NP-MRD: Showing NP-Card for 15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one (NP0185825)

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Record Information

Version

2.0

Created at

2022-09-04 01:24:17 UTC

Updated at

2022-09-04 01:24:17 UTC

NP-MRD ID

NP0185825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one

Description

15,21-Dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]Docosan-19-one belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. 15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one is found in Spiraea japonica. 15,21-Dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]Docosan-19-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520072D          

 27 33  0  0  0  0            999 V2000
   -0.8710   -0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -0.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785   -1.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    0.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241    0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247    1.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2045    3.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    2.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    1.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656    1.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867    1.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5395    2.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8337    2.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    1.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4570    0.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6132    0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -0.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245   -0.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944    0.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5960    0.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719    1.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333    0.1478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8553   -0.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5630    0.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784    0.8339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566    0.9068    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 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
 10 27  1  0  0  0  0
 23 27  1  0  0  0  0
M  END

     RDKit          3D

 58 64  0  0  0  0  0  0  0  0999 V2000
   -3.4017   -1.8920    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6669   -0.7258    0.1005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3848   -0.3601   -1.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854    0.7406   -1.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2519    0.9237   -1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5692    0.1036   -0.5988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1547    0.7682    0.7033 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9063   -0.2826    1.1040 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1370    0.6124    1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6987    1.0501    0.0457 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7006    1.0828   -1.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434   -0.1753   -1.1565 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8173   -0.7464   -2.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3203   -1.0784   -0.0480 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7273   -2.4278   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -2.2745   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111   -3.0668   -1.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482   -1.1064   -0.0449 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8344   -1.3364   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369   -0.1084   -0.3424 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9225   -0.0419    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9428   -0.0064   -1.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2916    0.7610    1.5695 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163    2.1166    2.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    2.5456    1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1281    1.6235    0.5431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5788    0.4831    1.0443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7588   -2.7779    0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3131   -2.1693    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6966   -1.5423    1.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5772   -1.2571   -1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4083    0.0105   -0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529    1.7178   -1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8595    0.4891   -2.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966    2.0106   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7086    0.9052   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2158    1.7721    0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6724   -0.7772    2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8162    1.4851    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.0135    1.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112    2.0057    0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371    2.0093   -1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    1.0351   -2.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6432   -1.2745   -2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -2.8316   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7331   -3.0541    0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305   -1.3262    1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0882   -1.7642    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821   -2.1063   -0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3897    0.9523    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997   -0.8005    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8100   -0.0608    1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013   -0.9188   -2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    2.8150    1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    2.0774    3.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915    2.4172    2.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8420    3.5932    1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2113    0.1972    1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  1  6
 20 19  1  0
 19 14  1  0
 14 15  1  1
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18  6  1  0
  6  5  1  6
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  1
  2 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 10 20  1  0
  8 14  1  0
 12 14  1  0
  2 18  1  0
 23 27  1  0
  7  6  1  0
 12  6  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 19 48  1  0
 19 49  1  0
 15 45  1  0
 15 46  1  0
 18 47  1  1
  5 35  1  0
  5 36  1  0
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 58  1  1
 25 56  1  0
 25 57  1  0
 24 54  1  0
 24 55  1  0
  7 37  1  6
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  0
 11 43  1  0
 13 44  1  0
M  END


  Mrv1533004161520072D          

 27 33  0  0  0  0            999 V2000
   -0.8710   -0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -0.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785   -1.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    0.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241    0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247    1.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2045    3.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    2.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    1.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656    1.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867    1.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5395    2.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8337    2.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    1.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4570    0.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6132    0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -0.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245   -0.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944    0.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5960    0.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719    1.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333    0.1478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8553   -0.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5630    0.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784    0.8339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566    0.9068    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 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
 10 27  1  0  0  0  0
 23 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)CC23CC(=O)C4C56CCCC4(C)C4OCCN4C5C2CC1CC36O

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO4/c1-18-4-3-5-21-15(18)14(24)10-20-11-19(2,25)12(9-22(20,21)26)8-13(20)16(21)23-6-7-27-17(18)23/h12-13,15-17,25-26H,3-11H2,1-2H3

> <INCHI_KEY>
RWPBJKJMLUNVRU-UHFFFAOYSA-N

> <FORMULA>
C22H31NO4

> <MOLECULAR_WEIGHT>
373.493

> <EXACT_MASS>
373.225308482

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.49040113252117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
1.0017311596666665

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.827505733322923

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.854069673219207

> <JCHEM_PKA_STRONGEST_BASIC>
7.27729792055373

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
98.22859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one

> <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      -1.626  -0.225   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.109  -0.494   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.520  -1.978   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.019   1.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.538   1.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.353   3.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.587   4.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.248   5.792   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.144   3.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.752   3.049   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.216   2.571   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.255   3.615   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.607   5.013   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.290   4.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.439   2.507   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.586   0.884   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.011   0.544   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.907  -1.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.352  -1.051   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.856   0.440   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.979   1.782   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.561   3.264   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       6.035   0.276   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       7.196  -0.736   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.518   0.056   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.173   1.557   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.639   1.693   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   19                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   17   21                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   12   27                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16   21                                             
CONECT   16   15   17   23                                                  
CONECT   17   16    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5   15   22                                             
CONECT   22   21                                                            
CONECT   23   16   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   10   23                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₁NO₄

Average Mass

373.4930 Da

Monoisotopic Mass

373.22531 Da

IUPAC Name

15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one

Traditional Name

15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one

CAS Registry Number

Not Available

SMILES

CC1(O)CC23CC(=O)C4C56CCCC4(C)C4OCCN4C5C2CC1CC36O

InChI Identifier

InChI=1S/C22H31NO4/c1-18-4-3-5-21-15(18)14(24)10-20-11-19(2,25)12(9-22(20,21)26)8-13(20)16(21)23-6-7-27-17(18)23/h12-13,15-17,25-26H,3-11H2,1-2H3

InChI Key

RWPBJKJMLUNVRU-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
Spiraea japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Piperidine
Cyclic alcohol
Oxazolidine
Tertiary alcohol
Hemiaminal
Ketone
Organoheterocyclic compound
Oxacycle
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.58	ALOGPS
logP	1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	7.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	98.23 m³·mol⁻¹	ChemAxon
Polarizability	40.49 Å³	ChemAxon
Number of Rings	7	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one (NP0185825)

MOL for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

3D MOL for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

3D SDF for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

3D-SDF for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

PDB for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

3D PDB for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

SMILES for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

INCHI for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

Structure for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)

3D Structure for NP0185825 (15,21-dihydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]docosan-19-one)