NP-MRD: Showing NP-Card for methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate (NP0247349)

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Record Information

Version

2.0

Created at

2022-09-07 09:10:38 UTC

Updated at

2022-09-07 09:10:38 UTC

NP-MRD ID

NP0247349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate

Description

Methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,9aH-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate is found in Trichilia emetica. Based on a literature review very few articles have been published on methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,9aH-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211102D          

 42 45  0  0  0  0            999 V2000
   -0.6102   -1.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6043   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089    0.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0781   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309072211102D          

 42 45  0  0  0  0            999 V2000
   -0.6102   -1.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089    0.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7203   -1.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3503   -2.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2041   -2.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3443   -3.6889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0291   -2.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0321   -2.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0260   -3.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8541   -2.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4278   -3.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816   -3.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9116   -4.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6879   -4.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7653   -5.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7978   -2.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -1.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0183   -2.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -2.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -2.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.7921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199   -2.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -3.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -4.0270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3991   -4.0217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4021   -4.8467    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 14 28  1  0  0  0  0
 13 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC(O)C1(C)C(CC(O)C2(C)C1CCC1(C)C(CC=C21)C1COC(O)(C(C1)OC(C)=O)C(C)(C)O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H52O9/c1-18(2)22-15-25(35)32(8)23-11-10-21(20-14-27(42-19(3)34)33(39,41-17-20)29(4,5)38)30(23,6)13-12-24(32)31(22,7)26(36)16-28(37)40-9/h11,20-22,24-27,35-36,38-39H,1,10,12-17H2,2-9H3

> <INCHI_KEY>
VDZOAKVFCQHFIH-UHFFFAOYSA-N

> <FORMULA>
C33H52O9

> <MOLECULAR_WEIGHT>
592.77

> <EXACT_MASS>
592.361133254

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
66.27358107363212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,9aH-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate

> <JCHEM_LOGP>
2.6007583029999974

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.928667340681127

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.110533199721095

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3509270074647778

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
156.98240000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2H,3H,4H,5H,5aH,7H,8H,9H-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate

> <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      -1.139  -2.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.411  -1.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.222  -0.327   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.128  -1.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.856  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.395  -0.183   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.123   1.174   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.207  -1.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.935  -0.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.746  -1.444   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.740  -0.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.166  -0.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.053  -2.386   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.229  -3.380   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.678  -2.859   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.854  -3.853   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.581  -5.368   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.843  -6.886   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.121  -5.374   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.127  -3.834   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.115  -6.914   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.661  -5.380   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.132  -5.890   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.859  -7.405   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.035  -8.400   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.484  -7.878   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.762  -9.915   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.956  -4.896   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.557  -2.753   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.501  -3.970   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.829  -4.110   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.290  -4.158   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.479  -2.849   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.939  -2.897   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.660  -3.754   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.934  -4.437   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.265  -5.212   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.597  -5.202   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.592  -6.742   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.922  -7.517   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -0.745  -7.507   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.751  -9.047   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   33                                             
CONECT    9    8                                                            
CONECT   10    8   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   17   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   14                                                       
CONECT   29   13   10   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    8   34                                                  
CONECT   34   33    4   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2H,3H,3ah,4H,5H,5ah,6H,7H,8H,9H,9ah-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoic acid	Generator

Chemical Formula

C₃₃H₅₂O₉

Average Mass

592.7700 Da

Monoisotopic Mass

592.36113 Da

IUPAC Name

methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,9aH-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate

Traditional Name

methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2H,3H,4H,5H,5aH,7H,8H,9H-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC(O)C1(C)C(CC(O)C2(C)C1CCC1(C)C(CC=C21)C1COC(O)(C(C1)OC(C)=O)C(C)(C)O)C(C)=C

InChI Identifier

InChI=1S/C33H52O9/c1-18(2)22-15-25(35)32(8)23-11-10-21(20-14-27(42-19(3)34)33(39,41-17-20)29(4,5)38)30(23,6)13-12-24(32)31(22,7)26(36)16-28(37)40-9/h11,20-22,24-27,35-36,38-39H,1,10,12-17H2,2-9H3

InChI Key

VDZOAKVFCQHFIH-UHFFFAOYSA-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
Trichilia emetica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Oxane
Cyclic alcohol
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
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	2.6	ChemAxon
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	156.98 m³·mol⁻¹	ChemAxon
Polarizability	66.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

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BioCyc ID

Not Available

BiGG ID

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Wikipedia Link

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METLIN ID

Not Available

PubChem Compound

73797355

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate (NP0247349)

MOL for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

3D MOL for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

3D SDF for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

3D-SDF for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

PDB for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

3D PDB for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

SMILES for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

INCHI for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

Structure for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)

3D Structure for NP0247349 (methyl 3-{3-[5-(acetyloxy)-6-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-(prop-1-en-2-yl)-2h,3h,4h,5h,5ah,7h,8h,9h-cyclopenta[a]naphthalen-6-yl}-3-hydroxypropanoate)