NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0302837)

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Record Information

Version

2.0

Created at

2022-09-10 16:40:09 UTC

Updated at

2022-09-10 16:40:09 UTC

NP-MRD ID

NP0302837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Description

CHEMBL601640 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. (2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol is found in Aristolochia manshuriensis. Based on a literature review very few articles have been published on CHEMBL601640.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218402D          

 32 37  0  0  1  0            999 V2000
   -4.0998   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -0.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2163   -1.7566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4504   -2.0631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3328   -2.8797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5668   -3.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -2.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360   -1.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876   -1.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784   -1.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -2.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525   -2.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -3.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7310   -4.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -3.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -4.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8052   -3.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600   -2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -2.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3993   -1.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236   -1.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -2.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402   -4.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3503   -5.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158   -4.8799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9812   -3.3898    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8637   -4.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472   -3.0833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3956   -3.5934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8647   -2.2667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6307   -1.9602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  7 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  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 11 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 14 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END

     RDKit          3D

 51 56  0  0  0  0  0  0  0  0999 V2000
   -5.0076    0.5699    3.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619    1.4509    2.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4193    0.7692    0.7633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1240    0.3243    1.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597   -0.1093   -0.0848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1438   -0.3249    0.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.2990   -0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    1.1954   -1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    1.7792   -2.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    1.4701   -1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710    0.5710   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810   -0.0304    0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3020   -0.9455    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581   -1.2912    1.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6094   -0.6821    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7784   -1.1237    1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376   -0.5835    0.9621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8785    0.3289   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6738    0.7683   -0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348    0.2223   -0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9482    1.6659   -1.6373 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2556    2.1529   -1.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744    1.0171   -0.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4164   -2.0680    2.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3070   -2.7387    3.3561 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1074   -2.1448    2.5518 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -1.4303   -0.4549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4889   -2.0944   -1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5727   -1.0490   -0.8458 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2911   -2.0902   -1.3747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2158   -0.4659    0.4078 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5597   -0.1924    0.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9368    1.0781    3.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9320    1.9577    1.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2411    2.2578    2.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4154    1.4515   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998    0.5886   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256    1.4729   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    2.4837   -2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9588    1.9511   -2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460   -1.3829    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8632   -0.8984    1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562    3.0151   -0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652    2.3498   -2.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7040   -3.6191    3.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073   -2.0390    0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0530   -1.4718   -2.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4806   -0.1822   -1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4046   -1.9610   -2.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0368   -1.2149    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0083   -1.0571    0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 26  1  0
 26 24  2  0
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 23 18  1  0
 18 17  1  0
 20 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  5 27  1  0
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 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  3  1  0
  8  7  2  0
 11 12  1  0
 15 14  2  0
 18 19  2  0
 17 16  2  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  6
  5 37  1  6
 13 41  1  0
 25 45  1  0
 22 43  1  0
 22 44  1  0
 17 42  1  0
 10 40  1  0
  9 39  1  0
  8 38  1  0
 27 46  1  1
 28 47  1  0
 29 48  1  6
 30 49  1  0
 31 50  1  1
 32 51  1  0
M  END


  Mrv1652309102218402D          

 32 37  0  0  1  0            999 V2000
   -4.0998   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -0.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2163   -1.7566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4504   -2.0631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3328   -2.8797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5668   -3.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -2.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360   -1.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876   -1.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784   -1.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -2.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525   -2.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -3.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7310   -4.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -3.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -4.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8052   -3.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600   -2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -2.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3993   -1.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236   -1.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -2.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402   -4.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3503   -5.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158   -4.8799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9812   -3.3898    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8637   -4.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472   -3.0833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3956   -3.5934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8647   -2.2667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6307   -1.9602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  7 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  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 11 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 14 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0302837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C3C=C4N=C(O)C5=C4C(=C4OCOC4=C5)C3=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H19NO9/c24-6-14-17(25)18(26)19(27)22(32-14)31-12-3-1-2-8-9(12)4-11-15-10(21(28)23-11)5-13-20(16(8)15)30-7-29-13/h1-5,14,17-19,22,24-27H,6-7H2,(H,23,28)/t14-,17-,18+,19-,22-/m1/s1

> <INCHI_KEY>
BMZVZDXTSLWMHR-MAEOEUOPSA-N

> <FORMULA>
C22H19NO9

> <MOLECULAR_WEIGHT>
441.392

> <EXACT_MASS>
441.105981196

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.396489365544014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0^{2,6}.0^{8,19}.0^{13,18}]nonadeca-1,6,8(19),9,11,13,15,17-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
0.8498950420000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200112884953976

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.590159851103966

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1250165846148218

> <JCHEM_POLAR_SURFACE_AREA>
150.43

> <JCHEM_REFRACTIVITY>
109.08120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0^{2,6}.0^{8,19}.0^{13,18}]nonadeca-1,6,8(19),9,11,13,15,17-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

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HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0      -7.653  -1.183   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.223  -1.755   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.004  -3.279   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.574  -3.851   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.355  -5.375   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.925  -5.948   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.714  -4.995   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.934  -3.471   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.724  -2.519   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.706  -3.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.926  -4.615   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.285  -5.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.065  -7.092   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.365  -7.664   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.575  -6.712   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.855  -7.569   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.236  -6.889   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.339  -5.352   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.059  -4.495   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.356  -5.187   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.479  -3.014   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.017  -2.955   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.549  -4.400   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.435  -9.050   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.387 -10.261   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       1.896  -9.109   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -5.565  -6.328   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.345  -7.852   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.995  -5.755   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.205  -6.708   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -7.214  -4.231   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.644  -3.659   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15   11                                                  
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   16   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   14                                                       
CONECT   27    5   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₁₉NO₉

Average Mass

441.3920 Da

Monoisotopic Mass

441.10598 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0^{2,6}.0^{8,19}.0^{13,18}]nonadeca-1,6,8(19),9,11,13,15,17-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0^{2,6}.0^{8,19}.0^{13,18}]nonadeca-1,6,8(19),9,11,13,15,17-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C3C=C4N=C(O)C5=C4C(=C4OCOC4=C5)C3=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C22H19NO9/c24-6-14-17(25)18(26)19(27)22(32-14)31-12-3-1-2-8-9(12)4-11-15-10(21(28)23-11)5-13-20(16(8)15)30-7-29-13/h1-5,14,17-19,22,24-27H,6-7H2,(H,23,28)/t14-,17-,18+,19-,22-/m1/s1

InChI Key

BMZVZDXTSLWMHR-MAEOEUOPSA-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 manshuriensis	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
Phenolic glycoside
Phenanthrene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Naphthalene
Isoindolone
Benzodioxole
Isoindole or derivatives
Indole or derivatives
Benzenoid
Monosaccharide
Oxane
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Primary alcohol
Organopnictogen compound
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	0.85	ChemAxon
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	150.43 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	109.08 m³·mol⁻¹	ChemAxon
Polarizability	43.4 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

24653469

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46232738

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0302837)

MOL for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0302837 ((2s,3r,4s,5s,6r)-2-({9-hydroxy-3,5-dioxa-10-azapentacyclo[9.7.1.0²,⁶.0⁸,¹⁹.0¹³,¹⁸]nonadeca-1(19),2(6),7,9,11,13(18),14,16-octaen-14-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)