NP-MRD: Showing NP-Card for angustifolimine (NP0040409)

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Record Information

Version

2.0

Created at

2021-06-20 22:34:56 UTC

Updated at

2021-06-30 00:14:18 UTC

NP-MRD ID

NP0040409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

angustifolimine

Provided By

JEOL Database JEOL Logo

Description

Methyl (1R,2S,6S,15S,16R)-9-(ethylamino)-11-(2-hydroxyethyl)-2,15-dimethyl-18-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]Octadeca-9,11,13-triene-12-carboxylate belongs to the class of organic compounds known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring. angustifolimine is found in Daphniphyllum angustifolium. angustifolimine was first documented in 2011 (Zhang, C.-R., et al.). Based on a literature review very few articles have been published on methyl (1R,2S,6S,15S,16R)-9-(ethylamino)-11-(2-hydroxyethyl)-2,15-dimethyl-18-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]Octadeca-9,11,13-triene-12-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100343D          

 65 69  0  0  0  0            999 V2000
    4.0822   -3.7842    1.3573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -2.4490    0.7059 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3289   -2.2805    0.5673 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6158   -1.2300   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -1.1603    0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6198   -1.9270    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2205   -2.7580    2.1286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2361   -4.2608    1.8408 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8893   -4.6325    1.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812   -1.5513    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0607   -1.9488    1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2869   -3.0886    1.8338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767   -0.8387    1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9592   -1.1176    2.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -0.6378   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486   -0.3184   -0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1549    0.5057   -2.0404 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3686   -0.4793   -3.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    1.5714   -1.6188 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9198    1.2441   -0.5491 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4890   -0.1573   -0.6545 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0292    2.7514   -1.1600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0662    2.7998   -2.1223 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3165    3.3092   -1.5663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1233    2.2255   -0.8414 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4293    2.8058   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    1.0351   -1.7808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5650    1.0130   -3.0458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1459    1.4838   -2.7816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2161   -0.2928   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1361   -1.1145   -1.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286   -4.6168    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1629   -3.8945    1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058   -3.8667    2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450   -2.4041   -0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726   -1.6485    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796   -3.1338    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7505   -2.4419    2.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229   -2.5654    2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -4.5662    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1768   -4.8170    2.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583   -5.5676    0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4939   -0.1758    2.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6132   -1.8010    1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7019   -1.5318    3.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -1.2405   -2.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9025    0.0479   -3.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616   -1.0235   -3.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4471    1.8793   -2.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413    1.9675   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    1.4033    0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554   -0.4236   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421   -0.1022   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966    3.6881   -1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    2.5861   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    3.7239   -2.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1189    4.1570   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5515    1.8975    0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2254    3.6252    0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9964    2.0398    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0624    3.1969   -1.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.0647   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270    1.6875   -3.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5655    0.0220   -3.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199    1.6655   -3.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 27  1  0  0  0  0
 30 31  2  0  0  0  0
 15 16  2  0  0  0  0
 17 19  1  0  0  0  0
 29 28  1  0  0  0  0
 29 23  1  0  0  0  0
 27 28  1  0  0  0  0
 23 22  1  0  0  0  0
 19 22  1  0  0  0  0
  6 10  2  0  0  0  0
  4 21  1  0  0  0  0
 16 17  1  0  0  0  0
 21 20  1  0  0  0  0
 19 20  1  0  0  0  0
  6  5  1  0  0  0  0
 27 25  1  0  0  0  0
 10 15  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5  4  2  0  0  0  0
 25 26  1  0  0  0  0
  4  3  1  0  0  0  0
 17 18  1  6  0  0  0
 15 30  1  0  0  0  0
  3  2  1  0  0  0  0
 16  5  1  0  0  0  0
  2  1  1  0  0  0  0
  8  7  1  0  0  0  0
 10 11  1  0  0  0  0
  7  6  1  0  0  0  0
 11 13  1  0  0  0  0
 17 29  1  0  0  0  0
 13 14  1  0  0  0  0
 11 12  2  0  0  0  0
  8  9  1  0  0  0  0
 29 65  1  6  0  0  0
 27 62  1  6  0  0  0
 28 63  1  0  0  0  0
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  8 40  1  0  0  0  0
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  7 38  1  0  0  0  0
  7 39  1  0  0  0  0
  3 37  1  0  0  0  0
  9 42  1  0  0  0  0
 19 49  1  6  0  0  0
 22 54  1  0  0  0  0
 22 55  1  0  0  0  0
 21 52  1  0  0  0  0
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 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
 25 58  1  1  0  0  0
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 26 59  1  0  0  0  0
 26 60  1  0  0  0  0
 26 61  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
  2 35  1  0  0  0  0
  2 36  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
M  END

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
    4.0822   -3.7842    1.3573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -2.4490    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -2.2805    0.5673 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6158   -1.2300   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -1.1603    0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6198   -1.9270    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2205   -2.7580    2.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -4.2608    1.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893   -4.6325    1.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812   -1.5513    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0607   -1.9488    1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2869   -3.0886    1.8338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767   -0.8387    1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9592   -1.1176    2.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6486   -0.3184   -0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8900    1.5714   -1.6188 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.0662    2.7998   -2.1223 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4070    1.0351   -1.7808 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.2161   -0.2928   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1361   -1.1145   -1.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6058   -3.8667    2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7413    1.9675   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    1.4033    0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5966    3.6881   -1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9156    3.7239   -2.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1189    4.1570   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5515    1.8975    0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2254    3.6252    0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9964    2.0398    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4596    1.0647   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270    1.6875   -3.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7199    1.6655   -3.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212100343D          

 65 69  0  0  0  0            999 V2000
    4.0822   -3.7842    1.3573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -2.4490    0.7059 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3289   -2.2805    0.5673 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6158   -1.2300   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -1.1603    0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6198   -1.9270    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2205   -2.7580    2.1286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2361   -4.2608    1.8408 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0040409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C([H])([H])C1=C(C(=O)OC([H])([H])[H])C2=C3C1=C(N([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])C([H])([H])N4C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]([H])(C2=O)C([H])([H])[C@]4([H])[C@]31C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H34N2O4/c1-5-26-17-7-6-14-12-27-11-13(2)16-10-18(27)25(14,3)22-19(17)15(8-9-28)20(24(30)31-4)21(22)23(16)29/h13-14,16,18,26,28H,5-12H2,1-4H3/t13-,14-,16-,18-,25-/m1/s1

> <INCHI_KEY>
SDSMTXJRSRUFDM-VZKQBJJXSA-N

> <FORMULA>
C25H34N2O4

> <MOLECULAR_WEIGHT>
426.557

> <EXACT_MASS>
426.251857583

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.81300460267819

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,6S,15S,16R)-9-(ethylamino)-11-(2-hydroxyethyl)-2,15-dimethyl-18-oxo-4-azapentacyclo[11.4.1.0^{4,16}.0^{6,15}.0^{10,14}]octadeca-9,11,13-triene-12-carboxylate

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
0.8325551703333325

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
19.234151496139255

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.267088897900997

> <JCHEM_PKA_STRONGEST_BASIC>
10.847617728613066

> <JCHEM_POLAR_SURFACE_AREA>
78.87

> <JCHEM_REFRACTIVITY>
121.82109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,6S,15S,16R)-9-(ethylamino)-11-(2-hydroxyethyl)-2,15-dimethyl-18-oxo-4-azapentacyclo[11.4.1.0^{4,16}.0^{6,15}.0^{10,14}]octadeca-9,11,13-triene-12-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
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M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       4.082  -3.784   1.357  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.763  -2.449   0.706  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.329  -2.281   0.567  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.616  -1.230  -0.010  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.254  -1.160   0.017  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.620  -1.927   0.937  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.221  -2.758   2.129  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.236  -4.261   1.841  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.889  -4.633   1.050  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.881  -1.551   0.659  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.061  -1.949   1.455  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.287  -3.089   1.834  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.777  -0.839   1.777  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.959  -1.118   2.525  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.910  -0.638  -0.472  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.649  -0.318  -0.848  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.155   0.506  -2.040  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.369  -0.479  -3.117  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.890   1.571  -1.619  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.920   1.244  -0.549  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.489  -0.157  -0.655  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.029   2.751  -1.160  0.00  0.00           C+0
HETATM   23  N   UNK     0      -1.066   2.800  -2.122  0.00  0.00           N+0
HETATM   24  C   UNK     0      -2.317   3.309  -1.566  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.123   2.225  -0.841  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.429   2.806  -0.291  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.407   1.035  -1.781  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.565   1.013  -3.046  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.146   1.484  -2.782  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.216  -0.293  -1.096  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.136  -1.115  -1.083  0.00  0.00           O+0
HETATM   32  H   UNK     0       3.729  -4.617   0.740  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.163  -3.894   1.490  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.606  -3.867   2.340  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.245  -2.404  -0.277  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.173  -1.649   1.331  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.780  -3.134   0.735  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.751  -2.442   2.523  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.923  -2.565   2.950  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.146  -4.566   1.315  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.177  -4.817   2.782  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.758  -5.568   0.810  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.494  -0.176   2.676  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.613  -1.801   1.974  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.702  -1.532   3.505  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.048  -1.240  -2.729  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.903   0.048  -3.916  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.462  -1.024  -3.582  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.447   1.879  -2.518  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.741   1.968  -0.644  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.515   1.403   0.460  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.755  -0.424  -1.682  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.442  -0.102  -0.115  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.597   3.688  -1.169  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.334   2.586  -0.138  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.916   3.724  -2.388  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.119   4.157  -0.898  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.551   1.898   0.035  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.225   3.625   0.406  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.996   2.040   0.249  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.062   3.197  -1.095  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.460   1.065  -2.096  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.027   1.688  -3.780  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.566   0.022  -3.516  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.720   1.666  -3.781  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1   35   36                                             
CONECT    3    4    2   37                                                  
CONECT    4   21    5    3                                                  
CONECT    5    6    4   16                                                  
CONECT    6   10    5    7                                                  
CONECT    7    8    6   38   39                                             
CONECT    8    7    9   40   41                                             
CONECT    9    8   42                                                       
CONECT   10    6   15   11                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   43   44   45                                             
CONECT   15   16   10   30                                                  
CONECT   16   15   17    5                                                  
CONECT   17   19   16   18   29                                             
CONECT   18   17   46   47   48                                             
CONECT   19   17   22   20   49                                             
CONECT   20   21   19   50   51                                             
CONECT   21    4   20   52   53                                             
CONECT   22   23   19   54   55                                             
CONECT   23   29   22   24                                                  
CONECT   24   23   25   56   57                                             
CONECT   25   27   24   26   58                                             
CONECT   26   25   59   60   61                                             
CONECT   27   30   28   25   62                                             
CONECT   28   29   27   63   64                                             
CONECT   29   28   23   17   65                                             
CONECT   30   27   31   15                                                  
CONECT   31   30                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    2                                                            
CONECT   37    3                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   28                                                            
CONECT   65   29                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  138    0
END

RDKit          3D

65 69  0  0  0  0  0  0  0  0999 V2000
    4.0822   -3.7842    1.3573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -2.4490    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -2.2805    0.5673 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6158   -1.2300   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -1.1603    0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6198   -1.9270    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2361   -4.2608    1.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893   -4.6325    1.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812   -1.5513    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0607   -1.9488    1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2869   -3.0886    1.8338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767   -0.8387    1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9592   -1.1176    2.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -0.6378   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486   -0.3184   -0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1549    0.5057   -2.0404 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3686   -0.4793   -3.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    1.5714   -1.6188 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9198    1.2441   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -0.1573   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292    2.7514   -1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0662    2.7998   -2.1223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3165    3.3092   -1.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233    2.2255   -0.8414 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4293    2.8058   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    1.0351   -1.7808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5650    1.0130   -3.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459    1.4838   -2.7816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2161   -0.2928   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1361   -1.1145   -1.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286   -4.6168    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1629   -3.8945    1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058   -3.8667    2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450   -2.4041   -0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726   -1.6485    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796   -3.1338    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7505   -2.4419    2.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229   -2.5654    2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -4.5662    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1768   -4.8170    2.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583   -5.5676    0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4939   -0.1758    2.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6132   -1.8010    1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7019   -1.5318    3.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -1.2405   -2.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9025    0.0479   -3.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616   -1.0235   -3.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4471    1.8793   -2.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413    1.9675   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    1.4033    0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554   -0.4236   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421   -0.1022   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966    3.6881   -1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    2.5861   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    3.7239   -2.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1189    4.1570   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5515    1.8975    0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2254    3.6252    0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9964    2.0398    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0624    3.1969   -1.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.0647   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270    1.6875   -3.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5655    0.0220   -3.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199    1.6655   -3.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 27  1  0
 30 31  2  0
 15 16  2  0
 17 19  1  0
 29 28  1  0
 29 23  1  0
 27 28  1  0
 23 22  1  0
 19 22  1  0
  6 10  2  0
  4 21  1  0
 16 17  1  0
 21 20  1  0
 19 20  1  0
  6  5  1  0
 27 25  1  0
 10 15  1  0
 23 24  1  0
 24 25  1  0
  5  4  2  0
 25 26  1  0
  4  3  1  0
 17 18  1  6
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  3  2  1  0
 16  5  1  0
  2  1  1  0
  8  7  1  0
 10 11  1  0
  7  6  1  0
 11 13  1  0
 17 29  1  0
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  8  9  1  0
 29 65  1  6
 27 62  1  6
 28 63  1  0
 28 64  1  0
  8 40  1  0
  8 41  1  0
  7 38  1  0
  7 39  1  0
  3 37  1  0
  9 42  1  0
 19 49  1  6
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 21 53  1  0
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 20 51  1  0
 25 58  1  1
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 24 57  1  0
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 26 61  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
  2 35  1  0
  2 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2S,6S,15S,16R)-9-(ethylamino)-11-(2-hydroxyethyl)-2,15-dimethyl-18-oxo-4-azapentacyclo[11.4.1.0,.0,.0,]octadeca-9,11,13-triene-12-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₄N₂O₄

Average Mass

426.5570 Da

Monoisotopic Mass

426.25186 Da

IUPAC Name

methyl (1R,2S,6S,15S,16R)-9-(ethylamino)-11-(2-hydroxyethyl)-2,15-dimethyl-18-oxo-4-azapentacyclo[11.4.1.0^{4,16}.0^{6,15}.0^{10,14}]octadeca-9,11,13-triene-12-carboxylate

Traditional Name

methyl (1R,2S,6S,15S,16R)-9-(ethylamino)-11-(2-hydroxyethyl)-2,15-dimethyl-18-oxo-4-azapentacyclo[11.4.1.0^{4,16}.0^{6,15}.0^{10,14}]octadeca-9,11,13-triene-12-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C([H])([H])C1=C(C(=O)OC([H])([H])[H])C2=C3C1=C(N([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])C([H])([H])N4C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]([H])(C2=O)C([H])([H])[C@]4([H])[C@]31C([H])([H])[H]

InChI Identifier

InChI=1S/C25H34N2O4/c1-5-26-17-7-6-14-12-27-11-13(2)16-10-18(27)25(14,3)22-19(17)15(8-9-28)20(24(30)31-4)21(22)23(16)29/h13-14,16,18,26,28H,5-12H2,1-4H3/t13-,14-,16-,18-,25-/m1/s1

InChI Key

SDSMTXJRSRUFDM-VZKQBJJXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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 angustifolium	JEOL database	Zhang, C.-R., et al, Org. Let. 13, 2440 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring.

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Unsaturated hydrocarbons

Sub Class

Olefins

Direct Parent

Azulenes

Alternative Parents

Substituents

Azulene
Indolizidine
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Ketone
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Secondary aliphatic amine
Enamine
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Primary alcohol
Carbonyl group
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	2.22	ALOGPS
logP	0.83	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	17.27	ChemAxon
pKa (Strongest Basic)	10.85	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.87 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.82 m³·mol⁻¹	ChemAxon
Polarizability	47.81 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

28288838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53248169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, C.-R., et al. (2011). Zhang, C.-R., et al, Org. Let. 13, 2440 (2011). Org. Lett..

Showing NP-Card for angustifolimine (NP0040409)

MOL for NP0040409 (angustifolimine)

3D MOL for NP0040409 (angustifolimine)

3D SDF for NP0040409 (angustifolimine)

3D-SDF for NP0040409 (angustifolimine)

PDB for NP0040409 (angustifolimine)

3D PDB for NP0040409 (angustifolimine)

SMILES for NP0040409 (angustifolimine)

INCHI for NP0040409 (angustifolimine)

Structure for NP0040409 (angustifolimine)

3D Structure for NP0040409 (angustifolimine)