NP-MRD: Showing NP-Card for methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate (NP0290933)

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Record Information

Version

1.0

Created at

2022-09-09 21:50:19 UTC

Updated at

2022-09-09 21:50:20 UTC

NP-MRD ID

NP0290933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate

Description

Methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]Tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate is found in Pseudolarix amabilis. It was first documented in 2022 (PMID: 36115695). Based on a literature review a significant number of articles have been published on methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]Tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate (PMID: 36115691) (PMID: 36115690) (PMID: 36115694) (PMID: 36115693) (PMID: 36115692) (PMID: 36115689).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223502D          

 30 32  0  0  1  0            999 V2000
   -1.3037    5.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832    4.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9872    4.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117    4.5037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668    3.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6708    2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2253    2.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498    2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384    1.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    0.6842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7471    0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -0.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2573   -1.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6217   -0.4022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3742   -0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    0.4461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1207    0.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605    1.1095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7387    1.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9140    1.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    0.3970    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6774   -0.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2142   -0.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1307   -1.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4984   -1.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7397    1.2283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5517    1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9443    0.3572    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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 15 30  1  6  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    8.1347   -0.5624   -1.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1346   -0.6870   -0.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8520   -0.1739   -0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6972    0.3341   -1.5795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8475   -0.2951    0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0933   -0.9468    1.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6010    0.1768    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6277    0.0637    1.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.3952    1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453    0.8572    1.1099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3483    1.7446    2.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769    1.6039   -0.0946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093    0.9680   -1.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    1.3676   -2.3584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876   -0.1496   -1.1877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2477    0.0590   -2.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650    0.8733   -2.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746    1.8268   -1.5197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1021    3.1045   -1.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527    2.1360   -1.9798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0948    1.1872   -0.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8907    0.8422    0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137   -0.2414    0.1527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5573   -1.4980    0.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671   -2.2947   -0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715   -3.6263    0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9895   -1.8871   -1.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7595   -0.3517    0.9789 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0040   -1.4463    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5811   -1.4189   -1.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0512   -0.1689   -0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3632   -1.5334   -1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8466    0.1779   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -1.8939    1.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9377   -0.3220    2.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1494   -1.3735    1.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4659    0.6145   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0348   -0.4276    2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.0845    2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    2.7585    1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    1.3254    2.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    1.8656    3.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9819   -0.5641   -3.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334    0.8352   -3.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5542    3.2591   -2.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4349    3.2226   -0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952    4.0007   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4334    1.4538   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5908    2.0371    0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8992    0.4552   -0.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948    0.5103    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3731    1.8016    0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475   -3.6035    1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345   -4.3647    0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8036   -3.9355   -0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9485   -0.7263    2.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383   -2.4066    0.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562   -1.2116    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -1.3290   -2.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721   -2.3332   -1.4191 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
 10  9  1  1
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 15 13  1  1
 15 30  1  0
 30 29  1  0
 29 28  1  0
 28 23  1  0
 23 22  1  0
 22 21  1  0
 21 18  1  0
 18 19  1  0
 18 20  1  6
 18 17  1  0
 17 16  2  0
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 25 26  1  0
 25 27  2  0
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 23 15  1  0
 16 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 11 40  1  0
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 11 42  1  0
 30 59  1  0
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 29 57  1  0
 29 58  1  0
 28 56  1  1
 22 51  1  0
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 21 49  1  0
 21 50  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 17 44  1  0
 16 43  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
M  END


  Mrv1652309092223502D          

 30 32  0  0  1  0            999 V2000
   -1.3037    5.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832    4.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9872    4.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117    4.5037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668    3.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6708    2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2253    2.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498    2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384    1.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    0.6842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7471    0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -0.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2573   -1.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6217   -0.4022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3742   -0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    0.4461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1207    0.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605    1.1095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9140    1.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    0.3970    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.1307   -1.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4984   -1.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7397    1.2283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5517    1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9443    0.3572    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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 15 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0290933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(\C)=C\C=C\[C@@]1(C)OC(=O)[C@@]23CC[C@@H]1[C@]2(CC[C@](C)(O)C=C3)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-15(18(25)28-5)7-6-9-21(4)17-8-10-22(19(26)30-21)13-11-20(3,27)12-14-23(17,22)29-16(2)24/h6-7,9,11,13,17,27H,8,10,12,14H2,1-5H3/b9-6+,15-7+/t17-,20+,21+,22-,23-/m0/s1

> <INCHI_KEY>
WYIMJLOGLKUJNQ-LSHKRLLPSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.62830866613038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0^{1,7}]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate

> <JCHEM_LOGP>
2.5623184699999983

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.681955176701017

> <JCHEM_PKA_STRONGEST_BASIC>
-2.937912805710975

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
111.28599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0^{1,7}]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.433  10.013   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.395   8.473   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.710   7.670   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.062   8.407   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.671   6.131   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.986   5.328   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.287   5.377   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.960   3.797   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.632   2.822   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.223   1.277   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.395   1.126   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.296  -0.261   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.558  -0.946   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.347  -2.484   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.027  -0.751   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.432  -1.382   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.801  -0.677   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.104   0.833   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.692   0.314   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.206   2.071   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.112   2.011   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.573   1.970   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.645   0.741   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.264  -0.165   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.400  -1.820   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.244  -3.479   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.930  -2.847   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.381   2.293   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.897   2.021   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.629   0.667   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   28                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23   30                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   24   28                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   10   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   15                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0,]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoic acid	Generator

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0^{1,7}]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate

Traditional Name

methyl (2E,4E)-5-[(1R,4S,7S,8S,9R)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0^{1,7}]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(\C)=C\C=C\[C@@]1(C)OC(=O)[C@@]23CC[C@@H]1[C@]2(CC[C@](C)(O)C=C3)OC(C)=O

InChI Identifier

InChI=1S/C23H30O7/c1-15(18(25)28-5)7-6-9-21(4)17-8-10-22(19(26)30-21)13-11-20(3,27)12-14-23(17,22)29-16(2)24/h6-7,9,11,13,17,27H,8,10,12,14H2,1-5H3/b9-6+,15-7+/t17-,20+,21+,22-,23-/m0/s1

InChI Key

WYIMJLOGLKUJNQ-LSHKRLLPSA-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
Pseudolarix amabilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Prenyldaucane diterpenoid
Tricarboxylic acid or derivatives
Caprolactone
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Fatty acyl
Oxane
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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
logP	2.56	ChemAxon
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111.29 m³·mol⁻¹	ChemAxon
Polarizability	44.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163189488

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hosokawa K, Nakao S: Somatic mutations and clonal expansions in paroxysmal nocturnal hemoglobinuria. Semin Hematol. 2022 Jul;59(3):143-149. doi: 10.1053/j.seminhematol.2022.08.004. Epub 2022 Aug 22. [PubMed:36115691 ]
Durrani J, Groarke EM: Clonality in immune aplastic anemia: Mechanisms of immune escape or malignant transformation. Semin Hematol. 2022 Jul;59(3):137-142. doi: 10.1053/j.seminhematol.2022.08.001. Epub 2022 Aug 12. [PubMed:36115690 ]
eBioMedicine: The dynamics of the immune system and gut in the pathophysiology of multiple sclerosis. EBioMedicine. 2022 Sep;83:104273. doi: 10.1016/j.ebiom.2022.104273. [PubMed:36115695 ]
Lundgren S, Keranen M, Wartiovaara-Kautto U, Myllymaki M: Somatic compensation of inherited bone marrow failure. Semin Hematol. 2022 Jul;59(3):167-173. doi: 10.1053/j.seminhematol.2022.07.002. Epub 2022 Aug 3. [PubMed:36115694 ]
Alcedo PE, Gutierrez-Rodrigues F, Patel BA: Somatic mutations in VEXAS Syndrome and Erdheim-Chester disease: Inflammatory myeloid diseases. Semin Hematol. 2022 Jul;59(3):156-166. doi: 10.1053/j.seminhematol.2022.07.003. Epub 2022 Aug 3. [PubMed:36115693 ]
Todisco G, Moura PL, Hellstrom-Lindberg E: Clinical manifestations of clonal hematopoiesis: What has SF3B1-mutant MDS taught us? Semin Hematol. 2022 Jul;59(3):150-155. doi: 10.1053/j.seminhematol.2022.08.002. Epub 2022 Aug 11. [PubMed:36115692 ]
Kawakami T, Nakazawa H, Ishida F: Somatic mutations in acquired pure red cell aplasia. Semin Hematol. 2022 Jul;59(3):131-136. doi: 10.1053/j.seminhematol.2022.07.001. Epub 2022 Jul 16. [PubMed:36115689 ]
Savola P, Bhattacharya D, Huuhtanen J: The spectrum of somatic mutations in large granular lymphocyte leukemia, rheumatoid arthritis, and Felty's syndrome. Semin Hematol. 2022 Jul;59(3):123-130. doi: 10.1053/j.seminhematol.2022.07.004. Epub 2022 Aug 3. [PubMed:36115688 ]
Mustjoki S: Somatic mutations in "benign" blood diseases. Semin Hematol. 2022 Jul;59(3):121-122. doi: 10.1053/j.seminhematol.2022.08.003. [PubMed:36115687 ]
Campbell JW: Dysplasias in the Child's Spine. Neurosurg Clin N Am. 2022 Jan;33(1S):e1-e10. doi: 10.1016/j.nec.2022.02.001. Epub 2022 Aug 6. [PubMed:36115686 ]
LOTUS database [Link]

Showing NP-Card for methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate (NP0290933)

MOL for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

3D MOL for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

3D SDF for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

3D-SDF for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

PDB for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

3D PDB for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

SMILES for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

INCHI for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

Structure for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)

3D Structure for NP0290933 (methyl (2e,4e)-5-[(1r,4s,7s,8s,9r)-7-(acetyloxy)-4-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-2-en-9-yl]-2-methylpenta-2,4-dienoate)