NP-MRD: Showing NP-Card for (2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan (NP0038473)

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Record Information

Version

2.0

Created at

2021-06-20 21:09:07 UTC

Updated at

2021-06-30 00:11:17 UTC

NP-MRD ID

NP0038473

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan

Provided By

JEOL Database JEOL Logo

Description

3,4-Dihydro-2alpha-(1,3-benzodioxole-5-yl)-2H-1-benzopyran-3alpha,7-diol belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. (2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan is found in Habranthus brachyandrus. (2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan was first documented in 2009 (Jutsuno, M., et al.). Based on a literature review very few articles have been published on 3,4-Dihydro-2alpha-(1,3-benzodioxole-5-yl)-2H-1-benzopyran-3alpha,7-diol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123093D          

 35 38  0  0  0  0            999 V2000
   -4.2461    4.1370    1.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335    3.6406    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    3.6999   -0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873    3.2104   -1.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    2.6606   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    2.5877   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    3.0914    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    2.0729    0.3092 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    1.1973   -0.6701 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7768    0.7531   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423    1.6416    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105    1.2343    0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -0.0607    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4654   -0.9328   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2100   -0.5604   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0301   -2.1588   -0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089   -1.9559    0.4570 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4810   -0.6270    0.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612    1.8769   -2.0526 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1776    3.1222   -2.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    2.1456   -2.5209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8022    4.0301    2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    4.1308   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4482    3.2688   -2.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301    3.0399    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.2993   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262    2.6643    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.9155    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -1.2755   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1002   -2.1439   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4108   -2.6782    1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9718    1.2426   -2.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    3.6282   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9642    2.8753   -3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4168    1.2128   -2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
  3  4  1  0  0  0  0
 10 15  2  0  0  0  0
 15 14  1  0  0  0  0
  4  5  2  0  0  0  0
 13 12  1  0  0  0  0
  2  3  2  0  0  0  0
 12 11  2  0  0  0  0
 11 10  1  0  0  0  0
  6  7  2  0  0  0  0
 19 20  1  0  0  0  0
 13 14  2  0  0  0  0
  7  2  1  0  0  0  0
  6  8  1  0  0  0  0
  5 21  1  0  0  0  0
 21 19  1  0  0  0  0
 19  9  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 13  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  0  0  0  0
  7 25  1  0  0  0  0
 21 34  1  0  0  0  0
 21 35  1  0  0  0  0
 19 32  1  6  0  0  0
  9 26  1  6  0  0  0
  1 22  1  0  0  0  0
 15 29  1  0  0  0  0
 12 28  1  0  0  0  0
 11 27  1  0  0  0  0
 20 33  1  0  0  0  0
 17 30  1  0  0  0  0
 17 31  1  0  0  0  0
M  END

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
   -4.2461    4.1370    1.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335    3.6406    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    3.6999   -0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873    3.2104   -1.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    2.6606   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    2.5877   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    3.0914    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    2.0729    0.3092 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    1.1973   -0.6701 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7768    0.7531   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423    1.6416    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105    1.2343    0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -0.0607    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4654   -0.9328   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2100   -0.5604   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0301   -2.1588   -0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089   -1.9559    0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4810   -0.6270    0.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612    1.8769   -2.0526 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1776    3.1222   -2.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    2.1456   -2.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    4.0301    2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    4.1308   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4482    3.2688   -2.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301    3.0399    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.2993   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262    2.6643    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.9155    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -1.2755   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1002   -2.1439   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4108   -2.6782    1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9718    1.2426   -2.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    3.6282   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9642    2.8753   -3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4168    1.2128   -2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  6  5  1  0
  2  1  1  0
  9 10  1  0
  3  4  1  0
 10 15  2  0
 15 14  1  0
  4  5  2  0
 13 12  1  0
  2  3  2  0
 12 11  2  0
 11 10  1  0
  6  7  2  0
 19 20  1  0
 13 14  2  0
  7  2  1  0
  6  8  1  0
  5 21  1  0
 21 19  1  0
 19  9  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 13  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
 21 34  1  0
 21 35  1  0
 19 32  1  6
  9 26  1  6
  1 22  1  0
 15 29  1  0
 12 28  1  0
 11 27  1  0
 20 33  1  0
 17 30  1  0
 17 31  1  0
M  END


  Mrv1652306202123093D          

 35 38  0  0  0  0            999 V2000
   -4.2461    4.1370    1.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335    3.6406    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    3.6999   -0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873    3.2104   -1.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    2.6606   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    2.5877   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    3.0914    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    2.0729    0.3092 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    1.1973   -0.6701 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7768    0.7531   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423    1.6416    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105    1.2343    0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -0.0607    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4654   -0.9328   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2100   -0.5604   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0301   -2.1588   -0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089   -1.9559    0.4570 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4810   -0.6270    0.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612    1.8769   -2.0526 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1776    3.1222   -2.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    2.1456   -2.5209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8022    4.0301    2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    4.1308   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4482    3.2688   -2.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301    3.0399    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.2993   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262    2.6643    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.9155    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -1.2755   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1002   -2.1439   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4108   -2.6782    1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9718    1.2426   -2.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    3.6282   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9642    2.8753   -3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4168    1.2128   -2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
  3  4  1  0  0  0  0
 10 15  2  0  0  0  0
 15 14  1  0  0  0  0
  4  5  2  0  0  0  0
 13 12  1  0  0  0  0
  2  3  2  0  0  0  0
 12 11  2  0  0  0  0
 11 10  1  0  0  0  0
  6  7  2  0  0  0  0
 19 20  1  0  0  0  0
 13 14  2  0  0  0  0
  7  2  1  0  0  0  0
  6  8  1  0  0  0  0
  5 21  1  0  0  0  0
 21 19  1  0  0  0  0
 19  9  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 13  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  0  0  0  0
  7 25  1  0  0  0  0
 21 34  1  0  0  0  0
 21 35  1  0  0  0  0
 19 32  1  6  0  0  0
  9 26  1  6  0  0  0
  1 22  1  0  0  0  0
 15 29  1  0  0  0  0
 12 28  1  0  0  0  0
 11 27  1  0  0  0  0
 20 33  1  0  0  0  0
 17 30  1  0  0  0  0
 17 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038473

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C(O[C@]([H])(C3=C([H])C4=C(OC([H])([H])O4)C([H])=C3[H])[C@]([H])(O[H])C2([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c17-11-3-1-9-5-12(18)16(21-14(9)7-11)10-2-4-13-15(6-10)20-8-19-13/h1-4,6-7,12,16-18H,5,8H2/t12-,16-/m1/s1

> <INCHI_KEY>
ATNQMWUKQABBNL-MLGOLLRUSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.58906414841389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-3,7-diol

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.329036448

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.966534682582818

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.711918397020575

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2702296300790312

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
73.82390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-3,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
   -4.2461    4.1370    1.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335    3.6406    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    3.6999   -0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873    3.2104   -1.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    2.6606   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    2.5877   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    3.0914    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    2.0729    0.3092 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    1.1973   -0.6701 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7768    0.7531   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423    1.6416    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105    1.2343    0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -0.0607    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4654   -0.9328   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2100   -0.5604   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0301   -2.1588   -0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089   -1.9559    0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4810   -0.6270    0.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612    1.8769   -2.0526 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1776    3.1222   -2.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    2.1456   -2.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    4.0301    2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    4.1308   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4482    3.2688   -2.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301    3.0399    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.2993   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262    2.6643    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.9155    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -1.2755   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1002   -2.1439   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4108   -2.6782    1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9718    1.2426   -2.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    3.6282   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9642    2.8753   -3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4168    1.2128   -2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
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  2  1  1  0
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 17 31  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  O   UNK     0      -4.246   4.137   1.646  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.434   3.641   0.670  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.888   3.700  -0.642  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.087   3.210  -1.675  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.829   2.661  -1.395  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.400   2.588  -0.063  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.192   3.091   0.970  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.185   2.073   0.309  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.404   1.197  -0.670  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.777   0.753  -0.189  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.642   1.642   0.494  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.910   1.234   0.922  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.292  -0.061   0.653  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.465  -0.933  -0.013  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.210  -0.560  -0.447  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.030  -2.159  -0.180  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.309  -1.956   0.457  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.481  -0.627   0.991  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.461   1.877  -2.053  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.178   3.122  -2.018  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.970   2.146  -2.521  0.00  0.00           C+0
HETATM   22  H   UNK     0      -3.802   4.030   2.503  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.861   4.131  -0.861  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.448   3.269  -2.700  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.830   3.040   1.991  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.229   0.299  -0.722  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.326   2.664   0.692  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.572   1.916   1.444  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.585  -1.276  -0.972  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.100  -2.144  -0.278  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.411  -2.678   1.275  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.972   1.243  -2.786  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.828   3.628  -1.261  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.964   2.875  -3.339  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.417   1.213  -2.886  0.00  0.00           H+0
CONECT    1    2   22                                                       
CONECT    2    1    3    7                                                  
CONECT    3    4    2   23                                                  
CONECT    4    3    5   24                                                  
CONECT    5    6    4   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2   25                                                  
CONECT    8    9    6                                                       
CONECT    9    8   10   19   26                                             
CONECT   10    9   15   11                                                  
CONECT   11   12   10   27                                                  
CONECT   12   13   11   28                                                  
CONECT   13   12   14   18                                                  
CONECT   14   15   13   16                                                  
CONECT   15   10   14   29                                                  
CONECT   16   14   17                                                       
CONECT   17   16   18   30   31                                             
CONECT   18   17   13                                                       
CONECT   19   20   21    9   32                                             
CONECT   20   19   33                                                       
CONECT   21    5   19   34   35                                             
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    7                                                            
CONECT   26    9                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   15                                                            
CONECT   30   17                                                            
CONECT   31   17                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   21                                                            
CONECT   35   21                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

RDKit          3D

35 38  0  0  0  0  0  0  0  0999 V2000
   -4.2461    4.1370    1.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4335    3.6406    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    3.6999   -0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873    3.2104   -1.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    2.6606   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    2.5877   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    3.0914    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    2.0729    0.3092 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    1.1973   -0.6701 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7768    0.7531   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423    1.6416    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105    1.2343    0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -0.0607    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4654   -0.9328   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2100   -0.5604   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0301   -2.1588   -0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089   -1.9559    0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4810   -0.6270    0.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612    1.8769   -2.0526 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1776    3.1222   -2.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9699    2.1456   -2.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    4.0301    2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    4.1308   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4482    3.2688   -2.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301    3.0399    1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.2993   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262    2.6643    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.9155    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -1.2755   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1002   -2.1439   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4108   -2.6782    1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9718    1.2426   -2.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    3.6282   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9642    2.8753   -3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4168    1.2128   -2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  6  5  1  0
  2  1  1  0
  9 10  1  0
  3  4  1  0
 10 15  2  0
 15 14  1  0
  4  5  2  0
 13 12  1  0
  2  3  2  0
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 11 10  1  0
  6  7  2  0
 19 20  1  0
 13 14  2  0
  7  2  1  0
  6  8  1  0
  5 21  1  0
 21 19  1  0
 19  9  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 13  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
 21 34  1  0
 21 35  1  0
 19 32  1  6
  9 26  1  6
  1 22  1  0
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 12 28  1  0
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 20 33  1  0
 17 30  1  0
 17 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
3,4-Dihydro-2a-(1,3-benzodioxole-5-yl)-2H-1-benzopyran-3a,7-diol	Generator
3,4-Dihydro-2α-(1,3-benzodioxole-5-yl)-2H-1-benzopyran-3α,7-diol	Generator

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

(2R,3R)-2-(2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-3,7-diol

Traditional Name

(2R,3R)-2-(2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-3,7-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C(O[C@]([H])(C3=C([H])C4=C(OC([H])([H])O4)C([H])=C3[H])[C@]([H])(O[H])C2([H])[H])=C1[H]

InChI Identifier

InChI=1S/C16H14O5/c17-11-3-1-9-5-12(18)16(21-14(9)7-11)10-2-4-13-15(6-10)20-8-19-13/h1-4,6-7,12,16-18H,5,8H2/t12-,16-/m1/s1

InChI Key

ATNQMWUKQABBNL-MLGOLLRUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Zephyranthes brachyandra	JEOL database	Jutsuno, M., et al, Chem. Pharm. Bull. 57, 1153 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

3-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Chromane
1-benzopyran
Benzopyran
Benzodioxole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

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	2.05	ALOGPS
logP	2.33	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.71	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.82 m³·mol⁻¹	ChemAxon
Polarizability	29.59 Å³	ChemAxon
Number of Rings	4	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

44475662

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jutsuno, M., et al. (2009). Jutsuno, M., et al, Chem. Pharm. Bull. 57, 1153 (2009). Chem. Pharm. Bull..

Showing NP-Card for (2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan (NP0038473)

MOL for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

3D MOL for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

3D SDF for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

3D-SDF for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

PDB for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

3D PDB for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

SMILES for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

INCHI for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

Structure for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)

3D Structure for NP0038473 ((2R,3R)-3,7-dihydroxy-3',4'-methylenedioxyflavan)