MiMeDB: Showing metabocard for zymosterol intermediate 1c (MMDBc0033050)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:32:33 UTC

Update Date

2022-08-31 22:21:13 UTC

Metabolite ID

MMDBc0033050

Metabolite Identification

Common Name

zymosterol intermediate 1c

Description

Zymosterol is an intermediate in the biosynthesis of both ergosterol, a major constituent of the fungal plasma membrane, and cholesterol, the homologous component in mammalian membranes. Cholesterol and ergosterol share most of their biosythetic pathway, with differences only in the part of the pathway that is downstream of zymosterol. [Biocyc PWY-6074 and PWY-6075]

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241222272D          

 34 37  0  0  0  0            999 V2000
    7.2519   -4.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5293   -5.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5293   -6.1461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2519   -6.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9512   -6.1461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6661   -6.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3965   -6.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3965   -5.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6661   -4.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9512   -5.3070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6661   -4.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3965   -3.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0958   -4.1026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0958   -4.9107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8805   -5.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3468   -4.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8805   -3.8462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0958   -3.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9512   -4.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0958   -5.7421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6032   -3.4421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9491   -6.9248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965   -6.5766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3095   -2.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0240   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7384   -2.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7384   -3.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4529   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5950   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8805   -2.9992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1661   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2519   -7.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -7.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9664   -7.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0  0  0  0
 17 13  1  0  0  0  0
 12 13  1  0  0  0  0
 13 18  1  1  0  0  0
  8 14  1  0  0  0  0
 15 14  1  0  0  0  0
 14 20  1  6  0  0  0
 11  9  1  0  0  0  0
 10  9  1  0  0  0  0
  8  9  2  0  0  0  0
  7  8  1  0  0  0  0
  5 10  1  0  0  0  0
 10 19  1  1  0  0  0
  1 10  1  0  0  0  0
 16 17  1  0  0  0  0
 30 17  1  0  0  0  0
 17 21  1  6  0  0  0
 11 12  1  0  0  0  0
 16 15  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  5 22  1  6  0  0  0
  3 23  1  1  0  0  0
 29 24  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 26  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

Structure #1
  Mrv0541 02241222272D          

 34 37  0  0  0  0            999 V2000
    7.2519   -4.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5293   -5.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5293   -6.1461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2519   -6.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9512   -6.1461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6661   -6.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3965   -6.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3965   -5.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6661   -4.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9512   -5.3070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6661   -4.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3965   -3.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0958   -4.1026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0958   -4.9107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8805   -5.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3468   -4.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8805   -3.8462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0958   -3.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9512   -4.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0958   -5.7421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6032   -3.4421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9491   -6.9248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965   -6.5766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3095   -2.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0240   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7384   -2.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7384   -3.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4529   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5950   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8805   -2.9992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1661   -2.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2519   -7.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -7.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9664   -7.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0  0  0  0
 17 13  1  0  0  0  0
 12 13  1  0  0  0  0
 13 18  1  1  0  0  0
  8 14  1  0  0  0  0
 15 14  1  0  0  0  0
 14 20  1  6  0  0  0
 11  9  1  0  0  0  0
 10  9  1  0  0  0  0
  8  9  2  0  0  0  0
  7  8  1  0  0  0  0
  5 10  1  0  0  0  0
 10 19  1  1  0  0  0
  1 10  1  0  0  0  0
 16 17  1  0  0  0  0
 30 17  1  0  0  0  0
 17 21  1  6  0  0  0
 11 12  1  0  0  0  0
 16 15  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  5 22  1  6  0  0  0
  3 23  1  1  0  0  0
 29 24  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 26  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033050

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C(C)=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O2/c1-18(2)8-7-9-19(3)22-12-13-23-21-10-11-25-27(20(4)30)26(31)15-17-29(25,6)24(21)14-16-28(22,23)5/h8,19,22-23,25-27,31H,7,9-17H2,1-6H3/t19-,22-,23+,25+,26+,27?,28-,29-/m1/s1

> <INCHI_KEY>
GGLAWNOISZYLHT-FICDAWEZSA-N

> <FORMULA>
C29H46O2

> <MOLECULAR_WEIGHT>
426.6743

> <EXACT_MASS>
426.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
53.56653363100979

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2S,5S,7S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-6-yl]ethan-1-one

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
6.371929220666667

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.548715995244436

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.766691276018094

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9006951766169298

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
130.83689999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zymosterol intermediate 1c

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      13.537  -9.167   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.188  -9.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.188 -11.473   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.537 -12.241   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.842 -11.473   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.177 -12.241   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.540 -11.473   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.540  -9.906   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.177  -9.167   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.842  -9.906   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.177  -7.658   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.540  -6.875   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.845  -7.658   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.845  -9.167   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.310  -9.645   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.181  -8.427   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.310  -7.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.845  -6.077   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.842  -8.398   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      18.845 -10.719   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      21.659  -6.425   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      14.838 -12.926   0.000  0.00  0.00           H+0
HETATM   23  O   UNK     0      10.820 -12.276   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      22.978  -5.599   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.311  -4.829   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      25.645  -5.599   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.645  -7.139   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.979  -4.829   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.644  -4.829   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.310  -5.599   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.977  -4.829   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.537 -13.781   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.203 -14.551   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.871 -14.551   0.000  0.00  0.00           C+0
CONECT    1   10    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2   23                                                  
CONECT    4    5    3   32                                                  
CONECT    5   10    4    6   22                                             
CONECT    6    7    5                                                       
CONECT    7    8    6                                                       
CONECT    8   14    9    7                                                  
CONECT    9   11   10    8                                                  
CONECT   10    9    5   19    1                                             
CONECT   11    9   12                                                       
CONECT   12   13   11                                                       
CONECT   13   14   17   12   18                                             
CONECT   14   13    8   15   20                                             
CONECT   15   14   16                                                       
CONECT   16   17   15                                                       
CONECT   17   13   16   30   21                                             
CONECT   18   13                                                            
CONECT   19   10                                                            
CONECT   20   14                                                            
CONECT   21   17                                                            
CONECT   22    5                                                            
CONECT   23    3                                                            
CONECT   24   29   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30                                                       
CONECT   30   17   29   31                                                  
CONECT   31   30                                                            
CONECT   32    4   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

Synonyms

Value	Source
Zymosterol intermediic acid 1C	Generator

Molecular Formula

C₂₉H₄₆O₂

Average Mass

426.6743

Monoisotopic Mass

426.349780716

IUPAC Name

1-[(2S,5S,7S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-6-yl]ethan-1-one

Traditional Name

zymosterol intermediate 1c

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C(C)=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

InChI Identifier

InChI=1S/C29H46O2/c1-18(2)8-7-9-19(3)22-12-13-23-21-10-11-25-27(20(4)30)26(31)15-17-29(25,6)24(21)14-16-28(22,23)5/h8,19,22-23,25-27,31H,7,9-17H2,1-6H3/t19-,22-,23+,25+,26+,27?,28-,29-/m1/s1

InChI Key

GGLAWNOISZYLHT-FICDAWEZSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0003900000-c8633ce99b3bd2ab4e4c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ar0-2139500000-2495705d9c6b28c661ab	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0hg9-3129100000-aa1b66ad19cbc07b9875	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-8d6e236c0015809927c0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0002900000-290ba0316ce1561ed4f5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-1009300000-68c0c7e47f186c76e998	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for zymosterol intermediate 1c (MMDBc0033050)

MOL for #<Metabolite:0x00007fd5d9193000>

3D MOL for #<Metabolite:0x00007fd5d9193000>

3D SDF for #<Metabolite:0x00007fd5d9193000>

3D-SDF for #<Metabolite:0x00007fd5d9193000>

PDB for #<Metabolite:0x00007fd5d9193000>

3D PDB for #<Metabolite:0x00007fd5d9193000>

SMILES for #<Metabolite:0x00007fd5d9193000>

INCHI for #<Metabolite:0x00007fd5d9193000>

Structure for #<Metabolite:0x00007fd5d9193000>

3D Structure for #<Metabolite:0x00007fd5d9193000>