NP-MRD: Showing NP-Card for (2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid (NP0250242)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 13:01:24 UTC

Updated at

2022-09-07 13:01:24 UTC

NP-MRD ID

NP0250242

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid

Description

Homopetasinic acid, also known as homopetasinate, 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. Based on a literature review very few articles have been published on Homopetasinic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072215012D          

 30 31  0  0  1  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 14 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 62 63  0  0  0  0  0  0  0  0999 V2000
   -6.4434   -1.7816    2.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1219   -0.8714    1.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0443   -0.6859    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9696    0.0011    1.8419 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1228   -0.2534    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075    0.5958    0.5163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2808    1.8042   -0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3714    1.1157    1.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9010    0.8468    2.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1018   -0.0185    3.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2386   -0.6761    4.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1748    1.9782    1.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    2.0288    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6288    0.7835   -0.4642 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6274    0.1083   -0.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3425   -0.0615   -1.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510    0.4155   -2.7626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6499   -0.7673   -1.7803 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1693   -0.7864   -3.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -0.0261   -0.9065 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1914    0.0172    0.4288 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9932   -0.5906   -0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0191    0.0903   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3460   -0.4852   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4193    0.1389   -0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7463   -0.4467   -0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7345    0.1838    0.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9659   -1.6930   -0.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7330   -0.1479   -0.1181 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1950   -0.9931   -1.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3559   -2.3788    2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8989   -2.0318    3.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1055    0.3977    0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5270   -1.1520   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0372   -1.1390    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3677    1.0722    1.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9005   -1.3533    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893   -0.0880   -0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2047    2.7578    0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3537    1.7696   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    1.8377   -1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4823    1.2447    3.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5213    3.0122    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    1.7337    2.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8598    2.9389   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576    2.2079    0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251    1.1024   -1.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814   -1.8027   -1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3906   -0.9299   -3.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905    0.1273   -3.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -1.6516   -3.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378    1.0338   -1.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6705    0.8525    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1840   -1.5600   -1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8576    1.0806   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4757   -1.4569   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2551    1.1113    0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3613   -2.0734   -1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -0.8565    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3713   -1.0312   -2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3949   -2.0424   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661   -0.5462   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6 29  1  0
 29 30  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 29 14  1  0
  6  8  1  0
 19 49  1  0
 19 50  1  0
 19 51  1  0
 18 48  1  1
 20 52  1  6
 21 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  0
 28 58  1  0
 14 47  1  6
 13 45  1  0
 13 46  1  0
 12 43  1  0
 12 44  1  0
  9 42  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
 29 59  1  1
 30 60  1  0
 30 61  1  0
 30 62  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652309072215012D          

 30 31  0  0  1  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 14 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0250242

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@@H](O)\C=C\C=C\C(O)=O)C(=O)O[C@@H]1CCC2=CC(=O)[C@@H](C[C@]2(C)[C@H]1C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-14(2)18-13-24(5)16(4)21(11-10-17(24)12-20(18)26)30-23(29)15(3)19(25)8-6-7-9-22(27)28/h6-9,12,15-16,18-19,21,25H,1,10-11,13H2,2-5H3,(H,27,28)/b8-6+,9-7+/t15-,16-,18-,19-,21+,24+/m0/s1

> <INCHI_KEY>
MMWCHIIGAIJQMV-DHCANEKFSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.91893900962609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6S,7S)-8-{[(1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid

> <JCHEM_LOGP>
3.795286519333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.322727842948527

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.220245907095591

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0952678411215766

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
116.28359999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6S,7S)-8-{[(1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      16.004   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   29                                             
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   14    6   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
Homopetasinate	Generator

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@@H](O)\C=C\C=C\C(O)=O)C(=O)O[C@@H]1CCC2=CC(=O)[C@@H](C[C@]2(C)[C@H]1C)C(C)=C

InChI Identifier

InChI=1S/C24H32O6/c1-14(2)18-13-24(5)16(4)21(11-10-17(24)12-20(18)26)30-23(29)15(3)19(25)8-6-7-9-22(27)28/h6-9,12,15-16,18-19,21,25H,1,10-11,13H2,2-5H3,(H,27,28)/b8-6+,9-7+/t15-,16-,18-,19-,21+,24+/m0/s1

InChI Key

MMWCHIIGAIJQMV-DHCANEKFSA-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
Medium-chain hydroxy acid
Medium-chain fatty acid
Cyclohexenone
Hydroxy fatty acid
Fatty acid ester
Branched fatty acid
Beta-hydroxy acid
Fatty acyl
Unsaturated fatty acid
Hydroxy acid
Dicarboxylic acid or derivatives
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

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

78436226

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132837508

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid (NP0250242)

MOL for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

3D MOL for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

3D SDF for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

3D-SDF for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

PDB for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

3D PDB for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

SMILES for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

INCHI for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

Structure for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)

3D Structure for NP0250242 ((2e,4e,6s,7s)-8-{[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl]oxy}-6-hydroxy-7-methyl-8-oxoocta-2,4-dienoic acid)