NP-MRD: Showing NP-Card for Casegravol (NP0139558)

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Record Information

Version

2.0

Created at

2022-06-29 19:59:59 UTC

Updated at

2022-06-29 19:59:59 UTC

NP-MRD ID

NP0139558

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Casegravol

Description

Casegravol 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). Casegravol is found in Casearia graveolens, Citrus sulcata and Murraya exotica. Casegravol was first documented in 2004 (PMID: 15305045). Based on a literature review very few articles have been published on Casegravol (PMID: 24218965).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.7950   -3.6683    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3275   -2.3904    0.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080   -1.3590    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613   -1.6644    0.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4790   -0.6550    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0412    0.6104   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9516    1.6392   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625    2.8854   -0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078    3.1141   -0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    4.2709   -0.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900    2.1134   -0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    0.8898   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7448   -0.1025    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488    0.2549   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868   -0.5186   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0624    0.0109   -0.2359 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2118    0.4021   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   -0.9019    0.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2527    1.2493    0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1262    0.9736    1.9689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871   -4.3127    1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961   -3.6546    1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436   -4.1059    0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973   -2.6499    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386   -0.8186    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9914    1.4103   -0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1476    3.6978   -0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    1.2984   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -1.5304    0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402    0.9135   -2.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0933    1.0683   -1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563   -0.5325   -2.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8027   -1.8389   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180    1.5853    0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186    2.0921    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016    0.2238    2.1904 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  1
 16 19  1  0
 19 20  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 21  1  0
  1 22  1  0
  1 23  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
  7 26  1  0
  8 27  1  0
  5 25  1  0
  4 24  1  0
M  END


  Mrv1652306292222002D          

 20 21  0  0  0  0            999 V2000
    1.5395    2.0625    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
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
   -0.1105    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
  3  4  1  0  0  0  0
  2  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139558

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-15(18,9-16)8-7-11-12(19-2)5-3-10-4-6-13(17)20-14(10)11/h3-8,16,18H,9H2,1-2H3/b8-7+

> <INCHI_KEY>
XVVRFNCLKCYMPH-BQYQJAHWSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.37170200092138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(1E)-3,4-dihydroxy-3-methylbut-1-en-1-yl]-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.1184959820000002

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.31725649188106

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.766981236754443

> <JCHEM_PKA_STRONGEST_BASIC>
-3.087108720925068

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
75.74700000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(1E)-3,4-dihydroxy-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       2.874   3.850   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       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.206   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5   20                                             
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11                                                       
CONECT   18    8   19                                                       
CONECT   19   18                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₅

Average Mass

276.2880 Da

Monoisotopic Mass

276.09977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H16O5/c1-15(18,9-16)8-7-11-12(19-2)5-3-10-4-6-13(17)20-14(10)11/h3-8,16,18H,9H2,1-2H3/b8-7+

InChI Key

XVVRFNCLKCYMPH-BQYQJAHWSA-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
Casearia graveolens	LOTUS Database	35616633
Citrus sulcata	LOTUS Database	35616633
Murraya exotica	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
Benzenoid
Pyran
Heteroaromatic compound
Tertiary alcohol
1,2-diol
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00019810

Chemspider ID

4944779

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440521

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang S, Luo XM, Wang JH: [Study on the chemical constituents from ethyl acetate extract of Micromelum falcatum]. Zhong Yao Cai. 2013 May;36(5):744-6. [PubMed:24218965 ]
Chaya N, Terauchi K, Yamagata Y, Kinjo J, Okabe H: Antiproliferative constituents in plants 14. Coumarins and acridone alkaloids from Boenninghausenia japonica NAKAI. Biol Pharm Bull. 2004 Aug;27(8):1312-6. doi: 10.1248/bpb.27.1312. [PubMed:15305045 ]

Showing NP-Card for Casegravol (NP0139558)

MOL for NP0139558 (Casegravol)

3D MOL for NP0139558 (Casegravol)

3D SDF for NP0139558 (Casegravol)

3D-SDF for NP0139558 (Casegravol)

PDB for NP0139558 (Casegravol)

3D PDB for NP0139558 (Casegravol)

SMILES for NP0139558 (Casegravol)

INCHI for NP0139558 (Casegravol)

Structure for NP0139558 (Casegravol)

3D Structure for NP0139558 (Casegravol)