NP-MRD: Showing NP-Card for 2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0288540)

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Record Information

Version

2.0

Created at

2022-09-09 18:17:17 UTC

Updated at

2022-09-09 18:17:17 UTC

NP-MRD ID

NP0288540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-({11,14-Dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-1,3,5,7,9(16),10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system. 2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol is found in Aristolochia elegans. 2-({11,14-Dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-1,3,5,7,9(16),10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514172D          

 32 36  0  0  0  0            999 V2000
    2.9748   -1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902   -1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6209   -2.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 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
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  2  0  0  0  0
 31 32  1  0  0  0  0
  7 32  2  0  0  0  0
 11 32  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    1.4933   -3.5867    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670   -2.5614    1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -1.9920    1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.6908    1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582   -3.8857    2.1546 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5053   -2.2043    1.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6758   -1.0079    0.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5601   -0.3389    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278    0.8212   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7940    1.6008   -0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987    1.1636   -0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657    1.9738   -0.9941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.5972   -0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1272    0.4215   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    0.0506    0.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6131    0.6354   -0.0905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3829   -0.1334   -0.9596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6054    0.4267   -1.2497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4974    1.7268   -2.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8468    1.5460   -3.2366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4372    0.5911   -0.0037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6551    1.1755   -0.2993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024    1.5038    0.9555 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4051    1.5352    2.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3391    0.9465    1.2002 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3712   -0.1032    2.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239   -0.4074    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2083   -0.0326    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -0.8094    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2494    0.9309   -0.4846 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8179   -0.2102    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0122   -0.5144    0.3182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326   -3.8530    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1921   -4.4342    0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6085   -3.1404   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8699   -4.4067    2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3915   -2.7288    1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9874    2.5390   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6798    2.9028   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    2.2725   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4617    1.6056   -0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1462   -0.2907   -1.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5526    2.0300   -2.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0641    2.5468   -1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658    2.2538   -3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6095   -0.4226    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2379    0.5904   -0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026    2.5145    0.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3917    0.6119    2.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7363    1.7650    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2369   -0.9873    1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6265   -1.2574    0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7757    1.7204   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 29  2  0
 29  8  1  0
  8  7  2  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
  7 31  1  0
 31 32  2  0
 31 30  1  0
 30  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14 27  1  0
 27 28  2  0
  4  3  1  0
 28 11  1  0
 28 29  1  0
  9  8  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  6 37  1  0
  5 36  1  0
 30 53  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 16 41  1  6
 18 42  1  6
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  1
 22 47  1  0
 23 48  1  6
 24 49  1  0
 25 50  1  1
 26 51  1  0
 27 52  1  0
M  END


  Mrv1533004231514172D          

 32 36  0  0  0  0            999 V2000
    2.9748   -1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902   -1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6209   -2.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 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
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  2  0  0  0  0
 31 32  1  0  0  0  0
  7 32  2  0  0  0  0
 11 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C3=C(C=C1O)C(=O)NC3=CC1=CC=C(OC3OC(CO)C(O)C(O)C3O)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C22H21NO9/c1-30-20-13(25)6-11-15-12(23-21(11)29)4-8-2-3-9(5-10(8)16(15)20)31-22-19(28)18(27)17(26)14(7-24)32-22/h2-6,14,17-19,22,24-28H,7H2,1H3,(H,23,29)

> <INCHI_KEY>
OELDBESAYZDHRI-UHFFFAOYSA-N

> <FORMULA>
C22H21NO9

> <MOLECULAR_WEIGHT>
443.408

> <EXACT_MASS>
443.12163126

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.36542422754125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-15-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
0.03796831666666689

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.129338335775923

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.960025215728352

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343694531

> <JCHEM_POLAR_SURFACE_AREA>
157.94

> <JCHEM_REFRACTIVITY>
111.00330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-15-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       5.553  -3.091   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.088  -3.567   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.159  -4.519   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.655   2.016   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.122  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.455  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.789  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.264  -1.030   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30                                                       
CONECT   30   29   13   31                                                  
CONECT   31   30    3   32                                                  
CONECT   32   31    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁NO₉

Average Mass

443.4080 Da

Monoisotopic Mass

443.12163 Da

IUPAC Name

14-hydroxy-15-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

Traditional Name

14-hydroxy-15-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

CAS Registry Number

Not Available

SMILES

COC1=C2C3=C(C=C1O)C(=O)NC3=CC1=CC=C(OC3OC(CO)C(O)C(O)C3O)C=C21

InChI Identifier

InChI=1S/C22H21NO9/c1-30-20-13(25)6-11-15-12(23-21(11)29)4-8-2-3-9(5-10(8)16(15)20)31-22-19(28)18(27)17(26)14(7-24)32-22/h2-6,14,17-19,22,24-28H,7H2,1H3,(H,23,29)

InChI Key

OELDBESAYZDHRI-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
Aristolochia elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aristolactams

Sub Class

Not Available

Direct Parent

Aristolactams

Alternative Parents

Substituents

Aristolactam
Phenanthrol
Phenolic glycoside
Phenanthrene
Hexose monosaccharide
Glycosyl compound
2-naphthol
O-glycosyl compound
Naphthalene
Isoindolone
Indole
Indole or derivatives
Isoindole
Isoindole or derivatives
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monosaccharide
Oxane
Heteroaromatic compound
Pyrrole
Lactam
Secondary alcohol
Acetal
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
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	0.61	ALOGPS
logP	0.038	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	157.94 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111 m³·mol⁻¹	ChemAxon
Polarizability	43.37 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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 2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0288540)

MOL for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0288540 (2-({11,14-dihydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)