NP-MRD: Showing NP-Card for methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate (NP0177248)

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Record Information

Version

2.0

Created at

2022-09-03 15:03:39 UTC

Updated at

2022-09-03 15:03:39 UTC

NP-MRD ID

NP0177248

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate

Description

NEGUNDOIN A belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate is found in Vitex negundo. methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate was first documented in 2013 (PMID: 24060986). Based on a literature review very few articles have been published on NEGUNDOIN A (PMID: 24735394).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032217032D          

 27 29  0  0  1  0            999 V2000
    4.8093    3.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    2.9919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8738    2.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4974    1.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0942    1.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9383    1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020    0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034   -0.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2932   -0.0670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1912    0.7516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -0.8706    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2697   -1.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -1.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015   -0.3910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1121   -0.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749    0.6523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8643    0.8920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513    1.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407    1.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490    2.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    1.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3168    0.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    0.1727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9025    0.8950    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -7.7126    1.5254    0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5184    1.2620    0.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4140    0.6482    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5226    0.3271   -1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1932    0.3956    0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558   -0.1896    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1255   -0.6228   -1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504   -1.1882   -1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0200   -1.0462    0.0736 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9515   -0.4848    0.9759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307   -2.4497    0.5971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7166   -2.5219    2.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261   -3.1117   -0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891   -2.1163   -0.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -0.9207   -0.0046 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6724   -0.1075   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824    0.2911   -1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8389   -1.0775    0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401    1.0809    0.6627 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2990    2.1473   -0.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5345    2.6672    0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1556    3.7980   -0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080    2.2224    1.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5062    1.5470    1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3096    0.6863    1.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -0.1493    0.0338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0076    0.8418   -1.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5635    1.6197    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9301    0.7007   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6414    2.4660   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561    0.6908    1.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904    0.2484   -1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9386   -1.3731   -1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912   -2.2717   -1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -0.7244   -2.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6401   -3.0554    0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274   -1.6502    2.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2947   -3.4167    2.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2619   -2.5940    2.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1631   -3.9766   -0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1001   -3.5091    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2619   -2.6467   -1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8435   -1.9114   -1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046   -1.3286    1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5583    1.3350   -1.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915    0.3075   -1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -0.4434   -2.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938   -1.6695   -0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573   -1.7844    0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7248   -0.5284    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850    0.8420    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766    3.7929   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9201    4.7657   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2395    3.6721   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1781    2.5469    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7078    1.8258    2.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6151    1.2587    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429   -0.0691    2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461    1.8365   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149    1.0600   -1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060    0.5301   -2.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 10  6  1  0
 26 15  1  0
 26  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  6
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  1
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  1
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
M  END


  Mrv1652309032217032D          

 27 29  0  0  1  0            999 V2000
    4.8093    3.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    2.9919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8738    2.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4974    1.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0942    1.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9383    1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020    0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034   -0.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2932   -0.0670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1912    0.7516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -0.8706    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2697   -1.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -1.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015   -0.3910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1121   -0.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749    0.6523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8643    0.8920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513    1.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407    1.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490    2.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    1.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3168    0.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    0.1727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9025    0.8950    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0177248

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C1/CC[C@@]2(O1)[C@H](C)CC[C@H]1C(C)(C)[C@H](CC[C@]21C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O5/c1-14-7-8-17-20(3,4)18(26-15(2)23)10-11-21(17,5)22(14)12-9-16(27-22)13-19(24)25-6/h13-14,17-18H,7-12H2,1-6H3/b16-13+/t14-,17+,18+,21+,22-/m1/s1

> <INCHI_KEY>
IFXOQBCVGIFCLI-VSSSNARASA-N

> <FORMULA>
C22H34O5

> <MOLECULAR_WEIGHT>
378.509

> <EXACT_MASS>
378.240624195

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.86449742931013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1R,2R,4aS,6S,8aS)-6-(acetyloxy)-2,5,5,8a-tetramethyl-octahydro-2H-spiro[naphthalene-1,2'-oxolane]-5'-ylidene]acetate

> <JCHEM_LOGP>
3.8967153203333322

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.833266124488841

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
103.28509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,4aS,6S,8aS)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxolane]-5'-ylideneacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.977   6.089   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.522   5.585   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.231   4.073   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.395   3.064   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.776   3.569   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.485   2.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.537   0.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.793  -0.416   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.281  -0.125   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.090   1.403   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.630  -1.625   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.103  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.505  -2.677   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.032  -2.230   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.683  -0.730   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.209  -0.282   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.024  -1.811   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.328  -0.366   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.140   1.218   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.613   1.665   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.963   3.165   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.436   3.613   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.838   4.217   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.985   2.270   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.458   1.822   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.807   0.322   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.551   1.671   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   26                                             
CONECT   10    9    6                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   15    9   27                                             
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₅

Average Mass

378.5090 Da

Monoisotopic Mass

378.24062 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C1/CC[C@@]2(O1)[C@H](C)CC[C@H]1C(C)(C)[C@H](CC[C@]21C)OC(C)=O

InChI Identifier

InChI=1S/C22H34O5/c1-14-7-8-17-20(3,4)18(26-15(2)23)10-11-21(17,5)22(14)12-9-16(27-22)13-19(24)25-6/h13-14,17-18H,7-12H2,1-6H3/b16-13+/t14-,17+,18+,21+,22-/m1/s1

InChI Key

IFXOQBCVGIFCLI-VSSSNARASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vitex negundo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

24643360

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46229707

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tapia R, Bouanou H, Alvarez E, Alvarez-Manzaneda R, Chahboun R, Alvarez-Manzaneda E: Stereoselective transformations of (+)-abietic acid into (+)-vitedoin B and (+)-negundoin A. J Org Chem. 2014 May 16;79(10):4405-13. doi: 10.1021/jo5003533. Epub 2014 Apr 24. [PubMed:24735394 ]
Tapia R, Cano MJ, Bouanou H, Alvarez E, Alvarez-Manzaneda R, Chahboun R, Alvarez-Manzaneda E: I2-PPh3 mediated spiroannulation of unsaturated beta-dicarbonyl compounds. The first synthesis of (+/-)-negundoin A. Chem Commun (Camb). 2013 Nov 11;49(87):10257-9. doi: 10.1039/c3cc45921g. [PubMed:24060986 ]
LOTUS database [Link]

Showing NP-Card for methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate (NP0177248)

MOL for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

3D MOL for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

3D SDF for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

3D-SDF for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

PDB for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

3D PDB for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

SMILES for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

INCHI for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

Structure for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)

3D Structure for NP0177248 (methyl 2-[(1r,2r,4as,6s,8as)-6-(acetyloxy)-2,5,5,8a-tetramethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxolan]-5'-ylidene]acetate)