NP-MRD: Showing NP-Card for Citrifolinin B (NP0085369)

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Record Information

Version

2.0

Created at

2022-04-29 05:55:14 UTC

Updated at

2022-04-29 05:55:14 UTC

NP-MRD ID

NP0085369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citrifolinin B

Description

Tudoside belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Citrifolinin B is found in Morinda citrifolia and Pentas lanceolata. Citrifolinin B was first documented in 2007 (PMID: 17824664). Based on a literature review very few articles have been published on Tudoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207552D          

 33 36  0  0  1  0            999 V2000
   -3.2460    1.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539    1.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8580    1.9059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0543    2.7072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8464    2.9380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584    3.2779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6547    4.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664    3.0472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0705    3.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701    2.2458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3220    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182    1.2138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3103    0.9831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0118    1.4174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5066    2.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188    2.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076    1.9880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415    0.8845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2374    1.4551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.1208    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3547   -0.7038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1467    0.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.1818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7855   -0.5946    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1070   -1.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111   -1.7608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074   -2.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991   -1.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186   -0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.6432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659    1.6752    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 14 17  1  1  0  0  0
 14 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 18 22  1  0  0  0  0
 13 23  1  1  0  0  0
 13 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 26 31  2  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 10 33  1  0  0  0  0
  3 33  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    4.9085    3.4906   -2.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8191    2.6290   -2.5937 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8865    1.4985   -1.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807    1.1790   -1.3092 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7206    0.6757   -1.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    1.0612   -2.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4677    0.2883   -1.9766 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284   -0.5216   -0.7430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8468   -1.0048   -0.7417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458   -0.3318    0.1766 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3271   -1.1225    1.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -0.3101    1.9815 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4262   -1.0221    3.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3180   -2.0356    2.9845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0990    0.3813    1.2570 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9646    1.0225    2.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4498    1.3391    0.2807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3365    2.1527   -0.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6218    0.4914   -0.6778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8491    1.3828   -1.4074 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737   -1.4285   -0.8575 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -0.5184   -0.7863 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8225   -0.1891    0.7011 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6701   -0.9725    1.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523   -1.2766    1.3736 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9134   -2.3043    0.3157 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1639   -2.9095   -0.0384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -3.3291    0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371   -3.1312    1.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7533    3.9552   -3.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8986    4.3163   -2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8822    2.9525   -2.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    1.9755   -2.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6080    0.2441    0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647    0.4220    0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304    0.4679    2.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9029   -0.2480    3.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5527   -1.3915    3.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3024   -2.7737    3.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6535   -0.4369    0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5907    1.5574    1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7026    1.9313    0.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6382    1.8072   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602   -0.1413   -1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1137    1.4557   -2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812   -1.9733   -1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7009   -1.1683   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8202    0.8805    0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7206   -1.3317    2.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0759   -3.2962   -0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2827   -4.3893    0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 26 28  1  0
 28 29  2  0
 26 21  1  0
 21  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  5 22  1  0
 25 23  1  0
 22 21  1  0
 22 23  1  0
 19 10  1  0
 23 48  1  6
 25 49  1  1
 27 50  1  0
 28 51  1  0
 21 46  1  6
  8 34  1  1
 10 35  1  1
 12 36  1  1
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  6
 16 41  1  0
 17 42  1  1
 18 43  1  0
 19 44  1  6
 20 45  1  0
  6 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 22 47  1  6
M  END


  Mrv1652304292207552D          

 33 36  0  0  1  0            999 V2000
   -3.2460    1.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539    1.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8580    1.9059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0543    2.7072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8464    2.9380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584    3.2779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6547    4.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664    3.0472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0705    3.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701    2.2458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3220    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182    1.2138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3103    0.9831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0118    1.4174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5066    2.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188    2.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076    1.9880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415    0.8845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2374    1.4551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.1208    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3547   -0.7038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1467    0.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.1818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7855   -0.5946    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1070   -1.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111   -1.7608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074   -2.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991   -1.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186   -0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.6432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659    1.6752    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 14 17  1  1  0  0  0
 14 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 18 22  1  0  0  0  0
 13 23  1  1  0  0  0
 13 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 26 31  2  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 10 33  1  0  0  0  0
  3 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12O[C@]1([H])[C@@](O)(C=O)[C@@]1([H])[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C(C(=O)OC)[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O12/c1-25-14(23)5-3-26-15(8-7(5)12-13(28-12)17(8,24)4-19)29-16-11(22)10(21)9(20)6(2-18)27-16/h3-4,6-13,15-16,18,20-22,24H,2H2,1H3/t6-,7-,8-,9-,10+,11-,12+,13+,15+,16+,17-/m1/s1

> <INCHI_KEY>
DAHBOVPFKVSERQ-HWCJXECGSA-N

> <FORMULA>
C17H22O12

> <MOLECULAR_WEIGHT>
418.351

> <EXACT_MASS>
418.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.83404288392536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2S,4S,5R,6S,7S)-5-formyl-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0^{2,4}]dec-9-ene-10-carboxylate

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-3.3036748463333336

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.330651950697447

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.64767851426061

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601980406

> <JCHEM_POLAR_SURFACE_AREA>
184.73999999999995

> <JCHEM_REFRACTIVITY>
86.9769

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2S,4S,5R,6S,7S)-5-formyl-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0^{2,4}]dec-9-ene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -6.059   2.923   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.581   2.493   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.468   3.558   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.835   5.054   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.313   5.484   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.722   6.119   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.089   7.614   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.244   5.688   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.132   6.753   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.878   4.192   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.601   3.762   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.967   2.266   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.446   1.835   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.755   2.646   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.812   3.863   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.395   5.289   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.868   3.711   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.931   1.651   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       6.043   2.716   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       4.348   0.226   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       4.395  -1.314   0.000  0.00  0.00           H+0
HETATM   22  O   UNK     0       5.874   0.433   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       2.812   0.339   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       3.333  -1.110   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       1.700  -0.726   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.066  -2.222   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.954  -3.287   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.320  -4.783   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.545  -2.652   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.221  -0.295   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.145   1.201   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.990   3.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14   23   24                                             
CONECT   14   13   15   17   18                                             
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   14   19   20   22                                             
CONECT   19   18                                                            
CONECT   20   18   21   22   24                                             
CONECT   21   20                                                            
CONECT   22   20   18                                                       
CONECT   23   13                                                            
CONECT   24   13   20   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27                                                            
CONECT   31   26   32                                                       
CONECT   32   31   12                                                       
CONECT   33   10    3                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O₁₂

Average Mass

418.3510 Da

Monoisotopic Mass

418.11113 Da

IUPAC Name

methyl (1S,2S,4S,5R,6S,7S)-5-formyl-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0^{2,4}]dec-9-ene-10-carboxylate

Traditional Name

methyl (1S,2S,4S,5R,6S,7S)-5-formyl-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0^{2,4}]dec-9-ene-10-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@]1([H])[C@@](O)(C=O)[C@@]1([H])[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C(C(=O)OC)[C@@]21[H]

InChI Identifier

InChI=1S/C17H22O12/c1-25-14(23)5-3-26-15(8-7(5)12-13(28-12)17(8,24)4-19)29-16-11(22)10(21)9(20)6(2-18)27-16/h3-4,6-13,15-16,18,20-22,24H,2H2,1H3/t6-,7-,8-,9-,10+,11-,12+,13+,15+,16+,17-/m1/s1

InChI Key

DAHBOVPFKVSERQ-HWCJXECGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Morinda citrifolia	Plant	KNApSAcK
Pentas lanceolata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Acetal
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Aldehyde
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-1.3	ALOGPS
logP	-3.3	ChemAxon
logS	-0.6	ALOGPS
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	184.74 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	86.98 m³·mol⁻¹	ChemAxon
Polarizability	37.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055204

Chemspider ID

28284473

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23643645

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Schripsema J, Caprini GP, van der Heijden R, Bino R, de Vos R, Dagnino D: Iridoids from Pentas lanceolata. J Nat Prod. 2007 Sep;70(9):1495-8. doi: 10.1021/np070116+. Epub 2007 Sep 8. [PubMed:17824664 ]

Showing NP-Card for Citrifolinin B (NP0085369)

MOL for NP0085369 (Citrifolinin B)

3D MOL for NP0085369 (Citrifolinin B)

3D SDF for NP0085369 (Citrifolinin B)

3D-SDF for NP0085369 (Citrifolinin B)

PDB for NP0085369 (Citrifolinin B)

3D PDB for NP0085369 (Citrifolinin B)

SMILES for NP0085369 (Citrifolinin B)

INCHI for NP0085369 (Citrifolinin B)

Structure for NP0085369 (Citrifolinin B)

3D Structure for NP0085369 (Citrifolinin B)