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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-05-22 18:20:36 UTC

Update Date

2022-03-07 02:49:30 UTC

HMDB ID

HMDB0006225

Secondary Accession Numbers

HMDB06225

Metabolite Identification

Common Name

Ercalcitriol

Description

Ercalcitriol is the active circulating metabolite of vitamin D2. Vitamin D2 is modified by 25-hydroxylase in the liver and 25-hydroxyvitamin D *-hydroxylase in the kidney to form the active metabolite, ercalcitriol, which is then metabolized by 25-hydroxyvitamin D-24-hydroxylase (24-OHase, CYP24A1, EC 1.14.13.13). The binding of ercalcitriol or their analogs to Vitamin D receptor (VDR), a nuclear receptor, activates VDR to interact with retinoid X receptor (RXR) and forms the VDR/RXR/cofactor complex, which binds to Vitamin D response elements in the promoter region of target genes to regulate gene transcription. The kidney is the major site of 25-hydroxyvitamin D*-hydroxylase (CYP27B1, EC 1.14.13.13), which is responsible for the activation of 25-hydroxyvitamin D. Of all the steroid hormones, ercalcitriol represents the most difficult challenge to the analytical biochemist with respect to quantization. Ercalcitriol circulates at pmol concentrations, is highly lipophilic and its precursor, 25-hydroxyvitamin D2, circulates at nmol levels. (PMID: 16242929 , 17867378 , 17197173 ).

Structure

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

  Mrv0541 02231220342D          

 33 35  0  0  1  0            999 V2000
   13.8875  -11.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7456  -11.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7456   -6.7763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5262   -6.5247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7456   -7.6013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0077   -7.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5262   -7.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311   -6.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7825   -5.7406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0311   -8.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7456   -5.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167   -6.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167   -7.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2315   -5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5898   -5.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311   -8.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8462   -4.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167   -9.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6534   -4.6161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.3167  -10.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9097   -3.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6021  -10.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2044   -5.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -10.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6021  -11.3138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0311  -11.3138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.3167  -11.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7456  -10.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1782   -6.4224    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8155   -8.2575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7170   -3.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3588   -3.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1024   -4.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 25  1  1  6  0  0  0
 26  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  1  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  4 29  1  6  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  5 30  1  6  0  0  0
  6  7  1  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  6  0  0  0
  9 15  1  0  0  0  0
 10 13  1  0  0  0  0
 10 16  2  0  0  0  0
 12 13  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  1  0  0  0  0
 19 23  1  1  0  0  0
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 20 24  1  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 28  2  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
 31 21  1  0  0  0  0
 32 21  1  0  0  0  0
 33 21  1  0  0  0  0
M  END

HMDB0006225
     RDKit          3D
Ercalcitriol
 75 77  0  0  0  0  0  0  0  0999 V2000
   -4.5713   -0.4136   -1.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4397   -0.0787   -1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0146    0.2182    2.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9373   -0.2233    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4825    0.8699   -0.9959 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.0313   -0.7208   -2.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -0.4762   -0.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075   -0.0049   -0.8525 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8617   -0.6611   -0.0370 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4223   -1.9868    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706    0.2549    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653    1.5227    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4943   -0.4713    1.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527    0.5890    1.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2551   -1.1711    1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7862   -1.0130    2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0552   -1.3402    1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9519    0.1778    1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5276   -1.8817   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385    2.0123    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135    2.7832   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    1.1229   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    2.8265   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255    1.4366   -2.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236    1.5834   -0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    1.0356   -2.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -0.5385   -3.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0264    0.9095   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7208   -0.8568   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3351   -2.5160    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068   -2.5864   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6564   -1.8981    1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6327    1.2774   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2741   -0.7465    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9532    0.2802    2.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207    1.3653    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3505   -0.7738    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5824   -1.4884   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6411   -2.0803    1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5376    0.9868   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4172    1.7335   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4544    0.8899   -3.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
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 29 72  1  0
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 30 74  1  6
 31 75  1  0
M  END

  Mrv0541 02231220342D          

 33 35  0  0  1  0            999 V2000
   13.8875  -11.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7456  -11.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7456   -6.7763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5262   -6.5247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7456   -7.6013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0077   -7.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7825   -5.7406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0311   -8.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7456   -5.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167   -6.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.7170   -3.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 20 24  1  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 28  2  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
 31 21  1  0  0  0  0
 32 21  1  0  0  0  0
 33 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006225

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](\C=C\[C@H](C)C(O)(C)C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1

> <INCHI_KEY>
ZGLHBRQAEXKACO-XJRQOBMKSA-N

> <FORMULA>
C28H44O3

> <MOLECULAR_WEIGHT>
428.6472

> <EXACT_MASS>
428.329045274

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
52.279914458078665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
4.353792166333335

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.288747760728633

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.392873609816359

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0302987747658645

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
132.12069999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006225
     RDKit          3D
Ercalcitriol
 75 77  0  0  0  0  0  0  0  0999 V2000
   -4.5713   -0.4136   -1.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4397   -0.0787   -1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668   -0.5224    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542   -0.2730    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161    0.3976    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    0.5466    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494    0.0291    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146    0.2182    2.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9373   -0.2233    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175    0.1266   -0.2022 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1394   -1.0586   -0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5765    1.2001   -0.0280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7635    1.7214   -1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6746    1.7878   -1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4825    0.8699   -0.9959 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5096    0.2003   -1.8038 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0313   -0.7208   -2.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -0.4762   -0.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075   -0.0049   -0.8525 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8617   -0.6611   -0.0370 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4223   -1.9868    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706    0.2549    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653    1.5227    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4943   -0.4713    1.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527    0.5890    1.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2551   -1.1711    1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5407   -0.8562    0.3746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6692   -1.1159    1.1569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5257    0.5878   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7001    0.6876   -1.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3648    0.1565   -2.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230   -0.0511   -2.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098   -1.0075   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7405   -0.6055    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9884    0.8525   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0289    0.6618    2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.0130    2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378   -0.3804    3.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    1.2801    2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552   -1.3402    1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9519    0.1778    1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884   -0.8035   -1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.5034    0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -1.8817   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385    2.0123    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135    2.7832   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    1.1229   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    2.8265   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255    1.4366   -2.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236    1.5834   -0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    1.0356   -2.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -0.5385   -3.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704   -1.7664   -2.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -0.6708   -3.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3436   -1.3902   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0264    0.9095   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7208   -0.8568   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3351   -2.5160    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068   -2.5864   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6564   -1.8981    1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1929    2.2343    0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6111    1.9926    1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6327    1.2774   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2741   -0.7465    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1329   -1.3049    2.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9532    0.2802    2.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207    1.3653    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1675   -2.2769    1.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3505   -0.7738    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5824   -1.4884   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6411   -2.0803    1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5376    0.9868   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9729    1.1765    0.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4172    1.7335   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4544    0.8899   -3.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
  3 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 30  2  1  0
 12  6  1  0
 15 10  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 11 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  1
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 16 51  1  6
 17 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  6
 21 58  1  0
 21 59  1  0
 21 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 24 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  6
 28 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  6
 31 75  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      25.923 -21.889   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.258 -21.889   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      31.258 -12.649   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.716 -12.179   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.258 -14.189   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.614 -13.419   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.716 -14.658   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.925 -11.879   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.194 -10.716   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.925 -14.959   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.258 -11.109   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.591 -12.649   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.591 -14.189   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.165  -9.569   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.701 -10.398   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.925 -16.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.180  -8.934   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.591 -17.269   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.686  -8.617   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.591 -18.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.165  -7.153   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.257 -19.579   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.715  -9.763   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.925 -19.579   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.257 -21.119   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.925 -21.119   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.591 -21.889   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.258 -18.809   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      33.933 -11.988   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      31.389 -15.414   0.000  0.00  0.00           H+0
HETATM   31  O   UNK     0      38.672  -6.835   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      36.136  -6.007   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      35.658  -7.471   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3    4    5    8   11                                             
CONECT    4    3    6    9   29                                             
CONECT    5    3    7   10   30                                             
CONECT    6    4    7                                                       
CONECT    7    5    6                                                       
CONECT    8    3   12                                                       
CONECT    9    4   14   15                                                  
CONECT   10    5   13   16                                                  
CONECT   11    3                                                            
CONECT   12    8   13                                                       
CONECT   13   10   12                                                       
CONECT   14    9                                                            
CONECT   15    9   17                                                       
CONECT   16   10   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   21   23                                                  
CONECT   20   18   22   24                                                  
CONECT   21   19   31   32   33                                             
CONECT   22   20   25                                                       
CONECT   23   19                                                            
CONECT   24   20   26   28                                                  
CONECT   25    1   22   27                                                  
CONECT   26    2   24   27                                                  
CONECT   27   25   26                                                       
CONECT   28   24                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31   21                                                            
CONECT   32   21                                                            
CONECT   33   21                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

COMPND    HMDB0006225
HETATM    1  C1  UNL     1      -4.571  -0.414  -1.948  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.440  -0.079  -1.015  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.167  -0.522   0.366  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.954  -0.273   0.808  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.916   0.398   0.052  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.706   0.547   0.617  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.449   0.029   1.988  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.015   0.218   2.275  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.937  -0.223   1.198  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.517   0.127  -0.202  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.139  -1.059  -0.803  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.576   1.200  -0.028  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.763   1.721  -1.393  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.675   1.788  -1.922  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.482   0.870  -0.996  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.510   0.200  -1.804  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.031  -0.721  -2.877  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.572  -0.476  -0.972  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.807  -0.005  -0.853  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.862  -0.661  -0.037  1.00  0.00           C  
HETATM   21  C21 UNL     1       5.422  -1.987   0.515  1.00  0.00           C  
HETATM   22  C22 UNL     1       6.371   0.255   1.062  1.00  0.00           C  
HETATM   23  C23 UNL     1       6.965   1.523   0.487  1.00  0.00           C  
HETATM   24  C24 UNL     1       7.494  -0.471   1.781  1.00  0.00           C  
HETATM   25  O1  UNL     1       5.353   0.589   1.947  1.00  0.00           O  
HETATM   26  C25 UNL     1      -6.255  -1.171   1.160  1.00  0.00           C  
HETATM   27  C26 UNL     1      -7.541  -0.856   0.375  1.00  0.00           C  
HETATM   28  O2  UNL     1      -8.669  -1.116   1.157  1.00  0.00           O  
HETATM   29  C27 UNL     1      -7.526   0.588  -0.042  1.00  0.00           C  
HETATM   30  C28 UNL     1      -6.700   0.688  -1.332  1.00  0.00           C  
HETATM   31  O3  UNL     1      -7.365   0.156  -2.411  1.00  0.00           O  
HETATM   32  H1  UNL     1      -4.823  -0.051  -2.964  1.00  0.00           H  
HETATM   33  H2  UNL     1      -3.710  -1.008  -1.794  1.00  0.00           H  
HETATM   34  H3  UNL     1      -3.741  -0.606   1.821  1.00  0.00           H  
HETATM   35  H4  UNL     1      -2.988   0.853  -0.914  1.00  0.00           H  
HETATM   36  H5  UNL     1      -2.029   0.662   2.690  1.00  0.00           H  
HETATM   37  H6  UNL     1      -1.786  -1.013   2.133  1.00  0.00           H  
HETATM   38  H7  UNL     1       0.238  -0.380   3.193  1.00  0.00           H  
HETATM   39  H8  UNL     1       0.157   1.280   2.567  1.00  0.00           H  
HETATM   40  H9  UNL     1       1.055  -1.340   1.281  1.00  0.00           H  
HETATM   41  H10 UNL     1       1.952   0.178   1.445  1.00  0.00           H  
HETATM   42  H11 UNL     1      -0.888  -0.803  -1.610  1.00  0.00           H  
HETATM   43  H12 UNL     1      -0.799  -1.503   0.004  1.00  0.00           H  
HETATM   44  H13 UNL     1       0.528  -1.882  -1.089  1.00  0.00           H  
HETATM   45  H14 UNL     1      -0.138   2.012   0.602  1.00  0.00           H  
HETATM   46  H15 UNL     1      -1.114   2.783  -1.323  1.00  0.00           H  
HETATM   47  H16 UNL     1      -1.346   1.123  -2.087  1.00  0.00           H  
HETATM   48  H17 UNL     1       1.062   2.826  -1.916  1.00  0.00           H  
HETATM   49  H18 UNL     1       0.726   1.437  -2.975  1.00  0.00           H  
HETATM   50  H19 UNL     1       2.024   1.583  -0.305  1.00  0.00           H  
HETATM   51  H20 UNL     1       3.063   1.036  -2.338  1.00  0.00           H  
HETATM   52  H21 UNL     1       2.560  -0.539  -3.862  1.00  0.00           H  
HETATM   53  H22 UNL     1       2.370  -1.766  -2.612  1.00  0.00           H  
HETATM   54  H23 UNL     1       0.971  -0.671  -3.110  1.00  0.00           H  
HETATM   55  H24 UNL     1       3.344  -1.390  -0.436  1.00  0.00           H  
HETATM   56  H25 UNL     1       5.026   0.909  -1.392  1.00  0.00           H  
HETATM   57  H26 UNL     1       6.721  -0.857  -0.713  1.00  0.00           H  
HETATM   58  H27 UNL     1       6.335  -2.516   0.868  1.00  0.00           H  
HETATM   59  H28 UNL     1       5.007  -2.586  -0.321  1.00  0.00           H  
HETATM   60  H29 UNL     1       4.656  -1.898   1.310  1.00  0.00           H  
HETATM   61  H30 UNL     1       6.193   2.234   0.149  1.00  0.00           H  
HETATM   62  H31 UNL     1       7.611   1.993   1.276  1.00  0.00           H  
HETATM   63  H32 UNL     1       7.633   1.277  -0.352  1.00  0.00           H  
HETATM   64  H33 UNL     1       8.274  -0.747   1.056  1.00  0.00           H  
HETATM   65  H34 UNL     1       7.133  -1.305   2.393  1.00  0.00           H  
HETATM   66  H35 UNL     1       7.953   0.280   2.464  1.00  0.00           H  
HETATM   67  H36 UNL     1       5.621   1.365   2.476  1.00  0.00           H  
HETATM   68  H37 UNL     1      -6.167  -2.277   1.162  1.00  0.00           H  
HETATM   69  H38 UNL     1      -6.350  -0.774   2.169  1.00  0.00           H  
HETATM   70  H39 UNL     1      -7.582  -1.488  -0.538  1.00  0.00           H  
HETATM   71  H40 UNL     1      -8.641  -2.080   1.395  1.00  0.00           H  
HETATM   72  H41 UNL     1      -8.538   0.987  -0.224  1.00  0.00           H  
HETATM   73  H42 UNL     1      -6.973   1.176   0.710  1.00  0.00           H  
HETATM   74  H43 UNL     1      -6.417   1.733  -1.482  1.00  0.00           H  
HETATM   75  H44 UNL     1      -7.454   0.890  -3.098  1.00  0.00           H  
CONECT    1    2    2   32   33
CONECT    2    3   30
CONECT    3    4    4   26
CONECT    4    5   34
CONECT    5    6    6   35
CONECT    6    7   12
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   40   41
CONECT   10   11   12   15
CONECT   11   42   43   44
CONECT   12   13   45
CONECT   13   14   46   47
CONECT   14   15   48   49
CONECT   15   16   50
CONECT   16   17   18   51
CONECT   17   52   53   54
CONECT   18   19   19   55
CONECT   19   20   56
CONECT   20   21   22   57
CONECT   21   58   59   60
CONECT   22   23   24   25
CONECT   23   61   62   63
CONECT   24   64   65   66
CONECT   25   67
CONECT   26   27   68   69
CONECT   27   28   29   70
CONECT   28   71
CONECT   29   30   72   73
CONECT   30   31   74
CONECT   31   75
END

HMDB0006225
     RDKit          3D
Ercalcitriol
 75 77  0  0  0  0  0  0  0  0999 V2000
   -4.5713   -0.4136   -1.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4397   -0.0787   -1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668   -0.5224    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542   -0.2730    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161    0.3976    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    0.5466    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494    0.0291    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146    0.2182    2.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9373   -0.2233    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175    0.1266   -0.2022 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1394   -1.0586   -0.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5765    1.2001   -0.0280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7635    1.7214   -1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6746    1.7878   -1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4825    0.8699   -0.9959 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5096    0.2003   -1.8038 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0313   -0.7208   -2.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -0.4762   -0.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075   -0.0049   -0.8525 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8617   -0.6611   -0.0370 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4223   -1.9868    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706    0.2549    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653    1.5227    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4943   -0.4713    1.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527    0.5890    1.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2551   -1.1711    1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5407   -0.8562    0.3746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6692   -1.1159    1.1569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5257    0.5878   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7001    0.6876   -1.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3648    0.1565   -2.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230   -0.0511   -2.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098   -1.0075   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7405   -0.6055    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9884    0.8525   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0289    0.6618    2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.0130    2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378   -0.3804    3.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    1.2801    2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552   -1.3402    1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9519    0.1778    1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884   -0.8035   -1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.5034    0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -1.8817   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1385    2.0123    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135    2.7832   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    1.1229   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    2.8265   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255    1.4366   -2.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236    1.5834   -0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    1.0356   -2.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -0.5385   -3.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704   -1.7664   -2.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -0.6708   -3.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3436   -1.3902   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0264    0.9095   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7208   -0.8568   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3351   -2.5160    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068   -2.5864   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6564   -1.8981    1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1929    2.2343    0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6111    1.9926    1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6327    1.2774   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2741   -0.7465    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1329   -1.3049    2.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9532    0.2802    2.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207    1.3653    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1675   -2.2769    1.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3505   -0.7738    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5824   -1.4884   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6411   -2.0803    1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5376    0.9868   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9729    1.1765    0.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4172    1.7335   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4544    0.8899   -3.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
  3 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 30  2  1  0
 12  6  1  0
 15 10  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 11 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  1
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 16 51  1  6
 17 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  6
 21 58  1  0
 21 59  1  0
 21 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 24 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  6
 28 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  6
 31 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,25-Dihydroxycalciferol	ChEBI
1,25-Dihydroxyergocalciferol	ChEBI
1,25-Dihydroxyvitamin D2	ChEBI
1alpha,25-Dihydroxycalciferol	ChEBI
1alpha,25-Dihydroxyergocalciferol	ChEBI
1a,25-Dihydroxycalciferol	Generator
1Α,25-dihydroxycalciferol	Generator
1a,25-Dihydroxyergocalciferol	Generator
1Α,25-dihydroxyergocalciferol	Generator
1a,25-Dihydroxyvitamin D2 / 1a,,25-dihydroxyergocalciferol	HMDB
1Α,25-dihydroxyvitamin D2 / 1α,,25-dihydroxyergocalciferol	HMDB
1 alpha,25-Dihydroxyvitamin D2	HMDB
1,25-Dihydroxyergocalciferol, (1alpha,3beta,5Z,7E,22E)-isomer	HMDB
1,25-(OH)2D2	HMDB
Ercalcitriol	ChEBI
1a,25-Dihydroxyvitamin D2	Generator
1Α,25-dihydroxyvitamin D2	Generator

Chemical Formula

C₂₈H₄₄O₃

Average Molecular Weight

428.6472

Monoisotopic Molecular Weight

428.329045274

IUPAC Name

(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

Traditional Name

(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

CAS Registry Number

60133-18-8

SMILES

C[C@H](\C=C\[C@H](C)C(O)(C)C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C

InChI Identifier

InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1

InChI Key

ZGLHBRQAEXKACO-XJRQOBMKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Triterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxycalciol (CHEBI:86320 )
seco-ergostane (CHEBI:86320 )
vitamin D (CHEBI:86320 )
Vitamin D2 and derivatives (LMST03010040 )

Ontology

Not Available

Feces (PMID: 26848182)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006225)

Extracellular (HMDB: HMDB0006225)
Membrane (HMDB: HMDB0006225)

Source

Exogenous

Exogenous (HMDB: HMDB0006225)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0006225)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.007 g/L	ALOGPS
logP	5.45	ALOGPS
logP	4.35	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.39	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.12 m³·mol⁻¹	ChemAxon
Polarizability	52.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	204.477	31661259
DarkChem	[M-H]-	203.846	31661259
DeepCCS	[M-2H]-	244.93	30932474
DeepCCS	[M+Na]+	219.013	30932474
AllCCS	[M+H]+	210.4	32859911
AllCCS	[M+H-H2O]+	208.3	32859911
AllCCS	[M+NH4]+	212.4	32859911
AllCCS	[M+Na]+	212.9	32859911
AllCCS	[M-H]-	209.7	32859911
AllCCS	[M+Na-2H]-	211.9	32859911
AllCCS	[M+HCOO]-	214.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ercalcitriol	C[C@H](\C=C\[C@H](C)C(O)(C)C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C	4013.9	Standard polar	33892256
Ercalcitriol	C[C@H](\C=C\[C@H](C)C(O)(C)C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C	3399.5	Standard non polar	33892256
Ercalcitriol	C[C@H](\C=C\[C@H](C)C(O)(C)C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C	3582.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ercalcitriol,1TMS,isomer #1	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O	3549.8	Semi standard non polar	33892256
Ercalcitriol,1TMS,isomer #2	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O	3486.2	Semi standard non polar	33892256
Ercalcitriol,1TMS,isomer #3	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C	3487.7	Semi standard non polar	33892256
Ercalcitriol,2TMS,isomer #1	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O	3495.7	Semi standard non polar	33892256
Ercalcitriol,2TMS,isomer #2	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C	3485.5	Semi standard non polar	33892256
Ercalcitriol,2TMS,isomer #3	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	3403.8	Semi standard non polar	33892256
Ercalcitriol,3TMS,isomer #1	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	3419.3	Semi standard non polar	33892256
Ercalcitriol,1TBDMS,isomer #1	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O	3780.4	Semi standard non polar	33892256
Ercalcitriol,1TBDMS,isomer #2	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O	3708.1	Semi standard non polar	33892256
Ercalcitriol,1TBDMS,isomer #3	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3689.0	Semi standard non polar	33892256
Ercalcitriol,2TBDMS,isomer #1	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O	3956.4	Semi standard non polar	33892256
Ercalcitriol,2TBDMS,isomer #2	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3918.1	Semi standard non polar	33892256
Ercalcitriol,2TBDMS,isomer #3	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	3820.8	Semi standard non polar	33892256
Ercalcitriol,3TBDMS,isomer #1	C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	4077.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ercalcitriol GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-4029600000-dbfa8697870ebd683025	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ercalcitriol GC-MS (3 TMS) - 70eV, Positive	splash10-003r-1400149000-b8a11d6c4c1ad554146e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ercalcitriol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 10V, Positive-QTOF	splash10-03dl-0119800000-7dd9f14f9a8c59dc34da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 20V, Positive-QTOF	splash10-0gvx-1329200000-0a0f4f399ef35e7f8039	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 40V, Positive-QTOF	splash10-03dr-4449200000-6bc7143e80424071bd59	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 10V, Negative-QTOF	splash10-004i-0001900000-01f91a65a26969417dc3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 20V, Negative-QTOF	splash10-0a6r-0004900000-35bc1dcb432dd5b31686	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 40V, Negative-QTOF	splash10-0i09-7109200000-c0e2fe47359423d7eee0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 10V, Negative-QTOF	splash10-004i-0000900000-be3d96e63cee98d539bf	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 20V, Negative-QTOF	splash10-004i-1402900000-1f6915f21eef2875a071	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 40V, Negative-QTOF	splash10-002f-2319300000-299bc94defd194cd6fac	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 10V, Positive-QTOF	splash10-014r-0193200000-a4d6e13ad596312a24b2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 20V, Positive-QTOF	splash10-014r-1094000000-5a9b3afb3048a2dde8d9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ercalcitriol 40V, Positive-QTOF	splash10-03y0-4982000000-9e151864bb3f37c45627	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Inflammatory bowel disease	26848182	details

Associated Disorders and Diseases

Disease References

Inflammatory bowel disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023845

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9547243

PDB ID

Not Available

ChEBI ID

86320

Food Biomarker Ontology

Not Available

VMH ID

1A25DHVITD2

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Sicinski, Rafal R.; Tanaka, Yoko; Schnoes, Heinrich K.; DeLuca, Hector F. Synthesis of 1a, 25-dihydroxyvitamin D2, its 24 epimer and related isomers, and their binding affinity for the 1,25-dihydroxyvitamin D3 receptor. Bioorganic Chemistry (1985), 13(2), 158-69.

Material Safety Data Sheet (MSDS)

Not Available

General References

Nakane M, Fey TA, Dixon DB, Ma J, Brune ME, Li YC, Wu-Wong JR: Differential effects of Vitamin D analogs on bone formation and resorption. J Steroid Biochem Mol Biol. 2006 Jan;98(1):72-7. Epub 2005 Oct 20. [PubMed:16242929 ]
Hollis BW: Assessment of circulating 25(OH)D and 1,25(OH)2D: emergence as clinically important diagnostic tools. Nutr Rev. 2007 Aug;65(8 Pt 2):S87-90. [PubMed:17867378 ]
Hollis BW, Horst RL: The assessment of circulating 25(OH)D and 1,25(OH)2D: where we are and where we are going. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):473-6. Epub 2007 Jan 2. [PubMed:17197173 ]

Enzymes

Enzyme Details

1. 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
Gene Name:: CYP27B1
Uniprot ID:: O15528
Molecular weight:: 56503.475

Enzyme Details

2. 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can perform up to 6 rounds of hydroxylation of calcitriol leading to calcitroic acid. It also shows 23-hydroxylating activity leading to 1-alpha,25-dihydroxyvitamin D(3)-26,23-lactone as end product.
Gene Name:: CYP24A1
Uniprot ID:: Q07973
Molecular weight:: 58874.695

Showing metabocard for Ercalcitriol (HMDB0006225)

MOL for HMDB0006225 (Ercalcitriol)

3D MOL for HMDB0006225 (Ercalcitriol)

3D SDF for HMDB0006225 (Ercalcitriol)

3D-SDF for HMDB0006225 (Ercalcitriol)

PDB for HMDB0006225 (Ercalcitriol)

3D PDB for HMDB0006225 (Ercalcitriol)

SMILES for HMDB0006225 (Ercalcitriol)

INCHI for HMDB0006225 (Ercalcitriol)

Structure for HMDB0006225 (Ercalcitriol)

3D Structure for HMDB0006225 (Ercalcitriol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes