NP-MRD: Showing NP-Card for isoxanthohumol(sophora) (NP0316101)

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Record Information

Version

2.0

Created at

2022-09-11 15:04:27 UTC

Updated at

2022-09-11 15:04:27 UTC

NP-MRD ID

NP0316101

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isoxanthohumol(sophora)

Description

Isoxanthohumol 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. Thus, isoxanthohumol is considered to be a flavonoid lipid molecule. It is abbreviated as IX or IXN.8-Prenylnaringenin can be produced from isoxanthohumol by flora in the human intestine, and by fungi in cell cultures. Isoxanthohumol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isoxanthohumol is a prenylflavonoid, and it is a phytoestrogen. Isoxanthohumol is a bitter tasting compound. Outside of the human body, Isoxanthohumol is found, on average, in the highest concentration within beers. Isoxanthohumol has also been detected, but not quantified in, alcoholic beverages. This could make isoxanthohumol a potential biomarker for the consumption of these foods. It has limited estrogenic activity. Derivatives of isoxanthohumol are: 7,4′-Di-O-methylisoxanthohumol; 7-O-methylisoxanthohumol; 7-O-n-pentylisoxanthohumol; 7,4′-di-O-n-pentyl-8-isoxanthohumol; 7,4′-Di-O-allylisoxanthohumol; 7,4′-Di-O-acetylisoxanthohumol; and 7,4′-Di-O-palmitoylisoxanthohumol. isoxanthohumol(sophora) is found in Humulus lupulus and Sophora flavescens. At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.

Structure

MOL 3D MOL SDF PDB SMILES InChI

Isoxanthohumol
  Mrv1572001071617292D          

 26 28  0  0  0  0            999 V2000
    0.7145   -4.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.3962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.1587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  3 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
   -0.5826   -5.6458   -0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0854   -4.4568   -0.6777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4638   -3.2958   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8047   -3.1460    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -1.9289    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6274   -1.7531    0.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4528   -0.8535    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726    0.4408    1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0472    1.4636    0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1719    2.0292   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4736    1.7221    0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    3.0572   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.9961    0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876   -2.2125   -0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8208   -2.3164   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -3.1332   -1.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729   -1.4420    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2172   -0.1204    0.8723 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9318    1.0656    0.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    1.1114   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531    2.3232   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0956    3.5213   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6767    4.7409   -0.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500    3.4926    0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728    2.3039    0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8053    0.0118    0.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676   -6.3915   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -6.1354   -1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6774   -5.5541   -1.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198   -3.9288   -0.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3001   -2.4977    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9890    0.3278    1.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2781    0.8497    1.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0998    1.7113   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7386    0.6775    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2568    2.4429    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4511    1.7328    1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290    3.2953   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7201    2.5821   -2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211    3.9648   -1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7411   -1.4593   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742   -2.0542    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743   -0.0452    2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333    0.1906   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565    2.2900   -1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4231    5.1937   -1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5184    4.4617    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4708    2.3630    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 26  1  0
 26 13  1  0
 13  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  4  3  1  0
 25 19  1  0
 13 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  1
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
  6 31  1  0
  4 30  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
M  END

Isoxanthohumol
  Mrv1572001071617292D          

 26 28  0  0  0  0            999 V2000
    0.7145   -4.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.3962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.1587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  3 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316101

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)CC(OC2=C(CC=C(C)C)C(O)=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3

> <INCHI_KEY>
YKGCBLWILMDSAV-UHFFFAOYSA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.402

> <EXACT_MASS>
354.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
38.40126742507229

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
4.059569105666666

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.478487883256605

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.664454342976803

> <JCHEM_PKA_STRONGEST_BASIC>
-4.626074648338253

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
100.01489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoxanthohumol(sophora)

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Isoxanthohumol                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       1.334  -7.996   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -7.226   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -5.686   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -4.916   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -5.686   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -7.226   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -4.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -3.376   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -2.606   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -3.376   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -2.606   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -1.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.296   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   1.244   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   2.014   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   2.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -3.376   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -2.606   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -4.916   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -2.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -3.376   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -2.606   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -1.066   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003  -0.296   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  -0.296   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -1.066   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    3                                                       
CONECT   20    8   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
4',7-Dihydroxy-5-methoxy-8-prenylflavanone	HMDB
5-Methyl-8-prenylnaringenin	HMDB
7,4'-Dihydroxy-5-methoxy-8-prenylflavanone	HMDB
Isoxanthohumol	MeSH

Chemical Formula

C₂₁H₂₂O₅

Average Mass

354.4020 Da

Monoisotopic Mass

354.14672 Da

IUPAC Name

7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

isoxanthohumol(sophora)

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)CC(OC2=C(CC=C(C)C)C(O)=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3

InChI Key

YKGCBLWILMDSAV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Humulus lupulus	LOTUS Database	35616633
Sophora flavescens	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

8-prenylated flavanone
5-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Chromone
Chromane
1-benzopyran
Benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140553 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.25	ALOGPS
logP	4.06	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.01 m³·mol⁻¹	ChemAxon
Polarizability	38.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034048

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012290

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoxanthohumol

METLIN ID

Not Available

PubChem Compound

513197

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for isoxanthohumol(sophora) (NP0316101)

MOL for NP0316101 (isoxanthohumol(sophora))

3D MOL for NP0316101 (isoxanthohumol(sophora))

3D SDF for NP0316101 (isoxanthohumol(sophora))

3D-SDF for NP0316101 (isoxanthohumol(sophora))

PDB for NP0316101 (isoxanthohumol(sophora))

3D PDB for NP0316101 (isoxanthohumol(sophora))

SMILES for NP0316101 (isoxanthohumol(sophora))

INCHI for NP0316101 (isoxanthohumol(sophora))

Structure for NP0316101 (isoxanthohumol(sophora))

3D Structure for NP0316101 (isoxanthohumol(sophora))