NP-MRD: Showing NP-Card for Cannflavin B (NP0045200)

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Record Information

Version

2.0

Created at

2022-03-10 18:59:41 UTC

Updated at

2022-03-10 22:19:39 UTC

NP-MRD ID

NP0045200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannflavin B

Description

Cannflavin B belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that feature a C5-isoprenoid substituent at the 6-position. There are three known cannflavins including cannflavin A, B and C. Cannflavins are unique to Cannabis sativa (PMID: 3754224 ). Cannflavin B was identified in Cannabis in 1985 (PMID: 3859295 ; PMID: 3754224 ). Chemically, cannflavins are prenylflavonoids and are unrelated to THC and other cannabinoids. Cannflavin B is biosynthesized via the prenylation of chrysoeriol (PMID: 31151063 ). Specifically, an aromatic prenyltransferase (CsPT3) catalyzes the regiospecific addition of dimethylallyl diphosphate (DMAPP) to the methylated flavone, chrysoeriol to produce Cannflavin A. Chrysoeriol is produced through the conversion of luteolin via the O-methyltransferase (CsOMT21) (PMID: 31151063 ). Cannflavin B is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cannflavins exhibit anti-inflammatory activity that is thirty times that of aspirin (PMID: 31151063 ). It has been found that cannflavin B is an inhibitor of prostaglandin E2 production which appears to help explain its strong anti-inflammatory properties (PMID: 3859295 ; PMID: 3754224 ). Cannflavins were the first flavonoids identified to have direct inhibitory activity of two important pro-inflammatory mediators: Arachidonate 5-lipoxygenase (5-LOX) and prostaglandin E synthase (mPGES-1).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007382D          

 27 29  0  0  0  0            999 V2000
10000.7207 9997.4810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1463 9997.4810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.289710002.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.437710002.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.717310001.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2935 9998.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5791 9998.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8647 9998.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1503 9998.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8647 9997.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2935 9999.9641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7208 9999.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0062 9999.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0062 9998.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7207 9998.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1472 9999.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4327 9999.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4327 9998.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1472 9998.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8617 9998.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8617 9999.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.003510000.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.289110001.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.574510000.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5745 9999.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.2890 9999.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0036 9999.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  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  6  1  0  0  0  0
 13 11  1  0  0  0  0
  1 15  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  2  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 19  2  2  0  0  0  0
 17 12  2  0  0  0  0
 15 18  2  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 22  1  0  0  0  0
 22  5  1  0  0  0  0
 23  3  1  0  0  0  0
 21 25  1  0  0  0  0
M  END

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
    5.2480    3.3200    0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0178    2.3705   -0.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5202    1.1626   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067    0.7816   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154   -0.4230   -0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3119   -0.7661   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -1.9409   -0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -2.2784   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0573   -3.3484   -1.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3756   -1.3894   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009   -1.6332    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3376   -2.7719   -0.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -0.6918    0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924   -0.9977    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7578   -0.8494    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7784   -0.0250    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6329    0.1016   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0747    0.7632    1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435    0.4595    1.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125    1.4020    2.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380    0.7030    1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2291   -0.2228    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5128    0.0466    0.1294 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5871   -1.2367   -1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9226   -0.8629   -1.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3972    0.3396   -1.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7218    0.7309   -1.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7481    4.3200    0.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441    3.3440    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2554    3.0027    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    1.4425    0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175   -2.6776   -1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523   -3.5810   -0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2275   -0.3346    2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.0311    1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5431   -1.4228   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5635    0.6889   -0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1270    0.6242   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9590   -0.8846   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9986    1.3747    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2060    0.1164    2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2921    1.5032    1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1871    2.2645    2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0621    1.6081    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267   -2.1783   -1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5521   -1.5460   -2.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0276    1.6233   -0.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 26  2  0
 26 27  1  0
 26 25  1  0
 25 24  2  0
 24  5  1  0
  5  4  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 13 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
  4  3  1  0
 23  6  1  0
 22 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 47  1  0
 25 46  1  0
 24 45  1  0
  4 31  1  0
  7 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
M  END


  Mrv1652309272007382D          

 27 29  0  0  0  0            999 V2000
10000.7207 9997.4810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1463 9997.4810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.289710002.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.437710002.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.717310001.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2935 9998.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5791 9998.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8647 9998.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1503 9998.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8647 9997.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2935 9999.9641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7208 9999.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0062 9999.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0062 9998.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7207 9998.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1472 9999.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4327 9999.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4327 9998.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1472 9998.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8617 9998.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8617 9999.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.003510000.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.289110001.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.574510000.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5745 9999.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.2890 9999.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0036 9999.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  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  6  1  0  0  0  0
 13 11  1  0  0  0  0
  1 15  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  2  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 19  2  2  0  0  0  0
 17 12  2  0  0  0  0
 15 18  2  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 22  1  0  0  0  0
 22  5  1  0  0  0  0
 23  3  1  0  0  0  0
 21 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(CC=C(C)C)=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O6/c1-11(2)4-6-13-15(23)9-19-20(21(13)25)16(24)10-17(27-19)12-5-7-14(22)18(8-12)26-3/h4-5,7-10,22-23,25H,6H2,1-3H3

> <INCHI_KEY>
IXCUTZUASDSIJO-UHFFFAOYSA-N

> <FORMULA>
C21H20O6

> <MOLECULAR_WEIGHT>
368.385

> <EXACT_MASS>
368.125988364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
38.97142291056292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
4.277584867333333

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.9738845169447305

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.391196046815664

> <JCHEM_PKA_STRONGEST_BASIC>
-4.774154462018795

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
103.61989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cannflavin B

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0    8668.0128661.965   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8670.6738661.965   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8674.6748670.452   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8673.0848671.369   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8677.3398668.912   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8665.3488663.508   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.0148664.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.6818663.508   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3478664.280   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.6818661.968   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8665.3488666.600   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8668.0128666.596   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.6788665.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.6788664.286   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.0128663.516   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8670.6758666.596   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8669.3418665.826   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.3418664.286   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.6758663.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8672.0098664.286   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.0098665.826   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8676.0078668.141   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8674.6738668.911   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8673.3398668.141   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8673.3398666.601   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8674.6738665.831   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8676.0078666.601   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   19                                                            
CONECT    3    4   23                                                       
CONECT    4    3                                                            
CONECT    5   22                                                            
CONECT    6    7   14                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   13                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14   11                                                  
CONECT   14   13   15    6                                                  
CONECT   15   14    1   18                                                  
CONECT   16   17   21                                                       
CONECT   17   18   16   12                                                  
CONECT   18   17   19   15                                                  
CONECT   19   18   20    2                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   25                                                  
CONECT   22   23   27    5                                                  
CONECT   23   22   24    3                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   21                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Cannflavin	MeSH
Cannflavin a	MeSH
6-Prenylchrysoeriol	PhytoBank
Canniflavone	PhytoBank
Canniflavone 1	PhytoBank

Chemical Formula

C₂₁H₂₀O₆

Average Mass

368.3850 Da

Monoisotopic Mass

368.12599 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

cannflavin B

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(CC=C(C)C)=C(O)C=C2O1

InChI Identifier

InChI=1S/C21H20O6/c1-11(2)4-6-13-15(23)9-19-20(21(13)25)16(24)10-17(27-19)12-5-7-14(22)18(8-12)26-3/h4-5,7-10,22-23,25H,6H2,1-3H3

InChI Key

IXCUTZUASDSIJO-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cannabis indica	Plant	KNApSAcK
Cannabis sativa	NULL	Not Available
Dorstenia mannii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

6-prenylated flavones

Alternative Parents

Substituents

6-prenylated flavone
3p-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110795 )

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	3.77	ALOGPS
logP	4.28	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.39	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.62 m³·mol⁻¹	ChemAxon
Polarizability	38.97 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

403815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Barrett ML, Scutt AM, Evans FJ: Cannflavin A and B, prenylated flavones from Cannabis sativa L. Experientia. 1986 Apr 15;42(4):452-3. doi: 10.1007/BF02118655. [PubMed:3754224 ]
Barrett ML, Gordon D, Evans FJ: Isolation from Cannabis sativa L. of cannflavin--a novel inhibitor of prostaglandin production. Biochem Pharmacol. 1985 Jun 1;34(11):2019-24. doi: 10.1016/0006-2952(85)90325-9. [PubMed:3859295 ]
Rea KA, Casaretto JA, Al-Abdul-Wahid MS, Sukumaran A, Geddes-McAlister J, Rothstein SJ, Akhtar TA: Biosynthesis of cannflavins A and B from Cannabis sativa L. Phytochemistry. 2019 Aug;164:162-171. doi: 10.1016/j.phytochem.2019.05.009. Epub 2019 May 28. [PubMed:31151063 ]

Showing NP-Card for Cannflavin B (NP0045200)

MOL for NP0045200 (Cannflavin B)

3D MOL for NP0045200 (Cannflavin B)

3D SDF for NP0045200 (Cannflavin B)

3D-SDF for NP0045200 (Cannflavin B)

PDB for NP0045200 (Cannflavin B)

3D PDB for NP0045200 (Cannflavin B)

SMILES for NP0045200 (Cannflavin B)

INCHI for NP0045200 (Cannflavin B)

Structure for NP0045200 (Cannflavin B)

3D Structure for NP0045200 (Cannflavin B)