NP-MRD: Showing NP-Card for (3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione (NP0231905)

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Record Information

Version

2.0

Created at

2022-09-06 12:57:05 UTC

Updated at

2022-09-06 12:57:05 UTC

NP-MRD ID

NP0231905

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione

Description

Equisetin belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Equisetin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione is found in Ferula equisetacea, Fusarium equiseti and Fusarium heterosporum. (3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione was first documented in 2021 (PMID: 34869220). Based on a literature review a small amount of articles have been published on equisetin (PMID: 35722281) (PMID: 35646525) (PMID: 35209839).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062214572D          

 27 29  0  0  1  0            999 V2000
   -1.4289   -1.6500    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018   -3.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321   -2.5036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5014   -3.9361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2663   -4.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9164   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017   -4.3733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442   -5.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698   -3.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693   -4.0426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -0.6813    3.8911    2.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098    3.3809    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344    2.3628    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    1.8420   -0.8272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7201    2.1135   -1.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363    1.2267   -1.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5944   -0.0988   -1.3776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8608   -0.4487   -0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8065   -1.9510   -0.3943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2766   -2.3699    0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5181   -2.5827   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874   -1.8268   -0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4970   -0.3269   -0.4351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1624    0.3968   -0.7837 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1861   -0.2150   -2.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093    0.0520    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0205   -0.3385    1.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9191    0.0804    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8033    0.4472   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5164    1.1353   -1.6364 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1486   -0.1678   -0.3677 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2539   -1.5677   -0.8861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301   -2.1332   -0.4477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595   -0.1247    1.0983 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3641    0.0489    1.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078   -0.2830    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4467   -0.6566    2.6842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    4.8939    2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2022    4.0883    3.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328    3.2582    2.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    3.8727    0.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422    1.9167    1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297    2.5094   -1.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351    3.1029   -2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4815    1.4553   -2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -0.8335   -2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675   -0.1064   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7739    0.0257    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5909   -2.3544   -1.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9052   -3.2847    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4339   -2.5720    1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9071   -1.5645    1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -2.8334   -1.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4720   -3.5850   -0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0508   -2.1591    0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483   -2.1458   -0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731    0.0017    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951    0.5223   -2.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916   -0.9804   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551   -0.8515   -2.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109    0.3904    2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178    0.4525   -0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091   -2.1833   -0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1586   -1.5785   -1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1905   -1.5015   -0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1697    0.2794    2.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9382   -0.9198    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0521    0.7984    1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 14  4  1  0
 26 18  1  0
 13  7  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  6
  5 34  1  0
  6 35  1  0
  7 36  1  6
  8 37  1  0
  8 38  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  1
 15 48  1  0
 15 49  1  0
 15 50  1  0
 17 51  1  0
 21 52  1  6
 22 53  1  0
 22 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 25 58  1  0
M  END


  Mrv1652309062214572D          

 27 29  0  0  1  0            999 V2000
   -1.4289   -1.6500    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018   -3.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321   -2.5036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5014   -3.9361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2663   -4.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9164   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017   -4.3733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442   -5.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698   -3.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693   -4.0426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0231905

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\[C@@H]1C=C[C@@H]2C[C@H](C)CC[C@H]2[C@]1(C)C(\O)=C1/C(=O)[C@H](CO)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO4/c1-5-6-15-9-8-14-11-13(2)7-10-16(14)22(15,3)20(26)18-19(25)17(12-24)23(4)21(18)27/h5-6,8-9,13-17,24,26H,7,10-12H2,1-4H3/b6-5+,20-18-/t13-,14-,15-,16-,17+,22-/m1/s1

> <INCHI_KEY>
QNQBPPQLRODXET-HMHJLHGTSA-N

> <FORMULA>
C22H31NO4

> <MOLECULAR_WEIGHT>
373.493

> <EXACT_MASS>
373.225308482

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.7895272251924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z,5S)-3-{[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione

> <JCHEM_LOGP>
2.669593618333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.077288686250348

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.667383354902307

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7945695089261554

> <JCHEM_POLAR_SURFACE_AREA>
77.84

> <JCHEM_REFRACTIVITY>
108.23159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5S)-3-{[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.405  -4.493   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.297  -5.853   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.287  -4.673   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.669  -7.347   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.097  -7.924   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.311  -6.976   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       3.363  -8.163   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.256  -9.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.184  -7.174   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.689  -7.546   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    4   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   18   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
(-)-Equisetin	ChEBI
N-Methyltrichosetin	ChEBI

Chemical Formula

C₂₂H₃₁NO₄

Average Mass

373.4930 Da

Monoisotopic Mass

373.22531 Da

IUPAC Name

(3Z,5S)-3-{[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione

Traditional Name

(3Z,5S)-3-{[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

C\C=C\[C@@H]1C=C[C@@H]2C[C@H](C)CC[C@H]2[C@]1(C)C(\O)=C1/C(=O)[C@H](CO)N(C)C1=O

InChI Identifier

InChI=1S/C22H31NO4/c1-5-6-15-9-8-14-11-13(2)7-10-16(14)22(15,3)20(26)18-19(25)17(12-24)23(4)21(18)27/h5-6,8-9,13-17,24,26H,7,10-12H2,1-4H3/b6-5+,20-18-/t13-,14-,15-,16-,17+,22-/m1/s1

InChI Key

QNQBPPQLRODXET-HMHJLHGTSA-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 equisetacea	LOTUS Database	35616633
Fusarium equiseti	LOTUS Database	35616633
Fusarium heterosporum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-alkylpyrrolidines

Direct Parent

N-alkylpyrrolidines

Alternative Parents

Substituents

Pyrrolidone
2-pyrrolidone
3-pyrrolidone
N-alkylpyrrolidine
Tertiary carboxylic acid amide
Vinylogous acid
Carboxamide group
Ketone
Lactam
Cyclic ketone
Enol
Carboxylic acid derivative
Azacycle
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
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	2.67	ChemAxon
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-0.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.23 m³·mol⁻¹	ChemAxon
Polarizability	41.79 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024788

Chemspider ID

23078658

KEGG Compound ID

Not Available

BioCyc ID

CPD-17992

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54679016

PDB ID

Not Available

ChEBI ID

142135

Good Scents ID

Not Available

References

General References

Huang B, Peng S, Liu S, Zhang Y, Wei Y, Xu X, Gao C, Liu Y, Luo X: Isolation, Screening, and Active Metabolites Identification of Anti-Vibrio Fungal Strains Derived From the Beibu Gulf Coral. Front Microbiol. 2022 Jun 2;13:930981. doi: 10.3389/fmicb.2022.930981. eCollection 2022. [PubMed:35722281 ]
Xu Z, Liu D, Liu D, Ren X, Liu H, Qi G, Zhou Y, Wu C, Zhu K, Zou Z, Yuan J, Lin W, Guo P: Equisetin is an anti-obesity candidate through targeting 11beta-HSD1. Acta Pharm Sin B. 2022 May;12(5):2358-2373. doi: 10.1016/j.apsb.2022.01.006. Epub 2022 Jan 15. [PubMed:35646525 ]
Anteyi WO, Klaiber I, Rasche F: Diacetoxyscirpenol, a Fusarium exometabolite, prevents efficiently the incidence of the parasitic weed Striga hermonthica. BMC Plant Biol. 2022 Feb 24;22(1):84. doi: 10.1186/s12870-022-03471-6. [PubMed:35209839 ]
Ding L, Zhang SD, Haidar AK, Bajimaya M, Guo Y, Larsen TO, Gram L: Polycyclic Tetramate Macrolactams-A Group of Natural Bioactive Metallophores. Front Chem. 2021 Nov 12;9:772858. doi: 10.3389/fchem.2021.772858. eCollection 2021. [PubMed:34869220 ]
LOTUS database [Link]

Showing NP-Card for (3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione (NP0231905)

MOL for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

3D MOL for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

3D SDF for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

3D-SDF for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

PDB for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

3D PDB for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

SMILES for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

INCHI for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

Structure for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)

3D Structure for NP0231905 ((3z,5s)-3-{[(1s,2r,4as,6r,8ar)-1,6-dimethyl-2-[(1e)-prop-1-en-1-yl]-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl](hydroxy)methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione)