NP-MRD: Showing NP-Card for (12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione (NP0214441)

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Record Information

Version

2.0

Created at

2022-09-05 13:44:27 UTC

Updated at

2022-09-05 13:44:27 UTC

NP-MRD ID

NP0214441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione

Description

(12S,16R,17S,19R,20S)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]Docosa-1(22),2(7),8(21)-triene-3,9-dione 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. (12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione is found in Daphniphyllum macropodum. Based on a literature review very few articles have been published on (12S,16R,17S,19R,20S)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]Docosa-1(22),2(7),8(21)-triene-3,9-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215442D          

 28 33  0  0  1  0            999 V2000
    0.4957   -0.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    0.6597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5551    1.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838    2.2150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845    3.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503    3.2097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4969    3.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3275    4.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184    3.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889    3.7155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8831    2.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3801    1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859    0.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1443   -0.1400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8724    0.5469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8467   -0.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227    1.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    1.9873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3976    2.4396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9745    3.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2236    1.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5246    1.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3403    2.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8550    1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5540    0.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7383    0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4374   -0.1942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  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  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  6  0  0  0
 13 22  1  0  0  0  0
 22 23  2  0  0  0  0
 11 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
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          3D

 53 58  0  0  0  0  0  0  0  0999 V2000
   -4.0772   -1.3856    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5587   -1.2606    0.8654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1113    0.0397    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418    1.0356    0.5683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8159    2.0405    0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208    2.5496   -0.3255 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8288    3.4105   -0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143    3.1781    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612    1.8221    0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8117    1.7022   -0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335    0.5352    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505    0.2646   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4446   -1.1896   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5940   -1.9330   -0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263   -3.2216   -0.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0284   -1.5525   -0.5217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8399   -2.5522   -1.0523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1894   -0.3595   -1.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7190    0.8628   -0.8158 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2510    1.2379   -1.1004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0103    1.4256   -2.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089   -1.7310    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4315   -0.6939    0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7559   -0.9215    1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1916   -2.3401    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655   -3.2462    1.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -3.0773    0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668   -4.0629    0.8268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5222   -1.2216    1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3096   -2.4362    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4656   -0.6550    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2147   -2.1175    1.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9456    0.4026    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746   -0.1715    2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948    2.8522    1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0370    1.6877    1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997    3.0903   -0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4941    4.4753   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1706    3.4591   -1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273    3.3033    1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213    3.8916    0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197   -3.6578   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896   -2.6490   -2.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2794   -0.2851   -1.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6906   -0.6346   -2.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2869    1.7336   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508    0.4938   -3.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328    1.7815   -2.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    2.1489   -2.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497   -0.2857    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -0.7278    2.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4313   -2.5658    0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0923   -2.4892    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 16  2  1  0
 19  4  1  0
 20  6  1  0
 23 11  1  0
 20 12  1  0
 27 22  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  6
 21 47  1  0
 21 48  1  0
 21 49  1  0
M  END


  Mrv1652309052215442D          

 28 33  0  0  1  0            999 V2000
    0.4957   -0.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    0.6597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5551    1.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838    2.2150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845    3.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503    3.2097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4969    3.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3275    4.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184    3.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889    3.7155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8831    2.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3801    1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859    0.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1443   -0.1400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8724    0.5469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8467   -0.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227    1.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    1.9873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3976    2.4396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9745    3.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2236    1.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5246    1.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3403    2.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8550    1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5540    0.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7383    0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4374   -0.1942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  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  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  6  0  0  0
 13 22  1  0  0  0  0
 22 23  2  0  0  0  0
 11 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
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0214441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CN2C[C@H]3CCC(=O)C4=C5C(C6=C4CCOC6=O)=C(O)[C@]1(O)C[C@@H]2[C@@]35C

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO5/c1-10-8-23-9-11-3-4-13(24)15-12-5-6-28-20(26)16(12)17-18(15)21(11,2)14(23)7-22(10,27)19(17)25/h10-11,14,25,27H,3-9H2,1-2H3/t10-,11-,14-,21-,22+/m1/s1

> <INCHI_KEY>
DVKSQGISDRUSQM-TVZJKCRNSA-N

> <FORMULA>
C22H25NO5

> <MOLECULAR_WEIGHT>
383.444

> <EXACT_MASS>
383.173272909

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.90447845026158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(12S,16R,17S,19R,20S)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0^{2,7}.0^{8,21}.0^{12,20}.0^{14,19}]docosa-1(22),2(7),8(21)-triene-3,9-dione

> <JCHEM_LOGP>
-2.810753139087011

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.662527359920343

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.950261919821582

> <JCHEM_PKA_STRONGEST_BASIC>
10.412985358074001

> <JCHEM_POLAR_SURFACE_AREA>
87.07000000000002

> <JCHEM_REFRACTIVITY>
103.58489999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(12S,16R,17S,19R,20S)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0^{2,7}.0^{8,21}.0^{12,20}.0^{14,19}]docosa-1(22),2(7),8(21)-triene-3,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.925  -0.033   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.804   1.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.036   2.707   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.836   4.135   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.211   5.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.827   5.991   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.661   7.322   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.211   7.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.314   6.385   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.753   6.936   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.249   4.787   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.925   3.938   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.309   2.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.200   1.126   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.869  -0.261   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.495   1.021   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.447  -0.518   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.402   2.228   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.236   3.710   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.475   4.554   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.552   5.655   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.884   2.275   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.446   3.709   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.969   3.939   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.929   2.736   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.368   1.302   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.845   1.071   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.283  -0.363   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   23                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    2   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    4   20                                                  
CONECT   20   19   12    6   21                                             
CONECT   21   20                                                            
CONECT   22   13   23   27                                                  
CONECT   23   22   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₅NO₅

Average Mass

383.4440 Da

Monoisotopic Mass

383.17327 Da

IUPAC Name

(12S,16R,17S,19R,20S)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0^{2,7}.0^{8,21}.0^{12,20}.0^{14,19}]docosa-1(22),2(7),8(21)-triene-3,9-dione

Traditional Name

(12S,16R,17S,19R,20S)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0^{2,7}.0^{8,21}.0^{12,20}.0^{14,19}]docosa-1(22),2(7),8(21)-triene-3,9-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1CN2C[C@H]3CCC(=O)C4=C5C(C6=C4CCOC6=O)=C(O)[C@]1(O)C[C@@H]2[C@@]35C

InChI Identifier

InChI=1S/C22H25NO5/c1-10-8-23-9-11-3-4-13(24)15-12-5-6-28-20(26)16(12)17-18(15)21(11,2)14(23)7-22(10,27)19(17)25/h10-11,14,25,27H,3-9H2,1-2H3/t10-,11-,14-,21-,22+/m1/s1

InChI Key

DVKSQGISDRUSQM-TVZJKCRNSA-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
Dihydropyranone
Piperidine
Pyran
N-alkylpyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Ketone
Tertiary aliphatic amine
Tertiary amine
Lactone
Oxacycle
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Enol
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
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	-2.8	ChemAxon
pKa (Strongest Acidic)	5.95	ChemAxon
pKa (Strongest Basic)	10.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	103.58 m³·mol⁻¹	ChemAxon
Polarizability	39.9 Å³	ChemAxon
Number of Rings	6	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

54714056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione (NP0214441)

MOL for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

3D MOL for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

3D SDF for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

3D-SDF for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

PDB for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

3D PDB for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

SMILES for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

INCHI for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

Structure for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)

3D Structure for NP0214441 ((12s,16r,17s,19r,20s)-17,22-dihydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.0²,⁷.0⁸,²¹.0¹²,²⁰.0¹⁴,¹⁹]docosa-1(22),2(7),8(21)-triene-3,9-dione)