NP-MRD: Showing NP-Card for 5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0291487)

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Record Information

Version

2.0

Created at

2022-09-09 22:36:10 UTC

Updated at

2022-09-09 22:36:10 UTC

NP-MRD ID

NP0291487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Description

Fasciculic acid A, also known as fasciculate a, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Fasciculic acid A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, fasciculic acid a has been detected, but not quantified in, mushrooms. 5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid is found in Hypholoma fasciculare. This could make fasciculic acid a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309082D          

 44 47  0  0  0  0            999 V2000
   -2.6962    0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    4.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6467    1.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    1.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361    1.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8244    1.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7301    2.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 44 25  1  0  0  0  0
 44 29  1  0  0  0  0
M  END

     RDKit          3D

104107  0  0  0  0  0  0  0  0999 V2000
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  8 57  1  0
  9 58  1  0
  9 59  1  0
  9 60  1  0
 10 61  1  0
 11 62  1  6
 12 63  1  0
 12 64  1  0
 13 65  1  0
 13 66  1  0
 15 67  1  0
 15 68  1  0
 15 69  1  0
 18 70  1  0
 18 71  1  0
 19 72  1  0
 19 73  1  0
 21 74  1  0
 21 75  1  0
 21 76  1  0
 23 77  1  0
 23 78  1  0
 23 79  1  0
 24 80  1  0
 24 81  1  0
 25 82  1  1
 29 83  1  0
 29 84  1  0
 31 85  1  0
 31 86  1  0
 31 87  1  0
 32 88  1  0
 33 89  1  0
 33 90  1  0
 36 91  1  0
 37 92  1  1
 38 93  1  0
 40 94  1  0
 40 95  1  0
 40 96  1  0
 41 97  1  0
 41 98  1  0
 41 99  1  0
 42100  1  6
 43101  1  0
 43102  1  0
 44103  1  0
 44104  1  0
M  END


  Mrv0541 05061309082D          

 44 47  0  0  0  0            999 V2000
   -2.6962    0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    4.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660    3.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1607   -0.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0030   -0.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6467    1.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    1.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361    1.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1983    3.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8244    1.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035    3.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086    4.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307    1.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301    2.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323    1.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473    3.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444    1.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920    1.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6041    1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9798    1.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071    1.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    2.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    2.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838    3.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041    2.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404    3.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1480    1.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1359    0.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    2.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    3.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7920    1.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601    2.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762    2.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959    2.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4589    1.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9480    0.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8556   -0.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283    2.4202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965    3.0509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057    0.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9372    0.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359    1.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 21  1  1  0  0  0  0
 21 10  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23 15  1  0  0  0  0
 24 11  1  0  0  0  0
 24 23  2  0  0  0  0
 25 18  1  0  0  0  0
 26 12  1  0  0  0  0
 27 13  1  0  0  0  0
 28 19  1  0  0  0  0
 29 20  1  0  0  0  0
 30 25  1  0  0  0  0
 31  2  1  0  0  0  0
 31  3  1  0  0  0  0
 31 26  1  0  0  0  0
 31 30  1  0  0  0  0
 32  4  1  0  0  0  0
 32  5  1  0  0  0  0
 32 27  1  0  0  0  0
 33  6  1  0  0  0  0
 33 19  1  0  0  0  0
 33 20  1  0  0  0  0
 34  7  1  0  0  0  0
 34 18  1  0  0  0  0
 34 23  1  0  0  0  0
 34 26  1  0  0  0  0
 35  8  1  0  0  0  0
 35 17  1  0  0  0  0
 35 22  1  0  0  0  0
 36  9  1  0  0  0  0
 36 16  1  0  0  0  0
 36 24  1  0  0  0  0
 36 35  1  0  0  0  0
 37 27  1  0  0  0  0
 38 28  2  0  0  0  0
 39 28  1  0  0  0  0
 40 29  2  0  0  0  0
 41 30  1  0  0  0  0
 42 32  1  0  0  0  0
 43 33  1  0  0  0  0
 44 25  1  0  0  0  0
 44 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(O)C(C)(C)O)C1CCC2(C)C3=C(CCC12C)C1(C)CC(OC(=O)CC(C)(O)CC(O)=O)C(O)C(C)(C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C36H60O8/c1-21(10-13-27(37)32(4,5)42)22-14-16-36(9)24-11-12-26-31(2,3)30(41)25(44-29(40)20-33(6,43)19-28(38)39)18-34(26,7)23(24)15-17-35(22,36)8/h21-22,25-27,30,37,41-43H,10-20H2,1-9H3,(H,38,39)

> <INCHI_KEY>
VOAJMYUEWCGJID-UHFFFAOYSA-N

> <FORMULA>
C36H60O8

> <MOLECULAR_WEIGHT>
620.8568

> <EXACT_MASS>
620.428818896

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
72.14697845480988

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[14-(5,6-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-4-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
4.407559986999998

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.468518433123705

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.799039540037931

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0083989003163154

> <JCHEM_POLAR_SURFACE_AREA>
144.51999999999998

> <JCHEM_REFRACTIVITY>
168.89930000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[14-(5,6-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-4-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -5.033   1.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.928   8.047   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.790   7.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.500  -0.323   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.339  -0.053   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.674   3.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.896   3.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.801   2.683   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.237   7.012   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.139   3.113   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.567   7.236   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.949   7.508   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.084   1.898   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.096   5.598   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.620   3.162   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.822   6.462   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.136   2.891   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.412   3.704   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.461   2.434   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.429   1.892   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.613   2.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.668   4.119   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.097   4.611   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.090   5.788   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.928   3.975   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.942   6.330   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.610   2.108   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.454   1.257   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.436   3.069   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.451   5.424   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.458   6.601   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.555   0.892   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.945   2.163   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.419   4.882   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.129   4.069   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.606   5.517   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -10.190   3.535   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      12.970   1.528   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.930  -0.192   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       6.959   4.518   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.967   5.695   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -11.771   1.838   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       9.216   0.647   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       4.920   2.798   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   31                                                            
CONECT    3   31                                                            
CONECT    4   32                                                            
CONECT    5   32                                                            
CONECT    6   33                                                            
CONECT    7   34                                                            
CONECT    8   35                                                            
CONECT    9   36                                                            
CONECT   10   13   21                                                       
CONECT   11   12   24                                                       
CONECT   12   11   26                                                       
CONECT   13   10   27                                                       
CONECT   14   16   22                                                       
CONECT   15   17   23                                                       
CONECT   16   14   36                                                       
CONECT   17   15   35                                                       
CONECT   18   25   34                                                       
CONECT   19   28   33                                                       
CONECT   20   29   33                                                       
CONECT   21    1   10   22                                                  
CONECT   22   14   21   35                                                  
CONECT   23   15   24   34                                                  
CONECT   24   11   23   36                                                  
CONECT   25   18   30   44                                                  
CONECT   26   12   31   34                                                  
CONECT   27   13   32   37                                                  
CONECT   28   19   38   39                                                  
CONECT   29   20   40   44                                                  
CONECT   30   25   31   41                                                  
CONECT   31    2    3   26   30                                             
CONECT   32    4    5   27   42                                             
CONECT   33    6   19   20   43                                             
CONECT   34    7   18   23   26                                             
CONECT   35    8   17   22   36                                             
CONECT   36    9   16   24   35                                             
CONECT   37   27                                                            
CONECT   38   28                                                            
CONECT   39   28                                                            
CONECT   40   29                                                            
CONECT   41   30                                                            
CONECT   42   32                                                            
CONECT   43   33                                                            
CONECT   44   25   29                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Value	Source
Fasciculate a	Generator
(+)-Fasciculic acid a	HMDB
2-O-(3-Hydroxy-3-methylglutaryl)fasciculol a	HMDB
5-{[14-(5,6-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-4-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoate	Generator
Fasciculic acid a	MeSH

Chemical Formula

C₃₆H₆₀O₈

Average Mass

620.8568 Da

Monoisotopic Mass

620.42882 Da

IUPAC Name

5-{[14-(5,6-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-4-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Traditional Name

5-{[14-(5,6-dihydroxy-6-methylheptan-2-yl)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-4-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(O)C(C)(C)O)C1CCC2(C)C3=C(CCC12C)C1(C)CC(OC(=O)CC(C)(O)CC(O)=O)C(O)C(C)(C)C1CC3

InChI Identifier

InChI=1S/C36H60O8/c1-21(10-13-27(37)32(4,5)42)22-14-16-36(9)24-11-12-26-31(2,3)30(41)25(44-29(40)20-33(6,43)19-28(38)39)18-34(26,7)23(24)15-17-35(22,36)8/h21-22,25-27,30,37,41-43H,10-20H2,1-9H3,(H,38,39)

InChI Key

VOAJMYUEWCGJID-UHFFFAOYSA-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
Hypholoma fasciculare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Trihydroxy bile acid, alcohol, or derivatives
25-hydroxysteroid
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
3-hydroxysteroid
Hydroxysteroid
Steroid
Dicarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen 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	4.88	ALOGPS
logP	4.41	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	168.9 m³·mol⁻¹	ChemAxon
Polarizability	72.15 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

HMDB0036439

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015326

KNApSAcK ID

C00034509

Chemspider ID

22943356

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14506480

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0291487)

MOL for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D MOL for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D SDF for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D-SDF for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

PDB for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D PDB for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

SMILES for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

INCHI for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

Structure for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D Structure for NP0291487 (5-{[1-(5,6-dihydroxy-6-methylheptan-2-yl)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)