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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 16:57:44 UTC

Update Date

2021-09-22 16:57:45 UTC

HMDB ID

HMDB0301762

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cannithrene 2

Description

Cannithrene-2, is one of two isomers of cannithrene (the other being canninthrene-1). It belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivatives where at least one ring carbon-carbon double bond has been reduced via hydrogenation. Phenanthrenes are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzenes. Hydrophenanthrenes in Cannabis are structurally derived from stilbenoids, which have undergone an additional cyclazation reaction to yield the phenanthrene skeleton. Cannithrene 1 and 2 were the first two dihydrophenanthrenes isolated from Cannabis (PMID: 28799497 ). Cannithrene 2 is a hydrophobic, neutral compound that is insoluble in water. So far, no biological activity has been associated with cannithrene 2. Cannithrene 2 is one of the non-cannabinoid compounds that have been identified in cannabis plants (https://doi.org/10.1007/978-1-59259-947-9_2).

Structure

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

HMDB0301762
     RDKit          3D
Cannithrene 2
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.4076    1.5180   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350    0.2279    0.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    0.1283    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186    1.1953   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    1.0978   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    2.2472   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758   -0.1482    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5030   -1.2619    0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842   -1.1083    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -2.6115    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -2.8241   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -1.6677   -0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615   -1.8580   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.7789   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    0.5008   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314    1.6210   -0.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2204    1.6430   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405    0.6999   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2552    1.9945   -0.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755   -0.3635   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873    1.9486   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5094    1.4555   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060    2.0944    0.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958    2.1724   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0175    3.1366   -0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4851   -1.9804    0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -3.3244   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -2.8264    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2176   -3.1415   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8362   -3.7367    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065   -2.8860   -0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5749   -0.9178   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5798    2.6677    0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5768    1.3718   -1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5874    0.9205    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034    2.7942   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
  9  3  1  0
 20 12  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
M  END

  Mrv1652303202019002D          

 20 22  0  0  0  0            999 V2000
    2.2962    0.1205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6991   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991   -1.0069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991   -1.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -0.6845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    0.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263    1.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011    1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    1.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2487    1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2487    0.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9739    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9739   -0.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3292   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6040   -0.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011    0.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -1.2487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 15  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  2  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
 13 18  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301762

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1)C1=C(CC2)C=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-19-11-7-10-4-3-9-5-6-13(20-2)16(18)15(9)14(10)12(17)8-11/h5-8,17-18H,3-4H2,1-2H3

> <INCHI_KEY>
JOPGVVOTXYNMIS-UHFFFAOYSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.2958

> <EXACT_MASS>
272.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.92285126768126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethoxy-9,10-dihydrophenanthrene-4,5-diol

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
3.2611148793333333

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.990595415752967

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.92105505912575

> <JCHEM_PKA_STRONGEST_BASIC>
-4.560352643183182

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
76.36259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethoxy-9,10-dihydrophenanthrene-4,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301762
     RDKit          3D
Cannithrene 2
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.4076    1.5180   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350    0.2279    0.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    0.1283    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186    1.1953   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    1.0978   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    2.2472   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758   -0.1482    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5030   -1.2619    0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842   -1.1083    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -2.6115    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -2.8241   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -1.6677   -0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615   -1.8580   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.7789   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    0.5008   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314    1.6210   -0.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2204    1.6430   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405    0.6999   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2552    1.9945   -0.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755   -0.3635   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873    1.9486   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5094    1.4555   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060    2.0944    0.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958    2.1724   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0175    3.1366   -0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4851   -1.9804    0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -3.3244   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -2.8264    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2176   -3.1415   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8362   -3.7367    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065   -2.8860   -0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5749   -0.9178   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5798    2.6677    0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5768    1.3718   -1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5874    0.9205    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034    2.7942   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
  9  3  1  0
 20 12  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0       4.286   0.225   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.038  -1.127   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.038  -1.880   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -5.038  -3.384   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.030  -1.278   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.729   0.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.933   0.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.933   2.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.729   3.384   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.375   2.481   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.977   3.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.331   2.481   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.331   0.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.685   0.225   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.685  -1.278   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.481  -2.030   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.127  -1.278   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.977   0.225   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.375   0.977   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.074  -2.331   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1                                                            
CONECT    3    4   15                                                       
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7   19                                                  
CONECT    7    1    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15    3   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   13   17   19                                                  
CONECT   19    6   10   18                                                  
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0301762
HETATM    1  C1  UNL     1       5.408   1.518  -0.080  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.835   0.228   0.066  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.441   0.128   0.060  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.619   1.195  -0.076  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.227   1.098  -0.083  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.557   2.247  -0.233  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.676  -0.148   0.058  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.503  -1.262   0.203  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.884  -1.108   0.200  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.939  -2.612   0.445  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.391  -2.824  -0.166  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.294  -1.668  -0.075  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.662  -1.858  -0.069  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.502  -0.779  -0.064  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.038   0.501  -0.063  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.831   1.621  -0.059  1.00  0.00           O  
HETATM   17  C14 UNL     1      -5.220   1.643  -0.056  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.641   0.700  -0.067  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.255   1.994  -0.059  1.00  0.00           O  
HETATM   20  C16 UNL     1      -0.776  -0.363  -0.072  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.987   1.949  -1.011  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.509   1.456  -0.080  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.106   2.094   0.822  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.096   2.172  -0.185  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.018   3.137  -0.339  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.485  -1.980   0.310  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.667  -3.324  -0.028  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.935  -2.826   1.552  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.218  -3.142  -1.228  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.836  -3.737   0.316  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.007  -2.886  -0.069  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.575  -0.918  -0.060  1.00  0.00           H  
HETATM   33  H13 UNL     1      -5.580   2.668   0.155  1.00  0.00           H  
HETATM   34  H14 UNL     1      -5.577   1.372  -1.068  1.00  0.00           H  
HETATM   35  H15 UNL     1      -5.587   0.921   0.702  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.903   2.794  -0.045  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   24
CONECT    5    6    7    7
CONECT    6   25
CONECT    7    8   20
CONECT    8    9    9   10
CONECT    9   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   13   20
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   18
CONECT   16   17
CONECT   17   33   34   35
CONECT   18   19   20   20
CONECT   19   36
END

HMDB0301762
     RDKit          3D
Cannithrene 2
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.4076    1.5180   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350    0.2279    0.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    0.1283    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186    1.1953   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    1.0978   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    2.2472   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758   -0.1482    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5030   -1.2619    0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842   -1.1083    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -2.6115    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -2.8241   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -1.6677   -0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615   -1.8580   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.7789   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    0.5008   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314    1.6210   -0.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2204    1.6430   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405    0.6999   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2552    1.9945   -0.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755   -0.3635   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873    1.9486   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5094    1.4555   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060    2.0944    0.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958    2.1724   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0175    3.1366   -0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4851   -1.9804    0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -3.3244   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -2.8264    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2176   -3.1415   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8362   -3.7367    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065   -2.8860   -0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5749   -0.9178   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5798    2.6677    0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5768    1.3718   -1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5874    0.9205    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034    2.7942   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
  9  3  1  0
 20 12  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₄

Average Molecular Weight

272.2958

Monoisotopic Molecular Weight

272.104859

IUPAC Name

2,6-dimethoxy-9,10-dihydrophenanthrene-4,5-diol

Traditional Name

2,6-dimethoxy-9,10-dihydrophenanthrene-4,5-diol

CAS Registry Number

83016-16-4

SMILES

COC1=CC2=C(C(O)=C1)C1=C(CC2)C=CC(OC)=C1O

InChI Identifier

InChI=1S/C16H16O4/c1-19-11-7-10-4-3-9-5-6-13(20-2)16(18)15(9)14(10)12(17)8-11/h5-8,17-18H,3-4H2,1-2H3

InChI Key

JOPGVVOTXYNMIS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Hydrophenanthrenes

Direct Parent

Hydrophenanthrenes

Alternative Parents

Substituents

Hydrophenanthrene
1-naphthol
Naphthalene
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0301762)

Food

Fruit

Berry

Black crowberry (FooDB: FOOD00075)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.85	ALOGPS
logP	3.26	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.36 m³·mol⁻¹	ChemAxon
Polarizability	28.92 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	163.319	32859911
AllCCS	[M+H-H2O]+	159.645	32859911
AllCCS	[M+Na]+	167.712	32859911
AllCCS	[M+NH4]+	166.731	32859911
AllCCS	[M-H]-	167.757	32859911
AllCCS	[M+Na-2H]-	167.279	32859911
AllCCS	[M+HCOO]-	166.878	32859911
DeepCCS	[M+H]+	161.181	30932474
DeepCCS	[M-H]-	158.823	30932474
DeepCCS	[M-2H]-	192.009	30932474
DeepCCS	[M+Na]+	167.275	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cannithrene 2 GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cannithrene 2 GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cannithrene 2 GC-MS (2 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 10V, Positive-QTOF	splash10-00di-0090000000-ef7de4d391b99f8c46fd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 20V, Positive-QTOF	splash10-00di-0490000000-ed988b16accc0f1ee470	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 40V, Positive-QTOF	splash10-02bb-1790000000-f1739a582e42c99b9019	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 10V, Negative-QTOF	splash10-00di-0090000000-867f6aee25acb934d031	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 20V, Negative-QTOF	splash10-00di-0090000000-76d4a75df389853757fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 40V, Negative-QTOF	splash10-056s-0390000000-4671bc90fb2391019707	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 10V, Positive-QTOF	splash10-00di-0090000000-be7a06d3a99be6265fa3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 20V, Positive-QTOF	splash10-00di-0090000000-72172f717bb9877b0ae3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 40V, Positive-QTOF	splash10-000i-0940000000-8cbaa447eb4dd1f76dac	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 10V, Negative-QTOF	splash10-00di-0090000000-fa0ebf6f807322562116	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 20V, Negative-QTOF	splash10-00di-0090000000-c19ecb967c82c4f23467	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannithrene 2 40V, Negative-QTOF	splash10-000i-0090000000-489a7d3a39991252ab2f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000638

KNApSAcK ID

C00015535

Chemspider ID

59696648

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86021565

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. [PubMed:28799497 ]

Showing metabocard for Cannithrene 2 (HMDB0301762)

MOL for HMDB0301762 (Cannithrene 2)

3D MOL for HMDB0301762 (Cannithrene 2)

3D SDF for HMDB0301762 (Cannithrene 2)

3D-SDF for HMDB0301762 (Cannithrene 2)

PDB for HMDB0301762 (Cannithrene 2)

3D PDB for HMDB0301762 (Cannithrene 2)

SMILES for HMDB0301762 (Cannithrene 2)

INCHI for HMDB0301762 (Cannithrene 2)

Structure for HMDB0301762 (Cannithrene 2)

3D Structure for HMDB0301762 (Cannithrene 2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra