NP-MRD: Showing NP-Card for terreuside A (NP0332301)

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Record Information

Version

2.0

Created at

2024-01-04 04:06:16 UTC

Updated at

2024-09-03 04:18:45 UTC

NP-MRD ID

NP0332301

Natural Product DOI

https://doi.org/10.57994/1503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

terreuside A

Description

Terreuside A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on terreuside A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01042404062D          

 51 59  0  0  1  0            999 V2000
   -6.7367    1.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9119    1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5149    0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9428   -0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5459   -0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6901    0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2623    1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6592    2.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2313    2.7353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6283    3.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4840    2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8810    2.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5292    3.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1302    4.0824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8534    3.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6994    2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3243    2.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1032    2.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2572    3.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6323    3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4592    1.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907    0.2956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6300    0.6148    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8521   -0.3293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299   -0.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596   -0.9386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7348   -0.9564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4969   -1.7464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1746   -2.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143   -2.5488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6031   -2.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5300   -3.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880   -2.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255   -1.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8112   -1.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382   -1.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0501   -0.7023    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1617    0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4904    0.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254    0.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -1.0500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -1.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6214   -1.9554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2800   -1.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -1.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103   -2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6482   -1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0830   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515   -0.0235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9123   -0.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
  2 11  1  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  7 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 27 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 27 34  1  6  0  0  0
 30 35  1  6  0  0  0
 35 36  1  0  0  0  0
 37 36  1  0  0  0  0
 27 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 26 41  1  6  0  0  0
 26 42  1  0  0  0  0
 29 42  1  0  0  0  0
 42 43  2  0  0  0  0
 24 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 44 49  1  0  0  0  0
 50 49  1  0  0  0  0
 22 50  1  0  0  0  0
 50  6  1  0  0  0  0
 50 51  1  1  0  0  0
M  END


  Mrv2104 01042404062D          

 51 59  0  0  1  0            999 V2000
   -6.7367    1.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9119    1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5149    0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9428   -0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5459   -0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6901    0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2623    1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6592    2.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2313    2.7353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6283    3.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4840    2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8810    2.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5292    3.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1302    4.0824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8534    3.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6994    2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3243    2.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1032    2.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2572    3.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6323    3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4592    1.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3907    0.2956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6300    0.6148    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8521   -0.3293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299   -0.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596   -0.9386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7348   -0.9564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4969   -1.7464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1746   -2.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143   -2.5488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6031   -2.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5300   -3.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880   -2.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255   -1.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8112   -1.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382   -1.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0501   -0.7023    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1617    0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4904    0.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254    0.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -1.0500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -1.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6214   -1.9554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2800   -1.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -1.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103   -2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6482   -1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0830   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515   -0.0235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9123   -0.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
  2 11  1  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  7 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 27 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 27 34  1  6  0  0  0
 30 35  1  6  0  0  0
 35 36  1  0  0  0  0
 37 36  1  0  0  0  0
 27 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 26 41  1  6  0  0  0
 26 42  1  0  0  0  0
 29 42  1  0  0  0  0
 42 43  2  0  0  0  0
 24 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 44 49  1  0  0  0  0
 50 49  1  0  0  0  0
 22 50  1  0  0  0  0
 50  6  1  0  0  0  0
 50 51  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0332301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CN2C3=CC=CC=C3[C@]3(O)C4=C(O[C@]23[H])C(OC)=C(C2=CNC3=C2C=CC=C3)C(O)=C4OC)C(=O)C[C@H]2[C@@H]3CC[C@H](C(O)=O)[C@]12CC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C39H40N2O8/c1-37(2)18-38-23(35(44)45)14-13-21(37)24(38)15-28(42)25(38)17-41-27-12-8-6-10-22(27)39(46)30-33(48-4)31(43)29(32(47-3)34(30)49-36(39)41)20-16-40-26-11-7-5-9-19(20)26/h5-12,16,21,23-25,36,40,43,46H,13-15,17-18H2,1-4H3,(H,44,45)/t21-,23+,24-,25+,36-,38-,39-/m0/s1

> <INCHI_KEY>
MDLXGXWNGADDEZ-RJNKUXNJSA-N

> <FORMULA>
C39H40N2O8

> <MOLECULAR_WEIGHT>
664.755

> <EXACT_MASS>
664.278466256

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
70.9773458287534

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6S,9S)-2-{[(1S,9S)-1,4-dihydroxy-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaen-10-yl]methyl}-11,11-dimethyl-3-oxotricyclo[4.3.2.0^{1,5}]undecane-9-carboxylic acid

> <JCHEM_LOGP>
5.592484076333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.864056813196173

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9298565578500875

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2915697671768624

> <JCHEM_POLAR_SURFACE_AREA>
141.54999999999998

> <JCHEM_REFRACTIVITY>
180.7851

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6S,9S)-2-{[(1S,9S)-1,4-dihydroxy-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaen-10-yl]methyl}-11,11-dimethyl-3-oxotricyclo[4.3.2.0^{1,5}]undecane-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JAN-24         0                                  
HETATM    1  O   UNK     0     -12.575   2.539   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0     -11.036   2.506   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.295   1.156   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -11.093  -0.161   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -10.352  -1.511   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.755   1.123   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.956   2.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.697   3.789   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.899   5.106   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -8.639   6.456   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.237   3.823   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.978   5.173   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.321   6.566   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0     -11.443   7.621   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0     -12.793   6.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.506   5.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -13.672   4.361   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -15.126   4.869   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -15.413   6.382   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.247   7.387   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.457   2.087   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.329   0.552   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -4.909   1.148   0.000  0.00  0.00           H+0
HETATM   24  N   UNK     0      -5.324  -0.615   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -3.789  -0.487   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.911  -1.752   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.372  -1.785   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.927  -3.260   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.193  -4.138   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.400  -4.758   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.126  -4.549   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.989  -6.083   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.591  -5.024   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.914  -3.227   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.514  -3.695   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.378  -2.161   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.094  -1.311   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.302   0.215   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.915   1.158   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.727   0.797   0.000  0.00  0.00           O+0
HETATM   41  H   UNK     0      -4.437  -1.960   0.000  0.00  0.00           H+0
HETATM   42  C   UNK     0      -3.419  -3.206   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -4.893  -3.650   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -6.123  -1.931   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -5.679  -3.406   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -6.733  -4.528   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -8.233  -4.175   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -8.677  -2.701   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -7.622  -1.579   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -7.749  -0.044   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -9.170  -0.640   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   50                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8    2   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    7   22                                                       
CONECT   22   21   23   24   50                                             
CONECT   23   22                                                            
CONECT   24   22   25   44                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   41   42                                             
CONECT   27   26   28   34   37                                             
CONECT   28   27   29   30                                                  
CONECT   29   28   42                                                       
CONECT   30   28   31   35                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   27                                                       
CONECT   35   30   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   27   38                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   26                                                            
CONECT   42   26   29   43                                                  
CONECT   43   42                                                            
CONECT   44   24   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   44   50                                                  
CONECT   50   49   22    6   51                                             
CONECT   51   50                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₄₀N₂O₈

Average Mass

664.7550 Da

Monoisotopic Mass

664.27847 Da

IUPAC Name

(1S,2R,5S,6S,9S)-2-{[(1S,9S)-1,4-dihydroxy-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaen-10-yl]methyl}-11,11-dimethyl-3-oxotricyclo[4.3.2.0^{1,5}]undecane-9-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CN2C3=CC=CC=C3[C@]3(O)C4=C(O[C@]23[H])C(OC)=C(C2=CNC3=C2C=CC=C3)C(O)=C4OC)C(=O)C[C@H]2[C@@H]3CC[C@H](C(O)=O)[C@]12CC3(C)C

InChI Identifier

InChI=1S/C39H40N2O8/c1-37(2)18-38-23(35(44)45)14-13-21(37)24(38)15-28(42)25(38)17-41-27-12-8-6-10-22(27)39(46)30-33(48-4)31(43)29(32(47-3)34(30)49-36(39)41)20-16-40-26-11-7-5-9-19(20)26/h5-12,16,21,23-25,36,40,43,46H,13-15,17-18H2,1-4H3,(H,44,45)/t21-,23+,24-,25+,36-,38-,39-/m0/s1

InChI Key

MDLXGXWNGADDEZ-RJNKUXNJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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-phenylpyrrole
Coumaran
Indole or derivatives
Indole
Dialkylarylamine
Anisole
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Alkyl aryl ether
Fatty acyl
Benzenoid
N-alkylpyrrolidine
Substituted pyrrole
Heteroaromatic compound
Tertiary alcohol
Pyrrolidine
Pyrrole
Dihydrofuran
Amino acid
Cyclic ketone
Ketone
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Ether
Secondary aliphatic amine
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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	5.59	ChemAxon
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.55 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	180.79 m³·mol⁻¹	ChemAxon
Polarizability	70.98 Å³	ChemAxon
Number of Rings	9	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for terreuside A (NP0332301)

MOL for NP0332301 (terreuside A)

3D MOL for NP0332301 (terreuside A)

3D SDF for NP0332301 (terreuside A)

3D-SDF for NP0332301 (terreuside A)

PDB for NP0332301 (terreuside A)

3D PDB for NP0332301 (terreuside A)

SMILES for NP0332301 (terreuside A)

INCHI for NP0332301 (terreuside A)

Structure for NP0332301 (terreuside A)

3D Structure for NP0332301 (terreuside A)