NP-MRD: Showing NP-Card for 5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate (NP0007845)

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Record Information

Version

2.0

Created at

2020-12-09 05:25:11 UTC

Updated at

2021-07-15 16:58:42 UTC

NP-MRD ID

NP0007845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate

Provided By

NPAtlas

Description

5Alpha,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. 5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate is found in Conocybe siliginea. 5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate was first documented in 2008 (PMID: 18598081). Based on a literature review very few articles have been published on 5alpha,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106043D          

 57 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242106043D          

 57 59  0  0  0  0            999 V2000
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   -5.2872   -2.4722    0.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -2.2334   -1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5144   -3.6897   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913   -2.0500    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -4.0740    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912   -4.3244    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494   -4.0699    2.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900   -2.3658    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471   -1.4991    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637    0.7360   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5463    1.5095    2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666    2.3711    0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    3.2201    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407    3.0269    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -0.7307    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770    0.5201   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    1.4068    0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7360    3.3217   -0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9609    3.9937   -0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0023    3.7938   -2.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515    0.5444   -3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8728    1.6599   -3.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1734    2.2768   -3.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9401    2.2043   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    2.1814    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1706   -0.0163   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  9 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26  2  1  0  0  0  0
 19 14  1  0  0  0  0
 26 20  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  2 30  1  6  0  0  0
  3 31  1  6  0  0  0
  4 32  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  6 35  1  1  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  8 38  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 14 41  1  6  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 19 46  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 23 49  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 24 54  1  0  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 26 57  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0007845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])C(=C2C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[C@]2([H])[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])C1([H])[H])C([H])([H])OC(=O)[C@]1([H])N([H])C(=O)C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H31NO5/c1-11-13-7-20(2,3)8-14(13)15(12(9-22)6-17(11)23)10-26-19(25)16-4-5-18(24)21-16/h11-13,16-17,22-23H,4-10H2,1-3H3,(H,21,24)/t11-,12-,13+,16+,17+/m0/s1

> <INCHI_KEY>
IQKGQLSGOWFRNJ-IPJLKBMESA-N

> <FORMULA>
C20H31NO5

> <MOLECULAR_WEIGHT>
365.47

> <EXACT_MASS>
365.220223102

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.5533029900425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(5R,7R,8S,8aR)-7-hydroxy-5-(hydroxymethyl)-2,2,8-trimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-4-yl]methyl (2R)-5-oxopyrrolidine-2-carboxylate

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.4922883913333337

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.796983008063435

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.396258443176558

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2246540745561885

> <JCHEM_POLAR_SURFACE_AREA>
95.85999999999999

> <JCHEM_REFRACTIVITY>
97.17040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(5R,7R,8S,8aR)-7-hydroxy-5-(hydroxymethyl)-2,2,8-trimethyl-3,5,6,7,8,8a-hexahydro-1H-azulen-4-yl]methyl (2R)-5-oxopyrrolidine-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -3.6289    0.1104    1.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227   -0.3653   -0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5995   -1.8116   -0.4187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3516   -2.3266    0.6354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205   -2.6030   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -2.3206    0.7039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8609   -3.6171    1.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916   -3.5248    2.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512   -1.2416    0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377   -1.4100    0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7212   -0.4009    0.3409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585   -0.5025    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -1.5173    1.3100 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494    0.5159    0.3151 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7909    1.7945    1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258    2.5135    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179    1.4090    0.8086 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3523    1.6035    0.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824    0.1929    0.7725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002   -0.1445   -0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544    0.9017   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7744    1.9449   -1.4600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2344    3.3113   -1.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8225    1.5965   -2.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725    1.7419   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2031    0.2608   -0.8771 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6598    0.2698    1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1659   -0.6985    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2482    1.0335    1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    0.1122   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862   -2.0689   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2872   -2.4722    0.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -2.2334   -1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5144   -3.6897   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913   -2.0500    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -4.0740    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912   -4.3244    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494   -4.0699    2.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900   -2.3658    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471   -1.4991    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637    0.7360   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5463    1.5095    2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666    2.3711    0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    3.2201    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407    3.0269    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -0.7307    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770    0.5201   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    1.4068    0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7360    3.3217   -0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9609    3.9937   -0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0023    3.7938   -2.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515    0.5444   -3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8728    1.6599   -3.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1734    2.2768   -3.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9401    2.2043   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    2.1814    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1706   -0.0163   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  9 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26  2  1  0
 19 14  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  6
  3 31  1  6
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
  7 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  6
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  6
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.629   0.110   1.079  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.423  -0.365  -0.343  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.599  -1.812  -0.419  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.352  -2.327   0.635  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.321  -2.603  -0.560  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.526  -2.321   0.704  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.861  -3.617   1.079  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.092  -3.525   2.232  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.551  -1.242   0.336  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.838  -1.410   0.717  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.721  -0.401   0.341  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.059  -0.502   0.673  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.431  -1.517   1.310  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.049   0.516   0.315  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.791   1.795   1.113  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.126   2.514   1.042  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.118   1.409   0.809  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.352   1.603   0.679  0.00  0.00           O+0
HETATM   19  N   UNK     0       5.382   0.193   0.773  0.00  0.00           N+0
HETATM   20  C   UNK     0      -0.900  -0.145  -0.341  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.054   0.902  -0.696  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.774   1.945  -1.460  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.234   3.311  -1.240  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.823   1.597  -2.907  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.172   1.742  -0.840  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.203   0.261  -0.877  0.00  0.00           C+0
HETATM   27  H   UNK     0      -2.660   0.270   1.585  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.166  -0.699   1.649  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.248   1.034   1.117  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.284   0.112  -0.916  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.186  -2.069  -1.350  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.287  -2.472   0.395  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.783  -2.233  -1.465  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.514  -3.690  -0.673  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.191  -2.050   1.538  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.309  -4.074   0.230  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.691  -4.324   1.312  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.449  -4.070   2.987  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.290  -2.366   0.338  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.947  -1.499   1.852  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.064   0.736  -0.767  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.546   1.510   2.168  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.967   2.371   0.678  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.101   3.220   0.204  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.341   3.027   2.002  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.788  -0.731   1.040  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.777   0.520  -1.451  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.540   1.407   0.174  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.736   3.322  -0.693  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.961   3.994  -0.752  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.002   3.794  -2.233  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.452   0.544  -3.038  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.873   1.660  -3.304  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.173   2.277  -3.492  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.940   2.204  -1.481  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.217   2.181   0.175  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.171  -0.016  -1.979  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   26   30                                             
CONECT    3    2    4    5   31                                             
CONECT    4    3   32                                                       
CONECT    5    3    6   33   34                                             
CONECT    6    5    7    9   35                                             
CONECT    7    6    8   36   37                                             
CONECT    8    7   38                                                       
CONECT    9    6   10   20                                                  
CONECT   10    9   11   39   40                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19   41                                             
CONECT   15   14   16   42   43                                             
CONECT   16   15   17   44   45                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   14   46                                                  
CONECT   20    9   21   26                                                  
CONECT   21   20   22   47   48                                             
CONECT   22   21   23   24   25                                             
CONECT   23   22   49   50   51                                             
CONECT   24   22   52   53   54                                             
CONECT   25   22   26   55   56                                             
CONECT   26   25    2   20   57                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   19                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   23                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
   -3.6289    0.1104    1.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227   -0.3653   -0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5995   -1.8116   -0.4187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3516   -2.3266    0.6354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205   -2.6030   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -2.3206    0.7039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8609   -3.6171    1.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916   -3.5248    2.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512   -1.2416    0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377   -1.4100    0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7212   -0.4009    0.3409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585   -0.5025    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -1.5173    1.3100 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494    0.5159    0.3151 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7909    1.7945    1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258    2.5135    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179    1.4090    0.8086 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3523    1.6035    0.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824    0.1929    0.7725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002   -0.1445   -0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544    0.9017   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7744    1.9449   -1.4600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2344    3.3113   -1.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8225    1.5965   -2.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725    1.7419   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2031    0.2608   -0.8771 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6598    0.2698    1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1659   -0.6985    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2482    1.0335    1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    0.1122   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862   -2.0689   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2872   -2.4722    0.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -2.2334   -1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5144   -3.6897   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913   -2.0500    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -4.0740    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912   -4.3244    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494   -4.0699    2.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900   -2.3658    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471   -1.4991    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637    0.7360   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5463    1.5095    2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666    2.3711    0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    3.2201    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407    3.0269    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -0.7307    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770    0.5201   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    1.4068    0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7360    3.3217   -0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9609    3.9937   -0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0023    3.7938   -2.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515    0.5444   -3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8728    1.6599   -3.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1734    2.2768   -3.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9401    2.2043   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    2.1814    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1706   -0.0163   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  9 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26  2  1  0
 19 14  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  6
  3 31  1  6
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
  7 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  6
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5a,12-Dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate	Generator
5a,12-Dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamic acid	Generator
5alpha,12-Dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamic acid	Generator
5Α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate	Generator
5Α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamic acid	Generator
[(5R,7R,8S,8AR)-7-hydroxy-5-(hydroxymethyl)-2,2,8-trimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-4-yl]methyl (2R)-5-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid	Generator

Chemical Formula

C₂₀H₃₁NO₅

Average Mass

365.4700 Da

Monoisotopic Mass

365.22022 Da

IUPAC Name

[(5R,7R,8S,8aR)-7-hydroxy-5-(hydroxymethyl)-2,2,8-trimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-4-yl]methyl (2R)-5-oxopyrrolidine-2-carboxylate

Traditional Name

[(5R,7R,8S,8aR)-7-hydroxy-5-(hydroxymethyl)-2,2,8-trimethyl-3,5,6,7,8,8a-hexahydro-1H-azulen-4-yl]methyl (2R)-5-oxopyrrolidine-2-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2CC(C)(C)CC2=C(COC(=O)[C@H]2CCC(=O)N2)[C@H](CO)C[C@H]1O

InChI Identifier

InChI=1S/C20H31NO5/c1-11-13-7-20(2,3)8-14(13)15(12(9-22)6-17(11)23)10-26-19(25)16-4-5-18(24)21-16/h11-13,16-17,22-23H,4-10H2,1-3H3,(H,21,24)/t11-,12-,13+,16+,17+/m0/s1

InChI Key

IQKGQLSGOWFRNJ-IPJLKBMESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Conocybe siliginea	NPAtlas	18598081

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Pyrroline
Cyclic carboximidic acid
Carboxylic acid ester
Secondary alcohol
Lactim
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxide
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
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	0.77	ALOGPS
logP	0.49	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.4	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.17 m³·mol⁻¹	ChemAxon
Polarizability	40.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019906

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588623

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou ZY, Tang JG, Wang F, Dong ZJ, Liu JK: Sesquiterpenes and aliphatic diketones from cultures of the basidiomycete Conocybe siliginea. J Nat Prod. 2008 Aug;71(8):1423-6. doi: 10.1021/np8002657. Epub 2008 Jul 4. [PubMed:18598081 ]

Showing NP-Card for 5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate (NP0007845)

MOL for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

3D MOL for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

3D SDF for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

3D-SDF for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

PDB for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

3D PDB for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

SMILES for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

INCHI for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

Structure for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)

3D Structure for NP0007845 (5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate)