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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:26:32 UTC

Update Date

2022-03-07 02:55:39 UTC

HMDB ID

HMDB0038159

Secondary Accession Numbers

HMDB38159

Metabolite Identification

Common Name

Retrocalamin

Description

Retrocalamin belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Retrocalamin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, retrocalamin has been detected, but not quantified in, citrus and mandarin orange (clementine, tangerine). This could make retrocalamin a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 01251306392D          

 33 37  0  0  0  0            999 V2000
   -4.9381   -7.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525   -7.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525   -8.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -9.1450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2236   -8.7325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2236   -7.9074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5091   -7.4949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5091   -9.1450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7947   -8.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7947   -7.9074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3670   -9.1450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3670   -9.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525  -10.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -9.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -7.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802   -9.1449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -9.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -8.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236  -10.3825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3670   -8.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966   -5.4004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216   -5.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766   -6.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5091   -6.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -6.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0815   -8.7324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7959   -9.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7959   -9.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0814   -7.9074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525  -11.2075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5104  -10.3825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0814  -10.3825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0814  -11.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 10  1  0  0  0  0
 14  4  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 24  1  6  0  0  0
  6 15  1  6  0  0  0
  9 16  2  0  0  0  0
  8 17  1  1  0  0  0
  5 17  1  1  0  0  0
  4 18  1  1  0  0  0
 14 19  1  0  0  0  0
 11 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 21 25  1  0  0  0  0
 12 11  1  0  0  0  0
 26 11  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  6  0  0  0
 13 30  2  0  0  0  0
 28 31  2  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0038159
     RDKit          3D
Retrocalamin
 63 67  0  0  0  0  0  0  0  0999 V2000
   -5.5254   -0.3319    3.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685   -0.6224    2.5066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -1.4231    1.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3500   -1.9402    0.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9707   -1.6262    0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -0.7113   -0.4345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9805   -1.0863   -1.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -0.7642   -1.2649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5718   -2.1945   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9602    0.1965   -2.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    1.5461   -1.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8886    2.3395   -2.2283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489    1.9665   -0.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    3.2329   -1.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515    1.0195   -0.7517 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7773    1.3671   -2.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -0.3855   -0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -1.2845   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662   -0.7893   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    0.2293    0.5529 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7287   -0.4889    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551    0.9168    0.7169 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5201    0.1250    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2533    0.1928   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2910   -0.7089   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2073   -1.3022    0.4780 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1838   -0.8368    1.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    1.4944    2.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0720    2.0116    2.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052    2.2665    3.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858    2.2473    1.3766 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5065    2.6819    0.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842    1.2935    0.3998 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7026    0.7779    3.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4276   -0.8035    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255   -0.5157    4.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -1.4852    1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009   -2.6799    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2047    0.3030   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2749   -1.9963   -1.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4175   -2.8471   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6011   -2.4224   -2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8946   -2.3085   -2.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    0.1088   -3.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.0640   -2.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017    2.0300    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    3.8999   -0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413    0.5378   -2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205    2.0959   -2.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    1.9100   -1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5030   -0.6106    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145   -2.2934   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -1.4147   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -1.6857   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7714   -0.4185   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5697   -1.5787    1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5707   -0.3898    2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8380   -0.1142    2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    1.8167    0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0320    0.8475   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0462   -0.8923   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8888   -1.1518    2.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0921    2.7139    1.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 33 32  1  6
 17  8  1  0
 33 20  1  0
 33 15  1  0
 27 23  2  0
 33 31  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  1
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 13 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  6
 24 60  1  0
 25 61  1  0
 27 62  1  0
 31 63  1  1
M  END


  Mrv0541 01251306392D          

 33 37  0  0  0  0            999 V2000
   -4.9381   -7.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525   -7.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525   -8.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -9.1450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2236   -8.7325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2236   -7.9074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5091   -7.4949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5091   -9.1450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7947   -8.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7947   -7.9074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3670   -9.1450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3670   -9.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525  -10.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -9.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -7.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802   -9.1449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -9.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -8.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236  -10.3825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3670   -8.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966   -5.4004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216   -5.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766   -6.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5091   -6.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -6.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0815   -8.7324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7959   -9.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7959   -9.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0814   -7.9074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6525  -11.2075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5104  -10.3825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0814  -10.3825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0814  -11.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 10  1  0  0  0  0
 14  4  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 24  1  6  0  0  0
  6 15  1  6  0  0  0
  9 16  2  0  0  0  0
  8 17  1  1  0  0  0
  5 17  1  1  0  0  0
  4 18  1  1  0  0  0
 14 19  1  0  0  0  0
 11 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 21 25  1  0  0  0  0
 12 11  1  0  0  0  0
 26 11  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  6  0  0  0
 13 30  2  0  0  0  0
 28 31  2  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038159

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C[C@H](O)[C@@]1(C)CC(=O)C(O)[C@]2(C)C1CC[C@@]1(C)[C@@H](OC(=O)[C@H]3O[C@@]213)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O9/c1-21(15(26)9-16(27)30-4)10-13(25)17(28)23(3)14(21)5-7-22(2)18(12-6-8-31-11-12)32-20(29)19-24(22,23)33-19/h6,8,11,14-15,17-19,26,28H,5,7,9-10H2,1-4H3/t14?,15-,17?,18-,19+,21-,22-,23-,24+/m0/s1

> <INCHI_KEY>
HMNKPIJMXBZMJF-IHGWNHGOSA-N

> <FORMULA>
C24H30O9

> <MOLECULAR_WEIGHT>
462.4896

> <EXACT_MASS>
462.188982558

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.50843394569763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (3S)-3-[(1R,2S,6S,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoate

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.2051429293333338

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.427936520358564

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.859083527018669

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0538626234323525

> <JCHEM_POLAR_SURFACE_AREA>
135.79999999999998

> <JCHEM_REFRACTIVITY>
110.54499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3S)-3-[(1R,2S,6S,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038159
     RDKit          3D
Retrocalamin
 63 67  0  0  0  0  0  0  0  0999 V2000
   -5.5254   -0.3319    3.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685   -0.6224    2.5066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -1.4231    1.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3500   -1.9402    0.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9707   -1.6262    0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -0.7113   -0.4345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9805   -1.0863   -1.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -0.7642   -1.2649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5718   -2.1945   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9602    0.1965   -2.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    1.5461   -1.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8886    2.3395   -2.2283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489    1.9665   -0.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    3.2329   -1.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515    1.0195   -0.7517 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7773    1.3671   -2.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -0.3855   -0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -1.2845   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662   -0.7893   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    0.2293    0.5529 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7287   -0.4889    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551    0.9168    0.7169 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5201    0.1250    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2533    0.1928   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2910   -0.7089   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2073   -1.3022    0.4780 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1838   -0.8368    1.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    1.4944    2.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0720    2.0116    2.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052    2.2665    3.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858    2.2473    1.3766 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5065    2.6819    0.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842    1.2935    0.3998 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7026    0.7779    3.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4276   -0.8035    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255   -0.5157    4.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -1.4852    1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009   -2.6799    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2047    0.3030   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2749   -1.9963   -1.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4175   -2.8471   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6011   -2.4224   -2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8946   -2.3085   -2.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    0.1088   -3.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.0640   -2.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017    2.0300    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    3.8999   -0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413    0.5378   -2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205    2.0959   -2.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    1.9100   -1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5030   -0.6106    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145   -2.2934   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -1.4147   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -1.6857   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7714   -0.4185   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5697   -1.5787    1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5707   -0.3898    2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8380   -0.1142    2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    1.8167    0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0320    0.8475   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0462   -0.8923   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8888   -1.1518    2.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0921    2.7139    1.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 33 32  1  6
 17  8  1  0
 33 20  1  0
 33 15  1  0
 27 23  2  0
 33 31  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  1
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 13 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  6
 24 60  1  0
 25 61  1  0
 27 62  1  0
 31 63  1  1
M  END

HEADER    PROTEIN                                 25-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-13         0                                  
HETATM    1  C   UNK     0      -9.218 -13.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.551 -14.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.551 -16.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.218 -17.071   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.884 -16.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.884 -14.760   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.550 -13.990   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.550 -17.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.217 -16.301   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.217 -14.760   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -11.885 -17.071   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -11.885 -18.611   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.551 -19.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.218 -18.611   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.884 -13.220   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.883 -17.070   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -7.884 -17.841   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -9.218 -15.531   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.884 -19.381   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -11.885 -15.530   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.780 -10.081   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.320 -10.081   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.796 -11.545   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.550 -12.450   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.305 -11.545   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -13.219 -16.300   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -14.552 -17.071   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -14.552 -18.611   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -13.219 -14.760   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -10.551 -20.921   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -15.886 -19.381   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -13.219 -19.381   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -13.219 -20.921   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    5   14    3   18                                             
CONECT    5    4    6    8   17                                             
CONECT    6    1    7    5   15                                             
CONECT    7    6   10   24                                                  
CONECT    8    5    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9    7                                                       
CONECT   11    3   20   12   26                                             
CONECT   12   13   11                                                       
CONECT   13   12   14   30                                                  
CONECT   14    4   13   19                                                  
CONECT   15    6                                                            
CONECT   16    9                                                            
CONECT   17    8    5                                                       
CONECT   18    4                                                            
CONECT   19   14                                                            
CONECT   20   11                                                            
CONECT   21   22   25                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24    7   23   25                                                  
CONECT   25   24   21                                                       
CONECT   26   11   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   31   32                                                  
CONECT   29   26                                                            
CONECT   30   13                                                            
CONECT   31   28                                                            
CONECT   32   28   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

COMPND    HMDB0038159
HETATM    1  C1  UNL     1      -5.525  -0.332   3.222  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.369  -0.622   2.507  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.298  -1.423   1.379  1.00  0.00           C  
HETATM    4  O2  UNL     1      -5.350  -1.940   0.950  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.971  -1.626   0.737  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.909  -0.711  -0.434  1.00  0.00           C  
HETATM    7  O3  UNL     1      -3.981  -1.086  -1.288  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.677  -0.764  -1.265  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.572  -2.194  -1.793  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.960   0.197  -2.427  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.045   1.546  -1.805  1.00  0.00           C  
HETATM   12  O4  UNL     1      -2.889   2.339  -2.228  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.149   1.966  -0.695  1.00  0.00           C  
HETATM   14  O5  UNL     1      -0.612   3.233  -1.031  1.00  0.00           O  
HETATM   15  C10 UNL     1       0.051   1.019  -0.752  1.00  0.00           C  
HETATM   16  C11 UNL     1       0.777   1.367  -2.016  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.407  -0.385  -0.642  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.772  -1.285  -1.033  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.066  -0.789  -0.511  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.012   0.229   0.553  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.729  -0.489   1.874  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.355   0.917   0.717  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.520   0.125   0.417  1.00  0.00           C  
HETATM   24  C19 UNL     1       5.253   0.193  -0.776  1.00  0.00           C  
HETATM   25  C20 UNL     1       6.291  -0.709  -0.697  1.00  0.00           C  
HETATM   26  O6  UNL     1       6.207  -1.302   0.478  1.00  0.00           O  
HETATM   27  C21 UNL     1       5.184  -0.837   1.151  1.00  0.00           C  
HETATM   28  O7  UNL     1       3.324   1.494   2.025  1.00  0.00           O  
HETATM   29  C22 UNL     1       2.072   2.012   2.397  1.00  0.00           C  
HETATM   30  O8  UNL     1       1.905   2.267   3.621  1.00  0.00           O  
HETATM   31  C23 UNL     1       0.986   2.247   1.377  1.00  0.00           C  
HETATM   32  O9  UNL     1       1.506   2.682   0.173  1.00  0.00           O  
HETATM   33  C24 UNL     1       0.984   1.293   0.400  1.00  0.00           C  
HETATM   34  H1  UNL     1      -5.703   0.778   3.115  1.00  0.00           H  
HETATM   35  H2  UNL     1      -6.428  -0.803   2.783  1.00  0.00           H  
HETATM   36  H3  UNL     1      -5.426  -0.516   4.313  1.00  0.00           H  
HETATM   37  H4  UNL     1      -2.224  -1.485   1.509  1.00  0.00           H  
HETATM   38  H5  UNL     1      -3.001  -2.680   0.341  1.00  0.00           H  
HETATM   39  H6  UNL     1      -3.205   0.303  -0.088  1.00  0.00           H  
HETATM   40  H7  UNL     1      -4.275  -1.996  -1.120  1.00  0.00           H  
HETATM   41  H8  UNL     1      -1.418  -2.847  -0.928  1.00  0.00           H  
HETATM   42  H9  UNL     1      -2.601  -2.422  -2.202  1.00  0.00           H  
HETATM   43  H10 UNL     1      -0.895  -2.308  -2.632  1.00  0.00           H  
HETATM   44  H11 UNL     1      -1.245   0.109  -3.228  1.00  0.00           H  
HETATM   45  H12 UNL     1      -3.000  -0.064  -2.761  1.00  0.00           H  
HETATM   46  H13 UNL     1      -1.602   2.030   0.283  1.00  0.00           H  
HETATM   47  H14 UNL     1      -0.877   3.900  -0.359  1.00  0.00           H  
HETATM   48  H15 UNL     1       1.041   0.538  -2.660  1.00  0.00           H  
HETATM   49  H16 UNL     1       0.221   2.096  -2.671  1.00  0.00           H  
HETATM   50  H17 UNL     1       1.746   1.910  -1.797  1.00  0.00           H  
HETATM   51  H18 UNL     1      -0.503  -0.611   0.464  1.00  0.00           H  
HETATM   52  H19 UNL     1       0.515  -2.293  -0.627  1.00  0.00           H  
HETATM   53  H20 UNL     1       0.857  -1.415  -2.123  1.00  0.00           H  
HETATM   54  H21 UNL     1       2.614  -1.686  -0.090  1.00  0.00           H  
HETATM   55  H22 UNL     1       2.771  -0.419  -1.310  1.00  0.00           H  
HETATM   56  H23 UNL     1       1.570  -1.579   1.715  1.00  0.00           H  
HETATM   57  H24 UNL     1       2.571  -0.390   2.590  1.00  0.00           H  
HETATM   58  H25 UNL     1       0.838  -0.114   2.382  1.00  0.00           H  
HETATM   59  H26 UNL     1       3.313   1.817   0.033  1.00  0.00           H  
HETATM   60  H27 UNL     1       5.032   0.848  -1.617  1.00  0.00           H  
HETATM   61  H28 UNL     1       7.046  -0.892  -1.476  1.00  0.00           H  
HETATM   62  H29 UNL     1       4.889  -1.152   2.140  1.00  0.00           H  
HETATM   63  H30 UNL     1       0.092   2.714   1.812  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   37   38
CONECT    6    7    8   39
CONECT    7   40
CONECT    8    9   10   17
CONECT    9   41   42   43
CONECT   10   11   44   45
CONECT   11   12   12   13
CONECT   13   14   15   46
CONECT   14   47
CONECT   15   16   17   33
CONECT   16   48   49   50
CONECT   17   18   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   22   33
CONECT   21   56   57   58
CONECT   22   23   28   59
CONECT   23   24   27   27
CONECT   24   25   25   60
CONECT   25   26   61
CONECT   26   27
CONECT   27   62
CONECT   28   29
CONECT   29   30   30   31
CONECT   31   32   33   63
CONECT   32   33
END

HMDB0038159
     RDKit          3D
Retrocalamin
 63 67  0  0  0  0  0  0  0  0999 V2000
   -5.5254   -0.3319    3.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685   -0.6224    2.5066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -1.4231    1.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3500   -1.9402    0.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9707   -1.6262    0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -0.7113   -0.4345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9805   -1.0863   -1.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -0.7642   -1.2649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5718   -2.1945   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9602    0.1965   -2.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    1.5461   -1.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8886    2.3395   -2.2283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489    1.9665   -0.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    3.2329   -1.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515    1.0195   -0.7517 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7773    1.3671   -2.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -0.3855   -0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -1.2845   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662   -0.7893   -0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    0.2293    0.5529 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7287   -0.4889    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551    0.9168    0.7169 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5201    0.1250    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2533    0.1928   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2910   -0.7089   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2073   -1.3022    0.4780 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1838   -0.8368    1.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    1.4944    2.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0720    2.0116    2.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052    2.2665    3.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858    2.2473    1.3766 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5065    2.6819    0.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842    1.2935    0.3998 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7026    0.7779    3.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4276   -0.8035    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255   -0.5157    4.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -1.4852    1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009   -2.6799    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2047    0.3030   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2749   -1.9963   -1.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4175   -2.8471   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6011   -2.4224   -2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8946   -2.3085   -2.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    0.1088   -3.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.0640   -2.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017    2.0300    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    3.8999   -0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413    0.5378   -2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205    2.0959   -2.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    1.9100   -1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5030   -0.6106    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145   -2.2934   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -1.4147   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -1.6857   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7714   -0.4185   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5697   -1.5787    1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5707   -0.3898    2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8380   -0.1142    2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    1.8167    0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0320    0.8475   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0462   -0.8923   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8888   -1.1518    2.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0921    2.7139    1.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 33 32  1  6
 17  8  1  0
 33 20  1  0
 33 15  1  0
 27 23  2  0
 33 31  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  1
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 13 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  6
 24 60  1  0
 25 61  1  0
 27 62  1  0
 31 63  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl (3S)-3-[(1R,2S,6S,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoic acid	Generator

Chemical Formula

C₂₄H₃₀O₉

Average Molecular Weight

462.4896

Monoisotopic Molecular Weight

462.188982558

IUPAC Name

methyl (3S)-3-[(1R,2S,6S,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoate

Traditional Name

methyl (3S)-3-[(1R,2S,6S,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoate

CAS Registry Number

74729-98-9

SMILES

COC(=O)C[C@H](O)[C@@]1(C)CC(=O)C(O)[C@]2(C)C1CC[C@@]1(C)[C@@H](OC(=O)[C@H]3O[C@@]213)C1=COC=C1

InChI Identifier

InChI=1S/C24H30O9/c1-21(15(26)9-16(27)30-4)10-13(25)17(28)23(3)14(21)5-7-22(2)18(12-6-8-31-11-12)32-20(29)19-24(22,23)33-19/h6,8,11,14-15,17-19,26,28H,5,7,9-10H2,1-4H3/t14?,15-,17?,18-,19+,21-,22-,23-,24+/m0/s1

InChI Key

HMNKPIJMXBZMJF-IHGWNHGOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Delta_valerolactone
1,4-dioxepane
Beta-hydroxy acid
Fatty acid ester
Dioxepane
Delta valerolactone
Pyran
Oxane
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Furan
Methyl ester
Heteroaromatic compound
Cyclic alcohol
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Oxirane
Ether
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038159)
Cytoplasm (HMDB: HMDB0038159)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038159)

Source

Exogenous

Food

Food (HMDB: HMDB0038159)

Fruit

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0038159)

Not Available

Nutrient (HMDB: HMDB0038159)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038159)

Emulsifier (HMDB: HMDB0038159)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	197 - 199 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	1.51	ALOGPS
logP	1.21	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.8 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.54 m³·mol⁻¹	ChemAxon
Polarizability	46.51 Å³	ChemAxon
Number of Rings	5	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]+	203.526	31661259
DarkChem	[M-H]-	197.403	31661259
DeepCCS	[M-2H]-	251.382	30932474
DeepCCS	[M+Na]+	225.688	30932474
AllCCS	[M+H]+	207.4	32859911
AllCCS	[M+H-H2O]+	205.4	32859911
AllCCS	[M+NH4]+	209.3	32859911
AllCCS	[M+Na]+	209.8	32859911
AllCCS	[M-H]-	210.6	32859911
AllCCS	[M+Na-2H]-	211.7	32859911
AllCCS	[M+HCOO]-	213.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retrocalamin	COC(=O)C[C@H](O)[C@@]1(C)CC(=O)C(O)[C@]2(C)C1CC[C@@]1(C)[C@@H](OC(=O)[C@H]3O[C@@]213)C1=COC=C1	3962.1	Standard polar	33892256
Retrocalamin	COC(=O)C[C@H](O)[C@@]1(C)CC(=O)C(O)[C@]2(C)C1CC[C@@]1(C)[C@@H](OC(=O)[C@H]3O[C@@]213)C1=COC=C1	3211.6	Standard non polar	33892256
Retrocalamin	COC(=O)C[C@H](O)[C@@]1(C)CC(=O)C(O)[C@]2(C)C1CC[C@@]1(C)[C@@H](OC(=O)[C@H]3O[C@@]213)C1=COC=C1	3643.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Retrocalamin,1TMS,isomer #1	COC(=O)C[C@H](O[Si](C)(C)C)[C@@]1(C)CC(=O)C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3349.1	Semi standard non polar	33892256
Retrocalamin,1TMS,isomer #2	COC(=O)C[C@H](O)[C@@]1(C)CC(=O)C(O[Si](C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3370.5	Semi standard non polar	33892256
Retrocalamin,1TMS,isomer #3	COC(=O)C[C@H](O)[C@@]1(C)CC(O[Si](C)(C)C)=C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3267.0	Semi standard non polar	33892256
Retrocalamin,1TMS,isomer #4	COC(=O)C[C@H](O)[C@@]1(C)C=C(O[Si](C)(C)C)C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3288.7	Semi standard non polar	33892256
Retrocalamin,2TMS,isomer #1	COC(=O)C[C@H](O[Si](C)(C)C)[C@@]1(C)CC(=O)C(O[Si](C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3364.6	Semi standard non polar	33892256
Retrocalamin,2TMS,isomer #2	COC(=O)C[C@H](O[Si](C)(C)C)[C@@]1(C)CC(O[Si](C)(C)C)=C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3252.5	Semi standard non polar	33892256
Retrocalamin,2TMS,isomer #3	COC(=O)C[C@H](O[Si](C)(C)C)[C@@]1(C)C=C(O[Si](C)(C)C)C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3268.9	Semi standard non polar	33892256
Retrocalamin,2TMS,isomer #4	COC(=O)C[C@H](O)[C@@]1(C)CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]312	3276.3	Semi standard non polar	33892256
Retrocalamin,2TMS,isomer #5	COC(=O)C[C@H](O)[C@@]1(C)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3277.7	Semi standard non polar	33892256
Retrocalamin,3TMS,isomer #1	COC(=O)C[C@H](O[Si](C)(C)C)[C@@]1(C)CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]312	3282.3	Semi standard non polar	33892256
Retrocalamin,3TMS,isomer #1	COC(=O)C[C@H](O[Si](C)(C)C)[C@@]1(C)CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]312	3199.4	Standard non polar	33892256
Retrocalamin,3TMS,isomer #2	COC(=O)C[C@H](O[Si](C)(C)C)[C@@]1(C)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3292.6	Semi standard non polar	33892256
Retrocalamin,3TMS,isomer #2	COC(=O)C[C@H](O[Si](C)(C)C)[C@@]1(C)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3148.2	Standard non polar	33892256
Retrocalamin,1TBDMS,isomer #1	COC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC(=O)C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3586.5	Semi standard non polar	33892256
Retrocalamin,1TBDMS,isomer #2	COC(=O)C[C@H](O)[C@@]1(C)CC(=O)C(O[Si](C)(C)C(C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3593.0	Semi standard non polar	33892256
Retrocalamin,1TBDMS,isomer #3	COC(=O)C[C@H](O)[C@@]1(C)CC(O[Si](C)(C)C(C)(C)C)=C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3504.2	Semi standard non polar	33892256
Retrocalamin,1TBDMS,isomer #4	COC(=O)C[C@H](O)[C@@]1(C)C=C(O[Si](C)(C)C(C)(C)C)C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3526.9	Semi standard non polar	33892256
Retrocalamin,2TBDMS,isomer #1	COC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC(=O)C(O[Si](C)(C)C(C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3817.4	Semi standard non polar	33892256
Retrocalamin,2TBDMS,isomer #2	COC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC(O[Si](C)(C)C(C)(C)C)=C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3711.2	Semi standard non polar	33892256
Retrocalamin,2TBDMS,isomer #3	COC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(C)C=C(O[Si](C)(C)C(C)(C)C)C(O)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3719.1	Semi standard non polar	33892256
Retrocalamin,2TBDMS,isomer #4	COC(=O)C[C@H](O)[C@@]1(C)CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]312	3720.4	Semi standard non polar	33892256
Retrocalamin,2TBDMS,isomer #5	COC(=O)C[C@H](O)[C@@]1(C)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3739.0	Semi standard non polar	33892256
Retrocalamin,3TBDMS,isomer #1	COC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]312	3912.3	Semi standard non polar	33892256
Retrocalamin,3TBDMS,isomer #1	COC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]312	3856.5	Standard non polar	33892256
Retrocalamin,3TBDMS,isomer #2	COC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(C)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3934.4	Semi standard non polar	33892256
Retrocalamin,3TBDMS,isomer #2	COC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(C)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)[C@]2(C)C1CC[C@@]1(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@@]321	3763.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Retrocalamin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-8094700000-e84539d1a96b2eaacabc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retrocalamin GC-MS (2 TMS) - 70eV, Positive	splash10-0006-5113390000-b745844ba820a3979fbd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retrocalamin 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 - Retrocalamin 10V, Positive-QTOF	splash10-03ea-0002900000-f1e23378f7df0013eba9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 20V, Positive-QTOF	splash10-01pk-0025900000-08c8e7b2ad7562b5735c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 40V, Positive-QTOF	splash10-000b-9445100000-566a6c53026cd23c39e5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 10V, Negative-QTOF	splash10-02t9-1002900000-0ac5571702404b7a3a9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 20V, Negative-QTOF	splash10-046u-3003900000-4f227bb53fe349a4a1d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 40V, Negative-QTOF	splash10-00rb-9007200000-3d5b1406c177f3410edc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 10V, Negative-QTOF	splash10-03di-0007900000-865f5de2769a0391138f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 20V, Negative-QTOF	splash10-0a4r-1009100000-3340b864685e66abec2b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 40V, Negative-QTOF	splash10-0a4i-2009000000-abe26dfb1843e1cdafb0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 10V, Positive-QTOF	splash10-03di-1006900000-64b5150fba9dbb285ebc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 20V, Positive-QTOF	splash10-03xr-1009800000-2ec2e9e82b9dacc36b2a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrocalamin 40V, Positive-QTOF	splash10-0a4u-3029100000-c02424b4afd941bfde94	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017389

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

131752313

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

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Retrocalamin (HMDB0038159)

MOL for HMDB0038159 (Retrocalamin)

3D MOL for HMDB0038159 (Retrocalamin)

3D SDF for HMDB0038159 (Retrocalamin)

3D-SDF for HMDB0038159 (Retrocalamin)

PDB for HMDB0038159 (Retrocalamin)

3D PDB for HMDB0038159 (Retrocalamin)

SMILES for HMDB0038159 (Retrocalamin)

INCHI for HMDB0038159 (Retrocalamin)

Structure for HMDB0038159 (Retrocalamin)

3D Structure for HMDB0038159 (Retrocalamin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra