NP-MRD: Showing NP-Card for ((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate (NP0331813)

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Record Information

Version

2.0

Created at

2023-09-13 16:01:27 UTC

Updated at

2025-06-11 03:41:05 UTC

NP-MRD ID

NP0331813

Natural Product DOI

https://doi.org/10.57994/0901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate

Description

((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]Dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]Dodecan-1-yl)methyl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on ((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]Dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]Dodecan-1-yl)methyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09132316012D          

 46 50  0  0  1  0            999 V2000
   -2.4063    0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350    0.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -0.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -0.1846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0537    0.3543    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -0.5873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0118    0.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -1.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6560   -1.9233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238   -2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630   -3.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2475   -3.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9595   -0.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699    1.0311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9310    1.6558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6840    1.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241    2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    1.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    1.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.5868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4549    1.1621    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412   -1.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8551   -1.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898   -1.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7204   -0.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5344   -0.1677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3453   -0.3195    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9544    0.5424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1536    0.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    1.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6091    1.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698    2.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2638    3.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8365    3.0146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7325    0.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5048    0.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9097   -0.1927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7579   -1.0036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5361   -0.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1629   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1204   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2954   -1.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690   -0.9816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4471   -1.7762    0.0000 H   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
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16  8  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  1  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22  2  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 28 27  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 38  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 41  1  1  0  0  0
 40 42  1  6  0  0  0
 40 43  1  0  0  0  0
 43 44  1  0  0  0  0
 45 44  1  0  0  0  0
 45 25  1  0  0  0  0
 28 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END


  Mrv2104 09132316012D          

 46 50  0  0  1  0            999 V2000
   -2.4063    0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350    0.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -0.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -0.1846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0537    0.3543    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -0.5873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0118    0.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -1.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6560   -1.9233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238   -2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630   -3.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2475   -3.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9595   -0.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699    1.0311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9310    1.6558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6840    1.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241    2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    1.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    1.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.5868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4549    1.1621    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412   -1.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8551   -1.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898   -1.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7204   -0.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5344   -0.1677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3453   -0.3195    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9544    0.5424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1536    0.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    1.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6091    1.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698    2.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2638    3.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8365    3.0146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7325    0.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5048    0.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9097   -0.1927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7579   -1.0036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5361   -0.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1629   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1204   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2954   -1.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690   -0.9816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4471   -1.7762    0.0000 H   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
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16  8  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  1  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22  2  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 28 27  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 38  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 41  1  1  0  0  0
 40 42  1  6  0  0  0
 40 43  1  0  0  0  0
 43 44  1  0  0  0  0
 45 44  1  0  0  0  0
 45 25  1  0  0  0  0
 28 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0331813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC(C)(C)[C@]1([H])CC[C@](C)(O)[C@@H]1CC[C@@]2(COC(C)=O)O1.[H][C@]12CC(C)(C)[C@]1([H])CC[C@]1(C)O[C@@H]1CC[C@@]2(O)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/2C17H28O4/c1-11(18)20-10-17(19)8-6-14-16(4,21-14)7-5-12-13(17)9-15(12,2)3;1-11(18)20-10-17-8-6-14(21-17)16(4,19)7-5-12-13(17)9-15(12,2)3/h2*12-14,19H,5-10H2,1-4H3/t12-,13+,14-,16+,17-;12-,13+,14+,16+,17+/m11/s1

> <INCHI_KEY>
FQXQRVGXPFUHGH-GUYAANQOSA-N

> <FORMULA>
C34H56O8

> <MOLECULAR_WEIGHT>
592.814

> <EXACT_MASS>
592.397518763

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
33.8813648015985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.0^{2,5}]dodecan-1-yl]methyl acetate; [(1R,4S,6R,9S,10S)-9-hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-9-yl]methyl acetate

> <JCHEM_LOGP>
2.0451819129999995

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.055385760608832

> <JCHEM_PKA_STRONGEST_BASIC>
-3.211974268309698

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
78.81269999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.0^{2,5}]dodecan-1-yl]methyl acetate; [(1R,4S,6R,9S,10S)-9-hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-9-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-23         0                                  
HETATM    1  C   UNK     0      -4.492   0.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.052   0.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.598   1.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.506  -0.891   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.066  -0.345   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       0.100   0.661   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       0.278  -1.096   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.889   0.106   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.031  -2.616   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.225  -3.590   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.978  -5.110   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.171  -6.084   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.462  -5.657   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.791  -0.808   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.765   0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.744   1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.738   3.091   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.144   3.720   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.538   4.618   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.218   3.338   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.105   2.549   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.612   1.095   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -2.716   2.169   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       7.544  -2.335   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.063  -2.084   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.314  -3.603   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.811  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.331  -0.313   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      11.844  -0.596   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      11.115   1.013   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.620   1.383   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.041   2.551   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.337   3.383   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.264   4.922   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.559   5.754   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.895   5.627   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      12.567   1.524   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.009   0.982   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.765  -0.360   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.481  -1.873   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      15.934  -1.362   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      15.237  -3.215   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.291  -2.851   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.751  -2.835   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.582  -1.832   0.000  0.00  0.00           C+0
HETATM   46  H   UNK     0      10.168  -3.316   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   22                                             
CONECT    6    5                                                            
CONECT    7    5    8    9   14                                             
CONECT    8    7   16                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2    5   23                                             
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25   24   26   27   45                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30   45                                             
CONECT   29   28                                                            
CONECT   30   28   31   32   37                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   30   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39   41   42   43                                             
CONECT   41   40   39                                                       
CONECT   42   40                                                            
CONECT   43   40   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   25   28   46                                             
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Value	Source
((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetic acid and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetic acid	Generator

Chemical Formula

C₃₄H₅₆O₈

Average Mass

592.8140 Da

Monoisotopic Mass

592.39752 Da

IUPAC Name

[(1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.0^{2,5}]dodecan-1-yl]methyl acetate; [(1R,4S,6R,9S,10S)-9-hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-9-yl]methyl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@]12CC(C)(C)[C@]1([H])CC[C@](C)(O)[C@@H]1CC[C@@]2(COC(C)=O)O1.[H][C@]12CC(C)(C)[C@]1([H])CC[C@]1(C)O[C@@H]1CC[C@@]2(O)COC(C)=O

InChI Identifier

InChI=1S/2C17H28O4/c1-11(18)20-10-17(19)8-6-14-16(4,21-14)7-5-12-13(17)9-15(12,2)3;1-11(18)20-10-17-8-6-14(21-17)16(4,19)7-5-12-13(17)9-15(12,2)3/h2*12-14,19H,5-10H2,1-4H3/t12-,13+,14-,16+,17-;12-,13+,14+,16+,17+/m11/s1

InChI Key

FQXQRVGXPFUHGH-GUYAANQOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C3D6O, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, C3D6O, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C3D6O, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, C3D6O, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C3D6O, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, C3D6O, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100.578570142, C3D6O, simulated)	[email protected]	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101, C3D6O, simulated)	[email protected]	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-08	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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

Farsesane sesquiterpenoid
Caryophyllane sesquiterpenoid
Sesquiterpenoid
Fatty alcohol ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Not Available

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	2.05	ChemAxon
pKa (Strongest Acidic)	14.06	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.81 m³·mol⁻¹	ChemAxon
Polarizability	33.88 Å³	ChemAxon
Number of Rings	6	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.3c00574

Showing NP-Card for ((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate (NP0331813)

MOL for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

3D MOL for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

3D SDF for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

3D-SDF for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

PDB for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

3D PDB for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

SMILES for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

INCHI for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

Structure for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)

3D Structure for NP0331813 (((1R,4S,6R,9S,10S)-9-Hydroxy-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan-9-yl)methyl acetate and ((1R,2S,5R,8S,9S)-8-hydroxy-4,4,8-trimethyl-12-oxatricyclo[7.2.1.02,5]dodecan-1-yl)methyl acetate)