NP-MRD: Showing NP-Card for (1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid (NP0305723)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 21:46:43 UTC

Updated at

2022-09-10 21:46:44 UTC

NP-MRD ID

NP0305723

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid

Description

Integric acid, also known as integrate, belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. (1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid was first documented in 2003 (PMID: 14529524). Based on a literature review a small amount of articles have been published on Integric acid (PMID: 29066795) (PMID: 25514836) (PMID: 24291042) (PMID: 19860426).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102223462D          

 31 32  0  0  1  0            999 V2000
  -10.0026    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5737    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    2.4750    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
  3  4  2  0  0  0  0
  5  2  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 65 66  0  0  0  0  0  0  0  0999 V2000
   -6.9475    0.4446   -0.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9717    1.2903   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2894    2.6206   -1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128    3.5028   -1.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774    0.8947   -0.5381 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3892   -0.5712   -0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8901   -0.8542   -0.2369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3055   -0.3673   -1.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.1238    0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534    1.0731    1.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8461    1.6867    0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1805    2.8695    0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1395   -0.6153    1.7091 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1128   -0.1621    1.2312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721    0.5792    2.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6124    0.8522    3.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975    1.0617    1.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517    1.8427    2.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494    0.7662    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856    1.1221   -0.3976 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6745    2.0611   -1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1628    1.2071    0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3771    0.9459   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854   -0.4002   -1.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -1.5322   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -2.1294    1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2469   -2.6017    0.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -2.3330   -0.0624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0744   -3.1354   -1.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -3.8664   -1.7615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913   -3.1839   -1.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9978    0.7093   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6988   -0.5473   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3571    2.8630   -1.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9890    1.0604   -1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -1.2319   -0.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6951   -0.6940    0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938   -0.9380   -1.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9888    0.6944   -1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9953   -0.4684   -2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3174    1.6488    2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2419   -0.2611    2.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750    2.8112    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312    1.2659    2.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6235    2.0011    3.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8666    0.1600   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0589    0.1321   -1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7844    1.6680   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5282    1.9828   -2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477    3.0852   -1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3173    2.1362    0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2991    0.3796    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4851    1.7071   -1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2628    1.0202    0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3922   -0.4950   -1.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -0.6021   -1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -1.8260    0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0074   -1.3046    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8095   -2.4212   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9366   -2.5625    2.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -2.4517    2.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0515   -3.6979    0.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5621   -2.0979   -0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190   -2.6633    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8445   -4.0068   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 31  1  0
 29 30  2  0
 28  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  5 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  2  0
  9 13  1  0
  9  7  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 24 55  1  0
 24 56  1  0
 23 53  1  0
 23 54  1  0
 22 51  1  0
 22 52  1  0
 20 47  1  6
 21 48  1  0
 21 49  1  0
 21 50  1  0
 19 46  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 13 42  1  1
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  1
 31 65  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  6 36  1  0
  6 37  1  0
  5 35  1  6
  1 32  1  0
  1 33  1  0
  3 34  1  0
 10 41  1  0
M  END


  Mrv1652309102223462D          

 31 32  0  0  1  0            999 V2000
  -10.0026    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5737    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    2.4750    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
  3  4  2  0  0  0  0
  5  2  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305723

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC(C)\C=C(/C)C(=O)O[C@@H]1CC[C@H](C(O)=O)[C@@]2(C)C[C@@H](C(=C)C=O)C(=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O6/c1-6-7-8-15(2)11-16(3)24(30)31-22-10-9-19(23(28)29)25(5)13-18(17(4)14-26)21(27)12-20(22)25/h11-12,14-15,18-19,22H,4,6-10,13H2,1-3,5H3,(H,28,29)/b16-11+/t15?,18-,19+,22+,25+/m0/s1

> <INCHI_KEY>
UIXJDFDDMXCJCT-KIBVBBMMSA-N

> <FORMULA>
C25H34O6

> <MOLECULAR_WEIGHT>
430.541

> <EXACT_MASS>
430.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.62618004290886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,7S,8aR)-4-{[(2E)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <JCHEM_LOGP>
4.972025682333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.116884252713785

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1689378549759475

> <JCHEM_PKA_STRONGEST_BASIC>
-5.014476299259062

> <JCHEM_POLAR_SURFACE_AREA>
97.74000000000001

> <JCHEM_REFRACTIVITY>
118.87739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,7S,8aR)-4-{[(2E)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic 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     -18.672  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.338  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.338  13.090   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -18.672  13.860   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -16.004  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -16.004   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -14.670   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.004   7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -13.337   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -13.337  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.670  11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -14.670  13.090   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -10.669   9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -14.670   6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.004   6.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -17.338   6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -16.004   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   28                                             
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   13   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    7   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
Integrate	Generator

Chemical Formula

C₂₅H₃₄O₆

Average Mass

430.5410 Da

Monoisotopic Mass

430.23554 Da

IUPAC Name

(1S,4R,7S,8aR)-4-{[(2E)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

(1S,4R,7S,8aR)-4-{[(2E)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCC(C)\C=C(/C)C(=O)O[C@@H]1CC[C@H](C(O)=O)[C@@]2(C)C[C@@H](C(=C)C=O)C(=O)C=C12

InChI Identifier

InChI=1S/C25H34O6/c1-6-7-8-15(2)11-16(3)24(30)31-22-10-9-19(23(28)29)25(5)13-18(17(4)14-26)21(27)12-20(22)25/h11-12,14-15,18-19,22H,4,6-10,13H2,1-3,5H3,(H,28,29)/b16-11+/t15?,18-,19+,22+,25+/m0/s1

InChI Key

UIXJDFDDMXCJCT-KIBVBBMMSA-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 eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclohexenone
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Alpha,beta-unsaturated aldehyde
Enal
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aldehyde
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.97	ChemAxon
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.74 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.88 m³·mol⁻¹	ChemAxon
Polarizability	47.63 Å³	ChemAxon
Number of Rings	2	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

5017169

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Integration

METLIN ID

Not Available

PubChem Compound

6531515

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tchoukoua A, Suzuki T, Ariefta NR, Koseki T, Okawa Y, Kimura KI, Shiono Y: A new eremophilane sesquiterpene from the fungus Xylaria sp. V-27 and inhibition activity against degranulation in RBL-2H3 cells. J Antibiot (Tokyo). 2017 Dec;70(12):1129-1132. doi: 10.1038/ja.2017.120. Epub 2017 Oct 25. [PubMed:29066795 ]
Srisapoomi T, Ichiyanagi T, Nakajima H, Aimi T, Boonlue S: Biosynthesis of integric acid isolated from the wood-decay fungus Xylaria feejeensis 2FB-PPM08M. Curr Microbiol. 2015 Apr;70(4):550-5. doi: 10.1007/s00284-014-0759-5. Epub 2014 Dec 17. [PubMed:25514836 ]
Pawar R, Das T, Mishra S, Nutan, Pancholi B, Gupta SK, Bhat SV: Synthesis, anti-HIV activity, integrase enzyme inhibition and molecular modeling of catechol, hydroquinone and quinol labdane analogs. Bioorg Med Chem Lett. 2014 Jan 1;24(1):302-7. doi: 10.1016/j.bmcl.2013.11.014. Epub 2013 Nov 18. [PubMed:24291042 ]
Waalboer DC, van Kalkeren HA, Schaapman MC, van Delft FL, Rutjes FP: Total synthesis and absolute stereochemistry of integric acid. J Org Chem. 2009 Nov 20;74(22):8878-81. doi: 10.1021/jo901845r. [PubMed:19860426 ]
Tziveleka LA, Vagias C, Roussis V: Natural products with anti-HIV activity from marine organisms. Curr Top Med Chem. 2003;3(13):1512-35. doi: 10.2174/1568026033451790. [PubMed:14529524 ]
LOTUS database [Link]

Showing NP-Card for (1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid (NP0305723)

MOL for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D MOL for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D SDF for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D-SDF for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

PDB for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D PDB for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

SMILES for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

INCHI for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

Structure for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D Structure for NP0305723 ((1s,4r,7s,8ar)-4-{[(2e)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)