MiMeDB: Showing metabocard for 24-epi-6Î²,16Î²-diacetoxy-25-hydroxy-3,7-dioxo-29-nordammara-1,17(20)-diene-21,24-lactone (MMDBc0022721)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 12:47:47 UTC

Update Date

2022-08-31 06:47:44 UTC

Metabolite ID

MMDBc0022721

Metabolite Identification

Common Name

24-epi-6Î²,16Î²-diacetoxy-25-hydroxy-3,7-dioxo-29-nordammara-1,17(20)-diene-21,24-lactone

Description

24-epi-6beta,16beta-diacetoxy-25-hydroxy-3,7-dioxo-29-nordammara-1,17(20)-diene-21,24-lactone belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. 24-epi-6beta,16beta-diacetoxy-25-hydroxy-3,7-dioxo-29-nordammara-1,17(20)-diene-21,24-lactone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152114472D          

 49 53  0  0  1  0            999 V2000
    2.8473    3.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3061    3.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2519    4.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3181   -2.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4838    2.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    2.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1099    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4299    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6163   -0.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8185    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670    2.2989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9368    2.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9716    4.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2927    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9618    0.9421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0988    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    1.7614    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6625    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3054   -0.9851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7863    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7549    2.1537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2231    2.7844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4110    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9818   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -1.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4746    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6815    1.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1307    1.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7127    3.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594    4.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209    3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645   -0.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631   -1.1301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7915    2.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034    3.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4881   -1.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    2.9296    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3216    0.1997    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    1.1973    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1496    1.0873    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1226   -0.8723    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9428    2.0084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913    3.4151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 14 13  1  0  0  0  0
 16  1  1  6  0  0  0
 17  2  1  0  0  0  0
 18  3  1  0  0  0  0
 19  9  1  4  0  0  0
 20 10  1  0  0  0  0
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 21 16  1  0  0  0  0
 22 15  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 19  2  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 26 16  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 19  1  0  0  0  0
 30  4  1  0  0  0  0
 30  5  1  0  0  0  0
 24 30  1  6  0  0  0
 31  6  1  1  0  0  0
 31 14  1  0  0  0  0
 31 23  1  0  0  0  0
 31 26  1  0  0  0  0
 32  7  1  1  0  0  0
 32 15  1  0  0  0  0
 32 20  1  0  0  0  0
 33  8  1  6  0  0  0
 33 23  1  0  0  0  0
 33 28  1  0  0  0  0
 33 32  1  0  0  0  0
 34 17  2  0  0  0  0
 35 18  2  0  0  0  0
 36 21  2  0  0  0  0
 37 28  2  0  0  0  0
 38 29  2  0  0  0  0
 39 30  1  0  0  0  0
 40 17  1  0  0  0  0
 22 40  1  1  0  0  0
 41 18  1  0  0  0  0
 27 41  1  1  0  0  0
 42 24  1  0  0  0  0
 42 29  1  0  0  0  0
 16 43  1  1  0  0  0
 20 44  1  6  0  0  0
 22 45  1  6  0  0  0
 23 46  1  1  0  0  0
 24 47  1  1  0  0  0
 26 48  1  6  0  0  0
 27 49  1  6  0  0  0
M  END


  Mrv1652305152114472D          

 49 53  0  0  1  0            999 V2000
    2.8473    3.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3061    3.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2519    4.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3181   -2.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4838    2.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    2.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1099    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4299    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6163   -0.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8185    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670    2.2989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9368    2.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9716    4.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2927    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9618    0.9421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0988    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    1.7614    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6625    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3054   -0.9851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7863    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7549    2.1537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2231    2.7844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4110    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9818   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -1.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4746    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6815    1.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1307    1.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7127    3.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594    4.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209    3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645   -0.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631   -1.1301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7915    2.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034    3.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4881   -1.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    2.9296    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3216    0.1997    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    1.1973    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1496    1.0873    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1226   -0.8723    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9428    2.0084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913    3.4151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 14 13  1  0  0  0  0
 16  1  1  6  0  0  0
 17  2  1  0  0  0  0
 18  3  1  0  0  0  0
 19  9  1  4  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
 22 15  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 19  2  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 26 16  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 19  1  0  0  0  0
 30  4  1  0  0  0  0
 30  5  1  0  0  0  0
 24 30  1  6  0  0  0
 31  6  1  1  0  0  0
 31 14  1  0  0  0  0
 31 23  1  0  0  0  0
 31 26  1  0  0  0  0
 32  7  1  1  0  0  0
 32 15  1  0  0  0  0
 32 20  1  0  0  0  0
 33  8  1  6  0  0  0
 33 23  1  0  0  0  0
 33 28  1  0  0  0  0
 33 32  1  0  0  0  0
 34 17  2  0  0  0  0
 35 18  2  0  0  0  0
 36 21  2  0  0  0  0
 37 28  2  0  0  0  0
 38 29  2  0  0  0  0
 39 30  1  0  0  0  0
 40 17  1  0  0  0  0
 22 40  1  1  0  0  0
 41 18  1  0  0  0  0
 27 41  1  1  0  0  0
 42 24  1  0  0  0  0
 42 29  1  0  0  0  0
 16 43  1  1  0  0  0
 20 44  1  6  0  0  0
 22 45  1  6  0  0  0
 23 46  1  1  0  0  0
 24 47  1  1  0  0  0
 26 48  1  6  0  0  0
 27 49  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0022721

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(C[C@@]2(C)[C@@]([H])(CC[C@@]3([H])[C@@]4(C)CCC(=O)[C@@]([H])(C)[C@]4([H])[C@]([H])(OC(C)=O)C(=O)[C@]23C)C1=C1CC[C@]([H])(OC1=O)C(C)(C)O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H46O9/c1-16-21(36)13-14-31(6)23-11-10-20-25(19-9-12-24(30(4,5)39)42-29(19)38)22(40-17(2)34)15-32(20,7)33(23,8)28(37)27(26(16)31)41-18(3)35/h16,20,22-24,26-27,39H,9-15H2,1-8H3/t16-,20+,22+,23+,24+,26-,27+,31-,32+,33-/m1/s1

> <INCHI_KEY>
WTHKHCCTZZPZPB-JIGOLBMKSA-N

> <FORMULA>
C33H46O9

> <MOLECULAR_WEIGHT>
586.722

> <EXACT_MASS>
586.314183061

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
64.18022351360113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,6S,7S,8S,10S,11S,13S,15R)-8-(acetyloxy)-14-[(6S)-6-(2-hydroxypropan-2-yl)-2-oxooxan-3-ylidene]-2,6,10,11-tetramethyl-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
3.854288372666666

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.80494988774833

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.30026355027114

> <JCHEM_PKA_STRONGEST_BASIC>
-3.10426765528183

> <JCHEM_POLAR_SURFACE_AREA>
133.27

> <JCHEM_REFRACTIVITY>
151.72090000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,7S,8S,10S,11S,13S,15R)-8-(acetyloxy)-14-[(6S)-6-(2-hydroxypropan-2-yl)-2-oxooxan-3-ylidene]-2,6,10,11-tetramethyl-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       5.315   5.740   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.305   6.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.337   9.272   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.060  -4.270   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.899  -4.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.229   1.123   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.903   4.702   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.336   4.904   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.805   0.803   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.803   0.581   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.713   0.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.750  -0.412   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.261   1.666   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.745   1.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.488   4.152   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.792   4.291   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.482   5.327   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.814   7.823   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.280   0.593   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.795   1.759   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.785   3.114   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.763   3.288   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.237   2.301   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.170  -1.839   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.334   1.809   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.276   4.020   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.283   5.197   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.767   4.926   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.699  -0.834   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.115  -3.055   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.753   2.572   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.272   3.207   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.244   3.478   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.930   5.850   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.298   7.552   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.300   3.385   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.226   6.104   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.174  -1.044   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -8.331  -2.109   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -5.211   3.811   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       2.806   6.646   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -4.645  -2.050   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0       3.799   5.469   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.467   0.373   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.886   2.235   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.279   2.030   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -7.696  -1.628   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.760   3.749   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.290   6.375   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   30                                                            
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7   32                                                            
CONECT    8   33                                                            
CONECT    9   12   19                                                       
CONECT   10   11   20                                                       
CONECT   11   10   23                                                       
CONECT   12    9   24                                                       
CONECT   13   14   21                                                       
CONECT   14   13   31                                                       
CONECT   15   22   32                                                       
CONECT   16    1   21   26   43                                             
CONECT   17    2   34   40                                                  
CONECT   18    3   35   41                                                  
CONECT   19    9   25   29                                                  
CONECT   20   10   25   32   44                                             
CONECT   21   13   16   36                                                  
CONECT   22   15   25   40   45                                             
CONECT   23   11   31   33   46                                             
CONECT   24   12   30   42   47                                             
CONECT   25   19   20   22                                                  
CONECT   26   16   27   31   48                                             
CONECT   27   26   28   41   49                                             
CONECT   28   27   33   37                                                  
CONECT   29   19   38   42                                                  
CONECT   30    4    5   24   39                                             
CONECT   31    6   14   23   26                                             
CONECT   32    7   15   20   33                                             
CONECT   33    8   23   28   32                                             
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   21                                                            
CONECT   37   28                                                            
CONECT   38   29                                                            
CONECT   39   30                                                            
CONECT   40   17   22                                                       
CONECT   41   18   27                                                       
CONECT   42   24   29                                                       
CONECT   43   16                                                            
CONECT   44   20                                                            
CONECT   45   22                                                            
CONECT   46   23                                                            
CONECT   47   24                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

Synonyms

Value	Source
24-Epi-6b,16b-diacetoxy-25-hydroxy-3,7-dioxo-29-nordammara-1,17(20)-diene-21,24-lactone	Generator
24-Epi-6β,16β-diacetoxy-25-hydroxy-3,7-dioxo-29-nordammara-1,17(20)-diene-21,24-lactone	Generator

Molecular Formula

C₃₃H₄₆O₉

Average Mass

586.722

Monoisotopic Mass

586.314183061

IUPAC Name

(1S,2R,6S,7S,8S,10S,11S,13S,15R)-8-(acetyloxy)-14-[(6S)-6-(2-hydroxypropan-2-yl)-2-oxooxan-3-ylidene]-2,6,10,11-tetramethyl-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

Traditional Name

(1S,2R,6S,7S,8S,10S,11S,13S,15R)-8-(acetyloxy)-14-[(6S)-6-(2-hydroxypropan-2-yl)-2-oxooxan-3-ylidene]-2,6,10,11-tetramethyl-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C[C@@]2(C)[C@@]([H])(CC[C@@]3([H])[C@@]4(C)CCC(=O)[C@@]([H])(C)[C@]4([H])[C@]([H])(OC(C)=O)C(=O)[C@]23C)C1=C1CC[C@]([H])(OC1=O)C(C)(C)O)OC(C)=O

InChI Identifier

InChI=1S/C33H46O9/c1-16-21(36)13-14-31(6)23-11-10-20-25(19-9-12-24(30(4,5)39)42-29(19)38)22(40-17(2)34)15-32(20,7)33(23,8)28(37)27(26(16)31)41-18(3)35/h16,20,22-24,26-27,39H,9-15H2,1-8H3/t16-,20+,22+,23+,24+,26-,27+,31-,32+,33-/m1/s1

InChI Key

WTHKHCCTZZPZPB-JIGOLBMKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
Steroid ester
3-oxo-5-alpha-steroid
7-oxosteroid
Oxosteroid
3-oxosteroid
Tricarboxylic acid or derivatives
Alpha-acyloxy ketone
Delta_valerolactone
Delta valerolactone
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0033 g/L	ALOGPS
logP	3.02	ALOGPS
logP	3.85	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	133.27 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	151.72 m³·mol⁻¹	ChemAxon
Polarizability	64.18 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human sputum; Human	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590100

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 24-epi-6Î²,16Î²-diacetoxy-25-hydroxy-3,7-dioxo-29-nordammara-1,17(20)-diene-21,24-lactone (MMDBc0022721)

MOL for #<Metabolite:0x0000559d04f44538>

3D MOL for #<Metabolite:0x0000559d04f44538>

3D SDF for #<Metabolite:0x0000559d04f44538>

3D-SDF for #<Metabolite:0x0000559d04f44538>

PDB for #<Metabolite:0x0000559d04f44538>

3D PDB for #<Metabolite:0x0000559d04f44538>

SMILES for #<Metabolite:0x0000559d04f44538>

INCHI for #<Metabolite:0x0000559d04f44538>

Structure for #<Metabolite:0x0000559d04f44538>

3D Structure for #<Metabolite:0x0000559d04f44538>