NP-MRD: Showing NP-Card for (12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone (NP0062329)

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Record Information

Version

2.0

Created at

2022-04-28 07:00:59 UTC

Updated at

2022-04-28 07:00:59 UTC

NP-MRD ID

NP0062329

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone

Description

Dalcochinin 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. (12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone is found in Dalbergia cochinchinensis. (12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone was first documented in 2006 (PMID: 16289258). Based on a literature review a small amount of articles have been published on dalcochinin (PMID: 18463895) (PMID: 17998137).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209012D          

 30 34  0  0  1  0            999 V2000
    5.3202    0.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7218    1.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2984    2.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    0.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    0.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688    0.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455    0.7772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2470    1.4978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8237    2.2060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9988    2.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5972    1.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.7646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723    1.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3490    2.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755    2.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553    1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5290    1.1628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2297    0.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371    0.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2246   -0.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659    0.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2253    2.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000    2.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2767    3.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5467    1.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9483    2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  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  5  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  1  0  0  0
 13 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
 12 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 20 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 26  1  6  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -7.2955   -1.6031    0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2821   -0.7219    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3695    0.5515   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2461    1.6634    0.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0759   -1.0907    0.8197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8319   -1.1759   -0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8327   -0.3236    0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.3300    1.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7487    1.1919    2.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902    1.3856    2.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667    0.7048    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4902   -0.1568    0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -0.8193   -0.6937 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5469   -1.0201   -0.6938 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8507   -1.9881    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550   -1.7856    0.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0764   -0.9483    0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363   -1.1405    0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3199   -0.2740   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6688   -0.5340   -0.0638 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1698   -1.6312    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8782    0.8242   -0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7653    1.7067   -1.5089 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2323    2.8093   -2.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5139    1.0169   -0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251    0.1480   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533    0.3488   -0.4179 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6891    0.9232    0.8758 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8504    2.3262    0.8118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141   -0.0173    1.7103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2677   -2.5246    0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1752   -1.3613   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3755    0.6033   -1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6122    0.5871   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086    1.9662    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2122   -2.0483    1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -2.2180   -0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0662   -0.8086   -1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604    1.7509    3.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982    2.0582    2.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -1.3585   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7774   -3.0154    0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813   -1.9239    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688   -2.0080    0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2257   -1.7780    0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0709   -1.4212    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6440   -2.5833    0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0538    3.3718   -2.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4524    2.5054   -2.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6914    3.4474   -1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1262    1.8831   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    0.9995   -1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2611    0.5364    1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    2.6396    0.2243 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 14  1  0
 14 15  1  0
 15 16  1  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5 30  1  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 11 28  1  0
 28 29  1  0
 22 19  1  0
 28 27  1  0
 16 17  1  0
  7 12  1  0
 30  8  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 18 44  1  0
 25 51  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 27 52  1  6
 14 41  1  6
 15 42  1  0
 15 43  1  0
 10 40  1  0
  9 39  1  0
  6 37  1  0
  6 38  1  0
  5 36  1  1
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
 28 53  1  1
 29 54  1  0
M  END


  Mrv1652304282209012D          

 30 34  0  0  1  0            999 V2000
    5.3202    0.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7218    1.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2984    2.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    0.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    0.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688    0.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455    0.7772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2470    1.4978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8237    2.2060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9988    2.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5972    1.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.7646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723    1.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3490    2.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755    2.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553    1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5290    1.1628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2297    0.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371    0.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2246   -0.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659    0.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2253    2.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000    2.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2767    3.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5467    1.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9483    2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  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  5  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  1  0  0  0
 13 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
 12 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 20 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 26  1  6  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062329

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@H]1[C@@H](CO2)OC2=C(C=CC3=C2C[C@@H](O3)C(=C)CO)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O7/c1-11(9-24)16-7-14-15(29-16)5-4-12-22(25)21-13-6-18(26-2)19(27-3)8-17(13)28-10-20(21)30-23(12)14/h4-6,8,16,20-22,24-25H,1,7,9-10H2,2-3H3/t16-,20-,21+,22+/m1/s1

> <INCHI_KEY>
MMPZIMLLXOEISC-XXMUNEJQSA-N

> <FORMULA>
C23H24O7

> <MOLECULAR_WEIGHT>
412.438

> <EXACT_MASS>
412.152203113

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.39394618177793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6R,12R,13R)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14(19),15,17-hexaen-12-ol

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
1.6606067593333338

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.1207733496806

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.758789240395231

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7548247495515525

> <JCHEM_POLAR_SURFACE_AREA>
86.61000000000001

> <JCHEM_REFRACTIVITY>
108.16829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R,12R,13R)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14(19),15,17-hexaen-12-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.931   1.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.681   2.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.890   4.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.351   4.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.601   2.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.391   1.498   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.642   0.152   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.102   0.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.312   1.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.061   2.796   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.271   4.118   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.731   4.094   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.982   2.749   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.772   1.427   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.442   2.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.651   4.048   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.401   5.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.941   5.416   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.850   3.704   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.987   2.171   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.429   1.566   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.309   1.380   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.286  -0.159   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.655   2.130   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.976   1.340   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.021   5.463   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.640   5.533   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.850   6.855   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.220   2.890   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.970   4.235   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   29                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   26                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16   21                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   15                                                       
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   11                                                            
CONECT   27    3   28                                                       
CONECT   28   27                                                            
CONECT   29    2   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₄O₇

Average Mass

412.4380 Da

Monoisotopic Mass

412.15220 Da

IUPAC Name

(1S,6R,12R,13R)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14(19),15,17-hexaen-12-ol

Traditional Name

(1S,6R,12R,13R)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14(19),15,17-hexaen-12-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@H]1[C@@H](CO2)OC2=C(C=CC3=C2C[C@@H](O3)C(=C)CO)[C@@H]1O

InChI Identifier

InChI=1S/C23H24O7/c1-11(9-24)16-7-14-15(29-16)5-4-12-22(25)21-13-6-18(26-2)19(27-3)8-17(13)28-10-20(21)30-23(12)14/h4-6,8,16,20-22,24-25H,1,7,9-10H2,2-3H3/t16-,20-,21+,22+/m1/s1

InChI Key

MMPZIMLLXOEISC-XXMUNEJQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Dalbergia cochinchinensis	Plant	KNApSAcK

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
Isoflavan
Chromane
Benzopyran
1-benzopyran
Coumaran
Anisole
Alkyl aryl ether
Benzenoid
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
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	2.36	ALOGPS
logP	1.66	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.76	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.17 m³·mol⁻¹	ChemAxon
Polarizability	43.39 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

C00018877

Chemspider ID

58829972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25203053

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Arthan D, Sithiprom S, Thima K, Limmatvatirat C, Chavalitshewinkoon-Petmitr P, Svasti J: Inhibitory effects of Thai plants beta-glycosides on Trichomonas vaginalis. Parasitol Res. 2008 Jul;103(2):443-8. doi: 10.1007/s00436-008-0996-2. Epub 2008 May 8. [PubMed:18463895 ]
Chuankhayan P, Rimlumduan T, Tantanuch W, Mothong N, Kongsaeree PT, Metheenukul P, Svasti J, Jensen ON, Cairns JR: Functional and structural differences between isoflavonoid beta-glycosidases from Dalbergia sp. Arch Biochem Biophys. 2007 Dec 15;468(2):205-16. doi: 10.1016/j.abb.2007.09.015. Epub 2007 Oct 11. [PubMed:17998137 ]
Arthan D, Kittakoop P, Esen A, Svasti J: Furostanol glycoside 26-O-beta-glucosidase from the leaves of Solanum torvum. Phytochemistry. 2006 Jan;67(1):27-33. doi: 10.1016/j.phytochem.2005.09.035. Epub 2005 Nov 11. [PubMed:16289258 ]

Showing NP-Card for (12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone (NP0062329)

MOL for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

3D MOL for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

3D SDF for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

3D-SDF for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

PDB for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

3D PDB for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

SMILES for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

INCHI for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

Structure for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)

3D Structure for NP0062329 ((12R)-12-Hydroxy-2,3-dimethoxy-5'-(1''-hydroxymethylethenyl)4',5'-dihydrofurano[2',3':9,8]rotenone)