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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 10:53:13 UTC

Update Date

2021-09-14 15:40:07 UTC

HMDB ID

HMDB0006472

Secondary Accession Numbers

HMDB06472

Metabolite Identification

Common Name

Calcitroic acid

Description

Calcitroic acid (1 alpha-hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)) is a metabolite of 1 alpha, 25-dihydroxyvitamin D(3) (calcitriol). It is soluble in water, and is excreted in urine. This deactivation process involves a series of oxidation reactions at C24 and C23 leading to side-chain cleavage and, ultimately, formation of the calcitroic acid. This deactivation involves the loss of carbons 24, 25, 26, and 27 and the oxidation of carbon 23 to a carboxylic acid. Calcitroic acid is also a major terminal product for the deactivation of 1α,25-dihydroxyvitamin D2. Both the kidney and the intestine metabolize 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway according to the following steps: 1,25-dihydroxyvitamin D3----1,24,25-trihydroxyvitamin D3----1,25-dihydroxy-24-oxovitamin D3-----1,23,25-trihydroxy-24-oxovitamin D3 (PMID: 2719932 ). The C-24 oxidation pathway leading to the formation of calcitroic acid has been reported to be present in bone cells, but the C-23 oxidation pathway leading to the formation of 1 alpha, 25-(OH)2D3-26,23-lactone has not been described in bone cells, even though 1 alpha, 25-(OH)2D3-26,23-lactone is noted to have a significant effect on bone formation. (PMID: 7664636 ).

Structure

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


  Mrv0541 02231220402D          

 28 30  0  0  1  0            999 V2000
   14.3402  -12.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5152  -12.5788    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1026  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5152  -11.1498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3402  -11.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7526  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5776  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9902  -12.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7526  -10.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1026  -10.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1026  -13.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8152  -12.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2276  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2276  -13.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0526  -13.2932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4652  -12.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0526  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9728  -14.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6402  -14.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3076  -14.0778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.0922  -14.3328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2638  -15.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7053  -13.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4899  -14.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1030  -13.4837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6615  -14.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8649  -13.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4154  -13.4377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
  4 10  1  6  0  0  0
  2 11  1  1  0  0  0
 12  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 20 15  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  1  0  0  0
 23 21  1  0  0  0  0
 25 24  2  0  0  0  0
 26 24  1  0  0  0  0
 23 24  1  0  0  0  0
 15 27  1  1  0  0  0
 14 28  1  6  0  0  0
M  END

HMDB0006472
     RDKit          3D
Calcitroic acid
 61 63  0  0  0  0  0  0  0  0999 V2000
   -4.8283   -1.5976    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8409   -0.7446    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910   -0.1997   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6112   -0.0516    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    0.4923   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    0.6643    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4143    0.3146    2.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    0.7291    2.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167    0.1465    2.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0841    0.1888    0.6005 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5982   -1.1149    0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609    1.1998    0.2760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1596    1.3043   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727    1.3268   -1.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    0.8343   -0.0455 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5245    0.1543   -0.1858 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5497   -1.1030   -0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0948   -0.1590    1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4283   -0.8156    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0520   -1.0880    0.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9905   -1.1360    2.3699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4945    0.1529   -1.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8708    0.0913   -2.5517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1566   -1.2598   -2.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8803    0.6971   -1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1658   -0.3580   -0.5450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0109    0.1364    0.4370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -1.9237    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274   -2.0266    1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -0.3056    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998    0.7613   -1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    0.9825    2.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -0.7316    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.4546    3.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0064    1.8365    2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    0.6916    2.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -0.9146    2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304   -1.3243    0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755   -1.2152   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809   -1.9214    0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357    2.1774    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    2.2293   -1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    0.4644   -1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9763    2.3840   -1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9963    0.7404   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4329    1.7844    0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2243    0.8807   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5075   -1.1124   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714   -1.0574   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5494   -2.0342   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2297    0.7829    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -0.9087    1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9929   -0.4819    3.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355    1.2092   -2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -0.5002   -2.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    0.6431   -3.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3202   -1.4201   -3.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7963    1.0263   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3635    1.5264   -1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5667   -1.2472   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9112   -0.2549    0.4147 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  1  0
 19 20  2  0
 19 21  1  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26  2  1  0
 12  6  1  0
 15 10  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  1
 16 47  1  6
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  6
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  6
 27 61  1  0
M  END


  Mrv0541 02231220402D          

 28 30  0  0  1  0            999 V2000
   14.3402  -12.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5152  -12.5788    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1026  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5152  -11.1498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3402  -11.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7526  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5776  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9902  -12.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7526  -10.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1026  -10.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1026  -13.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8152  -12.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2276  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2276  -13.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0526  -13.2932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4652  -12.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0526  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9728  -14.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6402  -14.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3076  -14.0778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.0922  -14.3328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2638  -15.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7053  -13.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4899  -14.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1030  -13.4837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6615  -14.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8649  -13.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4154  -13.4377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
  4 10  1  6  0  0  0
  2 11  1  1  0  0  0
 12  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 20 15  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  1  0  0  0
 23 21  1  0  0  0  0
 25 24  2  0  0  0  0
 26 24  1  0  0  0  0
 23 24  1  0  0  0  0
 15 27  1  1  0  0  0
 14 28  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0006472

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CC(O)=O)[C@@]1(C)CCC\C2=C/C=C1\C[C@@H](O)C[C@H](O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7+/t14-,18-,19-,20+,21+,23-/m1/s1

> <INCHI_KEY>
MBLYZRMZFUWLOZ-WLWRUGSRSA-N

> <FORMULA>
C23H34O4

> <MOLECULAR_WEIGHT>
374.5137

> <EXACT_MASS>
374.245709576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.64374547994624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoic acid

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
2.880888825333334

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.392873609971762

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.914541246041758

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7596614720148134

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
108.01019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006472
     RDKit          3D
Calcitroic acid
 61 63  0  0  0  0  0  0  0  0999 V2000
   -4.8283   -1.5976    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8409   -0.7446    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910   -0.1997   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6112   -0.0516    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    0.4923   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    0.6643    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4143    0.3146    2.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    0.7291    2.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167    0.1465    2.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0841    0.1888    0.6005 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5982   -1.1149    0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609    1.1998    0.2760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1596    1.3043   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727    1.3268   -1.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    0.8343   -0.0455 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5245    0.1543   -0.1858 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5497   -1.1030   -0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0948   -0.1590    1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4283   -0.8156    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0520   -1.0880    0.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9905   -1.1360    2.3699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4945    0.1529   -1.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8708    0.0913   -2.5517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1566   -1.2598   -2.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8803    0.6971   -1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1658   -0.3580   -0.5450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0109    0.1364    0.4370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -1.9237    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274   -2.0266    1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -0.3056    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998    0.7613   -1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    0.9825    2.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -0.7316    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.4546    3.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0064    1.8365    2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    0.6916    2.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -0.9146    2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304   -1.3243    0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755   -1.2152   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809   -1.9214    0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357    2.1774    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    2.2293   -1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    0.4644   -1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9763    2.3840   -1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9963    0.7404   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4329    1.7844    0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2243    0.8807   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5075   -1.1124   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714   -1.0574   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5494   -2.0342   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2297    0.7829    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -0.9087    1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9929   -0.4819    3.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355    1.2092   -2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -0.5002   -2.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    0.6431   -3.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3202   -1.4201   -3.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7963    1.0263   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3635    1.5264   -1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5667   -1.2472   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9112   -0.2549    0.4147 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  1  0
 19 20  2  0
 19 21  1  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26  2  1  0
 12  6  1  0
 15 10  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  1
 16 47  1  6
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  6
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  6
 27 61  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  C   UNK     0      26.768 -23.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.228 -23.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.458 -22.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.228 -20.813   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.768 -20.813   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.538 -22.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.078 -22.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.848 -23.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.538 -19.479   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.458 -19.479   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      24.458 -24.814   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      31.388 -23.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.158 -22.147   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.158 -24.814   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.698 -24.814   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.468 -23.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.698 -22.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.683 -26.279   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.928 -27.184   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.174 -26.279   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.639 -26.755   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      35.959 -28.261   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.783 -25.724   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.248 -26.200   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      39.392 -25.170   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      38.568 -27.706   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      35.214 -25.084   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      30.642 -25.084   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7   12                                                       
CONECT    9    5                                                            
CONECT   10    4                                                            
CONECT   11    2                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12   17                                                       
CONECT   14   12   15   18   28                                             
CONECT   15   14   16   20   27                                             
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   14   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   25   26   23                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   15                                                            
CONECT   28   14                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0006472
HETATM    1  C1  UNL     1      -4.828  -1.598   1.039  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.841  -0.745   0.035  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.591  -0.200  -0.489  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.611  -0.052   0.366  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.321   0.492  -0.090  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.309   0.664   0.718  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.414   0.315   2.158  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.906   0.729   2.782  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.117   0.147   2.108  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.084   0.189   0.601  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.598  -1.115   0.056  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.961   1.200   0.276  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.160   1.304  -1.213  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.673   1.327  -1.375  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.212   0.834  -0.046  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.524   0.154  -0.186  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.550  -1.103  -0.966  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.095  -0.159   1.193  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.428  -0.816   1.131  1.00  0.00           C  
HETATM   20  O1  UNL     1       7.052  -1.088   0.083  1.00  0.00           O  
HETATM   21  O2  UNL     1       6.991  -1.136   2.370  1.00  0.00           O  
HETATM   22  C20 UNL     1      -3.495   0.153  -1.923  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.871   0.091  -2.552  1.00  0.00           C  
HETATM   24  O3  UNL     1      -5.157  -1.260  -2.799  1.00  0.00           O  
HETATM   25  C22 UNL     1      -5.880   0.697  -1.598  1.00  0.00           C  
HETATM   26  C23 UNL     1      -6.166  -0.358  -0.545  1.00  0.00           C  
HETATM   27  O4  UNL     1      -7.011   0.136   0.437  1.00  0.00           O  
HETATM   28  H1  UNL     1      -3.904  -1.924   1.508  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.727  -2.027   1.462  1.00  0.00           H  
HETATM   30  H3  UNL     1      -2.682  -0.306   1.412  1.00  0.00           H  
HETATM   31  H4  UNL     1      -1.200   0.761  -1.136  1.00  0.00           H  
HETATM   32  H5  UNL     1      -1.177   0.983   2.662  1.00  0.00           H  
HETATM   33  H6  UNL     1      -0.640  -0.732   2.354  1.00  0.00           H  
HETATM   34  H7  UNL     1       0.960   0.455   3.857  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.006   1.837   2.740  1.00  0.00           H  
HETATM   36  H9  UNL     1       2.985   0.692   2.535  1.00  0.00           H  
HETATM   37  H10 UNL     1       2.172  -0.915   2.413  1.00  0.00           H  
HETATM   38  H11 UNL     1       0.530  -1.324   0.375  1.00  0.00           H  
HETATM   39  H12 UNL     1       1.575  -1.215  -1.024  1.00  0.00           H  
HETATM   40  H13 UNL     1       2.181  -1.921   0.585  1.00  0.00           H  
HETATM   41  H14 UNL     1       1.236   2.177   0.730  1.00  0.00           H  
HETATM   42  H15 UNL     1       0.704   2.229  -1.640  1.00  0.00           H  
HETATM   43  H16 UNL     1       0.736   0.464  -1.781  1.00  0.00           H  
HETATM   44  H17 UNL     1       2.976   2.384  -1.558  1.00  0.00           H  
HETATM   45  H18 UNL     1       2.996   0.740  -2.238  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.433   1.784   0.539  1.00  0.00           H  
HETATM   47  H20 UNL     1       5.224   0.881  -0.644  1.00  0.00           H  
HETATM   48  H21 UNL     1       5.507  -1.112  -1.576  1.00  0.00           H  
HETATM   49  H22 UNL     1       3.771  -1.057  -1.766  1.00  0.00           H  
HETATM   50  H23 UNL     1       4.549  -2.034  -0.410  1.00  0.00           H  
HETATM   51  H24 UNL     1       5.230   0.783   1.719  1.00  0.00           H  
HETATM   52  H25 UNL     1       4.446  -0.909   1.713  1.00  0.00           H  
HETATM   53  H26 UNL     1       6.993  -0.482   3.131  1.00  0.00           H  
HETATM   54  H27 UNL     1      -3.135   1.209  -2.040  1.00  0.00           H  
HETATM   55  H28 UNL     1      -2.781  -0.500  -2.462  1.00  0.00           H  
HETATM   56  H29 UNL     1      -4.863   0.643  -3.525  1.00  0.00           H  
HETATM   57  H30 UNL     1      -5.320  -1.420  -3.769  1.00  0.00           H  
HETATM   58  H31 UNL     1      -6.796   1.026  -2.112  1.00  0.00           H  
HETATM   59  H32 UNL     1      -5.364   1.526  -1.069  1.00  0.00           H  
HETATM   60  H33 UNL     1      -6.567  -1.247  -1.057  1.00  0.00           H  
HETATM   61  H34 UNL     1      -7.911  -0.255   0.415  1.00  0.00           H  
CONECT    1    2    2   28   29
CONECT    2    3   26
CONECT    3    4    4   22
CONECT    4    5   30
CONECT    5    6    6   31
CONECT    6    7   12
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   36   37
CONECT   10   11   12   15
CONECT   11   38   39   40
CONECT   12   13   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   46
CONECT   16   17   18   47
CONECT   17   48   49   50
CONECT   18   19   51   52
CONECT   19   20   20   21
CONECT   21   53
CONECT   22   23   54   55
CONECT   23   24   25   56
CONECT   24   57
CONECT   25   26   58   59
CONECT   26   27   60
CONECT   27   61
END

HMDB0006472
     RDKit          3D
Calcitroic acid
 61 63  0  0  0  0  0  0  0  0999 V2000
   -4.8283   -1.5976    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8409   -0.7446    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910   -0.1997   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6112   -0.0516    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    0.4923   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    0.6643    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4143    0.3146    2.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    0.7291    2.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167    0.1465    2.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0841    0.1888    0.6005 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5982   -1.1149    0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609    1.1998    0.2760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1596    1.3043   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727    1.3268   -1.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    0.8343   -0.0455 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5245    0.1543   -0.1858 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5497   -1.1030   -0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0948   -0.1590    1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4283   -0.8156    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0520   -1.0880    0.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9905   -1.1360    2.3699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4945    0.1529   -1.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8708    0.0913   -2.5517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1566   -1.2598   -2.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8803    0.6971   -1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1658   -0.3580   -0.5450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0109    0.1364    0.4370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -1.9237    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274   -2.0266    1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -0.3056    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1998    0.7613   -1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    0.9825    2.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -0.7316    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.4546    3.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0064    1.8365    2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    0.6916    2.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -0.9146    2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304   -1.3243    0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755   -1.2152   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809   -1.9214    0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357    2.1774    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    2.2293   -1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    0.4644   -1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9763    2.3840   -1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9963    0.7404   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4329    1.7844    0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2243    0.8807   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5075   -1.1124   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714   -1.0574   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5494   -2.0342   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2297    0.7829    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -0.9087    1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9929   -0.4819    3.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355    1.2092   -2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -0.5002   -2.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    0.6431   -3.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3202   -1.4201   -3.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7963    1.0263   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3635    1.5264   -1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5667   -1.2472   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9112   -0.2549    0.4147 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  1  0
 19 20  2  0
 19 21  1  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26  2  1  0
 12  6  1  0
 15 10  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  1
 16 47  1  6
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  6
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  6
 27 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Calcitroate	Generator
(3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoate	HMDB
(3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acid	HMDB
(3R)-3-[(1R,3AS,4E,7ar)-4-[(2Z)-2-[(3R,5S)-3,5-dihydroxy-2 methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoate	HMDB
(3R)-3-[(1R,3AS,4E,7ar)-4-[(2Z)-2-[(3R,5S)-3,5-dihydroxy-2 methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoic acid	HMDB
1 alpha-Hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)	HMDB
1a-Hydroxycalcioate	HMDB
1a-Hydroxycalcioic acid	HMDB
1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-Oate	HMDB
1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-Oic acid	HMDB
1alpha-Hydroxy-23-carboxytetranorvitamin D	HMDB
Calcitroic acid (D3)	HMDB
1 alpha,3 beta-Dihydroxy-24-nor-9,10- seco-5,7,10(19)-cholatrien-23-Oic acid	HMDB
1 alpha-Hydroxy-23-carboxytetranorvitamin D	HMDB
(3R)-3-[(1R,3AS,4E,7ar)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoate	HMDB
Calcitroic acid	HMDB

Chemical Formula

C₂₃H₃₄O₄

Average Molecular Weight

374.5137

Monoisotopic Molecular Weight

374.245709576

IUPAC Name

(3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoic acid

Traditional Name

(3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]butanoic acid

CAS Registry Number

71204-89-2

SMILES

[H][C@@]12CC[C@H]([C@H](C)CC(O)=O)[C@@]1(C)CCC\C2=C/C=C1\C[C@@H](O)C[C@H](O)C1=C

InChI Identifier

InChI=1S/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7+/t14-,18-,19-,20+,21+,23-/m1/s1

InChI Key

MBLYZRMZFUWLOZ-WLWRUGSRSA-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

Polycyclic triterpenoid
Triterpenoid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006472)

Organ

Liver (HMDB: HMDB0006472)
Kidney (HMDB: HMDB0006472)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006472)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006472)

Source

Endogenous

Endogenous (HMDB: HMDB0006472)

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)

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	0.031 g/L	ALOGPS
logP	4.1	ALOGPS
logP	2.88	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.91	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.01 m³·mol⁻¹	ChemAxon
Polarizability	43.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.755	31661259
DarkChem	[M-H]-	183.298	31661259
DeepCCS	[M-2H]-	234.654	30932474
DeepCCS	[M+Na]+	210.165	30932474
AllCCS	[M+H]+	196.4	32859911
AllCCS	[M+H-H2O]+	193.8	32859911
AllCCS	[M+NH4]+	198.7	32859911
AllCCS	[M+Na]+	199.4	32859911
AllCCS	[M-H]-	196.2	32859911
AllCCS	[M+Na-2H]-	197.3	32859911
AllCCS	[M+HCOO]-	198.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.75 minutes	32390414
Predicted by Siyang on May 30, 2022	15.068 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.2 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2674.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	617.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	685.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1245.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	514.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1571.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	419.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	444.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	287.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	337.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Calcitroic acid	[H][C@@]12CC[C@H]([C@H](C)CC(O)=O)[C@@]1(C)CCC\C2=C/C=C1\C[C@@H](O)C[C@H](O)C1=C	4591.5	Standard polar	33892256
Calcitroic acid	[H][C@@]12CC[C@H]([C@H](C)CC(O)=O)[C@@]1(C)CCC\C2=C/C=C1\C[C@@H](O)C[C@H](O)C1=C	3031.5	Standard non polar	33892256
Calcitroic acid	[H][C@@]12CC[C@H]([C@H](C)CC(O)=O)[C@@]1(C)CCC\C2=C/C=C1\C[C@@H](O)C[C@H](O)C1=C	3411.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Calcitroic acid,1TMS,isomer #1	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O	3222.9	Semi standard non polar	33892256
Calcitroic acid,1TMS,isomer #2	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O	3166.9	Semi standard non polar	33892256
Calcitroic acid,1TMS,isomer #3	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C	3180.8	Semi standard non polar	33892256
Calcitroic acid,2TMS,isomer #1	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O	3158.3	Semi standard non polar	33892256
Calcitroic acid,2TMS,isomer #2	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C	3166.1	Semi standard non polar	33892256
Calcitroic acid,2TMS,isomer #3	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	3125.4	Semi standard non polar	33892256
Calcitroic acid,3TMS,isomer #1	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	3137.6	Semi standard non polar	33892256
Calcitroic acid,1TBDMS,isomer #1	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O	3469.8	Semi standard non polar	33892256
Calcitroic acid,1TBDMS,isomer #2	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O	3374.8	Semi standard non polar	33892256
Calcitroic acid,1TBDMS,isomer #3	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3374.7	Semi standard non polar	33892256
Calcitroic acid,2TBDMS,isomer #1	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O	3611.7	Semi standard non polar	33892256
Calcitroic acid,2TBDMS,isomer #2	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3600.3	Semi standard non polar	33892256
Calcitroic acid,2TBDMS,isomer #3	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	3536.7	Semi standard non polar	33892256
Calcitroic acid,3TBDMS,isomer #1	C=C1/C(=C/C=C2\CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC(=O)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	3764.5	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 - Calcitroic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1039000000-1f88c71835fdec009978	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calcitroic acid GC-MS (3 TMS) - 70eV, Positive	splash10-004i-1100290000-baa5a03a90d912185f1c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calcitroic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calcitroic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 10V, Positive-QTOF	splash10-0a70-0019000000-cb5546f5b2dabfd4d572	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 20V, Positive-QTOF	splash10-01p9-0459000000-b307bdc6f267458bae7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 40V, Positive-QTOF	splash10-006t-2692000000-5836da83c653fc8f7abb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 10V, Negative-QTOF	splash10-00di-0009000000-f06abff6056eb86b8f3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 20V, Negative-QTOF	splash10-0c00-1009000000-ddade7030a96941096fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 40V, Negative-QTOF	splash10-0a4i-7309000000-add77990ddb49e71f86d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 10V, Positive-QTOF	splash10-00kr-0389000000-7f28baeb8809349c3201	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 20V, Positive-QTOF	splash10-014r-0192000000-29b56ddbc29d3acf9008	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 40V, Positive-QTOF	splash10-05mx-3970000000-cea41e29508e68bf1125	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 10V, Negative-QTOF	splash10-00di-0009000000-2ede4546d5bd0240a5eb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 20V, Negative-QTOF	splash10-0bvi-6009000000-fa722a798506a9889a5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calcitroic acid 40V, Negative-QTOF	splash10-006x-8926000000-85a3cc1c3ea55c628074	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023930

KNApSAcK ID

Not Available

Chemspider ID

17216369

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2290389

Wikipedia Link

Calcitroic acid

METLIN ID

Not Available

PubChem Compound

12918533

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Sakaki T; Sawada N; Nonaka Y; Ohyama Y; Inouye K Metabolic studies using recombinant escherichia coli cells producing rat mitochondrial CYP24 CYP24 can convert 1alpha,25-dihydroxyvitamin D3 to calcitroic acid. European journal of biochemistry / FEBS (1999), 262(1), 43-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Reddy GS, Tserng KY: Calcitroic acid, end product of renal metabolism of 1,25-dihydroxyvitamin D3 through C-24 oxidation pathway. Biochemistry. 1989 Feb 21;28(4):1763-9. [PubMed:2719932 ]
Siu-Caldera ML, Zou L, Ehrlich MG, Schwartz ER, Ishizuka S, Reddy GS: Human osteoblasts in culture metabolize both 1 alpha, 25-dihydroxyvitamin D3 and its precursor 25-hydroxyvitamin D3 into their respective lactones. Endocrinology. 1995 Oct;136(10):4195-203. [PubMed:7664636 ]

Showing metabocard for Calcitroic acid (HMDB0006472)

MOL for HMDB0006472 (Calcitroic acid)

3D MOL for HMDB0006472 (Calcitroic acid)

3D SDF for HMDB0006472 (Calcitroic acid)

3D-SDF for HMDB0006472 (Calcitroic acid)

PDB for HMDB0006472 (Calcitroic acid)

3D PDB for HMDB0006472 (Calcitroic acid)

SMILES for HMDB0006472 (Calcitroic acid)

INCHI for HMDB0006472 (Calcitroic acid)

Structure for HMDB0006472 (Calcitroic acid)

3D Structure for HMDB0006472 (Calcitroic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra