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Showing metabocard for 7-Dehydrocholesterol (HMDB0000032)

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enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0000032
Secondary Accession Numbers
  • HMDB00032
Metabolite Identification
Common Name7-Dehydrocholesterol
Description7-Dehydrocholesterol (7-DHC), also known as provitamin D3 or 5,7-cholestadien-3-b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrocholesterol is also classified as a sterol. 7-Dehydrocholesterol is known as a zoosterol, meaning that it is a sterol isolated from animals (to distinguish those sterols isolated from plants which are called phytosterols). 7-DHC functions in the serum as a cholesterol precursor and is photochemically converted to vitamin D3 in the skin. Therefore 7-DHC functions as provitamin-D3. The presence of 7-DHC in human skin enables humans and other mammals to manufacture vitamin D3 (cholecalciferol) from ultraviolet rays in the sun light, via an intermediate isomer pre-vitamin D3. 7-DHC absorbs UV light most effectively at wavelengths between 290 and 320 nm and, thus, the production of vitamin D3 will occur primarily at those wavelengths (PMID: 9625080 ). The two most important factors that govern the generation of pre-vitamin D3 are the quantity (intensity) and quality (appropriate wavelength) of the UVB irradiation reaching the 7-dehydrocholesterol deep in the stratum basale and stratum spinosum (PMID: 9625080 ). 7-DHC is also found in the milk of several mammalian species, including cows (PMID: 10999630 ; PMID: 225459 ). It was discovered by Nobel-laureate organic chemist Adolf Windaus. 7-DHC can be produced by animals and plants via different pathways (PMID: 23717318 ). It is not produced by fungi in significant amounts. 7-DHC is made by some algae and can also be produced by some bacteria.
Structure
Data?1582752108
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000032 (7-Dehydrocholesterol)

      
  Mrv1652305201900092D          

 31 34  0  0  0  0            999 V2000
 9999.976110001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8390 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5515 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9761 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1260 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1260 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8374 9999.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8374 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5518 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2664 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264410000.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549910000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5499 9999.5655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2644 9999.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.978910000.3905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9787 9999.5656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7634 9999.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2483 9999.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763410000.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763410001.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479210001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192710001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337810001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049910001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210001.0560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8  3  1  1  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10  2  1  1  0  0  0
 16 10  1  0  0  0  0
 13 17  2  0  0  0  0
 16  4  1  6  0  0  0
 22 23  1  0  0  0  0
 22 31  1  6  0  0  0
 23 24  1  0  0  0  0
 23 30  1  6  0  0  0
 24 25  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
 27 29  1  0  0  0  0
 22 18  1  0  0  0  0
 22 21  1  0  0  0  0
 14 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19  5  1  6  0  0  0
 18  1  1  1  0  0  0
M  END
Download

3D MOL for HMDB0000032 (7-Dehydrocholesterol)

Download
3D SDF for HMDB0000032 (7-Dehydrocholesterol)
      
  Mrv1652305201900092D          

 31 34  0  0  0  0            999 V2000
 9999.976110001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8390 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5515 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9761 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1260 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1260 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8374 9999.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8374 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5518 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2664 9998.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264410000.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549910000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5499 9999.5655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2644 9999.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.978910000.3905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9787 9999.5656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7634 9999.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2483 9999.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763410000.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763410001.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479210001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192710001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210001.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337810001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049910001.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210001.0560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8  3  1  1  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10  2  1  1  0  0  0
 16 10  1  0  0  0  0
 13 17  2  0  0  0  0
 16  4  1  6  0  0  0
 22 23  1  0  0  0  0
 22 31  1  6  0  0  0
 23 24  1  0  0  0  0
 23 30  1  6  0  0  0
 24 25  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
 27 29  1  0  0  0  0
 22 18  1  0  0  0  0
 22 21  1  0  0  0  0
 14 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19  5  1  6  0  0  0
 18  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000032

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
UCTLRSWJYQTBFZ-DDPQNLDTSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.01447282690572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

> <ALOGPS_LOGP>
7.30

> <JCHEM_LOGP>
6.707309549333335

> <ALOGPS_LOGS>
-6.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270805421445605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3681497086596925

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
121.46649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for HMDB0000032 (7-Dehydrocholesterol)
439423
  -OEChem-10221910583D

 72 75  0     1  0  0  0  0  0999 V2000
    7.5889   -1.2921   -0.6310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021    0.7115    0.6299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1272    0.7318   -0.7558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2884    0.7606    0.1986 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9475   -0.4419    0.1896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3950   -0.5994    1.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625    1.8563   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764    0.6816   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3055    1.7800   -0.9619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178   -0.3322    0.4563 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1295   -0.6864    1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    1.0870    1.2893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4254    1.9301    1.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2453    0.3965   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0708   -1.7807    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    1.4493   -1.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8291    0.4676    1.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7536    1.0882    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5931    1.2179   -1.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7408    0.2217   -0.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5946   -1.8761    0.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    0.0820    2.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666   -1.2381   -0.6746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2372   -0.2130    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6620   -0.1247   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1725   -1.4527   -1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1364   -2.5993   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3389   -1.8254   -2.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054   -0.1955   -1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263   -0.2235   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843   -1.3417   -0.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7356   -1.4639    0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163   -0.7112    2.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    1.7234   -2.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    2.8395   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6291    2.7753   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924    1.4534   -1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4047    0.0361    2.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -1.6747    1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129    2.0892    1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6577    2.0727    1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    2.8670    1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926    1.8194    2.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6955   -2.4025   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6966   -2.2384    1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7753    2.2085   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8982    0.6763    1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3130    1.4347    1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5313   -0.0821    2.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263    1.3355    1.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8720    1.9052    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231    1.7512   -2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1211    0.6240   -1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2362    0.8154   -0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0231   -1.4045    1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8996   -2.9286    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -0.9495    2.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0673    0.1131    3.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3497    0.3370    3.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8377   -1.7945   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5644   -0.4755   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746   -1.0129    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7099    0.6618   -1.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3397    0.1824    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8444   -2.2277   -0.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2113   -1.3002   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1161   -2.9114    0.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6534   -3.4760   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6430   -2.3161    0.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3150   -2.1117   -1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7916   -2.6795   -2.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2957   -0.9956   -2.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  1 65  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 29  1  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  4 30  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 31  1  0  0  0  0
  6 11  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  7  9  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  8 16  2  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 12 18  1  0  0  0  0
 12 22  1  0  0  0  0
 12 40  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 14 19  2  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 16 19  1  0  0  0  0
 16 46  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 18 24  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 19 52  1  0  0  0  0
 20 23  1  0  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 21 23  1  0  0  0  0
 21 55  1  0  0  0  0
 21 56  1  0  0  0  0
 22 57  1  0  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
 23 60  1  0  0  0  0
 24 25  1  0  0  0  0
 24 61  1  0  0  0  0
 24 62  1  0  0  0  0
 25 26  1  0  0  0  0
 25 63  1  0  0  0  0
 25 64  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 66  1  0  0  0  0
 27 67  1  0  0  0  0
 27 68  1  0  0  0  0
 27 69  1  0  0  0  0
 28 70  1  0  0  0  0
 28 71  1  0  0  0  0
 28 72  1  0  0  0  0
M  END
> <PUBCHEM_COMPOUND_CID>
439423

> <PUBCHEM_CONFORMER_RMSD>
0.8

> <PUBCHEM_CONFORMER_DIVERSEORDER>
1
9
3
4
8
6
5
2
7

> <PUBCHEM_MMFF94_PARTIAL_CHARGES>
13
1 -0.68
10 0.14
14 -0.28
16 -0.15
19 -0.15
20 0.14
23 0.28
3 0.14
46 0.15
5 0.14
52 0.15
65 0.4
8 -0.28

> <PUBCHEM_EFFECTIVE_ROTOR_COUNT>
6.8

> <PUBCHEM_PHARMACOPHORE_FEATURES>
9
1 1 acceptor
1 1 donor
1 22 hydrophobe
3 26 27 28 hydrophobe
5 12 18 24 25 26 hydrophobe
5 2 3 4 7 9 rings
6 10 14 15 20 21 23 rings
6 2 3 5 6 8 11 rings
6 5 8 10 14 16 19 rings

> <PUBCHEM_HEAVY_ATOM_COUNT>
28

> <PUBCHEM_ATOM_DEF_STEREO_COUNT>
7

> <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_DEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_UDEF_STEREO_COUNT>
0

> <PUBCHEM_ISOTOPIC_ATOM_COUNT>
0

> <PUBCHEM_COMPONENT_COUNT>
1

> <PUBCHEM_CACTVS_TAUTO_COUNT>
1

> <PUBCHEM_CONFORMER_ID>
0006B47F00000001

> <PUBCHEM_MMFF94_ENERGY>
85.8799

> <PUBCHEM_FEATURE_SELFOVERLAP>
45.771

> <PUBCHEM_SHAPE_FINGERPRINT>
10 15 15195559109034322802
10693767 8 17968369053330519962
11578080 2 18200034096577454328
11646440 116 13470687040389757554
11963148 33 17917987248412521247
12011746 2 16732993007235008128
12166972 35 18412545422459484225
12236239 1 18411705365458013300
12596602 18 17775002388343389177
12838862 33 17240481442952873764
13668630 136 18333450954383234359
13782708 43 18201718422882587087
14251764 18 10303804381026416481
14849402 71 11167642314118107307
14931854 50 16298390119892108722
15183329 4 17023177224392231577
15188451 53 17917708011634964509
15196674 1 17386575648547364236
15238133 3 10881402057995621582
16994733 274 11530780231621683230
17913733 40 12895362092599016789
18222031 100 18113615681467088824
200 152 18260835860272990353
20028762 73 18335699420991639530
21267235 1 17386587785819000800
21424621 283 10953455224328578989
21521239 73 18040713697270165339
21637258 2 18201996638485139077
21781051 124 16056889061088419284
22122407 14 8862649248888418631
221357 26 17748831778778605740
2215653 11 17240205425851000056
22393880 68 16660647409949006739
23522609 53 18125190227572967064
23559900 14 16950575401515083308
23569914 152 16304534066372871015
23569943 247 17624430679882103278
23576562 1 16081946973676923983
2838139 119 13551463792212397215
3004659 81 17821726160925346655
3009799 131 16370724837936136181
3178227 256 14476961198811189362
335352 9 17386018251200517152
3633792 109 18040155101981273349
392239 28 15913326923145429615
397830 11 16988265569235360163
4015057 19 17822582706691648489
4340502 62 13398630545794775044
439807 62 18336549443398171291
465052 167 17132113550305468168
59755656 215 16588023493870343688
6086070 43 18410568449224482617
7495541 125 17704070707023527969
999808 66 16415480441538593407

> <PUBCHEM_SHAPE_MULTIPOLES>
570.36
18.64
2.11
1.9
10.75
0.5
0.27
13.96
-6.6
1.15
-0.44
1.21
-0.18
-1.93

> <PUBCHEM_SHAPE_SELFOVERLAP>
1188.197

> <PUBCHEM_SHAPE_VOLUME>
324.2

> <PUBCHEM_COORDINATE_TYPE>
2
5
10

$$$$

Download
PDB for HMDB0000032 (7-Dehydrocholesterol)
HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0    8666.6228668.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6338666.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6368662.754   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.9638664.313   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8666.6228664.313   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8661.3028665.841   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.9688665.071   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.9688663.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3028662.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.6308665.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6308663.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.9638662.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2978663.531   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2948668.166   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9608667.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9608665.856   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.2948665.086   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.6278667.396   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.6278665.856   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.0928665.380   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.9978666.625   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.0928667.872   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0928669.412   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8669.4288670.178   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8670.7608669.412   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8672.0968670.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8673.4328669.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8674.7648670.178   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4328667.872   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8666.7608670.178   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0    8669.4288668.638   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   10                                                            
CONECT    3    8                                                            
CONECT    4   16                                                            
CONECT    5   19                                                            
CONECT    6    7   10                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    3                                                  
CONECT    9    8   11                                                       
CONECT   10   11    6    2   16                                             
CONECT   11   10   12    9                                                  
CONECT   12   11   13                                                       
CONECT   13   12   17                                                       
CONECT   14   15   18                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   10    4                                             
CONECT   17   16   13   19                                                  
CONECT   18   19   22   14    1                                             
CONECT   19   18   20   17    5                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   23   31   18   21                                             
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23                                                            
CONECT   31   22                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for HMDB0000032 (7-Dehydrocholesterol)
COMPND    https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D1(CC%5BC@@%5D2(... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  H   UNL     1      -2.130   0.337  -2.113  1.00  0.00           H  
HETATM    2  C   UNL     1      -1.927   0.546  -1.062  1.00  0.00           C  
HETATM    3  C   UNL     1      -1.925   2.076  -0.807  1.00  0.00           C  
HETATM    4  C   UNL     1      -0.474   2.447  -0.393  1.00  0.00           C  
HETATM    5  C   UNL     1       0.354   1.322  -1.017  1.00  0.00           C  
HETATM    6  H   UNL     1       0.451   1.462  -2.094  1.00  0.00           H  
HETATM    7  C   UNL     1       1.693   1.047  -0.393  1.00  0.00           C  
HETATM    8  C   UNL     1       2.215   1.887   0.478  1.00  0.00           C  
HETATM    9  C   UNL     1       3.519   1.617   1.091  1.00  0.00           C  
HETATM   10  C   UNL     1       4.186   0.513   0.800  1.00  0.00           C  
HETATM   11  C   UNL     1       5.534   0.286   1.462  1.00  0.00           C  
HETATM   12  C   UNL     1       6.556  -0.052   0.372  1.00  0.00           C  
HETATM   13  H   UNL     1       6.689   0.810  -0.281  1.00  0.00           H  
HETATM   14  O   UNL     1       7.806  -0.387   0.979  1.00  0.00           O  
HETATM   15  C   UNL     1       6.052  -1.241  -0.448  1.00  0.00           C  
HETATM   16  C   UNL     1       4.764  -0.855  -1.178  1.00  0.00           C  
HETATM   17  C   UNL     1       3.678  -0.523  -0.150  1.00  0.00           C  
HETATM   18  C   UNL     1       3.451  -1.796   0.668  1.00  0.00           C  
HETATM   19  C   UNL     1       2.372  -0.221  -0.828  1.00  0.00           C  
HETATM   20  H   UNL     1       2.604  -0.092  -1.885  1.00  0.00           H  
HETATM   21  C   UNL     1       1.427  -1.419  -0.767  1.00  0.00           C  
HETATM   22  C   UNL     1       0.066  -1.103  -1.410  1.00  0.00           C  
HETATM   23  C   UNL     1      -0.527   0.083  -0.692  1.00  0.00           C  
HETATM   24  C   UNL     1      -0.458  -0.155   0.818  1.00  0.00           C  
HETATM   25  C   UNL     1      -2.969  -0.140  -0.175  1.00  0.00           C  
HETATM   26  H   UNL     1      -2.761   0.088   0.871  1.00  0.00           H  
HETATM   27  C   UNL     1      -2.905  -1.653  -0.390  1.00  0.00           C  
HETATM   28  C   UNL     1      -4.364   0.369  -0.540  1.00  0.00           C  
HETATM   29  C   UNL     1      -5.392  -0.221   0.428  1.00  0.00           C  
HETATM   30  C   UNL     1      -6.788   0.288   0.062  1.00  0.00           C  
HETATM   31  C   UNL     1      -7.815  -0.302   1.030  1.00  0.00           C  
HETATM   32  C   UNL     1      -9.191   0.303   0.745  1.00  0.00           C  
HETATM   33  C   UNL     1      -7.877  -1.819   0.847  1.00  0.00           C  
HETATM   34  H   UNL     1      -2.203   2.607  -1.718  1.00  0.00           H  
HETATM   35  H   UNL     1      -2.619   2.322  -0.004  1.00  0.00           H  
HETATM   36  H   UNL     1      -0.188   3.414  -0.809  1.00  0.00           H  
HETATM   37  H   UNL     1      -0.370   2.447   0.692  1.00  0.00           H  
HETATM   38  H   UNL     1       1.675   2.784   0.744  1.00  0.00           H  
HETATM   39  H   UNL     1       3.940   2.328   1.787  1.00  0.00           H  
HETATM   40  H   UNL     1       5.842   1.190   1.987  1.00  0.00           H  
HETATM   41  H   UNL     1       5.461  -0.543   2.167  1.00  0.00           H  
HETATM   42  H   UNL     1       8.185   0.322   1.517  1.00  0.00           H  
HETATM   43  H   UNL     1       6.811  -1.526  -1.177  1.00  0.00           H  
HETATM   44  H   UNL     1       5.854  -2.082   0.217  1.00  0.00           H  
HETATM   45  H   UNL     1       4.949   0.017  -1.805  1.00  0.00           H  
HETATM   46  H   UNL     1       4.435  -1.687  -1.800  1.00  0.00           H  
HETATM   47  H   UNL     1       4.380  -2.081   1.162  1.00  0.00           H  
HETATM   48  H   UNL     1       2.682  -1.613   1.419  1.00  0.00           H  
HETATM   49  H   UNL     1       3.128  -2.600   0.007  1.00  0.00           H  
HETATM   50  H   UNL     1       1.883  -2.258  -1.293  1.00  0.00           H  
HETATM   51  H   UNL     1       1.272  -1.697   0.275  1.00  0.00           H  
HETATM   52  H   UNL     1       0.202  -0.857  -2.463  1.00  0.00           H  
HETATM   53  H   UNL     1      -0.598  -1.963  -1.313  1.00  0.00           H  
HETATM   54  H   UNL     1       0.581  -0.294   1.116  1.00  0.00           H  
HETATM   55  H   UNL     1      -0.875   0.706   1.341  1.00  0.00           H  
HETATM   56  H   UNL     1      -1.031  -1.047   1.072  1.00  0.00           H  
HETATM   57  H   UNL     1      -1.911  -2.016  -0.130  1.00  0.00           H  
HETATM   58  H   UNL     1      -3.647  -2.142   0.242  1.00  0.00           H  
HETATM   59  H   UNL     1      -3.113  -1.881  -1.436  1.00  0.00           H  
HETATM   60  H   UNL     1      -4.384   1.457  -0.473  1.00  0.00           H  
HETATM   61  H   UNL     1      -4.607   0.064  -1.558  1.00  0.00           H  
HETATM   62  H   UNL     1      -5.372  -1.308   0.360  1.00  0.00           H  
HETATM   63  H   UNL     1      -5.149   0.084   1.446  1.00  0.00           H  
HETATM   64  H   UNL     1      -6.807   1.376   0.130  1.00  0.00           H  
HETATM   65  H   UNL     1      -7.031  -0.017  -0.956  1.00  0.00           H  
HETATM   66  H   UNL     1      -7.523  -0.071   2.055  1.00  0.00           H  
HETATM   67  H   UNL     1      -9.483   0.073  -0.280  1.00  0.00           H  
HETATM   68  H   UNL     1      -9.923  -0.117   1.434  1.00  0.00           H  
HETATM   69  H   UNL     1      -9.148   1.384   0.876  1.00  0.00           H  
HETATM   70  H   UNL     1      -6.896  -2.250   1.050  1.00  0.00           H  
HETATM   71  H   UNL     1      -8.609  -2.240   1.536  1.00  0.00           H  
HETATM   72  H   UNL     1      -8.169  -2.050  -0.178  1.00  0.00           H  
CONECT    1    2                                                      
CONECT    2    1    3   23   25                                       
CONECT    3    2    4   34   35                                       
CONECT    4    3    5   36   37                                       
CONECT    5    4    6    7   23                                       
CONECT    6    5                                                      
CONECT    7    5    8    8   19                                       
CONECT    8    7    7    9   38                                       
CONECT    9    8   10   10   39                                       
CONECT   10    9    9   11   17                                       
CONECT   11   10   12   40   41                                       
CONECT   12   11   13   14   15                                       
CONECT   13   12                                                      
CONECT   14   12   42                                                 
CONECT   15   12   16   43   44                                       
CONECT   16   15   17   45   46                                       
CONECT   17   16   10   18   19                                       
CONECT   18   17   47   48   49                                       
CONECT   19   17    7   20   21                                       
CONECT   20   19                                                      
CONECT   21   19   22   50   51                                       
CONECT   22   21   23   52   53                                       
CONECT   23   22    2    5   24                                       
CONECT   24   23   54   55   56                                       
CONECT   25    2   26   27   28                                       
CONECT   26   25                                                      
CONECT   27   25   57   58   59                                       
CONECT   28   25   29   60   61                                       
CONECT   29   28   30   62   63                                       
CONECT   30   29   31   64   65                                       
CONECT   31   30   32   33   66                                       
CONECT   32   31   67   68   69                                       
CONECT   33   31   70   71   72                                       
CONECT   34    3                                                      
CONECT   35    3                                                      
CONECT   36    4                                                      
CONECT   37    4                                                      
CONECT   38    8                                                      
CONECT   39    9                                                      
CONECT   40   11                                                      
CONECT   41   11                                                      
CONECT   42   14                                                      
CONECT   43   15                                                      
CONECT   44   15                                                      
CONECT   45   16                                                      
CONECT   46   16                                                      
CONECT   47   18                                                      
CONECT   48   18                                                      
CONECT   49   18                                                      
CONECT   50   21                                                      
CONECT   51   21                                                      
CONECT   52   22                                                      
CONECT   53   22                                                      
CONECT   54   24                                                      
CONECT   55   24                                                      
CONECT   56   24                                                      
CONECT   57   27                                                      
CONECT   58   27                                                      
CONECT   59   27                                                      
CONECT   60   28                                                      
CONECT   61   28                                                      
CONECT   62   29                                                      
CONECT   63   29                                                      
CONECT   64   30                                                      
CONECT   65   30                                                      
CONECT   66   31                                                      
CONECT   67   32                                                      
CONECT   68   32                                                      
CONECT   69   32                                                      
CONECT   70   33                                                      
CONECT   71   33                                                      
CONECT   72   33                                                      
MASTER        0    0    0    0    0    0    0    0   72    0   72    0
END

Download
SMILES for HMDB0000032 (7-Dehydrocholesterol)
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
Download
INCHI for HMDB0000032 (7-Dehydrocholesterol)
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(3beta)-Cholesta-5,7-dien-3-olChEBI
5,7-Cholestadien-3-beta-olChEBI
5,7-Cholestadien-3beta-olChEBI
Provitamin D3ChEBI
Cholesta-5,7-dien-3beta-olKegg
(3b)-Cholesta-5,7-dien-3-olGenerator
(3Β)-cholesta-5,7-dien-3-olGenerator
5,7-Cholestadien-3-b-olGenerator
5,7-Cholestadien-3-β-olGenerator
5,7-Cholestadien-3b-olGenerator
5,7-Cholestadien-3β-olGenerator
Cholesta-5,7-dien-3b-olGenerator
Cholesta-5,7-dien-3β-olGenerator
(-)-7-DehydrocholesterolHMDB
10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
17-(1,5-Dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
5,7-Cholestandien-3-olHMDB
5,7-Cholestandien-3beta-olHMDB
7,8-dehydro-CholesterolHMDB
7,8-DidehydrocholesterolHMDB, MeSH
7-dehydro-CholesterolHMDB
7-DehydrocholesterinHMDB
7DHCHMDB
Cholesta-5,7-dien-3 beta -olHMDB
Cholesta-5,7-dien-3-beta-olHMDB
Cholesta-5,7-dien-3-olHMDB
DehydrocholesterinHMDB
DehydrocholesterolHMDB
Delta5,7-Cholestadien-3beta-olHMDB
Delta5,7-CholesterolHMDB
Delta7-CholesterolHMDB
Provitamin-D3HMDB
Provitamin D(3)MeSH, HMDB
Cholesta-5,7-dien-3 beta-olMeSH, HMDB
7-Dehydrocholesterol, (3beta,10alpha)-isomerMeSH, HMDB
7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomerMeSH, HMDB
7-DHCMeSH, HMDB
7-Dehydrocholesterol, (3alpha)-isomerMeSH, HMDB
7-Dehydrocholesterol, (3beta,9beta)-isomerMeSH, HMDB
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
Traditional Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
CAS Registry Number434-16-2
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
InChI KeyUCTLRSWJYQTBFZ-DDPQNLDTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassCholestane steroids  
Direct ParentCholesterols and derivatives  
Alternative Parents
Substituents
  • Cholesterol
    • 

  • Cholesterol-skeleton
    • 

  • 3-hydroxy-delta-5-steroid
    • 

  • 3-hydroxy-delta-7-steroid
    • 

  • 3-beta-hydroxysteroid
    • 

  • 3-beta-hydroxy-delta-5-steroid
    • 

  • 3-hydroxysteroid
    • 

  • Hydroxysteroid
    • 

  • Delta-7-steroid
    • 

  • Delta-5-steroid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect:
Disposition
Route of exposure:
Source:
Biological location:
Process
Naturally occurring process:
Role
Biological role:
Industrial application:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.3ALOGPS
logP6.71ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.47 m³·mol⁻¹ChemAxon
Polarizability50.01 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0axr-1019000000-73894a6c7b7346b2d1b02017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-002f-3005900000-c63a75d6ed190e98a35b2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ar0-1019000000-eadea32647b1133f95152021-09-05View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-124abe0c8995f883f0022012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05oa-4942000000-dbfe3e996983256b1e0c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05o0-5900000000-8115f37d8da9a1d6f5d82012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-000i-0090000000-3645f0c0605ff7c974052020-07-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-014r-0019000000-d2b535e3c3ed257f22152017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0ar9-3139000000-87132b4b12416fa4f01e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0a4i-5249000000-257a8915fd5fab2dfaaa2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-001i-0009000000-8ff4cced50a3c638abba2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-001i-0009000000-6d9a73d8f487e848e5382017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0ldi-1019000000-eb1f58f2c9df957166402017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-000i-0009000000-5cafb4a46516e1c4ca5a2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0ktr-9168000000-27f4addc4e70c9e3fc882021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-052f-9510000000-fce215a9f0a5b16bb81c2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-001i-0009000000-cf419f92ab7dfef8f2f82021-09-09View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, predicted)2012-12-04View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
    • 

  • Extracellular
    • 

  • Membrane
    • 

  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
    • 

  • Cerebrospinal Fluid (CSF)
    • 

  • Urine
Tissue Locations
  • Adrenal Gland
    • 

  • Brain
    • 

  • Epidermis
    • 

  • Fibroblasts
    • 

  • Liver
    • 

  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.65 uMChildren (1-13 years old)MaleNormal  details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
BloodDetected and Quantified5.0 +/- 2.2 uMAdult (>18 years old)BothNormal  details
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.02 uMAdult (>18 years old)BothNormal  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
UrineDetected and Quantified0.029 (0.0068-0.051) umol/mmol creatinineAdult (>18 years old)BothNormal  details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.21 uMChildren (1-13 years old)MaleLathosterolosis  details
BloodDetected and Quantified369.0 (46.0 - 1220.0) uMAdult (>18 years old)BothSmith-Lemli-Opitz syndrome  details
Cerebrospinal Fluid (CSF)Detected and Quantified0.3 +/- 0.2 (0.1 - 0.6) uMInfant (0-1 year old)BothSmith-Lemli-Opitz syndrome  details
Associated Disorders and Diseases
Disease References
Lathosterolosis
  1. Ho AC, Fung CW, Siu TS, Ma OC, Lam CW, Tam S, Wong VC: Lathosterolosis: a disorder of cholesterol biosynthesis resembling smith-lemli-opitz syndrome. JIMD Rep. 2014;12:129-34. doi: 10.1007/8904_2013_255. Epub 2013 Oct 20. [PubMed:24142275  ] 
Smith-Lemli-Opitz syndrome
  1. van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395  ] 
  2. Johnson DW, ten Brink HJ, Jakobs C: A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J Lipid Res. 2001 Oct;42(10):1699-705. [PubMed:11590227  ] 
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021882  
KNApSAcK IDC00023747  
Chemspider IDNot Available
KEGG Compound IDC01164  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link7-Dehydrocholesterol  
METLIN IDNot Available
PubChem Compound439423  
PDB IDNot Available
ChEBI ID17759  
Food Biomarker OntologyNot Available
VMH ID7DHCHSTEROL  
MarkerDB IDNot Available
References
Synthesis ReferenceWilliam G. Dauben, Jerome F. Eastham, and Robert A. Micheli   A new method for the preparation of 7-dehydrocholesterol. Journal of the American Chemical Society (1951), 73 4496.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lehmann B, Genehr T, Knuschke P, Pietzsch J, Meurer M: UVB-induced conversion of 7-dehydrocholesterol to 1alpha,25-dihydroxyvitamin D3 in an in vitro human skin equivalent model. J Invest Dermatol. 2001 Nov;117(5):1179-85. [PubMed:11710930  ] 
  2. Muzzin KB, Harper LF: Smith-Lemli-Opitz syndrome: a review, case report and dental implications. Spec Care Dentist. 2003;23(1):22-7. [PubMed:12887150  ] 
  3. Paterson CR, Moody JP, Pennington CR: Skin content of 7-dehydrocholesterol in patients with malabsorption. Nutrition. 1997 Sep;13(9):771-3. [PubMed:9290088  ] 
  4. Jira PE, Wevers RA, de Jong J, Rubio-Gozalbo E, Janssen-Zijlstra FS, van Heyst AF, Sengers RC, Smeitink JA: Simvastatin. A new therapeutic approach for Smith-Lemli-Opitz syndrome. J Lipid Res. 2000 Aug;41(8):1339-46. [PubMed:10946022  ] 
  5. Johnson DW, ten Brink HJ, Jakobs C: A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J Lipid Res. 2001 Oct;42(10):1699-705. [PubMed:11590227  ] 
  6. van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395  ] 
  7. Andersson HC, Frentz J, Martinez JE, Tuck-Muller CM, Bellizaire J: Adrenal insufficiency in Smith-Lemli-Opitz syndrome. Am J Med Genet. 1999 Feb 19;82(5):382-4. [PubMed:10069708  ] 
  8. GarciaFuentes E, icioso Recio MV, del Castillo Acedo Del Olmo E, atas Jurado MM, Arana Aguera M, Lopez Lopez J: [Biochemical diagnosis of Smith-Lemli-Opitz syndrome in a patient with congenital adrenal hyperplasia]. An Esp Pediatr. 2000 Nov;53(5):482-7. [PubMed:11141372  ] 
  9. Jezela-Stanek A, Malunowicz EM, Ciara E, Popowska E, Goryluk-Kozakiewicz B, Spodar K, Czerwiecka M, Jezuita J, Nowaczyk MJ, Krajewska-Walasek M: Maternal urinary steroid profiles in prenatal diagnosis of Smith-Lemli-Opitz syndrome: first patient series comparing biochemical and molecular studies. Clin Genet. 2006 Jan;69(1):77-85. [PubMed:16451140  ] 
  10. Moody JP, Humphries CA, Allan SM, Paterson CR: Determination of 7-dehydrocholesterol in human skin by high-performance liquid chromatography. J Chromatogr. 1990 Aug 24;530(1):19-27. [PubMed:2277111  ] 
  11. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  12. Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070  ] 
  13. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  14. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880  ] 
  15. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ] 
  16. O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372  ] 
  17. Norman AW: Sunlight, season, skin pigmentation, vitamin D, and 25-hydroxyvitamin D: integral components of the vitamin D endocrine system. Am J Clin Nutr. 1998 Jun;67(6):1108-10. doi: 10.1093/ajcn/67.6.1108. [PubMed:9625080  ] 
  18. Gomis DB, Fernandez MP, Gutierrez Alvarez MD: Simultaneous determination of fat-soluble vitamins and provitamins in milk by microcolumn liquid chromatography. J Chromatogr A. 2000 Sep 1;891(1):109-14. doi: 10.1016/s0021-9673(00)00623-3. [PubMed:10999630  ] 
  19. Adachi A, Kobayashi T: Identification of vitamin D3 and 7-dehydrocholesterol in cow's milk by gas chromatography-mass spectrometry and their quantitation by high-performance liquid chromatography. J Nutr Sci Vitaminol (Tokyo). 1979;25(2):67-78. doi: 10.3177/jnsv.25.67. [PubMed:225459  ] 
  20. Japelt RB, Jakobsen J: Vitamin D in plants: a review of occurrence, analysis, and biosynthesis. Front Plant Sci. 2013 May 13;4:136. doi: 10.3389/fpls.2013.00136. eCollection 2013. [PubMed:23717318  ] 
  21. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press. 
  22. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc.. 
Enzymes
  Enzyme Details
1. Hydroxymethylglutaryl-CoA synthase, mitochondrial
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.

Gene Name:
HMGCS2
Uniprot ID:
P54868  
Molecular weight:
52481.065
References
  1. Honda M, Tint GS, Honda A, Nguyen LB, Chen TS, Shefer S: 7-Dehydrocholesterol down-regulates cholesterol biosynthesis in cultured Smith-Lemli-Opitz syndrome skin fibroblasts. J Lipid Res. 1998 Mar;39(3):647-57. [PubMed:9548596  ] 
  Enzyme Details
2. Lathosterol oxidase
General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.

Gene Name:
SC5DL
Uniprot ID:
O75845  
Molecular weight:
35300.55
Reactions
Lathosterol + NAD(P)H + Oxygen → 7-Dehydrocholesterol + NAD(P)(+) + Waterdetails
Lathosterol + NADH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NAD + Waterdetails
Lathosterol + NADPH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NADP + Waterdetails
References
  1. Sugawara T, Fujimoto Y, Ishibashi T: Molecular cloning and structural analysis of human sterol C5 desaturase. Biochim Biophys Acta. 2001 Oct 31;1533(3):277-84. [PubMed:11731337  ] 
  Enzyme Details
3. Non-specific lipid-transfer protein
General function:
Involved in oxidoreductase activity
Specific function:
Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.

Gene Name:
SCP2
Uniprot ID:
P22307  
Molecular weight:
34974.505
References
  1. Morin RJ, Brun MJ, Srikantaiah MV: Effect of age and cholestyramine feeding on rat liver 3-hydroxy-3-methyl glutaryl CoA reductase, sterol carrier protein 1 and sterol carrier protein 2 activities. Lipids. 1982 Jul;17(7):507-10. [PubMed:7121212  ] 
  Enzyme Details
4. 7-dehydrocholesterol reductase
General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).

Gene Name:
DHCR7
Uniprot ID:
Q9UBM7  
Molecular weight:
54488.98
Reactions
Cholesterol + NADP → 7-Dehydrocholesterol + NADPHdetails
Cholesterol + NAD → 7-Dehydrocholesterol + NADH + Hydrogen Iondetails
Cholesterol + NADP → 7-Dehydrocholesterol + NADPH + Hydrogen Iondetails
References
  1. Porter FD: Smith-Lemli-Opitz syndrome: pathogenesis, diagnosis and management. Eur J Hum Genet. 2008 May;16(5):535-41. doi: 10.1038/ejhg.2008.10. Epub 2008 Feb  20. [PubMed:18285838  ] 
  Enzyme Details
5. Cholesterol side-chain cleavage enzyme, mitochondrial
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.

Gene Name:
CYP11A1
Uniprot ID:
P05108  
Molecular weight:
60101.87
References
  1. Guryev O, Carvalho RA, Usanov S, Gilep A, Estabrook RW: A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1). Proc Natl Acad Sci U S A. 2003 Dec 9;100(25):14754-9. Epub 2003 Dec 1. [PubMed:14657394  ] 
  Enzyme Details
6. Delta(24)-sterol reductase
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.

Gene Name:
DHCR24
Uniprot ID:
Q15392  
Molecular weight:
60100.805
Reactions
7-Dehydrodesmosterol + NADPH + Hydrogen Ion → 7-Dehydrocholesterol + NADPdetails