NP-MRD: Showing NP-Card for methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate (NP0307614)

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Record Information

Version

2.0

Created at

2022-09-11 00:51:39 UTC

Updated at

2022-09-11 00:51:39 UTC

NP-MRD ID

NP0307614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate

Description

385384-29-2 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. methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate is found in Daphniphyllum macropodum. 385384-29-2 Is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161503182D          

 29 33  0  0  0  0            999 V2000
    5.5772   -0.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -0.2147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538   -0.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440   -0.7461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5935    1.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4177    1.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7974    2.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216    2.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691    2.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866    1.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3273    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6184    0.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287   -0.4599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109    0.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    1.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    1.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1563    2.2635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898    1.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177    3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    3.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9668    3.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8021    3.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667    2.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0793    3.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869    2.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2656    2.6837    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  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 28  1  0  0  0  0
 11 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
    3.3503   -4.2623    0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4852   -3.2127    0.2611 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516   -1.9032    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1041   -1.7096    0.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0434   -0.7683   -0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873    0.5184   -0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7534    1.0566   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    1.9209    1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484    1.1444    2.2417 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2066    1.3279   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1737    0.5351   -0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6127   -0.8340   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947   -1.9085   -0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -3.0648   -0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -2.1321   -0.2240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3166   -1.1691   -1.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366    0.0774   -0.4570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1912    0.4698    0.2118 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2419   -0.6091    1.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770   -1.6806    1.0949 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8818   -2.9270    1.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8245    1.7893    0.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5227    2.1718   -0.0716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2172    3.4367   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2286    3.7773   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    2.8035   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    3.2309   -1.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2305    1.0654   -1.1175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4425    1.4574   -2.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447   -4.1653    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860   -4.3530    1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9126   -5.2133    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481    0.3144   -0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0320    1.7047   -1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9406    2.1844    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2386    2.7982    1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3275    0.5604    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531   -3.9768   -0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9297   -3.1729   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8040   -1.1955   -2.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922   -1.4069   -1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493   -0.0769    0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1065   -0.1392    2.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2705   -1.0214    1.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3477   -1.5229    1.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -2.5571    2.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6289   -3.3201    0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1162   -3.6635    1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604    2.4720    0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8137    1.8684    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709    1.9348    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7609    4.2688   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    3.5964   -1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437    4.1772    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3859    4.6979   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4216    1.9909   -2.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    2.0478   -2.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594    0.5667   -3.1421 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  1  0
  8  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 23 28  1  0
 28 29  1  6
 18 19  1  0
 19 20  1  0
 20 21  1  0
 12  5  1  0
 20 15  1  0
 26 10  1  0
 28 11  1  0
 28 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 14 38  1  0
 15 39  1  6
 16 40  1  0
 16 41  1  0
 17 42  1  1
 22 49  1  0
 22 50  1  0
 23 51  1  1
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 29 56  1  0
 29 57  1  0
 29 58  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  1
 21 46  1  0
 21 47  1  0
 21 48  1  0
M  END


  Mrv1533004161503182D          

 29 33  0  0  0  0            999 V2000
    5.5772   -0.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -0.2147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538   -0.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440   -0.7461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5935    1.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4177    1.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7974    2.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216    2.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691    2.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866    1.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3273    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6184    0.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287   -0.4599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109    0.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    1.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    1.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1563    2.2635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898    1.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177    3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    3.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9668    3.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8021    3.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667    2.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0793    3.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869    2.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2656    2.6837    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  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 28  1  0  0  0  0
 11 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307614

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(CCO)C2=C3C1=C(O)C1CC4N(CC(CCC2=O)C34C)CC1C

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO5/c1-11-9-24-10-12-4-5-15(26)17-13(6-7-25)18(22(28)29-3)19-20(17)23(12,2)16(24)8-14(11)21(19)27/h11-12,14,16,25,27H,4-10H2,1-3H3

> <INCHI_KEY>
VNGVJVLIJHNWFZ-UHFFFAOYSA-N

> <FORMULA>
C23H29NO5

> <MOLECULAR_WEIGHT>
399.487

> <EXACT_MASS>
399.204573038

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.2448970185941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
-1.8850180730914632

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.26704234430255

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.006390166110172

> <JCHEM_PKA_STRONGEST_BASIC>
10.900883944829609

> <JCHEM_POLAR_SURFACE_AREA>
87.07

> <JCHEM_REFRACTIVITY>
110.53749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      10.411  -1.830   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.838  -0.401   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.314  -0.182   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.362  -1.393   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.741   1.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.575   2.562   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.113   2.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.822   3.999   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.360   4.069   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.596   3.835   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.135   3.253   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.211   1.628   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.888   0.631   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.280  -0.858   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.194   0.853   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.332   2.055   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.451   3.541   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.158   4.225   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.101   2.976   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.574   1.381   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.470   0.307   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.833   5.736   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.466   5.669   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.538   6.816   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.097   6.712   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.965   5.391   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.481   5.658   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.829   4.134   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.096   5.010   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   12                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11   26                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11    5   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   10   27                                                  
CONECT   27   26                                                            
CONECT   28   23   11   17   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₉NO₅

Average Mass

399.4870 Da

Monoisotopic Mass

399.20457 Da

IUPAC Name

methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate

Traditional Name

methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(CCO)C2=C3C1=C(O)C1CC4N(CC(CCC2=O)C34C)CC1C

InChI Identifier

InChI=1S/C23H29NO5/c1-11-9-24-10-12-4-5-15(26)17-13(6-7-25)18(22(28)29-3)19-20(17)23(12,2)16(24)8-14(11)21(19)27/h11-12,14,16,25,27H,4-10H2,1-3H3

InChI Key

VNGVJVLIJHNWFZ-UHFFFAOYSA-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 macropodum	LOTUS Database	35616633

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
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Ketone
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Enol
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Primary 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	1.77	ALOGPS
logP	-1.9	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	10.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.54 m³·mol⁻¹	ChemAxon
Polarizability	43.24 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76172616

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate (NP0307614)

MOL for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

3D MOL for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

3D SDF for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

3D-SDF for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

PDB for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

3D PDB for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

SMILES for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

INCHI for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

Structure for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)

3D Structure for NP0307614 (methyl 18-hydroxy-11-(2-hydroxyethyl)-2,15-dimethyl-9-oxo-4-azapentacyclo[11.4.1.0⁴,¹⁶.0⁶,¹⁵.0¹⁰,¹⁴]octadeca-10(14),11,13(18)-triene-12-carboxylate)