NP-MRD: Showing NP-Card for (-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan (NP0041702)

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Record Information

Version

2.0

Created at

2021-06-20 23:33:25 UTC

Updated at

2021-06-30 00:16:22 UTC

NP-MRD ID

NP0041702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan

Provided By

JEOL Database JEOL Logo

Description

ZINC1620282 belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. (-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan is found in Derris oblonga, Petalostemum purpureum, Sophora japonica L. and Sophora mollis subsp. griffithii (Stocks) Ali. (-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan was first documented in 2012 (Atta-ur-Rahman, et al.). Based on a literature review very few articles have been published on ZINC1620282.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101333D          

 33 37  0  0  0  0            999 V2000
    5.6433   -2.2725   -0.8948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5796   -1.4302   -1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133   -0.1333   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6550    0.7671   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.3577   -1.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408   -0.9541   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.8500   -1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -1.4465   -2.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803   -0.5468   -2.5085 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0346    0.4498   -1.3751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9184    1.5790   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761    1.6522   -1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704    2.8636   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647    3.9337   -0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8112    3.8732   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    2.6741   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    2.4058   -0.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.2858   -1.4904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9625    5.0145   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2400    4.5111   -0.9263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1906    3.1515   -1.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -3.1365   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421    0.1760   -0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649    1.7823   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -2.8603   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287   -1.1579   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446   -0.0624   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -0.0829   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    0.8194   -1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    4.7075   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319    1.7132   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    4.5606   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6097    5.1539   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 18 17  1  0  0  0  0
 17 16  1  0  0  0  0
 11 10  1  0  0  0  0
  5  6  2  0  0  0  0
  4  3  2  0  0  0  0
 11 16  2  0  0  0  0
  5 18  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  2  0  0  0  0
  6  7  1  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
 13 14  1  0  0  0  0
  6  8  1  0  0  0  0
  7  2  2  0  0  0  0
  3  2  1  0  0  0  0
  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 13  1  0  0  0  0
 10 18  1  0  0  0  0
 18 31  1  6  0  0  0
  9 10  1  0  0  0  0
 10 28  1  1  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
  4 24  1  0  0  0  0
  3 23  1  0  0  0  0
  7 25  1  0  0  0  0
  1 22  1  0  0  0  0
 15 30  1  0  0  0  0
 12 29  1  0  0  0  0
 20 32  1  0  0  0  0
 20 33  1  0  0  0  0
M  END

     RDKit          3D

 33 37  0  0  0  0  0  0  0  0999 V2000
    5.6433   -2.2725   -0.8948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5796   -1.4302   -1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133   -0.1333   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6550    0.7671   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.3577   -1.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408   -0.9541   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.8500   -1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -1.4465   -2.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803   -0.5468   -2.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    0.4498   -1.3751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9184    1.5790   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761    1.6522   -1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704    2.8636   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647    3.9337   -0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8112    3.8732   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    2.6741   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    2.4058   -0.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.2858   -1.4904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9625    5.0145   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2400    4.5111   -0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906    3.1515   -1.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -3.1365   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421    0.1760   -0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649    1.7823   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -2.8603   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287   -1.1579   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446   -0.0624   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -0.0829   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    0.8194   -1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    4.7075   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319    1.7132   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    4.5606   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6097    5.1539   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 18 17  1  0
 17 16  1  0
 11 10  1  0
  5  6  2  0
  4  3  2  0
 11 16  2  0
  5 18  1  0
 16 15  1  0
 15 14  2  0
  6  7  1  0
 13 12  2  0
 12 11  1  0
 13 14  1  0
  6  8  1  0
  7  2  2  0
  3  2  1  0
  8  9  1  0
  2  1  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 21 13  1  0
 10 18  1  0
 18 31  1  6
  9 10  1  0
 10 28  1  1
  9 26  1  0
  9 27  1  0
  4 24  1  0
  3 23  1  0
  7 25  1  0
  1 22  1  0
 15 30  1  0
 12 29  1  0
 20 32  1  0
 20 33  1  0
M  END


  Mrv1652306212101333D          

 33 37  0  0  0  0            999 V2000
    5.6433   -2.2725   -0.8948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5796   -1.4302   -1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133   -0.1333   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6550    0.7671   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.3577   -1.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408   -0.9541   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.8500   -1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -1.4465   -2.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803   -0.5468   -2.5085 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0346    0.4498   -1.3751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9184    1.5790   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761    1.6522   -1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704    2.8636   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647    3.9337   -0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8112    3.8732   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    2.6741   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    2.4058   -0.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.2858   -1.4904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9625    5.0145   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2400    4.5111   -0.9263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1906    3.1515   -1.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -3.1365   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421    0.1760   -0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649    1.7823   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -2.8603   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287   -1.1579   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446   -0.0624   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -0.0829   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    0.8194   -1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    4.7075   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319    1.7132   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    4.5606   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6097    5.1539   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 18 17  1  0  0  0  0
 17 16  1  0  0  0  0
 11 10  1  0  0  0  0
  5  6  2  0  0  0  0
  4  3  2  0  0  0  0
 11 16  2  0  0  0  0
  5 18  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  2  0  0  0  0
  6  7  1  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
 13 14  1  0  0  0  0
  6  8  1  0  0  0  0
  7  2  2  0  0  0  0
  3  2  1  0  0  0  0
  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 13  1  0  0  0  0
 10 18  1  0  0  0  0
 18 31  1  6  0  0  0
  9 10  1  0  0  0  0
 10 28  1  1  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
  4 24  1  0  0  0  0
  3 23  1  0  0  0  0
  7 25  1  0  0  0  0
  1 22  1  0  0  0  0
 15 30  1  0  0  0  0
 12 29  1  0  0  0  0
 20 32  1  0  0  0  0
 20 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1[H])[C@]1([H])OC3=C(C([H])=C4OC([H])([H])OC4=C3[H])[C@@]1([H])C([H])([H])O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16+/m1/s1

> <INCHI_KEY>
HUKSJTUUSUGIDC-BZNIZROVSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.51345708823228

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13(18),14,16-hexaen-16-ol

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.2901281296666665

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.42075412224077

> <JCHEM_PKA_STRONGEST_BASIC>
-4.35223300261882

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
72.36480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13(18),14,16-hexaen-16-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 37  0  0  0  0  0  0  0  0999 V2000
    5.6433   -2.2725   -0.8948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5796   -1.4302   -1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133   -0.1333   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6550    0.7671   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.3577   -1.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408   -0.9541   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.8500   -1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -1.4465   -2.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803   -0.5468   -2.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    0.4498   -1.3751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9184    1.5790   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761    1.6522   -1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704    2.8636   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647    3.9337   -0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8112    3.8732   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    2.6741   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    2.4058   -0.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.2858   -1.4904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9625    5.0145   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2400    4.5111   -0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906    3.1515   -1.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -3.1365   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421    0.1760   -0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649    1.7823   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -2.8603   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287   -1.1579   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446   -0.0624   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -0.0829   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    0.8194   -1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    4.7075   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319    1.7132   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    4.5606   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6097    5.1539   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 18 17  1  0
 17 16  1  0
 11 10  1  0
  5  6  2  0
  4  3  2  0
 11 16  2  0
  5 18  1  0
 16 15  1  0
 15 14  2  0
  6  7  1  0
 13 12  2  0
 12 11  1  0
 13 14  1  0
  6  8  1  0
  7  2  2  0
  3  2  1  0
  8  9  1  0
  2  1  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 21 13  1  0
 10 18  1  0
 18 31  1  6
  9 10  1  0
 10 28  1  1
  9 26  1  0
  9 27  1  0
  4 24  1  0
  3 23  1  0
  7 25  1  0
  1 22  1  0
 15 30  1  0
 12 29  1  0
 20 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       5.643  -2.272  -0.895  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.580  -1.430  -1.038  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.713  -0.133  -0.551  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.655   0.767  -0.674  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.462   0.358  -1.276  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.341  -0.954  -1.773  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.401  -1.850  -1.649  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.202  -1.446  -2.372  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.080  -0.547  -2.509  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.035   0.450  -1.375  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.918   1.579  -1.291  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.276   1.652  -1.541  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.870   2.864  -1.239  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.165   3.934  -0.707  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.811   3.873  -0.443  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.207   2.674  -0.758  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.142   2.406  -0.592  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.306   1.286  -1.490  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.962   5.014  -0.485  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.240   4.511  -0.926  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.191   3.151  -1.407  0.00  0.00           O+0
HETATM   22  H   UNK     0       5.406  -3.136  -1.270  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.642   0.176  -0.079  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.765   1.782  -0.299  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.292  -2.860  -2.029  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.829  -1.158  -2.515  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.145  -0.062  -3.490  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.002  -0.083  -0.412  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.851   0.819  -1.924  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.263   4.707  -0.028  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.432   1.713  -2.500  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.944   4.561  -0.088  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.610   5.154  -1.734  0.00  0.00           H+0
CONECT    1    2   22                                                       
CONECT    2    7    3    1                                                  
CONECT    3    4    2   23                                                  
CONECT    4    5    3   24                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2   25                                                  
CONECT    8    6    9                                                       
CONECT    9    8   10   26   27                                             
CONECT   10   11   18    9   28                                             
CONECT   11   10   16   12                                                  
CONECT   12   13   11   29                                                  
CONECT   13   12   14   21                                                  
CONECT   14   15   13   19                                                  
CONECT   15   16   14   30                                                  
CONECT   16   17   11   15                                                  
CONECT   17   18   16                                                       
CONECT   18   17    5   10   31                                             
CONECT   19   14   20                                                       
CONECT   20   19   21   32   33                                             
CONECT   21   20   13                                                       
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    7                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   12                                                            
CONECT   30   15                                                            
CONECT   31   18                                                            
CONECT   32   20                                                            
CONECT   33   20                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

RDKit          3D

33 37  0  0  0  0  0  0  0  0999 V2000
    5.6433   -2.2725   -0.8948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5796   -1.4302   -1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133   -0.1333   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6550    0.7671   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.3577   -1.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408   -0.9541   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.8500   -1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -1.4465   -2.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803   -0.5468   -2.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    0.4498   -1.3751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9184    1.5790   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761    1.6522   -1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704    2.8636   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647    3.9337   -0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8112    3.8732   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    2.6741   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    2.4058   -0.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.2858   -1.4904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9625    5.0145   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2400    4.5111   -0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906    3.1515   -1.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064   -3.1365   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421    0.1760   -0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649    1.7823   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -2.8603   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8287   -1.1579   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446   -0.0624   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -0.0829   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8507    0.8194   -1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    4.7075   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319    1.7132   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    4.5606   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6097    5.1539   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 18 17  1  0
 17 16  1  0
 11 10  1  0
  5  6  2  0
  4  3  2  0
 11 16  2  0
  5 18  1  0
 16 15  1  0
 15 14  2  0
  6  7  1  0
 13 12  2  0
 12 11  1  0
 13 14  1  0
  6  8  1  0
  7  2  2  0
  3  2  1  0
  8  9  1  0
  2  1  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 21 13  1  0
 10 18  1  0
 18 31  1  6
  9 10  1  0
 10 28  1  1
  9 26  1  0
  9 27  1  0
  4 24  1  0
  3 23  1  0
  7 25  1  0
  1 22  1  0
 15 30  1  0
 12 29  1  0
 20 32  1  0
 20 33  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2670 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

(1S,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13(18),14,16-hexaen-16-ol

Traditional Name

(1S,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13(18),14,16-hexaen-16-ol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1[H])[C@]1([H])OC3=C(C([H])=C4OC([H])([H])OC4=C3[H])[C@@]1([H])C([H])([H])O2

InChI Identifier

InChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16+/m1/s1

InChI Key

HUKSJTUUSUGIDC-BZNIZROVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Derris oblonga	Plant	KNApSAcK
Petalostemum purpureum	-	KNApSAcK
Sophora japonica L.	Plant	KNApSAcK
Sophora mollis subsp. griffithii (Stocks) Ali	JEOL database	Atta-ur-Rahman, et al, Phytochem. Lett. 5, 613 (2012)

Chemical Taxonomy

Classification

Not classified

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	2.19	ALOGPS
logP	2.29	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.36 m³·mol⁻¹	ChemAxon
Polarizability	29.51 Å³	ChemAxon
Number of Rings	5	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

36689163

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Atta-ur-Rahman, et al. (2012). Atta-ur-Rahman, et al, Phytochem. Lett. 5, 613 (2012). Phytochem..

Showing NP-Card for (-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan (NP0041702)

MOL for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

3D MOL for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

3D SDF for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

3D-SDF for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

PDB for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

3D PDB for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

SMILES for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

INCHI for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

Structure for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)

3D Structure for NP0041702 ((-)-3-hydroxy-8,9-methylenedioxy-(6aR,11aS)-pterocarpan)