NP-MRD: Showing NP-Card for 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (NP0037649)

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Record Information

Version

2.0

Created at

2021-06-20 20:31:32 UTC

Updated at

2021-06-30 00:09:58 UTC

NP-MRD ID

NP0037649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,7-dimethoxy-1,2,5-trihydroxyphenanthrene

Provided By

JEOL Database JEOL Logo

Description

4,7-Dimethoxyphenanthrene-1,2,5-triol belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene is found in Cannabis sativa variety. 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene was first documented in 2008 (Radwan, M. M., et al.). Based on a literature review very few articles have been published on 4,7-dimethoxyphenanthrene-1,2,5-triol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122313D          

 35 37  0  0  0  0            999 V2000
    3.6128    0.3939   -2.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.1385   -2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916    0.2657   -1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.6495   -0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    0.7362    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6491    1.2377    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    0.4087    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    0.0841   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.1519   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -0.0665   -1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103    0.1969    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    0.2583    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9299    0.0998    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7898    0.4795    2.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0199    0.5411    2.9239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    0.6024    3.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    0.5150    2.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    0.5621    3.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -0.7643    3.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.3876    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    0.0011   -2.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.3004   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268    1.4345   -1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2874    0.2311   -2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4063    0.9129    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    1.3774    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -0.3843   -2.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728   -0.2291   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6140    0.1945    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963    0.7349    3.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297    0.7437    4.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -0.6994    4.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -1.1690    4.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -1.4345    2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1017   -0.2697   -3.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
 20 11  2  0  0  0  0
  8 21  1  0  0  0  0
 20 17  1  0  0  0  0
 21  3  2  0  0  0  0
 12 11  1  0  0  0  0
  3  4  1  0  0  0  0
 17 16  2  0  0  0  0
  4  5  2  0  0  0  0
  5  7  1  0  0  0  0
 14 15  1  0  0  0  0
 20  7  1  0  0  0  0
 17 18  1  0  0  0  0
 11 10  1  0  0  0  0
  3  2  1  0  0  0  0
 10  9  2  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
 12 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18 19  1  0  0  0  0
 14 12  2  0  0  0  0
  5  6  1  0  0  0  0
 16 31  1  0  0  0  0
 10 28  1  0  0  0  0
  9 27  1  0  0  0  0
 21 35  1  0  0  0  0
  4 25  1  0  0  0  0
 15 30  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
 13 29  1  0  0  0  0
 19 32  1  0  0  0  0
 19 33  1  0  0  0  0
 19 34  1  0  0  0  0
  6 26  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    3.6128    0.3939   -2.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.1385   -2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916    0.2657   -1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.6495   -0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    0.7362    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6491    1.2377    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    0.4087    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    0.0841   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.1519   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -0.0665   -1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103    0.1969    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    0.2583    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9299    0.0998    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7898    0.4795    2.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0199    0.5411    2.9239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    0.6024    3.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    0.5150    2.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    0.5621    3.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -0.7643    3.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.3876    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    0.0011   -2.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.3004   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268    1.4345   -1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2874    0.2311   -2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4063    0.9129    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    1.3774    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -0.3843   -2.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728   -0.2291   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6140    0.1945    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963    0.7349    3.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297    0.7437    4.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -0.6994    4.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -1.1690    4.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -1.4345    2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1017   -0.2697   -3.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 20 11  2  0
  8 21  1  0
 20 17  1  0
 21  3  2  0
 12 11  1  0
  3  4  1  0
 17 16  2  0
  4  5  2  0
  5  7  1  0
 14 15  1  0
 20  7  1  0
 17 18  1  0
 11 10  1  0
  3  2  1  0
 10  9  2  0
  2  1  1  0
  9  8  1  0
 12 13  1  0
 16 14  1  0
 18 19  1  0
 14 12  2  0
  5  6  1  0
 16 31  1  0
 10 28  1  0
  9 27  1  0
 21 35  1  0
  4 25  1  0
 15 30  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 13 29  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
  6 26  1  0
M  END


  Mrv1652306202122313D          

 35 37  0  0  0  0            999 V2000
    3.6128    0.3939   -2.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.1385   -2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916    0.2657   -1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.6495   -0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    0.7362    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6491    1.2377    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    0.4087    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    0.0841   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.1519   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -0.0665   -1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103    0.1969    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    0.2583    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9299    0.0998    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7898    0.4795    2.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0199    0.5411    2.9239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    0.6024    3.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    0.5150    2.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    0.5621    3.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -0.7643    3.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.3876    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    0.0011   -2.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.3004   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268    1.4345   -1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2874    0.2311   -2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4063    0.9129    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    1.3774    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -0.3843   -2.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728   -0.2291   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6140    0.1945    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963    0.7349    3.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297    0.7437    4.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -0.6994    4.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -1.1690    4.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -1.4345    2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1017   -0.2697   -3.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
 20 11  2  0  0  0  0
  8 21  1  0  0  0  0
 20 17  1  0  0  0  0
 21  3  2  0  0  0  0
 12 11  1  0  0  0  0
  3  4  1  0  0  0  0
 17 16  2  0  0  0  0
  4  5  2  0  0  0  0
  5  7  1  0  0  0  0
 14 15  1  0  0  0  0
 20  7  1  0  0  0  0
 17 18  1  0  0  0  0
 11 10  1  0  0  0  0
  3  2  1  0  0  0  0
 10  9  2  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
 12 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18 19  1  0  0  0  0
 14 12  2  0  0  0  0
  5  6  1  0  0  0  0
 16 31  1  0  0  0  0
 10 28  1  0  0  0  0
  9 27  1  0  0  0  0
 21 35  1  0  0  0  0
  4 25  1  0  0  0  0
 15 30  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
 13 29  1  0  0  0  0
 19 32  1  0  0  0  0
 19 33  1  0  0  0  0
 19 34  1  0  0  0  0
  6 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(OC([H])([H])[H])=C([H])C2=C1C1=C(C([H])=C2[H])C(O[H])=C(O[H])C([H])=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-9-5-8-3-4-10-15(14(8)11(17)6-9)13(21-2)7-12(18)16(10)19/h3-7,17-19H,1-2H3

> <INCHI_KEY>
FBTSZZALORIKJQ-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.668529648698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7-dimethoxyphenanthrene-1,2,5-triol

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.726160833

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.340605117452284

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.649205765494695

> <JCHEM_PKA_STRONGEST_BASIC>
-4.543486469886192

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
77.8275

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7-dimethoxyphenanthrene-1,2,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    3.6128    0.3939   -2.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.1385   -2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916    0.2657   -1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.6495   -0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    0.7362    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6491    1.2377    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    0.4087    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    0.0841   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.1519   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -0.0665   -1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103    0.1969    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    0.2583    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9299    0.0998    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7898    0.4795    2.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0199    0.5411    2.9239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    0.6024    3.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    0.5150    2.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    0.5621    3.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -0.7643    3.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.3876    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    0.0011   -2.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.3004   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268    1.4345   -1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2874    0.2311   -2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4063    0.9129    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    1.3774    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -0.3843   -2.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728   -0.2291   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6140    0.1945    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963    0.7349    3.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297    0.7437    4.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -0.6994    4.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -1.1690    4.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -1.4345    2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1017   -0.2697   -3.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 20 11  2  0
  8 21  1  0
 20 17  1  0
 21  3  2  0
 12 11  1  0
  3  4  1  0
 17 16  2  0
  4  5  2  0
  5  7  1  0
 14 15  1  0
 20  7  1  0
 17 18  1  0
 11 10  1  0
  3  2  1  0
 10  9  2  0
  2  1  1  0
  9  8  1  0
 12 13  1  0
 16 14  1  0
 18 19  1  0
 14 12  2  0
  5  6  1  0
 16 31  1  0
 10 28  1  0
  9 27  1  0
 21 35  1  0
  4 25  1  0
 15 30  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 13 29  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
  6 26  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.613   0.394  -2.095  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.287   0.139  -2.542  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.292   0.266  -1.615  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.439   0.650  -0.298  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.317   0.736   0.543  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.649   1.238   1.777  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.021   0.409   0.135  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.120   0.084  -1.248  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.356  -0.152  -1.841  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.528  -0.067  -1.107  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.510   0.197   0.264  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.734   0.258   0.962  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.930   0.100   0.300  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.790   0.480   2.332  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.020   0.541   2.924  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.623   0.602   3.048  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.399   0.515   2.366  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.291   0.562   3.184  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.956  -0.764   3.620  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.268   0.388   0.940  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.010   0.001  -2.081  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.903  -0.300  -1.300  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.727   1.435  -1.774  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.287   0.231  -2.942  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.406   0.913   0.117  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.173   1.377   2.281  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.432  -0.384  -2.902  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.473  -0.229  -1.625  0.00  0.00           H+0
HETATM   29  H   UNK     0      -6.614   0.195   0.993  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.896   0.735   3.870  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.630   0.744   4.123  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.028  -0.699   4.195  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.734  -1.169   4.275  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.785  -1.435   2.770  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.102  -0.270  -3.131  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    1                                                       
CONECT    3   21    4    2                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    7    6                                                  
CONECT    6    5   26                                                       
CONECT    7    8    5   20                                                  
CONECT    8    7   21    9                                                  
CONECT    9   10    8   27                                                  
CONECT   10   11    9   28                                                  
CONECT   11   20   12   10                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   29                                                       
CONECT   14   15   16   12                                                  
CONECT   15   14   30                                                       
CONECT   16   17   14   31                                                  
CONECT   17   20   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   32   33   34                                             
CONECT   20   11   17    7                                                  
CONECT   21    8    3   35                                                  
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   13                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   19                                                            
CONECT   33   19                                                            
CONECT   34   19                                                            
CONECT   35   21                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
    3.6128    0.3939   -2.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.1385   -2.5421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916    0.2657   -1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.6495   -0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    0.7362    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6491    1.2377    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    0.4087    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    0.0841   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.1519   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -0.0665   -1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5103    0.1969    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    0.2583    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9299    0.0998    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7898    0.4795    2.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0199    0.5411    2.9239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    0.6024    3.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    0.5150    2.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    0.5621    3.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -0.7643    3.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    0.3876    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    0.0011   -2.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.3004   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268    1.4345   -1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2874    0.2311   -2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4063    0.9129    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    1.3774    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -0.3843   -2.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728   -0.2291   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6140    0.1945    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963    0.7349    3.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297    0.7437    4.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -0.6994    4.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -1.1690    4.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -1.4345    2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1017   -0.2697   -3.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 20 11  2  0
  8 21  1  0
 20 17  1  0
 21  3  2  0
 12 11  1  0
  3  4  1  0
 17 16  2  0
  4  5  2  0
  5  7  1  0
 14 15  1  0
 20  7  1  0
 17 18  1  0
 11 10  1  0
  3  2  1  0
 10  9  2  0
  2  1  1  0
  9  8  1  0
 12 13  1  0
 16 14  1  0
 18 19  1  0
 14 12  2  0
  5  6  1  0
 16 31  1  0
 10 28  1  0
  9 27  1  0
 21 35  1  0
  4 25  1  0
 15 30  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 13 29  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
  6 26  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

4,7-dimethoxyphenanthrene-1,2,5-triol

Traditional Name

4,7-dimethoxyphenanthrene-1,2,5-triol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(OC([H])([H])[H])=C([H])C2=C1C1=C(C([H])=C2[H])C(O[H])=C(O[H])C([H])=C1OC([H])([H])[H]

InChI Identifier

InChI=1S/C16H14O5/c1-20-9-5-8-3-4-10-15(14(8)11(17)6-9)13(21-2)7-12(18)16(10)19/h3-7,17-19H,1-2H3

InChI Key

FBTSZZALORIKJQ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	CannabisDB	Not Available
Cannabis sativa variety	JEOL database	Radwan, M. M., et al, Phytochem. 69, 2627 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

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	2.68	ALOGPS
logP	2.73	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.65	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.83 m³·mol⁻¹	ChemAxon
Polarizability	29.67 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

25172438

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Radwan, M. M., et al. (2008). Radwan, M. M., et al, Phytochem. 69, 2627 (2008). Phytochem..

Showing NP-Card for 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (NP0037649)

MOL for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

3D MOL for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

3D SDF for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

3D-SDF for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

PDB for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

3D PDB for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

SMILES for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

INCHI for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

Structure for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)

3D Structure for NP0037649 (4,7-dimethoxy-1,2,5-trihydroxyphenanthrene)