NP-MRD: Showing NP-Card for (1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one (NP0165075)

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Record Information

Version

2.0

Created at

2022-09-03 00:05:48 UTC

Updated at

2022-09-03 00:05:49 UTC

NP-MRD ID

NP0165075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Macrophorin A 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. (1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one is found in Botryosphaeria berengeriana. It was first documented in 2012 (PMID: 22822371). Based on a literature review very few articles have been published on Macrophorin A (PMID: 27417331).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202052D          

 26 29  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
    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  1  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  2  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    0.9880    2.2189   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624    1.2760    0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3692    1.5979    1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8650    1.3765    1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1965    0.0906    0.9741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6404   -0.2441    0.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9137   -1.6058    1.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4545    0.7569    1.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897   -0.2930   -0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -1.0564   -1.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562   -1.2100   -1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561    0.0080   -0.4053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7580    1.2556   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -0.0573   -0.0960 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7391   -0.6273   -1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1962   -0.7313   -0.9438 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9371   -1.3438   -2.1100 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1310   -0.0295   -1.7965 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3448    0.4973   -1.1210 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2589    0.9660   -2.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659   -0.4034   -0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4315   -0.2906    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8969   -1.1923    1.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1952   -1.2626    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577   -1.3471    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0165   -1.9309    1.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    3.1965    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    2.1609   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160    2.6658    2.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191    0.9810    2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4193    2.2468    1.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1935    1.2274    2.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6693   -0.7161    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9915   -1.9319    2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -1.5964    2.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881   -2.3838    0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1582    0.6767    2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4004    1.7691    1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5191    0.4210    1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6128    0.7244   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2675   -0.8435   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9237   -2.0998   -1.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -0.6004   -2.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969   -1.3122   -2.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454   -2.0930   -0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6025    1.1782   -1.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8284    2.1749   -0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8464    1.3761   -1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220   -0.7708    0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693   -1.6853   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967   -0.1474   -2.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7051    0.6794   -2.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0261    1.4142   -0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    0.2052   -2.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7520    0.7359    0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -0.5811   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6706   -2.1051    0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6497   -1.9417    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 16 15  1  6
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  2  0
 14  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5 12  1  0
 18 16  1  0
 25 16  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  1
 15 50  1  0
 15 51  1  0
 18 52  1  6
 19 53  1  1
 20 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  1
M  END


  Mrv1652309032202052D          

 26 29  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
    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  1  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  2  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0165075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@@H](C[C@@]34O[C@@H]3[C@H](O)C(CO)=CC4=O)C(=C)CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O4/c1-13-6-7-16-20(2,3)8-5-9-21(16,4)15(13)11-22-17(24)10-14(12-23)18(25)19(22)26-22/h10,15-16,18-19,23,25H,1,5-9,11-12H2,2-4H3/t15-,16-,18+,19+,21+,22-/m0/s1

> <INCHI_KEY>
OOIYDCZXWGFDDL-VKUFQHAMSA-N

> <FORMULA>
C22H32O4

> <MOLECULAR_WEIGHT>
360.494

> <EXACT_MASS>
360.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.384048018582746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
3.1281381433333344

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.255311945876905

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.180562624060393

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7845052331238023

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
100.65809999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R)-1-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-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  C   UNK     0       1.929   3.882   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.699   2.548   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.929   1.215   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.469   1.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.699  -0.119   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.239  -0.119   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.009   1.215   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.676   1.985   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.009   2.755   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.343   3.525   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.343   5.065   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.677   2.755   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.010   3.525   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.010   5.065   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.677   1.215   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.343   0.445   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.343  -1.095   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   16   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   16   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₄

Average Mass

360.4940 Da

Monoisotopic Mass

360.23006 Da

IUPAC Name

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

Traditional Name

(1R,5R,6R)-1-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-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)CCC[C@]2(C)[C@@H](C[C@@]34O[C@@H]3[C@H](O)C(CO)=CC4=O)C(=C)CC[C@@H]12

InChI Identifier

InChI=1S/C22H32O4/c1-13-6-7-16-20(2,3)8-5-9-21(16,4)15(13)11-22-17(24)10-14(12-23)18(25)19(22)26-22/h10,15-16,18-19,23,25H,1,5-9,11-12H2,2-4H3/t15-,16-,18+,19+,21+,22-/m0/s1

InChI Key

OOIYDCZXWGFDDL-VKUFQHAMSA-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
Botryosphaeria berengeriana	LOTUS Database	35616633

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
Aldehyde
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	3.02	ALOGPS
logP	3.13	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.66 m³·mol⁻¹	ChemAxon
Polarizability	40.38 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

139728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

158854

PDB ID

Not Available

ChEBI ID

175637

Good Scents ID

Not Available

References

General References

Fang SM, Cui CB, Li CW, Wu CJ, Zhang ZJ, Li L, Huang XJ, Ye WC: Purpurogemutantin and purpurogemutantidin, new drimenyl cyclohexenone derivatives produced by a mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59. Mar Drugs. 2012 Jun;10(6):1266-87. doi: 10.3390/md10061266. Epub 2012 Jun 4. [PubMed:22822371 ]
He WJ, Zhou XJ, Qin XC, Mai YX, Lin XP, Liao SR, Yang B, Zhang T, Tu ZC, Wang JF, Liu Y: Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7. Nat Prod Res. 2017 Mar;31(5):604-609. doi: 10.1080/14786419.2016.1207076. Epub 2016 Jul 15. [PubMed:27417331 ]
LOTUS database [Link]

Showing NP-Card for (1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one (NP0165075)

MOL for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D MOL for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D SDF for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D-SDF for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

PDB for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D PDB for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

SMILES for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

INCHI for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

Structure for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)

3D Structure for NP0165075 ((1r,5r,6r)-1-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one)