NP-MRD: Showing NP-Card for 8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate (NP0228581)

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Record Information

Version

2.0

Created at

2022-09-06 08:17:42 UTC

Updated at

2022-09-06 08:17:42 UTC

NP-MRD ID

NP0228581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate

Description

14-Hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-9-methoxy-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadeca-1,7,9,11,13,15-hexaen-3-yl acetate belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. 8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate is found in Bletilla striata and Pleione bulbocodioides. 14-Hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-9-methoxy-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadeca-1,7,9,11,13,15-hexaen-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121516332D          

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M  END

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M  END


  Mrv0541 04121516332D          

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 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1COC2=CC(OC)=C3C(CCC4=CC(O)=CC=C34)=C2C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O8/c1-14(29)36-28-20(16-10-23(33-3)27(31)24(11-16)34-4)13-35-22-12-21(32-2)25-18-8-6-17(30)9-15(18)5-7-19(25)26(22)28/h6,8-12,20,28,30-31H,5,7,13H2,1-4H3

> <INCHI_KEY>
ICFCQLYGQGOROO-UHFFFAOYSA-N

> <FORMULA>
C28H28O8

> <MOLECULAR_WEIGHT>
492.524

> <EXACT_MASS>
492.178417862

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.799704218588666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-9-methoxy-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15-hexaen-3-yl acetate

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
4.180877388666665

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.980333265183281

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.2210479754309

> <JCHEM_PKA_STRONGEST_BASIC>
-4.281733516320988

> <JCHEM_POLAR_SURFACE_AREA>
103.68

> <JCHEM_REFRACTIVITY>
132.33439999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-9-methoxy-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15-hexaen-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       3.644   3.717   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.652   2.553   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.148   1.098   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.156  -0.067   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.652  -1.522   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.140  -1.813   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.132  -0.649   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.619  -0.940   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.115  -2.395   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.636   0.807   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.628   1.971   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.164  -5.305   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.685  -6.178   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.197  -5.887   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.205  -7.051   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.701  -8.507   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.750  -3.268   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.677  -0.940   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668   0.224   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.274   0.878   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.172   1.680   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   30                                                  
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   20   24                                                  
CONECT   31   21   15   32                                                  
CONECT   32   31   12   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
14-Hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-9-methoxy-6-oxatetracyclo[8.8.0.0,.0,]octadeca-1,7,9,11,13,15-hexaen-3-yl acetic acid	Generator
14-Hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-9-methoxy-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15-hexaen-3-yl acetic acid	Generator

Chemical Formula

C₂₈H₂₈O₈

Average Mass

492.5240 Da

Monoisotopic Mass

492.17842 Da

IUPAC Name

14-hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-9-methoxy-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15-hexaen-3-yl acetate

Traditional Name

14-hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-9-methoxy-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15-hexaen-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C1COC2=CC(OC)=C3C(CCC4=CC(O)=CC=C34)=C2C1OC(C)=O

InChI Identifier

InChI=1S/C28H28O8/c1-14(29)36-28-20(16-10-23(33-3)27(31)24(11-16)34-4)13-35-22-12-21(32-2)25-18-8-6-17(30)9-15(18)5-7-19(25)26(22)28/h6,8-12,20,28,30-31H,5,7,13H2,1-4H3

InChI Key

ICFCQLYGQGOROO-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
Bletilla striata	LOTUS Database	35616633
Pleione bulbocodioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylated isoflavonoids

Alternative Parents

Substituents

3p-methoxyisoflavonoid-skeleton
7-methoxyisoflavonoid-skeleton
Isoflavanol
Isoflavan
Naphthopyran
Phenanthrene
Methoxyphenol
Benzopyran
Naphthalene
Chromane
1-benzopyran
Dimethoxybenzene
M-dimethoxybenzene
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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	4.11	ALOGPS
logP	4.18	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	9.22	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.33 m³·mol⁻¹	ChemAxon
Polarizability	51.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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 8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate (NP0228581)

MOL for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

3D MOL for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

3D SDF for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

3D-SDF for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

PDB for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

3D PDB for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

SMILES for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

INCHI for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

Structure for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)

3D Structure for NP0228581 (8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate)