Hmdb loader

Showing metabocard for Arteannuin B (HMDB0248616)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 02:02:45 UTC
Update Date2021-09-26 22:58:59 UTC
HMDB IDHMDB0248616
Secondary Accession NumbersNone
Metabolite Identification
Common NameArteannuin B
DescriptionArteannuin B belongs to the class of organic compounds known as cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan. Based on a literature review a significant number of articles have been published on Arteannuin B. This compound has been identified in human blood as reported by (PMID: 31557052 ). Arteannuin b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Arteannuin B is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0248616 (Arteannuin B)


  Mrv1533004191516222D          

 18 21  0  0  0  0            999 V2000
    0.0588   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1051    0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227    1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423    1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5204    1.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574    2.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075    1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700    2.0868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731    0.8786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5340    0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062   -0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024   -0.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1731    0.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3536    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
Download

3D MOL for HMDB0248616 (Arteannuin B)

HMDB0248616
     RDKit          3D
Arteannuin B
 38 41  0  0  0  0  0  0  0  0999 V2000
    0.5360    3.7591   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339    2.6722    0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189    2.4347    1.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223    3.3108    2.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236    1.0804    1.9142 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963    0.3936    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3168    1.3771   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213    1.4851   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2923    0.1056   -0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857   -0.9300    0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3961   -2.2643   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -0.9234    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -2.0212    0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962   -1.4389   -1.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858   -0.5662   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -1.2092   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2419    0.7892   -0.5453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036    0.2561    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    4.6023    0.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697    3.7905   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1765    1.3001   -1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1199    2.1910   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419    1.8202    0.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    0.1585   -0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772   -0.1285   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7169   -0.7604    1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110   -2.1765   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -2.4100   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2599   -3.1071    0.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456   -1.2496    1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3234   -2.8550   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793   -2.4738    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -2.3375   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -0.9848   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3203   -0.7671   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7760   -1.1162    1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -2.3048   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    0.4979    1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  7  2  1  0
 18 15  1  0
 12  6  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
M  END
Download

3D SDF for HMDB0248616 (Arteannuin B)


  Mrv1533004191516222D          

 18 21  0  0  0  0            999 V2000
    0.0588   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1051    0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227    1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423    1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5204    1.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574    2.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075    1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700    2.0868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731    0.8786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5340    0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062   -0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024   -0.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1731    0.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3536    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248616

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(=C)C(=O)OC22C3OC3(C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8,10-11,13H,2,4-7H2,1,3H3

> <INCHI_KEY>
QWQSMEDUZQDVLA-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.02169846244016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0¹,⁵.0¹²,¹⁴]tetradecan-3-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.8475120716666664

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.244929433355257

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
65.7315

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0¹,⁵.0¹²,¹⁴]tetradecan-3-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0248616 (Arteannuin B)

HMDB0248616
     RDKit          3D
Arteannuin B
 38 41  0  0  0  0  0  0  0  0999 V2000
    0.5360    3.7591   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339    2.6722    0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189    2.4347    1.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223    3.3108    2.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236    1.0804    1.9142 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963    0.3936    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3168    1.3771   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213    1.4851   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2923    0.1056   -0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857   -0.9300    0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3961   -2.2643   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -0.9234    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -2.0212    0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962   -1.4389   -1.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858   -0.5662   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -1.2092   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2419    0.7892   -0.5453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036    0.2561    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    4.6023    0.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697    3.7905   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1765    1.3001   -1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1199    2.1910   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419    1.8202    0.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    0.1585   -0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772   -0.1285   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7169   -0.7604    1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110   -2.1765   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -2.4100   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2599   -3.1071    0.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456   -1.2496    1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3234   -2.8550   -0.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793   -2.4738    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -2.3375   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -0.9848   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3203   -0.7671   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7760   -1.1162    1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -2.3048   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    0.4979    1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  7  2  1  0
 18 15  1  0
 12  6  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
M  END
Download

PDB for HMDB0248616 (Arteannuin B)

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.110  -2.056   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.722  -0.643   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.196   0.593   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.416   2.007   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.946   2.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.838   3.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.347   4.898   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.307   2.977   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.544   3.895   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.243   1.640   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.864   0.947   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.252  -0.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.169  -1.703   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.699  -1.526   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.311  -0.113   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -0.725   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.923   1.300   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.393   1.123   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12   18                                             
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11   15                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END
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3D PDB for HMDB0248616 (Arteannuin B)

COMPND    HMDB0248616
HETATM    1  C1  UNL     1       0.536   3.759  -0.316  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.134   2.672   0.302  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.019   2.435   1.736  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.122   3.311   2.655  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.224   1.080   1.914  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.096   0.394   0.691  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.317   1.377  -0.325  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.821   1.485  -0.452  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.292   0.106  -0.846  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.986  -0.930   0.183  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.396  -2.264  -0.418  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.575  -0.923   0.683  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.274  -2.021   0.046  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.196  -1.439  -1.024  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.186  -0.566  -0.327  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.543  -1.209  -0.007  1.00  0.00           C  
HETATM   17  O3  UNL     1       2.242   0.789  -0.545  1.00  0.00           O  
HETATM   18  C15 UNL     1       1.604   0.256   0.684  1.00  0.00           C  
HETATM   19  H1  UNL     1       0.825   4.602   0.284  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.570   3.791  -1.390  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.177   1.300  -1.307  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.120   2.191  -1.229  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.242   1.820   0.515  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.400   0.158  -0.953  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.877  -0.128  -1.836  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.717  -0.760   1.029  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.511  -2.176  -0.585  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.977  -2.410  -1.439  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.260  -3.107   0.255  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.646  -1.250   1.768  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.323  -2.855  -0.332  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.979  -2.474   0.805  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.738  -2.338  -1.441  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.659  -0.985  -1.851  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.320  -0.767  -0.661  1.00  0.00           H  
HETATM   36  H18 UNL     1       3.776  -1.116   1.073  1.00  0.00           H  
HETATM   37  H19 UNL     1       3.506  -2.305  -0.233  1.00  0.00           H  
HETATM   38  H20 UNL     1       2.182   0.498   1.593  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   12   18
CONECT    7    8   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11   12   26
CONECT   11   27   28   29
CONECT   12   13   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   17   18
CONECT   16   35   36   37
CONECT   17   18
CONECT   18   38
END
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SMILES for HMDB0248616 (Arteannuin B)

CC1CCC2C(=C)C(=O)OC22C3OC3(C)CCC12
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INCHI for HMDB0248616 (Arteannuin B)

InChI=1S/C15H20O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8,10-11,13H,2,4-7H2,1,3H3
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC15H20O3
Average Molecular Weight248.322
Monoisotopic Molecular Weight248.141244504
IUPAC Name8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0¹,⁵.0¹²,¹⁴]tetradecan-3-one
Traditional Name8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0¹,⁵.0¹²,¹⁴]tetradecan-3-one
CAS Registry NumberNot Available
SMILES
CC1CCC2C(=C)C(=O)OC22C3OC3(C)CCC12
InChI Identifier
InChI=1S/C15H20O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8,10-11,13H,2,4-7H2,1,3H3
InChI KeyQWQSMEDUZQDVLA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentCadinanolides
Alternative Parents
Substituents
  • Cadinanolide skeleton
  • Sesquiterpenoid
  • Oxepane
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.65ALOGPS
logP2.85ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.83 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.73 m³·mol⁻¹ChemAxon
Polarizability27.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-191.67930932474
DeepCCS[M+Na]+167.24430932474
AllCCS[M+H]+157.532859911
AllCCS[M+H-H2O]+153.832859911
AllCCS[M+NH4]+160.932859911
AllCCS[M+Na]+161.932859911
AllCCS[M-H]-164.532859911
AllCCS[M+Na-2H]-164.232859911
AllCCS[M+HCOO]-164.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202213.6795 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.28 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2218.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid349.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid171.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid181.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid145.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid720.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid764.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)74.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1104.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid393.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1327.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid445.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid385.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate414.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA338.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water45.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Arteannuin BCC1CCC2C(=C)C(=O)OC22C3OC3(C)CCC122788.8Standard polar33892256
Arteannuin BCC1CCC2C(=C)C(=O)OC22C3OC3(C)CCC121879.4Standard non polar33892256
Arteannuin BCC1CCC2C(=C)C(=O)OC22C3OC3(C)CCC122073.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Arteannuin B GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-9240000000-62cf1887a16b77229e382021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Arteannuin B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteannuin B 10V, Positive-QTOFsplash10-0002-0090000000-308c6024b53a399d0d742021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteannuin B 20V, Positive-QTOFsplash10-0002-0090000000-d5c3e282e530931fef842021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteannuin B 40V, Positive-QTOFsplash10-002e-3970000000-f8fc99159b01e54493de2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteannuin B 10V, Negative-QTOFsplash10-0002-0090000000-7b3a58b796a0e42639592021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteannuin B 20V, Negative-QTOFsplash10-0002-0090000000-7a435c47c5da5d10fc1d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteannuin B 40V, Negative-QTOFsplash10-0fvj-1590000000-da56e1aecae4e48cf64e2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID467128
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound536300
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]