NP-MRD: Showing NP-Card for (1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one (NP0166523)

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Record Information

Version

2.0

Created at

2022-09-03 01:55:24 UTC

Updated at

2022-09-03 01:55:24 UTC

NP-MRD ID

NP0166523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

Description

5'-Epimacrophorin B belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. It was first documented in 2022 (PMID: 36057430). Based on a literature review a significant number of articles have been published on 5'-epimacrophorin B (PMID: 36057416) (PMID: 36057403) (PMID: 36057355) (PMID: 36057350).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032203552D          

 27 30  0  0  1  0            999 V2000
    1.4460   -1.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2040   -0.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085    0.6507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2040    1.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8359    0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8359    1.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2040    2.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    1.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335    0.6507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8585    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460   -0.0638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2710   -0.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    0.6507    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9691    1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    1.4757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3980    1.8882    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3980    2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8270    1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8270    2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -0.5868    0.0000 O   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
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    0.0487    2.7591   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709    1.6340   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2626    1.6828   -2.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221    0.8116   -1.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6139    0.4009   -0.4681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9552   -0.0761   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3650   -1.4252   -0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316    0.9012   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8390   -0.1588    1.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792    0.4466    2.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7714   -1.0198    1.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6111   -1.2757    1.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761   -0.5032   -0.1304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1833   -1.4050   -1.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2409    0.3957   -0.0093 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9823   -0.3682   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2784    0.3694   -0.1418 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5562    1.5279   -0.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    0.3745   -1.1294 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7052    0.4029   -0.8000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4368   -0.3987   -1.6984 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371   -0.0658    0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4353   -0.5019    0.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7967   -1.5735   -0.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1689   -0.1200    1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070    0.3139    1.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    0.6492    2.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6370    2.8236    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970    3.7094   -0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375    1.3864   -2.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756    2.7298   -2.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250    1.4573   -2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5662    0.0065   -2.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430    1.3583    0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4375   -1.5575   -0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8295   -2.2711   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4271   -1.4997   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9428    0.6405    0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801    1.9498   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2662    0.7449   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2738   -1.9838    2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4646   -0.5710    2.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -1.1846    1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6047   -2.3745    0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044   -0.8935   -2.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0801   -1.9664   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4396   -2.2052   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705    0.6493    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095   -1.2490    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121   -0.8289   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298   -0.0006   -2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0956    1.4293   -0.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255   -1.0963   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6315   -0.7088    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0955    0.3536    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4877   -2.1513    0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4755   -0.4739    2.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 15  1  0
 15 16  1  0
 17 16  1  6
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  2  0
 15 13  1  0
 13 14  1  6
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  6  1  0
 13  5  1  0
 19 17  1  0
 26 17  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  5 34  1  1
  4 32  1  0
  4 33  1  0
  3 30  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 19 51  1  6
 20 52  1  1
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 12 43  1  0
 12 44  1  0
 11 41  1  0
 11 42  1  0
M  END


  Mrv1652309032203552D          

 27 30  0  0  1  0            999 V2000
    1.4460   -1.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2040   -0.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085    0.6507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2040    1.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8359    0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8359    1.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2040    2.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    1.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335    0.6507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8585    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460   -0.0638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2710   -0.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    0.6507    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9691    1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    1.4757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3980    1.8882    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3980    2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8270    1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8270    2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -0.5868    0.0000 O   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
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0166523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2CCC(=C)[C@H](C[C@]34O[C@H]3[C@H](O)C(CO)=CC4=O)[C@@]2(C)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-12-5-6-15-20(2,3)16(24)7-8-21(15,4)14(12)10-22-17(25)9-13(11-23)18(26)19(22)27-22/h9,14-15,18-19,23,26H,1,5-8,10-11H2,2-4H3/t14-,15-,18+,19-,21+,22+/m0/s1

> <INCHI_KEY>
ZJZYSAJQOPJREK-OUIOBULKSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.26606974322398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,6S)-1-{[(1S,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-6-oxo-decahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.4608547819999997

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.255302585565161

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.180562531231015

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7845052331241282

> <JCHEM_POLAR_SURFACE_AREA>
87.13

> <JCHEM_REFRACTIVITY>
101.35129999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6S)-1-{[(1S,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.699  -2.786   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.929  -1.453   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.389  -1.453   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.381  -0.119   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.389   1.215   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.381   2.548   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.560   1.558   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.560   3.538   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.389   3.882   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.381   5.216   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.929   3.882   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.699   2.548   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.929   1.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.469   1.215   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.699  -0.119   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.239  -0.119   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.009   1.215   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.676   1.985   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.009   2.755   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.343   3.525   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.343   5.065   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.677   2.755   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.010   3.525   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.010   5.065   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.677   1.215   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.343   0.445   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.343  -1.095   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   26                                             
CONECT   18   17   19                                                       
CONECT   19   18   17   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   17   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(1S,5R,6S)-1-{[(1S,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-6-oxo-decahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

Traditional Name

(1S,5R,6S)-1-{[(1S,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2CCC(=C)[C@H](C[C@]34O[C@H]3[C@H](O)C(CO)=CC4=O)[C@@]2(C)CCC1=O

InChI Identifier

InChI=1S/C22H30O5/c1-12-5-6-15-20(2,3)16(24)7-8-21(15,4)14(12)10-22-17(25)9-13(11-23)18(26)19(22)27-22/h9,14-15,18-19,23,26H,1,5-8,10-11H2,2-4H3/t14-,15-,18+,19-,21+,22+/m0/s1

InChI Key

ZJZYSAJQOPJREK-OUIOBULKSA-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 cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
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	1.89	ALOGPS
logP	2.46	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.35 m³·mol⁻¹	ChemAxon
Polarizability	40.27 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

146682213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Delahunt A, Conway MC, Callaghan SL, O'Brien EC, Geraghty AA, O'Reilly SL, McDonnell CM, Mehegan J, McAuliffe FM: Maternal dietary quality during pregnancy and child appetitive traits at 5-years-old: Findings from the ROLO longitudinal birth cohort study. Appetite. 2022 Aug 31;179:106291. doi: 10.1016/j.appet.2022.106291. [PubMed:36057430 ]
Oliveira FADS, de Holanda MV, Lima LB, Dantas MB, Duarte IO, de Castro LGZ, de Oliveira LLB, Paier CRK, Moreira-Nunes CFA, Lima NCB, Melo VMM, Montenegro RC: Genomic Surveillance: Circulating lineages and genomic variation of SARS-CoV-2 in early pandemic in Ceara state, Northeast Brazil. Virus Res. 2022 Aug 31:198908. doi: 10.1016/j.virusres.2022.198908. [PubMed:36057416 ]
Marszalek-Grabska M, Zakrocka I, Budzynska B, Marciniak S, Kaszubska K, Lemieszek MK, Winiarczyk S, Kotlinska JH, Rzeski W, Turski WA: Binge-like mephedrone treatment induces memory impairment concomitant with brain kynurenic acid reduction in mice. Toxicol Appl Pharmacol. 2022 Aug 31;454:116216. doi: 10.1016/j.taap.2022.116216. [PubMed:36057403 ]
Rajivgandhi G, Ramachandran G, Chackaravarthi G, Maruthupandy M, Quero F, Chelliah CK, Manoharan N, Alharbi NS, Kadaikunnan S, Khaled JM, Li WJ: Metal tolerance and biosorption of Pb ions by Bacillus cereus RMN 1 (MK521259) isolated from metal contaminated sites. Chemosphere. 2022 Aug 31;308(Pt 1):136270. doi: 10.1016/j.chemosphere.2022.136270. [PubMed:36057355 ]
Saravanan S, Carolin C F, Kumar PS, Chitra B, Rangasamy G: Biodegradation of textile dye Rhodamine-B by Brevundimonas diminuta and screening of their breakdown metabolites. Chemosphere. 2022 Aug 31;308(Pt 1):136266. doi: 10.1016/j.chemosphere.2022.136266. [PubMed:36057350 ]
LOTUS database [Link]

Showing NP-Card for (1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one (NP0166523)

MOL for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D MOL for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D SDF for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D-SDF for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

PDB for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D PDB for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

SMILES for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

INCHI for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

Structure for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D Structure for NP0166523 ((1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)