NP-MRD: Showing NP-Card for Coprocholic acid (NP0086620)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:26:16 UTC

Updated at

2022-05-11 16:26:16 UTC

NP-MRD ID

NP0086620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coprocholic acid

Description

Coprocholic acid, also known as coprocholate, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. Coprocholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In humans, coprocholic acid is involved in the metabolic disorder called familial hypercholanemia (fhca). Coprocholic acid, with regard to humans, has been found to be associated with several diseases such as d-bifunctional protein deficiency and rhizomelic chondrodysplasia punctata; coprocholic acid has also been linked to several inborn metabolic disorders including infantile refsum's disease, refsum's disease, and peroxisomal biogenesis defect. Bile acids recirculate through the liver, bile ducts, small intestine, and the portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. Bile acids have potent toxic properties (e.G. Coprocholic acid was first documented in 2002 (PMID: 11980911). Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305231918412D          

 37 40  0  0  0  0            999 V2000
 9999.6406 9997.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.638510001.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3579 9997.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5003 9997.3127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5003 9999.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2131 9998.5598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.925710001.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6385 9998.5598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9257 9999.7948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.9081 9999.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4231 9999.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.423110000.4698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.423110001.2948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.138710001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.852310001.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.567910001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610001.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.997210001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.712810001.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.997210002.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610000.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.709010001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.138710000.8822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7855 9999.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0710 9998.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0710 9998.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7855 9997.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5000 9998.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5000 9998.9670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2127 9999.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2127 9997.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9272 9998.1432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9272 9998.9683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.925710000.6272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.211210000.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6402 9999.3896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.640210000.2147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 23  1  6  0  0  0
 13 14  1  0  0  0  0
 13 22  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 12  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 35  1  0  0  0  0
 34 37  1  0  0  0  0
 36 37  1  0  0  0  0
 34  7  1  6  0  0  0
 36 11  1  0  0  0  0
 12 37  1  0  0  0  0
 37  2  1  1  0  0  0
 36  8  1  6  0  0  0
 32  1  1  6  0  0  0
 35 30  1  0  0  0  0
 33 36  1  0  0  0  0
 30  6  1  6  0  0  0
 33  9  1  1  0  0  0
 26  3  1  6  0  0  0
 30 29  1  0  0  0  0
 28 31  1  0  0  0  0
 28  4  1  1  0  0  0
 29  5  1  1  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
    6.1939   -1.0479   -2.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9926   -1.6612   -0.7676 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9059   -0.9569    0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.4875    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1781    1.2274    1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    1.4216    0.6366 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7557    2.2988   -0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402    0.3272    0.4676 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8251   -0.6299    1.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -1.1695    1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2058   -0.6882    0.5084 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6695   -0.7688    0.4604 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3438    0.2344   -0.4065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6971    1.5911   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867    1.4067   -0.6663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1400    0.5516   -1.7747 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    0.7407    0.5201 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0157    1.5022    1.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900    0.3036   -0.0146 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0304    0.9846    1.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5698    1.1093   -1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9945    1.1835   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5945   -0.1564   -0.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7092   -0.3220   -1.1440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6630   -1.2870   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010   -1.1400    0.0268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3620   -2.0504   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137   -2.1491   -0.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0838   -2.3710   -1.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2290   -1.7677    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6635   -2.8988    0.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9990   -0.6842    0.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8326   -1.7442   -2.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7463   -0.0955   -2.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2364   -0.9571   -2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6109   -2.7061   -0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9559   -1.4501    1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166   -1.2217   -0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4947    1.0124   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1577    0.5022    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6371    2.2726    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2616    0.8141    2.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991    2.1356    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    3.2527   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881    1.7537   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8307    2.4340   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -0.2576   -0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186   -0.0715    2.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544   -1.4446    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -2.2623    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479   -0.7238    2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3105   -1.2163   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0638   -0.8044    1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3207   -0.1013   -1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    2.1713   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8800    2.1690    0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1420    2.4333   -0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3620    1.0262   -2.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495    1.4961    2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1648    2.5867    1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9370    1.0998    2.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2929    0.7116    2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9416    2.0775    1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0276    0.6999    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1494    2.1323   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4560    0.6696   -2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5680    1.7323   -1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133    1.8138    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9990   -0.2484    0.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3890    0.3404   -0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5482   -1.4202   -1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1145   -2.2138   -0.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2812   -1.5192    1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8306   -3.0741   -0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3520   -1.8229   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948   -2.9471    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934   -2.3019   -2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6995   -0.3544   -0.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 28  1  0
 28 29  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  1  1
 19 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  1
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 30  1  0
 30 32  1  0
 30 31  2  0
 17  8  1  0
 17 11  1  0
 13 12  1  0
 19 26  1  0
  8 47  1  6
  9 48  1  0
  9 49  1  0
 10 50  1  0
 10 51  1  0
 11 52  1  6
 12 53  1  1
 28 76  1  1
 29 77  1  0
 27 74  1  0
 27 75  1  0
 26 73  1  1
 25 71  1  0
 25 72  1  0
 23 69  1  1
 24 70  1  0
 22 67  1  0
 22 68  1  0
 21 65  1  0
 21 66  1  0
 20 62  1  0
 20 63  1  0
 20 64  1  0
 13 54  1  6
 14 55  1  0
 14 56  1  0
 15 57  1  6
 16 58  1  0
 18 59  1  0
 18 60  1  0
 18 61  1  0
  6 43  1  1
  7 44  1  0
  7 45  1  0
  7 46  1  0
  5 41  1  0
  5 42  1  0
  4 39  1  0
  4 40  1  0
  3 37  1  0
  3 38  1  0
  2 36  1  6
  1 33  1  0
  1 34  1  0
  1 35  1  0
 32 78  1  0
M  END


  Mrv1652305231918412D          

 37 40  0  0  0  0            999 V2000
 9999.6406 9997.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.638510001.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3579 9997.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5003 9997.3127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5003 9999.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2131 9998.5598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.925710001.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6385 9998.5598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9257 9999.7948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.9081 9999.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4231 9999.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.423110000.4698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.423110001.2948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.138710001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.852310001.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.567910001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610001.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.997210001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.712810001.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.997210002.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610000.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.709010001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.138710000.8822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7855 9999.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0710 9998.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0710 9998.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7855 9997.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5000 9998.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5000 9998.9670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2127 9999.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2127 9997.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9272 9998.1432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9272 9998.9683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.925710000.6272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.211210000.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6402 9999.3896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.640210000.2147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 23  1  6  0  0  0
 13 14  1  0  0  0  0
 13 22  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 12  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 35  1  0  0  0  0
 34 37  1  0  0  0  0
 36 37  1  0  0  0  0
 34  7  1  6  0  0  0
 36 11  1  0  0  0  0
 12 37  1  0  0  0  0
 37  2  1  1  0  0  0
 36  8  1  6  0  0  0
 32  1  1  6  0  0  0
 35 30  1  0  0  0  0
 33 36  1  0  0  0  0
 30  6  1  6  0  0  0
 33  9  1  1  0  0  0
 26  3  1  6  0  0  0
 30 29  1  0  0  0  0
 28 31  1  0  0  0  0
 28  4  1  1  0  0  0
 29  5  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0086620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

> <INCHI_KEY>
CNWPIIOQKZNXBB-VCVMUKOKSA-N

> <FORMULA>
C27H46O5

> <MOLECULAR_WEIGHT>
450.6511

> <EXACT_MASS>
450.334524582

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.32339719269413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.9146180650000013

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.618758291832509

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15944064032502225

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
124.5658

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  O   UNK     0    8665.9968662.422   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8665.9928668.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.0018662.422   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8662.0018661.650   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0    8662.0018666.284   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0    8663.3318663.978   0.000  0.00  0.00           H+0
HETATM    7  O   UNK     0    8664.6618669.391   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8665.9928663.978   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8664.6618666.284   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8668.3628666.298   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.4568665.052   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.4568667.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.4568669.084   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.7928669.853   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.1248669.084   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8671.4608669.853   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8672.7928669.084   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8674.1288669.853   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8675.4648669.084   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8674.1288671.393   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8672.7928667.544   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.1238669.853   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0    8668.7928668.313   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0    8660.6668665.508   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8659.3338664.738   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8659.3338663.198   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8660.6668662.428   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8662.0008663.198   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8662.0008664.738   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8663.3308665.511   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8663.3308662.431   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8664.6648663.201   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8664.6648664.741   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8664.6618667.837   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8663.3288667.067   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8665.9958665.527   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8665.9958667.067   0.000  0.00  0.00           C+0
CONECT    1   32                                                            
CONECT    2   37                                                            
CONECT    3   26                                                            
CONECT    4   28                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7   34                                                            
CONECT    8   36                                                            
CONECT    9   33                                                            
CONECT   10   11   12                                                       
CONECT   11   10   36                                                       
CONECT   12   13   23   10   37                                             
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   13                                                            
CONECT   23   12                                                            
CONECT   24   25   29                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27    3                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31    4                                             
CONECT   29   24   28   30    5                                             
CONECT   30   33   35    6   29                                             
CONECT   31   32   28                                                       
CONECT   32   31   33    1                                                  
CONECT   33   30   32   36    9                                             
CONECT   34   35   37    7                                                  
CONECT   35   34   30                                                       
CONECT   36   37   11    8   33                                             
CONECT   37   34   36   12    2                                             
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oic acid	ChEBI
3,7,12-Trihydroxycholestan-26-Oic acid	ChEBI
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-Oate	Generator
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-Oic acid	Generator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oate	Generator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oate	Generator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oic acid	Generator
3,7,12-Trihydroxycholestan-26-Oate	Generator
Coprocholate	Generator
3a,7a,12a-Trihydroxy-(6ci,7ci,8ci)5b-cholestan-26-Oate	HMDB
3a,7a,12a-Trihydroxy-(6ci,7ci,8ci)5b-cholestan-26-Oic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholestan-26-Oate	HMDB
3a,7a,12a-Trihydroxy-5b-cholestan-26-Oic acid	HMDB
3a,7a,12a-Trihydroxycoprostanate	HMDB
3a,7a,12a-Trihydroxycoprostanic acid	HMDB
5b-Cholestane-3a,7a,12a-triol-26-Oate	HMDB
5b-Cholestane-3a,7a,12a-triol-26-Oic acid	HMDB
3 alpha,7 alpha,12 alpha-Trihydroxy-5-beta-cholestan-26-Oic acid	HMDB
3,7,12-Trihydroxycholestan-26-Oic acid, (25R)-isomer	HMDB
3,7,12-Trihydroxycholestan-26-Oic acid, (25S)-isomer	HMDB
3Α,7α,12α-trihydroxy-5β-cholestan-26-Oic acid	HMDB
3Α,7α,12α-trihydroxycoprostanic acid	HMDB
5Β-cholestane-3α,7α,12α-triol-26-Oic acid	HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-Oic acid	HMDB
3alpha,7alpha,12alpha-Trihydroxycoprostanic acid	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha-triol-26-Oic acid	HMDB
Trihydroxycoprostanic acid	HMDB
Trihydroxycoprostanoic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholestanoic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholestanoate	HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoate	HMDB
3Α,7α,12α-trihydroxy-5β-cholestanoate	HMDB
3Α,7α,12α-trihydroxy-5β-cholestanoic acid	HMDB
Coprocholic acid	HMDB, ChEBI

Chemical Formula

C₂₇H₄₆O₅

Average Mass

450.6511 Da

Monoisotopic Mass

450.33452 Da

IUPAC Name

(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

Traditional Name

(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(O)=O

InChI Identifier

InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

InChI Key

CNWPIIOQKZNXBB-VCVMUKOKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Trihydroxy bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:18402 )
hydroxy monocarboxylic acid (CHEBI:18402 )
7alpha-hydroxy steroid (CHEBI:18402 )
12alpha-hydroxy steroid (CHEBI:18402 )
steroid acid (CHEBI:18402 )
C27 bile acids, alcohols, and derivatives (LMST04030001 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.12	ALOGPS
logP	3.91	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.57 m³·mol⁻¹	ChemAxon
Polarizability	53.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000601

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022137

KNApSAcK ID

Not Available

Chemspider ID

109066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5577

PubChem Compound

122312

PDB ID

Not Available

ChEBI ID

18402

Good Scents ID

Not Available

References

General References

Mihalik SJ, Steinberg SJ, Pei Z, Park J, Kim DG, Heinzer AK, Dacremont G, Wanders RJ, Cuebas DA, Smith KD, Watkins PA: Participation of two members of the very long-chain acyl-CoA synthetase family in bile acid synthesis and recycling. J Biol Chem. 2002 Jul 5;277(27):24771-9. doi: 10.1074/jbc.M203295200. Epub 2002 Apr 29. [PubMed:11980911 ]

Showing NP-Card for Coprocholic acid (NP0086620)

MOL for NP0086620 (Coprocholic acid)

3D MOL for NP0086620 (Coprocholic acid)

3D SDF for NP0086620 (Coprocholic acid)

3D-SDF for NP0086620 (Coprocholic acid)

PDB for NP0086620 (Coprocholic acid)

3D PDB for NP0086620 (Coprocholic acid)

SMILES for NP0086620 (Coprocholic acid)

INCHI for NP0086620 (Coprocholic acid)

Structure for NP0086620 (Coprocholic acid)

3D Structure for NP0086620 (Coprocholic acid)