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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:53:49 UTC

Update Date

2022-03-07 02:55:02 UTC

HMDB ID

HMDB0036727

Secondary Accession Numbers

HMDB36727

Metabolite Identification

Common Name

Candol B

Description

Candol B, also known as 4beta-kaur-16-en-19-ol, belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by the cyclization of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Candol B is an extremely weak basic (essentially neutral) compound (based on its pKa). Candol B is found in cereals and cereal products. Candol B is a constituent of barley.

Structure

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

HMDB0036727
     RDKit          3D
Candol B
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.8656    1.4189   -1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    0.8274   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913    1.1486   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    0.6160    0.1398 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7190    1.7071    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    1.7410    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    0.4306   -0.1536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7477    0.3945    0.2380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0163    0.8013    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4002    1.4876   -0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2029    1.1676   -1.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -0.8838   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -2.1047   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671   -1.9475   -0.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -0.7787    0.2839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5856   -1.0999    1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532   -0.6128   -0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7276   -1.8228   -0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457   -1.5232   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094   -0.3187    0.2286 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6133    0.1884    1.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7897    2.2567   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8676    1.1291   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067    2.2262   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    0.6234   -1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2165    2.6879    0.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430    1.7269    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987    2.2867    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104    2.4348   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109    0.3404   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6561    1.7091    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453   -0.0248    2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1191    0.9945    2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8456    2.4171   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4806    1.5684   -0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    1.8914   -2.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2782   -1.0136    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631   -0.8082   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0342   -2.8431   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7131   -2.6582    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334   -2.8706   -0.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -1.8311   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -2.0732    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -1.3340    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -0.3959    2.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -0.5201   -1.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3639   -2.5966   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -2.2822    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663   -2.3958   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2603   -1.4503   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6435   -0.5318    0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2497   -0.5844    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    1.0845    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 17  4  1  0
 21  4  1  0
 15  7  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  6
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  1
 21 52  1  0
 21 53  1  0
M  END


  Mrv1652304302019202D          

 23 26  0  0  0  0            999 V2000
 9993.7632 9995.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0506 9993.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3361 9993.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3361 9992.6053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4757 9994.6792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7632 9993.4324    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7615 9995.0857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.7615 9994.2605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9994.4761 9993.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1906 9994.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0507 9995.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3362 9995.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3362 9994.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0507 9993.8482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.2720 9996.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3667 9996.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9364 9996.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4773 9995.5112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.7577 9996.8504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.9572 9995.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2120 9996.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1852 9995.0883    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.0291 9996.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  6  0  0  0
 14  8  1  0  0  0  0
  8  6  1  1  0  0  0
 11  7  1  0  0  0  0
  7  1  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 15  1  6  0  0  0
 19 15  1  6  0  0  0
 21 23  2  0  0  0  0
 18  7  1  0  0  0  0
 18  5  1  1  0  0  0
 10 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036727

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CO)CCC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O/c1-14-11-20-10-7-16-18(2,13-21)8-4-9-19(16,3)17(20)6-5-15(14)12-20/h15-17,21H,1,4-13H2,2-3H3/t15-,16-,17+,18-,19-,20-/m1/s1

> <INCHI_KEY>
TUJQVRFWMWRMIO-DAUOMPHXSA-N

> <FORMULA>
C20H32O

> <MOLECULAR_WEIGHT>
288.475

> <EXACT_MASS>
288.24531565

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.472277681656394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
4.335367008666668

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.592349954751715

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2275061297915997

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
87.4211

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036727
     RDKit          3D
Candol B
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.8656    1.4189   -1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    0.8274   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913    1.1486   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    0.6160    0.1398 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7190    1.7071    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    1.7410    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    0.4306   -0.1536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7477    0.3945    0.2380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0163    0.8013    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4002    1.4876   -0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2029    1.1676   -1.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -0.8838   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -2.1047   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671   -1.9475   -0.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -0.7787    0.2839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5856   -1.0999    1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532   -0.6128   -0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7276   -1.8228   -0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457   -1.5232   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094   -0.3187    0.2286 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6133    0.1884    1.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7897    2.2567   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8676    1.1291   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067    2.2262   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    0.6234   -1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2165    2.6879    0.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430    1.7269    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987    2.2867    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104    2.4348   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109    0.3404   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6561    1.7091    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453   -0.0248    2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1191    0.9945    2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8456    2.4171   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4806    1.5684   -0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    1.8914   -2.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2782   -1.0136    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631   -0.8082   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0342   -2.8431   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7131   -2.6582    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334   -2.8706   -0.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -1.8311   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -2.0732    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -1.3340    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -0.3959    2.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -0.5201   -1.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3639   -2.5966   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -2.2822    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663   -2.3958   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2603   -1.4503   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6435   -0.5318    0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2497   -0.5844    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    1.0845    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 17  4  1  0
 21  4  1  0
 15  7  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  6
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  1
 21 52  1  0
 21 53  1  0
M  END

HEADER    PROTEIN                                 30-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-20         0                                  
HETATM    1  C   UNK     0    8655.0258659.040   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8653.6948653.631   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8652.3618654.403   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8652.3618652.863   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8656.3558656.734   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8655.0258654.407   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8655.0228657.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8655.0228655.953   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8656.3558655.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8657.6898655.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8653.6958658.263   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8652.3618657.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8652.3618655.953   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8653.6958655.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8657.8418659.271   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8656.1518659.813   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8657.2158660.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8656.3588658.288   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.7488660.787   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8659.1208658.039   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8659.5968659.503   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8657.6798657.498   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8661.1218659.710   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    4   14                                                       
CONECT    3   14                                                            
CONECT    4    2                                                            
CONECT    5   18                                                            
CONECT    6    8                                                            
CONECT    7    8   11    1   18                                             
CONECT    8    7    9   14    6                                             
CONECT    9    8   10                                                       
CONECT   10    9   22                                                       
CONECT   11   12    7                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    2    3    8                                             
CONECT   15   22   19                                                       
CONECT   16   17   18                                                       
CONECT   17   16   19                                                       
CONECT   18   16   22    7    5                                             
CONECT   19   17   21   15                                                  
CONECT   20   21   22                                                       
CONECT   21   19   20   23                                                  
CONECT   22   18   20   15   10                                             
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0036727
HETATM    1  C1  UNL     1       4.866   1.419  -1.104  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.781   0.827  -0.694  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.391   1.149  -1.043  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.568   0.616   0.140  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.719   1.707   0.669  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.681   1.741   0.161  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.291   0.431  -0.154  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.748   0.394   0.238  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.016   0.801   1.656  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.400   1.488  -0.626  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.203   1.168  -1.977  1.00  0.00           O  
HETATM   12  C11 UNL     1      -3.431  -0.884  -0.148  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.610  -2.105  -0.115  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.167  -1.947  -0.479  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.522  -0.779   0.284  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.586  -1.100   1.715  1.00  0.00           C  
HETATM   17  C16 UNL     1       0.853  -0.613  -0.295  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.728  -1.823  -0.121  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.146  -1.523  -0.485  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.709  -0.319   0.229  1.00  0.00           C  
HETATM   21  C20 UNL     1       2.613   0.188   1.178  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.790   2.257  -1.786  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.868   1.129  -0.805  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.207   2.226  -1.200  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.089   0.623  -1.979  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.216   2.688   0.399  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.743   1.727   1.797  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.299   2.287   0.924  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.710   2.435  -0.733  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.311   0.340  -1.287  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.656   1.709   1.760  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.645  -0.025   2.104  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.119   0.994   2.262  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.846   2.417  -0.435  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.481   1.568  -0.416  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.749   1.891  -2.471  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.278  -1.014   0.591  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.963  -0.808  -1.139  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.034  -2.843  -0.861  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.713  -2.658   0.865  1.00  0.00           H  
HETATM   41  H20 UNL     1      -0.633  -2.871  -0.146  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.995  -1.831  -1.547  1.00  0.00           H  
HETATM   43  H22 UNL     1      -0.043  -2.073   1.874  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.638  -1.334   1.981  1.00  0.00           H  
HETATM   45  H24 UNL     1      -0.170  -0.396   2.424  1.00  0.00           H  
HETATM   46  H25 UNL     1       0.692  -0.520  -1.413  1.00  0.00           H  
HETATM   47  H26 UNL     1       1.364  -2.597  -0.850  1.00  0.00           H  
HETATM   48  H27 UNL     1       1.706  -2.282   0.859  1.00  0.00           H  
HETATM   49  H28 UNL     1       3.766  -2.396  -0.172  1.00  0.00           H  
HETATM   50  H29 UNL     1       3.260  -1.450  -1.588  1.00  0.00           H  
HETATM   51  H30 UNL     1       4.643  -0.532   0.763  1.00  0.00           H  
HETATM   52  H31 UNL     1       2.250  -0.584   1.849  1.00  0.00           H  
HETATM   53  H32 UNL     1       2.969   1.084   1.727  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   20
CONECT    3    4   24   25
CONECT    4    5   17   21
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   15   30
CONECT    8    9   10   12
CONECT    9   31   32   33
CONECT   10   11   34   35
CONECT   11   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   17
CONECT   16   43   44   45
CONECT   17   18   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   51
CONECT   21   52   53
END

HMDB0036727
     RDKit          3D
Candol B
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.8656    1.4189   -1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    0.8274   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913    1.1486   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    0.6160    0.1398 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7190    1.7071    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    1.7410    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    0.4306   -0.1536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7477    0.3945    0.2380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0163    0.8013    1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4002    1.4876   -0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2029    1.1676   -1.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -0.8838   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -2.1047   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671   -1.9475   -0.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -0.7787    0.2839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5856   -1.0999    1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532   -0.6128   -0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7276   -1.8228   -0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457   -1.5232   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094   -0.3187    0.2286 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6133    0.1884    1.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7897    2.2567   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8676    1.1291   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067    2.2262   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    0.6234   -1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2165    2.6879    0.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430    1.7269    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987    2.2867    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104    2.4348   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109    0.3404   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6561    1.7091    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453   -0.0248    2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1191    0.9945    2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8456    2.4171   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4806    1.5684   -0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    1.8914   -2.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2782   -1.0136    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631   -0.8082   -1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0342   -2.8431   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7131   -2.6582    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334   -2.8706   -0.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -1.8311   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -2.0732    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -1.3340    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -0.3959    2.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -0.5201   -1.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3639   -2.5966   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -2.2822    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663   -2.3958   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2603   -1.4503   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6435   -0.5318    0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2497   -0.5844    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    1.0845    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 17  4  1  0
 21  4  1  0
 15  7  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  6
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  1
 21 52  1  0
 21 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Kaur-16-en-19-ol	HMDB
(4beta)-Kaur-16-en-18-ol	HMDB
(4Β)-kaur-16-en-18-ol	HMDB
16-Kauren-18-ol	HMDB
4beta-Kaur-16-en-19-ol	HMDB
4Β-kaur-16-en-19-ol	HMDB
ent-18-Hydroxykaur-16-ene	HMDB
Kaur-16-en-19-ol	HMDB
ent-Kaur-16-en-19-ol	HMDB
Candol B	HMDB

Chemical Formula

C₂₀H₃₂O

Average Molecular Weight

288.475

Monoisotopic Molecular Weight

288.24531565

IUPAC Name

[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

Traditional Name

[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

CAS Registry Number

17360-30-4

SMILES

[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CO)CCC[C@@]21C

InChI Identifier

InChI=1S/C20H32O/c1-14-11-20-10-7-16-18(2,13-21)8-4-9-19(16,3)17(20)6-5-15(14)12-20/h15-17,21H,1,4-13H2,2-3H3/t15-,16-,17+,18-,19-,20-/m1/s1

InChI Key

TUJQVRFWMWRMIO-DAUOMPHXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036727)
Cell membrane (HMDB: HMDB0036727)

Cellular substructure

Extracellular (HMDB: HMDB0036727)
Membrane (HMDB: HMDB0036727)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036727)

Source

Endogenous

Endogenous (HMDB: HMDB0036727)

Plant

Poaceae (HMDB: HMDB0036727)

Animal

Animal (HMDB: HMDB0036727)

Exogenous

Food

Food (HMDB: HMDB0036727)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036727)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036727)

Cellular process

Cell signaling (HMDB: HMDB0036727)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036727)

Metabolic pathway

Gibberellin A12 Biosynthesis (PathBank: SMP0012068)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036727)

Nutrient

Nutrient (HMDB: HMDB0036727)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036727)

Emulsifier (HMDB: HMDB0036727)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 - 142 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.21 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00036 g/L	ALOGPS
logP	3.98	ALOGPS
logP	4.34	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.42 m³·mol⁻¹	ChemAxon
Polarizability	35.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	207.254	30932474
DeepCCS	[M+Na]+	182.107	30932474
AllCCS	[M+H]+	174.9	32859911
AllCCS	[M+H-H2O]+	171.9	32859911
AllCCS	[M+NH4]+	177.7	32859911
AllCCS	[M+Na]+	178.6	32859911
AllCCS	[M-H]-	180.3	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	181.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Candol B	[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CO)CCC[C@@]21C	2764.5	Standard polar	33892256
Candol B	[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CO)CCC[C@@]21C	2290.0	Standard non polar	33892256
Candol B	[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CO)CCC[C@@]21C	2358.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Candol B,1TMS,isomer #1	C=C1C[C@@]23CC[C@@H]4[C@@](C)(CO[Si](C)(C)C)CCC[C@@]4(C)[C@@H]2CC[C@@H]1C3	2282.1	Semi standard non polar	33892256
Candol B,1TBDMS,isomer #1	C=C1C[C@@]23CC[C@@H]4[C@@](C)(CO[Si](C)(C)C(C)(C)C)CCC[C@@]4(C)[C@@H]2CC[C@@H]1C3	2572.4	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 - Candol 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 - Candol B 10V, Positive-QTOF	splash10-059i-0090000000-67608884017b70ce7f81	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candol B 20V, Positive-QTOF	splash10-00ds-1980000000-dc26c9f65f23b21de5b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candol B 40V, Positive-QTOF	splash10-000y-9850000000-b945ebbce2700294735f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candol B 10V, Negative-QTOF	splash10-000i-0090000000-81ee7157e3dd1ba9c37b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candol B 20V, Negative-QTOF	splash10-000i-0090000000-81ee7157e3dd1ba9c37b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candol B 40V, Negative-QTOF	splash10-000i-0090000000-7281a230011f1d1ab4d8	2021-09-24	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

FDB015700

KNApSAcK ID

C00031762

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101289732

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856991

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 Candol B (HMDB0036727)

MOL for HMDB0036727 (Candol B)

3D MOL for HMDB0036727 (Candol B)

3D SDF for HMDB0036727 (Candol B)

3D-SDF for HMDB0036727 (Candol B)

PDB for HMDB0036727 (Candol B)

3D PDB for HMDB0036727 (Candol B)

SMILES for HMDB0036727 (Candol B)

INCHI for HMDB0036727 (Candol B)

Structure for HMDB0036727 (Candol B)

3D Structure for HMDB0036727 (Candol B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra