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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:13:31 UTC

Update Date

2022-03-07 02:56:18 UTC

HMDB ID

HMDB0039696

Secondary Accession Numbers

HMDB39696

Metabolite Identification

Common Name

25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A

Description

25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A, also known as hycanthon or etrenol, belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 05061311192D          

 37 43  0  0  0  0            999 V2000
    0.1296    1.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2747    0.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2762   -1.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -2.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1936   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    0.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038   -1.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3318    0.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5181    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6769   -1.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0557   -2.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972    0.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8558    0.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7523   -0.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282   -0.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0900   -1.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -1.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6728    0.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6473   -0.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7621   -2.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8927   -0.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660   -0.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8847   -1.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -2.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3681   -0.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6823   -1.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8002   -1.9127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3818    0.4877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744   -3.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4861   -0.6652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927   -2.7517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    0.7717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368   -0.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -2.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5170   -1.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 11 10  1  0  0  0  0
 13  1  1  0  0  0  0
 14  6  2  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17  7  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 23  2  1  0  0  0  0
 23 12  1  0  0  0  0
 23 13  1  0  0  0  0
 23 20  1  0  0  0  0
 24  3  1  0  0  0  0
 24 14  1  0  0  0  0
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 25  4  1  0  0  0  0
 25 18  1  0  0  0  0
 26 11  1  0  0  0  0
 26 21  1  0  0  0  0
 27 16  1  0  0  0  0
 27 20  1  0  0  0  0
 27 22  1  0  0  0  0
 28 20  1  0  0  0  0
 28 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 17  2  0  0  0  0
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 31 21  2  0  0  0  0
 32 22  2  0  0  0  0
 33 26  1  0  0  0  0
 34 27  1  0  0  0  0
 35 18  1  0  0  0  0
 35 19  1  0  0  0  0
 36 21  1  0  0  0  0
 36 25  1  0  0  0  0
 37 22  1  0  0  0  0
 37 28  1  0  0  0  0
M  END

HMDB0039696
     RDKit          3D
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A
 67 73  0  0  0  0  0  0  0  0999 V2000
   -1.5084    2.2550   -1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6824    1.5227   -1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883    0.5552   -2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408    0.6286   -3.2683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -0.4330   -1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024   -0.9573   -0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7082    0.2458    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4149    0.9731    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    2.1858    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1711    0.1389    0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482    0.4014    1.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835    1.6820    2.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8877   -0.4631    2.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738   -0.6062    3.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -1.0685    1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -1.2846    0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067   -2.3677    0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4873   -2.8550    2.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720   -2.4780    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -1.4460   -0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741   -0.1228   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033    0.0477    1.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    0.9415    2.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    1.6692    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    1.5720    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9127    2.6043   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872    2.5568   -1.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913    1.4216   -2.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3893   -0.7645   -2.4462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395    0.2285   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432   -0.7531    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -3.5417    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -4.7005   -0.0071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -3.0952    0.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6601   -1.7669   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1486   -1.9100   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7960   -1.4956    0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9322    0.1313    1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5545    1.9648    2.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2875   -3.4876    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4464   -2.8264    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -3.3932   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3670   -1.9364   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -1.4151   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7192    0.9913    3.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.3300    2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533    3.5209    0.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4528   -0.3055    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 37 65  1  0
 37 66  1  0
 37 67  1  0
M  END


  Mrv0541 05061311192D          

 37 43  0  0  0  0            999 V2000
    0.1296    1.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2747    0.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2762   -1.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -2.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1936   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    0.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038   -1.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 30 19  2  0  0  0  0
 31 21  2  0  0  0  0
 32 22  2  0  0  0  0
 33 26  1  0  0  0  0
 34 27  1  0  0  0  0
 35 18  1  0  0  0  0
 35 19  1  0  0  0  0
 36 21  1  0  0  0  0
 36 25  1  0  0  0  0
 37 22  1  0  0  0  0
 37 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039696

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(=O)OC2CC1(C)C1C3(O)C4C=CC5=CC=CC(=O)C5(C)C4CCC4(O)C(=O)OC2(C)C14OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O9/c1-13-19(30)35-18-12-23(13,2)20-27(34)16-9-8-14-6-5-7-17(29)24(14,3)15(16)10-11-26(33)21(31)36-25(18,4)28(20,26)37-22(27)32/h5-9,13,15-16,18,20,33-34H,10-12H2,1-4H3

> <INCHI_KEY>
NSFHPMKDYVTYOY-UHFFFAOYSA-N

> <FORMULA>
C28H30O9

> <MOLECULAR_WEIGHT>
510.5324

> <EXACT_MASS>
510.188982558

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
49.974616664400955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,19-dihydroxy-1,15,22,26-tetramethyl-4,21,24-trioxaheptacyclo[21.3.1.0²,⁶.0³,¹⁹.0³,²².0⁷,¹⁶.0¹⁰,¹⁵]heptacosa-8,10,12-triene-5,14,20,25-tetrone

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.629442255999999

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.915652125728812

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.112330319274799

> <JCHEM_PKA_STRONGEST_BASIC>
-4.193602760756854

> <JCHEM_POLAR_SURFACE_AREA>
136.43

> <JCHEM_REFRACTIVITY>
127.98549999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,19-dihydroxy-1,15,22,26-tetramethyl-4,21,24-trioxaheptacyclo[21.3.1.0²,⁶.0³,¹⁹.0³,²².0⁷,¹⁶.0¹⁰,¹⁵]heptacosa-8,10,12-triene-5,14,20,25-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039696
     RDKit          3D
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A
 67 73  0  0  0  0  0  0  0  0999 V2000
   -1.5084    2.2550   -1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6824    1.5227   -1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883    0.5552   -2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408    0.6286   -3.2683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -0.4330   -1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024   -0.9573   -0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7082    0.2458    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4149    0.9731    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    2.1858    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1711    0.1389    0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482    0.4014    1.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835    1.6820    2.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8877   -0.4631    2.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738   -0.6062    3.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -1.0685    1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -1.2846    0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067   -2.3677    0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4873   -2.8550    2.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720   -2.4780    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -1.4460   -0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741   -0.1228   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033    0.0477    1.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    0.9415    2.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    1.6692    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    1.5720    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9127    2.6043   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872    2.5568   -1.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913    1.4216   -2.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5282    0.2378   -1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893   -0.7645   -2.4462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395    0.2285   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432   -0.7531    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -3.5417    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -4.7005   -0.0071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -3.0952    0.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6601   -1.7669   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1486   -1.9100   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    2.5354   -0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194    3.1893   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812    1.6043   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4890    2.3040   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7960   -1.4956    0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5252    0.9733    0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    0.1313    1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013    3.0071    0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    1.9648    2.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    2.6236    0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829    0.3079   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    2.2474    1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -3.4876    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4464   -2.8264    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -3.3932   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3670   -1.9364   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -1.4151   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964    0.6674   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -0.9555    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192    0.9913    3.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.3300    2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533    3.5209    0.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7082    3.4386   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    1.3709   -3.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6073   -1.7204    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9412   -0.9109   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -0.3055    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373   -1.9613   -2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4234   -1.1523   -1.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6282   -2.9014   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 17 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
  8  2  1  0
 16 10  1  0
 31 21  1  0
 36  6  1  0
 22 11  1  0
 31 25  1  0
 36 16  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 12 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
 26 59  1  0
 27 60  1  0
 28 61  1  0
 32 62  1  0
 32 63  1  0
 32 64  1  0
 37 65  1  0
 37 66  1  0
 37 67  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.242   2.367   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.379   1.316   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.982  -2.381   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.358  -4.019   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.561  -0.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.583   0.755   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.020  -1.876   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.086   1.692   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.567   1.440   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.864  -2.767   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.704  -3.836   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.898  -1.201   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.181   0.829   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.064   0.503   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.004  -1.192   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.026  -0.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.501  -2.129   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.208  -2.369   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.256   0.123   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.075  -0.851   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.289  -5.118   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.400  -1.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.606  -0.016   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.523  -0.939   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.651  -3.183   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.113  -3.779   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.420  -0.032   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.140  -2.482   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.960  -3.570   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.579   0.910   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.872  -6.543   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.507  -1.242   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.840  -5.137   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.343   1.441   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.189  -1.488   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.793  -4.747   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.698  -2.545   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5    6    7                                                       
CONECT    6    5   14                                                       
CONECT    7    5   17                                                       
CONECT    8    9   14                                                       
CONECT    9    8   16                                                       
CONECT   10   11   15                                                       
CONECT   11   10   26                                                       
CONECT   12   18   23                                                       
CONECT   13    1   19   23                                                  
CONECT   14    6    8   24                                                  
CONECT   15   10   16   24                                                  
CONECT   16    9   15   27                                                  
CONECT   17    7   24   29                                                  
CONECT   18   12   25   35                                                  
CONECT   19   13   30   35                                                  
CONECT   20   23   27   28                                                  
CONECT   21   26   31   36                                                  
CONECT   22   27   32   37                                                  
CONECT   23    2   12   13   20                                             
CONECT   24    3   14   15   17                                             
CONECT   25    4   18   28   36                                             
CONECT   26   11   21   28   33                                             
CONECT   27   16   20   22   34                                             
CONECT   28   20   25   26   37                                             
CONECT   29   17                                                            
CONECT   30   19                                                            
CONECT   31   21                                                            
CONECT   32   22                                                            
CONECT   33   26                                                            
CONECT   34   27                                                            
CONECT   35   18   19                                                       
CONECT   36   21   25                                                       
CONECT   37   22   28                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

COMPND    HMDB0039696
HETATM    1  C1  UNL     1      -1.508   2.255  -1.671  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.682   1.523  -1.110  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.288   0.555  -2.026  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.041   0.629  -3.268  1.00  0.00           O  
HETATM    5  O2  UNL     1      -4.125  -0.433  -1.554  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.902  -0.957  -0.256  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.708   0.246   0.620  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.415   0.973   0.292  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.458   2.186   1.186  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.171   0.139   0.349  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.248   0.401   1.467  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.283   1.682   2.006  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.888  -0.463   2.533  1.00  0.00           C  
HETATM   14  O4  UNL     1      -0.474  -0.606   3.713  1.00  0.00           O  
HETATM   15  O5  UNL     1      -2.022  -1.069   1.957  1.00  0.00           O  
HETATM   16  C11 UNL     1      -1.554  -1.285   0.604  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.607  -2.368   0.707  1.00  0.00           C  
HETATM   18  O6  UNL     1      -0.487  -2.855   2.066  1.00  0.00           O  
HETATM   19  C13 UNL     1       0.672  -2.478   0.085  1.00  0.00           C  
HETATM   20  C14 UNL     1       1.359  -1.446  -0.717  1.00  0.00           C  
HETATM   21  C15 UNL     1       1.674  -0.123  -0.094  1.00  0.00           C  
HETATM   22  C16 UNL     1       1.203   0.048   1.275  1.00  0.00           C  
HETATM   23  C17 UNL     1       2.018   0.941   2.118  1.00  0.00           C  
HETATM   24  C18 UNL     1       3.035   1.669   1.758  1.00  0.00           C  
HETATM   25  C19 UNL     1       3.401   1.572   0.330  1.00  0.00           C  
HETATM   26  C20 UNL     1       3.913   2.604  -0.294  1.00  0.00           C  
HETATM   27  C21 UNL     1       4.287   2.557  -1.700  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.091   1.422  -2.338  1.00  0.00           C  
HETATM   29  C23 UNL     1       3.528   0.238  -1.711  1.00  0.00           C  
HETATM   30  O7  UNL     1       3.389  -0.764  -2.446  1.00  0.00           O  
HETATM   31  C24 UNL     1       3.139   0.229  -0.263  1.00  0.00           C  
HETATM   32  C25 UNL     1       4.043  -0.753   0.447  1.00  0.00           C  
HETATM   33  C26 UNL     1      -1.491  -3.542   0.252  1.00  0.00           C  
HETATM   34  O8  UNL     1      -1.039  -4.701  -0.007  1.00  0.00           O  
HETATM   35  O9  UNL     1      -2.802  -3.095   0.191  1.00  0.00           O  
HETATM   36  C27 UNL     1      -2.660  -1.767  -0.285  1.00  0.00           C  
HETATM   37  C28 UNL     1      -2.149  -1.910  -1.703  1.00  0.00           C  
HETATM   38  H1  UNL     1      -0.746   2.535  -0.935  1.00  0.00           H  
HETATM   39  H2  UNL     1      -1.819   3.189  -2.184  1.00  0.00           H  
HETATM   40  H3  UNL     1      -1.081   1.604  -2.490  1.00  0.00           H  
HETATM   41  H4  UNL     1      -3.489   2.304  -0.955  1.00  0.00           H  
HETATM   42  H5  UNL     1      -4.796  -1.496   0.111  1.00  0.00           H  
HETATM   43  H6  UNL     1      -4.525   0.973   0.295  1.00  0.00           H  
HETATM   44  H7  UNL     1      -3.932   0.131   1.675  1.00  0.00           H  
HETATM   45  H8  UNL     1      -1.801   3.007   0.902  1.00  0.00           H  
HETATM   46  H9  UNL     1      -2.554   1.965   2.262  1.00  0.00           H  
HETATM   47  H10 UNL     1      -3.490   2.624   0.958  1.00  0.00           H  
HETATM   48  H11 UNL     1      -0.683   0.308  -0.603  1.00  0.00           H  
HETATM   49  H12 UNL     1       0.454   2.247   1.728  1.00  0.00           H  
HETATM   50  H13 UNL     1       0.287  -3.488   2.098  1.00  0.00           H  
HETATM   51  H14 UNL     1       1.446  -2.826   0.852  1.00  0.00           H  
HETATM   52  H15 UNL     1       0.700  -3.393  -0.601  1.00  0.00           H  
HETATM   53  H16 UNL     1       2.367  -1.936  -0.920  1.00  0.00           H  
HETATM   54  H17 UNL     1       0.935  -1.415  -1.735  1.00  0.00           H  
HETATM   55  H18 UNL     1       1.196   0.667  -0.759  1.00  0.00           H  
HETATM   56  H19 UNL     1       1.400  -0.955   1.792  1.00  0.00           H  
HETATM   57  H20 UNL     1       1.719   0.991   3.185  1.00  0.00           H  
HETATM   58  H21 UNL     1       3.620   2.330   2.388  1.00  0.00           H  
HETATM   59  H22 UNL     1       4.053   3.521   0.296  1.00  0.00           H  
HETATM   60  H23 UNL     1       4.708   3.439  -2.172  1.00  0.00           H  
HETATM   61  H24 UNL     1       4.365   1.371  -3.385  1.00  0.00           H  
HETATM   62  H25 UNL     1       3.607  -1.720   0.668  1.00  0.00           H  
HETATM   63  H26 UNL     1       4.941  -0.911  -0.184  1.00  0.00           H  
HETATM   64  H27 UNL     1       4.453  -0.305   1.401  1.00  0.00           H  
HETATM   65  H28 UNL     1      -3.037  -1.961  -2.365  1.00  0.00           H  
HETATM   66  H29 UNL     1      -1.423  -1.152  -1.980  1.00  0.00           H  
HETATM   67  H30 UNL     1      -1.628  -2.901  -1.858  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3    8   41
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   36   42
CONECT    7    8   43   44
CONECT    8    9   10
CONECT    9   45   46   47
CONECT   10   11   16   48
CONECT   11   12   13   22
CONECT   12   49
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   17   36
CONECT   17   18   19   33
CONECT   18   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   31   55
CONECT   22   23   56
CONECT   23   24   24   57
CONECT   24   25   58
CONECT   25   26   26   31
CONECT   26   27   59
CONECT   27   28   28   60
CONECT   28   29   61
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   62   63   64
CONECT   33   34   34   35
CONECT   35   36
CONECT   36   37
CONECT   37   65   66   67
END

HMDB0039696
     RDKit          3D
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A
 67 73  0  0  0  0  0  0  0  0999 V2000
   -1.5084    2.2550   -1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6824    1.5227   -1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883    0.5552   -2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408    0.6286   -3.2683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -0.4330   -1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024   -0.9573   -0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7082    0.2458    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4149    0.9731    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    2.1858    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1711    0.1389    0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482    0.4014    1.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835    1.6820    2.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8877   -0.4631    2.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738   -0.6062    3.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -1.0685    1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -1.2846    0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067   -2.3677    0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4873   -2.8550    2.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720   -2.4780    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -1.4460   -0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741   -0.1228   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033    0.0477    1.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    0.9415    2.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    1.6692    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    1.5720    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9127    2.6043   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872    2.5568   -1.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913    1.4216   -2.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5282    0.2378   -1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893   -0.7645   -2.4462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395    0.2285   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432   -0.7531    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -3.5417    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -4.7005   -0.0071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -3.0952    0.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6601   -1.7669   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1486   -1.9100   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    2.5354   -0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194    3.1893   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812    1.6043   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4890    2.3040   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7960   -1.4956    0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5252    0.9733    0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    0.1313    1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013    3.0071    0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    1.9648    2.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    2.6236    0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829    0.3079   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    2.2474    1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -3.4876    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4464   -2.8264    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -3.3932   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3670   -1.9364   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -1.4151   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964    0.6674   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -0.9555    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192    0.9913    3.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.3300    2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533    3.5209    0.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7082    3.4386   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    1.3709   -3.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6073   -1.7204    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9412   -0.9109   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -0.3055    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373   -1.9613   -2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4234   -1.1523   -1.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6282   -2.9014   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 17 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
  8  2  1  0
 16 10  1  0
 31 21  1  0
 36  6  1  0
 22 11  1  0
 31 25  1  0
 36 16  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 12 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
 26 59  1  0
 27 60  1  0
 28 61  1  0
 32 62  1  0
 32 63  1  0
 32 64  1  0
 37 65  1  0
 37 66  1  0
 37 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Etrenol	HMDB
Hicantona	HMDB
Hycanthon	HMDB
Hycanthone	HMDB
Hycanthone mesylate	HMDB
Hycanthonum	HMDB
Lucanthone metabolite	HMDB

Chemical Formula

C₂₈H₃₀O₉

Average Molecular Weight

510.5324

Monoisotopic Molecular Weight

510.188982558

IUPAC Name

6,19-dihydroxy-1,15,22,26-tetramethyl-4,21,24-trioxaheptacyclo[21.3.1.0²,⁶.0³,¹⁹.0³,²².0⁷,¹⁶.0¹⁰,¹⁵]heptacosa-8,10,12-triene-5,14,20,25-tetrone

Traditional Name

6,19-dihydroxy-1,15,22,26-tetramethyl-4,21,24-trioxaheptacyclo[21.3.1.0²,⁶.0³,¹⁹.0³,²².0⁷,¹⁶.0¹⁰,¹⁵]heptacosa-8,10,12-triene-5,14,20,25-tetrone

CAS Registry Number

134434-71-2

SMILES

CC1C(=O)OC2CC1(C)C1C3(O)C4C=CC5=CC=CC(=O)C5(C)C4CCC4(O)C(=O)OC2(C)C14OC3=O

InChI Identifier

InChI=1S/C28H30O9/c1-13-19(30)35-18-12-23(13,2)20-27(34)16-9-8-14-6-5-7-17(29)24(14,3)15(16)10-11-26(33)21(31)36-25(18,4)28(20,26)37-22(27)32/h5-9,13,15-16,18,20,33-34H,10-12H2,1-4H3

InChI Key

NSFHPMKDYVTYOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Physalins and derivatives

Direct Parent

Physalins and derivatives

Alternative Parents

Substituents

Physalin skeleton
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxane
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0039696)

Biofluid or Excreta

Urine (HMDB: HMDB0039696)

Tissue substructure

Hepatic tissue (HMDB: HMDB0039696)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039696)

Source

Endogenous

Endogenous (HMDB: HMDB0039696)

Plant

Plant (HMDB: HMDB0039696)

Animal

Animal (HMDB: HMDB0039696)

Exogenous

Food

Food (HMDB: HMDB0039696)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039696)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039696)

Cellular process

Cell signaling (HMDB: HMDB0039696)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039696)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039696)

Nutrient

Nutrient (HMDB: HMDB0039696)

Molecular messenger

Signaling molecule (HMDB: HMDB0039696)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039696)

Emulsifier (HMDB: HMDB0039696)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	273 - 275 °C	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
Water Solubility	0.24 g/L	ALOGPS
logP	1.95	ALOGPS
logP	1.63	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.43 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	127.99 m³·mol⁻¹	ChemAxon
Polarizability	49.97 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
DarkChem	[M+H]+	216.006	31661259
DarkChem	[M-H]-	205.532	31661259
DeepCCS	[M-2H]-	249.867	30932474
DeepCCS	[M+Na]+	225.291	30932474
AllCCS	[M+H]+	214.1	32859911
AllCCS	[M+H-H2O]+	212.3	32859911
AllCCS	[M+NH4]+	215.7	32859911
AllCCS	[M+Na]+	216.1	32859911
AllCCS	[M-H]-	217.4	32859911
AllCCS	[M+Na-2H]-	218.4	32859911
AllCCS	[M+HCOO]-	219.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A	CC1C(=O)OC2CC1(C)C1C3(O)C4C=CC5=CC=CC(=O)C5(C)C4CCC4(O)C(=O)OC2(C)C14OC3=O	4793.3	Standard polar	33892256
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A	CC1C(=O)OC2CC1(C)C1C3(O)C4C=CC5=CC=CC(=O)C5(C)C4CCC4(O)C(=O)OC2(C)C14OC3=O	3416.4	Standard non polar	33892256
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A	CC1C(=O)OC2CC1(C)C1C3(O)C4C=CC5=CC=CC(=O)C5(C)C4CCC4(O)C(=O)OC2(C)C14OC3=O	4383.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A,1TMS,isomer #1	CC1C(=O)OC2CC1(C)C1C3(O[Si](C)(C)C)C(=O)OC14C(O)(CCC1C3C=CC3=CC=CC(=O)C31C)C(=O)OC24C	4119.2	Semi standard non polar	33892256
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A,1TMS,isomer #2	CC1C(=O)OC2CC1(C)C1C3(O)C(=O)OC14C(O[Si](C)(C)C)(CCC1C3C=CC3=CC=CC(=O)C31C)C(=O)OC24C	4157.2	Semi standard non polar	33892256
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A,2TMS,isomer #1	CC1C(=O)OC2CC1(C)C1C3(O[Si](C)(C)C)C(=O)OC14C(O[Si](C)(C)C)(CCC1C3C=CC3=CC=CC(=O)C31C)C(=O)OC24C	4112.2	Semi standard non polar	33892256
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A,1TBDMS,isomer #1	CC1C(=O)OC2CC1(C)C1C3(O[Si](C)(C)C(C)(C)C)C(=O)OC14C(O)(CCC1C3C=CC3=CC=CC(=O)C31C)C(=O)OC24C	4382.3	Semi standard non polar	33892256
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A,1TBDMS,isomer #2	CC1C(=O)OC2CC1(C)C1C3(O)C(=O)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C=CC3=CC=CC(=O)C31C)C(=O)OC24C	4412.4	Semi standard non polar	33892256
25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A,2TBDMS,isomer #1	CC1C(=O)OC2CC1(C)C1C3(O[Si](C)(C)C(C)(C)C)C(=O)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C=CC3=CC=CC(=O)C31C)C(=O)OC24C	4627.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-01bi-1910800000-ad6602e2aafaa628f9df	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A GC-MS (2 TMS) - 70eV, Positive	splash10-01p9-2700009000-7e9b28b8aa1c1bec62d9	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 10V, Positive-QTOF	splash10-03di-0000970000-d4377fc68bdf2d9944cb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 20V, Positive-QTOF	splash10-01ox-0000910000-ce7510f47f063a0e3818	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 40V, Positive-QTOF	splash10-000j-1002900000-7f210a102c0b8ec77817	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 10V, Negative-QTOF	splash10-0a4i-0000790000-c7ce07f9a2bb619e7ba1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 20V, Negative-QTOF	splash10-0aou-0000940000-778a8b3d6268d2693153	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 40V, Negative-QTOF	splash10-000i-1801900000-2fafaa2f69b54ce1a34d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 10V, Negative-QTOF	splash10-0a4i-0000190000-d2b23ee53da864be7d38	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 20V, Negative-QTOF	splash10-0a4i-0000390000-c9e9063d703c15dc7a62	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 40V, Negative-QTOF	splash10-0a4i-0200980000-6396cae14c9dfb368b2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 10V, Positive-QTOF	splash10-03di-0000090000-1aa2dce78661b19c596b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 20V, Positive-QTOF	splash10-01q9-0200930000-4fdf8c53d9f12b1ab6b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A 40V, Positive-QTOF	splash10-0a4i-1901200000-6d34565309509c23ee2b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB019325

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73825229

PDB ID

Not Available

ChEBI ID

Not Available

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A (HMDB0039696)

MOL for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

3D MOL for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

3D SDF for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

3D-SDF for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

PDB for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

3D PDB for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

SMILES for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

INCHI for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

Structure for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

3D Structure for HMDB0039696 (25,27-Dihydro-4,7-didehydro-7-deoxyphysalin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra