NP-MRD: Showing NP-Card for (20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol (NP0203666)

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Record Information

Version

2.0

Created at

2022-09-04 23:11:01 UTC

Updated at

2022-09-04 23:11:01 UTC

NP-MRD ID

NP0203666

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol

Description

(12AR,13S)-3,7-Dimethoxy-6,13-dihydroxy-9,10,11,12,12a,13-hexahydro-9a-aza-9aH-cyclopenta[b]triphenylene belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene. (20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol is found in Tylophora asthmatica. Based on a literature review very few articles have been published on (12aR,13S)-3,7-Dimethoxy-6,13-dihydroxy-9,10,11,12,12a,13-hexahydro-9a-aza-9aH-cyclopenta[b]triphenylene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201112D          

 27 31  0  0  1  0            999 V2000
    5.6202   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -2.5921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399   -4.2891    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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 21  1  1  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
   -4.2174   -4.9154    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777   -3.5195    0.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9831   -2.8200    0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8222   -3.5403    0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -2.8180    0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6122   -1.4502    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6002   -0.7787    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.6013    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5938    1.3193    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6520    2.6890    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8165    3.4335    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8438    4.8066    0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265    5.6257   -0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832    2.7309    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773    3.4370    0.4331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706    1.3252    0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944    0.6187    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -0.7612    0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0044   -1.4461    0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8647    1.3475   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6536    0.4015   -1.0264 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8558    0.9472   -1.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9648   -0.0481   -1.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2256   -1.2748   -0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0169   -0.6509   -0.1103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8445   -1.5906    0.0124 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9725   -2.3457    1.2051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454   -5.3314    1.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9343   -5.3468   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2592   -5.2131    1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7812   -4.6180    0.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2879   -3.3680    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2459    3.2518   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0595    5.1969   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0040    6.6062   -0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956    5.8195    0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    2.9235    0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415    0.8796    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9594   -0.9708    0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3248    1.5621    0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258    2.2771   -0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7571    1.0126   -2.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1092    1.9582   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5598   -0.2548   -2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6087    0.3794   -0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9174   -1.9169   -1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992   -1.8186    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2802   -0.2613    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -2.2630   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -1.8281    1.8821 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  5  1  0
  5  6  2  0
  6 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  1  0
 14 11  2  0
 11 12  1  0
 12 13  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7 26  1  0
 26 27  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 19  3  1  0
  9 17  1  0
 20  8  1  0
  7  6  1  0
 21 25  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
 19 39  1  0
 16 38  1  0
 15 37  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 10 33  1  0
 26 49  1  6
 27 50  1  0
 25 48  1  1
 24 46  1  0
 24 47  1  0
 23 44  1  0
 23 45  1  0
 22 42  1  0
 22 43  1  0
 20 40  1  0
 20 41  1  0
M  END


  Mrv1652309052201112D          

 27 31  0  0  1  0            999 V2000
    5.6202   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -2.5921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399   -4.2891    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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 21  1  1  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0203666

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=C1)C1=CC(O)=C(OC)C=C1C1=C2[C@H](O)[C@H]2CCCN2C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H23NO4/c1-26-12-5-6-13-14(8-12)15-9-19(24)20(27-2)10-16(15)17-11-23-7-3-4-18(23)22(25)21(13)17/h5-6,8-10,18,22,24-25H,3-4,7,11H2,1-2H3/t18-,22-/m1/s1

> <INCHI_KEY>
CMFIDYCYVJWPPL-XMSQKQJNSA-N

> <FORMULA>
C22H23NO4

> <MOLECULAR_WEIGHT>
365.429

> <EXACT_MASS>
365.162708225

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.478607406546466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(20R,21S)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaene-10,21-diol

> <JCHEM_LOGP>
2.705286296768011

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.877555581061053

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.707670276292719

> <JCHEM_PKA_STRONGEST_BASIC>
8.267590315011239

> <JCHEM_POLAR_SURFACE_AREA>
62.16

> <JCHEM_REFRACTIVITY>
104.13669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(20R,21S)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaene-10,21-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      10.491  -7.913   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.968  -6.465   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.452  -6.194   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.459  -7.371   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.943  -7.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.420  -5.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904  -5.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.381  -3.932   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.374  -2.755   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850  -1.307   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.843  -0.129   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.320   1.319   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.804   1.590   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.359  -0.400   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.352   0.777   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.882  -1.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.889  -3.026   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.413  -4.474   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.929  -4.746   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.865  -3.661   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       0.872  -4.839   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -0.667  -4.889   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.095  -6.368   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.179  -7.232   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.395  -6.287   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.911  -6.558   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.434  -8.006   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    9   18                                                  
CONECT   18   17    6   19                                                  
CONECT   19   18    3                                                       
CONECT   20    8   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25    7   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₃NO₄

Average Mass

365.4290 Da

Monoisotopic Mass

365.16271 Da

IUPAC Name

(20R,21S)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaene-10,21-diol

Traditional Name

(20R,21S)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaene-10,21-diol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=C1)C1=CC(O)=C(OC)C=C1C1=C2[C@H](O)[C@H]2CCCN2C1

InChI Identifier

InChI=1S/C22H23NO4/c1-26-12-5-6-13-14(8-12)15-9-19(24)20(27-2)10-16(15)17-11-23-7-3-4-18(23)22(25)21(13)17/h5-6,8-10,18,22,24-25H,3-4,7,11H2,1-2H3/t18-,22-/m1/s1

InChI Key

CMFIDYCYVJWPPL-XMSQKQJNSA-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
Tylophora asthmatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthroindolizidines

Direct Parent

Phenanthroindolizidines

Alternative Parents

Substituents

Phenanthroindolizidine
Phenanthrol
2-naphthol
Naphthalene
Tetrahydroisoquinoline
Indolizidine
Anisole
Phenol ether
Aralkylamine
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Organoheterocyclic compound
Azacycle
Ether
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Amine
Organooxygen compound
Hydrocarbon derivative
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	2.71	ChemAxon
pKa (Strongest Acidic)	9.71	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.14 m³·mol⁻¹	ChemAxon
Polarizability	40.48 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

102271561

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol (NP0203666)

MOL for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

3D MOL for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

3D SDF for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

3D-SDF for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

PDB for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

3D PDB for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

SMILES for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

INCHI for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

Structure for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)

3D Structure for NP0203666 ((20r,21s)-5,11-dimethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaene-10,21-diol)