NP-MRD: Showing NP-Card for {13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate (NP0158851)

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Record Information

Version

1.0

Created at

2022-09-02 16:30:46 UTC

Updated at

2022-09-02 16:30:46 UTC

NP-MRD ID

NP0158851

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate

Description

{13-Hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]Hexadec-6-en-13-yl}methyl acetate belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae. It was first documented in 2022 (PMID: 36055769). Based on a literature review a significant number of articles have been published on {13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]Hexadec-6-en-13-yl}methyl acetate (PMID: 36055768) (PMID: 36055767) (PMID: 36055766) (PMID: 36055765) (PMID: 36055763) (PMID: 36055764).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022218302D          

 26 29  0  0  0  0            999 V2000
   -2.5227   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670   -1.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760   -1.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025   -2.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0783   -1.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654   -1.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1428   -0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128   -0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4870   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    0.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208    0.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234    1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541    1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0374    2.2029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1040    0.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266    0.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2829    1.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    0.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154    0.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366   -0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140   -0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    0.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3891   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    6.3732    0.2429    1.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3046   -0.5114    0.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641   -0.8975   -0.4764 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1038   -0.7709    1.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9887   -1.4352    0.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3816   -0.7064   -0.4060 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2934   -0.6254   -1.4389 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0642    0.7166   -0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979    0.8821    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3728    0.1534   -0.1746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0377   -1.3216   -0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692   -1.4198   -0.9636 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7142   -0.6490   -2.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1714    0.4401   -1.6123 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.4370   -0.6143   -2.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0516    0.0945    0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1845   -0.2263   -0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050    0.2892    1.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416    0.5316    1.9424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553    0.1893    2.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8908   -0.2486    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    0.5062    0.3939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7683    1.9831    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    1.2639    1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3446   -0.2730    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1879    0.2568    2.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230   -2.4971    0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192   -1.4183    1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2735   -1.4428   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    1.4288   -0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    0.9887    0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260    0.4620    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5067    1.9882    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8148   -1.9734   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814   -1.6067    0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698   -2.4510   -1.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -1.3708   -2.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5508   -0.2547   -2.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    1.3937   -1.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    1.6271   -2.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2431    0.1033   -3.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1807   -1.2701   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1393   -0.0739   -0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2623    0.5162   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995   -0.6007    3.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895    1.1209    2.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260   -1.3535    1.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0627   -0.1092    2.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240    2.3164    0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215    2.6101   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972    2.1719    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
 10  9  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 12  6  1  0
 25 18  1  0
 14 10  1  0
 25 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
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 12 39  1  6
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 14 42  1  1
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 20 45  1  0
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 20 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
M  END


  Mrv1652309022218302D          

 26 29  0  0  0  0            999 V2000
   -2.5227   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670   -1.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760   -1.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025   -2.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0783   -1.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654   -1.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1428   -0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128   -0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4870   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    0.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208    0.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234    1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541    1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0374    2.2029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1040    0.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266    0.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2829    1.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    0.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154    0.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366   -0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140   -0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    0.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3891   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
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 16 18  1  0  0  0  0
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 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158851

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1(O)CCC23CC1CC2CC(=O)C1=C(C)C(=O)CCC31C

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-12-16(23)4-5-19(3)18(12)17(24)9-14-8-15-10-20(14,19)6-7-21(15,25)11-26-13(2)22/h14-15,25H,4-11H2,1-3H3

> <INCHI_KEY>
NVWPECNLPBBETL-UHFFFAOYSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.45

> <EXACT_MASS>
360.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.48538219071861

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0^{1,10}.0^{2,7}]hexadec-6-en-13-yl}methyl acetate

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
1.9589410463333334

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.343632684828844

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.76924839498458

> <JCHEM_PKA_STRONGEST_BASIC>
-3.337130221677266

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
95.7409

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0^{1,10}.0^{2,7}]hexadec-6-en-13-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.709  -4.208   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.298  -3.590   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.129  -2.059   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.058  -4.502   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.647  -3.884   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.477  -2.353   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.013  -2.473   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.055  -2.826   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.133  -1.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.693  -0.055   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.397  -0.491   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.909  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.805   0.863   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.785   1.328   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.537   2.699   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.088   2.748   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.803   4.112   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.928   1.446   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.463   1.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.128   2.953   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.333   0.294   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.869   0.412   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.668  -1.095   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.133  -1.214   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.262   0.057   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.593  -1.330   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14   25                                             
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   18   10   26                                             
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
{13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0,.0,]hexadec-6-en-13-yl}methyl acetic acid	Generator

Chemical Formula

C₂₁H₂₈O₅

Average Mass

360.4500 Da

Monoisotopic Mass

360.19367 Da

IUPAC Name

{13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0^{1,10}.0^{2,7}]hexadec-6-en-13-yl}methyl acetate

Traditional Name

{13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0^{1,10}.0^{2,7}]hexadec-6-en-13-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1(O)CCC23CC1CC2CC(=O)C1=C(C)C(=O)CCC31C

InChI Identifier

InChI=1S/C21H28O5/c1-12-16(23)4-5-19(3)18(12)17(24)9-14-8-15-10-20(14,19)6-7-21(15,25)11-26-13(2)22/h14-15,25H,4-11H2,1-3H3

InChI Key

NVWPECNLPBBETL-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Chamigranes

Alternative Parents

Substituents

Chamigrane sesquiterpenoid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.58	ALOGPS
logP	1.96	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.74 m³·mol⁻¹	ChemAxon
Polarizability	38.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

162814125

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pays E, Radwanska M, Magez S: The Pathogenesis of African Trypanosomiasis. Annu Rev Pathol. 2022 Sep 2. doi: 10.1146/annurev-pathmechdis-031621-025153. [PubMed:36055769 ]
Khan K, Van Aken O: The colonisation of land was a likely driving force for the evolution of mitochondrial retrograde signalling in plants. J Exp Bot. 2022 Sep 3. pii: 6687801. doi: 10.1093/jxb/erac351. [PubMed:36055768 ]
Authors unspecified: Erratum. Br J Dermatol. 2022 Sep;187(3):451. doi: 10.1111/bjd.21748. [PubMed:36055767 ]
Authors unspecified: BAD and BPG guidelines for narrowband ultraviolet B phototherapy 2022. Br J Dermatol. 2022 Sep;187(3):vi. doi: 10.1111/bjd.21734. [PubMed:36055766 ]
Sprecher E: What do rare and common have in common? Br J Dermatol. 2022 Sep;187(3):279-280. doi: 10.1111/bjd.21632. [PubMed:36055765 ]
Dias BGC, Santos FAP, Meschiatti M, Brixner BM, Almeida AA, Queiroz O, Cappellozza BI: Effects of feeding different probiotic types on metabolic, performance, and carcass responses of Bos indicus feedlot cattle offered a high-concentrate diet. J Anim Sci. 2022 Oct 1;100(10). pii: 6687795. doi: 10.1093/jas/skac289. [PubMed:36055763 ]
Authors unspecified: Revolutionizing Atopic Dermatitis, 9-11 April 2022. Br J Dermatol. 2022 Sep;187(3):e80-e155. doi: 10.1111/bjd.21666. [PubMed:36055764 ]
Wang B, Lv R, Zhang Z, Yang C, Xun H, Liu B, Gong L: Homoeologous exchange enables rapid evolution of tolerance to salinity and hyper-osmotic stresses in a synthetic allotetraploid wheat. J Exp Bot. 2022 Dec 8;73(22):7488-7502. doi: 10.1093/jxb/erac355. [PubMed:36055762 ]
Horwitz JK, Kaldas FM: CAQ Corner: Technical considerations in liver transplantation (101 for hepatologists). Liver Transpl. 2023 Feb 1;29(2):217-225. doi: 10.1002/lt.26556. Epub 2023 Jan 17. [PubMed:36055761 ]
Wang P, Mou P, Hu L, Hu S: Effects of nutrient heterogeneity on root foraging and plant growth at the individual and community level. J Exp Bot. 2022 Dec 8;73(22):7503-7515. doi: 10.1093/jxb/erac358. [PubMed:36055760 ]
LOTUS database [Link]

Showing NP-Card for {13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate (NP0158851)

MOL for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

3D MOL for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

3D SDF for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

3D-SDF for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

PDB for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

3D PDB for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

SMILES for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

INCHI for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

Structure for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)

3D Structure for NP0158851 ({13-hydroxy-2,6-dimethyl-5,8-dioxotetracyclo[10.3.1.0¹,¹⁰.0²,⁷]hexadec-6-en-13-yl}methyl acetate)