NP-MRD: Showing NP-Card for 11beta,13-dihydromikamicranolide (NP0027133)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 18:50:30 UTC

Updated at

2021-06-29 23:53:04 UTC

NP-MRD ID

NP0027133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11beta,13-dihydromikamicranolide

Provided By

JEOL Database JEOL Logo

Description

11beta,13-dihydromikamicranolide is found in Mikania micrantha. 11beta,13-dihydromikamicranolide was first documented in 2004 (Huang, H., et al.). Based on a literature review very few articles have been published on 11beta,13-Dihydromikamicranolide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120503D          

 40 44  0  0  0  0            999 V2000
   -0.2442   -4.4705    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -3.5880   -0.3348 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9983   -3.8346   -1.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -4.9203   -2.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -2.6532   -2.4687 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -1.5851   -1.5179 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7094   -0.3283   -2.1548 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6715    0.8990   -1.2359 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3509    2.1475   -2.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.7471   -0.0721 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5456    0.1704    1.0320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0470    0.5902    2.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    0.7934    0.7461 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9195   -0.1536    1.1121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -1.3876    1.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2400   -1.5551    2.9732 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8737   -2.1197    3.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678   -2.6177    4.2257 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -1.9932    2.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -1.3443    1.0237 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5396   -2.0832   -0.2981 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9760    1.0641   -0.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138   -4.2699   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479   -4.3290    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -5.5292    0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8134   -3.8252    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.4455   -1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -0.1052   -3.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933   -0.5388   -2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904    2.2924   -2.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    2.0851   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947    3.0485   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    0.1535   -0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826    1.7298    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.0841    2.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887    1.7249    1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844   -2.2000    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -2.2678    3.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.6106    3.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404   -1.9958   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
 11 10  1  0  0  0  0
 21  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
 10  8  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
  8 22  1  0  0  0  0
 11 12  1  1  0  0  0
  8  7  1  0  0  0  0
 20 21  1  0  0  0  0
 13 22  1  0  0  0  0
  6 21  1  0  0  0  0
 11 13  1  0  0  0  0
  3  4  2  0  0  0  0
 17 18  2  0  0  0  0
  8  9  1  6  0  0  0
  7  6  1  0  0  0  0
 13 36  1  1  0  0  0
 13 14  1  0  0  0  0
 21 40  1  6  0  0  0
 15 14  1  0  0  0  0
  2  1  1  0  0  0  0
 20 19  1  1  0  0  0
  6  5  1  0  0  0  0
  2 26  1  1  0  0  0
  6 27  1  1  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 15 37  1  6  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 12 35  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  END

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -0.2442   -4.4705    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -3.5880   -0.3348 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9983   -3.8346   -1.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -4.9203   -2.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -2.6532   -2.4687 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -1.5851   -1.5179 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7094   -0.3283   -2.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6715    0.8990   -1.2359 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3509    2.1475   -2.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.7471   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    0.1704    1.0320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0470    0.5902    2.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    0.7934    0.7461 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9195   -0.1536    1.1121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -1.3876    1.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2400   -1.5551    2.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737   -2.1197    3.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678   -2.6177    4.2257 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -1.9932    2.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -1.3443    1.0237 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5396   -2.0832   -0.2981 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9760    1.0641   -0.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138   -4.2699   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479   -4.3290    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -5.5292    0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8134   -3.8252    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.4455   -1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -0.1052   -3.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933   -0.5388   -2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904    2.2924   -2.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    2.0851   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947    3.0485   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    0.1535   -0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826    1.7298    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.0841    2.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887    1.7249    1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844   -2.2000    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -2.2678    3.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.6106    3.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404   -1.9958   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 11  1  0
 20 15  1  0
 11 10  1  0
 21  2  1  0
  2  3  1  0
  3  5  1  0
 10  8  1  0
 15 16  1  0
 16 17  1  0
 17 19  1  0
  8 22  1  0
 11 12  1  1
  8  7  1  0
 20 21  1  0
 13 22  1  0
  6 21  1  0
 11 13  1  0
  3  4  2  0
 17 18  2  0
  8  9  1  6
  7  6  1  0
 13 36  1  1
 13 14  1  0
 21 40  1  6
 15 14  1  0
  2  1  1  0
 20 19  1  1
  6  5  1  0
  2 26  1  1
  6 27  1  1
  7 28  1  0
  7 29  1  0
 10 33  1  0
 10 34  1  0
 15 37  1  6
 16 38  1  0
 16 39  1  0
 12 35  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END


  Mrv1652306192120503D          

 40 44  0  0  0  0            999 V2000
   -0.2442   -4.4705    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -3.5880   -0.3348 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9983   -3.8346   -1.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -4.9203   -2.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -2.6532   -2.4687 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -1.5851   -1.5179 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7094   -0.3283   -2.1548 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6715    0.8990   -1.2359 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3509    2.1475   -2.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.7471   -0.0721 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5456    0.1704    1.0320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0470    0.5902    2.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    0.7934    0.7461 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9195   -0.1536    1.1121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -1.3876    1.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2400   -1.5551    2.9732 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8737   -2.1197    3.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678   -2.6177    4.2257 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -1.9932    2.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -1.3443    1.0237 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5396   -2.0832   -0.2981 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9760    1.0641   -0.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138   -4.2699   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479   -4.3290    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -5.5292    0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8134   -3.8252    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.4455   -1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -0.1052   -3.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933   -0.5388   -2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904    2.2924   -2.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    2.0851   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947    3.0485   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    0.1535   -0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826    1.7298    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.0841    2.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887    1.7249    1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844   -2.2000    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -2.2678    3.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.6106    3.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404   -1.9958   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
 11 10  1  0  0  0  0
 21  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
 10  8  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
  8 22  1  0  0  0  0
 11 12  1  1  0  0  0
  8  7  1  0  0  0  0
 20 21  1  0  0  0  0
 13 22  1  0  0  0  0
  6 21  1  0  0  0  0
 11 13  1  0  0  0  0
  3  4  2  0  0  0  0
 17 18  2  0  0  0  0
  8  9  1  6  0  0  0
  7  6  1  0  0  0  0
 13 36  1  1  0  0  0
 13 14  1  0  0  0  0
 21 40  1  6  0  0  0
 15 14  1  0  0  0  0
  2  1  1  0  0  0  0
 20 19  1  1  0  0  0
  6  5  1  0  0  0  0
  2 26  1  1  0  0  0
  6 27  1  1  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 15 37  1  6  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 12 35  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C([H])([H])[C@]3(O[C@]1([H])O[C@@]1([H])C([H])([H])C(=O)O[C@@]21[C@]1([H])[C@]([H])(C(=O)O[C@@]1([H])C3([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O7/c1-6-10-7(19-11(6)17)4-13(2)5-14(18)12(22-13)20-8-3-9(16)21-15(8,10)14/h6-8,10,12,18H,3-5H2,1-2H3/t6-,7+,8+,10-,12+,13+,14+,15+/m1/s1

> <INCHI_KEY>
YWKBPMIFYCPBKO-APWQAVBJSA-N

> <FORMULA>
C15H18O7

> <MOLECULAR_WEIGHT>
310.302

> <EXACT_MASS>
310.10525292

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.07624077514858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,7R,8R,9R,12S,14S,16R)-16-hydroxy-9,14-dimethyl-2,6,11,17-tetraoxapentacyclo[12.2.1.0^{3,7}.0^{7,16}.0^{8,12}]heptadecane-5,10-dione

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
-0.38402517466666675

> <ALOGPS_LOGS>
-1.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.830864891908533

> <JCHEM_PKA_STRONGEST_BASIC>
-4.08132660578862

> <JCHEM_POLAR_SURFACE_AREA>
91.29000000000002

> <JCHEM_REFRACTIVITY>
68.185

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,7R,8R,9R,12S,14S,16R)-16-hydroxy-9,14-dimethyl-2,6,11,17-tetraoxapentacyclo[12.2.1.0^{3,7}.0^{7,16}.0^{8,12}]heptadecane-5,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -0.2442   -4.4705    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -3.5880   -0.3348 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9983   -3.8346   -1.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -4.9203   -2.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -2.6532   -2.4687 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -1.5851   -1.5179 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7094   -0.3283   -2.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6715    0.8990   -1.2359 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3509    2.1475   -2.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.7471   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    0.1704    1.0320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0470    0.5902    2.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    0.7934    0.7461 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9195   -0.1536    1.1121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -1.3876    1.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2400   -1.5551    2.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737   -2.1197    3.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678   -2.6177    4.2257 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -1.9932    2.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -1.3443    1.0237 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5396   -2.0832   -0.2981 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9760    1.0641   -0.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138   -4.2699   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479   -4.3290    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -5.5292    0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8134   -3.8252    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.4455   -1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -0.1052   -3.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933   -0.5388   -2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904    2.2924   -2.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    2.0851   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947    3.0485   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    0.1535   -0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826    1.7298    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.0841    2.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887    1.7249    1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844   -2.2000    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -2.2678    3.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.6106    3.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404   -1.9958   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 11  1  0
 20 15  1  0
 11 10  1  0
 21  2  1  0
  2  3  1  0
  3  5  1  0
 10  8  1  0
 15 16  1  0
 16 17  1  0
 17 19  1  0
  8 22  1  0
 11 12  1  1
  8  7  1  0
 20 21  1  0
 13 22  1  0
  6 21  1  0
 11 13  1  0
  3  4  2  0
 17 18  2  0
  8  9  1  6
  7  6  1  0
 13 36  1  1
 13 14  1  0
 21 40  1  6
 15 14  1  0
  2  1  1  0
 20 19  1  1
  6  5  1  0
  2 26  1  1
  6 27  1  1
  7 28  1  0
  7 29  1  0
 10 33  1  0
 10 34  1  0
 15 37  1  6
 16 38  1  0
 16 39  1  0
 12 35  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.244  -4.471   0.248  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.851  -3.588  -0.335  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.998  -3.835  -1.817  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.969  -4.920  -2.371  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.192  -2.653  -2.469  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.297  -1.585  -1.518  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.709  -0.328  -2.155  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.672   0.899  -1.236  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.351   2.147  -2.059  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.306   0.747  -0.072  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.546   0.170   1.032  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.047   0.590   2.305  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.912   0.793   0.746  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.920  -0.154   1.112  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.301  -1.388   1.471  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.240  -1.555   2.973  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.874  -2.120   3.189  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.468  -2.618   4.226  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.104  -1.993   2.067  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.848  -1.344   1.024  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.540  -2.083  -0.298  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.976   1.064  -0.657  0.00  0.00           O+0
HETATM   23  H   UNK     0      -1.214  -4.270  -0.221  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.348  -4.329   1.327  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.018  -5.529   0.079  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.813  -3.825   0.128  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.366  -1.446  -1.319  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.324  -0.105  -3.038  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.293  -0.539  -2.551  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.090   2.292  -2.855  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.643   2.085  -2.513  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.395   3.049  -1.437  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.194   0.154  -0.310  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.683   1.730   0.244  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.769   0.084   2.489  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.089   1.725   1.294  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.884  -2.200   1.031  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.995  -2.268   3.316  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.346  -0.611   3.514  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.540  -1.996  -0.489  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2   21    3    1   26                                             
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6   21    7    5   27                                             
CONECT    7    8    6   28   29                                             
CONECT    8   10   22    7    9                                             
CONECT    9    8   30   31   32                                             
CONECT   10   11    8   33   34                                             
CONECT   11   20   10   12   13                                             
CONECT   12   11   35                                                       
CONECT   13   22   11   36   14                                             
CONECT   14   13   15                                                       
CONECT   15   20   16   14   37                                             
CONECT   16   15   17   38   39                                             
CONECT   17   16   19   18                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   11   15   21   19                                             
CONECT   21    2   20    6   40                                             
CONECT   22    8   13                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   16                                                            
CONECT   40   21                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

RDKit          3D

40 44  0  0  0  0  0  0  0  0999 V2000
   -0.2442   -4.4705    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -3.5880   -0.3348 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9983   -3.8346   -1.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -4.9203   -2.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -2.6532   -2.4687 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -1.5851   -1.5179 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7094   -0.3283   -2.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6715    0.8990   -1.2359 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3509    2.1475   -2.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.7471   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    0.1704    1.0320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0470    0.5902    2.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    0.7934    0.7461 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9195   -0.1536    1.1121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -1.3876    1.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2400   -1.5551    2.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737   -2.1197    3.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678   -2.6177    4.2257 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -1.9932    2.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -1.3443    1.0237 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5396   -2.0832   -0.2981 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9760    1.0641   -0.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138   -4.2699   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479   -4.3290    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -5.5292    0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8134   -3.8252    0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.4455   -1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -0.1052   -3.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933   -0.5388   -2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904    2.2924   -2.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    2.0851   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947    3.0485   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    0.1535   -0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6826    1.7298    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.0841    2.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0887    1.7249    1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844   -2.2000    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -2.2678    3.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.6106    3.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404   -1.9958   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 11  1  0
 20 15  1  0
 11 10  1  0
 21  2  1  0
  2  3  1  0
  3  5  1  0
 10  8  1  0
 15 16  1  0
 16 17  1  0
 17 19  1  0
  8 22  1  0
 11 12  1  1
  8  7  1  0
 20 21  1  0
 13 22  1  0
  6 21  1  0
 11 13  1  0
  3  4  2  0
 17 18  2  0
  8  9  1  6
  7  6  1  0
 13 36  1  1
 13 14  1  0
 21 40  1  6
 15 14  1  0
  2  1  1  0
 20 19  1  1
  6  5  1  0
  2 26  1  1
  6 27  1  1
  7 28  1  0
  7 29  1  0
 10 33  1  0
 10 34  1  0
 15 37  1  6
 16 38  1  0
 16 39  1  0
 12 35  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END

View in JSmol

Synonyms

Value	Source
11b,13-Dihydromikamicranolide	Generator
11Β,13-dihydromikamicranolide	Generator

Chemical Formula

C₁₅H₁₈O₇

Average Mass

310.3020 Da

Monoisotopic Mass

310.10525 Da

IUPAC Name

(1S,3S,7R,8R,9R,12S,14S,16R)-16-hydroxy-9,14-dimethyl-2,6,11,17-tetraoxapentacyclo[12.2.1.0^{3,7}.0^{7,16}.0^{8,12}]heptadecane-5,10-dione

Traditional Name

(1S,3S,7R,8R,9R,12S,14S,16R)-16-hydroxy-9,14-dimethyl-2,6,11,17-tetraoxapentacyclo[12.2.1.0^{3,7}.0^{7,16}.0^{8,12}]heptadecane-5,10-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12C([H])([H])[C@]3(O[C@]1([H])O[C@@]1([H])C([H])([H])C(=O)O[C@@]21[C@]1([H])[C@]([H])(C(=O)O[C@@]1([H])C3([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H18O7/c1-6-10-7(19-11(6)17)4-13(2)5-14(18)12(22-13)20-8-3-9(16)21-15(8,10)14/h6-8,10,12,18H,3-5H2,1-2H3/t6-,7+,8+,10-,12+,13+,14+,15+/m1/s1

InChI Key

YWKBPMIFYCPBKO-APWQAVBJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mikania micrantha	JEOL database	Huang, H., et al, J. Nat. Prod. 67, 734 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	0.16	ALOGPS
logP	-0.38	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	11.83	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.18 m³·mol⁻¹	ChemAxon
Polarizability	29.08 Å³	ChemAxon
Number of Rings	5	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

10189070

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21578069

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang, H., et al. (2004). Huang, H., et al, J. Nat. Prod. 67, 734 (2004). J. Nat. Prod..

Showing NP-Card for 11beta,13-dihydromikamicranolide (NP0027133)

MOL for NP0027133 (11beta,13-dihydromikamicranolide)

3D MOL for NP0027133 (11beta,13-dihydromikamicranolide)

3D SDF for NP0027133 (11beta,13-dihydromikamicranolide)

3D-SDF for NP0027133 (11beta,13-dihydromikamicranolide)

PDB for NP0027133 (11beta,13-dihydromikamicranolide)

3D PDB for NP0027133 (11beta,13-dihydromikamicranolide)

SMILES for NP0027133 (11beta,13-dihydromikamicranolide)

INCHI for NP0027133 (11beta,13-dihydromikamicranolide)

Structure for NP0027133 (11beta,13-dihydromikamicranolide)

3D Structure for NP0027133 (11beta,13-dihydromikamicranolide)