NP-MRD: Showing NP-Card for methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate (NP0251711)

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Record Information

Version

2.0

Created at

2022-09-07 14:58:57 UTC

Updated at

2022-09-07 14:58:57 UTC

NP-MRD ID

NP0251711

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate

Description

Jiadifenin belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate is found in Illicium jiadifengpi. methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate was first documented in 2012 (PMID: 22926836). Based on a literature review a small amount of articles have been published on Jiadifenin (PMID: 29148748) (PMID: 26785051) (PMID: 23526661) (PMID: 35228379).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216582D          

 24 27  0  0  1  0            999 V2000
   -1.4276   -1.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376   -0.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3238   -0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002   -1.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339   -0.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353    0.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -0.4204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    0.1886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7171    0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    0.8752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5307    1.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    2.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7753    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    2.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315    1.1427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3876    0.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3991    1.6719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0578    2.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    2.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    1.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035    0.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.9472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2692    0.2733    0.0000 O   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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  8 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    4.4187   -0.0999    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631   -0.3317    0.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0705    0.0286    1.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4578    0.5594    2.6950 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360   -0.2055    1.3176 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0936    0.2571    2.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4415   -1.5323    1.0540 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141   -1.7283   -0.2819 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7001   -0.4596   -0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2806    0.5313    0.0547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2023    0.6604   -0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325    1.9295    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3483    2.7393    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111    3.9283    0.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.8882   -0.0900 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3761    2.2462   -1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0116   -0.5246   -0.3739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9007   -0.3520   -1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9584   -0.7405    0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549   -1.7953    1.4987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372   -2.6566    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7983   -3.9169    0.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -1.7939   -0.5202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5538   -2.4242   -1.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -1.0545    1.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5681    0.3708    2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9241    0.5282    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -0.0624    3.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6680   -2.6251   -0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.5343   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1495   -0.3046   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5306    2.3920   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5909    2.0639    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099    1.5832   -2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4812    2.3567   -1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933    3.2646   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5170    0.5455   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813   -0.3877   -2.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5964   -1.2293   -1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1249    0.1641    1.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -1.1053    0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8670   -2.1732   -2.4213 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  1  1
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12 11  2  0
 11 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  6
 10  5  1  0
 10 11  1  1
 23 17  1  0
 23  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 15 33  1  1
 16 34  1  0
 16 35  1  0
 16 36  1  0
 12 32  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 24 42  1  0
M  END


  Mrv1652309072216582D          

 24 27  0  0  1  0            999 V2000
   -1.4276   -1.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376   -0.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3238   -0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002   -1.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339   -0.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353    0.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -0.4204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    0.1886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7171    0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    0.8752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5307    1.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    2.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7753    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    2.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315    1.1427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3876    0.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3991    1.6719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0578    2.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    2.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    1.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035    0.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.9472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2692    0.2733    0.0000 O   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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  8 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0251711

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)O[C@@H]2C[C@]11[C@@H](C)C(=O)C=C1[C@]1(C)COC(=O)[C@]21O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O8/c1-7-8(17)4-9-13(2)6-23-11(18)15(13,20)10-5-14(7,9)16(21,24-10)12(19)22-3/h4,7,10,20-21H,5-6H2,1-3H3/t7-,10+,13-,14+,15+,16?/m0/s1

> <INCHI_KEY>
RVLZTXZDKYFFMN-LRCVSGIZSA-N

> <FORMULA>
C16H18O8

> <MOLECULAR_WEIGHT>
338.312

> <EXACT_MASS>
338.10016754

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.041268866514095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,6R,10R,11R)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0^{1,5}.0^{6,10}]tetradec-4-ene-13-carboxylate

> <JCHEM_LOGP>
-0.10927250566666633

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.040437396352297

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.221492231732666

> <JCHEM_PKA_STRONGEST_BASIC>
-4.434657411216265

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000003

> <JCHEM_REFRACTIVITY>
76.73329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,6R,10R,11R)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0^{1,5}.0^{6,10}]tetradec-4-ene-13-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.665  -3.169   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.124  -1.727   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.604  -1.475   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.374  -2.665   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.063  -0.033   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.559   0.332   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.386  -0.785   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.526   0.352   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.339   1.075   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.138   1.634   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.991   3.055   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.006   4.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.447   3.685   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.741   4.519   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.366   2.133   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.590   1.199   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.612   3.121   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.975   4.523   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.671   4.239   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.061   3.577   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.862   2.050   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.980   0.991   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.348   1.768   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.236   0.510   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   10                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11   15                                             
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16                                                  
CONECT   16   15                                                            
CONECT   17   11   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    8   17   24                                             
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₈

Average Mass

338.3120 Da

Monoisotopic Mass

338.10017 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)O[C@@H]2C[C@]11[C@@H](C)C(=O)C=C1[C@]1(C)COC(=O)[C@]21O

InChI Identifier

InChI=1S/C16H18O8/c1-7-8(17)4-9-13(2)6-23-11(18)15(13,20)10-5-14(7,9)16(21,24-10)12(19)22-3/h4,7,10,20-21H,5-6H2,1-3H3/t7-,10+,13-,14+,15+,16?/m0/s1

InChI Key

RVLZTXZDKYFFMN-LRCVSGIZSA-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
Illicium jiadifengpi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Methyl ester
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045331

Chemspider ID

9719396

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11544617

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Condakes ML, Hung K, Harwood SJ, Maimone TJ: Total Syntheses of (-)-Majucin and (-)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes. J Am Chem Soc. 2017 Dec 13;139(49):17783-17786. doi: 10.1021/jacs.7b11493. Epub 2017 Nov 26. [PubMed:29148748 ]
Cheng X, Micalizio GC: Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin. J Am Chem Soc. 2016 Feb 3;138(4):1150-3. doi: 10.1021/jacs.5b12694. Epub 2016 Jan 25. [PubMed:26785051 ]
Trzoss L, Xu J, Lacoske MH, Mobley WC, Theodorakis EA: Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies. Chemistry. 2013 May 10;19(20):6398-408. doi: 10.1002/chem.201300198. Epub 2013 Mar 22. [PubMed:23526661 ]
Yang Y, Fu X, Chen J, Zhai H: Total synthesis of (-)-jiadifenin. Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9825-8. doi: 10.1002/anie.201203176. Epub 2012 Aug 24. [PubMed:22926836 ]
Fukuyama Y: [Synthetic Studies on Small Molecule Natural Products with Neurotrophic Activity]. Yakugaku Zasshi. 2022;142(3):241-277. doi: 10.1248/yakushi.21-00201. [PubMed:35228379 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate (NP0251711)

MOL for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

3D MOL for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

3D SDF for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

3D-SDF for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

PDB for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

3D PDB for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

SMILES for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

INCHI for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

Structure for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)

3D Structure for NP0251711 (methyl (1r,2r,6r,10r,11r)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.0¹,⁵.0⁶,¹⁰]tetradec-4-ene-13-carboxylate)