NP-MRD: Showing NP-Card for 11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate (NP0185095)

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Record Information

Version

2.0

Created at

2022-09-04 00:24:14 UTC

Updated at

2022-09-04 00:24:14 UTC

NP-MRD ID

NP0185095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate

Description

11,12,16-Trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]Icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1. 11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate is found in Kopsia singapurensis. 11,12,16-Trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]Icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251515332D          

 32 36  0  0  0  0            999 V2000
    3.4632   -1.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.3325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -0.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981   -0.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989    0.0243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8907    0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4931    0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9986    0.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7491    1.1947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569    1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    2.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5549    2.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5323    1.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7895    1.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180    0.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770   -0.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6560   -0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7780    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829    0.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1421    1.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964    2.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915    2.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4556    2.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2605    2.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2099    3.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050    3.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034   -1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4403   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138   -1.6111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2768   -1.2403    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  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  2  0  0  0  0
 15 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
    6.8592    0.7211    0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5024    0.3941    0.5973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5556    0.5029   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8993    0.9250   -1.5161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1376    0.1443   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2996    0.2843   -1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784   -0.0403   -1.1118 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2567   -0.5618   -2.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009   -2.0053   -2.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -2.5162   -1.2107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826   -1.6167   -0.0735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0773   -2.2510    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -3.4964    1.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1650   -1.6058    2.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587   -2.2843    3.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201   -1.1165   -0.0363 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2212   -0.5824    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106   -0.3565    1.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6309   -0.5129   -0.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9459   -0.7442   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4577   -1.9042   -0.8206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7843    0.2865   -1.1030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    0.0586   -1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1713    0.8212   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    1.1379   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    2.3924   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    3.3395    0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    3.0646    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0017    1.7814    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175    1.7122    0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7631    3.0686    0.9211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516    3.8229    1.1081 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981    0.7051   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0486    1.7526    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5347    0.0134    1.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683    0.6590   -2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6319    0.0582   -2.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9974   -0.4003   -3.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -2.1644   -3.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133   -2.5778   -2.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5505   -3.0989   -1.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -1.8488    3.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314   -2.1141    4.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7103   -3.3557    3.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -1.9309   -0.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631   -1.3711    2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510    0.3700    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1973   -1.3586    1.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0812    0.2844    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7269    0.9886   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5950   -0.7615   -0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0794   -0.1386   -2.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6170    2.5976   -0.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488    4.3401    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4558    3.1963    1.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341    3.2923   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
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 24 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 28  1  0
 28 27  2  0
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 25  7  1  0
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 10 11  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 18  5  1  0
  5  6  2  0
  5  3  1  0
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  3  2  1  0
  2  1  1  0
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 14 15  1  0
 11 19  1  0
 25 24  1  0
 16  7  1  0
 28 29  1  0
  7  6  1  6
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 23 52  1  0
 31 55  1  0
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 27 54  1  0
 26 53  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
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 16 45  1  6
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 17 47  1  0
 18 48  1  0
 18 49  1  0
  6 36  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
M  END


  Mrv1533004251515332D          

 32 36  0  0  0  0            999 V2000
    3.4632   -1.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.3325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -0.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981   -0.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989    0.0243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8907    0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4931    0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9986    0.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7491    1.1947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569    1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    2.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5549    2.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114    1.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5323    1.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7895    1.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180    0.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770   -0.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6560   -0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7780    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829    0.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1421    1.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964    2.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915    2.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4556    2.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2605    2.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2099    3.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050    3.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034   -1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4403   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138   -1.6111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2768   -1.2403    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  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  2  0  0  0  0
 15 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C3OCOC3=CC=C2C23CCNC1(C2CCC(=C3)C(=O)OC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O8/c1-28-18(25)12-4-7-15-21(10-12)8-9-23-22(15,19(26)29-2)24(20(27)30-3)16-13(21)5-6-14-17(16)32-11-31-14/h5-6,10,15,23H,4,7-9,11H2,1-3H3

> <INCHI_KEY>
GNFYUVRTHDXQNH-UHFFFAOYSA-N

> <FORMULA>
C22H24N2O8

> <MOLECULAR_WEIGHT>
444.44

> <EXACT_MASS>
444.153265741

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
44.83417768711607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2,4,9,16-tetraene-11,12,16-tricarboxylate

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
2.167967909333333

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.4679033839860165

> <JCHEM_POLAR_SURFACE_AREA>
112.63000000000001

> <JCHEM_REFRACTIVITY>
109.01509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2,4,9,16-tetraene-11,12,16-tricarboxylate

> <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       6.465  -3.512   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.315  -2.487   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.628  -0.979   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.090  -0.496   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.478   0.045   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.396   1.356   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.520   1.387   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.464   0.170   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.913   0.691   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.865   2.230   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.386   2.660   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.716   4.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.769   4.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.315   2.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.860   3.393   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.474   2.723   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.967   1.269   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.637  -0.118   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.091  -0.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.319   1.923   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.821   1.585   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.865   2.717   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.407   4.187   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.904   4.525   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.451   5.320   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.953   4.982   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.992   6.790   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.489   7.128   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.180  -2.162   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.555  -2.854   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.892  -3.007   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.517  -2.315   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   19                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6   15                                                  
CONECT   15   14   16   20   24                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    5   20   29                                             
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   15                                                       
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   19   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
11,12,16-Trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0,.0,.0,]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylic acid	Generator
11,12,16-Trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylic acid	Generator

Chemical Formula

C₂₂H₂₄N₂O₈

Average Mass

444.4400 Da

Monoisotopic Mass

444.15327 Da

IUPAC Name

11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2,4,9,16-tetraene-11,12,16-tricarboxylate

Traditional Name

11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2,4,9,16-tetraene-11,12,16-tricarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C3OCOC3=CC=C2C23CCNC1(C2CCC(=C3)C(=O)OC)C(=O)OC

InChI Identifier

InChI=1S/C22H24N2O8/c1-28-18(25)12-4-7-15-21(10-12)8-9-23-22(15,19(26)29-2)24(20(27)30-3)16-13(21)5-6-14-17(16)32-11-31-14/h5-6,10,15,23H,4,7-9,11H2,1-3H3

InChI Key

GNFYUVRTHDXQNH-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
Kopsia singapurensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Eburnan-type alkaloids

Sub Class

Not Available

Direct Parent

Eburnan-type alkaloids

Alternative Parents

Substituents

Eburna alkaloid
Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Diazanaphthalene
Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
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	1.5	ALOGPS
logP	2.17	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	3.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.02 m³·mol⁻¹	ChemAxon
Polarizability	44.83 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 11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate (NP0185095)

MOL for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

3D MOL for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

3D SDF for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

3D-SDF for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

PDB for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

3D PDB for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

SMILES for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

INCHI for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

Structure for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)

3D Structure for NP0185095 (11,12,16-trimethyl 6,8-dioxa-11,20-diazapentacyclo[10.5.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icosa-2(10),3,5(9),16-tetraene-11,12,16-tricarboxylate)