NP-MRD: Showing NP-Card for Citrifolinin B epimer b (NP0078398)

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Record Information

Version

2.0

Created at

2022-04-28 23:29:14 UTC

Updated at

2022-04-28 23:29:14 UTC

NP-MRD ID

NP0078398

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citrifolinin B epimer b

Description

Methyl (1'S,2R,2'S,3S,4'S,6'S,7'S)-3-hydroxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxirane-2,5'-tricyclo[4.4.0.0²,⁴]Decan]-9'-ene-10'-carboxylate 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 epimer b is found in Morinda citrifolia . Based on a literature review very few articles have been published on methyl (1'S,2R,2'S,3S,4'S,6'S,7'S)-3-hydroxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxirane-2,5'-tricyclo[4.4.0.0²,⁴]Decan]-9'-ene-10'-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201292D          

 29 33  0  0  1  0            999 V2000
    4.0548    2.5551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8586    1.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0665    1.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4706    2.0937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6669    2.8951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4590    3.1258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6552    3.9271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    4.1578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6436    4.9591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4357    5.1898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0315    4.6192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8352    3.8179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0432    3.5872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8469    2.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4311    3.2473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8236    4.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319    5.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4240    6.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    3.3293    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3357    2.7964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6479    2.0328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8305    2.1442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5013    4.0113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3240    4.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583    4.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702    0.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782    0.4911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661    0.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2582    0.3819    0.0000 C   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
  5 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  6  0  0  0
 20 22  1  6  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  6  0  0  0
 23 25  1  1  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
    6.4343    2.3983    1.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1369    2.2228    1.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7225    1.0567    0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6436    0.2170    0.3272 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764    0.9142   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5247    1.9106    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2234    1.7842   -0.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    0.5554   -0.0696 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6203    0.4852   -0.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7512    0.3879   -0.0033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3829   -0.7782   -0.2708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7300   -0.8143   -0.3327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1269   -2.0793   -1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5116   -2.1592   -1.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4355    0.3315   -0.9373 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3752    0.8720   -0.0438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    1.4753   -1.3234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9134    1.2689   -2.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5542    1.6366   -0.1981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2760    1.8898    0.9637 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366   -0.5650   -0.4954 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8999   -0.2400   -0.7300 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5631   -1.5506   -0.4891 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0269   -2.5413   -1.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6264   -2.5836   -0.1052 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4007   -1.7994    0.3292 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1603   -2.4191    0.3707 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161   -2.1046    1.5592 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2722   -1.2434    2.4746 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8781    3.3019    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1132    1.5521    1.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4653    2.5800    2.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    2.8097    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132    0.5049    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    0.3886    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1291   -0.9892    0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7491   -2.9869   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446   -1.9332   -2.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9118   -1.9105   -0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0355    0.0383   -1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2471    0.5001    0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1147    2.4055   -1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    0.3191   -2.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    2.4784   -0.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5966    2.8316    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -0.8902   -1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.0210   -1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208   -1.6792   -0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9726   -3.4339    0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1629   -3.0621    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946   -1.3322    2.5995 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  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 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 27 28  1  0
 28 29  1  0
 22  5  1  0
 25 23  1  0
 28 26  1  0
 19 10  1  0
 26 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  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  6
 18 43  1  0
 19 44  1  6
 20 45  1  0
 21 46  1  6
 22 47  1  6
 23 48  1  1
 25 49  1  1
 28 50  1  1
 29 51  1  0
M  END


  Mrv1652304292201292D          

 29 33  0  0  1  0            999 V2000
    4.0548    2.5551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8586    1.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0665    1.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4706    2.0937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6669    2.8951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4590    3.1258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6552    3.9271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    4.1578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6436    4.9591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4357    5.1898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0315    4.6192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8352    3.8179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0432    3.5872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8469    2.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4311    3.2473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8236    4.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319    5.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4240    6.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    3.3293    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3357    2.7964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6479    2.0328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8305    2.1442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5013    4.0113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3240    4.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583    4.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702    0.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782    0.4911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661    0.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2582    0.3819    0.0000 C   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
  5 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  6  0  0  0
 20 22  1  6  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  6  0  0  0
 23 25  1  1  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078398

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1[C@@H]1O[C@@H]1[C@]21O[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O12/c1-24-13(22)4-3-25-14(7-6(4)11-12(27-11)17(7)16(23)29-17)28-15-10(21)9(20)8(19)5(2-18)26-15/h3,5-12,14-16,18-21,23H,2H2,1H3/t5-,6-,7-,8-,9+,10-,11+,12+,14+,15+,16+,17-/m1/s1

> <INCHI_KEY>
UXNDFLAYYHSFII-CYXPCIHLSA-N

> <FORMULA>
C17H22O12

> <MOLECULAR_WEIGHT>
418.351

> <EXACT_MASS>
418.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.5604911980008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.47

> <JCHEM_LOGP>
-2.820042719000001

> <ALOGPS_LOGS>
-0.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.275884542092165

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.419897324524104

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601930304

> <JCHEM_POLAR_SURFACE_AREA>
180.2

> <JCHEM_REFRACTIVITY>
85.47959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,2R,2'S,3S,4'S,6'S,7'S)-3-hydroxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxirane-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-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       7.569   4.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.203   3.274   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.724   2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.612   3.908   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.978   5.404   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.457   5.835   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.823   7.331   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.302   7.761   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.668   9.257   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.147   9.688   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.259   8.622   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.892   7.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.414   6.696   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.048   5.200   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      12.005   6.062   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.737   9.053   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.513  11.183   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.991  11.614   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.669   6.215   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.493   5.220   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.076   3.794   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.550   4.002   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.802   7.488   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.338   7.602   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.415   8.157   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.358   1.347   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.879   0.917   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.470   0.282   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.949   0.713   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18                                                       
CONECT   18   17                                                            
CONECT   19    5   20   23   24                                             
CONECT   20   19   21   22                                                  
CONECT   21   20    4   22                                                  
CONECT   22   21   20                                                       
CONECT   23   19   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26    3   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1's,2R,2's,3S,4's,6's,7's)-3-hydroxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxirane-2,5'-tricyclo[4.4.0.0,]decan]-9'-ene-10'-carboxylic acid	Generator

Chemical Formula

C₁₇H₂₂O₁₂

Average Mass

418.3510 Da

Monoisotopic Mass

418.11113 Da

IUPAC Name

methyl (1'S,2R,2'S,3S,4'S,6'S,7'S)-3-hydroxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxirane-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

Traditional Name

methyl (1'S,2R,2'S,3S,4'S,6'S,7'S)-3-hydroxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxirane-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1[C@@H]1O[C@@H]1[C@]21O[C@@H]1O

InChI Identifier

InChI=1S/C17H22O12/c1-24-13(22)4-3-25-14(7-6(4)11-12(27-11)17(7)16(23)29-17)28-15-10(21)9(20)8(19)5(2-18)26-15/h3,5-12,14-16,18-21,23H,2H2,1H3/t5-,6-,7-,8-,9+,10-,11+,12+,14+,15+,16+,17-/m1/s1

InChI Key

UXNDFLAYYHSFII-CYXPCIHLSA-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

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
Oxane
Monosaccharide
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
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	-1.5	ALOGPS
logP	-2.8	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Acidic)	11.42	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.48 m³·mol⁻¹	ChemAxon
Polarizability	38.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162821242

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Citrifolinin B epimer b (NP0078398)

MOL for NP0078398 (Citrifolinin B epimer b)

3D MOL for NP0078398 (Citrifolinin B epimer b)

3D SDF for NP0078398 (Citrifolinin B epimer b)

3D-SDF for NP0078398 (Citrifolinin B epimer b)

PDB for NP0078398 (Citrifolinin B epimer b)

3D PDB for NP0078398 (Citrifolinin B epimer b)

SMILES for NP0078398 (Citrifolinin B epimer b)

INCHI for NP0078398 (Citrifolinin B epimer b)

Structure for NP0078398 (Citrifolinin B epimer b)

3D Structure for NP0078398 (Citrifolinin B epimer b)