NP-MRD: Showing NP-Card for Murraol (NP0139682)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-06-29 20:05:42 UTC

Updated at

2022-06-29 20:05:42 UTC

NP-MRD ID

NP0139682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Murraol

Description

Murraol belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Murraol is found in Murraya exotica and Murraya paniculata. Murraol was first documented in 2006 (PMID: 16854718). Based on a literature review very few articles have been published on Murraol (PMID: 28671568).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.1194    3.9919   -0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597    2.7109   -0.3019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    1.5584   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237    1.5156   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4627    0.3630   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924   -0.8077   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -1.9656   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9375   -3.1552   -0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768   -3.0979    0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9981   -4.1927    0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9044   -1.9856    0.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172   -0.8158   -0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105    0.3535   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084    0.3935    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4776   -0.6006    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9436   -0.4497    0.8318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896   -1.6942    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215    0.7346    0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1053   -0.2201    2.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    4.5574   -1.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309    4.0418   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    4.5675    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2765    2.4346   -0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5222    0.3590   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6129   -1.9548   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644   -4.0787    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2339    1.3833    0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1150   -1.5995    0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8584   -2.3756    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093   -1.4825    0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441   -2.3145   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305    0.6567    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087    0.7328   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2284    1.6918    0.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1153    0.7445    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 13 12  1  0
 12  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
 11 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
  7 25  1  0
  8 26  1  0
  5 24  1  0
  4 23  1  0
M  END


  Mrv1652306292222052D          

 19 20  0  0  0  0            999 V2000
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(\C=C\C(C)(C)O)C2=C(C=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-15(2,17)9-8-11-12(18-3)6-4-10-5-7-13(16)19-14(10)11/h4-9,17H,1-3H3/b9-8+

> <INCHI_KEY>
MDKAWXCQYALXRL-CMDGGOBGSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.289

> <EXACT_MASS>
260.104858995

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.471861331779127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.1654059486666664

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.007336920170651

> <JCHEM_PKA_STRONGEST_BASIC>
-2.795590831117357

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
74.2033

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   19                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
CONECT   17    7   18                                                       
CONECT   18   17                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₄

Average Mass

260.2890 Da

Monoisotopic Mass

260.10486 Da

IUPAC Name

8-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-7-methoxy-2H-chromen-2-one

Traditional Name

8-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-7-methoxychromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(\C=C\C(C)(C)O)C2=C(C=CC(=O)O2)C=C1

InChI Identifier

InChI=1S/C15H16O4/c1-15(2,17)9-8-11-12(18-3)6-4-10-5-7-13(16)19-14(10)11/h4-9,17H,1-3H3/b9-8+

InChI Key

MDKAWXCQYALXRL-CMDGGOBGSA-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
Murraya exotica	LOTUS Database	35616633
Murraya paniculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
Cinnamyl alcohol
1-benzopyran
Anisole
Phenol ether
Styrene
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	2.55	ALOGPS
logP	2.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.2 m³·mol⁻¹	ChemAxon
Polarizability	27.47 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

C00051672

Chemspider ID

28424333

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15593213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tan N, Yazici-Tutunis S, Bilgin M, Tan E, Miski M: Antibacterial Activities of Pyrenylated Coumarins from the Roots of Prangos hulusii. Molecules. 2017 Jul 1;22(7):1098. doi: 10.3390/molecules22071098. [PubMed:28671568 ]
Riviere C, Goossens L, Pommery N, Fourneau C, Delelis A, Henichart JP: Antiproliferative effects of isopentenylated coumarins isolated from Phellolophium madagascariense Baker. Nat Prod Res. 2006 Aug;20(10):909-16. doi: 10.1080/14786410500277787. [PubMed:16854718 ]

Showing NP-Card for Murraol (NP0139682)

MOL for NP0139682 (Murraol)

3D MOL for NP0139682 (Murraol)

3D SDF for NP0139682 (Murraol)

3D-SDF for NP0139682 (Murraol)

PDB for NP0139682 (Murraol)

3D PDB for NP0139682 (Murraol)

SMILES for NP0139682 (Murraol)

INCHI for NP0139682 (Murraol)

Structure for NP0139682 (Murraol)

3D Structure for NP0139682 (Murraol)