NP-MRD: Showing NP-Card for ajubractin e (NP0295761)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 04:56:22 UTC

Updated at

2022-09-10 04:56:22 UTC

NP-MRD ID

NP0295761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajubractin e

Description

Ajubractin E belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Ajubractin E 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. ajubractin e is found in Ajuga bracteosa. ajubractin e was first documented in 2011 (PMID: 21539300). Based on a literature review very few articles have been published on ajubractin E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102206562D          

 32 36  0  0  1  0            999 V2000
    1.2753    1.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0308    1.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6955    2.0457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1217    0.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8773    0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -0.4142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2186    0.3718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6632    0.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9137    1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8228    2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197    1.9439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0246    0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -0.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3861    0.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -0.8481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3631   -1.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472   -0.9583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5386   -1.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3503   -1.5367    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0938   -1.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6636   -1.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2721   -0.5713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4605   -0.7191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7170   -0.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -1.0242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2731   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9116   -1.3764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1057   -1.5525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -0.5903    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3761   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861    0.2157    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  1  0  0  0
 15 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 32  1  1  0  0  0
M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
   -2.8702    3.5508   -2.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557    2.7565   -1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7777    3.1652   -0.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2134    1.6463   -0.7534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068    0.9083    0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -0.2761    0.4855 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6849   -1.1926   -0.6362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0835   -1.2297   -0.8382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -2.3335   -0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3305   -2.1785   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3628   -3.4744   -0.8038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875   -0.7358   -1.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130   -0.7619   -1.5878 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1956   -0.7934   -2.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823    0.2788   -0.6007 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6889    1.6706   -1.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    0.1551   -0.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4165    0.2997   -1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930   -0.5772   -0.3580 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7164    0.1880    0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3717    0.7362    1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646    0.3440    1.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412   -0.8348    0.9761 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5136   -1.0285    0.5975 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0610   -0.0084    0.6563 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4340    0.8073    1.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309    0.8626    2.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770   -0.0610    2.9557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7724   -0.8367    4.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544   -0.9997    1.7979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8545   -2.3791    1.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605   -1.6496    1.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8596    3.8588   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    4.4692   -2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790    3.0228   -3.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    1.6040    1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796    0.5474    0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2609   -2.1930   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8256   -3.1673   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7686   -1.4140   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5857   -1.8757   -2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3347    0.1955   -2.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389   -1.5636   -2.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -1.7664   -1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0008   -1.5823   -2.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475   -1.2038   -3.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.1756   -3.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1330    1.7081   -2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    2.0401   -1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769    2.3768   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4202    0.9610    0.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061   -0.0103   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8560    1.3310   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791   -1.4930   -0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8856    1.0002   -0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5738   -0.5192    0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5192    1.8208    1.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0093    0.2999    2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2609   -1.7204    1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767   -1.0573    0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6888    1.8755    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090    0.4339    2.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142    0.6524    3.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777    1.9259    3.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6327    0.5400    2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -1.3397    4.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -3.2145    1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9025   -2.7371    3.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7  6  1  0
  6  5  1  6
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 25 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 15 13  1  0
 24 17  1  0
 30  6  1  0
 30 32  1  6
 23 19  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 13 44  1  1
 12 42  1  0
 12 43  1  0
  7 38  1  1
 10 39  1  0
 10 40  1  0
 10 41  1  0
  5 36  1  0
  5 37  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 25 60  1  1
 26 61  1  0
 26 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  6
 29 66  1  0
 31 67  1  0
 31 68  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 18 53  1  0
 19 54  1  6
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  1
M  END


  Mrv1652309102206562D          

 32 36  0  0  1  0            999 V2000
    1.2753    1.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0308    1.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6955    2.0457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1217    0.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8773    0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -0.4142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2186    0.3718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6632    0.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9137    1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8228    2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197    1.9439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0246    0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -0.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3861    0.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -0.8481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3631   -1.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472   -0.9583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5386   -1.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3503   -1.5367    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0938   -1.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6636   -1.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2721   -0.5713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4605   -0.7191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7170   -0.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -1.0242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2731   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9116   -1.3764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1057   -1.5525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -0.5903    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3761   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861    0.2157    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  1  0  0  0
 15 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0295761

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](OC(C)=O)[C@]2(COC(C)=O)[C@H](CC[C@H](O)[C@]22CO2)[C@@]1(C)[C@@H]1C[C@H]2CCO[C@H]2O1

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O8/c1-13-9-20(31-15(3)26)23(11-29-14(2)25)17(5-6-18(27)24(23)12-30-24)22(13,4)19-10-16-7-8-28-21(16)32-19/h13,16-21,27H,5-12H2,1-4H3/t13-,16-,17-,18+,19+,20+,21+,22+,23+,24-/m1/s1

> <INCHI_KEY>
YGOONLMJIAXMBW-PVSOBBEXSA-N

> <FORMULA>
C24H36O8

> <MOLECULAR_WEIGHT>
452.544

> <EXACT_MASS>
452.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.83172260100139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,2S,4aR,5S,6R,8S,8aR)-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-8-(acetyloxy)-2-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

> <JCHEM_LOGP>
1.1852298956666654

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.89559130661624

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2818683624860565

> <JCHEM_POLAR_SURFACE_AREA>
103.82000000000001

> <JCHEM_REFRACTIVITY>
111.60580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aR,5S,6R,8S,8aR)-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-8-(acetyloxy)-2-hydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.381   3.525   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.791   2.906   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.032   3.819   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.961   1.376   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.371   0.757   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.541  -0.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.008   0.694   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.971   1.833   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.439   3.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.269   4.831   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.943   3.629   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.513   1.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.550  -0.116   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.054   0.213   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.082  -1.583   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.144  -3.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.608  -1.789   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.339  -3.145   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.854  -2.869   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.242  -3.536   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.305  -2.422   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.575  -1.066   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.060  -1.342   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.672  -0.675   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.577  -1.912   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.110  -3.379   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.605  -3.708   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.568  -2.569   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.064  -2.898   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.036  -1.102   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.569  -0.634   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.707   0.403   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25   30                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   25                                             
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23   17                                                       
CONECT   25   15    6   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    6   31   32                                             
CONECT   31   30   32                                                       
CONECT   32   31   30                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
3-Epi-14,15-dihydrocaryoptinol	ChEBI
3beta-Hydroxy-14,15-dihydroclerodin	ChEBI
3b-Hydroxy-14,15-dihydroclerodin	Generator
3Β-hydroxy-14,15-dihydroclerodin	Generator

Chemical Formula

C₂₄H₃₆O₈

Average Mass

452.5440 Da

Monoisotopic Mass

452.24102 Da

IUPAC Name

[(1R,2S,4aR,5S,6R,8S,8aR)-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-8-(acetyloxy)-2-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

Traditional Name

(1R,2S,4aR,5S,6R,8S,8aR)-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-8-(acetyloxy)-2-hydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](OC(C)=O)[C@]2(COC(C)=O)[C@H](CC[C@H](O)[C@]22CO2)[C@@]1(C)[C@@H]1C[C@H]2CCO[C@H]2O1

InChI Identifier

InChI=1S/C24H36O8/c1-13-9-20(31-15(3)26)23(11-29-14(2)25)17(5-6-18(27)24(23)12-30-24)22(13,4)19-10-16-7-8-28-21(16)32-19/h13,16-21,27H,5-12H2,1-4H3/t13-,16-,17-,18+,19+,20+,21+,22+,23+,24-/m1/s1

InChI Key

YGOONLMJIAXMBW-PVSOBBEXSA-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
Ajuga bracteosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Dicarboxylic acid or derivatives
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:67468 )
acetate ester (CHEBI:67468 )
diterpenoid (CHEBI:67468 )
oxaspiro compound (CHEBI:67468 )
furofuran (CHEBI:67468 )

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	1.19	ChemAxon
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111.61 m³·mol⁻¹	ChemAxon
Polarizability	47.83 Å³	ChemAxon
Number of Rings	5	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

34999274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53355682

PDB ID

Not Available

ChEBI ID

67468

Good Scents ID

Not Available

References

General References

Castro A, Coll J, Arfan M: neo-Clerodane diterpenoids from Ajuga bracteosa. J Nat Prod. 2011 May 27;74(5):1036-41. doi: 10.1021/np100929u. Epub 2011 May 3. [PubMed:21539300 ]
LOTUS database [Link]

Showing NP-Card for ajubractin e (NP0295761)

MOL for NP0295761 (ajubractin e)

3D MOL for NP0295761 (ajubractin e)

3D SDF for NP0295761 (ajubractin e)

3D-SDF for NP0295761 (ajubractin e)

PDB for NP0295761 (ajubractin e)

3D PDB for NP0295761 (ajubractin e)

SMILES for NP0295761 (ajubractin e)

INCHI for NP0295761 (ajubractin e)

Structure for NP0295761 (ajubractin e)

3D Structure for NP0295761 (ajubractin e)