NP-MRD: Showing NP-Card for (1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate (NP0192768)

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Record Information

Version

2.0

Created at

2022-09-04 10:03:20 UTC

Updated at

2022-09-04 10:03:20 UTC

NP-MRD ID

NP0192768

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate

Description

(1S,13S,16S,17R)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9-trien-16-yl acetate belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. (1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate is found in Brunsvigia orientalis. Based on a literature review very few articles have been published on (1S,13S,16S,17R)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9-trien-16-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042212032D          

 29 33  0  0  1  0            999 V2000
    4.3818   -2.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9428   -1.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6994   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950   -0.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6517    0.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127    0.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170    0.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2604   -0.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0853   -0.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518    0.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6915    0.9195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836    0.3241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1693   -0.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465   -0.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -1.5090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -1.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -0.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7486   -0.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644    0.8731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0632    1.5284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2451    1.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719    0.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    2.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825    0.9795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6994    1.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3802    2.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152    3.1582    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  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
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 17 15  1  1  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -5.2775    0.5155   -0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672    1.1117   -1.3177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318    1.1427   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    0.1230   -0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8710    0.1298    0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6754    1.1933    1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043    2.2375    1.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7307    2.2172    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798    3.3730    0.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801    3.8924    1.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433    3.4050    1.8605 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0743   -0.9648    0.1125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3548   -2.1798    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4738   -2.7213    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3087   -2.0985   -1.2775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327   -1.0293   -1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0414   -1.6135   -1.2808 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3588   -0.5781   -2.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8119   -0.1472   -2.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8724    0.4572   -0.6471 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1407    1.0209   -0.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469    2.3793   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7153    2.9292    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307    3.1155   -0.2311 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172   -0.6032    0.3679 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2538   -1.8075    0.1306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111   -2.4254    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7303   -3.6729    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633   -1.9097    2.2287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0792    1.2782   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6206   -0.2659   -1.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0761    0.0125    0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1922    1.2678    1.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5672    3.5788    2.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0341    4.9870    1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7487   -1.8075    1.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.8650    0.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -3.8230   -0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4723   -2.4494    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -1.3910   -1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -0.7056   -2.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -2.4226   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353   -0.9462   -3.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2302    0.3350   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    0.6677   -2.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5028   -0.9917   -2.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1137    1.2626   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676    2.7489    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7916    3.9864   -0.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3962    2.3447   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451   -0.2536    1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0397   -4.5419    0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -3.8276    1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -3.6705   -0.3776 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
  4 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 12 13  1  1
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 12  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8  3  1  0
  5  4  1  0
 11  7  1  0
 17 15  1  0
 25 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 16 40  1  0
 16 41  1  0
 14 38  1  0
 14 39  1  0
 13 36  1  0
 13 37  1  0
 17 42  1  1
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 23 48  1  0
 23 49  1  0
 23 50  1  0
 25 51  1  1
 28 52  1  0
 28 53  1  0
 28 54  1  0
  6 33  1  0
 10 34  1  0
 10 35  1  0
M  END


  Mrv1652309042212032D          

 29 33  0  0  1  0            999 V2000
    4.3818   -2.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9428   -1.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6994   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950   -0.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6517    0.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127    0.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170    0.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2604   -0.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0853   -0.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518    0.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6915    0.9195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836    0.3241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1693   -0.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465   -0.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -1.5090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -1.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -0.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7486   -0.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644    0.8731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0632    1.5284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2451    1.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719    0.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    2.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825    0.9795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6994    1.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3802    2.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152    3.1582    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  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
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 17 15  1  1  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0192768

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2CN3CC[C@@]4([C@@H]3CC[C@H](OC(C)=O)[C@@H]4OC(C)=O)C2=CC2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO7/c1-11(23)28-15-4-5-17-21(20(15)29-12(2)24)6-7-22(17)9-13-14(21)8-16-19(18(13)25-3)27-10-26-16/h8,15,17,20H,4-7,9-10H2,1-3H3/t15-,17-,20-,21-/m0/s1

> <INCHI_KEY>
DKPKNLDZUOGWFB-OQRYQMPQSA-N

> <FORMULA>
C21H25NO7

> <MOLECULAR_WEIGHT>
403.431

> <EXACT_MASS>
403.163102149

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.02136202587744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13S,16S,17R)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9-trien-16-yl acetate

> <JCHEM_LOGP>
1.1860104133333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.482971092704219

> <JCHEM_POLAR_SURFACE_AREA>
83.53

> <JCHEM_REFRACTIVITY>
100.2001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,16S,17R)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9-trien-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.179  -4.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.227  -3.242   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.772  -1.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.271  -1.429   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.816   0.043   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.864   1.172   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.365   0.830   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.819  -0.642   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.359  -0.665   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.857   0.793   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.624   1.716   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.383   0.605   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.049  -0.165   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.820  -1.688   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.868  -2.817   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.404  -2.701   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.791  -0.817   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.264  -1.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.328   0.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.920   1.630   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.985   2.853   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.457   2.655   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.134   1.233   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.478   3.878   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.447   1.828   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.039   3.250   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.103   4.473   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.576   4.275   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.695   5.895   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7                                                       
CONECT   12    5   13   17   25                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15    4                                                       
CONECT   17   15   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   12   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
(1S,13S,16S,17R)-17-(Acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0,.0,.0,]nonadeca-2,4(8),9-trien-16-yl acetic acid	Generator

Chemical Formula

C₂₁H₂₅NO₇

Average Mass

403.4310 Da

Monoisotopic Mass

403.16310 Da

IUPAC Name

(1S,13S,16S,17R)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9-trien-16-yl acetate

Traditional Name

(1S,13S,16S,17R)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9-trien-16-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=C2CN3CC[C@@]4([C@@H]3CC[C@H](OC(C)=O)[C@@H]4OC(C)=O)C2=CC2=C1OCO2

InChI Identifier

InChI=1S/C21H25NO7/c1-11(23)28-15-4-5-17-21(20(15)29-12(2)24)6-7-22(17)9-13-14(21)8-16-19(18(13)25-3)27-10-26-16/h8,15,17,20H,4-7,9-10H2,1-3H3/t15-,17-,20-,21-/m0/s1

InChI Key

DKPKNLDZUOGWFB-OQRYQMPQSA-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
Brunsvigia orientalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Benzazepine
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Anisole
Alkyl aryl ether
Azepine
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Dicarboxylic acid or derivatives
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Oxacycle
Azacycle
Acetal
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen 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	1.19	ChemAxon
pKa (Strongest Basic)	8.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.2 m³·mol⁻¹	ChemAxon
Polarizability	41.02 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

163088254

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate (NP0192768)

MOL for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

3D MOL for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

3D SDF for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

3D-SDF for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

PDB for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

3D PDB for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

SMILES for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

INCHI for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

Structure for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)

3D Structure for NP0192768 ((1s,13s,16s,17r)-17-(acetyloxy)-9-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-16-yl acetate)