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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:03:20 UTC

Update Date

2022-03-07 02:56:15 UTC

HMDB ID

HMDB0039557

Secondary Accession Numbers

HMDB39557

Metabolite Identification

Common Name

12alpha-Hydroxy-13,18-dehydroparain

Description

12alpha-Hydroxy-13,18-dehydroparain belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Based on a literature review a small amount of articles have been published on 12alpha-Hydroxy-13,18-dehydroparain.

Structure

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


  Mrv0541 05061311142D          

 27 30  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  6  1  0  0  0  0
 10  2  2  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20  3  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21  4  1  0  0  0  0
 21 11  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 15  2  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 19  2  0  0  0  0
 26  5  1  0  0  0  0
 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
 27 15  1  0  0  0  0
M  END

HMDB0039557
     RDKit          3D
12alpha-Hydroxy-13,18-dehydroparain
 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.2812    1.2286    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830    0.9931    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0564    2.1388    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    2.7972    1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453    1.5243    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    2.6591    0.8222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083    0.7510   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    0.2975   -0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676    0.0361   -2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465    1.2560   -0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665    2.3927   -0.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0807    0.9046    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    1.8345    1.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2109    1.9968    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414   -0.3828    0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -1.4686    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -2.6347    1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1370   -1.0245   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -2.0217   -0.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870   -1.6737   -1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7232   -2.7393   -0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394   -2.6275   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -3.5827   -0.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5198   -1.3099    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745   -0.3502    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -0.3205   -0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3881    0.1403   -1.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    0.4518    0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6847    2.2399    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076    2.8021   -0.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6993    3.6591    1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5395    0.8917    1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    2.8023    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5385    1.5565   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554    1.0355   -2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783   -0.5738   -2.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3844   -0.2625   -2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6824    2.7700    1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    2.3412   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7814    1.0435    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908   -0.7002    1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429   -1.8109   -0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2169   -3.5844    0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5264   -2.7861    1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7517   -2.4159    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390   -1.0106    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -2.1417   -1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057   -3.0223   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025   -1.9093   -2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2302   -0.9591   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -1.4398    1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8904   -0.5908    1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    0.8536   -1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9344   -0.7196   -2.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244    0.6653   -2.6521 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25  2  1  0
 26  7  1  0
 18  8  1  0
 26 20  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
M  END


  Mrv0541 05061311142D          

 27 30  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  6  1  0  0  0  0
 10  2  2  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20  3  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21  4  1  0  0  0  0
 21 11  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 15  2  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 19  2  0  0  0  0
 26  5  1  0  0  0  0
 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
 27 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039557

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C)C2CC3OC(=O)CC4C(=C)C(O)C(O)C(C34C)C2(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9,11-12,14,16-18,23-24H,2,7-8H2,1,3-5H3

> <INCHI_KEY>
CKRHSGZMMGXRKZ-UHFFFAOYSA-N

> <FORMULA>
C21H28O6

> <MOLECULAR_WEIGHT>
376.4434

> <EXACT_MASS>
376.188588628

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.19176465394881

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.0347527979999998

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.868273366610236

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.414310711217432

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3075115998765234

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
98.56829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039557
     RDKit          3D
12alpha-Hydroxy-13,18-dehydroparain
 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.2812    1.2286    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830    0.9931    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0564    2.1388    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    2.7972    1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453    1.5243    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    2.6591    0.8222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083    0.7510   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    0.2975   -0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676    0.0361   -2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465    1.2560   -0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665    2.3927   -0.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0807    0.9046    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    1.8345    1.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2109    1.9968    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414   -0.3828    0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -1.4686    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -2.6347    1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1370   -1.0245   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -2.0217   -0.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870   -1.6737   -1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7232   -2.7393   -0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394   -2.6275   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -3.5827   -0.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5198   -1.3099    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745   -0.3502    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -0.3205   -0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3881    0.1403   -1.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    0.4518    0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6847    2.2399    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076    2.8021   -0.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6993    3.6591    1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5395    0.8917    1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    2.8023    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5385    1.5565   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554    1.0355   -2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783   -0.5738   -2.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3844   -0.2625   -2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6824    2.7700    1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    2.3412   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7814    1.0435    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908   -0.7002    1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429   -1.8109   -0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2169   -3.5844    0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5264   -2.7861    1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7517   -2.4159    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390   -1.0106    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -2.1417   -1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057   -3.0223   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025   -1.9093   -2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2302   -0.9591   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -1.4398    1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8904   -0.5908    1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    0.8536   -1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9344   -0.7196   -2.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244    0.6653   -2.6521 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25  2  1  0
 26  7  1  0
 18  8  1  0
 26 20  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   26                                                            
CONECT    6    9   13                                                       
CONECT    7   11   14                                                       
CONECT    8   12   15                                                       
CONECT    9    1    6   11                                                  
CONECT   10    2   12   16                                                  
CONECT   11    7    9   21                                                  
CONECT   12    8   10   20                                                  
CONECT   13    6   19   26                                                  
CONECT   14    7   20   27                                                  
CONECT   15    8   22   27                                                  
CONECT   16   10   17   23                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   20   21                                                  
CONECT   19   13   21   25                                                  
CONECT   20    3   12   14   18                                             
CONECT   21    4   11   18   19                                             
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   19                                                            
CONECT   26    5   13                                                       
CONECT   27   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0039557
HETATM    1  C1  UNL     1      -4.281   1.229   0.691  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.983   0.993   0.607  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.056   2.139   0.641  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.247   2.797   1.856  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.645   1.524   0.724  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.156   2.659   0.822  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.408   0.751  -0.582  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.002   0.298  -0.729  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.268   0.036  -2.225  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.047   1.256  -0.357  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.067   2.393  -0.861  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.081   0.905   0.603  1.00  0.00           C  
HETATM   13  O4  UNL     1       3.859   1.834   1.268  1.00  0.00           O  
HETATM   14  C10 UNL     1       5.211   1.997   0.852  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.341  -0.383   0.902  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.544  -1.469   0.227  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.519  -2.635   1.194  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.137  -1.025  -0.012  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.456  -2.022  -0.911  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.987  -1.674  -1.132  1.00  0.00           C  
HETATM   21  O5  UNL     1      -1.723  -2.739  -0.498  1.00  0.00           O  
HETATM   22  C17 UNL     1      -3.039  -2.627  -0.206  1.00  0.00           C  
HETATM   23  O6  UNL     1      -3.826  -3.583  -0.305  1.00  0.00           O  
HETATM   24  C18 UNL     1      -3.520  -1.310   0.242  1.00  0.00           C  
HETATM   25  C19 UNL     1      -2.374  -0.350   0.481  1.00  0.00           C  
HETATM   26  C20 UNL     1      -1.433  -0.320  -0.729  1.00  0.00           C  
HETATM   27  C21 UNL     1      -2.388   0.140  -1.857  1.00  0.00           C  
HETATM   28  H1  UNL     1      -5.037   0.452   0.674  1.00  0.00           H  
HETATM   29  H2  UNL     1      -4.685   2.240   0.785  1.00  0.00           H  
HETATM   30  H3  UNL     1      -2.108   2.802  -0.221  1.00  0.00           H  
HETATM   31  H4  UNL     1      -2.699   3.659   1.756  1.00  0.00           H  
HETATM   32  H5  UNL     1      -0.539   0.892   1.609  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.421   2.802   1.752  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.539   1.556  -1.369  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.555   1.035  -2.683  1.00  0.00           H  
HETATM   36  H9  UNL     1       2.178  -0.574  -2.372  1.00  0.00           H  
HETATM   37  H10 UNL     1       0.384  -0.263  -2.775  1.00  0.00           H  
HETATM   38  H11 UNL     1       5.682   2.770   1.482  1.00  0.00           H  
HETATM   39  H12 UNL     1       5.244   2.341  -0.199  1.00  0.00           H  
HETATM   40  H13 UNL     1       5.781   1.044   0.962  1.00  0.00           H  
HETATM   41  H14 UNL     1       4.091  -0.700   1.595  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.043  -1.811  -0.692  1.00  0.00           H  
HETATM   43  H16 UNL     1       2.217  -3.584   0.713  1.00  0.00           H  
HETATM   44  H17 UNL     1       3.526  -2.786   1.658  1.00  0.00           H  
HETATM   45  H18 UNL     1       1.752  -2.416   1.987  1.00  0.00           H  
HETATM   46  H19 UNL     1       0.639  -1.011   0.980  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.006  -2.142  -1.867  1.00  0.00           H  
HETATM   48  H21 UNL     1       0.606  -3.022  -0.405  1.00  0.00           H  
HETATM   49  H22 UNL     1      -1.203  -1.909  -2.220  1.00  0.00           H  
HETATM   50  H23 UNL     1      -4.230  -0.959  -0.527  1.00  0.00           H  
HETATM   51  H24 UNL     1      -4.078  -1.440   1.187  1.00  0.00           H  
HETATM   52  H25 UNL     1      -1.890  -0.591   1.417  1.00  0.00           H  
HETATM   53  H26 UNL     1      -3.133   0.854  -1.474  1.00  0.00           H  
HETATM   54  H27 UNL     1      -2.934  -0.720  -2.272  1.00  0.00           H  
HETATM   55  H28 UNL     1      -1.824   0.665  -2.652  1.00  0.00           H  
CONECT    1    2    2   28   29
CONECT    2    3   25
CONECT    3    4    5   30
CONECT    4   31
CONECT    5    6    7   32
CONECT    6   33
CONECT    7    8   26   34
CONECT    8    9   10   18
CONECT    9   35   36   37
CONECT   10   11   11   12
CONECT   12   13   15   15
CONECT   13   14
CONECT   14   38   39   40
CONECT   15   16   41
CONECT   16   17   18   42
CONECT   17   43   44   45
CONECT   18   19   46
CONECT   19   20   47   48
CONECT   20   21   26   49
CONECT   21   22
CONECT   22   23   23   24
CONECT   24   25   50   51
CONECT   25   26   52
CONECT   26   27
CONECT   27   53   54   55
END

HMDB0039557
     RDKit          3D
12alpha-Hydroxy-13,18-dehydroparain
 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.2812    1.2286    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830    0.9931    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0564    2.1388    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    2.7972    1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453    1.5243    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    2.6591    0.8222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083    0.7510   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    0.2975   -0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676    0.0361   -2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465    1.2560   -0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665    2.3927   -0.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0807    0.9046    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    1.8345    1.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2109    1.9968    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414   -0.3828    0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -1.4686    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -2.6347    1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1370   -1.0245   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -2.0217   -0.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870   -1.6737   -1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7232   -2.7393   -0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394   -2.6275   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -3.5827   -0.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5198   -1.3099    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745   -0.3502    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -0.3205   -0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3881    0.1403   -1.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    0.4518    0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6847    2.2399    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076    2.8021   -0.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6993    3.6591    1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5395    0.8917    1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    2.8023    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5385    1.5565   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554    1.0355   -2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783   -0.5738   -2.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3844   -0.2625   -2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6824    2.7700    1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    2.3412   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7814    1.0435    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908   -0.7002    1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429   -1.8109   -0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2169   -3.5844    0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5264   -2.7861    1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7517   -2.4159    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390   -1.0106    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -2.1417   -1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057   -3.0223   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025   -1.9093   -2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2302   -0.9591   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -1.4398    1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8904   -0.5908    1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    0.8536   -1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9344   -0.7196   -2.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244    0.6653   -2.6521 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25  2  1  0
 26  7  1  0
 18  8  1  0
 26 20  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12a-Hydroxy-13,18-dehydroparain	Generator
12Α-hydroxy-13,18-dehydroparain	Generator
12a-Hydroxy-13,18-dehyroparain	HMDB

Chemical Formula

C₂₁H₂₈O₆

Average Molecular Weight

376.4434

Monoisotopic Molecular Weight

376.188588628

IUPAC Name

15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione

Traditional Name

15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(C)C2CC3OC(=O)CC4C(=C)C(O)C(O)C(C34C)C2(C)C1=O

InChI Identifier

InChI=1S/C21H28O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9,11-12,14,16-18,23-24H,2,7-8H2,1,3-5H3

InChI Key

CKRHSGZMMGXRKZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Cyclohexenone
Oxane
Pyran
Cyclic alcohol
Lactone
Ketone
1,2-diol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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: HMDB0039557)

Source

Endogenous

Endogenous (HMDB: HMDB0039557)

Animal

Animal (HMDB: HMDB0039557)

Exogenous

Food

Food (HMDB: HMDB0039557)

Exogenous (HMDB: HMDB0039557)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039557)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039557)

Lipid metabolism pathway (HMDB: HMDB0039557)

Cellular process

Cell signaling (HMDB: HMDB0039557)

Biochemical process

Lipid transport (HMDB: HMDB0039557)

Role

Biological role

Energy source (HMDB: HMDB0039557)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039557)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	238 - 241 °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	1.43 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.03	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.41	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.57 m³·mol⁻¹	ChemAxon
Polarizability	39.19 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]+	188.739	31661259
DarkChem	[M-H]-	182.923	31661259
DeepCCS	[M-2H]-	223.043	30932474
DeepCCS	[M+Na]+	198.653	30932474
AllCCS	[M+H]+	189.4	32859911
AllCCS	[M+H-H2O]+	186.8	32859911
AllCCS	[M+NH4]+	191.8	32859911
AllCCS	[M+Na]+	192.5	32859911
AllCCS	[M-H]-	193.3	32859911
AllCCS	[M+Na-2H]-	193.7	32859911
AllCCS	[M+HCOO]-	194.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.01 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1051 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2549.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	198.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	437.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	484.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	953.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	467.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1417.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	284.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	360.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	246.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	186.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	37.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12alpha-Hydroxy-13,18-dehydroparain	COC1=CC(C)C2CC3OC(=O)CC4C(=C)C(O)C(O)C(C34C)C2(C)C1=O	3600.4	Standard polar	33892256
12alpha-Hydroxy-13,18-dehydroparain	COC1=CC(C)C2CC3OC(=O)CC4C(=C)C(O)C(O)C(C34C)C2(C)C1=O	2837.5	Standard non polar	33892256
12alpha-Hydroxy-13,18-dehydroparain	COC1=CC(C)C2CC3OC(=O)CC4C(=C)C(O)C(O)C(C34C)C2(C)C1=O	3158.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12alpha-Hydroxy-13,18-dehydroparain,1TMS,isomer #1	C=C1C(O[Si](C)(C)C)C(O)C2C3(C)C(=O)C(OC)=CC(C)C3CC3OC(=O)CC1C32C	3045.5	Semi standard non polar	33892256
12alpha-Hydroxy-13,18-dehydroparain,1TMS,isomer #2	C=C1C(O)C(O[Si](C)(C)C)C2C3(C)C(=O)C(OC)=CC(C)C3CC3OC(=O)CC1C32C	3018.2	Semi standard non polar	33892256
12alpha-Hydroxy-13,18-dehydroparain,2TMS,isomer #1	C=C1C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2C3(C)C(=O)C(OC)=CC(C)C3CC3OC(=O)CC1C32C	2972.7	Semi standard non polar	33892256
12alpha-Hydroxy-13,18-dehydroparain,1TBDMS,isomer #1	C=C1C(O[Si](C)(C)C(C)(C)C)C(O)C2C3(C)C(=O)C(OC)=CC(C)C3CC3OC(=O)CC1C32C	3269.4	Semi standard non polar	33892256
12alpha-Hydroxy-13,18-dehydroparain,1TBDMS,isomer #2	C=C1C(O)C(O[Si](C)(C)C(C)(C)C)C2C3(C)C(=O)C(OC)=CC(C)C3CC3OC(=O)CC1C32C	3251.0	Semi standard non polar	33892256
12alpha-Hydroxy-13,18-dehydroparain,2TBDMS,isomer #1	C=C1C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2C3(C)C(=O)C(OC)=CC(C)C3CC3OC(=O)CC1C32C	3428.5	Semi standard non polar	33892256

Spectra

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

FDB019178

KNApSAcK ID

Not Available

Chemspider ID

35014820

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73081379

PDB ID

Not Available

ChEBI ID

175842

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 12alpha-Hydroxy-13,18-dehydroparain (HMDB0039557)

MOL for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

3D MOL for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

3D SDF for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

3D-SDF for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

PDB for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

3D PDB for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

SMILES for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

INCHI for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

Structure for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

3D Structure for HMDB0039557 (12alpha-Hydroxy-13,18-dehydroparain)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized