NP-MRD: Showing NP-Card for methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate (NP0213791)

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Record Information

Version

2.0

Created at

2022-09-05 12:52:59 UTC

Updated at

2022-09-05 12:53:00 UTC

NP-MRD ID

NP0213791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate

Description

PericosineE belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate is found in Periconia byssoides. Based on a literature review very few articles have been published on PericosineE.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052214532D          

 27 28  0  0  1  0            999 V2000
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0934   -0.8963    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  1  0  0  0
 11 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
    5.9748    2.1717    1.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1451    1.2866    0.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7785    1.4506    0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    2.4075    1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9512    0.5429   -0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815   -0.4909   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -1.3618   -1.6897 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0343   -0.7316   -2.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476   -1.7689   -0.7542 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6236   -2.6277   -1.4329 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483   -0.5847   -0.1484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5492   -0.4228   -0.6169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -0.4782    0.3480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4291    0.6615    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765    1.8446   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087    2.8033   -0.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4189    2.0278   -1.3540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3383    3.1728   -2.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718    0.5367    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466   -0.7462    2.1645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5465   -0.8597    2.8625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1834   -1.9594    1.3100 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4008   -2.5555    0.9815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4433   -1.6676    0.0540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3853   -1.2284   -0.9015 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4795    0.7163   -0.3824 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9851    1.8129    0.9533 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8630    3.2149    0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7815    2.0509    2.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0312    1.8842    1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5506   -0.6374   -0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724   -2.2729   -2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8891   -1.3271   -3.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9359   -2.3654    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865   -3.3668   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.7230    0.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -0.6225    1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036    3.5604   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0615    3.9710   -1.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902    2.9453   -3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1239    1.2860    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5235   -0.6282    2.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5889   -1.7967    3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6115   -2.7251    1.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748   -3.3714    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160   -2.5053   -0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2484   -1.6969   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738    1.1740   -1.3314 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
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 20 19  1  0
 19 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 11 26  1  0
 26 27  1  0
 26  5  1  0
 14 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  7 32  1  6
  8 33  1  0
  9 34  1  1
 10 35  1  0
 11 36  1  1
 13 37  1  1
 24 46  1  6
 25 47  1  0
 22 44  1  1
 23 45  1  0
 20 42  1  1
 21 43  1  0
 19 41  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 26 48  1  6
M  END


  Mrv1652309052214532D          

 27 28  0  0  1  0            999 V2000
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0934   -0.8963    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  1  0  0  0
 11 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0213791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C[C@H](O)[C@H](O)[C@H](O[C@@H]2[C@H](O)[C@H](O)[C@H](O)C=C2C(=O)OC)[C@H]1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C16H21ClO10/c1-25-15(23)5-3-8(19)11(21)14(9(5)17)27-13-6(16(24)26-2)4-7(18)10(20)12(13)22/h3-4,7-14,18-22H,1-2H3/t7-,8+,9+,10-,11+,12-,13+,14-/m1/s1

> <INCHI_KEY>
ASEVULJAKVHVDT-UQHZVBSCSA-N

> <FORMULA>
C16H21ClO10

> <MOLECULAR_WEIGHT>
408.78

> <EXACT_MASS>
408.0823246

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.31866296821992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3S,4S,5S,6S)-6-chloro-3,4-dihydroxy-5-{[(1S,4R,5R,6R)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate

> <JCHEM_LOGP>
-1.843390240999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.112239412872047

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.528564546173666

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3824808364810224

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
89.41470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3S,4S,5S,6S)-6-chloro-3,4-dihydroxy-5-{[(1S,4R,5R,6R)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27 Cl   UNK     0       2.041  -1.673   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   26                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   13   25                                                  
CONECT   25   24                                                            
CONECT   26   11    5   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₁ClO₁₀

Average Mass

408.7800 Da

Monoisotopic Mass

408.08232 Da

IUPAC Name

methyl (3S,4S,5S,6S)-6-chloro-3,4-dihydroxy-5-{[(1S,4R,5R,6R)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate

Traditional Name

methyl (3S,4S,5S,6S)-6-chloro-3,4-dihydroxy-5-{[(1S,4R,5R,6R)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C[C@H](O)[C@H](O)[C@H](O[C@@H]2[C@H](O)[C@H](O)[C@H](O)C=C2C(=O)OC)[C@H]1Cl

InChI Identifier

InChI=1S/C16H21ClO10/c1-25-15(23)5-3-8(19)11(21)14(9(5)17)27-13-6(16(24)26-2)4-7(18)10(20)12(13)22/h3-4,7-14,18-22H,1-2H3/t7-,8+,9+,10-,11+,12-,13+,14-/m1/s1

InChI Key

ASEVULJAKVHVDT-UQHZVBSCSA-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
Periconia byssoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Shikimic acids and derivatves

Alternative Parents

Substituents

Shikimic acid or derivatives
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Polyol
Hydrocarbon derivative
Alkyl chloride
Organic oxide
Alkyl halide
Organohalogen compound
Organochloride
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-1.8	ChemAxon
pKa (Strongest Acidic)	12.53	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.41 m³·mol⁻¹	ChemAxon
Polarizability	37.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

21195936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24744627

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate (NP0213791)

MOL for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

3D MOL for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

3D SDF for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

3D-SDF for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

PDB for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

3D PDB for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

SMILES for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

INCHI for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

Structure for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)

3D Structure for NP0213791 (methyl (3s,4s,5s,6s)-6-chloro-3,4-dihydroxy-5-{[(1s,4r,5r,6r)-4,5,6-trihydroxy-2-(methoxycarbonyl)cyclohex-2-en-1-yl]oxy}cyclohex-1-ene-1-carboxylate)