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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:45:15 UTC

Update Date

2021-09-23 19:45:15 UTC

HMDB ID

HMDB0302686

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Anisatin

Description

(1'S,2'R,3S,4'R,5'R,7'R,11'R)-4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on (1'S,2'R,3S,4'R,5'R,7'R,11'R)-4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0302686
     RDKit          3D
Anisatin
 43 46  0  0  0  0  0  0  0  0999 V2000
   -3.4075    0.3435   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -0.4866   -0.7677 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1347   -1.5679    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6586   -1.7907    0.6346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3993   -3.1429    0.3103 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -0.8792   -0.2876 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0181   -1.5064   -1.5663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090    0.2746   -0.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3615    1.0682   -1.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015    1.7114   -1.0792 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5111    2.6916   -0.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    2.2429    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1133    2.7254    2.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1463    1.1212    0.7320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3187    0.4501    1.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8945    0.8132   -0.4662 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5198    1.4852    0.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    0.7186   -1.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413   -0.5274   -0.0204 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0499   -1.0335    1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -2.2845    0.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484   -1.5861   -0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9837   -1.7272   -1.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1807    1.3365   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2064   -0.1656   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7917    0.4488    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -0.9735   -1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158   -2.4534   -0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7148   -1.2773    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402   -1.6964    1.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2663   -3.6984    1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -2.4885   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646    0.3435   -2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0285    1.8466   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    2.2993   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1468    1.6337    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560    0.9083    2.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059    1.2677    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0636    1.1069    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360    2.5919    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6134    1.4770   -1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -0.6219    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -0.9986    2.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 16 18  1  6
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
  8  2  1  0
 19 22  1  6
 19  6  1  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  1
  5 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  6
 14 36  1  6
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
M  END

  Mrv0541 02241220502D          

 23 26  0  0  1  0            999 V2000
   -0.9514   -1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -0.9938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4931   -1.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -0.9328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8502   -0.1417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0273   -0.1600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0084    0.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    1.3293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8558    1.3286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3018    0.6038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8680    1.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609    0.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8947    0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135   -0.7821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437    1.7748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8545    1.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3240    0.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.7018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073   -0.0822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3539   -0.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662   -0.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268   -1.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  6  0  0  0
 13 14  2  0  0  0  0
  9 15  1  1  0  0  0
  9 16  1  6  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
  5 22  1  6  0  0  0
  4 23  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302686

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1C[C@@H](O)[C@]2(O)[C@]3(COC3=O)[C@@](C)(O)[C@H]3C[C@@]12[C@@H](O)C(=O)O3

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8?,9+,12+,13+,14+,15-/m1/s1

> <INCHI_KEY>
GEVWHIDSUOMVRI-QHRGTXDDSA-N

> <FORMULA>
C15H20O8

> <MOLECULAR_WEIGHT>
328.3145

> <EXACT_MASS>
328.115817616

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.368209685560657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2'R,3S,4'R,5'R,7'R,8'R,11'R)-4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
-2.057976409

> <ALOGPS_LOGS>
-0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.726228295196805

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.01498940895532

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2698134866479807

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
71.9123

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.85e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anisatin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302686
     RDKit          3D
Anisatin
 43 46  0  0  0  0  0  0  0  0999 V2000
   -3.4075    0.3435   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -0.4866   -0.7677 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1347   -1.5679    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6586   -1.7907    0.6346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3993   -3.1429    0.3103 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -0.8792   -0.2876 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0181   -1.5064   -1.5663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090    0.2746   -0.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3615    1.0682   -1.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015    1.7114   -1.0792 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5111    2.6916   -0.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    2.2429    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1133    2.7254    2.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1463    1.1212    0.7320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3187    0.4501    1.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8945    0.8132   -0.4662 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5198    1.4852    0.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    0.7186   -1.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413   -0.5274   -0.0204 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0499   -1.0335    1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -2.2845    0.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484   -1.5861   -0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9837   -1.7272   -1.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1807    1.3365   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2064   -0.1656   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7917    0.4488    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -0.9735   -1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158   -2.4534   -0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7148   -1.2773    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402   -1.6964    1.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2663   -3.6984    1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -2.4885   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646    0.3435   -2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0285    1.8466   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    2.2993   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1468    1.6337    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560    0.9083    2.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059    1.2677    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0636    1.1069    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360    2.5919    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6134    1.4770   -1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -0.6219    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -0.9986    2.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 16 18  1  6
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
  8  2  1  0
 19 22  1  6
 19  6  1  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  1
  5 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  6
 14 36  1  6
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.776  -2.443   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.363  -1.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.920  -2.703   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.123  -1.741   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.587  -0.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.051  -0.299   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.016   1.078   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.001   2.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.597   2.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.430   1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.487   2.234   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.594   1.177   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.537   0.070   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.572  -1.460   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.635   4.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.882   3.313   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.595   2.558   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.471   1.247   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   1.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.694  -0.153   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.527  -1.437   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.110  -0.414   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.597  -2.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    5    2    7   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   15   16                                             
CONECT   10    9    5   11   13                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   10   14                                                  
CONECT   14   13                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17    8   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    6   21                                                  
CONECT   21   20                                                            
CONECT   22    5                                                            
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0302686
HETATM    1  C1  UNL     1      -3.407   0.344  -0.696  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.171  -0.487  -0.768  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.135  -1.568   0.320  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.659  -1.791   0.635  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.399  -3.143   0.310  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.041  -0.879  -0.288  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.018  -1.506  -1.566  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.909   0.275  -0.436  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.362   1.068  -1.588  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.901   1.711  -1.079  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.511   2.692  -0.139  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.206   2.243   0.951  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.113   2.725   2.119  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.146   1.121   0.732  1.00  0.00           C  
HETATM   15  O5  UNL     1      -1.319   0.450   1.934  1.00  0.00           O  
HETATM   16  C11 UNL     1       1.894   0.813  -0.466  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.520   1.485   0.769  1.00  0.00           C  
HETATM   18  O6  UNL     1       2.978   0.719  -1.379  1.00  0.00           O  
HETATM   19  C13 UNL     1       1.441  -0.527  -0.020  1.00  0.00           C  
HETATM   20  C14 UNL     1       2.050  -1.034   1.283  1.00  0.00           C  
HETATM   21  O7  UNL     1       2.174  -2.284   0.621  1.00  0.00           O  
HETATM   22  C15 UNL     1       2.348  -1.586  -0.535  1.00  0.00           C  
HETATM   23  O8  UNL     1       2.984  -1.727  -1.598  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.181   1.337  -1.170  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.206  -0.166  -1.273  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.792   0.449   0.336  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.092  -0.973  -1.765  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.616  -2.453  -0.122  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.715  -1.277   1.205  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.440  -1.696   1.697  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.266  -3.698   1.098  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.062  -2.488  -1.468  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.065   0.343  -2.380  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.028   1.847  -1.951  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.309   2.299  -1.955  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.147   1.634   0.564  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.956   0.908   2.523  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.606   1.268   0.834  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.064   1.107   1.707  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.436   2.592   0.687  1.00  0.00           H  
HETATM   41  H18 UNL     1       3.613   1.477  -1.243  1.00  0.00           H  
HETATM   42  H19 UNL     1       3.088  -0.622   1.400  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.415  -0.999   2.162  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    8   27
CONECT    3    4   28   29
CONECT    4    5    6   30
CONECT    5   31
CONECT    6    7    8   19
CONECT    7   32
CONECT    8    9   14
CONECT    9   10   33   34
CONECT   10   11   16   35
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   36
CONECT   15   37
CONECT   16   17   18   19
CONECT   17   38   39   40
CONECT   18   41
CONECT   19   20   22
CONECT   20   21   42   43
CONECT   21   22
CONECT   22   23   23
END

HMDB0302686
     RDKit          3D
Anisatin
 43 46  0  0  0  0  0  0  0  0999 V2000
   -3.4075    0.3435   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -0.4866   -0.7677 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1347   -1.5679    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6586   -1.7907    0.6346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3993   -3.1429    0.3103 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -0.8792   -0.2876 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0181   -1.5064   -1.5663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090    0.2746   -0.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3615    1.0682   -1.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015    1.7114   -1.0792 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5111    2.6916   -0.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    2.2429    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1133    2.7254    2.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1463    1.1212    0.7320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3187    0.4501    1.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8945    0.8132   -0.4662 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5198    1.4852    0.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    0.7186   -1.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413   -0.5274   -0.0204 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0499   -1.0335    1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -2.2845    0.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484   -1.5861   -0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9837   -1.7272   -1.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1807    1.3365   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2064   -0.1656   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7917    0.4488    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -0.9735   -1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158   -2.4534   -0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7148   -1.2773    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402   -1.6964    1.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2663   -3.6984    1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -2.4885   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646    0.3435   -2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0285    1.8466   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    2.2993   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1468    1.6337    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560    0.9083    2.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059    1.2677    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0636    1.1069    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360    2.5919    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6134    1.4770   -1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -0.6219    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -0.9986    2.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 16 18  1  6
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
  8  2  1  0
 19 22  1  6
 19  6  1  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  1
  5 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  6
 14 36  1  6
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₈

Average Molecular Weight

328.3145

Monoisotopic Molecular Weight

328.115817616

IUPAC Name

(1'S,2'R,3S,4'R,5'R,7'R,8'R,11'R)-4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione

Traditional Name

anisatin

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](O)[C@]2(O)[C@]3(COC3=O)[C@@](C)(O)[C@H]3C[C@@]12[C@@H](O)C(=O)O3

InChI Identifier

InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8?,9+,12+,13+,14+,15-/m1/s1

InChI Key

GEVWHIDSUOMVRI-QHRGTXDDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Prezizaane sesquiterpenoid
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Tertiary alcohol
Beta_propiolactone
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxetane
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

delta-lactone (CHEBI:2733 )
Sesquiterpenoids (C15) (C09294 )
Sesquiterpenes (C09294 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0302686)

Source

Exogenous

Exogenous (HMDB: HMDB0302686)

Food

Herb and spice

Spice

Star anise (FooDB: FOOD00090)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Analgesic (HMDB: HMDB0302686)
Sedative (HMDB: HMDB0302686)

Pharmaceutical industry

Convulsant (HMDB: HMDB0302686)

Biological role

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.89	ALOGPS
logP	-2.1	ChemAxon
logS	-0.62	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.91 m³·mol⁻¹	ChemAxon
Polarizability	30.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	172.915	32859911
AllCCS	[M+H-H2O]+	169.863	32859911
AllCCS	[M+Na]+	176.546	32859911
AllCCS	[M+NH4]+	175.737	32859911
AllCCS	[M-H]-	176.7	32859911
AllCCS	[M+Na-2H]-	176.142	32859911
AllCCS	[M+HCOO]-	175.661	32859911
DeepCCS	[M-2H]-	206.748	30932474
DeepCCS	[M+Na]+	181.253	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 10V, Positive-QTOF	splash10-01t9-0069000000-6d8e7b72d67c19cd4899	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 20V, Positive-QTOF	splash10-0iml-1097000000-fadbac971e115d279efb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 40V, Positive-QTOF	splash10-004i-2190000000-0392b618092024f50ec9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 10V, Negative-QTOF	splash10-000t-0091000000-5e062bee03594da803d7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 20V, Negative-QTOF	splash10-0560-0094000000-0313e82ffd16e0fad267	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 40V, Negative-QTOF	splash10-0a4l-4090000000-dba29c8311ff7b787582	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 10V, Positive-QTOF	splash10-004i-0009000000-8724071c891a6ff63929	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 20V, Positive-QTOF	splash10-004i-1049000000-416deff3a5dfaefb7a58	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 40V, Positive-QTOF	splash10-0a4l-9262000000-7494d46ec1a3e458b79e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 10V, Negative-QTOF	splash10-004i-0009000000-1da4882e25e8b2f24238	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 20V, Negative-QTOF	splash10-056r-2169000000-8219adba8c003449e2bc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisatin 40V, Negative-QTOF	splash10-014i-3692000000-9f5a0ed06c2d971a123c	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005800

KNApSAcK ID

Not Available

Chemspider ID

10283118

KEGG Compound ID

C09294

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

2733

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Anisatin (HMDB0302686)

MOL for HMDB0302686 (Anisatin)

3D MOL for HMDB0302686 (Anisatin)

3D SDF for HMDB0302686 (Anisatin)

3D-SDF for HMDB0302686 (Anisatin)

PDB for HMDB0302686 (Anisatin)

3D PDB for HMDB0302686 (Anisatin)

SMILES for HMDB0302686 (Anisatin)

INCHI for HMDB0302686 (Anisatin)

Structure for HMDB0302686 (Anisatin)

3D Structure for HMDB0302686 (Anisatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra