Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:55:10 UTC

Update Date

2022-03-07 02:56:34 UTC

HMDB ID

HMDB0040390

Secondary Accession Numbers

HMDB40390

Metabolite Identification

Common Name

Erinacine B

Description

Erinacine B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a significant number of articles have been published on Erinacine B.

Structure

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


  Mrv0541 05061311482D          

 31 35  0  0  0  0            999 V2000
    1.2510    0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461    0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287   -2.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288   -1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960    0.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6794   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693   -1.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879   -2.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157   -2.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882    1.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8257   -2.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1090    0.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2161   -0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234   -0.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1435   -1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9726   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6430   -0.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061   -0.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8248   -0.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883   -1.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5070   -1.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -2.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3949   -1.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4094    0.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9617   -1.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9608   -0.0251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0074   -2.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3243   -0.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888   -1.7587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 14  5  2  0  0  0  0
 14 11  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  2  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24  3  1  0  0  0  0
 24  8  1  0  0  0  0
 24  9  1  0  0  0  0
 24 18  1  0  0  0  0
 25  4  1  0  0  0  0
 25 10  1  0  0  0  0
 25 16  1  0  0  0  0
 25 22  1  0  0  0  0
 26 11  2  0  0  0  0
 27 17  1  0  0  0  0
 28 19  1  0  0  0  0
 29 12  1  0  0  0  0
 29 23  1  0  0  0  0
 30 20  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  1  0  0  0  0
 31 23  1  0  0  0  0
M  END

HMDB0040390
     RDKit          3D
Erinacine B
 67 71  0  0  0  0  0  0  0  0999 V2000
   -2.0827    3.1209   -0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9635    1.8305   -1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215    2.0822   -2.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6572    0.7788   -0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729   -0.3813   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363   -1.1782   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.8382   -1.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8777   -1.9978   -1.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -2.2301   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -3.3805   -1.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4812   -4.0964   -2.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2088   -1.5190    0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3007   -0.6768   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3723    0.3097    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1771    1.2218    0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059    2.1422    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    3.1454    1.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509    2.6255    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824    3.3778    1.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859    1.1756    0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3155    0.7130   -0.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9976    0.5623    0.5630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996   -0.7682    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2580   -1.4247    0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   -2.8966    1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -0.8820    1.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5368   -1.3634    1.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1928   -1.1407    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4752   -2.4958   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049   -0.2925    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9828    0.9917   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8799    2.8061    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3341    3.8530   -0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0762    3.5549   -0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9192    1.7122   -1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1062    1.1436   -3.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    2.8057   -3.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611    2.5642   -2.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -2.2093   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775    0.0385   -1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664   -0.7816   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -2.6326   -2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945   -3.6745   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825   -2.2880    0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.1222    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    1.7379   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725    3.7936    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5064    3.8131    0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    2.7594   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4983    4.1247    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2696    1.1025    1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1679    0.2904    0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266   -0.7974    1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -3.4995    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715   -3.0194    1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9407   -3.2980    1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395    0.2081    1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -1.3082    2.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456   -2.3813    2.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911   -0.7016    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -2.5303   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9884   -3.2793    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833   -2.6530    0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7764   -0.0950    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2270   -0.7187   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7043    1.3163   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302    1.8504    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15 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
 28 30  1  0
 30 31  1  0
 31  4  1  0
 28  5  1  0
 24  6  1  0
 23 12  1  0
 20 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
 10 43  1  0
 12 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
M  END


  Mrv0541 05061311482D          

 31 35  0  0  0  0            999 V2000
    1.2510    0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461    0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287   -2.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288   -1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960    0.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6794   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693   -1.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879   -2.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157   -2.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882    1.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8257   -2.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1090    0.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2161   -0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234   -0.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1435   -1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9726   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6430   -0.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061   -0.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8248   -0.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883   -1.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5070   -1.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -2.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3949   -1.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4094    0.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9617   -1.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9608   -0.0251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0074   -2.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3243   -0.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888   -1.7587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 14  5  2  0  0  0  0
 14 11  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  2  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24  3  1  0  0  0  0
 24  8  1  0  0  0  0
 24  9  1  0  0  0  0
 24 18  1  0  0  0  0
 25  4  1  0  0  0  0
 25 10  1  0  0  0  0
 25 16  1  0  0  0  0
 25 22  1  0  0  0  0
 26 11  2  0  0  0  0
 27 17  1  0  0  0  0
 28 19  1  0  0  0  0
 29 12  1  0  0  0  0
 29 23  1  0  0  0  0
 30 20  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  1  0  0  0  0
 31 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040390

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C2C3CC=C(C=O)C4OC5C(O)C(O)COC5OC4C3(C)CCC2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O6/c1-13(2)15-7-8-24(3)9-10-25(4)16(18(15)24)6-5-14(11-26)20-22(25)31-23-21(30-20)19(28)17(27)12-29-23/h5,11,13,16-17,19-23,27-28H,6-10,12H2,1-4H3

> <INCHI_KEY>
BEECYWPPXWUPIT-UHFFFAOYSA-N

> <FORMULA>
C25H36O6

> <MOLECULAR_WEIGHT>
432.5497

> <EXACT_MASS>
432.251188884

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
47.79641753624732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17,18-dihydroxy-2,5-dimethyl-8-(propan-2-yl)-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-13-carbaldehyde

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.621686638

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.333538293492957

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.828719408185322

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526821513263312

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
115.68589999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17,18-dihydroxy-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-13-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040390
     RDKit          3D
Erinacine B
 67 71  0  0  0  0  0  0  0  0999 V2000
   -2.0827    3.1209   -0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9635    1.8305   -1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215    2.0822   -2.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6572    0.7788   -0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729   -0.3813   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363   -1.1782   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.8382   -1.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8777   -1.9978   -1.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -2.2301   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -3.3805   -1.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4812   -4.0964   -2.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2088   -1.5190    0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3007   -0.6768   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3723    0.3097    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1771    1.2218    0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059    2.1422    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    3.1454    1.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509    2.6255    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824    3.3778    1.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859    1.1756    0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3155    0.7130   -0.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9976    0.5623    0.5630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996   -0.7682    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2580   -1.4247    0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   -2.8966    1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -0.8820    1.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5368   -1.3634    1.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1928   -1.1407    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4752   -2.4958   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049   -0.2925    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9828    0.9917   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8799    2.8061    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3341    3.8530   -0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0762    3.5549   -0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9192    1.7122   -1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1062    1.1436   -3.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    2.8057   -3.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611    2.5642   -2.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -2.2093   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775    0.0385   -1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664   -0.7816   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -2.6326   -2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945   -3.6745   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825   -2.2880    0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.1222    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    1.7379   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725    3.7936    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5064    3.8131    0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    2.7594   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4983    4.1247    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2696    1.1025    1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1679    0.2904    0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266   -0.7974    1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -3.4995    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715   -3.0194    1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9407   -3.2980    1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395    0.2081    1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -1.3082    2.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456   -2.3813    2.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911   -0.7016    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -2.5303   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9884   -3.2793    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833   -2.6530    0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7764   -0.0950    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2270   -0.7187   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7043    1.3163   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302    1.8504    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15 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
 28 30  1  0
 30 31  1  0
 31  4  1  0
 28  5  1  0
 24  6  1  0
 23 12  1  0
 20 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
 10 43  1  0
 12 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 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       2.335   0.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.939   0.934   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.094  -5.266   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.387  -3.467   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.019   0.975   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.868  -0.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.116  -2.763   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.897  -4.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.654  -4.652   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.056  -4.014   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.431   1.966   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.608  -4.114   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.804  -0.107   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.537   0.713   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.137  -1.610   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.950  -1.586   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.201  -2.692   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.549  -2.225   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.267  -1.468   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.278  -0.637   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.740  -1.665   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.685  -2.059   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.146  -3.086   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.401  -3.757   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.204  -2.481   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.964   1.818   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      16.729  -2.496   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      14.860  -0.047   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.080  -4.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      11.805  -0.441   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.619  -3.283   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5    6   14                                                       
CONECT    6    5   16                                                       
CONECT    7    8   15                                                       
CONECT    8    7   24                                                       
CONECT    9   10   24                                                       
CONECT   10    9   25                                                       
CONECT   11   14   26                                                       
CONECT   12   17   29                                                       
CONECT   13    1    2   15                                                  
CONECT   14    5   11   20                                                  
CONECT   15    7   13   18                                                  
CONECT   16    6   18   25                                                  
CONECT   17   12   19   27                                                  
CONECT   18   15   16   24                                                  
CONECT   19   17   21   28                                                  
CONECT   20   14   22   30                                                  
CONECT   21   19   23   30                                                  
CONECT   22   20   25   31                                                  
CONECT   23   21   29   31                                                  
CONECT   24    3    8    9   18                                             
CONECT   25    4   10   16   22                                             
CONECT   26   11                                                            
CONECT   27   17                                                            
CONECT   28   19                                                            
CONECT   29   12   23                                                       
CONECT   30   20   21                                                       
CONECT   31   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

COMPND    HMDB0040390
HETATM    1  C1  UNL     1      -2.083   3.121  -0.627  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.964   1.831  -1.470  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.821   2.082  -2.679  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.657   0.779  -0.649  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.173  -0.381  -0.348  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.936  -1.178  -0.577  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.077  -0.838  -1.707  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.878  -1.998  -1.887  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.844  -2.230  -1.019  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.669  -3.380  -1.341  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.481  -4.096  -2.359  1.00  0.00           O  
HETATM   12  C11 UNL     1       2.209  -1.519   0.201  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.301  -0.677  -0.008  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.372   0.310   0.973  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.177   1.222   0.729  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.206   2.142   1.773  1.00  0.00           O  
HETATM   17  C14 UNL     1       3.092   3.145   1.400  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.251   2.626   0.629  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.382   3.378   1.014  1.00  0.00           O  
HETATM   20  C16 UNL     1       4.586   1.176   0.859  1.00  0.00           C  
HETATM   21  O5  UNL     1       5.316   0.713  -0.258  1.00  0.00           O  
HETATM   22  O6  UNL     1       0.998   0.562   0.563  1.00  0.00           O  
HETATM   23  C17 UNL     1       1.100  -0.768   0.862  1.00  0.00           C  
HETATM   24  C18 UNL     1      -0.258  -1.425   0.735  1.00  0.00           C  
HETATM   25  C19 UNL     1      -0.049  -2.897   1.046  1.00  0.00           C  
HETATM   26  C20 UNL     1      -1.105  -0.882   1.869  1.00  0.00           C  
HETATM   27  C21 UNL     1      -2.537  -1.363   1.812  1.00  0.00           C  
HETATM   28  C22 UNL     1      -3.193  -1.141   0.484  1.00  0.00           C  
HETATM   29  C23 UNL     1      -3.475  -2.496  -0.142  1.00  0.00           C  
HETATM   30  C24 UNL     1      -4.405  -0.292   0.532  1.00  0.00           C  
HETATM   31  C25 UNL     1      -3.983   0.992  -0.083  1.00  0.00           C  
HETATM   32  H1  UNL     1      -1.880   2.806   0.434  1.00  0.00           H  
HETATM   33  H2  UNL     1      -1.334   3.853  -0.942  1.00  0.00           H  
HETATM   34  H3  UNL     1      -3.076   3.555  -0.697  1.00  0.00           H  
HETATM   35  H4  UNL     1      -0.919   1.712  -1.619  1.00  0.00           H  
HETATM   36  H5  UNL     1      -3.106   1.144  -3.212  1.00  0.00           H  
HETATM   37  H6  UNL     1      -2.367   2.806  -3.384  1.00  0.00           H  
HETATM   38  H7  UNL     1      -3.761   2.564  -2.318  1.00  0.00           H  
HETATM   39  H8  UNL     1      -1.342  -2.209  -0.862  1.00  0.00           H  
HETATM   40  H9  UNL     1       0.577   0.039  -1.658  1.00  0.00           H  
HETATM   41  H10 UNL     1      -0.666  -0.782  -2.636  1.00  0.00           H  
HETATM   42  H11 UNL     1       0.754  -2.633  -2.740  1.00  0.00           H  
HETATM   43  H12 UNL     1       3.494  -3.674  -0.705  1.00  0.00           H  
HETATM   44  H13 UNL     1       2.582  -2.288   0.919  1.00  0.00           H  
HETATM   45  H14 UNL     1       3.346  -0.122   1.994  1.00  0.00           H  
HETATM   46  H15 UNL     1       2.405   1.738  -0.243  1.00  0.00           H  
HETATM   47  H16 UNL     1       3.372   3.794   2.255  1.00  0.00           H  
HETATM   48  H17 UNL     1       2.506   3.813   0.701  1.00  0.00           H  
HETATM   49  H18 UNL     1       4.152   2.759  -0.484  1.00  0.00           H  
HETATM   50  H19 UNL     1       5.498   4.125   0.369  1.00  0.00           H  
HETATM   51  H20 UNL     1       5.270   1.103   1.734  1.00  0.00           H  
HETATM   52  H21 UNL     1       6.168   0.290   0.015  1.00  0.00           H  
HETATM   53  H22 UNL     1       1.327  -0.797   1.972  1.00  0.00           H  
HETATM   54  H23 UNL     1      -0.012  -3.499   0.109  1.00  0.00           H  
HETATM   55  H24 UNL     1       0.872  -3.019   1.659  1.00  0.00           H  
HETATM   56  H25 UNL     1      -0.941  -3.298   1.614  1.00  0.00           H  
HETATM   57  H26 UNL     1      -1.039   0.208   1.967  1.00  0.00           H  
HETATM   58  H27 UNL     1      -0.671  -1.308   2.808  1.00  0.00           H  
HETATM   59  H28 UNL     1      -2.646  -2.381   2.212  1.00  0.00           H  
HETATM   60  H29 UNL     1      -3.091  -0.702   2.540  1.00  0.00           H  
HETATM   61  H30 UNL     1      -3.307  -2.530  -1.224  1.00  0.00           H  
HETATM   62  H31 UNL     1      -2.988  -3.279   0.443  1.00  0.00           H  
HETATM   63  H32 UNL     1      -4.583  -2.653   0.038  1.00  0.00           H  
HETATM   64  H33 UNL     1      -4.776  -0.095   1.564  1.00  0.00           H  
HETATM   65  H34 UNL     1      -5.227  -0.719  -0.100  1.00  0.00           H  
HETATM   66  H35 UNL     1      -4.704   1.316  -0.904  1.00  0.00           H  
HETATM   67  H36 UNL     1      -4.030   1.850   0.631  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4   35
CONECT    3   36   37   38
CONECT    4    5    5   31
CONECT    5    6   28
CONECT    6    7   24   39
CONECT    7    8   40   41
CONECT    8    9    9   42
CONECT    9   10   12
CONECT   10   11   11   43
CONECT   12   13   23   44
CONECT   13   14
CONECT   14   15   20   45
CONECT   15   16   22   46
CONECT   16   17
CONECT   17   18   47   48
CONECT   18   19   20   49
CONECT   19   50
CONECT   20   21   51
CONECT   21   52
CONECT   22   23
CONECT   23   24   53
CONECT   24   25   26
CONECT   25   54   55   56
CONECT   26   27   57   58
CONECT   27   28   59   60
CONECT   28   29   30
CONECT   29   61   62   63
CONECT   30   31   64   65
CONECT   31   66   67
END

HMDB0040390
     RDKit          3D
Erinacine B
 67 71  0  0  0  0  0  0  0  0999 V2000
   -2.0827    3.1209   -0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9635    1.8305   -1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215    2.0822   -2.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6572    0.7788   -0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729   -0.3813   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363   -1.1782   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.8382   -1.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8777   -1.9978   -1.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -2.2301   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -3.3805   -1.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4812   -4.0964   -2.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2088   -1.5190    0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3007   -0.6768   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3723    0.3097    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1771    1.2218    0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059    2.1422    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    3.1454    1.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509    2.6255    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824    3.3778    1.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859    1.1756    0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3155    0.7130   -0.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9976    0.5623    0.5630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996   -0.7682    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2580   -1.4247    0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   -2.8966    1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -0.8820    1.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5368   -1.3634    1.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1928   -1.1407    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4752   -2.4958   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049   -0.2925    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9828    0.9917   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8799    2.8061    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3341    3.8530   -0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0762    3.5549   -0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9192    1.7122   -1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1062    1.1436   -3.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    2.8057   -3.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611    2.5642   -2.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -2.2093   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775    0.0385   -1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664   -0.7816   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -2.6326   -2.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945   -3.6745   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825   -2.2880    0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.1222    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    1.7379   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725    3.7936    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5064    3.8131    0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    2.7594   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4983    4.1247    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2696    1.1025    1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1679    0.2904    0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266   -0.7974    1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -3.4995    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715   -3.0194    1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9407   -3.2980    1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395    0.2081    1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -1.3082    2.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456   -2.3813    2.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911   -0.7016    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -2.5303   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9884   -3.2793    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833   -2.6530    0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7764   -0.0950    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2270   -0.7187   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7043    1.3163   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302    1.8504    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15 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
 28 30  1  0
 30 31  1  0
 31  4  1  0
 28  5  1  0
 24  6  1  0
 23 12  1  0
 20 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
 10 43  1  0
 12 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Erinacine b	MeSH

Chemical Formula

C₂₅H₃₆O₆

Average Molecular Weight

432.5497

Monoisotopic Molecular Weight

432.251188884

IUPAC Name

17,18-dihydroxy-2,5-dimethyl-8-(propan-2-yl)-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-13-carbaldehyde

Traditional Name

17,18-dihydroxy-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-13-carbaldehyde

CAS Registry Number

156101-08-5

SMILES

CC(C)C1=C2C3CC=C(C=O)C4OC5C(O)C(O)COC5OC4C3(C)CCC2(C)CC1

InChI Identifier

InChI=1S/C25H36O6/c1-13(2)15-7-8-24(3)9-10-25(4)16(18(15)24)6-5-14(11-26)20-22(25)31-23-21(30-20)19(28)17(27)12-29-23/h5,11,13,16-17,19-23,27-28H,6-10,12H2,1-4H3

InChI Key

BEECYWPPXWUPIT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Para-dioxane
Monosaccharide
Oxane
1,2-diol
Secondary alcohol
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aldehyde
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: HMDB0040390)

Source

Endogenous

Endogenous (HMDB: HMDB0040390)

Plant

Plant (HMDB: HMDB0040390)

Animal

Animal (HMDB: HMDB0040390)

Exogenous

Food

Food (HMDB: HMDB0040390)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0040390)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040390)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040390)

Lipid metabolism pathway (HMDB: HMDB0040390)

Cellular process

Cell signaling (HMDB: HMDB0040390)

Biochemical process

Lipid transport (HMDB: HMDB0040390)

Role

Biological role

Energy source (HMDB: HMDB0040390)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040390)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 - 127 °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	0.072 g/L	ALOGPS
logP	3.09	ALOGPS
logP	2.62	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	115.69 m³·mol⁻¹	ChemAxon
Polarizability	47.8 Å³	ChemAxon
Number of Rings	5	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]+	200.64	31661259
DarkChem	[M-H]-	192.41	31661259
DeepCCS	[M+H]+	204.243	30932474
DeepCCS	[M-H]-	201.885	30932474
DeepCCS	[M-2H]-	235.903	30932474
DeepCCS	[M+Na]+	211.131	30932474
AllCCS	[M+H]+	207.6	32859911
AllCCS	[M+H-H2O]+	205.6	32859911
AllCCS	[M+NH4]+	209.5	32859911
AllCCS	[M+Na]+	210.0	32859911
AllCCS	[M-H]-	201.7	32859911
AllCCS	[M+Na-2H]-	202.7	32859911
AllCCS	[M+HCOO]-	203.9	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. Predicted by Afia on May 17, 2022.	6.98 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7429 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.24 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2828.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	146.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	581.4 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	830.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1209.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	519.6 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	1617.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	480.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	449.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	243.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	372.9 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erinacine B	CC(C)C1=C2C3CC=C(C=O)C4OC5C(O)C(O)COC5OC4C3(C)CCC2(C)CC1	3695.0	Standard polar	33892256
Erinacine B	CC(C)C1=C2C3CC=C(C=O)C4OC5C(O)C(O)COC5OC4C3(C)CCC2(C)CC1	3242.0	Standard non polar	33892256
Erinacine B	CC(C)C1=C2C3CC=C(C=O)C4OC5C(O)C(O)COC5OC4C3(C)CCC2(C)CC1	3283.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erinacine B,1TMS,isomer #1	CC(C)C1=C2C3CC=C(C=O)C4OC5C(OCC(O)C5O[Si](C)(C)C)OC4C3(C)CCC2(C)CC1	3603.6	Semi standard non polar	33892256
Erinacine B,1TMS,isomer #2	CC(C)C1=C2C3CC=C(C=O)C4OC5C(OCC(O[Si](C)(C)C)C5O)OC4C3(C)CCC2(C)CC1	3611.0	Semi standard non polar	33892256
Erinacine B,2TMS,isomer #1	CC(C)C1=C2C3CC=C(C=O)C4OC5C(OCC(O[Si](C)(C)C)C5O[Si](C)(C)C)OC4C3(C)CCC2(C)CC1	3602.0	Semi standard non polar	33892256
Erinacine B,1TBDMS,isomer #1	CC(C)C1=C2C3CC=C(C=O)C4OC5C(OCC(O)C5O[Si](C)(C)C(C)(C)C)OC4C3(C)CCC2(C)CC1	3828.3	Semi standard non polar	33892256
Erinacine B,1TBDMS,isomer #2	CC(C)C1=C2C3CC=C(C=O)C4OC5C(OCC(O[Si](C)(C)C(C)(C)C)C5O)OC4C3(C)CCC2(C)CC1	3839.9	Semi standard non polar	33892256
Erinacine B,2TBDMS,isomer #1	CC(C)C1=C2C3CC=C(C=O)C4OC5C(OCC(O[Si](C)(C)C(C)(C)C)C5O[Si](C)(C)C(C)(C)C)OC4C3(C)CCC2(C)CC1	4037.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Erinacine B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gbi-4728900000-b2ef7b3bc025e679b4e4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinacine B GC-MS (2 TMS) - 70eV, Positive	splash10-03di-1643190000-cc8855206e9f3966c79d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinacine 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 - Erinacine B 10V, Positive-QTOF	splash10-00lr-0211900000-92fb92669d068bec956c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 20V, Positive-QTOF	splash10-00lr-2290300000-6e94e6bef381012c930a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 40V, Positive-QTOF	splash10-0pb9-9372000000-17fcdaed64e5531f5873	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 10V, Negative-QTOF	splash10-001i-0000900000-47f0d45d2026f88bca2f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 20V, Negative-QTOF	splash10-00lr-4920400000-e3a5e8b5c94b426fb67c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 40V, Negative-QTOF	splash10-000f-9100000000-2c03aeab457178753669	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 10V, Positive-QTOF	splash10-001i-0000900000-dda5185f54f69a4c1aa6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 20V, Positive-QTOF	splash10-001i-2248900000-838c4072231d6f97723a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 40V, Positive-QTOF	splash10-00du-9825000000-f833e5f8327c9a6f80ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 10V, Negative-QTOF	splash10-001i-0000900000-62fb2dfa255b71a0a07f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 20V, Negative-QTOF	splash10-001i-0003900000-034354e630463bf4f415	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinacine B 40V, Negative-QTOF	splash10-0kni-1069400000-c24a9a65adbaea0cbf87	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB020122

KNApSAcK ID

Not Available

Chemspider ID

7999882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9824135

PDB ID

Not Available

ChEBI ID

175500

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1883111

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 Erinacine B (HMDB0040390)

MOL for HMDB0040390 (Erinacine B)

3D MOL for HMDB0040390 (Erinacine B)

3D SDF for HMDB0040390 (Erinacine B)

3D-SDF for HMDB0040390 (Erinacine B)

PDB for HMDB0040390 (Erinacine B)

3D PDB for HMDB0040390 (Erinacine B)

SMILES for HMDB0040390 (Erinacine B)

INCHI for HMDB0040390 (Erinacine B)

Structure for HMDB0040390 (Erinacine B)

3D Structure for HMDB0040390 (Erinacine B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra