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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:13:36 UTC

Update Date

2022-03-07 02:56:18 UTC

HMDB ID

HMDB0039697

Secondary Accession Numbers

HMDB39697

Metabolite Identification

Common Name

Isophysalin B

Description

Isophysalin B 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). Isophysalin B 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 05061311202D          

 37 44  0  0  0  0            999 V2000
    1.1597    0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0537   -0.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226   -1.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    0.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5138    0.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6910   -0.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1973    1.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786    1.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4540   -1.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8055   -1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788   -0.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6952    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5558   -0.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0579    0.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    0.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8724   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2584   -1.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1656   -0.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1332   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6115    0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931   -2.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190    0.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6120   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743   -1.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2016    0.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4295   -0.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5517   -1.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -0.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    1.1431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881   -3.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3814   -2.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    1.3288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -0.3127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751   -2.2035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844    0.1805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  2  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 17  6  1  0  0  0  0
 18 11  1  0  0  0  0
 20 19  1  0  0  0  0
 21 16  1  0  0  0  0
 23  1  1  0  0  0  0
 23 11  1  0  0  0  0
 23 16  1  0  0  0  0
 23 19  1  0  0  0  0
 24  2  1  0  0  0  0
 24 13  1  0  0  0  0
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 24 17  1  0  0  0  0
 25  3  1  0  0  0  0
 25 18  1  0  0  0  0
 26 10  1  0  0  0  0
 26 22  1  0  0  0  0
 27 15  1  0  0  0  0
 27 20  1  0  0  0  0
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 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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 33 26  1  0  0  0  0
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 35 18  1  0  0  0  0
 35 21  1  0  0  0  0
 36 22  1  0  0  0  0
 36 25  1  0  0  0  0
 37 27  1  0  0  0  0
 37 28  1  0  0  0  0
M  END

HMDB0039697
     RDKit          3D
Isophysalin B
 67 74  0  0  0  0  0  0  0  0999 V2000
    3.7334   -0.7942    1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537    0.1076    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0130    1.3752    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4679    2.4322    0.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4839    1.3177    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9390    0.2187   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797   -0.6393   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.5142   -1.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8298   -0.9507   -2.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3911   -0.8401   -1.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1174   -0.8905   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366    0.3407    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4555    0.5977    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318    1.2863    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7212    1.7612    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2183    2.6117    0.0818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    2.5743    1.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994    3.0518    2.9330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326    2.6738    0.8678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    1.6201   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    2.2383   -1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0300    0.9402   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3624   -0.1113    0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -1.1028    0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613   -2.2048    1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -1.7171   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -2.5877   -0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -1.9349   -1.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646   -0.9973   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.2131   -0.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995    0.7484    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180   -0.3965    1.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8585   -1.3281    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829   -2.1321    1.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3091   -0.7877   -1.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7388   -1.0644   -2.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    0.3450   -1.5401 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7018   -1.2717    0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -0.1858    2.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0570   -1.6134    1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9497    1.2239    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9073    2.2628   -0.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9887    0.1314   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4995   -1.4103   -2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.3915   -2.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974   -1.6198   -2.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328    0.1506   -2.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493   -1.7927   -0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382    1.1783   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3384    1.1934    2.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5998   -0.3887    2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489    2.1701    2.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    0.6062    2.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766    3.2601    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531    2.1445   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    3.3000   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    1.7125   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506    1.7012   -0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4059    0.3213    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295   -0.5660    0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
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  6  7  2  0
  7  8  1  0
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 31 15  1  0
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 32 24  1  0
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 27 66  1  0
 32 67  1  0
M  END


  Mrv0541 05061311202D          

 37 44  0  0  0  0            999 V2000
    1.1597    0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0537   -0.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226   -1.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    0.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5138    0.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6910   -0.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1973    1.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786    1.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4540   -1.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8055   -1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788   -0.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6952    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10  9  1  0  0  0  0
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 23  1  1  0  0  0  0
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 34 27  1  0  0  0  0
 35 18  1  0  0  0  0
 35 21  1  0  0  0  0
 36 22  1  0  0  0  0
 36 25  1  0  0  0  0
 37 27  1  0  0  0  0
 37 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039697

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12OC(=O)C3(O)CCC4C(CC=C5C=CCC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O9/c1-23-11-18-25(3)28-19(23)20(30)27(37-28,34-12-16(23)21(31)35-18)15-8-7-13-5-4-6-17(29)24(13,2)14(15)9-10-26(28,33)22(32)36-25/h4-5,7,14-16,18-19,33H,6,8-12H2,1-3H3

> <INCHI_KEY>
HRUAQJXBUYEBPK-UHFFFAOYSA-N

> <FORMULA>
C28H30O9

> <MOLECULAR_WEIGHT>
510.5324

> <EXACT_MASS>
510.188982558

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
50.18121804746122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacosa-12,14-diene-4,10,22,29-tetrone

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
2.225175346333333

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.530010200125021

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.673877896705893

> <JCHEM_PKA_STRONGEST_BASIC>
-4.12674155725487

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000002

> <JCHEM_REFRACTIVITY>
125.72489999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacosa-12,14-diene-4,10,22,29-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039697
     RDKit          3D
Isophysalin B
 67 74  0  0  0  0  0  0  0  0999 V2000
    3.7334   -0.7942    1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537    0.1076    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0130    1.3752    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4679    2.4322    0.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4839    1.3177    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9390    0.2187   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797   -0.6393   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.5142   -1.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8298   -0.9507   -2.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3911   -0.8401   -1.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1174   -0.8905   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366    0.3407    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4555    0.5977    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318    1.2863    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7212    1.7612    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2183    2.6117    0.0818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    2.5743    1.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994    3.0518    2.9330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326    2.6738    0.8678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    1.6201   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    2.2383   -1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0300    0.9402   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3624   -0.1113    0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -1.1028    0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613   -2.2048    1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -1.7171   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -2.5877   -0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -1.9349   -1.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646   -0.9973   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.2131   -0.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995    0.7484    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180   -0.3965    1.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8585   -1.3281    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829   -2.1321    1.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3091   -0.7877   -1.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7388   -1.0644   -2.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    0.3450   -1.5401 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7018   -1.2717    0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -0.1858    2.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0570   -1.6134    1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9497    1.2239    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9073    2.2628   -0.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9887    0.1314   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4995   -1.4103   -2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.3915   -2.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974   -1.6198   -2.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328    0.1506   -2.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493   -1.7927   -0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382    1.1783   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3384    1.1934    2.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5998   -0.3887    2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489    2.1701    2.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    0.6062    2.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766    3.2601    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531    2.1445   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    3.3000   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    1.7125   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506    1.7012   -0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4059    0.3213    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295   -0.5660    0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0376   -2.0254    2.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6455   -2.2108    1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563   -3.1927    1.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0418   -2.4119   -0.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7927   -3.3160   -0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2262   -3.2434   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -0.1766    2.3016 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 26 35  1  0
 35 36  2  0
 35 37  1  0
  8  2  1  0
 29 11  1  0
 12  2  1  0
 31 15  1  0
 31 20  1  0
 37 22  1  0
 32 24  1  0
 33 29  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 16 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 25 61  1  0
 25 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 32 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       2.165   1.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.567  -1.726   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.042  -3.582   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.222   0.074   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.292   1.302   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.623  -1.344   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.835   2.339   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.307   2.148   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.447  -2.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.237  -2.974   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.147  -0.918   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.714   2.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.764   1.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.637  -0.498   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.708   0.729   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.463   1.538   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.095  -1.535   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.482  -1.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.176  -0.567   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.982  -0.413   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.141   1.053   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.974  -4.279   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.969   0.211   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.166  -0.307   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.142  -2.598   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.685  -2.858   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.110   1.014   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.668  -1.676   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.497  -2.954   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.069  -1.504   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.239   2.134   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.711  -5.631   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.445  -4.197   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.330   2.480   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.610  -0.584   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.447  -4.113   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.771   0.337   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4    5    6                                                       
CONECT    5    4   13                                                       
CONECT    6    4   17                                                       
CONECT    7    8   13                                                       
CONECT    8    7   15                                                       
CONECT    9   10   14                                                       
CONECT   10    9   26                                                       
CONECT   11   18   23                                                       
CONECT   12   16   34                                                       
CONECT   13    5    7   24                                                  
CONECT   14    9   15   24                                                  
CONECT   15    8   14   27                                                  
CONECT   16   12   21   23                                                  
CONECT   17    6   24   29                                                  
CONECT   18   11   25   35                                                  
CONECT   19   20   23   28                                                  
CONECT   20   19   27   30                                                  
CONECT   21   16   31   35                                                  
CONECT   22   26   32   36                                                  
CONECT   23    1   11   16   19                                             
CONECT   24    2   13   14   17                                             
CONECT   25    3   18   28   36                                             
CONECT   26   10   22   28   33                                             
CONECT   27   15   20   34   37                                             
CONECT   28   19   25   26   37                                             
CONECT   29   17                                                            
CONECT   30   20                                                            
CONECT   31   21                                                            
CONECT   32   22                                                            
CONECT   33   26                                                            
CONECT   34   12   27                                                       
CONECT   35   18   21                                                       
CONECT   36   22   25                                                       
CONECT   37   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   88    0
END

COMPND    HMDB0039697
HETATM    1  C1  UNL     1       3.733  -0.794   1.216  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.254   0.108   0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.013   1.375   0.210  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.468   2.432   0.418  1.00  0.00           O  
HETATM    5  C4  UNL     1       5.484   1.318   0.058  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.939   0.219  -0.832  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.080  -0.639  -1.408  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.645  -0.514  -1.171  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.830  -0.951  -2.087  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.391  -0.840  -1.892  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.117  -0.891  -0.379  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.737   0.341   0.206  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.455   0.598   1.644  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.232   1.286   2.043  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.721   1.761   1.045  1.00  0.00           C  
HETATM   16  O2  UNL     1      -0.218   2.612   0.082  1.00  0.00           O  
HETATM   17  C15 UNL     1      -1.769   2.574   1.775  1.00  0.00           C  
HETATM   18  O3  UNL     1      -1.699   3.052   2.933  1.00  0.00           O  
HETATM   19  O4  UNL     1      -2.833   2.674   0.868  1.00  0.00           O  
HETATM   20  C16 UNL     1      -2.744   1.620  -0.074  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.326   2.238  -1.412  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.030   0.940  -0.259  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.362  -0.111   0.761  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.228  -1.103   0.750  1.00  0.00           C  
HETATM   25  C21 UNL     1      -3.561  -2.205   1.762  1.00  0.00           C  
HETATM   26  C22 UNL     1      -3.146  -1.717  -0.599  1.00  0.00           C  
HETATM   27  C23 UNL     1      -1.957  -2.588  -0.840  1.00  0.00           C  
HETATM   28  O5  UNL     1      -0.804  -1.935  -1.209  1.00  0.00           O  
HETATM   29  C24 UNL     1      -0.365  -0.997  -0.282  1.00  0.00           C  
HETATM   30  O6  UNL     1      -0.913   0.213  -0.673  1.00  0.00           O  
HETATM   31  C25 UNL     1      -1.599   0.748   0.381  1.00  0.00           C  
HETATM   32  C26 UNL     1      -2.018  -0.396   1.246  1.00  0.00           C  
HETATM   33  C27 UNL     1      -0.858  -1.328   1.047  1.00  0.00           C  
HETATM   34  O7  UNL     1      -0.483  -2.132   1.840  1.00  0.00           O  
HETATM   35  C28 UNL     1      -3.309  -0.788  -1.730  1.00  0.00           C  
HETATM   36  O8  UNL     1      -2.739  -1.064  -2.820  1.00  0.00           O  
HETATM   37  O9  UNL     1      -4.083   0.345  -1.540  1.00  0.00           O  
HETATM   38  H1  UNL     1       4.702  -1.272   0.892  1.00  0.00           H  
HETATM   39  H2  UNL     1       3.986  -0.186   2.106  1.00  0.00           H  
HETATM   40  H3  UNL     1       3.057  -1.613   1.450  1.00  0.00           H  
HETATM   41  H4  UNL     1       5.950   1.224   1.082  1.00  0.00           H  
HETATM   42  H5  UNL     1       5.907   2.263  -0.354  1.00  0.00           H  
HETATM   43  H6  UNL     1       6.989   0.131  -1.002  1.00  0.00           H  
HETATM   44  H7  UNL     1       5.500  -1.410  -2.044  1.00  0.00           H  
HETATM   45  H8  UNL     1       3.207  -1.392  -2.985  1.00  0.00           H  
HETATM   46  H9  UNL     1       0.797  -1.620  -2.404  1.00  0.00           H  
HETATM   47  H10 UNL     1       1.033   0.151  -2.249  1.00  0.00           H  
HETATM   48  H11 UNL     1       1.649  -1.793  -0.014  1.00  0.00           H  
HETATM   49  H12 UNL     1       1.538   1.178  -0.468  1.00  0.00           H  
HETATM   50  H13 UNL     1       2.338   1.193   2.041  1.00  0.00           H  
HETATM   51  H14 UNL     1       1.600  -0.389   2.181  1.00  0.00           H  
HETATM   52  H15 UNL     1       0.449   2.170   2.726  1.00  0.00           H  
HETATM   53  H16 UNL     1      -0.332   0.606   2.754  1.00  0.00           H  
HETATM   54  H17 UNL     1       0.377   3.260   0.513  1.00  0.00           H  
HETATM   55  H18 UNL     1      -3.153   2.145  -2.166  1.00  0.00           H  
HETATM   56  H19 UNL     1      -2.018   3.300  -1.280  1.00  0.00           H  
HETATM   57  H20 UNL     1      -1.458   1.712  -1.851  1.00  0.00           H  
HETATM   58  H21 UNL     1      -4.851   1.701  -0.209  1.00  0.00           H  
HETATM   59  H22 UNL     1      -4.406   0.321   1.791  1.00  0.00           H  
HETATM   60  H23 UNL     1      -5.330  -0.566   0.487  1.00  0.00           H  
HETATM   61  H24 UNL     1      -3.038  -2.025   2.733  1.00  0.00           H  
HETATM   62  H25 UNL     1      -4.645  -2.211   1.994  1.00  0.00           H  
HETATM   63  H26 UNL     1      -3.256  -3.193   1.409  1.00  0.00           H  
HETATM   64  H27 UNL     1      -4.042  -2.412  -0.670  1.00  0.00           H  
HETATM   65  H28 UNL     1      -1.793  -3.316  -0.007  1.00  0.00           H  
HETATM   66  H29 UNL     1      -2.226  -3.243  -1.714  1.00  0.00           H  
HETATM   67  H30 UNL     1      -2.145  -0.177   2.302  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3    8   12
CONECT    3    4    4    5
CONECT    5    6   41   42
CONECT    6    7    7   43
CONECT    7    8   44
CONECT    8    9    9
CONECT    9   10   45
CONECT   10   11   46   47
CONECT   11   12   29   48
CONECT   12   13   49
CONECT   13   14   50   51
CONECT   14   15   52   53
CONECT   15   16   17   31
CONECT   16   54
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   22   31
CONECT   21   55   56   57
CONECT   22   23   37   58
CONECT   23   24   59   60
CONECT   24   25   26   32
CONECT   25   61   62   63
CONECT   26   27   35   64
CONECT   27   28   65   66
CONECT   28   29
CONECT   29   30   33
CONECT   30   31
CONECT   31   32
CONECT   32   33   67
CONECT   33   34   34
CONECT   35   36   36   37
END

HMDB0039697
     RDKit          3D
Isophysalin B
 67 74  0  0  0  0  0  0  0  0999 V2000
    3.7334   -0.7942    1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537    0.1076    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0130    1.3752    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4679    2.4322    0.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4839    1.3177    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9390    0.2187   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797   -0.6393   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.5142   -1.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8298   -0.9507   -2.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3911   -0.8401   -1.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1174   -0.8905   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366    0.3407    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4555    0.5977    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318    1.2863    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7212    1.7612    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2183    2.6117    0.0818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    2.5743    1.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994    3.0518    2.9330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326    2.6738    0.8678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    1.6201   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    2.2383   -1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0300    0.9402   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3624   -0.1113    0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -1.1028    0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613   -2.2048    1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -1.7171   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -2.5877   -0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -1.9349   -1.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646   -0.9973   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.2131   -0.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995    0.7484    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180   -0.3965    1.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8585   -1.3281    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829   -2.1321    1.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3091   -0.7877   -1.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7388   -1.0644   -2.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    0.3450   -1.5401 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7018   -1.2717    0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -0.1858    2.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0570   -1.6134    1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9497    1.2239    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9073    2.2628   -0.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9887    0.1314   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4995   -1.4103   -2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.3915   -2.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974   -1.6198   -2.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328    0.1506   -2.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493   -1.7927   -0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382    1.1783   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3384    1.1934    2.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5998   -0.3887    2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4489    2.1701    2.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    0.6062    2.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766    3.2601    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531    2.1445   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    3.3000   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    1.7125   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506    1.7012   -0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4059    0.3213    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295   -0.5660    0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0376   -2.0254    2.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6455   -2.2108    1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563   -3.1927    1.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0418   -2.4119   -0.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7927   -3.3160   -0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2262   -3.2434   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -0.1766    2.3016 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 26 35  1  0
 35 36  2  0
 35 37  1  0
  8  2  1  0
 29 11  1  0
 12  2  1  0
 31 15  1  0
 31 20  1  0
 37 22  1  0
 32 24  1  0
 33 29  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 16 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 25 61  1  0
 25 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 32 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₉

Average Molecular Weight

510.5324

Monoisotopic Molecular Weight

510.188982558

IUPAC Name

5-hydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacosa-12,14-diene-4,10,22,29-tetrone

Traditional Name

5-hydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacosa-12,14-diene-4,10,22,29-tetrone

CAS Registry Number

26435-77-8

SMILES

CC12OC(=O)C3(O)CCC4C(CC=C5C=CCC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5

InChI Identifier

InChI=1S/C28H30O9/c1-23-11-18-25(3)28-19(23)20(30)27(37-28,34-12-16(23)21(31)35-18)15-8-7-13-5-4-6-17(29)24(13,2)14(15)9-10-26(28,33)22(32)36-25/h4-5,7,14-16,18-19,33H,6,8-12H2,1-3H3

InChI Key

HRUAQJXBUYEBPK-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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0039697)

Biofluid or Excreta

Urine (HMDB: HMDB0039697)

Tissue substructure

Hepatic tissue (HMDB: HMDB0039697)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039697)

Source

Endogenous

Endogenous (HMDB: HMDB0039697)

Plant

Plant (HMDB: HMDB0039697)

Animal

Animal (HMDB: HMDB0039697)

Exogenous

Food

Food (HMDB: HMDB0039697)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039697)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039697)

Cellular process

Cell signaling (HMDB: HMDB0039697)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039697)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039697)

Nutrient

Nutrient (HMDB: HMDB0039697)

Molecular messenger

Signaling molecule (HMDB: HMDB0039697)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039697)

Emulsifier (HMDB: HMDB0039697)

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
Water Solubility	0.53 g/L	ALOGPS
logP	2.13	ALOGPS
logP	2.23	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	125.72 m³·mol⁻¹	ChemAxon
Polarizability	50.18 Å³	ChemAxon
Number of Rings	8	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]+	213.482	31661259
DarkChem	[M-H]-	208.009	31661259
DeepCCS	[M-2H]-	245.47	30932474
DeepCCS	[M+Na]+	220.898	30932474
AllCCS	[M+H]+	214.0	32859911
AllCCS	[M+H-H2O]+	212.2	32859911
AllCCS	[M+NH4]+	215.5	32859911
AllCCS	[M+Na]+	216.0	32859911
AllCCS	[M-H]-	218.0	32859911
AllCCS	[M+Na-2H]-	219.0	32859911
AllCCS	[M+HCOO]-	220.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isophysalin B	CC12OC(=O)C3(O)CCC4C(CC=C5C=CCC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5	4709.7	Standard polar	33892256
Isophysalin B	CC12OC(=O)C3(O)CCC4C(CC=C5C=CCC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5	3577.9	Standard non polar	33892256
Isophysalin B	CC12OC(=O)C3(O)CCC4C(CC=C5C=CCC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5	4380.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isophysalin B,1TMS,isomer #1	CC12C(=O)CC=CC1=CCC1C2CCC2(O[Si](C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O4	4226.8	Semi standard non polar	33892256
Isophysalin B,1TMS,isomer #2	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O)(CCC1C4CC=C2C=CCC(=O)C21C)C(=O)OC35C	4054.4	Semi standard non polar	33892256
Isophysalin B,1TMS,isomer #3	CC12C(=CCC3C1CCC1(O)C(=O)OC4(C)C5CC6(C)C(COC37OC14C6C7=O)C(=O)O5)C=CC=C2O[Si](C)(C)C	4143.8	Semi standard non polar	33892256
Isophysalin B,2TMS,isomer #1	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O[Si](C)(C)C)(CCC1C4CC=C2C=CCC(=O)C21C)C(=O)OC35C	4048.7	Semi standard non polar	33892256
Isophysalin B,2TMS,isomer #1	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O[Si](C)(C)C)(CCC1C4CC=C2C=CCC(=O)C21C)C(=O)OC35C	3867.0	Standard non polar	33892256
Isophysalin B,2TMS,isomer #2	CC12C(=CCC3C1CCC1(O[Si](C)(C)C)C(=O)OC4(C)C5CC6(C)C(COC37OC14C6C7=O)C(=O)O5)C=CC=C2O[Si](C)(C)C	4127.4	Semi standard non polar	33892256
Isophysalin B,2TMS,isomer #2	CC12C(=CCC3C1CCC1(O[Si](C)(C)C)C(=O)OC4(C)C5CC6(C)C(COC37OC14C6C7=O)C(=O)O5)C=CC=C2O[Si](C)(C)C	3824.8	Standard non polar	33892256
Isophysalin B,2TMS,isomer #3	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O)(CCC1C4CC=C2C=CC=C(O[Si](C)(C)C)C21C)C(=O)OC35C	3949.7	Semi standard non polar	33892256
Isophysalin B,2TMS,isomer #3	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O)(CCC1C4CC=C2C=CC=C(O[Si](C)(C)C)C21C)C(=O)OC35C	3683.8	Standard non polar	33892256
Isophysalin B,3TMS,isomer #1	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O[Si](C)(C)C)(CCC1C4CC=C2C=CC=C(O[Si](C)(C)C)C21C)C(=O)OC35C	3910.6	Semi standard non polar	33892256
Isophysalin B,3TMS,isomer #1	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O[Si](C)(C)C)(CCC1C4CC=C2C=CC=C(O[Si](C)(C)C)C21C)C(=O)OC35C	3704.4	Standard non polar	33892256
Isophysalin B,1TBDMS,isomer #1	CC12C(=O)CC=CC1=CCC1C2CCC2(O[Si](C)(C)C(C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O4	4476.5	Semi standard non polar	33892256
Isophysalin B,1TBDMS,isomer #2	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O)(CCC1C4CC=C2C=CCC(=O)C21C)C(=O)OC35C	4298.2	Semi standard non polar	33892256
Isophysalin B,1TBDMS,isomer #3	CC12C(=CCC3C1CCC1(O)C(=O)OC4(C)C5CC6(C)C(COC37OC14C6C7=O)C(=O)O5)C=CC=C2O[Si](C)(C)C(C)(C)C	4379.7	Semi standard non polar	33892256
Isophysalin B,2TBDMS,isomer #1	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)(CCC1C4CC=C2C=CCC(=O)C21C)C(=O)OC35C	4513.5	Semi standard non polar	33892256
Isophysalin B,2TBDMS,isomer #1	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)(CCC1C4CC=C2C=CCC(=O)C21C)C(=O)OC35C	4324.6	Standard non polar	33892256
Isophysalin B,2TBDMS,isomer #2	CC12C(=CCC3C1CCC1(O[Si](C)(C)C(C)(C)C)C(=O)OC4(C)C5CC6(C)C(COC37OC14C6C7=O)C(=O)O5)C=CC=C2O[Si](C)(C)C(C)(C)C	4585.8	Semi standard non polar	33892256
Isophysalin B,2TBDMS,isomer #2	CC12C(=CCC3C1CCC1(O[Si](C)(C)C(C)(C)C)C(=O)OC4(C)C5CC6(C)C(COC37OC14C6C7=O)C(=O)O5)C=CC=C2O[Si](C)(C)C(C)(C)C	4262.8	Standard non polar	33892256
Isophysalin B,2TBDMS,isomer #3	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O)(CCC1C4CC=C2C=CC=C(O[Si](C)(C)C(C)(C)C)C21C)C(=O)OC35C	4370.0	Semi standard non polar	33892256
Isophysalin B,2TBDMS,isomer #3	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O)(CCC1C4CC=C2C=CC=C(O[Si](C)(C)C(C)(C)C)C21C)C(=O)OC35C	4108.8	Standard non polar	33892256
Isophysalin B,3TBDMS,isomer #1	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)(CCC1C4CC=C2C=CC=C(O[Si](C)(C)C(C)(C)C)C21C)C(=O)OC35C	4516.8	Semi standard non polar	33892256
Isophysalin B,3TBDMS,isomer #1	CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)(CCC1C4CC=C2C=CC=C(O[Si](C)(C)C(C)(C)C)C21C)C(=O)OC35C	4299.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isophysalin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0900100000-42d739d100c2d48023fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isophysalin B GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-1900030000-c14d5121bafd85f21afc	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 - Isophysalin B 10V, Positive-QTOF	splash10-03di-0000690000-60570ba5a6edb1fce68d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 20V, Positive-QTOF	splash10-01ox-0100920000-6dabfd9f8a920691fdff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 40V, Positive-QTOF	splash10-0ktf-8900400000-c1d73a6289cb197cf8ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 10V, Negative-QTOF	splash10-0a4i-0000490000-a90e0824e2b75b396ee1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 20V, Negative-QTOF	splash10-0aor-0000940000-a326db048283dfb4d4f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 40V, Negative-QTOF	splash10-00ds-1910600000-743724e8dd993c3937c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 10V, Positive-QTOF	splash10-03di-0000190000-dfe95957edd518c62d6b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 20V, Positive-QTOF	splash10-03ec-0501950000-e54c3e8f7dc71ff0b64f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 40V, Positive-QTOF	splash10-0a4u-2901500000-bd19e22e2de707375ce7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 10V, Negative-QTOF	splash10-0a4i-0000090000-fba8e660fda6f9e81f56	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 20V, Negative-QTOF	splash10-0a4i-0000390000-faec354c6a1217395439	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophysalin B 40V, Negative-QTOF	splash10-069r-0302910000-f283e119feb7e07b1939	2021-09-25	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

FDB019326

KNApSAcK ID

Not Available

Chemspider ID

17262464

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22748169

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 Isophysalin B (HMDB0039697)

MOL for HMDB0039697 (Isophysalin B)

3D MOL for HMDB0039697 (Isophysalin B)

3D SDF for HMDB0039697 (Isophysalin B)

3D-SDF for HMDB0039697 (Isophysalin B)

PDB for HMDB0039697 (Isophysalin B)

3D PDB for HMDB0039697 (Isophysalin B)

SMILES for HMDB0039697 (Isophysalin B)

INCHI for HMDB0039697 (Isophysalin B)

Structure for HMDB0039697 (Isophysalin B)

3D Structure for HMDB0039697 (Isophysalin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra