NP-MRD: Showing NP-Card for 9-O-methyl-4-hydroxyboeravinone B (NP0025538)

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Record Information

Version

2.0

Created at

2021-06-19 17:38:10 UTC

Updated at

2021-06-29 23:50:34 UTC

NP-MRD ID

NP0025538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-O-methyl-4-hydroxyboeravinone B

Provided By

JEOL Database JEOL Logo

Description

ZINC6520505 belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. 9-O-methyl-4-hydroxyboeravinone B is found in Mirabilis jalapa. 9-O-methyl-4-hydroxyboeravinone B was first documented in 2001 (Yang, S.-W., et al.). Based on a literature review very few articles have been published on ZINC6520505.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119383D          

 39 42  0  0  0  0            999 V2000
    3.6911   -3.4104   -0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512   -2.0751   -0.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -1.0884   -0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8314   -1.3096   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -0.2421   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.5463   -0.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    0.4804   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9831    1.7780    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4592    2.1363    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726    3.2762    0.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309    1.0483   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    1.2799   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347    2.5366    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    0.2211   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2015    0.4712   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1024    2.7281    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682    4.1177    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667    4.9707    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183    4.4497    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630    3.0779    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6962    2.5791    1.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    2.2205    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.8804    0.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453    0.0349   -0.0398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8661   -1.2794    0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -3.7496    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -3.5102   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685   -4.0544   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -2.3034   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936    3.1671    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035    0.2973    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4441    1.4946   -0.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -0.1841   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    4.5730   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9381    6.0456    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    5.1066    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5818    1.6128    1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021   -0.0139   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -1.3306    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
  8  7  2  0  0  0  0
 14  3  2  0  0  0  0
 14 12  1  0  0  0  0
  3  4  1  0  0  0  0
 11  9  1  0  0  0  0
  8 16  1  0  0  0  0
  7 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  1  0  0  0  0
 16 22  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  4  5  2  0  0  0  0
  9 10  2  0  0  0  0
 11 12  2  0  0  0  0
 16 17  1  0  0  0  0
 22 20  1  0  0  0  0
 20 19  2  0  0  0  0
 19 18  1  0  0  0  0
 18 17  2  0  0  0  0
 12 13  1  0  0  0  0
 20 21  1  0  0  0  0
 11  5  1  0  0  0  0
 24 25  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  4 29  1  0  0  0  0
 13 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 24 38  1  0  0  0  0
 19 36  1  0  0  0  0
 18 35  1  0  0  0  0
 17 34  1  0  0  0  0
 21 37  1  0  0  0  0
 25 39  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
M  END

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    3.6911   -3.4104   -0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512   -2.0751   -0.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -1.0884   -0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8314   -1.3096   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -0.2421   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.5463   -0.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    0.4804   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9831    1.7780    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4592    2.1363    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726    3.2762    0.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309    1.0483   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    1.2799   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347    2.5366    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    0.2211   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2015    0.4712   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1024    2.7281    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682    4.1177    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667    4.9707    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183    4.4497    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630    3.0779    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6962    2.5791    1.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    2.2205    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.8804    0.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453    0.0349   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8661   -1.2794    0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -3.7496    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -3.5102   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685   -4.0544   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -2.3034   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936    3.1671    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035    0.2973    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4441    1.4946   -0.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -0.1841   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    4.5730   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9381    6.0456    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    5.1066    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5818    1.6128    1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021   -0.0139   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -1.3306    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
  8  7  2  0
 14  3  2  0
 14 12  1  0
  3  4  1  0
 11  9  1  0
  8 16  1  0
  7 24  1  0
 24 23  1  0
 23 22  1  0
 16 22  2  0
  5  6  1  0
  6  7  1  0
  8  9  1  0
  4  5  2  0
  9 10  2  0
 11 12  2  0
 16 17  1  0
 22 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 12 13  1  0
 20 21  1  0
 11  5  1  0
 24 25  1  0
  3  2  1  0
  2  1  1  0
  4 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 24 38  1  0
 19 36  1  0
 18 35  1  0
 17 34  1  0
 21 37  1  0
 25 39  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END


  Mrv1652306192119383D          

 39 42  0  0  0  0            999 V2000
    3.6911   -3.4104   -0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512   -2.0751   -0.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -1.0884   -0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8314   -1.3096   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -0.2421   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.5463   -0.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    0.4804   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9831    1.7780    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4592    2.1363    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726    3.2762    0.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309    1.0483   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    1.2799   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347    2.5366    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    0.2211   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2015    0.4712   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1024    2.7281    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682    4.1177    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667    4.9707    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183    4.4497    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630    3.0779    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6962    2.5791    1.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    2.2205    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.8804    0.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453    0.0349   -0.0398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8661   -1.2794    0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -3.7496    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -3.5102   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685   -4.0544   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -2.3034   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936    3.1671    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035    0.2973    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4441    1.4946   -0.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -0.1841   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    4.5730   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9381    6.0456    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    5.1066    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5818    1.6128    1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021   -0.0139   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -1.3306    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
  8  7  2  0  0  0  0
 14  3  2  0  0  0  0
 14 12  1  0  0  0  0
  3  4  1  0  0  0  0
 11  9  1  0  0  0  0
  8 16  1  0  0  0  0
  7 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  1  0  0  0  0
 16 22  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  4  5  2  0  0  0  0
  9 10  2  0  0  0  0
 11 12  2  0  0  0  0
 16 17  1  0  0  0  0
 22 20  1  0  0  0  0
 20 19  2  0  0  0  0
 19 18  1  0  0  0  0
 18 17  2  0  0  0  0
 12 13  1  0  0  0  0
 20 21  1  0  0  0  0
 11  5  1  0  0  0  0
 24 25  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  4 29  1  0  0  0  0
 13 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 24 38  1  0  0  0  0
 19 36  1  0  0  0  0
 18 35  1  0  0  0  0
 17 34  1  0  0  0  0
 21 37  1  0  0  0  0
 25 39  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C2=C1O[C@]([H])(O[H])C1=C2C(=O)C2=C(O[H])C(=C(OC([H])([H])[H])C([H])=C2O1)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O7/c1-7-10(23-2)6-11-13(14(7)20)15(21)12-8-4-3-5-9(19)16(8)25-18(22)17(12)24-11/h3-6,18-20,22H,1-2H3/t18-/m0/s1

> <INCHI_KEY>
HTLOGFXLFFWJOX-SFHVURJKSA-N

> <FORMULA>
C18H14O7

> <MOLECULAR_WEIGHT>
342.303

> <EXACT_MASS>
342.073952791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.22164949440277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6S)-4,6,11-trihydroxy-9-methoxy-10-methyl-6,12-dihydro-5,7-dioxatetraphen-12-one

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.8880324396666666

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.110287703747362

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.671020554985198

> <JCHEM_PKA_STRONGEST_BASIC>
-4.597863826058446

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
87.801

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-4,6,11-trihydroxy-9-methoxy-10-methyl-6H-5,7-dioxatetraphen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    3.6911   -3.4104   -0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512   -2.0751   -0.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -1.0884   -0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8314   -1.3096   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -0.2421   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.5463   -0.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    0.4804   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9831    1.7780    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4592    2.1363    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726    3.2762    0.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309    1.0483   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    1.2799   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347    2.5366    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    0.2211   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2015    0.4712   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1024    2.7281    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682    4.1177    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667    4.9707    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183    4.4497    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630    3.0779    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6962    2.5791    1.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    2.2205    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.8804    0.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453    0.0349   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8661   -1.2794    0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -3.7496    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -3.5102   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685   -4.0544   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -2.3034   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936    3.1671    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035    0.2973    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4441    1.4946   -0.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -0.1841   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    4.5730   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9381    6.0456    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    5.1066    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5818    1.6128    1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021   -0.0139   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -1.3306    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
  8  7  2  0
 14  3  2  0
 14 12  1  0
  3  4  1  0
 11  9  1  0
  8 16  1  0
  7 24  1  0
 24 23  1  0
 23 22  1  0
 16 22  2  0
  5  6  1  0
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  8  9  1  0
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  2  1  1  0
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  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.691  -3.410  -0.722  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.151  -2.075  -0.557  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.212  -1.088  -0.404  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.831  -1.310  -0.381  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.950  -0.242  -0.199  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.386  -0.546  -0.184  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.301   0.480  -0.024  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.983   1.778   0.135  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.459   2.136   0.166  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.873   3.276   0.355  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.431   1.048  -0.033  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.813   1.280  -0.052  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.335   2.537   0.131  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.715   0.221  -0.255  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.202   0.471  -0.250  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.102   2.728   0.263  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.968   4.118   0.128  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.067   4.971   0.301  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.318   4.450   0.617  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.463   3.078   0.746  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.696   2.579   1.058  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.377   2.220   0.552  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.627   0.880   0.703  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.745   0.035  -0.040  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.866  -1.279   0.498  0.00  0.00           O+0
HETATM   26  H   UNK     0       3.142  -3.750   0.162  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.086  -3.510  -1.628  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.569  -4.054  -0.835  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.412  -2.303  -0.498  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.594   3.167   0.275  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.604   0.297   0.753  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.444   1.495  -0.553  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.717  -0.184  -0.960  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.010   4.573  -0.114  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.938   6.046   0.196  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.171   5.107   0.763  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.582   1.613   1.141  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.102  -0.014  -1.075  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.236  -1.331   1.234  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3   14    4    2                                                  
CONECT    4    3    5   29                                                  
CONECT    5    6    4   11                                                  
CONECT    6    5    7                                                       
CONECT    7    8   24    6                                                  
CONECT    8    7   16    9                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11    9   12    5                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12   30                                                       
CONECT   14   15    3   12                                                  
CONECT   15   14   31   32   33                                             
CONECT   16    8   22   17                                                  
CONECT   17   16   18   34                                                  
CONECT   18   19   17   35                                                  
CONECT   19   20   18   36                                                  
CONECT   20   22   19   21                                                  
CONECT   21   20   37                                                       
CONECT   22   23   16   20                                                  
CONECT   23   24   22                                                       
CONECT   24    7   23   25   38                                             
CONECT   25   24   39                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30   13                                                            
CONECT   31   15                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   21                                                            
CONECT   38   24                                                            
CONECT   39   25                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

RDKit          3D

39 42  0  0  0  0  0  0  0  0999 V2000
    3.6911   -3.4104   -0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512   -2.0751   -0.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -1.0884   -0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8314   -1.3096   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -0.2421   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.5463   -0.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    0.4804   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9831    1.7780    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4592    2.1363    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726    3.2762    0.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309    1.0483   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    1.2799   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347    2.5366    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    0.2211   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2015    0.4712   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1024    2.7281    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682    4.1177    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667    4.9707    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183    4.4497    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630    3.0779    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6962    2.5791    1.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    2.2205    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.8804    0.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453    0.0349   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8661   -1.2794    0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -3.7496    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -3.5102   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685   -4.0544   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -2.3034   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936    3.1671    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035    0.2973    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4441    1.4946   -0.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -0.1841   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    4.5730   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9381    6.0456    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    5.1066    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5818    1.6128    1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021   -0.0139   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -1.3306    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
  8  7  2  0
 14  3  2  0
 14 12  1  0
  3  4  1  0
 11  9  1  0
  8 16  1  0
  7 24  1  0
 24 23  1  0
 23 22  1  0
 16 22  2  0
  5  6  1  0
  6  7  1  0
  8  9  1  0
  4  5  2  0
  9 10  2  0
 11 12  2  0
 16 17  1  0
 22 20  1  0
 20 19  2  0
 19 18  1  0
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 12 13  1  0
 20 21  1  0
 11  5  1  0
 24 25  1  0
  3  2  1  0
  2  1  1  0
  4 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 24 38  1  0
 19 36  1  0
 18 35  1  0
 17 34  1  0
 21 37  1  0
 25 39  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₄O₇

Average Mass

342.3030 Da

Monoisotopic Mass

342.07395 Da

IUPAC Name

(6S)-4,6,11-trihydroxy-9-methoxy-10-methyl-6,12-dihydro-5,7-dioxatetraphen-12-one

Traditional Name

(6S)-4,6,11-trihydroxy-9-methoxy-10-methyl-6H-5,7-dioxatetraphen-12-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C([H])C2=C1O[C@]([H])(O[H])C1=C2C(=O)C2=C(O[H])C(=C(OC([H])([H])[H])C([H])=C2O1)C([H])([H])[H]

InChI Identifier

InChI=1S/C18H14O7/c1-7-10(23-2)6-11-13(14(7)20)15(21)12-8-4-3-5-9(19)16(8)25-18(22)17(12)24-11/h3-6,18-20,22H,1-2H3/t18-/m0/s1

InChI Key

HTLOGFXLFFWJOX-SFHVURJKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Mirabilis jalapa	JEOL database	Yang, S.-W., et al, J. Nat. Prod. 64, 313 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

Alternative Parents

Substituents

Rotenone or derivatives
Isoflavone
Chromone
1-benzopyran
Benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organic oxide
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	2.22	ALOGPS
logP	2.89	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.8 m³·mol⁻¹	ChemAxon
Polarizability	34.22 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

124314224

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang, S.-W., et al. (2001). Yang, S.-W., et al, J. Nat. Prod. 64, 313 (2001). J. Nat. Prod..

Showing NP-Card for 9-O-methyl-4-hydroxyboeravinone B (NP0025538)

MOL for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

3D MOL for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

3D SDF for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

3D-SDF for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

PDB for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

3D PDB for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

SMILES for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

INCHI for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

Structure for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)

3D Structure for NP0025538 (9-O-methyl-4-hydroxyboeravinone B)