1       5.052  -0.856   0.777  1.00  0.00           O  
HETATM   23  C21 UNL     1       4.667   1.388   1.343  1.00  0.00           C  
HETATM   24  O3  UNL     1       3.839   2.453   1.039  1.00  0.00           O  
HETATM   25  H1  UNL     1       1.623  -1.252   1.692  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.671   0.199   2.084  1.00  0.00           H  
HETATM   27  H3  UNL     1       0.915   0.391   1.973  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.894   2.120  -0.804  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.166   2.065   0.810  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.067   1.865  -1.840  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.763   2.323  -0.295  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.217  -0.053  -1.780  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.230  -0.925   0.922  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.227  -2.122  -1.692  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.421  -3.069  -0.404  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.914  -2.936  -0.228  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.024  -2.482   1.236  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.808  -1.840   0.520  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.276   1.507  -1.426  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.653   2.398   0.007  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.133   0.815  -2.059  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.666   2.275  -1.119  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.337   1.169   1.773  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.460   2.347   1.006  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.142   0.934   1.830  1.00  0.00           H  
HETATM   46  H22 UNL     1       1.093  -0.396  -1.802  1.00  0.00           H  
HETATM   47  H23 UNL     1       1.741  -2.682  -1.562  1.00  0.00           H  
HETATM   48  H24 UNL     1       2.084  -2.534   0.176  1.00  0.00           H  
HETATM   49  H25 UNL     1       3.333  -1.146  -2.196  1.00  0.00           H  
HETATM   50  H26 UNL     1       4.224  -1.870  -0.743  1.00  0.00           H  
HETATM   51  H27 UNL     1       3.398   0.869  -1.224  1.00  0.00           H  
HETATM   52  H28 UNL     1       5.728   1.675   1.037  1.00  0.00           H  
HETATM   53  H29 UNL     1       4.773   1.207   2.437  1.00  0.00           H  
HETATM   54  H30 UNL     1       4.152   2.952   0.238  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   17   20
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   15   32
CONECT    6    7   17   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   10   15
CONECT   10   11   38
CONECT   11   12   12   13
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16
CONECT   16   43   44   45
CONECT   17   18   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   51
CONECT   21   22   22   23
CONECT   23   24   52   53
CONECT   24   54
END

HMDB0000016
     RDKit          3D
Deoxycorticosterone
 54 57  0  0  0  0  0  0  0  0999 V2000
    1.7911   -0.1685    1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792    0.2113    0.0873 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2010    1.5235   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498    1.4968   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9603    0.2752   -0.7247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2012   -0.9433   -0.1695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9750   -2.1569   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -2.1710    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -0.8669    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683   -0.8951    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.3584    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0137    0.5337    1.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5502    1.4384   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.2674   -1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3118    0.4355   -0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2591    1.2563    1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1441   -0.8005   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0308   -1.9705   -0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -1.2987   -1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    0.0806   -0.4189 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3545    0.1598    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0521   -0.8565    0.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674    1.3885    1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8386    2.4534    1.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6226   -1.2521    1.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714    0.1987    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146    0.3913    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8940    2.1199   -0.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657    2.0652    0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0669    1.8648   -1.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634    2.3230   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2167   -0.0534   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2299   -0.9251    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268   -2.1215   -1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206   -3.0687   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144   -2.9364   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -2.4822    1.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8077   -1.8400    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2764    1.5068   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6531    2.3980    0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    0.8145   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665    2.2749   -1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    1.1690    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597    2.3469    1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1416    0.9337    1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0929   -0.3965   -1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415   -2.6823   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -2.5338    0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3326   -1.1463   -2.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239   -1.8703   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    0.8689   -1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7280    1.6746    1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7729    1.2074    2.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518    2.9517    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  6
  6 33  1  1
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 23 52  1  0
 23 53  1  0
 24 54  1  0
M  END

View in JSmol

Synonyms

Value	Source
21-Hydroxy-4-pregnene-3,20-dione	ChEBI
21-Hydroxyprogesterone	ChEBI
4-Pregnen-21-ol-3,20-dione	ChEBI
Cortexone	ChEBI
DESOXYCORTICOSTERONE	ChEBI
Desoxycortone	ChEBI
DOC	ChEBI
Kendall's desoxy compound b	ChEBI
Reichstein's substance Q	ChEBI
11-Dehydroxycorticosterone	HMDB
11-Deoxy-corticosterone	HMDB
11-Deoxycorticosterone	HMDB
11-Desoxycorticosterone	HMDB
21-Hydroxy-3,20-dioxopregn-4-ene	HMDB
21-Hydroxy-D4-pregnane-3,20-dione	HMDB
21-Hydroxy-D4-pregnene-3,20-dione	HMDB
21-Hydroxy-pregn-4-ene-3,20-dione	HMDB
21-Hydroxy-progesterone	HMDB
21-Hydroxypregn-4-ene-3,20-dione	HMDB
D4-Pregnene-21-ol-3,20-dione	HMDB
Deoxycortone	HMDB
Doca	HMDB
11-Decorticosterone	HMDB
21 Hydroxyprogesterone	HMDB
11 Decorticosterone	HMDB
21 Hydroxy 4 pregnene 3,20 dione	HMDB
Deoxycorticosterone	ChEBI

Chemical Formula

C₂₁H₃₀O₃

Average Mass

330.4611 Da

Monoisotopic Mass

330.21949 Da

IUPAC Name

(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

64-85-7

SMILES

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

InChI Identifier

InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1

InChI Key

ZESRJSPZRDMNHY-YFWFAHHUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abedus herberti	LOTUS Database	35616633
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
Dytiscus marginalis	LOTUS Database	35616633
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Ilybiosoma seriatum	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
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
Trachelospermum gracilipes	LOTUS Database	35616633

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
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:16973 )
20-oxo steroid (CHEBI:16973 )
mineralocorticoid (CHEBI:16973 )
21-hydroxy steroid (CHEBI:16973 )
Pregnane and derivatives [Fig] (C03205 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C03205 )
Mineralocorticoids (C03205 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030087 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	141 - 142 °C	https://pubchem.ncbi.nlm.nih.gov/compound/6166
Boiling Point	Not Available	Not Available
Water Solubility	0.06 mg/mL at 37 °C	https://pubchem.ncbi.nlm.nih.gov/compound/6166
LogP	2.88	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.33	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.41 m³·mol⁻¹	ChemAxon
Polarizability	38.19 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

HMDB0000016

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006404

KNApSAcK ID

Not Available

Chemspider ID

5932

KEGG Compound ID

C03205

BioCyc ID

11-DEOXYCORTICOSTERONE

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16973

Good Scents ID

rw1234671

References

General References

White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. [PubMed:8081391 ]
Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. [PubMed:2808702 ]
Bureik M, Bruck N, Hubel K, Bernhardt R: The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast. FEMS Yeast Res. 2005 Apr;5(6-7):627-33. [PubMed:15780662 ]
Muto S, Akai Y, Ono S, Kusano E, Asano Y: Selective hypoaldosteronism due to combined defects of the conversion from inactive renin to active renin and the aldosterone biosynthesis from corticosterone. Nephron. 2001 Jul;88(3):247-53. [PubMed:11423756 ]
Bruynseels J, De Coster R, Van Rooy P, Wouters W, Coene MC, Snoeck E, Raeymaekers A, Freyne E, Sanz G, Vanden Bussche G, et al.: R 75251, a new inhibitor of steroid biosynthesis. Prostate. 1990;16(4):345-57. [PubMed:2164659 ]
Holmes NM, Miller WL, Baskin LS: Lack of defects in androgen production in children with hypospadias. J Clin Endocrinol Metab. 2004 Jun;89(6):2811-6. [PubMed:15181062 ]
Sippell WG, Muller-Holve W, Dorr HG, Bidlingmaier F, Knorr D: Concentrations of aldosterone, corticosterone, 11-deoxycorticosterone, progesterone, 17-hydroxyprogesterone, 11-deoxycortisol, cortisol, and cortisone determined simultaneously in human amniotic fluid throughout gestation. J Clin Endocrinol Metab. 1981 Mar;52(3):385-92. [PubMed:7462398 ]
Namiki M, Koh E, Meguro N, Kondoh N, Kiyohara H, Okuyama A, Sakoda S, Matsumoto K, Sonoda T: Extraadrenal expression of steroid 21-hydroxylase and 11 beta-hydroxylase by a benign testicular Leydig cell tumor. J Steroid Biochem Mol Biol. 1991 Dec;39(6):897-901. [PubMed:1751389 ]
Wyss JM, Oparil S, Sripairojthikoon W: Neuronal control of the kidney: contribution to hypertension. Can J Physiol Pharmacol. 1992 May;70(5):759-70. [PubMed:1423019 ]
Pakravan P, Kenny FM, Depp R, Allen AC: Familial congenital absence of adrenal glands; evaluation of glucocorticoid, mineralocorticoid, and estrogen metabolism in the perinatal period. J Pediatr. 1974 Jan;84(1):74-8. [PubMed:12119960 ]
Krone N, Riepe FG, Grotzinger J, Partsch CJ, Sippell WG: Functional characterization of two novel point mutations in the CYP21 gene causing simple virilizing forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2005 Jan;90(1):445-54. Epub 2004 Oct 13. [PubMed:15483094 ]
Deng PY, Li YJ: Calcitonin gene-related peptide and hypertension. Peptides. 2005 Sep;26(9):1676-85. Epub 2005 Mar 2. [PubMed:16112410 ]
Funder JW: Mineralocorticoid receptors: distribution and activation. Heart Fail Rev. 2005 Jan;10(1):15-22. [PubMed:15947887 ]
Bassett MH, White PC, Rainey WE: The regulation of aldosterone synthase expression. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):67-74. [PubMed:15134803 ]
Ahmad N, Romero DG, Gomez-Sanchez EP, Gomez-Sanchez CE: Do human vascular endothelial cells produce aldosterone? Endocrinology. 2004 Aug;145(8):3626-9. Epub 2004 Apr 29. [PubMed:15117882 ]
Mussig K, Wehrmann M, Horger M, Maser-Gluth C, Haring HU, Overkamp D: Adrenocortical carcinoma producing 11-deoxycorticosterone: a rare cause of mineralocorticoid hypertension. J Endocrinol Invest. 2005 Jan;28(1):61-5. [PubMed:15816373 ]
Azar ST, Melby JC: 19-Nor-deoxycorticosterone production from aldosterone-producing adenomas. Hypertension. 1992 Apr;19(4):362-4. [PubMed:1555868 ]
Hogan MJ, Schambelan M, Biglieri EG: Concurrent hypercortisolism and hypermineralocorticoidism. Am J Med. 1977 May;62(5):777-82. [PubMed:871129 ]
Ni W, Thompson JM, Northcott CA, Lookingland K, Watts SW: The serotonin transporter is present and functional in peripheral arterial smooth muscle. J Cardiovasc Pharmacol. 2004 Jun;43(6):770-81. [PubMed:15167270 ]
Campion J, Lahera V, Cachofeiro V, Maestro B, Davila N, Carranza MC, Calle C: In vivo tissue specific modulation of rat insulin receptor gene expression in an experimental model of mineralocorticoid excess. Mol Cell Biochem. 1998 Aug;185(1-2):177-82. [PubMed:9746224 ]
Gupta S, Melendez J, Khanna A: Deoxycorticosterone producing tumor as a cause of resistant hypertension. Case Rep Med. 2010;2010:372719. doi: 10.1155/2010/372719. Epub 2010 Jun 30. [PubMed:20671982 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing NP-Card for Deoxycorticosterone (NP0000090)

MOL for NP0000090 (Deoxycorticosterone)

3D MOL for NP0000090 (Deoxycorticosterone)

3D SDF for NP0000090 (Deoxycorticosterone)

3D-SDF for NP0000090 (Deoxycorticosterone)

PDB for NP0000090 (Deoxycorticosterone)

3D PDB for NP0000090 (Deoxycorticosterone)

SMILES for NP0000090 (Deoxycorticosterone)

INCHI for NP0000090 (Deoxycorticosterone)

Structure for NP0000090 (Deoxycorticosterone)

3D Structure for NP0000090 (Deoxycorticosterone)