NP-MRD: Showing NP-Card for (2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate (NP0179243)

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Record Information

Version

2.0

Created at

2022-09-03 17:23:58 UTC

Updated at

2022-09-03 17:23:58 UTC

NP-MRD ID

NP0179243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate

Description

(2S,3R,4S)-4-hydroxy-2-[(2S,5S,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]-5-(propan-2-yl)hept-5-en-3-yl acetate belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. (2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate is found in Pisolithus arhizus. Based on a literature review very few articles have been published on (2S,3R,4S)-4-hydroxy-2-[(2S,5S,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]-5-(propan-2-yl)hept-5-en-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032219232D          

 38 41  0  0  1  0            999 V2000
    2.7267   -3.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -2.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548   -2.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -2.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503   -3.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1657   -1.6699    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6594   -1.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -2.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -2.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 14  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 16 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  6  0  0  0
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 27 28  1  6  0  0  0
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 33 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 21 38  1  0  0  0  0
M  END

     RDKit          3D

 94 97  0  0  0  0  0  0  0  0999 V2000
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 38 94  1  0
M  END


  Mrv1652309032219232D          

 38 41  0  0  1  0            999 V2000
    2.7267   -3.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -2.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3612   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -2.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503   -3.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1657   -1.6699    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6594   -1.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -2.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -2.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 14  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  6  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 21 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179243

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C34H56O4/c1-11-23(20(2)3)29(37)30(38-22(5)35)21(4)24-14-18-34(10)26-12-13-27-31(6,7)28(36)16-17-32(27,8)25(26)15-19-33(24,34)9/h11,20-21,24,27-30,36-37H,12-19H2,1-10H3/b23-11+/t21-,24+,27-,28-,29-,30+,32+,33+,34-/m0/s1

> <INCHI_KEY>
SXYWLRGQHFDETK-FPHFNQAOSA-N

> <FORMULA>
C34H56O4

> <MOLECULAR_WEIGHT>
528.818

> <EXACT_MASS>
528.417860283

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
64.01915384463003

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5E)-4-hydroxy-2-[(2S,5S,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-5-(propan-2-yl)hept-5-en-3-yl acetate

> <JCHEM_LOGP>
6.6516247486666655

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.553786825962863

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.580706162832954

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8069733699856444

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
155.64580000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5E)-4-hydroxy-2-[(2S,5S,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-5-isopropylhept-5-en-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.090  -6.181   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.670  -4.754   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.196  -4.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.141  -5.759   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.666  -5.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.561  -7.186   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.776  -3.117   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.831  -1.901   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.247  -4.122   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.772  -3.912   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.717  -5.127   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   25                                             
CONECT   20   19                                                            
CONECT   21   19   22   38                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   16   19   26                                             
CONECT   26   25                                                            
CONECT   27   22   28   29   36                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   27   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   21                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S)-4-Hydroxy-2-[(2S,5S,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl]-5-(propan-2-yl)hept-5-en-3-yl acetic acid	Generator

Chemical Formula

C₃₄H₅₆O₄

Average Mass

528.8180 Da

Monoisotopic Mass

528.41786 Da

IUPAC Name

(2S,3R,4S,5E)-4-hydroxy-2-[(2S,5S,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-5-(propan-2-yl)hept-5-en-3-yl acetate

Traditional Name

(2S,3R,4S,5E)-4-hydroxy-2-[(2S,5S,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-5-isopropylhept-5-en-3-yl acetate

CAS Registry Number

Not Available

SMILES

C\C=C(/C(C)C)[C@H](O)[C@H](OC(C)=O)[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3

InChI Identifier

InChI=1S/C34H56O4/c1-11-23(20(2)3)29(37)30(38-22(5)35)21(4)24-14-18-34(10)26-12-13-27-31(6,7)28(36)16-17-32(27,8)25(26)15-19-33(24,34)9/h11,20-21,24,27-30,36-37H,12-19H2,1-10H3/b23-11+/t21-,24+,27-,28-,29-,30+,32+,33+,34-/m0/s1

InChI Key

SXYWLRGQHFDETK-FPHFNQAOSA-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
Pisolithus arhizus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
23-hydroxysteroid
Bile acid, alcohol, or derivatives
Steroid ester
3-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
3-beta-hydroxysteroid
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	6.65	ChemAxon
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	155.65 m³·mol⁻¹	ChemAxon
Polarizability	64.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162981574

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate (NP0179243)

MOL for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

3D MOL for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

3D SDF for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

3D-SDF for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

PDB for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

3D PDB for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

SMILES for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

INCHI for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

Structure for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)

3D Structure for NP0179243 ((2s,3r,4s,5e)-2-[(1r,3ar,5ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-5-isopropylhept-5-en-3-yl acetate)