NP-MRD: Showing NP-Card for methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate (NP0251277)

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Record Information

Version

2.0

Created at

2022-09-07 14:25:42 UTC

Updated at

2022-09-07 14:25:42 UTC

NP-MRD ID

NP0251277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate

Description

Asitrilobin C belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Asitrilobin C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Asitrilobin C has been detected, but not quantified in, fruits. methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate is found in Annona purpurea and Annona mucosa. This could make asitrilobin C a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308272D          

 26 29  0  0  0  0            999 V2000
    3.4432   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7295    1.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2710    1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2489    1.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8212    1.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    2.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5558    0.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795    3.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.1562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -1.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    1.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  6  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 20  7  1  0  0  0  0
 20  8  1  0  0  0  0
 20 11  1  0  0  0  0
 20 17  1  0  0  0  0
 21  9  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 13  2  0  0  0  0
 23 19  2  0  0  0  0
 24  1  1  0  0  0  0
 24 15  1  0  0  0  0
 25  2  1  0  0  0  0
 25 18  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
M  END

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    6.0556    0.1741   -1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608   -0.4003   -0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7214    0.2800   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7436    1.5434   -0.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5362   -0.3676    0.1324 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.8274    0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122   -2.3369    1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2153   -1.8187    0.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -2.5128    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -1.8804    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2892   -2.5678    0.0437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316   -3.9370    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1092   -0.5316   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2454    0.1082   -0.6682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0767    0.7227    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169    0.1554   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867   -0.4936    0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3682    0.3963    0.4681 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9856    1.4306   -0.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5320    1.5659   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2133    1.9956   -1.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796    3.0532   -1.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741    3.8367   -0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9223    4.8774   -0.4028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5307    3.4646    0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    2.3935    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4701   -0.4854   -1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9634    1.2194   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7937    0.1175   -0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563   -2.1620    0.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4718   -2.3116   -0.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5895   -3.4221    1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7498   -1.8580    2.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474   -3.5542    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -3.9797    1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3520   -4.3522    0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5722   -4.4791   -0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7546   -0.0450    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4188    1.1724    1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6466    1.5756   -0.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166    0.8549    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4744    2.3986   -0.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2067    0.9866   -1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    1.4237   -2.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992    3.3965   -2.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6879    4.0669    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    2.1133    1.7413 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 18  5  1  0
 26 20  1  0
 17  8  1  0
 20 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 18 41  1  1
 19 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 25 46  1  0
 26 47  1  0
M  END


  Mrv0541 05061308272D          

 26 29  0  0  0  0            999 V2000
    3.4432   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7295    1.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2710    1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2489    1.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8212    1.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    2.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5558    0.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795    3.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.1562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -1.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    1.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  6  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 20  7  1  0  0  0  0
 20  8  1  0  0  0  0
 20 11  1  0  0  0  0
 20 17  1  0  0  0  0
 21  9  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 13  2  0  0  0  0
 23 19  2  0  0  0  0
 24  1  1  0  0  0  0
 24 15  1  0  0  0  0
 25  2  1  0  0  0  0
 25 18  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC31C=CC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO5/c1-24-15-10-12-6-9-21(19(23)26-3)14-11-20(7-4-13(22)5-8-20)17(16(12)14)18(15)25-2/h4-5,7-8,10,14H,6,9,11H2,1-3H3

> <INCHI_KEY>
RRWYPLCSLKEVAO-UHFFFAOYSA-N

> <FORMULA>
C20H21NO5

> <MOLECULAR_WEIGHT>
355.3844

> <EXACT_MASS>
355.141972787

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.80127521846113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.303073835666666

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.553680786538101

> <JCHEM_POLAR_SURFACE_AREA>
65.07000000000001

> <JCHEM_REFRACTIVITY>
98.16479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.427  -1.828   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.095   2.019   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.239   2.788   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.917   4.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.198   3.364   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.119   3.430   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.400   2.047   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.457   4.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.904   0.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.860   2.080   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -1.570  -0.290   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       4.255   6.031   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.237  -0.292   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.094  -2.599   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.094   0.479   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.905   2.019   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4    7   13                                                       
CONECT    5    8   13                                                       
CONECT    6    9   12                                                       
CONECT    7    4   20                                                       
CONECT    8    5   20                                                       
CONECT    9    6   21                                                       
CONECT   10   12   15                                                       
CONECT   11   14   20                                                       
CONECT   12    6   10   16                                                  
CONECT   13    4    5   22                                                  
CONECT   14   11   16   21                                                  
CONECT   15   10   18   24                                                  
CONECT   16   12   14   17                                                  
CONECT   17   16   18   20                                                  
CONECT   18   15   17   25                                                  
CONECT   19   21   23   26                                                  
CONECT   20    7    8   11   17                                             
CONECT   21    9   14   19                                                  
CONECT   22   13                                                            
CONECT   23   19                                                            
CONECT   24    1   15                                                       
CONECT   25    2   18                                                       
CONECT   26    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
Methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₁NO₅

Average Mass

355.3844 Da

Monoisotopic Mass

355.14197 Da

IUPAC Name

methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate

Traditional Name

methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC31C=CC(=O)C=C1

InChI Identifier

InChI=1S/C20H21NO5/c1-24-15-10-12-6-9-21(19(23)26-3)14-11-20(7-4-13(22)5-8-20)17(16(12)14)18(15)25-2/h4-5,7-8,10,14H,6,9,11H2,1-3H3

InChI Key

RRWYPLCSLKEVAO-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
Annona purpurea	LOTUS Database	35616633
Rollinia mucosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.05	ALOGPS
logP	2.3	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.16 m³·mol⁻¹	ChemAxon
Polarizability	36.8 Å³	ChemAxon
Number of Rings	4	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

HMDB0035436

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014117

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

131751753

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate (NP0251277)

MOL for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

3D MOL for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

3D SDF for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

3D-SDF for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

PDB for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

3D PDB for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

SMILES for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

INCHI for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

Structure for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)

3D Structure for NP0251277 (methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate)