NP-MRD: Showing NP-Card for 1beta(R),10beta(S)-dioxa-isophotosantonin (NP0037058)

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Record Information

Version

2.0

Created at

2021-06-20 20:04:19 UTC

Updated at

2021-06-30 00:09:03 UTC

NP-MRD ID

NP0037058

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1beta(R),10beta(S)-dioxa-isophotosantonin

Provided By

JEOL Database JEOL Logo

Description

(AlphaS,4S)-alpha,3,8-Trimethyl-2-oxo-4beta-hydroxy-8alpha,8aalpha-epoxy-1,2,4,5,6,7,8,8a-octahydroazulene-5alpha-acetic acid 5,4-lactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 1beta(R),10beta(S)-dioxa-isophotosantonin is found in Artemisia gorgonum. 1beta(R),10beta(S)-dioxa-isophotosantonin was first documented in 2012 (Macias, F. A., et al.). Based on a literature review very few articles have been published on (alphaS,4S)-alpha,3,8-Trimethyl-2-oxo-4beta-hydroxy-8alpha,8aalpha-epoxy-1,2,4,5,6,7,8,8a-octahydroazulene-5alpha-acetic acid 5,4-lactone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122043D          

 37 40  0  0  0  0            999 V2000
    1.6980   -1.6089   -1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -1.5559   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947   -0.5739    0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    0.8969    0.3587 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1945    1.2248   -0.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    2.3556   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    2.9310   -2.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5706    2.7754   -0.6412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6338    3.2856   -1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9604    1.4739    0.0519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8108    1.6731    1.3029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4414    0.3800    1.8070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5569   -0.6408    2.4831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3072   -1.5843    3.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -0.1607    3.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726   -1.0251    1.9529 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3645   -2.4071    2.2118 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9856   -2.7422    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -3.8341    0.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -0.8733   -2.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5886   -1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -1.4371   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.4142    1.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    3.5513    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    2.5511   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    4.1990   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    3.5163   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907    0.8313   -0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313    2.1552    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6294    2.3622    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.6767    2.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705   -0.1163    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -1.0364    4.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687   -2.3111    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -2.1301    4.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -3.1455    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -2.4074    2.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  4  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  8 10  1  0  0  0  0
 13 16  1  0  0  0  0
 18 19  2  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 16 17  1  0  0  0  0
 16 15  1  1  0  0  0
 13 15  1  0  0  0  0
 17 18  1  0  0  0  0
  6  7  2  0  0  0  0
 18  2  1  0  0  0  0
 13 14  1  1  0  0  0
  2  3  2  0  0  0  0
  8  9  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 10 28  1  6  0  0  0
  4 23  1  1  0  0  0
  8 24  1  1  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
M  END

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    1.6980   -1.6089   -1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -1.5559   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947   -0.5739    0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    0.8969    0.3587 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1945    1.2248   -0.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    2.3556   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    2.9310   -2.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5706    2.7754   -0.6412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6338    3.2856   -1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9604    1.4739    0.0519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8108    1.6731    1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414    0.3800    1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -0.6408    2.4831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3072   -1.5843    3.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -0.1607    3.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726   -1.0251    1.9529 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3645   -2.4071    2.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856   -2.7422    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -3.8341    0.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -0.8733   -2.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5886   -1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -1.4371   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.4142    1.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    3.5513    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    2.5511   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    4.1990   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    3.5163   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907    0.8313   -0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313    2.1552    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6294    2.3622    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.6767    2.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705   -0.1163    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -1.0364    4.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687   -2.3111    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -2.1301    4.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -3.1455    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -2.4074    2.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  4  1  0
  3  4  1  0
  3 16  1  0
 13 12  1  0
 12 11  1  0
  4  5  1  0
  5  6  1  0
  6  8  1  0
  8 10  1  0
 13 16  1  0
 18 19  2  0
 10 11  1  0
  2  1  1  0
 16 17  1  0
 16 15  1  1
 13 15  1  0
 17 18  1  0
  6  7  2  0
 18  2  1  0
 13 14  1  1
  2  3  2  0
  8  9  1  0
 12 31  1  0
 12 32  1  0
 11 29  1  0
 11 30  1  0
 17 36  1  0
 17 37  1  0
 10 28  1  6
  4 23  1  1
  8 24  1  1
  1 20  1  0
  1 21  1  0
  1 22  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
M  END


  Mrv1652306202122043D          

 37 40  0  0  0  0            999 V2000
    1.6980   -1.6089   -1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -1.5559   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947   -0.5739    0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    0.8969    0.3587 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1945    1.2248   -0.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    2.3556   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    2.9310   -2.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5706    2.7754   -0.6412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6338    3.2856   -1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9604    1.4739    0.0519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8108    1.6731    1.3029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4414    0.3800    1.8070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5569   -0.6408    2.4831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3072   -1.5843    3.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -0.1607    3.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726   -1.0251    1.9529 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3645   -2.4071    2.2118 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9856   -2.7422    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -3.8341    0.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -0.8733   -2.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5886   -1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -1.4371   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.4142    1.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    3.5513    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    2.5511   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    4.1990   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    3.5163   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907    0.8313   -0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313    2.1552    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6294    2.3622    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.6767    2.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705   -0.1163    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -1.0364    4.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687   -2.3111    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -2.1301    4.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -3.1455    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -2.4074    2.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  4  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  8 10  1  0  0  0  0
 13 16  1  0  0  0  0
 18 19  2  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 16 17  1  0  0  0  0
 16 15  1  1  0  0  0
 13 15  1  0  0  0  0
 17 18  1  0  0  0  0
  6  7  2  0  0  0  0
 18  2  1  0  0  0  0
 13 14  1  1  0  0  0
  2  3  2  0  0  0  0
  8  9  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 10 28  1  6  0  0  0
  4 23  1  1  0  0  0
  8 24  1  1  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037058

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])C1=C2[C@@]3([H])OC(=O)[C@@]([H])(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]3(O[C@]23C([H])([H])C1=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-7-9-4-5-14(3)15(19-14)6-10(16)8(2)11(15)12(9)18-13(7)17/h7,9,12H,4-6H2,1-3H3/t7-,9-,12-,14-,15+/m0/s1

> <INCHI_KEY>
RUBXBCDKYAQXTM-ZAHDETNWSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.644011864477456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,6S,7S,10S)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-11-ene-8,13-dione

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.6672904300000002

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.074557314599932

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2832350286998135

> <JCHEM_POLAR_SURFACE_AREA>
55.9

> <JCHEM_REFRACTIVITY>
67.12769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,6S,7S,10S)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-11-ene-8,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    1.6980   -1.6089   -1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -1.5559   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947   -0.5739    0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    0.8969    0.3587 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1945    1.2248   -0.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    2.3556   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    2.9310   -2.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5706    2.7754   -0.6412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6338    3.2856   -1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9604    1.4739    0.0519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8108    1.6731    1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414    0.3800    1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -0.6408    2.4831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3072   -1.5843    3.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -0.1607    3.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726   -1.0251    1.9529 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3645   -2.4071    2.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856   -2.7422    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -3.8341    0.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -0.8733   -2.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5886   -1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -1.4371   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.4142    1.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    3.5513    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    2.5511   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    4.1990   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    3.5163   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907    0.8313   -0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313    2.1552    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6294    2.3622    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.6767    2.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705   -0.1163    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -1.0364    4.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687   -2.3111    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -2.1301    4.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -3.1455    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -2.4074    2.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  4  1  0
  3  4  1  0
  3 16  1  0
 13 12  1  0
 12 11  1  0
  4  5  1  0
  5  6  1  0
  6  8  1  0
  8 10  1  0
 13 16  1  0
 18 19  2  0
 10 11  1  0
  2  1  1  0
 16 17  1  0
 16 15  1  1
 13 15  1  0
 17 18  1  0
  6  7  2  0
 18  2  1  0
 13 14  1  1
  2  3  2  0
  8  9  1  0
 12 31  1  0
 12 32  1  0
 11 29  1  0
 11 30  1  0
 17 36  1  0
 17 37  1  0
 10 28  1  6
  4 23  1  1
  8 24  1  1
  1 20  1  0
  1 21  1  0
  1 22  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.698  -1.609  -1.338  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.008  -1.556  -0.028  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.395  -0.574   0.665  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.406   0.897   0.359  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.194   1.225  -0.786  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.687   2.356  -1.360  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.203   2.931  -2.303  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.571   2.775  -0.641  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.634   3.286  -1.599  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.960   1.474   0.052  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.811   1.673   1.303  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.441   0.380   1.807  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.557  -0.641   2.483  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.307  -1.584   3.393  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.345  -0.161   3.082  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.173  -1.025   1.953  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.365  -2.407   2.212  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.986  -2.742   0.873  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.440  -3.834   0.566  0.00  0.00           O+0
HETATM   20  H   UNK     0       1.299  -0.873  -2.042  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.562  -2.589  -1.808  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.771  -1.437  -1.215  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.875   1.414   1.208  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.301   3.551   0.085  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.856   2.551  -2.381  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.295   4.199  -2.099  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.564   3.516  -1.071  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.491   0.831  -0.666  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.231   2.155   2.099  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.629   2.362   1.060  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.219   0.677   2.523  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.970  -0.116   0.984  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.016  -1.036   4.023  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.869  -2.311   2.797  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.642  -2.130   4.070  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.412  -3.146   2.422  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.136  -2.407   2.986  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1   18    3                                                  
CONECT    3    4   16    2                                                  
CONECT    4   10    3    5   23                                             
CONECT    5    4    6                                                       
CONECT    6    5    8    7                                                  
CONECT    7    6                                                            
CONECT    8    6   10    9   24                                             
CONECT    9    8   25   26   27                                             
CONECT   10    4    8   11   28                                             
CONECT   11   12   10   29   30                                             
CONECT   12   13   11   31   32                                             
CONECT   13   12   16   15   14                                             
CONECT   14   13   33   34   35                                             
CONECT   15   16   13                                                       
CONECT   16    3   13   17   15                                             
CONECT   17   16   18   36   37                                             
CONECT   18   19   17    2                                                  
CONECT   19   18                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    4                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   14                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   17                                                            
CONECT   37   17                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

RDKit          3D

37 40  0  0  0  0  0  0  0  0999 V2000
    1.6980   -1.6089   -1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -1.5559   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947   -0.5739    0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    0.8969    0.3587 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1945    1.2248   -0.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    2.3556   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    2.9310   -2.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5706    2.7754   -0.6412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6338    3.2856   -1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9604    1.4739    0.0519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8108    1.6731    1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414    0.3800    1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -0.6408    2.4831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3072   -1.5843    3.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -0.1607    3.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726   -1.0251    1.9529 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3645   -2.4071    2.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856   -2.7422    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -3.8341    0.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -0.8733   -2.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5886   -1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -1.4371   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.4142    1.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    3.5513    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    2.5511   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    4.1990   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    3.5163   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907    0.8313   -0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313    2.1552    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6294    2.3622    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.6767    2.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705   -0.1163    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -1.0364    4.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687   -2.3111    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -2.1301    4.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -3.1455    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -2.4074    2.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  4  1  0
  3  4  1  0
  3 16  1  0
 13 12  1  0
 12 11  1  0
  4  5  1  0
  5  6  1  0
  6  8  1  0
  8 10  1  0
 13 16  1  0
 18 19  2  0
 10 11  1  0
  2  1  1  0
 16 17  1  0
 16 15  1  1
 13 15  1  0
 17 18  1  0
  6  7  2  0
 18  2  1  0
 13 14  1  1
  2  3  2  0
  8  9  1  0
 12 31  1  0
 12 32  1  0
 11 29  1  0
 11 30  1  0
 17 36  1  0
 17 37  1  0
 10 28  1  6
  4 23  1  1
  8 24  1  1
  1 20  1  0
  1 21  1  0
  1 22  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(AlphaS,4S)-a,3,8-trimethyl-2-oxo-4b-hydroxy-8a,8aalpha-epoxy-1,2,4,5,6,7,8,8a-octahydroazulene-5a-acetate 5,4-lactone	Generator
(AlphaS,4S)-a,3,8-trimethyl-2-oxo-4b-hydroxy-8a,8aalpha-epoxy-1,2,4,5,6,7,8,8a-octahydroazulene-5a-acetic acid 5,4-lactone	Generator
(AlphaS,4S)-alpha,3,8-trimethyl-2-oxo-4beta-hydroxy-8alpha,8aalpha-epoxy-1,2,4,5,6,7,8,8a-octahydroazulene-5alpha-acetate 5,4-lactone	Generator
(AlphaS,4S)-α,3,8-trimethyl-2-oxo-4β-hydroxy-8α,8aalpha-epoxy-1,2,4,5,6,7,8,8a-octahydroazulene-5α-acetate 5,4-lactone	Generator
(AlphaS,4S)-α,3,8-trimethyl-2-oxo-4β-hydroxy-8α,8aalpha-epoxy-1,2,4,5,6,7,8,8a-octahydroazulene-5α-acetic acid 5,4-lactone	Generator

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

(1R,3S,6S,7S,10S)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-11-ene-8,13-dione

Traditional Name

(1R,3S,6S,7S,10S)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-11-ene-8,13-dione

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])C1=C2[C@@]3([H])OC(=O)[C@@]([H])(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]3(O[C@]23C([H])([H])C1=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C15H18O4/c1-7-9-4-5-14(3)15(19-14)6-10(16)8(2)11(15)12(9)18-13(7)17/h7,9,12H,4-6H2,1-3H3/t7-,9-,12-,14-,15+/m0/s1

InChI Key

RUBXBCDKYAQXTM-ZAHDETNWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Artemisia gorgonum	JEOL database	Macias, F. A., et al, J. Nat. Prod. 75, 1967 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Oxolane
Carboxylic acid ester
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.01	ALOGPS
logP	1.67	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	16.07	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.13 m³·mol⁻¹	ChemAxon
Polarizability	27.64 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

71608844

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Macias, F. A., et al. (2012). Macias, F. A., et al, J. Nat. Prod. 75, 1967 (2012). J. Nat. Prod..

Showing NP-Card for 1beta(R),10beta(S)-dioxa-isophotosantonin (NP0037058)

MOL for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

3D MOL for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

3D SDF for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

3D-SDF for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

PDB for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

3D PDB for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

SMILES for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

INCHI for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

Structure for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)

3D Structure for NP0037058 (1beta(R),10beta(S)-dioxa-isophotosantonin)