NP-MRD: Showing NP-Card for 3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one (NP0227186)

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Record Information

Version

2.0

Created at

2022-09-06 06:26:27 UTC

Updated at

2022-09-06 06:26:27 UTC

NP-MRD ID

NP0227186

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one

Description

3-[(2Z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxy-2H-pyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. 3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one is found in Jacobaea cannabifolia. Based on a literature review very few articles have been published on 3-[(2Z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxy-2H-pyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062208262D          

 27 29  0  0  0  0            999 V2000
    1.3222    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.6509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    4.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538   -1.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032   -0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4582    0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832    0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7681    1.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4325    1.9141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5381   -0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3227   -0.5465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707   -0.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707   -1.6015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    2.8337   -2.1338    0.8134 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3865   -0.9863    0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    0.1557    1.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8643    1.3176    0.4770 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1763    1.5393   -0.2781 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4425    0.4282   -1.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3152    1.7775    0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4566    2.0045   -0.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887    1.2311   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5011    0.5495    0.0792 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2793    1.3855    1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734   -0.7788    0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968   -1.8452    0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -3.1964    0.7497 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -3.9632    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103   -5.3375    0.8583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -3.2152    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -1.9078    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -0.7963   -0.3710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3626    0.1427    0.5814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    0.6918    0.2914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6093    2.1665    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8160    2.6522   -0.8992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2253   -0.1088   -0.8054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0656    0.3781   -2.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4637   -1.4294   -0.5773 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9539   -1.9286    0.6128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7461    2.1647    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    2.4244   -0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6626   -0.3707   -0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1003    2.7506    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706    0.9542    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9689    1.1782   -0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386    2.2563   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    0.7477   -1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316    0.6882   -0.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4882    2.3203    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2071   -6.0127    0.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100   -3.5747   -0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138   -0.4295   -1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2306    0.4893    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2881    2.6327    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6777    2.4723   -0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201    3.5902   -1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3140   -0.2713   -0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298    0.8305   -2.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875   -2.0956   -1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4408   -1.5380    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 12  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
 18 13  1  0
 26 19  1  0
  8 33  1  0
  7 31  1  0
  7 32  1  0
  5 29  1  6
  6 30  1  0
  4 28  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  6
 21 41  1  1
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  1
 25 46  1  0
 26 47  1  6
 27 48  1  0
M  END


  Mrv1652309062208262D          

 27 29  0  0  0  0            999 V2000
    1.3222    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.6509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    4.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538   -1.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032   -0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4582    0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832    0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7681    1.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4325    1.9141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5381   -0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3227   -0.5465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707   -0.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707   -1.6015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227186

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(O)C1CC(O)\C(=C2\N=C(O)C=C2C2OC(CO)C(O)C2O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO10/c18-3-7(21)8-2-6(20)11(16(25)27-8)12-5(1-10(22)17-12)15-14(24)13(23)9(4-19)26-15/h1,6-9,13-15,18-21,23-24H,2-4H2,(H,17,22)/b12-11-

> <INCHI_KEY>
CAFXXGBBONAMAZ-QXMHVHEDSA-N

> <FORMULA>
C16H21NO10

> <MOLECULAR_WEIGHT>
387.341

> <EXACT_MASS>
387.11654588

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.1488329220511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2Z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxy-2H-pyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one

> <JCHEM_LOGP>
-4.175437400666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.657630019332164

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.027821694108128

> <JCHEM_PKA_STRONGEST_BASIC>
2.2942817568203493

> <JCHEM_POLAR_SURFACE_AREA>
189.49999999999997

> <JCHEM_REFRACTIVITY>
87.58630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2Z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       2.468   1.425   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.802   3.735   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.136   6.045   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.802   6.815   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.469   6.815   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.469   8.355   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.469   3.735   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.803   1.425   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.890  -1.020   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.366  -2.485   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.460  -3.731   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.906  -2.485   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.381  -1.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.846  -0.544   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.322   0.920   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.862   0.920   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.767   2.166   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.141   3.573   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.338  -0.544   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.802  -1.020   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.092  -1.449   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.092  -2.989   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    2   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₁NO₁₀

Average Mass

387.3410 Da

Monoisotopic Mass

387.11655 Da

IUPAC Name

3-[(2Z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxy-2H-pyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one

Traditional Name

3-[(2Z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one

CAS Registry Number

Not Available

SMILES

OCC(O)C1CC(O)\C(=C2\N=C(O)C=C2C2OC(CO)C(O)C2O)C(=O)O1

InChI Identifier

InChI=1S/C16H21NO10/c18-3-7(21)8-2-6(20)11(16(25)27-8)12-5(1-10(22)17-12)15-14(24)13(23)9(4-19)26-15/h1,6-9,13-15,18-21,23-24H,2-4H2,(H,17,22)/b12-11-

InChI Key

CAFXXGBBONAMAZ-QXMHVHEDSA-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
Jacobaea cannabifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Delta valerolactone
Delta_valerolactone
Monosaccharide
Oxane
Oxolane
Pyrroline
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Alcohol
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-4.2	ChemAxon
pKa (Strongest Acidic)	5.03	ChemAxon
pKa (Strongest Basic)	2.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	189.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.59 m³·mol⁻¹	ChemAxon
Polarizability	37.15 Å³	ChemAxon
Number of Rings	3	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

10160827

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11988360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one (NP0227186)

MOL for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

3D MOL for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

3D SDF for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

3D-SDF for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

PDB for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

3D PDB for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

SMILES for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

INCHI for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

Structure for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)

3D Structure for NP0227186 (3-[(2z)-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrrol-2-ylidene]-6-(1,2-dihydroxyethyl)-4-hydroxyoxan-2-one)