NP-MRD: Showing NP-Card for 5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0221116)

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Record Information

Version

2.0

Created at

2022-09-05 22:36:20 UTC

Updated at

2022-09-05 22:36:20 UTC

NP-MRD ID

NP0221116

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Description

Sodagnitin D belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid is found in Cortinarius sodagnitus. Based on a literature review very few articles have been published on Sodagnitin D.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200362D          

 47 51  0  0  1  0            999 V2000
    5.9734   -2.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1196   -2.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8959   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1262   -1.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9508   -1.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4147   -0.3915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2301   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9730   -1.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6647   -2.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5782   -2.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896   -1.6384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7133   -1.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0833   -1.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3038   -0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4930   -1.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4416   -0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    1.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    2.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386    2.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    3.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    1.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0632    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4978    3.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3224    3.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1078    3.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9291    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0058   -0.2939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1521    0.5181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6358   -0.8265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  3 10  1  0  0  0  0
 11  2  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 30 42  1  0  0  0  0
 42 43  1  0  0  0  0
 24 43  1  0  0  0  0
 19 43  1  0  0  0  0
 43 44  1  1  0  0  0
 14 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 11 47  1  0  0  0  0
M  END


  Mrv1652309062200362D          

 47 51  0  0  1  0            999 V2000
    5.9734   -2.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1196   -2.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8959   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1262   -1.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9508   -1.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4147   -0.3915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2301   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9730   -1.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6647   -2.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5782   -2.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896   -1.6384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7133   -1.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0833   -1.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3038   -0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4930   -1.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4416   -0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    1.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    2.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386    2.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    3.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    1.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0632    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4978    3.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3224    3.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1078    3.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9291    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0058   -0.2939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1521    0.5181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6358   -0.8265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  3 10  1  0  0  0  0
 11  2  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 30 42  1  0  0  0  0
 42 43  1  0  0  0  0
 24 43  1  0  0  0  0
 19 43  1  0  0  0  0
 43 44  1  1  0  0  0
 14 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 11 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)(CC(O)=O)CC(=O)O[C@@H]1C[C@]2(C)[C@H]3CC(=O)[C@@H](C4=CC[C@H](O[C@H]4O)C(=C)C4=CC(=O)C(C)(C)O4)[C@]3(C)CC[C@H]2C(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C36H48O11/c1-18(22-14-26(38)33(4,5)47-22)21-10-9-19(31(43)46-21)29-20(37)13-25-35(29,7)12-11-24-32(2,3)30(42)23(15-36(24,25)8)45-28(41)17-34(6,44)16-27(39)40/h9,14,21,23-25,29,31,43-44H,1,10-13,15-17H2,2-8H3,(H,39,40)/t21-,23+,24-,25-,29+,31+,34?,35+,36-/m0/s1

> <INCHI_KEY>
RDIRGIFRWPIZQB-WIVJLBMXSA-N

> <FORMULA>
C36H48O11

> <MOLECULAR_WEIGHT>
656.769

> <EXACT_MASS>
656.319662366

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
70.31472415470105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[(3R,3aR,5aR,8R,9aR,9bR)-3-[(2R,6S)-6-[1-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2H-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-dodecahydro-1H-cyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_LOGP>
3.5212900269999983

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.813170582542872

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.678240744434205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.008406580965593

> <JCHEM_POLAR_SURFACE_AREA>
173.73

> <JCHEM_REFRACTIVITY>
170.36280000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-{[(3R,3aR,5aR,8R,9aR,9bR)-3-[(2R,6S)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2H-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      11.150  -5.568   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.423  -4.053   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.872  -3.531   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.302  -2.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.842  -2.004   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      15.707  -0.731   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      15.363  -3.453   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.750  -2.783   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.174  -4.762   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.146  -4.397   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.247  -3.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.798  -3.580   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.622  -2.586   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.895  -1.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.719  -0.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.141   2.271   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.167  -1.660   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.920  -2.095   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.824  -1.159   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.745   0.674   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.828   3.340   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.556   1.983   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.639   4.649   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.179   4.601   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.227   6.140   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.131   3.062   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.718   4.553   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -6.529   5.862   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -8.068   5.814   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.801   7.219   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.601   2.175   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.344  -0.549   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       9.617   0.967   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      10.520  -1.543   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    3                                                       
CONECT   11    2   12   47                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   45                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   43                                                  
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   43                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   42                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   30   43                                                       
CONECT   43   42   24   19   44                                             
CONECT   44   43                                                            
CONECT   45   14   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   11                                                       
MASTER        0    0    0    0    0    0    0    0   47    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₄₈O₁₁

Average Mass

656.7690 Da

Monoisotopic Mass

656.31966 Da

IUPAC Name

5-{[(3R,3aR,5aR,8R,9aR,9bR)-3-[(2R,6S)-6-[1-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2H-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-dodecahydro-1H-cyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Traditional Name

5-{[(3R,3aR,5aR,8R,9aR,9bR)-3-[(2R,6S)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2H-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

CC(O)(CC(O)=O)CC(=O)O[C@@H]1C[C@]2(C)[C@H]3CC(=O)[C@@H](C4=CC[C@H](O[C@H]4O)C(=C)C4=CC(=O)C(C)(C)O4)[C@]3(C)CC[C@H]2C(C)(C)C1=O

InChI Identifier

InChI=1S/C36H48O11/c1-18(22-14-26(38)33(4,5)47-22)21-10-9-19(31(43)46-21)29-20(37)13-25-35(29,7)12-11-24-32(2,3)30(42)23(15-36(24,25)8)45-28(41)17-34(6,44)16-27(39)40/h9,14,21,23-25,29,31,43-44H,1,10-13,15-17H2,2-8H3,(H,39,40)/t21-,23+,24-,25-,29+,31+,34?,35+,36-/m0/s1

InChI Key

RDIRGIFRWPIZQB-WIVJLBMXSA-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
Calonarius sodagnitus	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
Branched fatty acid
Fatty acid ester
Heterocyclic fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Methyl-branched fatty acid
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
3-furanone
Pyran
Fatty acyl
Vinylogous ester
Tertiary alcohol
Dihydrofuran
Cyclic ketone
Ketone
Carboxylic acid ester
Hemiacetal
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Organooxygen compound
Carbonyl group
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.52	ChemAxon
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	173.73 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	170.36 m³·mol⁻¹	ChemAxon
Polarizability	70.31 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

8683916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10508515

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0221116)

MOL for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D MOL for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D SDF for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D-SDF for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

PDB for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D PDB for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

SMILES for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

INCHI for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

Structure for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D Structure for NP0221116 (5-{[(3r,3ar,5ar,8r,9ar,9br)-3-[(2r,6s)-6-[1-(5,5-dimethyl-4-oxofuran-2-yl)ethenyl]-2-hydroxy-5,6-dihydro-2h-pyran-3-yl]-3a,6,6,9a-tetramethyl-2,7-dioxo-octahydrocyclopenta[a]naphthalen-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)