NP-MRD: Showing NP-Card for 3,7-dimethyl-8-hydroxy-6-methoxyisochroman (NP0021646)

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Record Information

Version

2.0

Created at

2021-01-06 06:55:37 UTC

Updated at

2021-07-15 17:36:54 UTC

NP-MRD ID

NP0021646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,7-dimethyl-8-hydroxy-6-methoxyisochroman

Provided By

NPAtlas

Description

3,4-Dihydro-6-methoxy-3,7-dimethyl-1H-2-benzopyran-8-ol, also known as DHMI-8 or 3,8-dihydroxy-1,2,4-trimethoxyxanthone, belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. 3,7-dimethyl-8-hydroxy-6-methoxyisochroman is found in Calophyllum teysmannii Miq.var.inophylloide, Penicillium citrinum, Penicillium corylophilum and Penicillium steckii. 3,7-dimethyl-8-hydroxy-6-methoxyisochroman was first documented in 1992 (PMID: 1284957). Based on a literature review very few articles have been published on 3,4-Dihydro-6-methoxy-3,7-dimethyl-1H-2-benzopyran-8-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105173D          

 31 32  0  0  0  0            999 V2000
   -3.0900    2.6646    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    1.2801    0.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986    0.5475    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.1226    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712    0.3588    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.9843   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8646   -1.5517   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -2.9192   -0.6360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144   -0.8020   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -1.4020   -0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -1.8754   -0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7538   -1.2456   -0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576    0.0758   -0.5836 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1670    0.6154   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    0.9130    0.3053 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0246    2.8272    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    3.0549   -0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    3.1767   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    2.1855    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -3.5285   -0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773   -1.5696    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -2.3740   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9826   -0.6846   -1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5412   -2.6599    0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -2.4525   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    0.2777   -1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    1.3006   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263   -0.2021   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932    1.1528    0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.7369    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    1.9614   -0.0107 H   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  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 15  1  0  0  0  0
  9  3  1  0  0  0  0
 15  5  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  4 19  1  0  0  0  0
  8 20  1  0  0  0  0
 10 21  1  0  0  0  0
 10 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 11 25  1  0  0  0  0
 13 26  1  6  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
M  END

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.0900    2.6646    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    1.2801    0.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986    0.5475    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.1226    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712    0.3588    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.9843   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8646   -1.5517   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -2.9192   -0.6360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144   -0.8020   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -1.4020   -0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -1.8754   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -1.2456   -0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576    0.0758   -0.5836 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1670    0.6154   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    0.9130    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246    2.8272    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    3.0549   -0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    3.1767   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    2.1855    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -3.5285   -0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773   -1.5696    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -2.3740   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9826   -0.6846   -1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5412   -2.6599    0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -2.4525   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    0.2777   -1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    1.3006   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263   -0.2021   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932    1.1528    0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.7369    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    1.9614   -0.0107 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9  3  1  0
 15  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  8 20  1  0
 10 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  6
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END


  Mrv1652306242105173D          

 31 32  0  0  0  0            999 V2000
   -3.0900    2.6646    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    1.2801    0.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986    0.5475    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.1226    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712    0.3588    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.9843   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8646   -1.5517   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -2.9192   -0.6360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144   -0.8020   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -1.4020   -0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -1.8754   -0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7538   -1.2456   -0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576    0.0758   -0.5836 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1670    0.6154   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    0.9130    0.3053 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0246    2.8272    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    3.0549   -0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    3.1767   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    2.1855    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -3.5285   -0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773   -1.5696    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -2.3740   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9826   -0.6846   -1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5412   -2.6599    0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -2.4525   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    0.2777   -1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    1.3006   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263   -0.2021   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932    1.1528    0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.7369    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    1.9614   -0.0107 H   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  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 15  1  0  0  0  0
  9  3  1  0  0  0  0
 15  5  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  4 19  1  0  0  0  0
  8 20  1  0  0  0  0
 10 21  1  0  0  0  0
 10 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 11 25  1  0  0  0  0
 13 26  1  6  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(OC([H])([H])[H])=C([H])C2=C1C([H])([H])O[C@]([H])(C([H])([H])[H])C2([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O3/c1-7-4-9-5-11(14-3)8(2)12(13)10(9)6-15-7/h5,7,13H,4,6H2,1-3H3/t7-/m1/s1

> <INCHI_KEY>
OQMJILQCXYKZEM-UHFFFAOYSA-N

> <FORMULA>
C12H16O3

> <MOLECULAR_WEIGHT>
208.2536

> <EXACT_MASS>
208.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.286899869644458

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-6-methoxy-3,7-dimethyl-3,4-dihydro-1H-2-benzopyran-8-ol

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.3576708853333335

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.543835764143285

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0904566633134944

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
58.838800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-6-methoxy-3,7-dimethyl-3,4-dihydro-1H-2-benzopyran-8-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.0900    2.6646    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    1.2801    0.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986    0.5475    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.1226    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712    0.3588    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.9843   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8646   -1.5517   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -2.9192   -0.6360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144   -0.8020   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -1.4020   -0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -1.8754   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -1.2456   -0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576    0.0758   -0.5836 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1670    0.6154   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    0.9130    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246    2.8272    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    3.0549   -0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    3.1767   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    2.1855    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -3.5285   -0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773   -1.5696    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -2.3740   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9826   -0.6846   -1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5412   -2.6599    0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -2.4525   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    0.2777   -1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    1.3006   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263   -0.2021   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932    1.1528    0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.7369    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    1.9614   -0.0107 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9  3  1  0
 15  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  8 20  1  0
 10 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  6
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.090   2.665   0.420  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.066   1.280   0.133  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.899   0.548   0.040  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.669   1.123   0.222  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.471   0.359   0.121  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.377  -0.984  -0.163  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.865  -1.552  -0.344  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.021  -2.919  -0.636  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.014  -0.802  -0.246  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.370  -1.402  -0.440  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.549  -1.875  -0.289  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.754  -1.246  -0.243  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.758   0.076  -0.584  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.167   0.615  -0.413  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.838   0.913   0.305  0.00  0.00           C+0
HETATM   16  H   UNK     0      -3.025   2.827   1.520  0.00  0.00           H+0
HETATM   17  H   UNK     0      -4.044   3.055  -0.004  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.269   3.177  -0.134  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.583   2.186   0.447  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.214  -3.529  -0.722  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.777  -1.570   0.590  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.249  -2.374  -0.957  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.983  -0.685  -1.019  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.541  -2.660   0.524  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.449  -2.453  -1.241  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.453   0.278  -1.634  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.452   1.301  -1.252  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.926  -0.202  -0.438  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.293   1.153   0.534  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.197   0.737   1.349  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.913   1.961  -0.011  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   20                                                       
CONECT    9    7   10    3                                                  
CONECT   10    9   21   22   23                                             
CONECT   11    6   12   24   25                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15   26                                             
CONECT   14   13   27   28   29                                             
CONECT   15   13    5   30   31                                             
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    4                                                            
CONECT   20    8                                                            
CONECT   21   10                                                            
CONECT   22   10                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   11                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   14                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   15                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

RDKit          3D

31 32  0  0  0  0  0  0  0  0999 V2000
   -3.0900    2.6646    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    1.2801    0.1333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986    0.5475    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.1226    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712    0.3588    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.9843   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8646   -1.5517   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -2.9192   -0.6360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144   -0.8020   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696   -1.4020   -0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -1.8754   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -1.2456   -0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576    0.0758   -0.5836 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1670    0.6154   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    0.9130    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246    2.8272    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    3.0549   -0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    3.1767   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    2.1855    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -3.5285   -0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773   -1.5696    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -2.3740   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9826   -0.6846   -1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5412   -2.6599    0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -2.4525   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    0.2777   -1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    1.3006   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263   -0.2021   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932    1.1528    0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.7369    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    1.9614   -0.0107 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9  3  1  0
 15  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  8 20  1  0
 10 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  6
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3,4-Dihydro-6-methoxy-3,7-dimethyl-1H-benzopyran-8-ol	HMDB
3,8-Dihydroxy-1,2,4-trimethoxyxanthone	HMDB
DHMI-8	HMDB

Chemical Formula

C₁₂H₁₆O₃

Average Mass

208.2536 Da

Monoisotopic Mass

208.10994 Da

IUPAC Name

(3R)-6-methoxy-3,7-dimethyl-3,4-dihydro-1H-2-benzopyran-8-ol

Traditional Name

(3R)-6-methoxy-3,7-dimethyl-3,4-dihydro-1H-2-benzopyran-8-ol

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(O)=C2COC(C)CC2=C1

InChI Identifier

InChI=1S/C12H16O3/c1-7-4-9-5-11(14-3)8(2)12(13)10(9)6-15-7/h5,7,13H,4,6H2,1-3H3

InChI Key

OQMJILQCXYKZEM-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
Calophyllum teysmannii Miq.var.inophylloide	Plant	KNApSAcK
Penicillium citrinum	LOTUS Database	35616633
Penicillium corylophilum	Fungi	KNApSAcK
Penicillium steckii	NPAtlas	546963

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic 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	2.09	ALOGPS
logP	2.36	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.54	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	58.84 m³·mol⁻¹	ChemAxon
Polarizability	23.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA017026

HMDB ID

HMDB0035224

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013873

KNApSAcK ID

C00036526

Chemspider ID

46202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50969

PDB ID

Not Available

ChEBI ID

173599

Good Scents ID

rw1429521

References

General References

Deruiter J, Jacyno JM, Davis RA, Cutler HG: Studies on aldose reductase inhibitors from fungi. I. Citrinin and related benzopyran derivatives. J Enzyme Inhib. 1992;6(3):201-10. doi: 10.3109/14756369209020170. [PubMed:1284957 ]

Showing NP-Card for 3,7-dimethyl-8-hydroxy-6-methoxyisochroman (NP0021646)

MOL for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

3D MOL for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

3D SDF for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

3D-SDF for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

PDB for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

3D PDB for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

SMILES for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

INCHI for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

Structure for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)

3D Structure for NP0021646 (3,7-dimethyl-8-hydroxy-6-methoxyisochroman)