Hmdb loader

Showing metabocard for Lochnocarpol A (HMDB0302553)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 18:39:55 UTC
Update Date2021-09-23 18:39:55 UTC
HMDB IDHMDB0302553
Secondary Accession NumbersNone
Metabolite Identification
Common NameLochnocarpol A
DescriptionLochnocarpol a is a member of the class of compounds known as 8-prenylated flavanones. 8-prenylated flavanones are flavanones that features a C5-isoprenoid substituent at the 8-position. Lochnocarpol a is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Lochnocarpol a can be found in sweet orange, which makes lochnocarpol a a potential biomarker for the consumption of this food product.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0302553 (Lochnocarpol A)

6,8-Diprenylnaringenin
  Mrv1572001071617292D          

 30 32  0  0  1  0            999 V2000
    5.8309  -11.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -14.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676  -11.9832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8205  -14.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4082  -10.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1098  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -12.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -11.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851  -12.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240  -13.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449  -12.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5415  -13.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2624  -11.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -11.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697  -12.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2659  -11.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -10.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871  -12.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765  -10.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6906  -11.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -9.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429  -14.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 13  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  2  0  0  0  0
  5 24  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8 11  2  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 25  2  0  0  0  0
 21 26  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 26 30  1  0  0  0  0
M  END
Download

3D MOL for HMDB0302553 (Lochnocarpol A)

HMDB0302553
     RDKit          3D
Lochnocarpol A
 58 60  0  0  0  0  0  0  0  0999 V2000
   -5.5190   -1.1696    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0871   -2.0755   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6408   -3.4449   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -1.5999   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6642   -0.2414   -0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -0.1912   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200    1.0104   -0.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2364    2.1534   -1.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551    1.0746   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5762    2.3649   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3553    3.1563    0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1213    4.3822    0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829    5.0798   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044    5.0951    1.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5784   -0.0627   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955   -1.2648   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716   -1.3434   -0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124   -2.5328   -0.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109   -2.4410   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -3.3975    0.5296 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -2.5189   -0.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282   -1.1455   -0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560   -1.1889   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1970   -1.0820    1.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4323   -1.1206    1.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -1.2693    1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8453   -1.3089    1.8283 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4637   -1.3775   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144   -1.3375   -0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -0.0986   -0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0545   -1.7360    1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1216   -0.3742    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5947   -0.7809    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9900   -4.1546   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6499   -3.4956   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7011   -3.8588    0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177   -2.2796   -1.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122    0.2679   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748    0.3767   -0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236    2.1112   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    2.2012   -0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335    2.9147   -1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138    2.6696    1.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    6.1912   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143    4.7404   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    4.9872   -1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474    6.1834    1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    4.8053    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047    4.9047    2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900   -3.4394   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6624   -3.1320    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1620   -3.0999   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101   -0.9900   -1.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761   -0.9676    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5100   -1.0353    3.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2346   -2.1974    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3780   -1.4948   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1160   -1.4220   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 22 30  1  0
 17  6  1  0
 29 23  1  0
 30 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
M  END
Download

3D SDF for HMDB0302553 (Lochnocarpol A)

6,8-Diprenylnaringenin
  Mrv1572001071617292D          

 30 32  0  0  1  0            999 V2000
    5.8309  -11.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -14.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676  -11.9832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8205  -14.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4082  -10.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1098  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -12.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -11.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851  -12.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240  -13.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449  -12.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5415  -13.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2624  -11.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -11.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697  -12.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2659  -11.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -10.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871  -12.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765  -10.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6906  -11.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -9.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429  -14.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 13  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  2  0  0  0  0
  5 24  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8 11  2  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 25  2  0  0  0  0
 21 26  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 26 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302553

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=C(O)C=C2)C(CC=C(C)C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O5/c1-14(2)5-11-18-23(28)19(12-6-15(3)4)25-22(24(18)29)20(27)13-21(30-25)16-7-9-17(26)10-8-16/h5-10,21,26,28-29H,11-13H2,1-4H3

> <INCHI_KEY>
HCNLDGTUMBOHKT-UHFFFAOYSA-N

> <FORMULA>
C25H28O5

> <MOLECULAR_WEIGHT>
408.494

> <EXACT_MASS>
408.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.31907803086477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
6.292242049000001

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.070829382591645

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.508271233960288

> <JCHEM_PKA_STRONGEST_BASIC>
-4.961077727446398

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
119.7754

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0302553 (Lochnocarpol A)

HMDB0302553
     RDKit          3D
Lochnocarpol A
 58 60  0  0  0  0  0  0  0  0999 V2000
   -5.5190   -1.1696    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0871   -2.0755   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6408   -3.4449   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -1.5999   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6642   -0.2414   -0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -0.1912   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200    1.0104   -0.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2364    2.1534   -1.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551    1.0746   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5762    2.3649   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3553    3.1563    0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1213    4.3822    0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829    5.0798   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044    5.0951    1.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5784   -0.0627   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955   -1.2648   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716   -1.3434   -0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124   -2.5328   -0.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109   -2.4410   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -3.3975    0.5296 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -2.5189   -0.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282   -1.1455   -0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560   -1.1889   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1970   -1.0820    1.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4323   -1.1206    1.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -1.2693    1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8453   -1.3089    1.8283 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4637   -1.3775   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144   -1.3375   -0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -0.0986   -0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0545   -1.7360    1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1216   -0.3742    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5947   -0.7809    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9900   -4.1546   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6499   -3.4956   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7011   -3.8588    0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177   -2.2796   -1.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122    0.2679   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748    0.3767   -0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236    2.1112   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    2.2012   -0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335    2.9147   -1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138    2.6696    1.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    6.1912   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143    4.7404   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    4.9872   -1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474    6.1834    1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    4.8053    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047    4.9047    2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900   -3.4394   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6624   -3.1320    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1620   -3.0999   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101   -0.9900   -1.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761   -0.9676    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5100   -1.0353    3.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2346   -2.1974    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3780   -1.4948   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1160   -1.4220   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 22 30  1  0
 17  6  1  0
 29 23  1  0
 30 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
M  END
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PDB for HMDB0302553 (Lochnocarpol A)

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6,8-Diprenylnaringenin                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0      10.884 -22.375   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.218 -26.989   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.540 -22.369   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.865 -26.996   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      17.562 -20.087   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.538 -24.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.545 -23.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.218 -22.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.218 -25.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.879 -24.676   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.879 -23.138   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.871 -25.458   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.217 -23.144   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.211 -24.689   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.556 -22.388   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.218 -20.824   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.540 -25.451   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.877 -23.163   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.563 -20.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.545 -20.055   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.213 -24.676   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.216 -22.401   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.889 -20.081   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.222 -20.856   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.545 -18.523   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.880 -25.451   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.871 -17.754   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.218 -17.754   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.541 -24.676   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.880 -26.996   0.000  0.00  0.00           C+0
CONECT    1    7   13                                                       
CONECT    2    9                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   24                                                            
CONECT    6    7    9   12                                                  
CONECT    7    1    6    8                                                  
CONECT    8    7   11   16                                                  
CONECT    9    2    6   10                                                  
CONECT   10    9   11   17                                                  
CONECT   11    3    8   10                                                  
CONECT   12    4    6   14                                                  
CONECT   13    1   14   15                                                  
CONECT   14   12   13                                                       
CONECT   15   13   18   19                                                  
CONECT   16    8   20                                                       
CONECT   17   10   21                                                       
CONECT   18   15   22                                                       
CONECT   19   15   23                                                       
CONECT   20   16   25                                                       
CONECT   21   17   26                                                       
CONECT   22   18   24                                                       
CONECT   23   19   24                                                       
CONECT   24    5   22   23                                                  
CONECT   25   20   27   28                                                  
CONECT   26   21   29   30                                                  
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   26                                                            
CONECT   30   26                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END
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3D PDB for HMDB0302553 (Lochnocarpol A)

COMPND    HMDB0302553
HETATM    1  C1  UNL     1      -5.519  -1.170   0.939  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.087  -2.075  -0.155  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.641  -3.445  -0.209  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.206  -1.600  -1.050  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.664  -0.241  -0.987  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.204  -0.191  -0.795  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.520   1.010  -0.854  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.236   2.153  -1.104  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.155   1.075  -0.669  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.576   2.365  -0.738  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.355   3.156   0.495  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.121   4.382   0.532  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.483   5.080  -0.723  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.304   5.095   1.841  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.578  -0.063  -0.418  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.096  -1.265  -0.358  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.472  -1.343  -0.542  1.00  0.00           C  
HETATM   18  O2  UNL     1      -2.112  -2.533  -0.479  1.00  0.00           O  
HETATM   19  C17 UNL     1       0.711  -2.441  -0.086  1.00  0.00           C  
HETATM   20  O3  UNL     1       0.217  -3.398   0.530  1.00  0.00           O  
HETATM   21  C18 UNL     1       2.119  -2.519  -0.532  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.728  -1.146  -0.714  1.00  0.00           C  
HETATM   23  C20 UNL     1       4.056  -1.189  -0.037  1.00  0.00           C  
HETATM   24  C21 UNL     1       4.197  -1.082   1.332  1.00  0.00           C  
HETATM   25  C22 UNL     1       5.432  -1.121   1.948  1.00  0.00           C  
HETATM   26  C23 UNL     1       6.591  -1.269   1.214  1.00  0.00           C  
HETATM   27  O4  UNL     1       7.845  -1.309   1.828  1.00  0.00           O  
HETATM   28  C24 UNL     1       6.464  -1.378  -0.156  1.00  0.00           C  
HETATM   29  C25 UNL     1       5.214  -1.338  -0.769  1.00  0.00           C  
HETATM   30  O5  UNL     1       1.932  -0.099  -0.221  1.00  0.00           O  
HETATM   31  H1  UNL     1      -6.055  -1.736   1.728  1.00  0.00           H  
HETATM   32  H2  UNL     1      -6.122  -0.374   0.485  1.00  0.00           H  
HETATM   33  H3  UNL     1      -4.595  -0.781   1.432  1.00  0.00           H  
HETATM   34  H4  UNL     1      -4.990  -4.155  -0.751  1.00  0.00           H  
HETATM   35  H5  UNL     1      -6.650  -3.496  -0.658  1.00  0.00           H  
HETATM   36  H6  UNL     1      -5.701  -3.859   0.841  1.00  0.00           H  
HETATM   37  H7  UNL     1      -3.918  -2.280  -1.847  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.912   0.268  -1.949  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.175   0.377  -0.195  1.00  0.00           H  
HETATM   40  H10 UNL     1      -3.224   2.111  -1.237  1.00  0.00           H  
HETATM   41  H11 UNL     1       1.656   2.201  -0.879  1.00  0.00           H  
HETATM   42  H12 UNL     1       0.134   2.915  -1.601  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.614   2.670   1.451  1.00  0.00           H  
HETATM   44  H14 UNL     1      -0.596   6.191  -0.541  1.00  0.00           H  
HETATM   45  H15 UNL     1      -1.414   4.740  -1.187  1.00  0.00           H  
HETATM   46  H16 UNL     1       0.418   4.987  -1.391  1.00  0.00           H  
HETATM   47  H17 UNL     1      -0.347   6.183   1.674  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.282   4.805   2.306  1.00  0.00           H  
HETATM   49  H19 UNL     1       0.505   4.905   2.550  1.00  0.00           H  
HETATM   50  H20 UNL     1      -1.790  -3.439  -0.328  1.00  0.00           H  
HETATM   51  H21 UNL     1       2.662  -3.132   0.216  1.00  0.00           H  
HETATM   52  H22 UNL     1       2.162  -3.100  -1.483  1.00  0.00           H  
HETATM   53  H23 UNL     1       2.910  -0.990  -1.792  1.00  0.00           H  
HETATM   54  H24 UNL     1       3.276  -0.968   1.893  1.00  0.00           H  
HETATM   55  H25 UNL     1       5.510  -1.035   3.022  1.00  0.00           H  
HETATM   56  H26 UNL     1       8.235  -2.197   2.125  1.00  0.00           H  
HETATM   57  H27 UNL     1       7.378  -1.495  -0.730  1.00  0.00           H  
HETATM   58  H28 UNL     1       5.116  -1.422  -1.848  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4    4
CONECT    3   34   35   36
CONECT    4    5   37
CONECT    5    6   38   39
CONECT    6    7    7   17
CONECT    7    8    9
CONECT    8   40
CONECT    9   10   15   15
CONECT   10   11   41   42
CONECT   11   12   12   43
CONECT   12   13   14
CONECT   13   44   45   46
CONECT   14   47   48   49
CONECT   15   16   30
CONECT   16   17   17   19
CONECT   17   18
CONECT   18   50
CONECT   19   20   20   21
CONECT   21   22   51   52
CONECT   22   23   30   53
CONECT   23   24   24   29
CONECT   24   25   54
CONECT   25   26   26   55
CONECT   26   27   28
CONECT   27   56
CONECT   28   29   29   57
CONECT   29   58
END
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SMILES for HMDB0302553 (Lochnocarpol A)

CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=C(O)C=C2)C(CC=C(C)C)=C1O
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INCHI for HMDB0302553 (Lochnocarpol A)

InChI=1S/C25H28O5/c1-14(2)5-11-18-23(28)19(12-6-15(3)4)25-22(24(18)29)20(27)13-21(30-25)16-7-9-17(26)10-8-16/h5-10,21,26,28-29H,11-13H2,1-4H3
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC25H28O5
Average Molecular Weight408.494
Monoisotopic Molecular Weight408.193674002
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=C(O)C=C2)C(CC=C(C)C)=C1O
InChI Identifier
InChI=1S/C25H28O5/c1-14(2)5-11-18-23(28)19(12-6-15(3)4)25-22(24(18)29)20(27)13-21(30-25)16-7-9-17(26)10-8-16/h5-10,21,26,28-29H,11-13H2,1-4H3
InChI KeyHCNLDGTUMBOHKT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct Parent8-prenylated flavanones
Alternative Parents
Substituents
  • 6-prenylated flavanone
  • 8-prenylated flavanone
  • 6-prenylated flavan
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.5ALOGPS
logP6.29ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)7.51ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.78 m³·mol⁻¹ChemAxon
Polarizability45.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+202.98732859911
AllCCS[M+H-H2O]+200.3732859911
AllCCS[M+Na]+206.0932859911
AllCCS[M+NH4]+205.39932859911
AllCCS[M-H]-199.78332859911
AllCCS[M+Na-2H]-199.74932859911
AllCCS[M+HCOO]-199.88232859911
DeepCCS[M+H]+195.56430932474
DeepCCS[M-H]-193.20630932474
DeepCCS[M-2H]-227.3730932474
DeepCCS[M+Na]+202.51230932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 10V, Positive-QTOFsplash10-0a4i-0139800000-c9ce12fdf34261c436682016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 20V, Positive-QTOFsplash10-0q29-3589100000-9b6eded38b7299151a052016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 40V, Positive-QTOFsplash10-014j-3692000000-3a7fb7cd4beed515a9282016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 10V, Negative-QTOFsplash10-0a4i-0011900000-a13c9cd200ca414f2c522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 20V, Negative-QTOFsplash10-0a4i-2287900000-ad6da1b9389b1d6117572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 40V, Negative-QTOFsplash10-0006-3973000000-e644e3470d67e30440902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 10V, Positive-QTOFsplash10-0a4i-0000900000-dc5770577eafb47c94032021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 20V, Positive-QTOFsplash10-052s-0490600000-6a759f6cf5e4836d93ab2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 40V, Positive-QTOFsplash10-000i-0390000000-a16c74eb9577a155c8152021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 10V, Negative-QTOFsplash10-0a4i-0000900000-87c4cbcf84f61a9dd1332021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 20V, Negative-QTOFsplash10-0a4r-0090800000-aa0b7b2adc080864b8462021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lochnocarpol A 40V, Negative-QTOFsplash10-014i-0940000000-665e311c98b378d89d5b2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005123
KNApSAcK IDNot Available
Chemspider ID3814
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3951
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available