NP-MRD: Showing NP-Card for 6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one (NP0226471)

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Record Information

Version

2.0

Created at

2022-09-06 05:31:10 UTC

Updated at

2022-09-06 05:31:10 UTC

NP-MRD ID

NP0226471

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one

Description

6,11,14-Trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]Docosa-3(12),4(9),10,15,17,19-hexaen-13-one 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. 6,11,14-Trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]Docosa-3(12),4(9),10,15,17,19-hexaen-13-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509372D          

 34 38  0  0  0  0            999 V2000
    6.6513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004241509372D          

 34 38  0  0  0  0            999 V2000
    6.6513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0226471

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(O)C(C)(C)OC2=CC(O)=C3C(=O)C4(O)C(COC5=CC(OC)=C(OC)C=C45)OC3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O10/c1-23(2)22(27)20(31-5)18-15(34-23)7-11(25)17-19(18)33-16-9-32-12-8-14(30-4)13(29-3)6-10(12)24(16,28)21(17)26/h6-8,16,20,22,25,27-28H,9H2,1-5H3

> <INCHI_KEY>
RTUABMSWXKMPKI-UHFFFAOYSA-N

> <FORMULA>
C24H26O10

> <MOLECULAR_WEIGHT>
474.462

> <EXACT_MASS>
474.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.13580113721472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15,17,19-hexaen-13-one

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.8316637723333338

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.095202243651123

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.455888151736051

> <JCHEM_PKA_STRONGEST_BASIC>
-3.731431997231014

> <JCHEM_POLAR_SURFACE_AREA>
133.14000000000001

> <JCHEM_REFRACTIVITY>
116.8025

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15,17,19-hexaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.876  -1.183   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.796  -1.183   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.616  -2.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.616  -4.840   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.566  -5.184   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.876  -6.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.416  -6.517   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.186  -7.851   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.496  -6.517   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.266  -5.184   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.036  -1.183   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      21.656  -3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      22.426  -2.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.116  -6.517   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      19.346  -7.851   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.186  -2.516   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   34                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   33                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   31                                             
CONECT   18   17                                                            
CONECT   19   17   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31                                                       
CONECT   31   30   17   22                                                  
CONECT   32   19   33                                                       
CONECT   33   32   14   34                                                  
CONECT   34   33    3   10                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆O₁₀

Average Mass

474.4620 Da

Monoisotopic Mass

474.15260 Da

IUPAC Name

6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15,17,19-hexaen-13-one

Traditional Name

6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15,17,19-hexaen-13-one

CAS Registry Number

Not Available

SMILES

COC1C(O)C(C)(C)OC2=CC(O)=C3C(=O)C4(O)C(COC5=CC(OC)=C(OC)C=C45)OC3=C12

InChI Identifier

InChI=1S/C24H26O10/c1-23(2)22(27)20(31-5)18-15(34-23)7-11(25)17-19(18)33-16-9-32-12-8-14(30-4)13(29-3)6-10(12)24(16,28)21(17)26/h6-8,16,20,22,25,27-28H,9H2,1-5H3

InChI Key

RTUABMSWXKMPKI-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

Not Available

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
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-benzopyran
Chromane
Benzopyran
Anisole
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.43	ALOGPS
logP	1.83	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	133.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.8 m³·mol⁻¹	ChemAxon
Polarizability	47.14 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one (NP0226471)

MOL for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

3D MOL for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

3D SDF for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

3D-SDF for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

PDB for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

3D PDB for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

SMILES for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

INCHI for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

Structure for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)

3D Structure for NP0226471 (6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,9,11,15(20),16,18-hexaen-13-one)