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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-12 23:14:06 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003533

Secondary Accession Numbers

HMDB0006263
HMDB03533
HMDB06263

Metabolite Identification

Common Name

3a,7a,12a-Trihydroxy-5b-cholestan-26-al

Description

3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-al is an intermediate in bile acid biosynthesis. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and 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. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). 3a,7a,12a-trihydroxy-5b-cholestane-27-al is an enzymatically generated intermediate in the oxidation process of 5b-cholestane-3a,7a,12a,27-tetrol into 3a,7a,12a-trihydroxy-5b-cholestanoic acid in liver mitochondria. Mitochondrial sterol 27-hydroxylase (EC 1.14.13.60) appears to perform multiple monooxygenations in this conversion. (PMID: 8496170 ).

Structure

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

  Mrv0541 02231219452D          

 36 39  0  0  1  0            999 V2000
   23.4310  -13.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1635  -16.8830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7415  -16.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7127  -11.8145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2275  -13.2791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.3546  -11.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0347  -13.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0982  -12.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2910  -12.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5413  -12.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8037  -10.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1906  -13.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0174  -14.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1906  -14.3145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.0110  -15.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.4761  -13.9020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4894  -16.4112    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.4575  -16.4229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.9711  -14.0632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4761  -15.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.7618  -15.1395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.0043  -16.4170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.1906  -15.1395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.7618  -14.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7486  -16.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2327  -16.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2464  -15.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4644  -15.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4526  -14.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9711  -15.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1618  -11.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7133  -13.9608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.1179  -16.1255    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4684  -14.7418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.0069  -17.0769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.7338  -15.7281    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  6  0  0  0
 17  2  1  6  0  0  0
 18  3  1  6  0  0  0
  4 31  2  0  0  0  0
  5  7  1  0  0  0  0
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  6 11  1  0  0  0  0
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  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
 14 12  1  1  0  0  0
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 14 19  1  0  0  0  0
 14 23  1  0  0  0  0
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 15 27  1  0  0  0  0
 16 24  1  0  0  0  0
 17 20  1  0  0  0  0
 17 25  1  0  0  0  0
 18 26  1  0  0  0  0
 18 28  1  0  0  0  0
 19 29  1  0  0  0  0
 19 32  1  6  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 20 33  1  1  0  0  0
 21 24  1  0  0  0  0
 21 34  1  6  0  0  0
 22 25  1  0  0  0  0
 22 26  1  0  0  0  0
 22 35  1  1  0  0  0
 23 30  1  0  0  0  0
 23 36  1  6  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0003533
     RDKit          3D
3a,7a,12a-Trihydroxy-5b-cholestan-26-al
 77 80  0  0  0  0  0  0  0  0999 V2000
    7.0288    1.4417    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6003    0.0802    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8156   -0.7178   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1311   -1.7243    0.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8568    0.3201   -1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    1.1658   -1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5812    0.6442   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730   -0.5458   -0.6050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6749   -1.7918   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420   -0.9197    0.1255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7456   -1.2206    1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2973   -1.1564    2.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2655   -0.8605   -2.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3680    2.0913   -0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9555   -0.4427    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4450   -0.3682   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169    0.8392   -1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710   -0.6526   -1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0533    2.1522   -0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8676    1.5039    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5003   -1.9434   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8865   -2.0229   -1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0629   -2.2844    1.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4241   -1.9536    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4247   -0.4328   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4664   -0.8396    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3675    0.9175    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 74  1  0
 29 75  1  0
 30 76  1  1
 31 77  1  0
M  END

  Mrv0541 02231219452D          

 36 39  0  0  1  0            999 V2000
   23.4310  -13.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1635  -16.8830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7415  -16.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7127  -11.8145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2275  -13.2791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.3546  -11.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0347  -13.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.5413  -12.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.2464  -15.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4644  -15.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4526  -14.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9711  -15.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1618  -11.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7133  -13.9608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.1179  -16.1255    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4684  -14.7418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.0069  -17.0769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.7338  -15.7281    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  6  0  0  0
 17  2  1  6  0  0  0
 18  3  1  6  0  0  0
  4 31  2  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  6  0  0  0
  5 19  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  6 31  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
 14 12  1  1  0  0  0
 15 13  1  1  0  0  0
 14 16  1  0  0  0  0
 14 19  1  0  0  0  0
 14 23  1  0  0  0  0
 15 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 27  1  0  0  0  0
 16 24  1  0  0  0  0
 17 20  1  0  0  0  0
 17 25  1  0  0  0  0
 18 26  1  0  0  0  0
 18 28  1  0  0  0  0
 19 29  1  0  0  0  0
 19 32  1  6  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 20 33  1  1  0  0  0
 21 24  1  0  0  0  0
 21 34  1  6  0  0  0
 22 25  1  0  0  0  0
 22 26  1  0  0  0  0
 22 35  1  1  0  0  0
 23 30  1  0  0  0  0
 23 36  1  6  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003533

> <DATABASE_NAME>
hmdb

> <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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h15-25,29-31H,5-14H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
USFJGINJGUIFSY-XZULNKEGSA-N

> <FORMULA>
C27H46O4

> <MOLECULAR_WEIGHT>
434.6517

> <EXACT_MASS>
434.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
52.41570405546709

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
3.7560018126666685

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.071715106969688

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15943465417462444

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
123.64039999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003533
     RDKit          3D
3a,7a,12a-Trihydroxy-5b-cholestan-26-al
 77 80  0  0  0  0  0  0  0  0999 V2000
    7.0288    1.4417    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6003    0.0802    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8156   -0.7178   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1311   -1.7243    0.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8568    0.3201   -1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    1.1658   -1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5812    0.6442   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730   -0.5458   -0.6050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6749   -1.7918   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420   -0.9197    0.1255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7456   -1.2206    1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2973   -1.1564    2.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917   -0.9920    0.8345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8705   -0.5108    0.9623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3935    0.1105   -0.2914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4339    0.9835   -1.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235    0.2503   -1.2342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2655   -0.8605   -2.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -0.0227    0.0946 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5758    1.2339    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6966    0.8106    0.0066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5238    2.1336    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3525    1.0951   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7958    1.4837   -1.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5112    0.2680   -0.5957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2864   -0.7878   -1.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9765    0.0864    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5109   -0.1040    0.8806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1356   -1.5589    0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374   -1.7681    1.1927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1649   -2.7794    0.4157 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1849    1.9033    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8723    1.3231    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3680    2.0913   -0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9555   -0.4427    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4450   -0.3682   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169    0.8392   -1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710   -0.6526   -1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0533    2.1522   -0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2407    1.5340   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8676    1.5039    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0583    0.5168    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5014   -0.2790   -1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5003   -1.9434   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8865   -2.0229   -1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636   -2.6674   -0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2880   -1.8947   -0.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0629   -2.2844    1.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -0.5154    2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1491   -0.2478    2.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0277   -2.0557    2.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -1.9536    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0303    0.1754    1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -0.7238   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357    1.9631   -0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8524    1.1585   -2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    0.9649   -1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163   -1.5027   -1.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218    1.3320    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097    2.1117    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038    1.1968    1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935    2.4050    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551    2.1174    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0435    2.9720    0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921    1.9266   -1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3229    0.1679   -1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1734    1.7337   -2.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9404    2.3063   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5998    0.4507   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4247   -0.4328   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4664   -0.8396    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3675    0.9175    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111    0.1381    1.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8123   -2.1534    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2825   -1.8956   -0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842   -2.0865    2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -3.5860    0.9411 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  1
 15 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 19 10  1  0
 28 21  1  0
 19 13  1  0
 30 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  6
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  6
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  6
 14 53  1  1
 15 54  1  6
 16 55  1  0
 16 56  1  0
 17 57  1  6
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 25 69  1  1
 26 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  1
 29 74  1  0
 29 75  1  0
 30 76  1  1
 31 77  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      43.738 -24.705   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      45.105 -31.515   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      36.851 -31.421   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      53.597 -22.054   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      47.091 -24.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      51.062 -21.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.598 -24.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      50.583 -22.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.077 -23.006   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.810 -23.852   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.034 -20.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.156 -25.223   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.099 -27.501   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      45.156 -26.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      41.087 -29.041   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      43.822 -25.950   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      43.847 -30.634   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.187 -30.656   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      46.613 -26.251   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      43.822 -29.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      42.489 -28.260   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.075 -30.645   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.156 -28.260   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      42.489 -26.720   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      42.464 -31.447   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      39.634 -31.491   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      39.660 -28.172   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      38.200 -28.985   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      47.512 -27.490   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      46.613 -28.730   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      52.569 -20.908   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      47.998 -26.060   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      45.020 -30.101   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      43.808 -27.518   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      41.080 -31.877   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      46.170 -29.359   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   31                                                            
CONECT    5    7   10   19                                                  
CONECT    6    8   11   31                                                  
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12   14                                                            
CONECT   13   15                                                            
CONECT   14   12   16   19   23                                             
CONECT   15   13   21   22   27                                             
CONECT   16    1   14   24                                                  
CONECT   17    2   20   25                                                  
CONECT   18    3   26   28                                                  
CONECT   19    5   14   29   32                                             
CONECT   20   17   21   23   33                                             
CONECT   21   15   20   24   34                                             
CONECT   22   15   25   26   35                                             
CONECT   23   14   20   30   36                                             
CONECT   24   16   21                                                       
CONECT   25   17   22                                                       
CONECT   26   18   22                                                       
CONECT   27   15   28                                                       
CONECT   28   18   27                                                       
CONECT   29   19   30                                                       
CONECT   30   23   29                                                       
CONECT   31    4    6                                                       
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   21                                                            
CONECT   35   22                                                            
CONECT   36   23                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0003533
HETATM    1  C1  UNL     1       7.029   1.442   0.641  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.600   0.080   0.108  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.816  -0.718  -0.206  1.00  0.00           C  
HETATM    4  O1  UNL     1       8.131  -1.724   0.390  1.00  0.00           O  
HETATM    5  C4  UNL     1       5.857   0.320  -1.215  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.653   1.166  -1.024  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.581   0.644  -0.140  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.873  -0.546  -0.605  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.675  -1.792  -0.818  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.642  -0.920   0.125  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.746  -1.221   1.578  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.297  -1.156   2.110  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.492  -0.992   0.835  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.870  -0.511   0.962  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.394   0.111  -0.291  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.434   0.984  -1.020  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.124   0.250  -1.234  1.00  0.00           C  
HETATM   18  O2  UNL     1      -0.266  -0.861  -2.024  1.00  0.00           O  
HETATM   19  C17 UNL     1       0.465  -0.023   0.095  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.576   1.234   0.917  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.697   0.811   0.007  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.524   2.134   0.714  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.352   1.095  -1.321  1.00  0.00           C  
HETATM   24  C22 UNL     1      -5.796   1.484  -1.200  1.00  0.00           C  
HETATM   25  C23 UNL     1      -6.511   0.268  -0.596  1.00  0.00           C  
HETATM   26  O3  UNL     1      -6.286  -0.788  -1.447  1.00  0.00           O  
HETATM   27  C24 UNL     1      -5.976   0.086   0.782  1.00  0.00           C  
HETATM   28  C25 UNL     1      -4.511  -0.104   0.881  1.00  0.00           C  
HETATM   29  C26 UNL     1      -4.136  -1.559   0.685  1.00  0.00           C  
HETATM   30  C27 UNL     1      -2.737  -1.768   1.193  1.00  0.00           C  
HETATM   31  O4  UNL     1      -2.165  -2.779   0.416  1.00  0.00           O  
HETATM   32  H1  UNL     1       6.185   1.903   1.210  1.00  0.00           H  
HETATM   33  H2  UNL     1       7.872   1.323   1.344  1.00  0.00           H  
HETATM   34  H3  UNL     1       7.368   2.091  -0.189  1.00  0.00           H  
HETATM   35  H4  UNL     1       5.955  -0.443   0.827  1.00  0.00           H  
HETATM   36  H5  UNL     1       8.445  -0.368  -1.015  1.00  0.00           H  
HETATM   37  H6  UNL     1       6.617   0.839  -1.881  1.00  0.00           H  
HETATM   38  H7  UNL     1       5.671  -0.653  -1.663  1.00  0.00           H  
HETATM   39  H8  UNL     1       5.053   2.152  -0.590  1.00  0.00           H  
HETATM   40  H9  UNL     1       4.241   1.534  -2.012  1.00  0.00           H  
HETATM   41  H10 UNL     1       2.868   1.504   0.002  1.00  0.00           H  
HETATM   42  H11 UNL     1       4.058   0.517   0.875  1.00  0.00           H  
HETATM   43  H12 UNL     1       2.501  -0.279  -1.668  1.00  0.00           H  
HETATM   44  H13 UNL     1       4.500  -1.943  -0.127  1.00  0.00           H  
HETATM   45  H14 UNL     1       3.886  -2.023  -1.889  1.00  0.00           H  
HETATM   46  H15 UNL     1       2.964  -2.667  -0.557  1.00  0.00           H  
HETATM   47  H16 UNL     1       1.288  -1.895  -0.353  1.00  0.00           H  
HETATM   48  H17 UNL     1       2.063  -2.284   1.727  1.00  0.00           H  
HETATM   49  H18 UNL     1       2.319  -0.515   2.174  1.00  0.00           H  
HETATM   50  H19 UNL     1       0.149  -0.248   2.726  1.00  0.00           H  
HETATM   51  H20 UNL     1       0.028  -2.056   2.665  1.00  0.00           H  
HETATM   52  H21 UNL     1      -0.424  -1.954   0.288  1.00  0.00           H  
HETATM   53  H22 UNL     1      -2.030   0.175   1.820  1.00  0.00           H  
HETATM   54  H23 UNL     1      -2.668  -0.724  -0.997  1.00  0.00           H  
HETATM   55  H24 UNL     1      -1.236   1.963  -0.593  1.00  0.00           H  
HETATM   56  H25 UNL     1      -1.852   1.159  -2.046  1.00  0.00           H  
HETATM   57  H26 UNL     1       0.548   0.965  -1.783  1.00  0.00           H  
HETATM   58  H27 UNL     1      -0.916  -1.503  -1.696  1.00  0.00           H  
HETATM   59  H28 UNL     1      -0.422   1.332   1.452  1.00  0.00           H  
HETATM   60  H29 UNL     1       0.610   2.112   0.261  1.00  0.00           H  
HETATM   61  H30 UNL     1       1.304   1.197   1.731  1.00  0.00           H  
HETATM   62  H31 UNL     1      -2.493   2.405   0.942  1.00  0.00           H  
HETATM   63  H32 UNL     1      -4.055   2.117   1.712  1.00  0.00           H  
HETATM   64  H33 UNL     1      -4.043   2.972   0.167  1.00  0.00           H  
HETATM   65  H34 UNL     1      -3.792   1.927  -1.800  1.00  0.00           H  
HETATM   66  H35 UNL     1      -4.323   0.168  -1.958  1.00  0.00           H  
HETATM   67  H36 UNL     1      -6.173   1.734  -2.192  1.00  0.00           H  
HETATM   68  H37 UNL     1      -5.940   2.306  -0.455  1.00  0.00           H  
HETATM   69  H38 UNL     1      -7.600   0.451  -0.525  1.00  0.00           H  
HETATM   70  H39 UNL     1      -6.425  -0.433  -2.382  1.00  0.00           H  
HETATM   71  H40 UNL     1      -6.466  -0.840   1.205  1.00  0.00           H  
HETATM   72  H41 UNL     1      -6.367   0.918   1.412  1.00  0.00           H  
HETATM   73  H42 UNL     1      -4.211   0.138   1.944  1.00  0.00           H  
HETATM   74  H43 UNL     1      -4.812  -2.153   1.346  1.00  0.00           H  
HETATM   75  H44 UNL     1      -4.282  -1.896  -0.352  1.00  0.00           H  
HETATM   76  H45 UNL     1      -2.684  -2.086   2.245  1.00  0.00           H  
HETATM   77  H46 UNL     1      -1.946  -3.586   0.941  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    5   35
CONECT    3    4    4   36
CONECT    5    6   37   38
CONECT    6    7   39   40
CONECT    7    8   41   42
CONECT    8    9   10   43
CONECT    9   44   45   46
CONECT   10   11   19   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   19   52
CONECT   14   15   30   53
CONECT   15   16   21   54
CONECT   16   17   55   56
CONECT   17   18   19   57
CONECT   18   58
CONECT   19   20
CONECT   20   59   60   61
CONECT   21   22   23   28
CONECT   22   62   63   64
CONECT   23   24   65   66
CONECT   24   25   67   68
CONECT   25   26   27   69
CONECT   26   70
CONECT   27   28   71   72
CONECT   28   29   73
CONECT   29   30   74   75
CONECT   30   31   76
CONECT   31   77
END

HMDB0003533
     RDKit          3D
3a,7a,12a-Trihydroxy-5b-cholestan-26-al
 77 80  0  0  0  0  0  0  0  0999 V2000
    7.0288    1.4417    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6003    0.0802    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8156   -0.7178   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1311   -1.7243    0.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8568    0.3201   -1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    1.1658   -1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5812    0.6442   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730   -0.5458   -0.6050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6749   -1.7918   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420   -0.9197    0.1255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7456   -1.2206    1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2973   -1.1564    2.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917   -0.9920    0.8345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8705   -0.5108    0.9623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3935    0.1105   -0.2914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4339    0.9835   -1.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235    0.2503   -1.2342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2655   -0.8605   -2.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -0.0227    0.0946 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5758    1.2339    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6966    0.8106    0.0066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5238    2.1336    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3525    1.0951   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7958    1.4837   -1.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5112    0.2680   -0.5957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2864   -0.7878   -1.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9765    0.0864    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5109   -0.1040    0.8806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1356   -1.5589    0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374   -1.7681    1.1927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1649   -2.7794    0.4157 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1849    1.9033    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8723    1.3231    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3680    2.0913   -0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9555   -0.4427    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4450   -0.3682   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169    0.8392   -1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710   -0.6526   -1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0533    2.1522   -0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2407    1.5340   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8676    1.5039    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0583    0.5168    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5014   -0.2790   -1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5003   -1.9434   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8865   -2.0229   -1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636   -2.6674   -0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2880   -1.8947   -0.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0629   -2.2844    1.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -0.5154    2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1491   -0.2478    2.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0277   -2.0557    2.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -1.9536    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0303    0.1754    1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -0.7238   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357    1.9631   -0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8524    1.1585   -2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    0.9649   -1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163   -1.5027   -1.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218    1.3320    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097    2.1117    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038    1.1968    1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935    2.4050    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551    2.1174    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0435    2.9720    0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921    1.9266   -1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3229    0.1679   -1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1734    1.7337   -2.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9404    2.3063   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5998    0.4507   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4247   -0.4328   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4664   -0.8396    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3675    0.9175    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111    0.1381    1.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8123   -2.1534    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2825   -1.8956   -0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842   -2.0865    2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -3.5860    0.9411 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  1
 15 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 19 10  1  0
 28 21  1  0
 19 13  1  0
 30 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  6
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  6
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  6
 14 53  1  1
 15 54  1  6
 16 55  1  0
 16 56  1  0
 17 57  1  6
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 25 69  1  1
 26 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  1
 29 74  1  0
 29 75  1  0
 30 76  1  1
 31 77  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-al	ChEBI
3,7,12-Trihydroxycholestan-26-al	ChEBI
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-al	Generator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-al	Generator
3 alpha,7-alpha,12 alpha-Trihydroxy-5 beta-cholestan-26-al	MeSH
(6R)-2-Methyl-6-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanal	HMDB
3-alpha-7-alpha-12-alpha-Trihydroxy-5-beta-cholestan-26-al	HMDB
3alpha,7-alpha,12alpha-Trihydroxy-5beta-cholestan-26-al	HMDB

Chemical Formula

C₂₇H₄₆O₄

Average Molecular Weight

434.6517

Monoisotopic Molecular Weight

434.33960996

IUPAC Name

(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal

Traditional Name

(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal

CAS Registry Number

3836-01-9

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

InChI Identifier

InChI=1S/C27H46O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h15-25,29-31H,5-14H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

USFJGINJGUIFSY-XZULNKEGSA-N

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

27-oxosteroid
26-oxosteroid
Trihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxide
Organic oxygen compound
Organooxygen compound
Aldehyde
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:16466 )
7alpha-hydroxy steroid (CHEBI:16466 )
cholestanoid (CHEBI:16466 )
12alpha-hydroxy steroid (CHEBI:16466 )
26-oxo steroid (CHEBI:16466 )
C27 bile acids, alcohols, and derivatives (C01301 )
C27 bile acids, alcohols, and derivatives (LMST04030164 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003533)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0003533)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003533)

Source

Endogenous

Endogenous (HMDB: HMDB0003533)

Animal

Animal (HMDB: HMDB0003533)

Exogenous

Food

Food (HMDB: HMDB0003533)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0003533)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0003533)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0003533)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)
Zellweger Syndrome (PathBank: SMP0120495)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0003533)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0003533)

Cellular process

Cell signaling (HMDB: HMDB0003533)

Biochemical process

Lipid transport (HMDB: HMDB0003533)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0003533)

Molecular messenger

Hormone (HMDB: HMDB0003533)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003533)

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	4.265	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.92	ALOGPS
logP	3.76	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	16.07	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.64 m³·mol⁻¹	ChemAxon
Polarizability	52.42 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	201.365	31661259
DarkChem	[M-H]-	194.995	31661259
DeepCCS	[M-2H]-	243.594	30932474
DeepCCS	[M+Na]+	217.612	30932474
AllCCS	[M+H]+	212.0	32859911
AllCCS	[M+H-H2O]+	210.2	32859911
AllCCS	[M+NH4]+	213.7	32859911
AllCCS	[M+Na]+	214.2	32859911
AllCCS	[M-H]-	205.9	32859911
AllCCS	[M+Na-2H]-	208.1	32859911
AllCCS	[M+HCOO]-	210.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3a,7a,12a-Trihydroxy-5b-cholestan-26-al	[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	2993.2	Standard polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al	[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	3576.6	Standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al	[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	3828.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TMS,isomer #1	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3496.3	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TMS,isomer #2	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3554.2	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TMS,isomer #3	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3547.2	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TMS,isomer #4	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3642.9	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #1	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3485.2	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #2	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3465.7	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #3	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3520.4	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #4	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3496.9	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #5	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3615.2	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #6	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3585.1	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TMS,isomer #1	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3469.0	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TMS,isomer #2	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3522.8	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TMS,isomer #3	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3519.8	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TMS,isomer #4	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3529.0	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TMS,isomer #1	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3514.7	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TMS,isomer #1	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3433.0	Standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TMS,isomer #1	CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3580.7	Standard polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TBDMS,isomer #1	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3720.9	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TBDMS,isomer #2	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3778.4	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TBDMS,isomer #3	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3775.3	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TBDMS,isomer #4	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3865.6	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #1	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3933.3	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #2	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3904.4	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #3	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3935.9	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #4	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3940.6	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #5	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4068.7	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #6	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4018.8	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TBDMS,isomer #1	CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4120.5	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TBDMS,isomer #2	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4159.0	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TBDMS,isomer #3	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4143.1	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TBDMS,isomer #4	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4188.6	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4374.2	Semi standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4147.6	Standard non polar	33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3848.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al GC-MS (Non-derivatized) - 70eV, Positive	splash10-05n0-0539800000-e17f084e0678cd71fce8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al GC-MS (3 TMS) - 70eV, Positive	splash10-000i-0313149000-8f4c3fec7b662dbf46d2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 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 - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 10V, Positive-QTOF	splash10-014j-0006900000-8f907fe536c81d1166ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 20V, Positive-QTOF	splash10-00kb-1019300000-780bb9b9d55b812930c4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 40V, Positive-QTOF	splash10-000i-2009000000-9b52601f913e3bbb4c0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 10V, Negative-QTOF	splash10-001i-0001900000-4383dce4ba8c45585b48	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 20V, Negative-QTOF	splash10-0159-0002900000-fbc50593e1905290155e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 40V, Negative-QTOF	splash10-0a4r-9005300000-07a48968e6731add21f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 10V, Positive-QTOF	splash10-00ks-1006900000-2471d92ac4c323289c67	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 20V, Positive-QTOF	splash10-000i-4249200000-0b7ecbecd8f67217ea56	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 40V, Positive-QTOF	splash10-0a4i-9621000000-17c980384d97d3d72a10	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 10V, Negative-QTOF	splash10-001i-0001900000-a283ea4f75f642471b3c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 20V, Negative-QTOF	splash10-001i-0001900000-d7676b1fba2f6b906efc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 40V, Negative-QTOF	splash10-001i-0023900000-ebbdce292f968247b51d	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Primary bile acid biosynthesis	Not Available
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

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

FDB023188

KNApSAcK ID

Not Available

Chemspider ID

388578

KEGG Compound ID

C01301

BioCyc ID

Not Available

BiGG ID

37315

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439479

PDB ID

Not Available

ChEBI ID

16466

Food Biomarker Ontology

Not Available

VMH ID

CE4872

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Dayal B; Tint G S; Batta A K; Shefer S; Salen G Synthesis of biological precursors of cholic acid II. Steroids (1981), 37(2), 205-11.

Material Safety Data Sheet (MSDS)

Not Available

General References

St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
Holmberg-Betsholtz I, Lund E, Bjorkhem I, Wikvall K: Sterol 27-hydroxylase in bile acid biosynthesis. Mechanism of oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid. J Biol Chem. 1993 May 25;268(15):11079-85. [PubMed:8496170 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

Enzyme Details

1. Sterol 26-hydroxylase, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:: CYP27A1
Uniprot ID:: Q02318
Molecular weight:: 60234.28

Reactions

27-Deoxy-5b-cyprinol → 3a,7a,12a-Trihydroxy-5b-cholestan-26-al	details
3a,7a,12a-Trihydroxy-5b-cholestan-26-al + NADPH + Oxygen + Hydrogen Ion → Coprocholic acid + NADP + Water	details

Showing metabocard for 3a,7a,12a-Trihydroxy-5b-cholestan-26-al (HMDB0003533)

MOL for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

3D MOL for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

3D SDF for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

3D-SDF for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

PDB for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

3D PDB for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

SMILES for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

INCHI for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

Structure for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

3D Structure for HMDB0003533 (3a,7a,12a-Trihydroxy-5b-cholestan-26-al)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions