NP-MRD: Showing NP-Card for daphhimalenine B (NP0038713)

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Record Information

Version

2.0

Created at

2021-06-20 21:19:39 UTC

Updated at

2021-06-30 00:11:39 UTC

NP-MRD ID

NP0038713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

daphhimalenine B

Provided By

JEOL Database JEOL Logo

Description

Daphhimalenine B belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. daphhimalenine B is found in Daphniphyllum himalense and Daphniphyllum macropodum. daphhimalenine B was first documented in 2009 (PMID: 19904981). Based on a literature review very few articles have been published on Daphhimalenine B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123193D          

 57 62  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123193D          

 57 62  0  0  0  0            999 V2000
    2.2179    2.3752    2.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    1.0537    2.6083 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1716    2.3740    2.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3853   -1.3358    2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794   -2.7499    0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8293   -1.3819   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836    0.0608   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778   -1.6801   -0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3405    0.2367   -2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -0.8740   -2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524   -1.7159   -3.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -3.3123   -2.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175   -3.8945   -3.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078   -5.7613   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657   -5.6949   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -6.4623   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -7.4117   -2.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688   -6.8045   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -5.8962   -3.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007   -4.7491   -0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6770   -4.4384   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -2.1983   -3.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639    0.5216   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7721   -3.7749    1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2301    1.1079    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5038   -0.4396    2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    0.3529    3.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    1.2347    1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8838   -1.7751    2.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  8 28  1  0  0  0  0
 28 57  1  1  0  0  0
 28  5  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  1  0  0  0  0
  3  2  1  0  0  0  0
  7  6  1  1  0  0  0
  2  1  1  0  0  0  0
  8  9  2  0  0  0  0
 13 14  1  0  0  0  0
 11 12  1  0  0  0  0
  7 24  1  0  0  0  0
 21 12  1  0  0  0  0
 24 18  1  0  0  0  0
 14 24  1  0  0  0  0
  7  8  1  0  0  0  0
 18 19  1  0  0  0  0
 10 11  1  0  0  0  0
 19 20  2  0  0  0  0
  9 26  1  0  0  0  0
 18 16  1  0  0  0  0
 26 27  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 27 28  1  0  0  0  0
 16 17  1  0  0  0  0
 21 20  1  0  0  0  0
  9 10  1  0  0  0  0
 21 22  1  1  0  0  0
 12 13  1  0  0  0  0
 22 23  2  0  0  0  0
  7 21  1  0  0  0  0
 22 51  1  0  0  0  0
 12 39  1  6  0  0  0
 24 25  1  1  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
  5 32  1  1  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
 26 53  1  0  0  0  0
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 27 55  1  0  0  0  0
 27 56  1  0  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 18 48  1  1  0  0  0
 19 49  1  0  0  0  0
 20 50  1  0  0  0  0
 16 44  1  1  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 17 47  1  0  0  0  0
 25 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12N3C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])C([H])=C([H])[C@@]1(C([H])=O)[C@@]([H])(C3([H])[H])C([H])([H])C([H])([H])C3=C4[C@]([H])(C([H])([H])C3([H])[H])[C@]([H])(C(=O)OC([H])([H])[H])C([H])([H])[C@]214

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO4/c1-13-10-24-11-15-5-3-14-4-6-16-17(20(26)28-2)9-22(19(14)16)21(15,12-25)8-7-18(13)23(22,24)27/h7-8,12-13,15-18,27H,3-6,9-11H2,1-2H3/t13-,15-,16-,17-,18-,21-,22-,23-/m1/s1

> <INCHI_KEY>
HEGVMVZUHLZWNS-SNZIKGKMSA-N

> <FORMULA>
C23H29NO4

> <MOLECULAR_WEIGHT>
383.488

> <EXACT_MASS>
383.209658418

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.205282981855774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,3R,4R,10S,14S,15R,18R,19R)-18-formyl-19-hydroxy-14-methyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icosa-7(20),16-diene-3-carboxylate

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.5574393576666672

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.501728529612947

> <JCHEM_PKA_STRONGEST_BASIC>
9.718952121799958

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
105.91279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,3R,4R,10S,14S,15R,18R,19R)-18-formyl-19-hydroxy-14-methyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icosa-7(20),16-diene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
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    1.0672   -1.7988    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089   -2.0267   -0.4023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2198   -1.1964    0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3739   -0.7760   -0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456   -0.7638   -2.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -1.8323   -2.5554 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1997   -3.2703   -2.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0230   -3.8556   -1.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0101   -5.3306   -1.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5411   -5.7604   -1.2989 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2810   -6.5025   -2.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968   -4.4807   -1.0550 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9590   -3.8429   -2.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7063   -2.5814   -2.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786   -1.6505   -1.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1789   -0.2059   -2.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    0.1898   -3.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -3.5429   -0.3609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8340   -3.9552    1.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    0.1307    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    0.2964    2.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -0.9293    1.8224 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5044    3.0553    2.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964    2.7200    3.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    2.3740    2.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3853   -1.3358    2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794   -2.7499    0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8293   -1.3819   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836    0.0608   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3405    0.2367   -2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -0.8740   -2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524   -1.7159   -3.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -3.3123   -2.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175   -3.8945   -3.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078   -5.7613   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657   -5.6949   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -6.4623   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -7.4117   -2.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688   -6.8045   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -5.8962   -3.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007   -4.7491   -0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6770   -4.4384   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -2.1983   -3.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639    0.5216   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7721   -3.7749    1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2301    1.1079    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5038   -0.4396    2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    0.3529    3.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    1.2347    1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8838   -1.7751    2.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  8 28  1  0
 28 57  1  1
 28  5  1  0
  3  4  2  0
  5  6  1  0
  3  2  1  0
  7  6  1  1
  2  1  1  0
  8  9  2  0
 13 14  1  0
 11 12  1  0
  7 24  1  0
 21 12  1  0
 24 18  1  0
 14 24  1  0
  7  8  1  0
 18 19  1  0
 10 11  1  0
 19 20  2  0
  9 26  1  0
 18 16  1  0
 26 27  1  0
 16 15  1  0
 15 14  1  0
 27 28  1  0
 16 17  1  0
 21 20  1  0
  9 10  1  0
 21 22  1  1
 12 13  1  0
 22 23  2  0
  7 21  1  0
 22 51  1  0
 12 39  1  6
 24 25  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
  5 32  1  1
  6 33  1  0
  6 34  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 13 40  1  0
 13 41  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 18 48  1  1
 19 49  1  0
 20 50  1  0
 16 44  1  1
 15 42  1  0
 15 43  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 25 52  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       2.218   2.375   2.542  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.680   1.054   2.608  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.414   0.501   1.390  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.599   1.054   0.317  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.844  -0.891   1.570  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.067  -1.799   0.334  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.309  -2.027  -0.402  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.220  -1.196   0.466  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.427  -0.645   0.321  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.374  -0.776  -0.817  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.746  -0.764  -2.205  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.686  -1.832  -2.555  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.200  -3.270  -2.346  0.00  0.00           C+0
HETATM   14  N   UNK     0      -2.023  -3.856  -1.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.010  -5.331  -1.132  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.541  -5.760  -1.299  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.281  -6.503  -2.604  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.297  -4.481  -1.055  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.959  -3.843  -2.256  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.706  -2.581  -2.645  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.279  -1.651  -1.913  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.179  -0.206  -2.161  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.682   0.190  -3.213  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.727  -3.543  -0.361  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.834  -3.955   1.003  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.798   0.131   1.556  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.442   0.296   2.259  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.648  -0.929   1.822  0.00  0.00           C+0
HETATM   29  H   UNK     0       1.504   3.055   2.066  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.396   2.720   3.564  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.172   2.374   2.005  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.385  -1.336   2.416  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.479  -2.750   0.691  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.829  -1.382  -0.334  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.084   0.061  -0.779  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.978  -1.680  -0.677  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.341   0.237  -2.401  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.569  -0.874  -2.925  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.552  -1.716  -3.644  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.268  -3.312  -2.594  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.718  -3.894  -3.109  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.408  -5.761  -0.204  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.666  -5.695  -1.932  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.315  -6.462  -0.483  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.890  -7.412  -2.652  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.769  -6.805  -2.677  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.528  -5.896  -3.481  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.101  -4.749  -0.356  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.677  -4.438  -2.815  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.203  -2.198  -3.537  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.064   0.522  -1.371  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.772  -3.775   1.196  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.230   1.108   1.321  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.504  -0.440   2.169  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.550   0.353   3.346  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.983   1.235   1.926  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.884  -1.775   2.482  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    3   28    6   32                                             
CONECT    6    5    7   33   34                                             
CONECT    7    6   24    8   21                                             
CONECT    8   28    9    7                                                  
CONECT    9    8   26   10                                                  
CONECT   10   11    9   35   36                                             
CONECT   11   12   10   37   38                                             
CONECT   12   11   21   13   39                                             
CONECT   13   14   12   40   41                                             
CONECT   14   13   24   15                                                  
CONECT   15   16   14   42   43                                             
CONECT   16   18   15   17   44                                             
CONECT   17   16   45   46   47                                             
CONECT   18   24   19   16   48                                             
CONECT   19   18   20   49                                                  
CONECT   20   19   21   50                                                  
CONECT   21   12   20   22    7                                             
CONECT   22   21   23   51                                                  
CONECT   23   22                                                            
CONECT   24    7   18   14   25                                             
CONECT   25   24   52                                                       
CONECT   26    9   27   53   54                                             
CONECT   27   26   28   55   56                                             
CONECT   28    8   57    5   27                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   22                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   27                                                            
CONECT   57   28                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

RDKit          3D

57 62  0  0  0  0  0  0  0  0999 V2000
    2.2179    2.3752    2.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    1.0537    2.6083 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4142    0.5007    1.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5994    1.0543    0.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441   -0.8905    1.5704 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0672   -1.7988    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089   -2.0267   -0.4023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2198   -1.1964    0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269   -0.6448    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3739   -0.7760   -0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456   -0.7638   -2.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -1.8323   -2.5554 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1997   -3.2703   -2.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0230   -3.8556   -1.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0101   -5.3306   -1.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5411   -5.7604   -1.2989 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2810   -6.5025   -2.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968   -4.4807   -1.0550 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9590   -3.8429   -2.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7063   -2.5814   -2.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786   -1.6505   -1.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1789   -0.2059   -2.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    0.1898   -3.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -3.5429   -0.3609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8340   -3.9552    1.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    0.1307    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    0.2964    2.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -0.9293    1.8224 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5044    3.0553    2.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964    2.7200    3.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    2.3740    2.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3853   -1.3358    2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794   -2.7499    0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8293   -1.3819   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836    0.0608   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778   -1.6801   -0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3405    0.2367   -2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -0.8740   -2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524   -1.7159   -3.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -3.3123   -2.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175   -3.8945   -3.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078   -5.7613   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657   -5.6949   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -6.4623   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -7.4117   -2.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688   -6.8045   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -5.8962   -3.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007   -4.7491   -0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6770   -4.4384   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -2.1983   -3.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639    0.5216   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7721   -3.7749    1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2301    1.1079    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5038   -0.4396    2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    0.3529    3.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    1.2347    1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8838   -1.7751    2.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  8 28  1  0
 28 57  1  1
 28  5  1  0
  3  4  2  0
  5  6  1  0
  3  2  1  0
  7  6  1  1
  2  1  1  0
  8  9  2  0
 13 14  1  0
 11 12  1  0
  7 24  1  0
 21 12  1  0
 24 18  1  0
 14 24  1  0
  7  8  1  0
 18 19  1  0
 10 11  1  0
 19 20  2  0
  9 26  1  0
 18 16  1  0
 26 27  1  0
 16 15  1  0
 15 14  1  0
 27 28  1  0
 16 17  1  0
 21 20  1  0
  9 10  1  0
 21 22  1  1
 12 13  1  0
 22 23  2  0
  7 21  1  0
 22 51  1  0
 12 39  1  6
 24 25  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
  5 32  1  1
  6 33  1  0
  6 34  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 13 40  1  0
 13 41  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 18 48  1  1
 19 49  1  0
 20 50  1  0
 16 44  1  1
 15 42  1  0
 15 43  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 25 52  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₉NO₄

Average Mass

383.4880 Da

Monoisotopic Mass

383.20966 Da

IUPAC Name

methyl (1R,3R,4R,10S,14S,15R,18R,19R)-18-formyl-19-hydroxy-14-methyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icosa-7(20),16-diene-3-carboxylate

Traditional Name

methyl (1R,3R,4R,10S,14S,15R,18R,19R)-18-formyl-19-hydroxy-14-methyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icosa-7(20),16-diene-3-carboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12N3C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])C([H])=C([H])[C@@]1(C([H])=O)[C@@]([H])(C3([H])[H])C([H])([H])C([H])([H])C3=C4[C@]([H])(C([H])([H])C3([H])[H])[C@]([H])(C(=O)OC([H])([H])[H])C([H])([H])[C@]214

InChI Identifier

InChI=1S/C23H29NO4/c1-13-10-24-11-15-5-3-14-4-6-16-17(20(26)28-2)9-22(19(14)16)21(15,12-25)8-7-18(13)23(22,24)27/h7-8,12-13,15-18,27H,3-6,9-11H2,1-2H3/t13-,15-,16-,17-,18-,21-,22-,23-/m1/s1

InChI Key

HEGVMVZUHLZWNS-SNZIKGKMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daphniphyllum himalense	JEOL database	Zhang, Y., et al, Org. Lett. 11, 5414 (2009)
Daphniphyllum macropodum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Indole or derivatives
Indolizidine
N-alkylpyrrolidine
Piperidine
Methyl ester
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Hemiaminal
Tertiary amine
Alkanolamine
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aldehyde
Organooxygen compound
Amine
Organonitrogen 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	1.8	ALOGPS
logP	1.56	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.5	ChemAxon
pKa (Strongest Basic)	9.72	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.91 m³·mol⁻¹	ChemAxon
Polarizability	41.21 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

Not Available

Chemspider ID

28509608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44557841

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang Y, Di YT, Zhang Q, Mu SZ, Tan CJ, Fang X, He HP, Li SL, Hao XJ: Daphhimalenine A, a new alkaloid with an unprecedented skeleton, from Daphniphyllum himalense. Org Lett. 2009 Dec 3;11(23):5414-7. doi: 10.1021/ol902262g. [PubMed:19904981 ]
Zhang, Y., et al. (2009). Zhang, Y., et al, Org. Lett. 11, 5414 (2009). Org. Lett..

Showing NP-Card for daphhimalenine B (NP0038713)

MOL for NP0038713 (daphhimalenine B)

3D MOL for NP0038713 (daphhimalenine B)

3D SDF for NP0038713 (daphhimalenine B)

3D-SDF for NP0038713 (daphhimalenine B)

PDB for NP0038713 (daphhimalenine B)

3D PDB for NP0038713 (daphhimalenine B)

SMILES for NP0038713 (daphhimalenine B)

INCHI for NP0038713 (daphhimalenine B)

Structure for NP0038713 (daphhimalenine B)

3D Structure for NP0038713 (daphhimalenine B)