NP-MRD: Showing NP-Card for 10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate (NP0287111)

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Record Information

Version

2.0

Created at

2022-09-09 16:01:18 UTC

Updated at

2022-09-09 16:01:18 UTC

NP-MRD ID

NP0287111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate

Description

10-Hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-18-yl acetate belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class. 10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate is found in Delphinium fissum. 10-Hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-18-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512332D          

 27 33  0  0  0  0            999 V2000
    2.4664   -2.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124   -3.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -3.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905   -2.6015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226   -1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129   -2.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -1.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9110   -0.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -0.1838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374   -1.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7254   -1.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044   -0.8131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4264   -1.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1535   -1.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9722   -2.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2238   -2.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5360   -3.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5987   -4.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857   -2.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6634   -2.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4024   -1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430   -0.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4622   -0.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -0.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016   -0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532   -0.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 54 60  0  0  0  0  0  0  0  0999 V2000
    4.6962    0.4156   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4679    0.0229    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6409    0.3161    1.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    0.0549    0.9524 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2894    0.3262    2.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808   -0.1921    1.8370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6394    0.3145    0.4978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8857   -0.4960    0.4190 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0031    0.0562    1.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3918   -0.7888   -0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -0.0767   -1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0555    0.6635   -2.7153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644   -0.3348   -1.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -0.2904   -0.4260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2929   -1.5781    0.2409 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1371   -1.4556    0.7468 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1335   -1.9749   -0.2496 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4952   -2.8066   -1.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774   -0.7938   -0.9384 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6119    0.0637   -1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    0.5303   -0.3304 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3066    1.7932   -0.5499 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408    2.9731   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1986    4.2167   -0.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1625    2.9033   -0.6228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826   -1.6219    1.4896 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580   -1.8107    1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2251    0.1640   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1724    1.0107    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609    1.2922    1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555   -0.4361    2.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6932   -0.2847    2.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    1.3790    2.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7382    0.0322    2.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    1.3798    0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7169    0.3292    2.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7803   -0.7585    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4910    0.8797    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4623   -0.4799   -1.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -1.8840   -1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8047   -1.2633   -2.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902    0.5352   -2.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565   -2.4748   -0.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -1.9188    1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156   -2.5458    0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9990   -3.6352   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3959   -1.0519   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    0.9532   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -0.5714   -2.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971    4.4939   -0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821    5.0646   -1.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286    4.1435   -1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4172   -2.6311    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1260   -2.1515    1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 25  2  0
 23 22  1  0
 21 22  1  1
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16 15  1  0
 15 26  1  0
 26 27  1  0
 27  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 14 13  1  6
 14  7  1  0
  7  6  1  0
  6  5  1  0
  4  5  1  1
  4  3  1  0
  3  2  1  0
  2  1  2  3
 14 21  1  0
  4 21  1  0
  2 19  1  0
  4 16  1  0
 14 15  1  0
  6 26  1  0
  7  8  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
 20 48  1  0
 20 49  1  0
 19 47  1  6
 17 45  1  1
 18 46  1  0
 16 44  1  1
 15 43  1  6
 27 53  1  0
 27 54  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 13 41  1  0
 13 42  1  0
  7 35  1  1
  6 34  1  1
  5 32  1  0
  5 33  1  0
  3 30  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1533004251512332D          

 27 33  0  0  0  0            999 V2000
    2.4664   -2.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124   -3.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -3.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905   -2.6015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226   -1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129   -2.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -1.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9110   -0.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -0.1838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374   -1.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7254   -1.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044   -0.8131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4264   -1.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1535   -1.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9722   -2.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2238   -2.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5360   -3.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5987   -4.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857   -2.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6634   -2.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4024   -1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430   -0.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4622   -0.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -0.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016   -0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532   -0.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0287111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC12CC3C(O)C4C5N6CC7(C)CC(=O)CC15C7C6CC24CC3=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO4/c1-10-4-20-8-14-17-19(3)5-12(25)6-21(17)18(23(14)9-19)15(20)16(26)13(10)7-22(20,21)27-11(2)24/h13-18,26H,1,4-9H2,2-3H3

> <INCHI_KEY>
OPSQHQOWJPAFNK-UHFFFAOYSA-N

> <FORMULA>
C22H27NO4

> <MOLECULAR_WEIGHT>
369.461

> <EXACT_MASS>
369.194008353

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.1497663819969

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
-0.010322614999999816

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.636334417868074

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.546548081244364

> <JCHEM_PKA_STRONGEST_BASIC>
8.491400899915561

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
96.4624

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.604  -5.076   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.996  -5.733   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.123  -7.268   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.262  -4.856   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.135  -3.321   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.811  -4.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.600  -3.194   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.434  -1.768   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.850  -0.343   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.163  -2.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.821  -2.547   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      10.462  -1.518   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      11.996  -2.156   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.486  -3.646   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.015  -3.836   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.618  -5.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.334  -6.142   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.451  -7.678   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.933  -5.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.705  -3.872   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.085  -3.169   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.600  -1.286   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.329  -0.100   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.017  -1.247   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.416  -0.626   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.187  -1.691   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.713  -1.245   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   20   24                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   24                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    5   11   21                                             
CONECT   21   20   14   22                                                  
CONECT   22   21   12   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    5   10   25                                             
CONECT   25   24   26                                                       
CONECT   26   25    7   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   66    0
END

View in JSmol

Synonyms

Value	Source
10-Hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-18-yl acetic acid	Generator
10-Hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₇NO₄

Average Mass

369.4610 Da

Monoisotopic Mass

369.19401 Da

IUPAC Name

10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate

Traditional Name

10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC12CC3C(O)C4C5N6CC7(C)CC(=O)CC15C7C6CC24CC3=C

InChI Identifier

InChI=1S/C22H27NO4/c1-10-4-20-8-14-17-19(3)5-12(25)6-21(17)18(23(14)9-19)15(20)16(26)13(10)7-22(20,21)27-11(2)24/h13-18,26H,1,4-9H2,2-3H3

InChI Key

OPSQHQOWJPAFNK-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
Delphinium fissum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Hetisine-type diterpenoid alkaloids

Alternative Parents

Substituents

Hetisine-type diterpenoid alkaloid
Azaspirodecane
Isoindolone
Quinolizidine
Indole or derivatives
Indolizidine
Isoindoline
Isoindole or derivatives
Alkaloid or derivatives
Azepane
Piperidine
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Cyclic ketone
Secondary alcohol
Amino acid or derivatives
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organooxygen compound
Organopnictogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
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	0.78	ALOGPS
logP	-0.01	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.55	ChemAxon
pKa (Strongest Basic)	8.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.46 m³·mol⁻¹	ChemAxon
Polarizability	39.15 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 10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate (NP0287111)

MOL for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

3D MOL for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

3D SDF for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

3D-SDF for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

PDB for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

3D PDB for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

SMILES for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

INCHI for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

Structure for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)

3D Structure for NP0287111 (10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-18-yl acetate)