NP-MRD: Showing NP-Card for 13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one (NP0301527)

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Record Information

Version

2.0

Created at

2022-09-10 14:33:26 UTC

Updated at

2022-09-10 14:33:26 UTC

NP-MRD ID

NP0301527

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

Description

Dalbinol 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. Thus, dalbinol is considered to be a flavonoid lipid molecule. 13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one is found in Amorpha fruticosa, Berchemia discolor and Dalbergia monetaria. Dalbinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171513332D          

 31 35  0  0  0  0            999 V2000
    1.5210   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739   -1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755   -0.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6238   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4487   -1.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8720   -2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6969   -1.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9245   -2.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1202   -2.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   -3.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8937   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2439   -3.4662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -2.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3973   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -3.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9443   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7063   -1.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4270   -1.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1351   -1.2574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  5 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    7.0782    1.3972    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0471    0.6476    0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0248   -0.8220    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2396   -1.2161    1.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8738    1.3272   -0.2426 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6574    1.0786    0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7247    0.3669   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3548    0.2279   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6900   -0.4126   -2.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4218   -0.8913   -2.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -0.7455   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4563   -0.1153   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7830    0.0021    1.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6192    0.1985    1.1223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1804    0.1263    2.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5484   -0.2596    2.5151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087   -0.1781    1.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6093    0.2073    1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3342    0.2800    0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6730    0.6764    0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2777    1.0074    1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.0555   -1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3990    0.0141   -2.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468   -0.3299   -3.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3460   -0.4552   -1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -0.5165    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2572   -0.9174    0.2878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1622   -2.0586    1.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5212   -1.2408   -0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348   -1.9825   -1.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6205    0.7898   -1.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9689    0.9758    1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0823    2.4699    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1940   -1.1331    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9729   -1.3504   -0.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165   -1.3263    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0743    2.4142   -0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912    0.4214    1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1972    2.0177    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1580   -0.5305   -3.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9234   -1.3873   -3.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438    1.1597    0.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5999   -0.5161    3.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612    1.1603    2.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1088    0.4684    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3648    1.1423    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8196    1.9131    1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1307    0.1874    2.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4578   -0.3559   -4.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2623   -1.3262   -3.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9645    0.4212   -3.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9030   -0.6966   -1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791   -2.2790    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 26  2  0
 26 25  1  0
 25 22  2  0
 22 23  1  0
 23 24  1  0
 26 27  1  0
 27 28  1  1
 27 14  1  0
 14 15  1  0
 15 16  1  0
 14 13  1  0
 13 12  1  0
 12  7  2  0
  7  6  1  0
  6  5  1  0
  5 31  1  0
 31  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 29  1  0
 29 30  2  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 22 19  1  0
 29 27  1  0
 16 17  1  0
 11 12  1  0
  8  7  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 18 45  1  0
 25 52  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 28 53  1  0
 14 42  1  6
 15 43  1  0
 15 44  1  0
  6 38  1  0
  6 39  1  0
  5 37  1  6
  9 40  1  0
 10 41  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
M  END


  Mrv1533004171513332D          

 31 35  0  0  0  0            999 V2000
    1.5210   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739   -1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755   -0.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6238   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4487   -1.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8720   -2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6969   -1.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9245   -2.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1202   -2.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   -3.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8937   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2439   -3.4662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -2.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3973   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -3.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9443   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7063   -1.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4270   -1.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1351   -1.2574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  5 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)C1(O)C(CO2)OC2=C3CC(OC3=CC=C2C1=O)C(=C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O8/c1-11(9-24)16-6-13-15(30-16)5-4-12-21(13)31-20-10-29-17-8-19(28-3)18(27-2)7-14(17)23(20,26)22(12)25/h4-5,7-8,16,20,24,26H,1,6,9-10H2,2-3H3

> <INCHI_KEY>
MYQAATJJIDGOMQ-UHFFFAOYSA-N

> <FORMULA>
C23H22O8

> <MOLECULAR_WEIGHT>
426.421

> <EXACT_MASS>
426.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.61399038685978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-12-one

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
1.4478889946666667

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.10057880930352

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.07522215967843

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7548247500442145

> <JCHEM_POLAR_SURFACE_AREA>
103.68

> <JCHEM_REFRACTIVITY>
108.73299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dalbinol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.839  -5.242   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.589  -3.897   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.129  -3.873   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.878  -2.528   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.418  -2.505   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.168  -1.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.707  -1.136   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.498  -2.458   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.037  -2.435   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.828  -3.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.368  -3.733   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.380  -2.573   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.797  -3.178   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.659  -4.712   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.158  -5.055   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.408  -6.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.868  -6.423   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.078  -5.102   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.538  -5.125   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.789  -6.470   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.748  -3.803   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.998  -5.148   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.208  -3.827   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.459  -5.172   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.919  -5.195   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.169  -6.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.629  -6.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.118  -2.388   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.095  -0.848   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.464  -3.137   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      20.786  -2.347   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    8   22   23                                             
CONECT   22   21                                                            
CONECT   23   21    5   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    3   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   13   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₈

Average Mass

426.4210 Da

Monoisotopic Mass

426.13147 Da

IUPAC Name

13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-12-one

Traditional Name

dalbinol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)C1(O)C(CO2)OC2=C3CC(OC3=CC=C2C1=O)C(=C)CO

InChI Identifier

InChI=1S/C23H22O8/c1-11(9-24)16-6-13-15(30-16)5-4-12-21(13)31-20-10-29-17-8-19(28-3)18(27-2)7-14(17)23(20,26)22(12)25/h4-5,7-8,16,20,24,26H,1,6,9-10H2,2-3H3

InChI Key

MYQAATJJIDGOMQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Amorpha fruticosa	LOTUS Database	35616633
Berchemia discolor	LOTUS Database	35616633
Dalbergia monetaria	LOTUS Database	35616633

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
8-prenylated isoflavanone
Isoflavanone
Isoflavan
Chromone
Chromane
Benzopyran
1-benzopyran
Coumaran
Aryl alkyl ketone
Anisole
Aryl ketone
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Rotenoid flavonoids (LMPK12060040 )

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	1.61	ALOGPS
logP	1.45	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.08	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.73 m³·mol⁻¹	ChemAxon
Polarizability	43.61 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

44257412

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one (NP0301527)

MOL for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D MOL for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D SDF for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D-SDF for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

PDB for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D PDB for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

SMILES for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

INCHI for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

Structure for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)

3D Structure for NP0301527 (13-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one)