NP-MRD: Showing NP-Card for dehydroergosterol (NP0173152)

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Record Information

Version

1.0

Created at

2022-09-03 10:14:35 UTC

Updated at

2022-09-03 10:14:36 UTC

NP-MRD ID

NP0173152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dehydroergosterol

Description

Dehydroergosterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, dehydroergosterol is considered to be a sterol lipid molecule. dehydroergosterol is found in Axinella cannabina, Chlorella vulgaris, Conium maculatum, Eutypa lata and Leptosphaeria maculans. It was first documented in 2007 (PMID: 17439666). Dehydroergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 19010302) (PMID: 19019985) (PMID: 19450500) (PMID: 19477318) (PMID: 20070610) (PMID: 20798830).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 06081214522D          

 29 32  0  0  1  0            999 V2000
   -3.0532   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411   -0.9702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7092   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1953   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4756    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195   -0.2441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5392   -1.0201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1906   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -0.2709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1505    0.3804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8396    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459    1.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    2.5601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2178    2.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    3.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305    3.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586    3.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9677    0.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1794    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3365    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 16 24  1  1  0  0  0
 11 25  1  1  0  0  0
  8 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
M  END

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
    6.8931   -0.5647    1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0045    0.0729   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1193   -0.9455   -1.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1624   -0.0248   -0.3196 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0960   -0.7138    0.4808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4756    1.0806    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3087    0.6813    1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4029   -0.3411    0.5790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6495   -1.6378    1.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    0.0575    0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3374    0.0390    1.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8985    0.3953    1.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640    0.0673    0.6785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3526   -1.3684    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2821    0.1050    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4553   -1.5984    1.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8922   -0.6797    1.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2999   -0.4218   -2.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9565   -1.6622   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7427    0.8436   -2.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0496    2.3131   -1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8596    2.1114   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527   -0.6840   -0.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5046   -1.6357    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.2926    2.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2600   -1.7036    2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207    1.4459    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    0.7299   -1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053    2.2777   -0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -0.2186   -1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1609    1.5345   -2.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    2.0092    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1447    0.6133   -2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900   -0.2542   -2.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4664   -0.9905   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3200   -1.9948   -0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8089    0.4746   -1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3966   -0.0937    1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2404    1.5277    1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2278    1.9356   -0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7113    1.6196    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
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 19 20  1  0
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 22 23  1  0
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 25 26  2  0
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 27 28  1  0
 28 29  1  6
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 28 13  1  0
 25 14  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
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  3 35  1  0
  3 36  1  0
  4 37  1  1
  5 38  1  0
  5 39  1  0
  5 40  1  0
  6 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  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
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 27 67  1  0
 27 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
M  END


  Mrv0541 06081214522D          

 29 32  0  0  1  0            999 V2000
   -3.0532   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411   -0.9702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7092   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6441   -0.2709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1505    0.3804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8396    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459    1.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    2.5601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2178    2.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    3.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305    3.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586    3.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9677    0.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1794    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3365    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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  7 12  1  0  0  0  0
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 16 24  1  1  0  0  0
 11 25  1  1  0  0  0
  8 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173152

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,14,18-20,22,24-25,29H,11-13,15-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1

> <INCHI_KEY>
QSVJYFLQYMVBDR-CMNOFMQQSA-N

> <FORMULA>
C28H42O

> <MOLECULAR_WEIGHT>
394.6325

> <EXACT_MASS>
394.323565966

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
50.567393609690214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),7,9-trien-5-ol

> <ALOGPS_LOGP>
7.50

> <JCHEM_LOGP>
6.226827507666666

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.337249578391205

> <JCHEM_PKA_STRONGEST_BASIC>
-1.339087034411687

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
127.98169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.81e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),7,9-trien-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-JUN-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-12         0                                  
HETATM    1  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.301   2.137   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.246   3.352   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.665   4.779   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.140   4.989   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.611   5.995   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.030   7.421   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.136   5.784   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.406   0.499   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15   25                                             
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16                                                            
CONECT   25   11                                                            
CONECT   26    8    4   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    2                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(3beta,22E)-Ergosta-5,7,9(11),22-tetraen-3-ol	ChEBI
delta(5,7,9(11)22)-Ergostatetraen-3-ol	ChEBI
Ergosta-5,7,9(11),22-tetraen-3beta-ol	ChEBI
(3b,22E)-Ergosta-5,7,9(11),22-tetraen-3-ol	Generator
(3Β,22E)-ergosta-5,7,9(11),22-tetraen-3-ol	Generator
Δ(5,7,9(11)22)-ergostatetraen-3-ol	Generator
Ergosta-5,7,9(11),22-tetraen-3b-ol	Generator
Ergosta-5,7,9(11),22-tetraen-3β-ol	Generator
Ergosta-5,7,9(11),22-tetraen-3 beta-ol	MeSH

Chemical Formula

C₂₈H₄₂O

Average Mass

394.6325 Da

Monoisotopic Mass

394.32357 Da

IUPAC Name

(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),7,9-trien-5-ol

Traditional Name

(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),7,9-trien-5-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3=CC[C@]12C

InChI Identifier

InChI=1S/C28H42O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,14,18-20,22,24-25,29H,11-13,15-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1

InChI Key

QSVJYFLQYMVBDR-CMNOFMQQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Axinella cannabina	LOTUS Database	35616633
Chlorella vulgaris	LOTUS Database	35616633
Conium maculatum	LOTUS Database	35616633
Eutypa lata	LOTUS Database	35616633
Leptosphaeria maculans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
3-hydroxy-delta-5-steroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-7-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:64762 )
ergostanoid (CHEBI:64762 )
phytosterols (CHEBI:64762 )
Ergosterols and C24-methyl derivatives (LMST01031023 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.5	ALOGPS
logP	6.23	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	18.34	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.98 m³·mol⁻¹	ChemAxon
Polarizability	50.57 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6436660

PDB ID

Not Available

ChEBI ID

64762

Good Scents ID

Not Available

References

General References

Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]
Chong PL, Zhu W, Venegas B: On the lateral structure of model membranes containing cholesterol. Biochim Biophys Acta. 2009 Jan;1788(1):2-11. doi: 10.1016/j.bbamem.2008.10.010. Epub 2008 Oct 29. [PubMed:19010302 ]
Mondal M, Mesmin B, Mukherjee S, Maxfield FR: Sterols are mainly in the cytoplasmic leaflet of the plasma membrane and the endocytic recycling compartment in CHO cells. Mol Biol Cell. 2009 Jan;20(2):581-8. doi: 10.1091/mbc.e08-07-0785. Epub 2008 Nov 19. [PubMed:19019985 ]
Qiu L, Lewis A, Como J, Vaughn MW, Huang J, Somerharju P, Virtanen J, Cheng KH: Cholesterol modulates the interaction of beta-amyloid peptide with lipid bilayers. Biophys J. 2009 May 20;96(10):4299-307. doi: 10.1016/j.bpj.2009.02.036. [PubMed:19450500 ]
Garvik O, Benediktson P, Simonsen AC, Ipsen JH, Wustner D: The fluorescent cholesterol analog dehydroergosterol induces liquid-ordered domains in model membranes. Chem Phys Lipids. 2009 Jun;159(2):114-8. doi: 10.1016/j.chemphyslip.2009.03.002. Epub 2009 Mar 28. [PubMed:19477318 ]
Wustner D, Landt Larsen A, Faergeman NJ, Brewer JR, Sage D: Selective visualization of fluorescent sterols in Caenorhabditis elegans by bleach-rate-based image segmentation. Traffic. 2010 Apr;11(4):440-54. doi: 10.1111/j.1600-0854.2010.01040.x. Epub 2010 Jan 12. [PubMed:20070610 ]
Wustner D, Sage D: Multicolor bleach-rate imaging enlightens in vivo sterol transport. Commun Integr Biol. 2010 Jul;3(4):370-3. doi: 10.4161/cib.3.4.11972. [PubMed:20798830 ]
Kohut P, Wustner D, Hronska L, Kuchler K, Hapala I, Valachovic M: The role of ABC proteins Aus1p and Pdr11p in the uptake of external sterols in yeast: dehydroergosterol fluorescence study. Biochem Biophys Res Commun. 2011 Jan 7;404(1):233-8. doi: 10.1016/j.bbrc.2010.11.099. Epub 2010 Nov 24. [PubMed:21110944 ]
Wustner D, Brewer JR, Bagatolli L, Sage D: Potential of ultraviolet wide-field imaging and multiphoton microscopy for analysis of dehydroergosterol in cellular membranes. Microsc Res Tech. 2011 Jan;74(1):92-108. doi: 10.1002/jemt.20878. [PubMed:21181715 ]
Wustner D, Solanko L, Sokol E, Garvik O, Li Z, Bittman R, Korte T, Herrmann A: Quantitative assessment of sterol traffic in living cells by dual labeling with dehydroergosterol and BODIPY-cholesterol. Chem Phys Lipids. 2011 Mar;164(3):221-35. doi: 10.1016/j.chemphyslip.2011.01.004. Epub 2011 Feb 1. [PubMed:21291873 ]
LOTUS database [Link]

Showing NP-Card for dehydroergosterol (NP0173152)

MOL for NP0173152 (dehydroergosterol)

3D MOL for NP0173152 (dehydroergosterol)

3D SDF for NP0173152 (dehydroergosterol)

3D-SDF for NP0173152 (dehydroergosterol)

PDB for NP0173152 (dehydroergosterol)

3D PDB for NP0173152 (dehydroergosterol)

SMILES for NP0173152 (dehydroergosterol)

INCHI for NP0173152 (dehydroergosterol)

Structure for NP0173152 (dehydroergosterol)

3D Structure for NP0173152 (dehydroergosterol)