NP-MRD: Showing NP-Card for nodulisporic acid (NP0300955)

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Record Information

Version

2.0

Created at

2022-09-10 13:38:33 UTC

Updated at

2022-09-10 13:38:33 UTC

NP-MRD ID

NP0300955

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nodulisporic acid

Description

Nodulisporic Acid A, also known as nodulispate a, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. nodulisporic acid was first documented in 2008 (PMID: 18389234). Based on a literature review a small amount of articles have been published on Nodulisporic Acid A (PMID: 29326208) (PMID: 23056404) (PMID: 19445514) (PMID: 19136126).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102215382D          

 50 57  0  0  1  0            999 V2000
    8.0574   -4.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9786   -4.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6504   -3.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2280   -3.7554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5098   -4.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4288   -4.9824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6261   -3.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8438   -3.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976   -1.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0799   -2.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7981   -1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4062   -2.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3070   -1.7679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4292   -0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1317   -1.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3503   -1.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3873   -2.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6059   -1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0367   -2.3861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9998   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4712   -2.5764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
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 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  2  0  0  0  0
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 13 16  1  0  0  0  0
 16 17  1  6  0  0  0
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 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 21 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  1  0  0  0
 18 38  1  6  0  0  0
 12 38  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
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 41 44  1  0  0  0  0
 44 45  1  0  0  0  0
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 45 48  1  0  0  0  0
 48 39  1  6  0  0  0
 48 49  1  0  0  0  0
  8 49  1  0  0  0  0
 49 50  1  1  0  0  0
M  END

     RDKit          3D

103110  0  0  0  0  0  0  0  0999 V2000
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 36 16  1  0
 48 39  1  0
 11 15  1  0
 38 12  1  0
 22 21  1  0
  3 53  1  0
  3 54  1  0
  3 55  1  0
  1 51  1  0
  1 52  1  0
  4 56  1  6
 10 57  1  0
 17 58  1  0
 17 59  1  0
 17 60  1  0
 18 61  1  1
 38 86  1  0
 38 87  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  6
 37 83  1  0
 37 84  1  0
 37 85  1  0
 35 81  1  0
 35 82  1  0
 34 79  1  0
 34 80  1  0
 32 77  1  6
 33 78  1  0
 23 67  1  0
 23 68  1  0
 23 69  1  0
 24 70  1  0
 25 71  1  0
 26 72  1  0
 28 73  1  0
 28 74  1  0
 28 75  1  0
 31 76  1  0
 40 88  1  0
 42 89  1  0
 42 90  1  0
 42 91  1  0
 43 92  1  0
 43 93  1  0
 43 94  1  0
 46 95  1  0
 46 96  1  0
 46 97  1  0
 47 98  1  0
 47 99  1  0
 47100  1  0
 48101  1  1
 49102  1  6
 50103  1  0
M  END


  Mrv1652309102215382D          

 50 57  0  0  1  0            999 V2000
    8.0574   -4.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9786   -4.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6504   -3.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2280   -3.7554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5098   -4.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4288   -4.9824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6261   -3.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8438   -3.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976   -1.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0799   -2.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7981   -1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4062   -2.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.9469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2441   -2.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1243   -1.7903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2031   -2.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9601   -0.9818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5782   -0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3605   -0.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5247   -1.5058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3070   -1.7679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4292   -0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1317   -1.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5256   -1.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3503   -1.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7811   -1.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3873   -2.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6059   -1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0367   -2.3861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9998   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4712   -2.5764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2535   -2.8384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8531   -3.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0708   -2.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9066   -2.0523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4877   -2.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1405   -0.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8599   -2.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -1.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598   -1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6248   -0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7612   -1.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -2.3931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963   -3.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9516   -3.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9165   -3.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175   -2.9861    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1256   -3.5437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0320   -4.3633    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
  4  2  1  1  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  2  0  0  0  0
 11 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 21 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  1  0  0  0
 18 38  1  6  0  0  0
 12 38  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 39  1  6  0  0  0
 48 49  1  0  0  0  0
  8 49  1  0  0  0  0
 49 50  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0300955

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1N2C3=C(C1=O)C1=C(C=C3C3=C2[C@@]2(C)[C@H](C3)CC[C@@H]3[C@]2(C)CC[C@H](O)[C@@]3(C)\C=C\C=C(/C)C(O)=O)C2=CC(C)(C)OC(C)(C)[C@H]2[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C43H53NO6/c1-21(2)33-36(47)31-30-24(27-20-39(4,5)50-40(6,7)32(27)35(30)46)19-25-26-18-23-13-14-28-41(8,16-11-12-22(3)38(48)49)29(45)15-17-42(28,9)43(23,10)37(26)44(33)34(25)31/h11-12,16,19-20,23,28-29,32-33,35,45-46H,1,13-15,17-18H2,2-10H3,(H,48,49)/b16-11+,22-12+/t23-,28-,29-,32+,33-,35+,41-,42-,43+/m0/s1

> <INCHI_KEY>
UNCVXXVJJXJZII-QLETUHIQSA-N

> <FORMULA>
C43H53NO6

> <MOLECULAR_WEIGHT>
679.898

> <EXACT_MASS>
679.387288431

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
103

> <JCHEM_AVERAGE_POLARIZABILITY>
81.14586301789942

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E)-5-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-(prop-1-en-2-yl)-21-oxa-1-azaoctacyclo[13.13.1.0^{2,14}.0^{3,12}.0^{4,9}.0^{17,25}.0^{18,23}.0^{26,29}]nonacosa-2(14),15(29),16,18,25-pentaen-8-yl]-2-methylpenta-2,4-dienoic acid

> <JCHEM_LOGP>
6.600351135666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.737366186025168

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.702082965978666

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7026316445420385

> <JCHEM_POLAR_SURFACE_AREA>
108.99000000000001

> <JCHEM_REFRACTIVITY>
198.02980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-5-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-(prop-1-en-2-yl)-21-oxa-1-azaoctacyclo[13.13.1.0^{2,14}.0^{3,12}.0^{4,9}.0^{17,25}.0^{18,23}.0^{26,29}]nonacosa-2(14),15(29),16,18,25-pentaen-8-yl]-2-methylpenta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      15.041  -9.182   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.893  -7.649   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.147  -6.755   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.492  -7.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.152  -7.768   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.000  -9.300   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.502  -6.346   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.042  -5.857   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.735  -4.348   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.889  -3.328   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.349  -3.817   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.690  -3.059   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.825  -4.100   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      13.186  -5.501   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      11.656  -5.326   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.165  -3.342   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.313  -4.875   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.859  -1.833   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.013  -0.813   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.473  -1.302   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.779  -2.811   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.240  -3.300   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.468  -1.777   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.779  -3.260   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.514  -1.907   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.054  -1.867   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.858  -3.181   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      23.123  -4.534   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.398  -3.141   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      26.202  -4.454   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      26.133  -1.788   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      19.546  -4.809   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      21.006  -5.298   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      18.392  -5.829   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.932  -5.340   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.626  -3.831   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.844  -5.158   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.329  -1.658   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.205  -4.173   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.311  -2.919   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.778  -3.066   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.900  -1.531   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.287  -2.680   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       4.139  -4.467   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       5.033  -5.721   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.643  -6.384   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.444  -7.205   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.566  -5.574   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.701  -6.615   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       7.526  -8.145   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   15                                                  
CONECT    8    7    9   49                                                  
CONECT    9    8   10   39                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   38                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    4   15                                                  
CONECT   15   14    7   11                                                  
CONECT   16   13   17   18   36                                             
CONECT   17   16                                                            
CONECT   18   16   19   38                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   36                                                  
CONECT   22   21   23   24   32                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   22   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   21   16   37                                             
CONECT   37   36                                                            
CONECT   38   18   12                                                       
CONECT   39    9   40   48                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41   45                                                       
CONECT   45   44   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45   39   49                                                  
CONECT   49   48    8   50                                                  
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  114    0
END

View in JSmol

Synonyms

Value	Source
Nodulispate a	Generator
Nodulispic acid a	Generator
Nodulisporic acid-a	MeSH

Chemical Formula

C₄₃H₅₃NO₆

Average Mass

679.8980 Da

Monoisotopic Mass

679.38729 Da

IUPAC Name

(2E,4E)-5-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-(prop-1-en-2-yl)-21-oxa-1-azaoctacyclo[13.13.1.0^{2,14}.0^{3,12}.0^{4,9}.0^{17,25}.0^{18,23}.0^{26,29}]nonacosa-2(14),15(29),16,18,25-pentaen-8-yl]-2-methylpenta-2,4-dienoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1N2C3=C(C1=O)C1=C(C=C3C3=C2[C@@]2(C)[C@H](C3)CC[C@@H]3[C@]2(C)CC[C@H](O)[C@@]3(C)\C=C\C=C(/C)C(O)=O)C2=CC(C)(C)OC(C)(C)[C@H]2[C@@H]1O

InChI Identifier

InChI=1S/C43H53NO6/c1-21(2)33-36(47)31-30-24(27-20-39(4,5)50-40(6,7)32(27)35(30)46)19-25-26-18-23-13-14-28-41(8,16-11-12-22(3)38(48)49)29(45)15-17-42(28,9)43(23,10)37(26)44(33)34(25)31/h11-12,16,19-20,23,28-29,32-33,35,45-46H,1,13-15,17-18H2,2-10H3,(H,48,49)/b16-11+,22-12+/t23-,28-,29-,32+,33-,35+,41-,42-,43+/m0/s1

InChI Key

UNCVXXVJJXJZII-QLETUHIQSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
3-alkylindole
Indane
Indole
Indole or derivatives
Medium-chain fatty acid
Pyrrolizine
Aryl alkyl ketone
Aryl ketone
Amino fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Benzenoid
Pyran
Fatty acid
Fatty acyl
Unsaturated fatty acid
Cyclic alcohol
Heteroaromatic compound
Pyrrole
Vinylogous amide
Secondary alcohol
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organopnictogen compound
Organooxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	6.6	ChemAxon
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-0.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	198.03 m³·mol⁻¹	ChemAxon
Polarizability	81.15 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00026506

Chemspider ID

8922422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10747094

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nicholson MJ, Van de Bittner KC, Ram A, Bustamante LY, Scott B, Parker EJ: Draft Genome Sequence of the Filamentous Fungus Hypoxylon pulicicidum ATCC 74245. Genome Announc. 2018 Jan 11;6(2):e01380-17. doi: 10.1128/genomeA.01380-17. [PubMed:29326208 ]
Bills GF, Gonzalez-Menendez V, Martin J, Platas G, Fournier J, Persoh D, Stadler M: Hypoxylon pulicicidum sp. nov. (Ascomycota, Xylariales), a pantropical insecticide-producing endophyte. PLoS One. 2012;7(10):e46687. doi: 10.1371/journal.pone.0046687. Epub 2012 Oct 9. [PubMed:23056404 ]
Meinke PT, Colletti SL, Fisher MH, Wyvratt MJ, Shih TL, Ayer MB, Li C, Lim J, Ok D, Salva S, Warmke LM, Zakson M, Michael BF, Demontigny P, Ostlind DA, Fink D, Drag M, Schmatz DM, Shoop WL: Discovery of the development candidate N-tert-butyl nodulisporamide: a safe and efficacious once monthly oral agent for the control of fleas and ticks on companion animals. J Med Chem. 2009 Jun 11;52(11):3505-15. doi: 10.1021/jm801334v. [PubMed:19445514 ]
Mantle PG: The role of tryptophan as a biosynthetic precursor of indole-diterpenoid fungal metabolites: continuing a debate. Phytochemistry. 2009 Jan;70(1):7-10. doi: 10.1016/j.phytochem.2008.11.004. Epub 2009 Jan 10. [PubMed:19136126 ]
Ireland C, Peekhaus N, Lu P, Sangari R, Zhang A, Masurekar P, An Z: The tryptophan synthetase gene TRP1 of Nodulisporium sp.: molecular characterization and its relation to nodulisporic acid A production. Appl Microbiol Biotechnol. 2008 Jun;79(3):451-9. doi: 10.1007/s00253-008-1440-3. Epub 2008 Apr 4. [PubMed:18389234 ]
LOTUS database [Link]

Showing NP-Card for nodulisporic acid (NP0300955)

MOL for NP0300955 (nodulisporic acid)

3D MOL for NP0300955 (nodulisporic acid)

3D SDF for NP0300955 (nodulisporic acid)

3D-SDF for NP0300955 (nodulisporic acid)

PDB for NP0300955 (nodulisporic acid)

3D PDB for NP0300955 (nodulisporic acid)

SMILES for NP0300955 (nodulisporic acid)

INCHI for NP0300955 (nodulisporic acid)

Structure for NP0300955 (nodulisporic acid)

3D Structure for NP0300955 (nodulisporic acid)