NP-MRD: Showing NP-Card for Tageteserectone A (NP0332000)

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Record Information

Version

2.0

Created at

2023-10-17 16:29:40 UTC

Updated at

2024-09-03 04:17:39 UTC

NP-MRD ID

NP0332000

Natural Product DOI

https://doi.org/10.57994/1121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tageteserectone A

Description

Tageteserectone A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Tageteserectone A was first documented in 2023 (PMID: 37714249). Based on a literature review very few articles have been published on Tageteserectone A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10172316292D          

 18 19  0  0  1  0            999 V2000
   -0.1303    0.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    1.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.6507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1270   -0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -2.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -2.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.1257    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
  4  2  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  5  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  4 13  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332000

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C1/[C@@H](O)[C@H]1[C@H]1C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-5-10(17)7-15(3,4)13(8)12-11(14(12)18)6-9(2)16/h5-6,12-14,18H,7H2,1-4H3/b11-6-/t12-,13-,14-/m1/s1

> <INCHI_KEY>
DLTGJAIVTURCET-FKWOOBLNSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.045317194483193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,3Z)-2-hydroxy-3-(2-oxopropylidene)cyclopropyl]-3,5,5-trimethylcyclohex-2-en-1-one

> <JCHEM_LOGP>
1.4136060443333343

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.33221975802566

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.521455293809872

> <JCHEM_PKA_STRONGEST_BASIC>
-3.008049003927657

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
71.17369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,3Z)-2-hydroxy-3-(2-oxopropylidene)cyclopropyl]-3,5,5-trimethylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-23         0                                  
HETATM    1  C   UNK     0      -0.243   0.537   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770   1.985   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.747   2.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.104   1.215   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.104  -0.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -1.659   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.000  -2.429   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.874  -1.659   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.207  -2.429   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.207  -3.969   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.541  -4.739   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.874  -4.739   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.437   1.985   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.771   1.215   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.437   3.525   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.104   4.295   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.770   3.525   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.104   5.835   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   17                                             
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    5    6    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    2                                                       
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(4R)-4-[(1S,2S,3Z)-2-hydroxy-3-(2-oxopropylidene)cyclopropyl]-3,5,5-trimethylcyclohex-2-en-1-one

Traditional Name

(4R)-4-[(1S,2S,3Z)-2-hydroxy-3-(2-oxopropylidene)cyclopropyl]-3,5,5-trimethylcyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(=O)\C=C1/[C@@H](O)[C@H]1[C@H]1C(C)=CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C15H20O3/c1-8-5-10(17)7-15(3,4)13(8)12-11(14(12)18)6-9(2)16/h5-6,12-14,18H,7H2,1-4H3/b11-6-/t12-,13-,14-/m1/s1

InChI Key

DLTGJAIVTURCET-FKWOOBLNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
erecta		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Secondary alcohol
Cyclopropanol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.41	ChemAxon
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.17 m³·mol⁻¹	ChemAxon
Polarizability	27.05 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tageteserectone A (NP0332000)

MOL for NP0332000 (Tageteserectone A)

3D MOL for NP0332000 (Tageteserectone A)

3D SDF for NP0332000 (Tageteserectone A)

3D-SDF for NP0332000 (Tageteserectone A)

PDB for NP0332000 (Tageteserectone A)

3D PDB for NP0332000 (Tageteserectone A)

SMILES for NP0332000 (Tageteserectone A)

INCHI for NP0332000 (Tageteserectone A)

Structure for NP0332000 (Tageteserectone A)

3D Structure for NP0332000 (Tageteserectone A)