NP-MRD: Showing NP-Card for (S)-4'-Hydroxy-4-methoxydalbergione (NP0057206)

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Record Information

Version

2.0

Created at

2022-04-28 02:42:33 UTC

Updated at

2022-04-28 02:42:33 UTC

NP-MRD ID

NP0057206

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-4'-Hydroxy-4-methoxydalbergione

Description

(S)-4'-hydroxy-4-methoxydalbergione belongs to the class of organic compounds known as dalbergiones. These are quinone derivatives containing a dalbergione moiety, which consists of a 1-4 quinone conjugated to a phenyl group at ring carbon 2. Thus, (S)-4'-hydroxy-4-methoxydalbergione is considered to be a flavonoid. (S)-4'-Hydroxy-4-methoxydalbergione is found in Dalbergia melanoxylon, Dalbergia sissoo and Dalbergia spp.. (S)-4'-Hydroxy-4-methoxydalbergione was first documented in 2005 (PMID: 16242087). Based on a literature review very few articles have been published on (s)-4'-hydroxy-4-methoxydalbergione (PMID: 31826027).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -0.7036   -3.2840   -0.7822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733   -2.2256   -0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073   -0.8376   -1.0073 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4131   -0.6138   -0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2616   -0.2389   -1.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -0.0124   -1.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938    0.3418   -2.3370 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2098   -0.1964   -0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5626    0.0136    0.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0252    1.3376    0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3970   -0.5667    0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9730   -0.7878    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2765   -1.1389    1.5689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    0.0484   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112   -0.4145    0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3512    0.3946    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482    1.6761    1.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882    2.5330    1.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696    2.1822    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475    1.3428   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612   -3.1709   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -4.2577   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5524   -2.3691   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.5620   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   -0.0856   -2.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613    1.8216    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752    1.8584   -0.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0956    1.3126    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924   -0.7023    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3727   -1.4297    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198    0.0148    2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9134    3.0768    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1631    3.2154   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826    1.7243   -1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  6  8  1  0
 20 14  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
  5 25  1  0
  3 24  1  6
  2 23  1  0
  1 21  1  0
  1 22  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv1652304282204422D          

 20 21  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
  1 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057206

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C(=CC1=O)[C@@H](C=C)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-3-12(10-4-6-11(17)7-5-10)13-8-15(19)16(20-2)9-14(13)18/h3-9,12,17H,1H2,2H3/t12-/m0/s1

> <INCHI_KEY>
DLCVFIMWFKVRTM-LBPRGKRZSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.284

> <EXACT_MASS>
270.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.6424678070872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S)-1-(4-hydroxyphenyl)prop-2-en-1-yl]-5-methoxycyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.7162410996666666

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.493029982907647

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9401787359261515

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
77.9751

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S)-1-(4-hydroxyphenyl)prop-2-en-1-yl]-5-methoxycyclohexa-2,5-diene-1,4-dione

> <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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    7   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    1   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2840 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

2-[(1S)-1-(4-hydroxyphenyl)prop-2-en-1-yl]-5-methoxycyclohexa-2,5-diene-1,4-dione

Traditional Name

2-[(1S)-1-(4-hydroxyphenyl)prop-2-en-1-yl]-5-methoxycyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C(=CC1=O)[C@@H](C=C)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O4/c1-3-12(10-4-6-11(17)7-5-10)13-8-15(19)16(20-2)9-14(13)18/h3-9,12,17H,1H2,2H3/t12-/m0/s1

InChI Key

DLCVFIMWFKVRTM-LBPRGKRZSA-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 melanoxylon	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Dalbergia spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dalbergiones. These are quinone derivatives containing a dalbergione moiety, which consists of a 1-4 quinone conjugated to a phenyl group at ring carbon 2.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Dalbergiones

Direct Parent

Dalbergiones

Alternative Parents

Substituents

Dalbergione skeleton
P-benzoquinone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous ester
Ketone
Cyclic ketone
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Neoflavonoids (LMPK12100073 )

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	2.41	ALOGPS
logP	2.72	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.98 m³·mol⁻¹	ChemAxon
Polarizability	27.64 Å³	ChemAxon
Number of Rings	2	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

C00010253

Chemspider ID

21782013

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Moratinos MM, Tevar E, Conde-Salazar L: Contact allergy to a cocobolo bracelet. Dermatitis. 2005 Sep;16(3):139-41. [PubMed:16242087 ]
Pfohler C, Tilgen W: Contact dermatitis of the lips due to late-type sensitization against dalbergiones in a wooden recorder. Allergol Select. 2018 Sep 1;2(1):29-31. doi: 10.5414/ALX01323E. eCollection 2018. [PubMed:31826027 ]

Showing NP-Card for (S)-4'-Hydroxy-4-methoxydalbergione (NP0057206)

MOL for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

3D MOL for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

3D SDF for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

3D-SDF for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

PDB for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

3D PDB for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

SMILES for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

INCHI for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

Structure for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)

3D Structure for NP0057206 ((S)-4'-Hydroxy-4-methoxydalbergione)