NP-MRD: Showing NP-Card for 4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate (NP0216017)

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Record Information

Version

2.0

Created at

2022-09-05 15:49:32 UTC

Updated at

2022-09-05 15:49:33 UTC

NP-MRD ID

NP0216017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate

Description

4-Methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]Icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. 4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate is found in Clivia miniata. 4-Methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]Icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241517142D          

 29 33  0  0  0  0            999 V2000
    4.5960   -2.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7788   -2.1832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -2.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4647   -2.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -0.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503    0.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936    1.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109    1.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -0.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -1.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  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
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 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  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
  5 29  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    7.2702   -2.0875    0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1156   -1.2917   -0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2269   -0.7360   -1.5569 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9126   -1.2210    0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -0.3879   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9829    0.1758   -1.3901 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -0.2131    0.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5635    0.5590   -0.1446 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3097    1.7868    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0522    2.3556    0.2277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4049    3.6692    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574    3.5525    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2461    2.2103    0.6733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    2.5398    2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0940    1.4061    0.6388 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9649    0.3424   -0.3793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9832   -0.6814   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2318   -0.6413    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686   -1.6373   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -2.7169   -0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6504   -2.7610   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6925   -1.7557   -1.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671   -1.9321   -1.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225   -2.8998   -2.6984 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254   -0.8998   -1.6599 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3902   -0.3114   -0.3389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0110   -3.5273   -0.9510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9065   -3.1277    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4730   -1.8055    0.3476 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8768   -2.9335    0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9869   -1.4775    0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8166   -2.5654   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1365   -0.7796    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5354   -2.2477    0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419    0.9973   -1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415    2.4841    0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765    1.5035    1.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1206    2.3704   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872    4.4604    0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3540    3.8964    1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8325    3.5043   -0.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953    4.3443    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7837    2.7991    2.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047    1.7710    2.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3008    3.4427    1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8052    1.0771    1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    0.8940   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4744    0.2113    0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3660   -3.5980   -2.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901   -1.1224    0.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6554   -3.8013    0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9560   -3.1938   -0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  8 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  2  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 29  1  0
 29 28  1  0
 28 27  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 15 10  1  0
 16 26  1  0
 17 22  1  0
 27 20  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 12 41  1  0
 12 42  1  0
 11 39  1  0
 11 40  1  0
 10 38  1  6
  9 36  1  0
  9 37  1  0
  8 35  1  6
  4 33  1  0
  4 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 26 50  1  1
 21 49  1  0
 28 51  1  0
 28 52  1  0
 18 48  1  0
 16 47  1  6
 15 46  1  1
M  END


  Mrv1533004241517142D          

 29 33  0  0  0  0            999 V2000
    4.5960   -2.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7788   -2.1832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -2.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4647   -2.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -0.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503    0.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936    1.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109    1.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -0.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -1.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  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
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 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  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
  5 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2CC(OC(=O)CC(C)=O)C3OC(=O)C4=CC5=C(OCO5)C=C4C3C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H23NO7/c1-10(23)5-17(24)28-16-6-11-3-4-22(2)19(11)18-12-7-14-15(27-9-26-14)8-13(12)21(25)29-20(16)18/h7-8,11,16,18-20H,3-6,9H2,1-2H3

> <INCHI_KEY>
FVUFQVCGJLVWOQ-UHFFFAOYSA-N

> <FORMULA>
C21H23NO7

> <MOLECULAR_WEIGHT>
401.415

> <EXACT_MASS>
401.147452085

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.49808252097826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.4477285746374007

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.0060670909907

> <JCHEM_PKA_STRONGEST_BASIC>
8.288926951018144

> <JCHEM_POLAR_SURFACE_AREA>
91.37

> <JCHEM_REFRACTIVITY>
99.8187

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       8.579  -4.286   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.054  -4.075   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.987  -5.186   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.601  -4.514   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.811  -2.988   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.819  -1.811   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.342  -0.363   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.349   0.815   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.833   0.544   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.310  -0.905   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.841   1.721   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.675   1.450   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.668   2.627   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.199   0.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.858  -0.092   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.381   1.357   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.897   1.628   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.420   3.076   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.890   0.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.406   0.722   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.399  -0.456   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.938  -0.506   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.366  -1.985   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.091  -2.849   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.875  -1.904   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.359  -2.175   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.367  -0.998   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.851  -1.269   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.327  -2.717   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   19   28                                                  
CONECT   28   27   15   29                                                  
CONECT   29   28    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
4-Methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0,.0,.0,]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoic acid	Generator
4-Methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoic acid	Generator

Chemical Formula

C₂₁H₂₃NO₇

Average Mass

401.4150 Da

Monoisotopic Mass

401.14745 Da

IUPAC Name

4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate

Traditional Name

4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate

CAS Registry Number

Not Available

SMILES

CN1CCC2CC(OC(=O)CC(C)=O)C3OC(=O)C4=CC5=C(OCO5)C=C4C3C12

InChI Identifier

InChI=1S/C21H23NO7/c1-10(23)5-17(24)28-16-6-11-3-4-22(2)19(11)18-12-7-14-15(27-9-26-14)8-13(12)21(25)29-20(16)18/h7-8,11,16,18-20H,3-6,9H2,1-2H3

InChI Key

FVUFQVCGJLVWOQ-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
Clivia miniata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Homolycorine-type amaryllidaceae alkaloids

Direct Parent

Homolycorine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Homolycorine skeleton
2-benzopyran
Isochromane
Benzopyran
Benzodioxole
Indole or derivatives
Fatty acid ester
Aralkylamine
Beta-keto acid
Dicarboxylic acid or derivatives
Fatty acyl
Keto acid
Benzenoid
N-alkylpyrrolidine
1,3-dicarbonyl compound
Pyrrolidine
Amino acid or derivatives
Ketone
Lactone
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Azacycle
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.42	ALOGPS
logP	1.45	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	8.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	91.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.82 m³·mol⁻¹	ChemAxon
Polarizability	41.5 Å³	ChemAxon
Number of Rings	5	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 4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate (NP0216017)

MOL for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

3D MOL for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

3D SDF for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

3D-SDF for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

PDB for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

3D PDB for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

SMILES for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

INCHI for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

Structure for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)

3D Structure for NP0216017 (4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl 3-oxobutanoate)