NP-MRD: Showing NP-Card for 4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene (NP0051685)

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Record Information

Version

2.0

Created at

2022-04-27 22:57:40 UTC

Updated at

2022-04-27 22:57:40 UTC

NP-MRD ID

NP0051685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene

Description

7-Methoxy-9,10-dihydrophenanthrene-2,5-diol, also known as 4,7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene, belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. 4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene is found in Arundina graminifolia, Bletilla striata , Bulbophyllum odoratissimum, Dendrobium densiflorum, Dendrobium loddigesii, Dendrobium nobile , Dendrobium plicatile, Dioscorea oppositifolia, Eulophia petersii , Luisia indivisa, Nidema boothii, Pholidota chinensis Lindl. , Pleione bulbocodioides, Scaphyglottis livida and Thunia alba. 7-Methoxy-9,10-dihydrophenanthrene-2,5-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.1451    0.3230   -0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2111   -0.7335   -0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -0.4323   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.8751    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598    1.1629    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293    2.4806    0.1833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    0.1186    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5988   -1.1975   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9675   -1.4585   -0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073   -2.3645   -0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829   -2.1460    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1231   -0.7350    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126   -0.4904    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9930    0.7844    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3696    0.9602    0.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1308    1.8457    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397    1.6448    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734    0.3539    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9166    0.8952    0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9580    1.0349   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1787   -0.0195   -0.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755    1.6446    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    3.2175    0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -2.5090   -0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1342   -3.1981    0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -2.6800   -1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3874   -2.7863   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -2.4324    1.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564   -1.3735    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8260    1.8431    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4792    2.8639    0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    2.5080    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 18  2  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  1  0
 14 13  2  0
  8  9  2  0
  9  3  1  0
 18  7  1  0
 13 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 17 32  1  0
 16 31  1  0
 15 30  1  0
 13 29  1  0
  9 24  1  0
M  END


  Mrv1533004251516462D          

 18 20  0  0  0  0            999 V2000
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
  5 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(CCC3=C2C=CC(O)=C3)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c1-18-12-7-10-3-2-9-6-11(16)4-5-13(9)15(10)14(17)8-12/h4-8,16-17H,2-3H2,1H3

> <INCHI_KEY>
RDKDIPDDUFMMMT-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.222459465576907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-9,10-dihydrophenanthrene-2,5-diol

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.418786145

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.176894550836677

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.17298269655167

> <JCHEM_PKA_STRONGEST_BASIC>
-4.834034587212678

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
69.8994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-9,10-dihydrophenanthrene-2,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.414  -1.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15                                                            
CONECT   18    5                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene	ChEBI

Chemical Formula

C₁₅H₁₄O₃

Average Mass

242.2740 Da

Monoisotopic Mass

242.09429 Da

IUPAC Name

7-methoxy-9,10-dihydrophenanthrene-2,5-diol

Traditional Name

7-methoxy-9,10-dihydrophenanthrene-2,5-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(CCC3=C2C=CC(O)=C3)=C1

InChI Identifier

InChI=1S/C15H14O3/c1-18-12-7-10-3-2-9-6-11(16)4-5-13(9)15(10)14(17)8-12/h4-8,16-17H,2-3H2,1H3

InChI Key

RDKDIPDDUFMMMT-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, 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
Arundina graminifolia	LOTUS Database	35616633
Bletilla striata	Plant	KNApSAcK
Bulbophyllum odoratissimum	LOTUS Database	35616633
Dendrobium densiflorum	Plant	KNApSAcK
Dendrobium loddigesii	LOTUS Database	35616633
Dendrobium nobile	Plant	KNApSAcK
Dendrobium plicatile	Plant	KNApSAcK
Dioscorea oppositifolia	LOTUS Database	35616633
Eulophia petersii	Plant	KNApSAcK
Luisia indivisa	Plant	KNApSAcK
Nidema boothii	Plant	KNApSAcK
Pholidota chinensis Lindl.	Plant	KNApSAcK
Pleione bulbocodioides	Plant	KNApSAcK
Scaphyglottis livida	LOTUS Database	35616633
Thunia alba	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Hydrophenanthrenes

Direct Parent

Hydrophenanthrenes

Alternative Parents

Substituents

Hydrophenanthrene
1-naphthol
Naphthalene
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

dihydrophenanthrene (CHEBI:28678 )

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	2.71	ALOGPS
logP	3.42	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.9 m³·mol⁻¹	ChemAxon
Polarizability	26.22 Å³	ChemAxon
Number of Rings	3	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

C00002941

Chemspider ID

Not Available

KEGG Compound ID

C10257

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442702

PDB ID

Not Available

ChEBI ID

28678

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene (NP0051685)

MOL for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

3D MOL for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

3D SDF for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

3D-SDF for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

PDB for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

3D PDB for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

SMILES for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

INCHI for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

Structure for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)

3D Structure for NP0051685 (4,7-Dihydroxy-2-methoxy-9,10-dihydrophenanthrene)