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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:07 UTC

HMDB ID

HMDB0000944

Secondary Accession Numbers

HMDB00944

Metabolite Identification

Common Name

Behenic acid

Description

Behenic acid, also docosanoic acid, is a normal carboxylic acid, a fatty acid with formula C21H43COOH. It is an important constituent of the behen oil extracted from the seeds of the Ben-oil tree, and it is so named from the Persian month Bahman when the roots of this tree were harvested. Behenic acid has been identified in the human placenta (PMID:32033212 ).

Structure

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

HMDB0000944
     RDKit          3D
Behenic acid
 68 67  0  0  0  0  0  0  0  0999 V2000
    8.9058   -1.7841   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1831   -0.7374   -1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7963   -0.4510   -1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7761    0.0525    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564    0.2671    0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985    0.7672    1.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979    1.0194    2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0172    2.0353    1.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461    1.9532    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359    0.7050    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4703    0.5734    1.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -0.6169    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.7384   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0003    0.4166   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.5841    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055   -0.5449    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8286   -0.9411   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6957    0.2057   -1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6543    0.6828   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172   -0.2351    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7329   -0.6707   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3288   -1.4215   -1.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5847   -2.4028   -1.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7998   -1.0243   -3.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2357   -2.4259   -0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4891   -2.4851   -1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6701   -1.2786   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0947   -1.0840   -2.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7418    0.2279   -1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3628    0.3388   -1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1390   -1.3521   -1.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1008   -0.6794    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2420    1.0482    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7581   -0.6938    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465    0.9768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8296    0.0621    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8516    1.7135    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1326    1.3591    3.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553    0.0369    2.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    2.2837    2.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    3.0195    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1512    2.1350   -0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    2.8497    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    0.7466   -0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523   -0.1404    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1853    1.4689    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    0.5185    2.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857   -1.5255    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741   -0.6991    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109   -0.7392   -1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -1.6685   -0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4907    0.1669   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4822    1.3661   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    0.9321    1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995    1.4588    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -1.4642    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7327   -0.2442    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -1.2342   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518   -1.7741   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2088   -0.1113   -2.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732    1.0867   -1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2066    1.5594   -0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1162    1.1930    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2987    0.3431    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3120   -1.1110    0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4863   -1.2899   -0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3706    0.2342   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6674   -0.0480   -3.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 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
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 24 68  1  0
M  END


  Mrv1652309272007272D          

 24 23  0  0  0  0            999 V2000
 9999.859110001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.574310001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.289210001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.004110001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.719810001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.433510001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.149310001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.862910001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.578710001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.294410001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.008110001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.723810001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.441610001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.155310001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.871010001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.144310001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.429310001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.714410001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.999310001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.284410001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.567410001.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.852510001.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.137610001.3806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.852510002.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  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
 10 11  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 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000944

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)

> <INCHI_KEY>
UKMSUNONTOPOIO-UHFFFAOYSA-N

> <FORMULA>
C22H44O2

> <MOLECULAR_WEIGHT>
340.5836

> <EXACT_MASS>
340.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.249826916801354

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
docosanoic acid

> <ALOGPS_LOGP>
9.19

> <JCHEM_LOGP>
8.923994767666667

> <ALOGPS_LOGS>
-7.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
104.68959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.04e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
behenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000944
     RDKit          3D
Behenic acid
 68 67  0  0  0  0  0  0  0  0999 V2000
    8.9058   -1.7841   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1831   -0.7374   -1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7963   -0.4510   -1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7761    0.0525    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564    0.2671    0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985    0.7672    1.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979    1.0194    2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0172    2.0353    1.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461    1.9532    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359    0.7050    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4703    0.5734    1.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -0.6169    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.7384   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0003    0.4166   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.5841    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055   -0.5449    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8286   -0.9411   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6957    0.2057   -1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6543    0.6828   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172   -0.2351    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7329   -0.6707   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3288   -1.4215   -1.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5847   -2.4028   -1.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7998   -1.0243   -3.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2357   -2.4259   -0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4891   -2.4851   -1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6701   -1.2786   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0947   -1.0840   -2.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7418    0.2279   -1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3628    0.3388   -1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1390   -1.3521   -1.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1008   -0.6794    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2420    1.0482    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7581   -0.6938    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465    0.9768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8296    0.0621    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8516    1.7135    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1326    1.3591    3.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553    0.0369    2.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    2.2837    2.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    3.0195    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1512    2.1350   -0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    2.8497    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    0.7466   -0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523   -0.1404    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1853    1.4689    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    0.5185    2.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857   -1.5255    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741   -0.6991    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109   -0.7392   -1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -1.6685   -0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4907    0.1669   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4822    1.3661   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    0.9321    1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995    1.4588    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -1.4642    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7327   -0.2442    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -1.2342   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518   -1.7741   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2088   -0.1113   -2.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732    1.0867   -1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2066    1.5594   -0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1162    1.1930    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2987    0.3431    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3120   -1.1110    0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4863   -1.2899   -0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3706    0.2342   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6674   -0.0480   -3.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 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
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 24 68  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.4048669.244   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.7398670.012   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.0738669.244   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8670.4088670.012   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8671.7448669.244   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8673.0768670.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8674.4128669.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.7448670.012   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8677.0808669.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8678.4168670.012   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8679.7488669.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8681.0848670.012   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8682.4248669.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8683.7578670.012   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8685.0938669.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.0698670.012   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.7358669.244   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.4008670.012   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8661.0658669.244   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8659.7318670.012   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8658.3928669.244   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8657.0588670.012   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8655.7238669.244   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8657.0588671.554   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    1   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0000944
HETATM    1  C1  UNL     1       8.906  -1.784  -1.055  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.183  -0.737  -1.854  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.796  -0.451  -1.337  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.776   0.052   0.079  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.256   0.267   0.393  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.199   0.767   1.774  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.898   1.019   2.424  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.017   2.035   1.872  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.446   1.953   0.519  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.636   0.705   0.236  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.470   0.573   1.171  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.388  -0.617   0.973  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.072  -0.738  -0.346  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.000   0.417  -0.643  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.074   0.584   0.368  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.006  -0.545   0.567  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.829  -0.941  -0.640  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.696   0.206  -1.113  1.00  0.00           C  
HETATM   19  C19 UNL     1      -6.654   0.683  -0.096  1.00  0.00           C  
HETATM   20  C20 UNL     1      -7.717  -0.235   0.378  1.00  0.00           C  
HETATM   21  C21 UNL     1      -8.733  -0.671  -0.615  1.00  0.00           C  
HETATM   22  C22 UNL     1      -8.329  -1.421  -1.779  1.00  0.00           C  
HETATM   23  O1  UNL     1      -7.585  -2.403  -1.732  1.00  0.00           O  
HETATM   24  O2  UNL     1      -8.800  -1.024  -3.048  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.236  -2.426  -0.442  1.00  0.00           H  
HETATM   26  H2  UNL     1       9.489  -2.485  -1.704  1.00  0.00           H  
HETATM   27  H3  UNL     1       9.670  -1.279  -0.430  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.095  -1.084  -2.896  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.742   0.228  -1.866  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.363   0.339  -1.985  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.139  -1.352  -1.394  1.00  0.00           H  
HETATM   32  H8  UNL     1       7.101  -0.679   0.828  1.00  0.00           H  
HETATM   33  H9  UNL     1       7.242   1.048   0.177  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.758  -0.694   0.207  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.947   0.977  -0.364  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.830   0.062   2.433  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.852   1.713   1.792  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.133   1.359   3.503  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.355   0.037   2.644  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.224   2.284   2.651  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.621   3.019   1.879  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.151   2.135  -0.272  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.719   2.850   0.448  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.301   0.747  -0.805  1.00  0.00           H  
HETATM   45  H21 UNL     1       2.352  -0.140   0.335  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.185   1.469   1.164  1.00  0.00           H  
HETATM   47  H23 UNL     1       0.886   0.518   2.210  1.00  0.00           H  
HETATM   48  H24 UNL     1       0.286  -1.525   1.055  1.00  0.00           H  
HETATM   49  H25 UNL     1      -1.074  -0.699   1.840  1.00  0.00           H  
HETATM   50  H26 UNL     1      -0.311  -0.739  -1.162  1.00  0.00           H  
HETATM   51  H27 UNL     1      -1.626  -1.669  -0.423  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.491   0.167  -1.618  1.00  0.00           H  
HETATM   53  H29 UNL     1      -1.482   1.366  -0.797  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.701   0.932   1.356  1.00  0.00           H  
HETATM   55  H31 UNL     1      -3.700   1.459   0.009  1.00  0.00           H  
HETATM   56  H32 UNL     1      -3.519  -1.464   0.938  1.00  0.00           H  
HETATM   57  H33 UNL     1      -4.733  -0.244   1.367  1.00  0.00           H  
HETATM   58  H34 UNL     1      -4.180  -1.234  -1.482  1.00  0.00           H  
HETATM   59  H35 UNL     1      -5.452  -1.774  -0.328  1.00  0.00           H  
HETATM   60  H36 UNL     1      -6.209  -0.111  -2.038  1.00  0.00           H  
HETATM   61  H37 UNL     1      -5.073   1.087  -1.422  1.00  0.00           H  
HETATM   62  H38 UNL     1      -7.207   1.559  -0.579  1.00  0.00           H  
HETATM   63  H39 UNL     1      -6.116   1.193   0.757  1.00  0.00           H  
HETATM   64  H40 UNL     1      -8.299   0.343   1.171  1.00  0.00           H  
HETATM   65  H41 UNL     1      -7.312  -1.111   0.938  1.00  0.00           H  
HETATM   66  H42 UNL     1      -9.486  -1.290  -0.019  1.00  0.00           H  
HETATM   67  H43 UNL     1      -9.371   0.234  -0.881  1.00  0.00           H  
HETATM   68  H44 UNL     1      -8.667  -0.048  -3.289  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7   36   37
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   42   43
CONECT   10   11   44   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18   58   59
CONECT   18   19   60   61
CONECT   19   20   62   63
CONECT   20   21   64   65
CONECT   21   22   66   67
CONECT   22   23   23   24
CONECT   24   68
END

HMDB0000944
     RDKit          3D
Behenic acid
 68 67  0  0  0  0  0  0  0  0999 V2000
    8.9058   -1.7841   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1831   -0.7374   -1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7963   -0.4510   -1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7761    0.0525    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564    0.2671    0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985    0.7672    1.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979    1.0194    2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0172    2.0353    1.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461    1.9532    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359    0.7050    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4703    0.5734    1.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -0.6169    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.7384   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0003    0.4166   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.5841    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055   -0.5449    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8286   -0.9411   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6957    0.2057   -1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6543    0.6828   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7172   -0.2351    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7329   -0.6707   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3288   -1.4215   -1.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5847   -2.4028   -1.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7998   -1.0243   -3.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2357   -2.4259   -0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4891   -2.4851   -1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6701   -1.2786   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0947   -1.0840   -2.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7418    0.2279   -1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3628    0.3388   -1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1390   -1.3521   -1.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1008   -0.6794    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2420    1.0482    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7581   -0.6938    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465    0.9768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8296    0.0621    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8516    1.7135    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1326    1.3591    3.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553    0.0369    2.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    2.2837    2.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    3.0195    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1512    2.1350   -0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    2.8497    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    0.7466   -0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523   -0.1404    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1853    1.4689    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    0.5185    2.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857   -1.5255    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741   -0.6991    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109   -0.7392   -1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -1.6685   -0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4907    0.1669   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4822    1.3661   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    0.9321    1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995    1.4588    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -1.4642    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7327   -0.2442    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -1.2342   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518   -1.7741   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2088   -0.1113   -2.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732    1.0867   -1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2066    1.5594   -0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1162    1.1930    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2987    0.3431    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3120   -1.1110    0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4863   -1.2899   -0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3706    0.2342   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6674   -0.0480   -3.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 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
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 24 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Docosanoic acid	ChEBI
Behensaeure	ChEBI
CH3-[CH2]20-COOH	ChEBI
Docosanic acid	ChEBI
Docosanoate	ChEBI
Docosansaeure	ChEBI
Docosoic acid	ChEBI
Dokosansaeure	ChEBI
N-Docosanoic acid	ChEBI
1-Docosanoate	Generator
Docosanate	Generator
Docosanoic acid	Generator
Docosoate	Generator
N-Docosanoate	Generator
Behenate	Generator
FA(22:0)	HMDB
Behenic acid	HMDB

Chemical Formula

C₂₂H₄₄O₂

Average Molecular Weight

340.5836

Monoisotopic Molecular Weight

340.334130652

IUPAC Name

docosanoic acid

Traditional Name

behenic acid

CAS Registry Number

112-85-6

SMILES

CCCCCCCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)

InChI Key

UKMSUNONTOPOIO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:28941 )
straight-chain saturated fatty acid (CHEBI:28941 )
Straight chain fatty acids (C08281 )
Saturated fatty acids (C08281 )
Straight chain fatty acids (LMFA01010022 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	81 °C	Not Available
Boiling Point	391.00 to 392.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.6e-05 mg/mL	Not Available
LogP	9.910	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	191.18	30932474
[M-H]-	Not Available	191.18	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000229

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.0e-05 g/L	ALOGPS
logP	9.19	ALOGPS
logP	8.92	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	104.69 m³·mol⁻¹	ChemAxon
Polarizability	47.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	192.047	31661259
DarkChem	[M-H]-	192.334	31661259
AllCCS	[M+H]+	202.645	32859911
AllCCS	[M-H]-	192.662	32859911
DeepCCS	[M+H]+	189.323	30932474
DeepCCS	[M-H]-	185.304	30932474
DeepCCS	[M-2H]-	222.135	30932474
DeepCCS	[M+Na]+	198.214	30932474
AllCCS	[M+H]+	202.6	32859911
AllCCS	[M+H-H2O]+	200.2	32859911
AllCCS	[M+NH4]+	204.9	32859911
AllCCS	[M+Na]+	205.6	32859911
AllCCS	[M-H]-	192.7	32859911
AllCCS	[M+Na-2H]-	194.5	32859911
AllCCS	[M+HCOO]-	196.7	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.	11.68 minutes	32390414
Predicted by Siyang on May 30, 2022	29.9066 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	47.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3698.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	878.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	329.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	457.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	697.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1259.5 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	1227.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2776.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	738.4 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	2352.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1052.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	636.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	957.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	729.5 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
Behenic acid	CCCCCCCCCCCCCCCCCCCCCC(O)=O	3629.9	Standard polar	33892256
Behenic acid	CCCCCCCCCCCCCCCCCCCCCC(O)=O	2505.1	Standard non polar	33892256
Behenic acid	CCCCCCCCCCCCCCCCCCCCCC(O)=O	2565.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Behenic acid,1TMS,isomer #1	CCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C	2639.3	Semi standard non polar	33892256
Behenic acid,1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2894.5	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.012 +/- 0.262 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.160 +/- 0.007 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	31.681 +/- 20.935 uM	Adult (>18 years old)	Female	Normal	9368807	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	23.277 +/- 0.913 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	26910390	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	61.661 +/- 2.281 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	26910390	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Obesity
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]

Associated OMIM IDs

114500 (Colorectal cancer)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Behenic acid

METLIN ID

260

PubChem Compound

8215

PDB ID

Not Available

ChEBI ID

28941

Food Biomarker Ontology

Not Available

VMH ID

DOCOSAC

MarkerDB ID

MDB00000288

Good Scents ID

rw1242111

References

Synthesis Reference

Lu, Jianmin; Li, He; Yang, Yiping; Du, Baoshan. Preparation of behenic acid from erucic acid by hydrogenation at ordinary pressure. Zhongguo Youzhi (1997), 22(5), 57-58.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. [PubMed:11124748 ]
Paik MJ, Kim KR, Yoon HR, Kim HJ: Diagnostic patterns of very-long-chain fatty acids in plasma of patients with X-linked adrenoleukodystrophy. J Chromatogr B Biomed Sci Appl. 2001 Aug 25;760(1):149-57. [PubMed:11522057 ]
Neuhouser ML, Patterson RE, King IB, Horner NK, Lampe JW: Selected nutritional biomarkers predict diet quality. Public Health Nutr. 2003 Oct;6(7):703-9. [PubMed:14552672 ]
Mosquera MM, de Ory F, Gallardo V, Cuenca L, Morales M, Sanchez-Yedra W, Cabezas T, Hernandez JM, Echevarria JE: Evaluation of diagnostic markers for measles virus infection in the context of an outbreak in Spain. J Clin Microbiol. 2005 Oct;43(10):5117-21. [PubMed:16207972 ]
Grosso NR, Nepote V, Guzman CA: Chemical composition of some wild peanut species (Arachis L.) seeds. J Agric Food Chem. 2000 Mar;48(3):806-9. [PubMed:10725154 ]
Peerapattana J, Otsuka K, Otsuka M: Time-controlled pulse-drug release from dry-coated wax matrix tablets for colon drug delivery. Biomed Mater Eng. 2004;14(3):293-301. [PubMed:15299241 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Behenic acid (HMDB0000944)

MOL for HMDB0000944 (Behenic acid)

3D MOL for HMDB0000944 (Behenic acid)

3D SDF for HMDB0000944 (Behenic acid)

3D-SDF for HMDB0000944 (Behenic acid)

PDB for HMDB0000944 (Behenic acid)

3D PDB for HMDB0000944 (Behenic acid)

SMILES for HMDB0000944 (Behenic acid)

INCHI for HMDB0000944 (Behenic acid)

Structure for HMDB0000944 (Behenic acid)

3D Structure for HMDB0000944 (Behenic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized