NP-MRD: Showing NP-Card for methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate (NP0257742)

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Record Information

Version

2.0

Created at

2022-09-07 22:57:10 UTC

Updated at

2022-09-07 22:57:10 UTC

NP-MRD ID

NP0257742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate

Description

Methyl galbanate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate is found in Ferula assa-foetida. methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate was first documented in 2007 (PMID: 17196626). Based on a literature review a significant number of articles have been published on methyl galbanate (PMID: 32364046) (PMID: 26953526) (PMID: 22440297) (PMID: 26004404) (PMID: 24328450) (PMID: 21246298).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082200572D          

 30 32  0  0  1  0            999 V2000
    3.1381   -4.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   -3.9894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670   -4.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670   -5.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -3.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960   -4.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7104   -3.9894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7104   -3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960   -2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960   -1.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249   -2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1394   -3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1394   -3.9894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8539   -4.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249   -4.4019    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8122   -5.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0376   -5.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4748   -5.8300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2993   -5.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6866   -5.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5111   -5.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9483   -5.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7728   -5.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2100   -6.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8226   -7.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2598   -7.8426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9982   -7.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5610   -6.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7365   -6.5009    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  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  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  6  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 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
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  2  0  0  0  0
 20 30  1  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -3.1541    3.6146    3.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6339    2.9834    2.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    2.3094    1.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5637    2.3166    1.6651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3015    1.6557    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2478    0.8984   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6581   -0.2453    0.1033 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6344   -1.3006    0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -1.7296   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4595   -2.8518    0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2316   -1.2947   -1.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1732   -2.0860    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510   -2.1431    1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2656   -2.1990    0.1605 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0437   -2.8748   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4228   -0.8760   -0.5503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6295   -1.1106   -2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7748    0.0313   -0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098   -0.5533   -1.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491    0.0437   -1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1991   -0.6041   -1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528   -0.0249   -1.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6868    1.2097   -1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9416    1.7899   -1.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0998    3.0253   -0.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9994    3.6036    0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1326    4.7323    0.5572 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    3.0533    0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432    1.8666   -0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734    1.2792   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9000    4.4067    3.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1504    4.0418    3.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    2.9058    4.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1292    0.9785    0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7714    2.3711   -0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    1.6873   -0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5931    0.6451   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    0.1922    1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208   -2.5616    1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4894   -2.8214    0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850   -3.8288    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4959   -1.3621   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7121   -0.3096   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1214   -1.9750   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5711   -1.5385    2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5726   -3.0934    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -1.3043    2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -3.0789    2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0462   -2.8732   -0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8137   -2.3880    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908   -2.8128   -1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967   -3.9674    0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205   -0.2261   -2.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002   -2.0405   -2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720   -1.2936   -2.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0360    0.2281    0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5552    1.0000   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -1.5725   -2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2896   -0.5411   -2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7774    1.2821   -1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0598    3.5298   -0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5468    1.8013    0.0237 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  1  0
  6  7  1  0
  7  8  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  2  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
 16  7  1  0
 30 20  1  0
 29 23  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  1
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  6
 15 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 21 58  1  0
 22 59  1  0
 24 60  1  0
 25 61  1  0
 30 62  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 11 44  1  0
M  END


  Mrv1652309082200572D          

 30 32  0  0  1  0            999 V2000
    3.1381   -4.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   -3.9894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670   -4.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670   -5.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -3.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960   -4.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7104   -3.9894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7104   -3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960   -2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960   -1.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249   -2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1394   -3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1394   -3.9894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8539   -4.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249   -4.4019    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8122   -5.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0376   -5.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4748   -5.8300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2993   -5.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6866   -5.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5111   -5.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9483   -5.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7728   -5.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2100   -6.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8226   -7.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2598   -7.8426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9982   -7.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5610   -6.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7365   -6.5009    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  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  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  6  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 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
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  2  0  0  0  0
 20 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC[C@H]1C(CC[C@H](C)[C@]1(C)COC1=CC=C2C=CC(=O)OC2=C1)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O5/c1-16(2)20-10-6-17(3)25(4,21(20)11-13-23(26)28-5)15-29-19-9-7-18-8-12-24(27)30-22(18)14-19/h7-9,12,14,17,21H,6,10-11,13,15H2,1-5H3/t17-,21-,25-/m0/s1

> <INCHI_KEY>
LWKZASDDSMSRFV-ADSMNUKGSA-N

> <FORMULA>
C25H32O5

> <MOLECULAR_WEIGHT>
412.526

> <EXACT_MASS>
412.22497413

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.385232181525254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-[(1S,2S,3S)-2,3-dimethyl-2-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate

> <JCHEM_LOGP>
4.976169833333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.846058591927234

> <JCHEM_POLAR_SURFACE_AREA>
61.83

> <JCHEM_REFRACTIVITY>
117.17019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[(1S,2S,3S)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       5.858  -8.217   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.191  -7.447   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.525  -8.217   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.525  -9.757   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.859  -7.447   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.192  -8.217   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.526  -7.447   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.526  -5.907   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.192  -5.137   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.192  -3.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.859  -5.907   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.860  -5.137   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.194  -5.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.194  -7.447   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.527  -8.217   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.860  -8.217   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.583  -9.577   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.137  -9.577   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.953 -10.883   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      15.492 -10.829   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.215  -9.469   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.754  -9.415   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.570 -10.721   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.109 -10.668   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.925 -11.974   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.202 -13.333   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.018 -14.639   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      18.663 -13.387   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.847 -12.081   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.308 -12.135   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                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29   20                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl galbanic acid	Generator

Chemical Formula

C₂₅H₃₂O₅

Average Mass

412.5260 Da

Monoisotopic Mass

412.22497 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)CC[C@H]1C(CC[C@H](C)[C@]1(C)COC1=CC=C2C=CC(=O)OC2=C1)=C(C)C

InChI Identifier

InChI=1S/C25H32O5/c1-16(2)20-10-6-17(3)25(4,21(20)11-13-23(26)28-5)15-29-19-9-7-18-8-12-24(27)30-22(18)14-19/h7-9,12,14,17,21H,6,10-11,13,15H2,1-5H3/t17-,21-,25-/m0/s1

InChI Key

LWKZASDDSMSRFV-ADSMNUKGSA-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
Ferula assa-foetida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Coumarin
Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
P-menthane monoterpenoid
1-benzopyran
Monoterpenoid
Alkyl aryl ether
Pyranone
Fatty acid ester
Fatty acyl
Benzenoid
Pyran
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Lactone
Ether
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034601

Chemspider ID

5428912

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7075765

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ebadi A, Olyaie SS, Dastan D: To be ionized or not to be ionized: the vital role of physicochemical properties of galbanic acid derivatives in AChE assay. J Biomol Struct Dyn. 2021 Jun;39(9):3235-3243. doi: 10.1080/07391102.2020.1764391. Epub 2020 May 15. [PubMed:32364046 ]
Dastan D, Salehi P, Aliahmadi A, Gohari AR, Maroofi H, Ardalan A: New coumarin derivatives from Ferula pseudalliacea with antibacterial activity. Nat Prod Res. 2016 Dec;30(24):2747-2753. doi: 10.1080/14786419.2016.1149705. Epub 2016 Mar 8. [PubMed:26953526 ]
Dastan D, Salehi P, Reza Gohari A, Zimmermann S, Kaiser M, Hamburger M, Reza Khavasi H, Ebrahimi SN: Disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea, and determination of their absolute configurations. Phytochemistry. 2012 Jun;78:170-8. doi: 10.1016/j.phytochem.2012.02.016. Epub 2012 Mar 20. [PubMed:22440297 ]
Iranshahi M, Arfa P, Ramezani M, Jaafari MR, Sadeghian H, Bassarello C, Piacente S, Pizza C: Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial activity of 7-prenyloxycoumarins against promastigotes. Phytochemistry. 2007 Feb;68(4):554-61. doi: 10.1016/j.phytochem.2006.11.002. Epub 2006 Dec 29. [PubMed:17196626 ]
Zamani Taghizadeh Rabe S, Iranshahi M, Mahmoudi M: In vitro anti-inflammatory and immunomodulatory properties of umbelliprenin and methyl galbanate. J Immunotoxicol. 2016;13(2):209-16. doi: 10.3109/1547691X.2015.1043606. Epub 2015 May 25. [PubMed:26004404 ]
Kasaian J, Iranshahy M, Iranshahi M: Synthesis, biosynthesis and biological activities of galbanic acid - A review. Pharm Biol. 2013 Dec 13. doi: 10.3109/13880209.2013.846916. [PubMed:24328450 ]
Kohno S, Murata T, Sugiura A, Ito C, Iranshahi M, Hikita K, Kaneda N: Methyl galbanate, a novel inhibitor of nitric oxide production in mouse macrophage RAW264.7 cells. J Nat Med. 2011 Apr;65(2):353-9. doi: 10.1007/s11418-010-0505-7. Epub 2011 Jan 19. [PubMed:21246298 ]
LOTUS database [Link]

Showing NP-Card for methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate (NP0257742)

MOL for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

3D MOL for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

3D SDF for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

3D-SDF for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

PDB for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

3D PDB for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

SMILES for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

INCHI for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

Structure for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)

3D Structure for NP0257742 (methyl 3-[(1s,2s,3s)-2,3-dimethyl-2-{[(2-oxochromen-7-yl)oxy]methyl}-6-(propan-2-ylidene)cyclohexyl]propanoate)