NP-MRD: Showing NP-Card for methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate (NP0312323)

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Record Information

Version

2.0

Created at

2022-09-11 09:01:35 UTC

Updated at

2022-09-11 09:01:35 UTC

NP-MRD ID

NP0312323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate

Description

Dapholdhamine D belongs to the class of organic compounds known as cycloheptapyrans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a pyran. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate is found in Daphniphyllum oldhamii. Based on a literature review very few articles have been published on Dapholdhamine D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112211012D          

 33 38  0  0  1  0            999 V2000
    4.9186   -2.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8025   -1.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224   -0.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5807   -1.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4938    0.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204    0.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7864    1.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4262    2.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5829    2.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2972    1.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    0.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555    0.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0517   -0.3322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075    1.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9485    1.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7701    2.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9422    3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087    2.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    3.8135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3597    2.3017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    3.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    2.7917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4766    3.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689    2.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    1.9480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4943    1.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524    1.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    0.8828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0315    0.4449    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 26 29  1  0  0  0  0
 12 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  6  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 62 67  0  0  0  0  0  0  0  0999 V2000
    5.0888    3.5296    1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2783    2.3768    1.0416 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5863    2.0208   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851    2.7235   -1.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322    0.8402   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1691   -0.3795   -0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3687   -0.9441   -0.9144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032   -2.2851   -1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371   -3.0543   -1.1322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1775   -2.6090   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0257   -1.2706   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -0.5502    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3923    0.7652    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597    1.9686    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    2.8976    1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230    2.1192    0.2654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2183    3.3569    0.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4477    1.0502    1.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -0.2711    0.5295 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5493   -1.0125    1.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967   -0.3927    1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9448   -0.9475    2.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2847    0.5364    0.7766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2493   -0.1848   -0.7429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432   -1.2942   -1.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273   -2.1273   -0.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0608   -2.9467   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -3.6474   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3822   -1.1536    0.3204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1523   -1.9517    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006    1.0282   -1.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    1.9488   -1.1958 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4364    3.3134   -1.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1577    3.9898    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0781    3.2561    1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6532    4.2722    1.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2032   -0.2753   -0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3660   -2.6942   -1.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1152    3.3554    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8159    1.0019    2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4010    1.4427    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6911   -2.0493    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1690   -0.8861    2.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3635   -1.1431    3.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6991   -0.2067    2.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3118   -1.9227    2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7525   -1.8509   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364   -0.9743   -2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6514   -2.8562   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -3.7214   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855   -2.3461   -2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4199   -4.4514   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7797   -4.0122    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9258   -2.2176    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2518   -1.2809    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7258   -2.8683    1.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    0.7665   -2.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1340    1.6449   -1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446    1.6358   -1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3553    3.6323   -1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    3.2522   -2.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6381    4.0540   -1.5847 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  1
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  1
 24 31  1  0
 31 32  1  0
 32 33  1  0
 13  5  1  0
 32 16  1  0
 11  6  1  0
 29 12  1  0
 28 10  1  0
 29 19  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  7 37  1  0
  8 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  1
 27 50  1  0
 27 51  1  0
 28 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 31 57  1  0
 31 58  1  0
 32 59  1  6
 33 60  1  0
 33 61  1  0
 33 62  1  0
M  END


  Mrv1652309112211012D          

 33 38  0  0  1  0            999 V2000
    4.9186   -2.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8025   -1.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224   -0.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5807   -1.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4938    0.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204    0.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7864    1.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4262    2.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5829    2.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2972    1.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    0.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555    0.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0517   -0.3322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075    1.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9485    1.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7701    2.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9422    3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087    2.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    3.8135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3597    2.3017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    3.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    2.7917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4766    3.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689    2.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    1.9480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4943    1.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524    1.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    0.8828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0315    0.4449    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 26 29  1  0  0  0  0
 12 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  6  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0312323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2C=COC3=C2C2=C1C(=O)[C@]1(O)CC4(CC(C)=O)N(C[C@@H](CC3)[C@@]24C)C[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C26H29NO6/c1-13-10-27-11-15-5-6-17-18-16(7-8-33-17)19(23(30)32-4)20-21(18)24(15,3)25(27,9-14(2)28)12-26(13,31)22(20)29/h7-8,13,15,31H,5-6,9-12H2,1-4H3/t13-,15-,24+,25?,26+/m1/s1

> <INCHI_KEY>
FEMMUEBHMHVLHN-MYYMWEGXSA-N

> <FORMULA>
C26H29NO6

> <MOLECULAR_WEIGHT>
451.519

> <EXACT_MASS>
451.199487658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.53118969784239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,5S,6R,10S)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1^{5,19}.0^{2,10}.0^{3,8}.0^{17,20}]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate

> <JCHEM_LOGP>
2.0973699923333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.737331325661984

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.631858431560207

> <JCHEM_PKA_STRONGEST_BASIC>
7.945592802992599

> <JCHEM_POLAR_SURFACE_AREA>
97.05

> <JCHEM_REFRACTIVITY>
121.14389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,5S,6R,10S)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1^{5,19}.0^{2,10}.0^{3,8}.0^{17,20}]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       9.181  -4.045   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.965  -2.466   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.695  -1.436   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.684  -2.678   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.294   0.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.388   1.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.931   1.101   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.801   2.377   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.129   3.791   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.555   4.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.700   2.698   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.155   2.474   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.891   0.882   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.397   0.188   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.242  -1.400   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.800   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.963  -0.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.187   1.898   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.637   3.341   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.304   4.876   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.759   5.744   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.576   4.669   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.882   7.119   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       2.538   4.296   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.545   5.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.128   5.211   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.490   6.033   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.969   5.519   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.096   3.636   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.523   3.568   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.218   3.306   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.335   1.648   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.059   0.830   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   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13   29                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   32                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   24   29                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   10                                                       
CONECT   29   26   12   19   30                                             
CONECT   30   29                                                            
CONECT   31   24   32                                                       
CONECT   32   31   16   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₉NO₆

Average Mass

451.5190 Da

Monoisotopic Mass

451.19949 Da

IUPAC Name

methyl (2S,5S,6R,10S)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1^{5,19}.0^{2,10}.0^{3,8}.0^{17,20}]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate

Traditional Name

methyl (2S,5S,6R,10S)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1^{5,19}.0^{2,10}.0^{3,8}.0^{17,20}]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2C=COC3=C2C2=C1C(=O)[C@]1(O)CC4(CC(C)=O)N(C[C@@H](CC3)[C@@]24C)C[C@H]1C

InChI Identifier

InChI=1S/C26H29NO6/c1-13-10-27-11-15-5-6-17-18-16(7-8-33-17)19(23(30)32-4)20-21(18)24(15,3)25(27,9-14(2)28)12-26(13,31)22(20)29/h7-8,13,15,31H,5-6,9-12H2,1-4H3/t13-,15-,24+,25?,26+/m1/s1

InChI Key

FEMMUEBHMHVLHN-MYYMWEGXSA-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
Daphniphyllum oldhamii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloheptapyrans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a pyran. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Cycloheptapyrans

Sub Class

Not Available

Direct Parent

Cycloheptapyrans

Alternative Parents

Substituents

Cycloheptapyran
Indolizidine
Aryl ketone
Aryl alkyl ketone
Aralkylamine
Beta-aminoketone
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Tertiary alcohol
Methyl ester
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Ketone
Azacycle
Oxacycle
Carboxylic acid derivative
Amine
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
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
logP	2.1	ChemAxon
pKa (Strongest Acidic)	12.63	ChemAxon
pKa (Strongest Basic)	7.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.14 m³·mol⁻¹	ChemAxon
Polarizability	47.53 Å³	ChemAxon
Number of Rings	6	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

C00047841

Chemspider ID

24628973

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45273379

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate (NP0312323)

MOL for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

3D MOL for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

3D SDF for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

3D-SDF for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

PDB for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

3D PDB for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

SMILES for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

INCHI for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

Structure for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)

3D Structure for NP0312323 (methyl (2s,5s,6r,10s)-5-hydroxy-2,6-dimethyl-21-oxo-3-(2-oxopropyl)-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate)