NP-MRD: Showing NP-Card for (+)-Gynunone (NP0074823)

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Record Information

Version

1.0

Created at

2022-04-28 20:08:55 UTC

Updated at

2022-04-28 20:08:55 UTC

NP-MRD ID

NP0074823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Gynunone

Description

(+)-Gynunone belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure. (+)-Gynunone is found in Gynura elliptica. It was first documented in 2000 (PMID: 10820787). Based on a literature review a significant number of articles have been published on (+)-Gynunone (PMID: 35489815) (PMID: 35489814) (PMID: 35489813) (PMID: 35489812).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    5.1111    0.3693    0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.7682    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6955    1.7853    1.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4812    0.2033    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7873    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446    0.3422    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1229   -0.7303   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9897   -1.3234   -0.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994   -0.8751   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3293   -1.5455   -1.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5040   -0.9913   -0.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.5097    0.7517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4886    0.0324    0.5046 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3550   -0.8979   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1746    1.3177   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752    1.6488    0.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3297    0.7787    0.9275 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3761   -0.6381    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695    1.0299    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3663    0.4870   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    1.6561    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841   -2.1756   -1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2649   -1.4369   -1.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268   -1.1925    1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9121    0.2952    1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4024   -0.8466    0.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0178   -1.9530   -0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3419   -0.7383   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9069    2.1270    0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2667    1.0829   -1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590    1.1430    1.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 12  1  0
 12 11  1  0
 11  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9  4  2  0
  4  5  1  0
  5  6  2  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 12 13  1  0
  6  7  1  0
  6 17  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 13 25  1  1
 15 29  1  0
 15 30  1  0
 17 31  1  1
 12 24  1  1
  8 22  1  0
 10 23  1  0
  5 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
M  END


  Mrv1652304282222082D          

 17 19  0  0  1  0            999 V2000
    4.3402    2.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1008    2.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973    1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333    2.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727    3.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762    3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959    3.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.2280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9085    2.4486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2507    1.9506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739    2.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133    3.2118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3153    3.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4682    1.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4253    0.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436    3.0270    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  1  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  1 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CO[C@H]2[C@@H]1OC1=CC(O)=C(C=C21)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O4/c1-6-5-16-13-9-3-8(7(2)14)10(15)4-11(9)17-12(6)13/h3-4,6,12-13,15H,5H2,1-2H3/t6-,12-,13-/m1/s1

> <INCHI_KEY>
CVBFRNFTZXHUAN-AJJMPYILSA-N

> <FORMULA>
C13H14O4

> <MOLECULAR_WEIGHT>
234.251

> <EXACT_MASS>
234.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.168838933650196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2R,5R,6R)-10-hydroxy-5-methyl-3,7-dioxatricyclo[6.4.0.0^{2,6}]dodeca-1(12),8,10-trien-11-yl]ethan-1-one

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
1.9112010353333337

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.550537588272476

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.976564600024304

> <JCHEM_PKA_STRONGEST_BASIC>
-4.121704206831646

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
61.156200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,5R,6R)-10-hydroxy-5-methyl-3,7-dioxatricyclo[6.4.0.0^{2,6}]dodeca-1(12),8,10-trien-11-yl]ethanone

> <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       8.102   5.301   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.655   3.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.155   3.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.102   4.601   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.549   6.075   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.049   6.425   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.286   6.955   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.058   6.026   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.562   4.571   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.335   3.641   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.071   4.522   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.518   5.995   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.589   7.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.708   2.703   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.207   3.053   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.261   1.229   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.601   5.650   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    1                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄O₄

Average Mass

234.2510 Da

Monoisotopic Mass

234.08921 Da

IUPAC Name

1-[(2R,5R,6R)-10-hydroxy-5-methyl-3,7-dioxatricyclo[6.4.0.0^{2,6}]dodeca-1(12),8,10-trien-11-yl]ethan-1-one

Traditional Name

1-[(2R,5R,6R)-10-hydroxy-5-methyl-3,7-dioxatricyclo[6.4.0.0^{2,6}]dodeca-1(12),8,10-trien-11-yl]ethanone

CAS Registry Number

Not Available

SMILES

C[C@@H]1CO[C@H]2[C@@H]1OC1=CC(O)=C(C=C21)C(C)=O

InChI Identifier

InChI=1S/C13H14O4/c1-6-5-16-13-9-3-8(7(2)14)10(15)4-11(9)17-12(6)13/h3-4,6,12-13,15H,5H2,1-2H3/t6-,12-,13-/m1/s1

InChI Key

CVBFRNFTZXHUAN-AJJMPYILSA-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
Gynura elliptica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Acetophenones

Direct Parent

Acetophenones

Alternative Parents

Substituents

Acetophenone
Coumaran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Oxolane
Vinylogous acid
Ketone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	1.62	ALOGPS
logP	1.91	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.16 m³·mol⁻¹	ChemAxon
Polarizability	24.17 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

Not Available

Chemspider ID

8737043

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10561655

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Z, Ye X, Zhang Z, Zhao Q, Xiang Y, Xu N, Wang Q, Pan Y, Guo X, Wang Z: Genetic diversity and selection signatures of four indigenous pig breeds from eastern China. Anim Genet. 2022 Apr 30. doi: 10.1111/age.13208. [PubMed:35489815 ]
Wu A, Fahey MT, Cui D, El-Behesy B, Story DA: An evaluation of the outcome metric 'days alive and at home' in older patients after hip fracture surgery. Anaesthesia. 2022 Apr 30. doi: 10.1111/anae.15742. [PubMed:35489814 ]
Martinez-Pizarro S: Prolotherapy with dextrose to reduce pain in osteoarthritis of the knee. Reumatol Clin (Engl Ed). 2022 Apr;18(4):251-252. doi: 10.1016/j.reumae.2020.08.002. Epub 2021 Apr 5. [PubMed:35489813 ]
Gryspeerdt E, Mutluoglu M, Rummens S, Van Wambeke P, Peers K: Wasting of the hand is not fate! A case of missed true neurogenic thoracic outlet syndrome. Reumatol Clin (Engl Ed). 2022 Apr;18(4):249-250. doi: 10.1016/j.reumae.2021.05.005. [PubMed:35489812 ]
Lin WY, Teng CM, Tsai IL, Chen IS: Anti-platelet aggregation constituents from Gynura elliptica. Phytochemistry. 2000 Apr;53(8):833-6. doi: 10.1016/s0031-9422(99)00599-3. [PubMed:10820787 ]

Showing NP-Card for (+)-Gynunone (NP0074823)

MOL for NP0074823 ((+)-Gynunone)

3D MOL for NP0074823 ((+)-Gynunone)

3D SDF for NP0074823 ((+)-Gynunone)

3D-SDF for NP0074823 ((+)-Gynunone)

PDB for NP0074823 ((+)-Gynunone)

3D PDB for NP0074823 ((+)-Gynunone)

SMILES for NP0074823 ((+)-Gynunone)

INCHI for NP0074823 ((+)-Gynunone)

Structure for NP0074823 ((+)-Gynunone)

3D Structure for NP0074823 ((+)-Gynunone)