NP-MRD: Showing NP-Card for 17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione (NP0283779)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 11:11:19 UTC

Updated at

2022-09-09 11:11:19 UTC

NP-MRD ID

NP0283779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione

Description

17-Hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]Icosa-1(19),2(6),7,12(20),13,15,17-heptaene-9,10-dione belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. 17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione is found in Aristolochia tuberosa. 17-Hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]Icosa-1(19),2(6),7,12(20),13,15,17-heptaene-9,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241516582D          

 34 39  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1854    2.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 34  2  0  0  0  0
 24 34  1  0  0  0  0
M  END

     RDKit          3D

 53 58  0  0  0  0  0  0  0  0999 V2000
   -0.8077   -3.5302    2.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996   -2.5399    1.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5986   -2.0269    1.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738   -2.4740    1.9833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -0.8833    0.6703 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9653   -0.3755    0.3526 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5468    0.1012    1.5265 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7384    0.7376    1.3498 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6256    2.0928    0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728    2.6962    0.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7641   -0.1040    0.6550 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9087   -0.2869    1.4489 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289   -1.4574    0.2425 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0982   -1.9706   -0.7212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528   -1.3932   -0.3340 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9810   -1.1160   -1.6977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388   -0.3104    0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    0.7712   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6436    1.3430   -1.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618    2.4294   -2.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811    3.0280   -2.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    2.5303   -2.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0341    3.1496   -2.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313    1.4358   -1.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.8498   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9535   -0.2417   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1936   -0.7562    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2753   -1.8574    1.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1323   -2.4055    1.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8770   -1.9173    1.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979   -0.8284    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6311   -2.1616    1.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3668   -1.0895    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4756   -0.4007   -0.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996    0.4689   -0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1340    0.9470    2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    2.7899    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    2.0832   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9455    3.1912   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1230    0.4535   -0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8891    0.3788    2.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3139   -2.1252    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9666   -2.2509   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4159   -2.4189   -0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856   -1.2734   -2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468    1.2171   -0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771    2.8130   -2.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5395    3.8762   -3.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4369    2.8740   -3.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0244    1.1144   -1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762   -3.2580    2.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7091   -0.3924    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2280   -1.5268    0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  0
  2 30  1  0
 30 31  2  0
 31 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 34  1  0
 34 33  1  0
 33 32  1  0
 32 28  1  0
 28 29  2  0
 11  8  1  0
 17  5  1  0
 25 19  1  0
 28 27  1  0
 29 30  1  0
 26 31  1  0
 10 39  1  0
  9 37  1  0
  9 38  1  0
  8 36  1  1
  6 35  1  6
 15 44  1  6
 16 45  1  0
 13 42  1  1
 14 43  1  0
 11 40  1  6
 12 41  1  0
 18 46  1  0
 20 47  1  0
 21 48  1  0
 23 49  1  0
 24 50  1  0
 33 52  1  0
 33 53  1  0
 29 51  1  0
M  END


  Mrv1533004241516582D          

 34 39  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1854    2.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 34  2  0  0  0  0
 24 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(C(O)C(O)C1O)N1C(=O)C(=O)C2=C3C1=CC1=CC=C(O)C=C1C3=C1OCOC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C23H19NO10/c25-6-14-18(28)19(29)20(30)23(34-14)24-12-3-8-1-2-9(26)4-10(8)16-15(12)11(17(27)22(24)31)5-13-21(16)33-7-32-13/h1-5,14,18-20,23,25-26,28-30H,6-7H2

> <INCHI_KEY>
AQLKJEZWZUVOGC-UHFFFAOYSA-N

> <FORMULA>
C23H19NO10

> <MOLECULAR_WEIGHT>
469.402

> <EXACT_MASS>
469.100895816

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
45.49401637327586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
-0.2997308599999997

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.436763843164933

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.33157796518277

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9802659316009876

> <JCHEM_POLAR_SURFACE_AREA>
166.21999999999997

> <JCHEM_REFRACTIVITY>
111.90119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

> <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  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.655   6.126   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.186   6.287   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.813   4.880   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   33                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23   25   34                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   12   34                                                  
CONECT   34   33   17   24                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₁₉NO₁₀

Average Mass

469.4020 Da

Monoisotopic Mass

469.10090 Da

IUPAC Name

17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

Traditional Name

17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

CAS Registry Number

Not Available

SMILES

OCC1OC(C(O)C(O)C1O)N1C(=O)C(=O)C2=C3C1=CC1=CC=C(O)C=C1C3=C1OCOC1=C2

InChI Identifier

InChI=1S/C23H19NO10/c25-6-14-18(28)19(29)20(30)23(34-14)24-12-3-8-1-2-9(26)4-10(8)16-15(12)11(17(27)22(24)31)5-13-21(16)33-7-32-13/h1-5,14,18-20,23,25-26,28-30H,6-7H2

InChI Key

AQLKJEZWZUVOGC-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 tuberosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Phenanthrol
Phenanthrene
Benzoquinoline
Hexose monosaccharide
2-naphthol
Isoquinolone
Dihydroquinolone
Glycosyl compound
N-glycosyl compound
Naphthalene
Isoquinoline
Dihydroquinoline
Quinoline
Benzodioxole
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Benzenoid
Monosaccharide
Pyridine
Oxane
Heteroaromatic compound
Lactam
Secondary alcohol
Polyol
Oxacycle
Azacycle
Organoheterocyclic compound
Acetal
Primary alcohol
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
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	0.34	ALOGPS
logP	-0.3	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	166.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	111.9 m³·mol⁻¹	ChemAxon
Polarizability	45.49 Å³	ChemAxon
Number of Rings	6	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 17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione (NP0283779)

MOL for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

3D MOL for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

3D SDF for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

3D-SDF for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

PDB for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

3D PDB for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

SMILES for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

INCHI for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

Structure for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)

3D Structure for NP0283779 (17-hydroxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14(19),15,17-heptaene-9,10-dione)