NP-MRD: Showing NP-Card for 8-methoxyisobonducellin (NP0032832)

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Record Information

Version

2.0

Created at

2021-06-19 23:32:35 UTC

Updated at

2021-06-30 00:02:15 UTC

NP-MRD ID

NP0032832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-methoxyisobonducellin

Provided By

JEOL Database JEOL Logo

Description

3-[(Z)-4-Methoxybenzylidene]-7-hydroxy-8-methoxy-2,3-dihydro-4H-1-benzopyran-4-one belongs to the class of organic compounds known as homoisoflavonoids. These are naturally occurring oxygen heterocycles with a structure based on a 16-carbon skeleton including a chromanone, chromone or chromane system with a benzyl group at position C-3. 8-methoxyisobonducellin is found in Caesalpinia millettii, Caesalpinia sappan , Caesalpinia pulcherrima , Hoffmannseggia intricata and Microdesmis keayana. 8-methoxyisobonducellin was first documented in 2007 (Chen, P., et al.). Based on a literature review very few articles have been published on 3-[(Z)-4-Methoxybenzylidene]-7-hydroxy-8-methoxy-2,3-dihydro-4H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101323D          

 39 41  0  0  0  0            999 V2000
    4.8844   -0.8486    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269    0.3765    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.7316    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171    1.9840    1.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    2.4714    1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    1.7111    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    2.2224    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6906    2.3701   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    2.8715   -0.0921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0442    1.9590   -0.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586    1.6921   -1.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    1.7792   -2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    1.5396   -3.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5214    1.2110   -4.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7710    1.1050   -4.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8352    0.7773   -4.9172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577    1.3132   -2.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2585    1.1677   -2.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4378    0.6576   -1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050    2.0997   -1.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893    2.1661   -2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559    0.4485    0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.0367    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -1.7001    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9688   -0.9654    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -0.8351   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197    2.5885    1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    3.4523    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081    2.4934    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    2.9803    0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    3.8612   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    1.6102   -4.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    1.0325   -5.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6119    0.7836   -4.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7057   -0.1181   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4302    0.1978   -0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4248    1.4719   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0637   -0.1693   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3439   -1.0164   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  2  0  0  0  0
 11 17  2  0  0  0  0
 17 15  1  0  0  0  0
 11 12  1  0  0  0  0
 22  6  1  0  0  0  0
  6  5  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  2  1  1  0  0  0  0
 11 10  1  0  0  0  0
 12 20  1  0  0  0  0
 20  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 23  1  0  0  0  0
 15 16  1  0  0  0  0
 15 14  2  0  0  0  0
 20 21  2  0  0  0  0
  5  4  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
 14 13  1  0  0  0  0
 17 18  1  0  0  0  0
 13 12  2  0  0  0  0
 18 19  1  0  0  0  0
  5 28  1  0  0  0  0
  4 27  1  0  0  0  0
 23 39  1  0  0  0  0
 22 38  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 14 33  1  0  0  0  0
 13 32  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
 16 34  1  0  0  0  0
  7 29  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    4.8844   -0.8486    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269    0.3765    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.7316    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171    1.9840    1.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    2.4714    1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    1.7111    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    2.2224    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6906    2.3701   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    2.8715   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0442    1.9590   -0.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586    1.6921   -1.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    1.7792   -2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    1.5396   -3.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5214    1.2110   -4.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7710    1.1050   -4.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8352    0.7773   -4.9172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577    1.3132   -2.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2585    1.1677   -2.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4378    0.6576   -1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050    2.0997   -1.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893    2.1661   -2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559    0.4485    0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.0367    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -1.7001    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9688   -0.9654    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -0.8351   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197    2.5885    1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    3.4523    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081    2.4934    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    2.9803    0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    3.8612   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    1.6102   -4.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    1.0325   -5.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6119    0.7836   -4.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7057   -0.1181   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4302    0.1978   -0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4248    1.4719   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0637   -0.1693   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3439   -1.0164   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  2  0
 11 17  2  0
 17 15  1  0
 11 12  1  0
 22  6  1  0
  6  5  2  0
  3  2  1  0
  4  3  2  0
  2  1  1  0
 11 10  1  0
 12 20  1  0
 20  8  1  0
  8  9  1  0
  9 10  1  0
  3 23  1  0
 15 16  1  0
 15 14  2  0
 20 21  2  0
  5  4  1  0
  8  7  2  0
  7  6  1  0
 14 13  1  0
 17 18  1  0
 13 12  2  0
 18 19  1  0
  5 28  1  0
  4 27  1  0
 23 39  1  0
 22 38  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 14 33  1  0
 13 32  1  0
  9 30  1  0
  9 31  1  0
 16 34  1  0
  7 29  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
M  END


  Mrv1652306202101323D          

 39 41  0  0  0  0            999 V2000
    4.8844   -0.8486    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269    0.3765    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.7316    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171    1.9840    1.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    2.4714    1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    1.7111    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    2.2224    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6906    2.3701   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    2.8715   -0.0921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0442    1.9590   -0.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586    1.6921   -1.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    1.7792   -2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    1.5396   -3.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5214    1.2110   -4.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7710    1.1050   -4.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8352    0.7773   -4.9172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577    1.3132   -2.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2585    1.1677   -2.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4378    0.6576   -1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050    2.0997   -1.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893    2.1661   -2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559    0.4485    0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.0367    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -1.7001    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9688   -0.9654    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -0.8351   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197    2.5885    1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    3.4523    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081    2.4934    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    2.9803    0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    3.8612   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    1.6102   -4.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    1.0325   -5.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6119    0.7836   -4.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7057   -0.1181   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4302    0.1978   -0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4248    1.4719   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0637   -0.1693   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3439   -1.0164   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  2  0  0  0  0
 11 17  2  0  0  0  0
 17 15  1  0  0  0  0
 11 12  1  0  0  0  0
 22  6  1  0  0  0  0
  6  5  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  2  1  1  0  0  0  0
 11 10  1  0  0  0  0
 12 20  1  0  0  0  0
 20  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 23  1  0  0  0  0
 15 16  1  0  0  0  0
 15 14  2  0  0  0  0
 20 21  2  0  0  0  0
  5  4  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
 14 13  1  0  0  0  0
 17 18  1  0  0  0  0
 13 12  2  0  0  0  0
 18 19  1  0  0  0  0
  5 28  1  0  0  0  0
  4 27  1  0  0  0  0
 23 39  1  0  0  0  0
 22 38  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 14 33  1  0  0  0  0
 13 32  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
 16 34  1  0  0  0  0
  7 29  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C(=O)\C(=C(\[H])C3=C([H])C([H])=C(OC([H])([H])[H])C([H])=C3[H])C([H])([H])OC2=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-21-13-5-3-11(4-6-13)9-12-10-23-17-14(16(12)20)7-8-15(19)18(17)22-2/h3-9,19H,10H2,1-2H3/b12-9-

> <INCHI_KEY>
WOXQROZUZURVHX-XFXZXTDPSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.321

> <EXACT_MASS>
312.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.78920798568879

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-7-hydroxy-8-methoxy-3-[(4-methoxyphenyl)methylidene]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
2.747102591666667

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.428646062108301

> <JCHEM_PKA_STRONGEST_BASIC>
-4.444232791763431

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
86.11800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-7-hydroxy-8-methoxy-3-[(4-methoxyphenyl)methylidene]-2H-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    4.8844   -0.8486    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269    0.3765    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.7316    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171    1.9840    1.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    2.4714    1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    1.7111    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    2.2224    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6906    2.3701   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    2.8715   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0442    1.9590   -0.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586    1.6921   -1.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    1.7792   -2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    1.5396   -3.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5214    1.2110   -4.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7710    1.1050   -4.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8352    0.7773   -4.9172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577    1.3132   -2.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2585    1.1677   -2.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4378    0.6576   -1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050    2.0997   -1.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893    2.1661   -2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559    0.4485    0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.0367    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -1.7001    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9688   -0.9654    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -0.8351   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197    2.5885    1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    3.4523    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081    2.4934    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    2.9803    0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    3.8612   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    1.6102   -4.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    1.0325   -5.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6119    0.7836   -4.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7057   -0.1181   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4302    0.1978   -0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4248    1.4719   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0637   -0.1693   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3439   -1.0164   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  2  0
 11 17  2  0
 17 15  1  0
 11 12  1  0
 22  6  1  0
  6  5  2  0
  3  2  1  0
  4  3  2  0
  2  1  1  0
 11 10  1  0
 12 20  1  0
 20  8  1  0
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  9 10  1  0
  3 23  1  0
 15 16  1  0
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  5  4  1  0
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  5 28  1  0
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 23 39  1  0
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  1 24  1  0
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 14 33  1  0
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  9 30  1  0
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 16 34  1  0
  7 29  1  0
 19 35  1  0
 19 36  1  0
 19 37  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       4.884  -0.849   0.044  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.527   0.377   0.671  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.207   0.732   0.620  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.917   1.984   1.165  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.607   2.471   1.176  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.567   1.711   0.635  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.807   2.222   0.707  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.691   2.370  -0.298  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.084   2.872  -0.092  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.044   1.959  -0.632  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.859   1.692  -1.964  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.590   1.779  -2.561  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.421   1.540  -3.932  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.521   1.211  -4.718  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.771   1.105  -4.120  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.835   0.777  -4.917  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.958   1.313  -2.746  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.258   1.168  -2.329  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.438   0.658  -1.011  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.405   2.100  -1.733  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.289   2.166  -2.229  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.856   0.449   0.106  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.170  -0.037   0.092  0.00  0.00           C+0
HETATM   24  H   UNK     0       4.416  -1.700   0.548  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.969  -0.965   0.133  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.638  -0.835  -1.023  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.720   2.588   1.579  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.413   3.452   1.603  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.108   2.493   1.718  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.314   2.980   0.974  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.220   3.861  -0.548  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.435   1.610  -4.386  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.407   1.032  -5.783  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.612   0.784  -4.324  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.706  -0.118  -0.761  0.00  0.00           H+0
HETATM   36  H   UNK     0      -7.430   0.198  -0.968  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.425   1.472  -0.281  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.064  -0.169  -0.309  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.344  -1.016  -0.339  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   27                                                  
CONECT    5    6    4   28                                                  
CONECT    6   22    5    7                                                  
CONECT    7    8    6   29                                                  
CONECT    8   20    9    7                                                  
CONECT    9    8   10   30   31                                             
CONECT   10   11    9                                                       
CONECT   11   17   12   10                                                  
CONECT   12   11   20   13                                                  
CONECT   13   14   12   32                                                  
CONECT   14   15   13   33                                                  
CONECT   15   17   16   14                                                  
CONECT   16   15   34                                                       
CONECT   17   11   15   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   35   36   37                                             
CONECT   20   12    8   21                                                  
CONECT   21   20                                                            
CONECT   22   23    6   38                                                  
CONECT   23   22    3   39                                                  
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   16                                                            
CONECT   35   19                                                            
CONECT   36   19                                                            
CONECT   37   19                                                            
CONECT   38   22                                                            
CONECT   39   23                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
    4.8844   -0.8486    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269    0.3765    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.7316    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171    1.9840    1.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    2.4714    1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    1.7111    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    2.2224    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6906    2.3701   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    2.8715   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0442    1.9590   -0.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586    1.6921   -1.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    1.7792   -2.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    1.5396   -3.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5214    1.2110   -4.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7710    1.1050   -4.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8352    0.7773   -4.9172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577    1.3132   -2.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2585    1.1677   -2.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4378    0.6576   -1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050    2.0997   -1.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893    2.1661   -2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559    0.4485    0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.0367    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -1.7001    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9688   -0.9654    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -0.8351   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197    2.5885    1.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    3.4523    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081    2.4934    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    2.9803    0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    3.8612   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    1.6102   -4.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    1.0325   -5.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6119    0.7836   -4.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7057   -0.1181   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4302    0.1978   -0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4248    1.4719   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0637   -0.1693   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3439   -1.0164   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  2  0
 11 17  2  0
 17 15  1  0
 11 12  1  0
 22  6  1  0
  6  5  2  0
  3  2  1  0
  4  3  2  0
  2  1  1  0
 11 10  1  0
 12 20  1  0
 20  8  1  0
  8  9  1  0
  9 10  1  0
  3 23  1  0
 15 16  1  0
 15 14  2  0
 20 21  2  0
  5  4  1  0
  8  7  2  0
  7  6  1  0
 14 13  1  0
 17 18  1  0
 13 12  2  0
 18 19  1  0
  5 28  1  0
  4 27  1  0
 23 39  1  0
 22 38  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 14 33  1  0
 13 32  1  0
  9 30  1  0
  9 31  1  0
 16 34  1  0
  7 29  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3210 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

(3Z)-7-hydroxy-8-methoxy-3-[(4-methoxyphenyl)methylidene]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(3Z)-7-hydroxy-8-methoxy-3-[(4-methoxyphenyl)methylidene]-2H-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C(=O)\C(=C(\[H])C3=C([H])C([H])=C(OC([H])([H])[H])C([H])=C3[H])C([H])([H])OC2=C1OC([H])([H])[H]

InChI Identifier

InChI=1S/C18H16O5/c1-21-13-5-3-11(4-6-13)9-12-10-23-17-14(16(12)20)7-8-15(19)18(17)22-2/h3-9,19H,10H2,1-2H3/b12-9-

InChI Key

WOXQROZUZURVHX-XFXZXTDPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-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
Biancaea millettii	JEOL database	Chen, P., et al, Chem. Pharm. Bull. 55, 655 (2007)
Biancaea sappan	Plant	KNApSAcK
Caesalpinia pulcherrima	Plant	KNApSAcK
Hoffmannseggia intricata	Plant	KNApSAcK
Microdesmis keayana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavonoids. These are naturally occurring oxygen heterocycles with a structure based on a 16-carbon skeleton including a chromanone, chromone or chromane system with a benzyl group at position C-3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Not Available

Direct Parent

Homoisoflavonoids

Alternative Parents

Substituents

Homoisoflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Phenoxy compound
Phenol ether
Aryl ketone
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Aldehyde
Organooxygen compound
Organic oxide
Organic oxygen 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	3.18	ALOGPS
logP	2.75	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.12 m³·mol⁻¹	ChemAxon
Polarizability	32.79 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

17588785

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16655474

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen, P., et al. (2007). Chen, P., et al, Chem. Pharm. Bull. 55, 655 (2007) . Chem. Pharm. Bull..

Showing NP-Card for 8-methoxyisobonducellin (NP0032832)

MOL for NP0032832 (8-methoxyisobonducellin)

3D MOL for NP0032832 (8-methoxyisobonducellin)

3D SDF for NP0032832 (8-methoxyisobonducellin)

3D-SDF for NP0032832 (8-methoxyisobonducellin)

PDB for NP0032832 (8-methoxyisobonducellin)

3D PDB for NP0032832 (8-methoxyisobonducellin)

SMILES for NP0032832 (8-methoxyisobonducellin)

INCHI for NP0032832 (8-methoxyisobonducellin)

Structure for NP0032832 (8-methoxyisobonducellin)

3D Structure for NP0032832 (8-methoxyisobonducellin)