NP-MRD: Showing NP-Card for tricycloalternarene A (NP0042921)

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Record Information

Version

2.0

Created at

2021-06-21 00:27:51 UTC

Updated at

2021-06-30 00:18:18 UTC

NP-MRD ID

NP0042921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tricycloalternarene A

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2431878 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. tricycloalternarene A is found in Alternaria sp. JJY-32. tricycloalternarene A was first documented in 2013 (Zhang, G., et al.). Based on a literature review very few articles have been published on CHEMBL2431878.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102273D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102273D          

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    2.7185    1.4999    0.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504    2.7425    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    1.7793   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578    1.5008    0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768    0.8891    1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155    2.5826    1.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083   -0.8666    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396   -0.9039   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9368    0.1113   -1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129   -1.7091   -3.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851   -2.7570   -1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835   -3.6171    0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -4.2992   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -3.0531    0.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7565   -3.1520   -2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313   -0.4142   -3.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405    0.9907   -2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.5250    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131   -2.4876    1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2686   -1.4784   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0829   -2.2906   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    0.7343   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8742   -0.3667   -3.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 19  1  1  0  0  0
 19 18  1  0  0  0  0
 17 16  1  0  0  0  0
  9  7  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 22 20  1  0  0  0  0
  5  4  1  0  0  0  0
 23 24  1  0  0  0  0
  4  2  2  3  0  0  0
 24 17  1  0  0  0  0
  2  1  1  0  0  0  0
 18 20  1  0  0  0  0
 24 25  2  0  0  0  0
 18 17  2  0  0  0  0
 12 13  1  0  0  0  0
 11 12  1  0  0  0  0
  2  3  1  0  0  0  0
 15  9  1  0  0  0  0
 12 14  1  6  0  0  0
 22 23  1  0  0  0  0
 20 21  1  0  0  0  0
 12 15  1  0  0  0  0
  9 41  1  1  0  0  0
 15 16  1  0  0  0  0
  7  8  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  0  0  0  0
 11 45  1  0  0  0  0
 22 54  1  0  0  0  0
 22 55  1  0  0  0  0
 23 56  1  0  0  0  0
 23 57  1  0  0  0  0
 20 52  1  1  0  0  0
 16 50  1  0  0  0  0
 16 51  1  0  0  0  0
  7 37  1  6  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  4 32  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 13 46  1  0  0  0  0
 13 47  1  0  0  0  0
 13 48  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
 14 49  1  0  0  0  0
 21 53  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C2=C(C(=O)C([H])([H])C1([H])[H])C([H])([H])[C@]1(O2)[C@@]([H])(C([H])([H])C([H])([H])[C@@]1(O[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-13(2)6-5-7-14(3)16-10-11-20(4,24)21(16)12-15-17(22)8-9-18(23)19(15)25-21/h6,14,16,18,23-24H,5,7-12H2,1-4H3/t14-,16-,18+,20-,21-/m0/s1

> <INCHI_KEY>
LWDAODLUJBKNKG-CTINQRGJSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.483

> <EXACT_MASS>
348.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.1134449020006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,2'S,5'S,7R)-2',7-dihydroxy-2'-methyl-5'-[(2S)-6-methylhept-5-en-2-yl]-4,5,6,7-tetrahydro-3H-spiro[1-benzofuran-2,1'-cyclopentane]-4-one

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.8596232883333337

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.149756567845237

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.546383729483576

> <JCHEM_PKA_STRONGEST_BASIC>
-3.297480069509879

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
99.85149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,2'S,5'S,7R)-2',7-dihydroxy-2'-methyl-5'-[(2S)-6-methylhept-5-en-2-yl]-3,5,6,7-tetrahydrospiro[1-benzofuran-2,1'-cyclopentane]-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    5.0846   -0.3896    2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7751    0.9519    2.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9649    1.6412    3.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625    1.5394    2.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695    0.9888    2.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9040    1.6550    0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    1.1870    0.1385 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6102    1.5551    1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5719   -0.3180   -0.2405 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196   -0.6980   -1.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641   -1.9382   -1.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1179   -2.3067   -1.4166 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0004   -3.3652   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025   -2.8877   -2.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781   -0.9233   -0.9334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2610   -0.0755   -2.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7000   -0.2869   -1.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9032   -0.8665   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490   -1.1438    0.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341   -1.2584   -0.1473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1248   -2.5253    0.4898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2635   -1.3685   -1.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2204   -0.1708   -2.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8162    0.0963   -2.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6047    0.6725   -3.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2458   -0.8231    1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3762   -1.0971    2.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9145   -0.2994    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    1.8136    2.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7044    2.6115    3.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3895    1.0224    4.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4682    2.5258    3.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -0.0971    1.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.1813    2.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185    1.4999    0.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504    2.7425    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    1.7793   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578    1.5008    0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768    0.8891    1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155    2.5826    1.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083   -0.8666    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396   -0.9039   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9368    0.1113   -1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129   -1.7091   -3.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851   -2.7570   -1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835   -3.6171    0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -4.2992   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -3.0531    0.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7565   -3.1520   -2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313   -0.4142   -3.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405    0.9907   -2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.5250    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131   -2.4876    1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2686   -1.4784   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0829   -2.2906   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    0.7343   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8742   -0.3667   -3.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 19  1  1
 19 18  1  0
 17 16  1  0
  9  7  1  0
  9 10  1  0
  7  6  1  0
 10 11  1  0
  6  5  1  0
 22 20  1  0
  5  4  1  0
 23 24  1  0
  4  2  2  3
 24 17  1  0
  2  1  1  0
 18 20  1  0
 24 25  2  0
 18 17  2  0
 12 13  1  0
 11 12  1  0
  2  3  1  0
 15  9  1  0
 12 14  1  6
 22 23  1  0
 20 21  1  0
 12 15  1  0
  9 41  1  1
 15 16  1  0
  7  8  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 20 52  1  1
 16 50  1  0
 16 51  1  0
  7 37  1  6
  6 35  1  0
  6 36  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 14 49  1  0
 21 53  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       5.085  -0.390   2.029  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.775   0.952   2.634  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.965   1.641   3.250  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.563   1.539   2.642  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.269   0.989   2.104  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.904   1.655   0.773  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.569   1.187   0.139  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.610   1.555   1.046  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.572  -0.318  -0.241  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.720  -0.698  -1.194  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.264  -1.938  -1.970  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.118  -2.307  -1.417  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.365  -0.309  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.903  -2.888  -2.458  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.678  -0.923  -0.933  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.261  -0.076  -2.100  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.700  -0.287  -1.873  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.903  -0.867  -0.697  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.749  -1.144   0.029  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.234  -1.258  -0.147  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.125  -2.525   0.490  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.263  -1.369  -1.277  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.220  -0.171  -2.227  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.816   0.096  -2.744  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.605   0.673  -3.806  0.00  0.00           O+0
HETATM   26  H   UNK     0       4.246  -0.823   1.480  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.376  -1.097   2.812  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.915  -0.299   1.320  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.738   1.814   2.494  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.704   2.611   3.686  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.389   1.022   4.048  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.468   2.526   3.097  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.321  -0.097   1.996  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.491   1.181   2.851  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.719   1.500   0.054  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.850   2.743   0.923  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.467   1.779  -0.779  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.558   1.501   0.503  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.677   0.889   1.912  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.516   2.583   1.413  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.708  -0.867   0.700  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.640  -0.904  -0.637  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.937   0.111  -1.901  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.213  -1.709  -3.041  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.985  -2.757  -1.867  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.984  -3.617   0.102  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.404  -4.299  -0.718  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.649  -3.053   0.514  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.757  -3.152  -2.070  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.931  -0.414  -3.086  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.040   0.991  -2.019  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.558  -0.525   0.599  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.313  -2.488   1.029  0.00  0.00           H+0
HETATM   54  H   UNK     0      -6.269  -1.478  -0.852  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.083  -2.291  -1.848  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.572   0.734  -1.720  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.874  -0.367  -3.084  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   29   30   31                                             
CONECT    4    5    2   32                                                  
CONECT    5    6    4   33   34                                             
CONECT    6    7    5   35   36                                             
CONECT    7    9    6    8   37                                             
CONECT    8    7   38   39   40                                             
CONECT    9    7   10   15   41                                             
CONECT   10    9   11   42   43                                             
CONECT   11   10   12   44   45                                             
CONECT   12   13   11   14   15                                             
CONECT   13   12   46   47   48                                             
CONECT   14   12   49                                                       
CONECT   15   19    9   12   16                                             
CONECT   16   17   15   50   51                                             
CONECT   17   16   24   18                                                  
CONECT   18   19   20   17                                                  
CONECT   19   15   18                                                       
CONECT   20   22   18   21   52                                             
CONECT   21   20   53                                                       
CONECT   22   20   23   54   55                                             
CONECT   23   24   22   56   57                                             
CONECT   24   23   17   25                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
CONECT   56   23                                                            
CONECT   57   23                                                            
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
    5.0846   -0.3896    2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7751    0.9519    2.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9649    1.6412    3.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625    1.5394    2.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695    0.9888    2.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9040    1.6550    0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    1.1870    0.1385 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6102    1.5551    1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5719   -0.3180   -0.2405 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196   -0.6980   -1.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641   -1.9382   -1.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1179   -2.3067   -1.4166 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0004   -3.3652   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025   -2.8877   -2.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781   -0.9233   -0.9334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2610   -0.0755   -2.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7000   -0.2869   -1.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9032   -0.8665   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490   -1.1438    0.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341   -1.2584   -0.1473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1248   -2.5253    0.4898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2635   -1.3685   -1.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2204   -0.1708   -2.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8162    0.0963   -2.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6047    0.6725   -3.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2458   -0.8231    1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3762   -1.0971    2.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9145   -0.2994    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    1.8136    2.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7044    2.6115    3.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3895    1.0224    4.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4682    2.5258    3.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -0.0971    1.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.1813    2.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185    1.4999    0.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504    2.7425    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    1.7793   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578    1.5008    0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768    0.8891    1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155    2.5826    1.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083   -0.8666    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396   -0.9039   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9368    0.1113   -1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129   -1.7091   -3.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851   -2.7570   -1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835   -3.6171    0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -4.2992   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -3.0531    0.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7565   -3.1520   -2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313   -0.4142   -3.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405    0.9907   -2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.5250    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131   -2.4876    1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2686   -1.4784   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0829   -2.2906   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725    0.7343   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8742   -0.3667   -3.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 19  1  1
 19 18  1  0
 17 16  1  0
  9  7  1  0
  9 10  1  0
  7  6  1  0
 10 11  1  0
  6  5  1  0
 22 20  1  0
  5  4  1  0
 23 24  1  0
  4  2  2  3
 24 17  1  0
  2  1  1  0
 18 20  1  0
 24 25  2  0
 18 17  2  0
 12 13  1  0
 11 12  1  0
  2  3  1  0
 15  9  1  0
 12 14  1  6
 22 23  1  0
 20 21  1  0
 12 15  1  0
  9 41  1  1
 15 16  1  0
  7  8  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 20 52  1  1
 16 50  1  0
 16 51  1  0
  7 37  1  6
  6 35  1  0
  6 36  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 14 49  1  0
 21 53  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₄

Average Mass

348.4830 Da

Monoisotopic Mass

348.23006 Da

IUPAC Name

(2S,2'S,5'S,7R)-2',7-dihydroxy-2'-methyl-5'-[(2S)-6-methylhept-5-en-2-yl]-4,5,6,7-tetrahydro-3H-spiro[1-benzofuran-2,1'-cyclopentane]-4-one

Traditional Name

(2S,2'S,5'S,7R)-2',7-dihydroxy-2'-methyl-5'-[(2S)-6-methylhept-5-en-2-yl]-3,5,6,7-tetrahydrospiro[1-benzofuran-2,1'-cyclopentane]-4-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C2=C(C(=O)C([H])([H])C1([H])[H])C([H])([H])[C@]1(O2)[C@@]([H])(C([H])([H])C([H])([H])[C@@]1(O[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H32O4/c1-13(2)6-5-7-14(3)16-10-11-20(4,24)21(16)12-15-17(22)8-9-18(23)19(15)25-21/h6,14,16,18,23-24H,5,7-12H2,1-4H3/t14-,16-,18+,20-,21-/m0/s1

InChI Key

LWDAODLUJBKNKG-CTINQRGJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alternaria sp. JJY-32	JEOL database	Zhang, G., et al, J. Nat. Prod. 76, 1946 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Benzofuran
Cyclohexenone
Cyclic alcohol
Dihydrofuran
Tertiary alcohol
Vinylogous ester
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	2.9	ALOGPS
logP	2.86	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.85 m³·mol⁻¹	ChemAxon
Polarizability	40.11 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30771193

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72704483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, G., et al. (2013). Zhang, G., et al, J. Nat. Prod. 76, 1946 (2013). J. Nat. Prod..

Showing NP-Card for tricycloalternarene A (NP0042921)

MOL for NP0042921 (tricycloalternarene A)

3D MOL for NP0042921 (tricycloalternarene A)

3D SDF for NP0042921 (tricycloalternarene A)

3D-SDF for NP0042921 (tricycloalternarene A)

PDB for NP0042921 (tricycloalternarene A)

3D PDB for NP0042921 (tricycloalternarene A)

SMILES for NP0042921 (tricycloalternarene A)

INCHI for NP0042921 (tricycloalternarene A)

Structure for NP0042921 (tricycloalternarene A)

3D Structure for NP0042921 (tricycloalternarene A)