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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:54 UTC

Update Date

2022-03-07 02:52:33 UTC

HMDB ID

HMDB0030456

Secondary Accession Numbers

HMDB30456

Metabolite Identification

Common Name

Macrophorin B

Description

Macrophorin B belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Macrophorin B has been detected, but not quantified in, pomes. This could make macrophorin b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Macrophorin B.

Structure

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

  Mrv0541 02241210322D          

 27 30  0  0  0  0            999 V2000
    2.8172    1.0449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923    1.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -0.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548   -2.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -2.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6737   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6737   -0.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    3.1884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923    2.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423    1.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4825    1.0449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -2.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193   -3.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579   -3.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 26  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 26  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0030456
     RDKit          3D
Macrophorin B
 57 60  0  0  0  0  0  0  0  0999 V2000
   -0.3044   -2.7705    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654   -1.8689   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -2.2176   -1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5441   -0.8687   -1.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -0.0853   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    0.8842    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7683    0.0945    0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0158    1.6000   -1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688    1.8137    1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7504    2.8853    1.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075    1.4098    2.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9067    0.8209    1.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823    0.5438   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883    1.7672   -0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227   -0.5298   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712   -0.2404   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2712   -1.0665   -0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411   -2.3561   -0.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637   -1.9767   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628   -1.1266    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8545   -1.8251    1.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458    0.0581    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4774    0.8247    1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9939    1.8664    0.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1821    0.4656   -1.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1777   -0.2819   -1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1307   -0.2311   -2.9956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -3.7291    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923   -2.7016    1.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5289   -2.6993   -2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5463   -2.8003   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958   -1.0660   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862   -0.3515   -2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320   -0.8282    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662   -0.6008   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5156   -0.4079    1.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529    0.8506    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039    1.3964   -2.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0648    1.2954   -1.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066    2.6950   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    0.6939    2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    2.3083    2.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0249    1.4503    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048   -0.1746    1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.4533   -1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0055    2.2989   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7238    2.4924   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1572   -0.3819   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3435   -0.3319    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4551    0.8431   -0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1506   -2.3698   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704   -0.8282    1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1887   -1.3191    2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2957    0.1650    1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.1808    1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142    2.5466    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6987    1.3311   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  2  0
 15  2  1  0
 19 17  1  0
 13  5  1  0
 26 17  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
 20 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  0
M  END

  Mrv0541 02241210322D          

 27 30  0  0  0  0            999 V2000
    2.8172    1.0449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923    1.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -0.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548   -2.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -2.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6737   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6737   -0.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    3.1884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923    2.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423    1.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4825    1.0449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -2.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193   -3.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579   -3.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 26  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 26  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030456

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)C2CCC(=C)C(CC34OC3C(O)C(CO)=CC4=O)C2(C)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-12-5-6-15-20(2,3)16(24)7-8-21(15,4)14(12)10-22-17(25)9-13(11-23)18(26)19(22)27-22/h9,14-15,18-19,23,26H,1,5-8,10-11H2,2-4H3

> <INCHI_KEY>
ZJZYSAJQOPJREK-UHFFFAOYSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.4706

> <EXACT_MASS>
374.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.443444795797014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(5,5,8a-trimethyl-2-methylidene-6-oxo-decahydronaphthalen-1-yl)methyl]-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.4608547819999997

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.255302585565161

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.180562531231015

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7845052331241282

> <JCHEM_POLAR_SURFACE_AREA>
87.13

> <JCHEM_REFRACTIVITY>
101.35129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl)methyl]-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030456
     RDKit          3D
Macrophorin B
 57 60  0  0  0  0  0  0  0  0999 V2000
   -0.3044   -2.7705    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654   -1.8689   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -2.2176   -1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5441   -0.8687   -1.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -0.0853   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    0.8842    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7683    0.0945    0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0158    1.6000   -1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688    1.8137    1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7504    2.8853    1.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075    1.4098    2.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9067    0.8209    1.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823    0.5438   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883    1.7672   -0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227   -0.5298   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712   -0.2404   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2712   -1.0665   -0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411   -2.3561   -0.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637   -1.9767   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628   -1.1266    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8545   -1.8251    1.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458    0.0581    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4774    0.8247    1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9939    1.8664    0.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1821    0.4656   -1.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1777   -0.2819   -1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1307   -0.2311   -2.9956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -3.7291    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923   -2.7016    1.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5289   -2.6993   -2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5463   -2.8003   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958   -1.0660   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862   -0.3515   -2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320   -0.8282    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662   -0.6008   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5156   -0.4079    1.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529    0.8506    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039    1.3964   -2.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0648    1.2954   -1.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066    2.6950   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    0.6939    2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    2.3083    2.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0249    1.4503    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048   -0.1746    1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.4533   -1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0055    2.2989   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7238    2.4924   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1572   -0.3819   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3435   -0.3319    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4551    0.8431   -0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1506   -2.3698   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704   -0.8282    1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1887   -1.3191    2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2957    0.1650    1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.1808    1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142    2.5466    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6987    1.3311   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  2  0
 15  2  1  0
 19 17  1  0
 13  5  1  0
 26 17  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
 20 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       5.259   1.950   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.719   1.950   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.949   0.618   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.179  -0.716   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.409   0.618   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.074  -0.151   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.074  -1.691   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.409  -2.461   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.741  -1.691   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.409  -4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.074  -4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.260  -4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.258  -2.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.258  -0.921   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.949   5.952   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.719   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.949   3.285   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.409   3.285   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.639   1.950   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.901   1.950   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.592  -1.691   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.927  -2.461   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.927  -4.001   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.259  -4.771   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.583  -5.952   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.592  -4.771   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.601  -5.952   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    3    4    6   19                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13    7   12   14   21                                             
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16   15   17                                                       
CONECT   17    2   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19    5   18   20                                                  
CONECT   20   19                                                            
CONECT   21   13   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23                                                            
CONECT   25   26                                                            
CONECT   26   12   23   25   27                                             
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0030456
HETATM    1  C1  UNL     1      -0.304  -2.771   0.545  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.665  -1.869  -0.319  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.845  -2.218  -1.219  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.544  -0.869  -1.457  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.467  -0.085  -0.194  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.577   0.884   0.009  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.768   0.094   0.568  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.016   1.600  -1.221  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.169   1.814   1.113  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.750   2.885   1.164  1.00  0.00           O  
HETATM   11  C10 UNL     1      -2.108   1.410   2.073  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.907   0.821   1.427  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.082   0.544  -0.042  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.888   1.767  -0.861  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.123  -0.530  -0.546  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.271  -0.240  -0.174  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.271  -1.066  -0.925  1.00  0.00           C  
HETATM   18  O2  UNL     1       2.141  -2.356  -0.751  1.00  0.00           O  
HETATM   19  C17 UNL     1       3.264  -1.977  -0.205  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.763  -1.127   0.867  1.00  0.00           C  
HETATM   21  O3  UNL     1       4.855  -1.825   1.476  1.00  0.00           O  
HETATM   22  C19 UNL     1       4.446   0.058   0.227  1.00  0.00           C  
HETATM   23  C20 UNL     1       5.477   0.825   1.012  1.00  0.00           C  
HETATM   24  O4  UNL     1       5.994   1.866   0.279  1.00  0.00           O  
HETATM   25  C21 UNL     1       4.182   0.466  -1.007  1.00  0.00           C  
HETATM   26  C22 UNL     1       3.178  -0.282  -1.767  1.00  0.00           C  
HETATM   27  O5  UNL     1       3.131  -0.231  -2.996  1.00  0.00           O  
HETATM   28  H1  UNL     1      -0.852  -3.729   0.590  1.00  0.00           H  
HETATM   29  H2  UNL     1       0.492  -2.702   1.280  1.00  0.00           H  
HETATM   30  H3  UNL     1      -1.529  -2.699  -2.140  1.00  0.00           H  
HETATM   31  H4  UNL     1      -2.546  -2.800  -0.590  1.00  0.00           H  
HETATM   32  H5  UNL     1      -3.596  -1.066  -1.755  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.086  -0.351  -2.324  1.00  0.00           H  
HETATM   34  H7  UNL     1      -2.532  -0.828   0.657  1.00  0.00           H  
HETATM   35  H8  UNL     1      -5.166  -0.601  -0.203  1.00  0.00           H  
HETATM   36  H9  UNL     1      -4.516  -0.408   1.502  1.00  0.00           H  
HETATM   37  H10 UNL     1      -5.553   0.851   0.781  1.00  0.00           H  
HETATM   38  H11 UNL     1      -3.404   1.396  -2.118  1.00  0.00           H  
HETATM   39  H12 UNL     1      -5.065   1.295  -1.511  1.00  0.00           H  
HETATM   40  H13 UNL     1      -4.107   2.695  -1.000  1.00  0.00           H  
HETATM   41  H14 UNL     1      -2.590   0.694   2.800  1.00  0.00           H  
HETATM   42  H15 UNL     1      -1.858   2.308   2.676  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.025   1.450   1.646  1.00  0.00           H  
HETATM   44  H17 UNL     1      -0.705  -0.175   1.920  1.00  0.00           H  
HETATM   45  H18 UNL     1      -0.714   1.453  -1.926  1.00  0.00           H  
HETATM   46  H19 UNL     1       0.006   2.299  -0.474  1.00  0.00           H  
HETATM   47  H20 UNL     1      -1.724   2.492  -0.802  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.157  -0.382  -1.685  1.00  0.00           H  
HETATM   49  H22 UNL     1       1.344  -0.332   0.938  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.455   0.843  -0.390  1.00  0.00           H  
HETATM   51  H24 UNL     1       4.151  -2.370  -0.827  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.070  -0.828   1.668  1.00  0.00           H  
HETATM   53  H26 UNL     1       5.189  -1.319   2.242  1.00  0.00           H  
HETATM   54  H27 UNL     1       6.296   0.165   1.350  1.00  0.00           H  
HETATM   55  H28 UNL     1       4.951   1.181   1.925  1.00  0.00           H  
HETATM   56  H29 UNL     1       5.314   2.547   0.134  1.00  0.00           H  
HETATM   57  H30 UNL     1       4.699   1.331  -1.442  1.00  0.00           H  
CONECT    1    2    2   28   29
CONECT    2    3   15
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   13   34
CONECT    6    7    8    9
CONECT    7   35   36   37
CONECT    8   38   39   40
CONECT    9   10   10   11
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   15
CONECT   14   45   46   47
CONECT   15   16   48
CONECT   16   17   49   50
CONECT   17   18   19   26
CONECT   18   19
CONECT   19   20   51
CONECT   20   21   22   52
CONECT   21   53
CONECT   22   23   25   25
CONECT   23   24   54   55
CONECT   24   56
CONECT   25   26   57
CONECT   26   27   27
END

HMDB0030456
     RDKit          3D
Macrophorin B
 57 60  0  0  0  0  0  0  0  0999 V2000
   -0.3044   -2.7705    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654   -1.8689   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -2.2176   -1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5441   -0.8687   -1.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -0.0853   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    0.8842    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7683    0.0945    0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0158    1.6000   -1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688    1.8137    1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7504    2.8853    1.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075    1.4098    2.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9067    0.8209    1.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823    0.5438   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883    1.7672   -0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227   -0.5298   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712   -0.2404   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2712   -1.0665   -0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411   -2.3561   -0.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637   -1.9767   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628   -1.1266    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8545   -1.8251    1.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458    0.0581    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4774    0.8247    1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9939    1.8664    0.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1821    0.4656   -1.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1777   -0.2819   -1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1307   -0.2311   -2.9956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -3.7291    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923   -2.7016    1.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5289   -2.6993   -2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5463   -2.8003   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958   -1.0660   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862   -0.3515   -2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320   -0.8282    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662   -0.6008   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5156   -0.4079    1.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529    0.8506    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039    1.3964   -2.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0648    1.2954   -1.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066    2.6950   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    0.6939    2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    2.3083    2.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0249    1.4503    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048   -0.1746    1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.4533   -1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0055    2.2989   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7238    2.4924   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1572   -0.3819   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3435   -0.3319    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4551    0.8431   -0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1506   -2.3698   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704   -0.8282    1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1887   -1.3191    2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2957    0.1650    1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.1808    1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142    2.5466    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6987    1.3311   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  2  0
 15  2  1  0
 19 17  1  0
 13  5  1  0
 26 17  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
 20 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₅

Average Molecular Weight

374.4706

Monoisotopic Molecular Weight

374.20932407

IUPAC Name

1-[(5,5,8a-trimethyl-2-methylidene-6-oxo-decahydronaphthalen-1-yl)methyl]-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

Traditional Name

1-[(5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl)methyl]-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

CAS Registry Number

85764-12-1

SMILES

CC1(C)C2CCC(=C)C(CC34OC3C(O)C(CO)=CC4=O)C2(C)CCC1=O

InChI Identifier

InChI=1S/C22H30O5/c1-12-5-6-15-20(2,3)16(24)7-8-21(15,4)14(12)10-22-17(25)9-13(11-23)18(26)19(22)27-22/h9,14-15,18-19,23,26H,1,5-8,10-11H2,2-4H3

InChI Key

ZJZYSAJQOPJREK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030456)

Source

Endogenous

Endogenous (HMDB: HMDB0030456)

Plant

Plant (HMDB: HMDB0030456)

Exogenous

Food

Food (HMDB: HMDB0030456)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Exogenous (HMDB: HMDB0030456)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0030456)

Role

Biological role

Energy source (HMDB: HMDB0030456)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030456)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	107 - 110 °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	0.12 g/L	ALOGPS
logP	1.89	ALOGPS
logP	2.46	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.35 m³·mol⁻¹	ChemAxon
Polarizability	40.44 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	186.121	31661259
DarkChem	[M-H]-	178.496	31661259
DeepCCS	[M-2H]-	223.776	30932474
DeepCCS	[M+Na]+	199.34	30932474
AllCCS	[M+H]+	192.1	32859911
AllCCS	[M+H-H2O]+	189.5	32859911
AllCCS	[M+NH4]+	194.5	32859911
AllCCS	[M+Na]+	195.2	32859911
AllCCS	[M-H]-	195.1	32859911
AllCCS	[M+Na-2H]-	195.7	32859911
AllCCS	[M+HCOO]-	196.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Macrophorin B	CC1(C)C2CCC(=C)C(CC34OC3C(O)C(CO)=CC4=O)C2(C)CCC1=O	3199.9	Standard polar	33892256
Macrophorin B	CC1(C)C2CCC(=C)C(CC34OC3C(O)C(CO)=CC4=O)C2(C)CCC1=O	2864.4	Standard non polar	33892256
Macrophorin B	CC1(C)C2CCC(=C)C(CC34OC3C(O)C(CO)=CC4=O)C2(C)CCC1=O	3274.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Macrophorin B,1TMS,isomer #1	C=C1CCC2C(C)(C)C(=O)CCC2(C)C1CC12OC1C(O[Si](C)(C)C)C(CO)=CC2=O	3024.0	Semi standard non polar	33892256
Macrophorin B,1TMS,isomer #2	C=C1CCC2C(C)(C)C(=O)CCC2(C)C1CC12OC1C(O)C(CO[Si](C)(C)C)=CC2=O	3045.3	Semi standard non polar	33892256
Macrophorin B,1TMS,isomer #3	C=C1CCC2C(C)(C)C(O[Si](C)(C)C)=CCC2(C)C1CC12OC1C(O)C(CO)=CC2=O	2993.3	Semi standard non polar	33892256
Macrophorin B,2TMS,isomer #1	C=C1CCC2C(C)(C)C(=O)CCC2(C)C1CC12OC1C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=CC2=O	3052.4	Semi standard non polar	33892256
Macrophorin B,2TMS,isomer #2	C=C1CCC2C(C)(C)C(O[Si](C)(C)C)=CCC2(C)C1CC12OC1C(O[Si](C)(C)C)C(CO)=CC2=O	2950.5	Semi standard non polar	33892256
Macrophorin B,2TMS,isomer #3	C=C1CCC2C(C)(C)C(O[Si](C)(C)C)=CCC2(C)C1CC12OC1C(O)C(CO[Si](C)(C)C)=CC2=O	2977.4	Semi standard non polar	33892256
Macrophorin B,3TMS,isomer #1	C=C1CCC2C(C)(C)C(O[Si](C)(C)C)=CCC2(C)C1CC12OC1C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=CC2=O	2949.6	Semi standard non polar	33892256
Macrophorin B,3TMS,isomer #1	C=C1CCC2C(C)(C)C(O[Si](C)(C)C)=CCC2(C)C1CC12OC1C(O[Si](C)(C)C)C(CO[Si](C)(C)C)=CC2=O	2900.1	Standard non polar	33892256
Macrophorin B,1TBDMS,isomer #1	C=C1CCC2C(C)(C)C(=O)CCC2(C)C1CC12OC1C(O[Si](C)(C)C(C)(C)C)C(CO)=CC2=O	3251.7	Semi standard non polar	33892256
Macrophorin B,1TBDMS,isomer #2	C=C1CCC2C(C)(C)C(=O)CCC2(C)C1CC12OC1C(O)C(CO[Si](C)(C)C(C)(C)C)=CC2=O	3288.3	Semi standard non polar	33892256
Macrophorin B,1TBDMS,isomer #3	C=C1CCC2C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C1CC12OC1C(O)C(CO)=CC2=O	3223.7	Semi standard non polar	33892256
Macrophorin B,2TBDMS,isomer #1	C=C1CCC2C(C)(C)C(=O)CCC2(C)C1CC12OC1C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=CC2=O	3500.8	Semi standard non polar	33892256
Macrophorin B,2TBDMS,isomer #2	C=C1CCC2C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C1CC12OC1C(O[Si](C)(C)C(C)(C)C)C(CO)=CC2=O	3405.7	Semi standard non polar	33892256
Macrophorin B,2TBDMS,isomer #3	C=C1CCC2C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C1CC12OC1C(O)C(CO[Si](C)(C)C(C)(C)C)=CC2=O	3425.6	Semi standard non polar	33892256
Macrophorin B,3TBDMS,isomer #1	C=C1CCC2C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C1CC12OC1C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=CC2=O	3607.7	Semi standard non polar	33892256
Macrophorin B,3TBDMS,isomer #1	C=C1CCC2C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C1CC12OC1C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=CC2=O	3439.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Macrophorin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-053i-5149000000-352eb0760c07efbcf118	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macrophorin B GC-MS (2 TMS) - 70eV, Positive	splash10-0gb9-4690520000-f84e4da7bf816fa1a60c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macrophorin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Macrophorin B 10V, Positive-QTOF	splash10-0a6r-0019000000-45610acc822f9ff32886	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 20V, Positive-QTOF	splash10-0a4r-0239000000-0b9e52dc7239873cc3b8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 40V, Positive-QTOF	splash10-05n0-3985000000-49f74ea852e0f103b59d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 10V, Negative-QTOF	splash10-00di-0109000000-38a3c75f95c75e2b8996	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 20V, Negative-QTOF	splash10-0596-0019000000-2a8ec15b363386dccc55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 40V, Negative-QTOF	splash10-05cu-9664000000-06c5285b2716166ffcfb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 10V, Negative-QTOF	splash10-00di-0009000000-4beec9273b3cb310a076	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 20V, Negative-QTOF	splash10-00di-0009000000-086a28749b5c75724a42	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 40V, Negative-QTOF	splash10-0l6r-6779000000-930a6244ff420f7b7843	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 10V, Positive-QTOF	splash10-0a70-0329000000-25ef06699bda2b4b9421	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 20V, Positive-QTOF	splash10-000i-1966000000-7302b21ba91bcf33c37d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macrophorin B 40V, Positive-QTOF	splash10-0kbo-1921000000-f1116f8de8b11216242b	2021-09-24	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

FDB002324

KNApSAcK ID

Not Available

Chemspider ID

35013200

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751020

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Macrophorin B (HMDB0030456)

MOL for HMDB0030456 (Macrophorin B)

3D MOL for HMDB0030456 (Macrophorin B)

3D SDF for HMDB0030456 (Macrophorin B)

3D-SDF for HMDB0030456 (Macrophorin B)

PDB for HMDB0030456 (Macrophorin B)

3D PDB for HMDB0030456 (Macrophorin B)

SMILES for HMDB0030456 (Macrophorin B)

INCHI for HMDB0030456 (Macrophorin B)

Structure for HMDB0030456 (Macrophorin B)

3D Structure for HMDB0030456 (Macrophorin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra