NP-MRD: Showing NP-Card for methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate (NP0251517)

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Record Information

Version

2.0

Created at

2022-09-07 14:44:11 UTC

Updated at

2022-09-07 14:44:11 UTC

NP-MRD ID

NP0251517

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Methyl (2S,3R,5R,10S)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]Henicosa-1(19),13(20),17-triene-18-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. methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate is found in Daphniphyllum calycinum, Daphniphyllum macropodum and Daphniphyllum oldhamii. Based on a literature review very few articles have been published on methyl (2S,3R,5R,10S)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]Henicosa-1(19),13(20),17-triene-18-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216442D          

 28 33  0  0  1  0            999 V2000
    4.9410   -1.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8097   -1.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386   -0.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990   -1.2395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4938    0.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204    0.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7864    1.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4262    2.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5829    2.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2972    1.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    0.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555    0.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -0.7234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7075    1.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9485    1.7899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3597    2.3017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524    1.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    0.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0120    0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    3.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    2.7917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4766    3.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689    2.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    1.9480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5025    2.2381    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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
 24 27  1  0  0  0  0
 12 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
    3.6541    4.0886   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    3.0835   -0.1397 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9346    1.7589   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877    1.4966   -0.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399    0.6356   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3851   -0.6118   -0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925   -1.3013   -0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301   -2.6675   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5437   -3.3852   -0.5405 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3575   -2.7542   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -1.4390   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.6080    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818    0.6380    0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726    1.8920    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7903    2.8286    1.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    2.1728    0.8451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9835    1.1142    1.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2265   -0.1748    1.1163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9212   -0.1117   -0.1460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950    1.1172   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    2.1217   -0.5432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5183    3.5011   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -1.2695   -0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574   -2.1400    0.0377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9598   -3.0578   -0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -3.7095   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -1.1355    0.9233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8688   -1.8191    2.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    3.7214   -0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5351    4.9095    0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551    4.5053   -1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4274   -1.5251   -2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5058   -0.7338   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7646   -2.4572    0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6333   -3.1685   -0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    3.1491    1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185    1.5269    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2606    0.9551    2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679   -0.7243    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9879    1.6016   -0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368    0.9448   -1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1229    1.9739   -1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9350    3.5187   -1.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739    4.2979   -0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435    3.6714   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5253   -1.8078   -1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481   -1.0595   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5068   -2.7065    0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -2.5482   -1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190   -3.8569   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4921   -4.6055   -0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0367   -4.0438    0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405   -1.0231    3.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -2.6626    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815   -2.1165    2.3511 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
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 13  5  1  0
 21 16  1  0
 11  6  1  0
 27 12  1  0
 26 10  1  0
 27 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 16 36  1  1
 17 37  1  0
 17 38  1  0
 18 39  1  1
 23 46  1  0
 23 47  1  0
 24 48  1  1
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 28 53  1  0
 28 54  1  0
 28 55  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  6
 22 43  1  0
 22 44  1  0
 22 45  1  0
M  END


  Mrv1652309072216442D          

 28 33  0  0  1  0            999 V2000
    4.9410   -1.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8097   -1.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386   -0.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990   -1.2395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4938    0.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204    0.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7864    1.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4262    2.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5829    2.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2972    1.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    0.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555    0.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -0.7234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7075    1.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9485    1.7899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3597    2.3017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524    1.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    0.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0120    0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    3.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473    2.7917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4766    3.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689    2.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    1.9480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5025    2.2381    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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
 24 27  1  0  0  0  0
 12 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0251517

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2CCOC3=C2C2=C1C(=O)[C@@H]1C[C@H]4N(C[C@@H](CC3)[C@@]24C)CC1C

> <INCHI_IDENTIFIER>
InChI=1S/C23H27NO4/c1-11-9-24-10-12-4-5-15-17-13(6-7-28-15)18(22(26)27-3)19-20(17)23(12,2)16(24)8-14(11)21(19)25/h11-12,14,16H,4-10H2,1-3H3/t11?,12-,14-,16-,23-/m1/s1

> <INCHI_KEY>
DTNVJGYTJYNCDT-LWDBLAEISA-N

> <FORMULA>
C23H27NO4

> <MOLECULAR_WEIGHT>
381.472

> <EXACT_MASS>
381.194008353

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.59066215870676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.3117521909999992

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.231627148988782

> <JCHEM_PKA_STRONGEST_BASIC>
10.757035908303422

> <JCHEM_POLAR_SURFACE_AREA>
55.84

> <JCHEM_REFRACTIVITY>
107.13029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       9.223  -3.409   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.978  -1.889   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.539  -1.341   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.345  -2.314   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.294   0.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.388   1.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.931   1.101   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.801   2.377   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.129   3.791   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.555   4.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.700   2.698   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.155   2.474   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.891   0.882   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.397   0.188   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.463  -1.350   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.800   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.187   1.898   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.637   3.341   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.538   4.296   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.218   3.306   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.335   1.648   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.022   0.842   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.545   5.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.128   5.211   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.490   6.033   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.969   5.519   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.096   3.636   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.538   4.178   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   10                                                       
CONECT   27   24   12   18   28                                             
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S,3R,5R,10S)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1,.0,.0,.0,]henicosa-1(19),13(20),17-triene-18-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₇NO₄

Average Mass

381.4720 Da

Monoisotopic Mass

381.19401 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2CCOC3=C2C2=C1C(=O)[C@@H]1C[C@H]4N(C[C@@H](CC3)[C@@]24C)CC1C

InChI Identifier

InChI=1S/C23H27NO4/c1-11-9-24-10-12-4-5-15-17-13(6-7-28-15)18(22(26)27-3)19-20(17)23(12,2)16(24)8-14(11)21(19)25/h11-12,14,16H,4-10H2,1-3H3/t11?,12-,14-,16-,23-/m1/s1

InChI Key

DTNVJGYTJYNCDT-LWDBLAEISA-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 calycinum	LOTUS Database	35616633
Daphniphyllum macropodum	LOTUS Database	35616633
Daphniphyllum oldhamii	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
N-alkylpyrrolidine
Piperidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Ketone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	1.31	ChemAxon
pKa (Strongest Acidic)	19.23	ChemAxon
pKa (Strongest Basic)	10.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.13 m³·mol⁻¹	ChemAxon
Polarizability	41.59 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

95532591

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

138114028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate (NP0251517)

MOL for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

3D MOL for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

3D SDF for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

3D-SDF for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

PDB for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

3D PDB for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

SMILES for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

INCHI for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

Structure for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)

3D Structure for NP0251517 (methyl (2s,3r,5r,10s)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.1⁵,¹⁹.0²,¹⁰.0³,⁸.0¹⁷,²⁰]henicosa-1(19),13(20),17-triene-18-carboxylate)