NP-MRD: Showing NP-Card for (5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol (NP0325702)

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Record Information

Version

2.0

Created at

2022-09-12 06:39:59 UTC

Updated at

2022-09-12 06:40:00 UTC

NP-MRD ID

NP0325702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol

Description

Javaberine A belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. (5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol is found in Talinum paniculatum. Based on a literature review very few articles have been published on Javaberine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122208402D          

 31 35  0  0  1  0            999 V2000
   -2.4304   -5.9505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -5.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -5.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -4.5473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5401   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -3.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -2.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9705   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009   -2.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -4.3914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -6.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -6.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -7.1978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  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  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 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
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  1  0  0  0
  7 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  2  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    2.1097   -5.3489    2.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1232   -4.0426    1.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.0642    2.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065   -1.7786    1.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1505   -1.3999    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612   -0.0165    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2166    0.2047   -1.0537 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3092    1.6551   -1.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4511    2.1226   -2.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932    3.4505   -2.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584    3.8995   -3.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5503    4.3218   -2.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6412    5.6745   -2.6145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929    3.8649   -1.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2641    2.5256   -1.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0273    2.1569   -0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807    0.8318    0.1219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0433    0.3338    0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4480    0.8139    1.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417    0.3417    2.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0182    0.8561    3.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3891   -0.5768    1.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864   -1.0443    2.3614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9529   -1.0421    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857   -0.6063   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2560   -1.0535   -1.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -1.2354   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495   -0.0348   -0.7869 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833   -2.3766    0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699   -3.6790    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8245   -4.6373    0.0922 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -5.5481    2.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6181   -3.3395    2.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361   -1.0460    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997    0.2496   -0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9536    0.7361    0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5522   -0.3637   -1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015    1.4830   -2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8189    4.8665   -3.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572    6.2848   -2.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4068    4.5810   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    2.8729    0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8103    1.9480   -1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448    1.1145    0.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8722    1.5415    2.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8683    0.5261    4.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234   -1.7214    1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424   -1.7665    0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348   -0.2640   -2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7467   -1.9980   -1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3710   -1.4960   -2.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5975   -2.1004   -0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622   -2.1107   -0.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8232   -5.5659    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  2  0
 24 22  1  0
 22 23  1  0
 22 20  2  0
 20 21  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 12  1  0
 12 13  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  5 29  1  0
 29 30  2  0
 30 31  1  0
 30  2  1  0
  8  7  1  0
 17 28  1  0
  8 15  1  0
 18 25  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  6
 27 51  1  0
 27 52  1  0
 26 49  1  0
 26 50  1  0
 24 48  1  0
 23 47  1  0
 21 46  1  0
 19 45  1  0
 17 44  1  1
 16 42  1  0
 16 43  1  0
 14 41  1  0
 13 40  1  0
 11 39  1  0
  9 38  1  0
 29 53  1  0
 31 54  1  0
M  END


  Mrv1652309122208402D          

 31 35  0  0  1  0            999 V2000
   -2.4304   -5.9505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -5.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -5.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -4.5473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5401   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -3.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -2.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9705   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009   -2.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -4.3914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -6.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -6.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -7.1978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  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  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 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
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  1  0  0  0
  7 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  2  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C[C@H]2N3CCC4=CC(O)=C(O)C=C4[C@@H]3CC3=CC(O)=C(O)C=C23)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H23NO6/c26-19-2-1-12(6-20(19)27)5-17-16-11-24(31)22(29)9-14(16)7-18-15-10-23(30)21(28)8-13(15)3-4-25(17)18/h1-2,6,8-11,17-18,26-31H,3-5,7H2/t17-,18+/m1/s1

> <INCHI_KEY>
FAGGKCPHMLDUDN-MSOLQXFVSA-N

> <FORMULA>
C24H23NO6

> <MOLECULAR_WEIGHT>
421.449

> <EXACT_MASS>
421.152537465

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.492549583532494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,12bS)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5H-6-azatetraphene-2,3,10,11-tetrol

> <JCHEM_LOGP>
4.030169245333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.415292743501407

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.937305350942184

> <JCHEM_PKA_STRONGEST_BASIC>
5.588032457939244

> <JCHEM_POLAR_SURFACE_AREA>
124.62

> <JCHEM_REFRACTIVITY>
116.42589999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5R,12bS)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5H-6-azatetraphene-2,3,10,11-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.537 -11.108   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.024 -10.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.520  -9.361   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.008  -9.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000 -10.234   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.512  -9.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.016  -8.488   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.008  -7.324   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.504  -7.615   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.512  -6.451   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.024  -6.742   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.008  -4.996   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.016  -3.832   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.504  -4.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.512  -5.869   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.024  -5.578   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.033  -6.742   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.545  -6.451   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.049  -4.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.561  -4.705   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.065  -3.250   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.569  -5.869   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.082  -5.578   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.065  -7.324   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.553  -7.615   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.049  -9.070   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.537  -9.361   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       3.529  -8.197   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -0.504 -11.690   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.016 -11.981   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.520 -13.436   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   17    7                                                  
CONECT   29    5   30                                                       
CONECT   30   29    2   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₃NO₆

Average Mass

421.4490 Da

Monoisotopic Mass

421.15254 Da

IUPAC Name

(5R,12bS)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5H-6-azatetraphene-2,3,10,11-tetrol

Traditional Name

(5R,12bS)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5H-6-azatetraphene-2,3,10,11-tetrol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C[C@H]2N3CCC4=CC(O)=C(O)C=C4[C@@H]3CC3=CC(O)=C(O)C=C23)C=C1O

InChI Identifier

InChI=1S/C24H23NO6/c26-19-2-1-12(6-20(19)27)5-17-16-11-24(31)22(29)9-14(16)7-18-15-10-23(30)21(28)8-13(15)3-4-25(17)18/h1-2,6,8-11,17-18,26-31H,3-5,7H2/t17-,18+/m1/s1

InChI Key

FAGGKCPHMLDUDN-MSOLQXFVSA-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
Talinum paniculatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Tetrahydroprotoberberine skeleton
Protoberberine skeleton
Benzylisoquinoline
Tetrahydroisoquinoline
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.03	ChemAxon
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	5.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	124.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.43 m³·mol⁻¹	ChemAxon
Polarizability	43.49 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

C00027398

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

122224813

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol (NP0325702)

MOL for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

3D MOL for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

3D SDF for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

3D-SDF for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

PDB for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

3D PDB for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

SMILES for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

INCHI for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

Structure for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)

3D Structure for NP0325702 ((5r,12bs)-5-[(3,4-dihydroxyphenyl)methyl]-7,8,12b,13-tetrahydro-5h-6-azatetraphene-2,3,10,11-tetrol)