NP-MRD: Showing NP-Card for Precocene 1 (NP0002898)

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Record Information

Version

1.0

Created at

2020-11-23 19:43:07 UTC

Updated at

2021-08-19 23:59:30 UTC

NP-MRD ID

NP0002898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Precocene 1

Provided By

BMRB

Description

Precocene I, also known as pricocene I, belongs to the class of organic compounds known as precocenes. These are aromatic heteropolycyclic compounds that contain a 2,2-dimethyl-1-benzopyran moiety, which carries a methoxy group at the ring 7-position. Precocene I is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Precocene 1 is found in Ageratum conyzoides, Ageratum houstonianum, Artemisia capillaris and Bidens pilosa. It was first documented in 1986 (PMID: 3797775). Based on a literature review a significant number of articles have been published on Precocene I (PMID: 17984079) (PMID: 11705333) (PMID: 17262477) (PMID: 21741958).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -5.2728   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399   -1.3674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776   -0.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7481    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    1.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529    1.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0824   -0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -1.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505   -1.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128   -0.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9762    0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0915   -1.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4423    1.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095    1.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609   -2.0121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5847    0.6536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6056    0.0089    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0809    1.6293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5562    3.2498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2742   -2.7436    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2448   -0.7339    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8274    1.5093    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4395    0.3463    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590   -1.4812    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7077   -2.2755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -3.0807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5965    2.1435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390    3.3719    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
 10  9  1  6
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
  8  3  1  0
 14  6  1  0
  1 15  1  6
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  8 20  1  0
 11 21  1  1
 11 22  1  0
 11 23  1  0
 12 24  1  6
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
M  END
> <DATABASE_ID>
NP0002898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C=CC(C)(C)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O2/c1-12(2)7-6-9-4-5-10(13-3)8-11(9)14-12/h4-8H,1-3H3

> <INCHI_KEY>
CPTJXGLQLVPIGP-UHFFFAOYSA-N

> <FORMULA>
C12H14O2

> <MOLECULAR_WEIGHT>
190.242

> <EXACT_MASS>
190.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.235714259336227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-2,2-dimethyl-2H-chromene

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
2.716197952333333

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.571056075441259

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
56.91460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
precocene I

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.195  -3.757   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13    3                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    NP0002898
HETATM    1  C1  UNL     1      -4.831  -0.237   1.283  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.516   0.218   1.501  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.439  -0.092   0.712  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.491  -0.890  -0.402  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.349  -1.145  -1.133  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.110  -0.619  -0.791  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.066   0.183   0.331  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.210   0.436   1.062  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.170   0.697   0.658  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.367   0.484  -0.032  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.421  -0.156   0.884  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.916   1.857  -0.384  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.259  -0.383  -1.225  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.090  -0.885  -1.557  1.00  0.00           C  
HETATM   15  H1  UNL     1      -5.424  -0.232   2.221  1.00  0.00           H  
HETATM   16  H2  UNL     1      -5.318   0.489   0.599  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.875  -1.226   0.784  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.452  -1.304  -0.675  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.378  -1.776  -2.019  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.138   1.077   1.946  1.00  0.00           H  
HETATM   21  H7  UNL     1       4.089   0.599   1.320  1.00  0.00           H  
HETATM   22  H8  UNL     1       2.927  -0.670   1.746  1.00  0.00           H  
HETATM   23  H9  UNL     1       3.996  -0.938   0.346  1.00  0.00           H  
HETATM   24  H10 UNL     1       2.560   2.143  -1.379  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.583   2.632   0.337  1.00  0.00           H  
HETATM   26  H12 UNL     1       4.034   1.870  -0.338  1.00  0.00           H  
HETATM   27  H13 UNL     1       3.163  -0.600  -1.826  1.00  0.00           H  
HETATM   28  H14 UNL     1       1.021  -1.531  -2.450  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   14
CONECT    7    8    8    9
CONECT    8   20
CONECT    9   10
CONECT   10   11   12   13
CONECT   11   21   22   23
CONECT   12   24   25   26
CONECT   13   14   14   27
CONECT   14   28
END

View in JSmol

Synonyms

Value	Source
2,2-Dimethyl-2H-chromen-7-yl methyl ether	ChEBI
2,2-Dimethyl-7-methoxy-2H-1-benzopyran	ChEBI
6-Demethoxyageratochromene	ChEBI
7-Methoxy-2,2-dimethylchromene	ChEBI
Precocene 1	ChEBI
PRICOCENE I	ChEBI

Chemical Formula

C₁₂H₁₄O₂

Average Mass

190.2420 Da

Monoisotopic Mass

190.09938 Da

IUPAC Name

7-methoxy-2,2-dimethyl-2H-chromene

Traditional Name

precocene I

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=CC(C)(C)OC2=C1

InChI Identifier

InChI=1S/C12H14O2/c1-12(2)7-6-9-4-5-10(13-3)8-11(9)14-12/h4-8H,1-3H3

InChI Key

CPTJXGLQLVPIGP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ageratina aromatica	KNApSAcK Database	22123792
Ageratum conyzoides	LOTUS Database	35616633
Ageratum houstonianum	LOTUS Database	35616633
Artemisia capillaris	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as precocenes. These are aromatic heteropolycyclic compounds that contain a 2,2-dimethyl-1-benzopyran moiety, which carries a methoxy group at the ring 7-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Precocenes

Alternative Parents

Not Available

Substituents

Not Available

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	292.74 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	67.52 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.350	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.36	ALOGPS
logP	2.72	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.91 m³·mol⁻¹	ChemAxon
Polarizability	21.24 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0256741

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002439

Chemspider ID

26617

KEGG Compound ID

C09017

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

8368

Good Scents ID

rw1278691

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Sharma K, Sharma OP: Analysis of precocenes in the essential oil of Ageratum spp. by reverse-phase high-performance liquid chromatography. Phytochem Anal. 2001 Jul-Aug;12(4):263-5. doi: 10.1002/pca.587. [PubMed:11705333 ]
Onayade OA, Looman A, Scheffer JJ, Svendsen AB: Precocene I and Other Constituents of the Essential Oil of Platostoma africanum. Planta Med. 1989 Dec;55(6):553-5. doi: 10.1055/s-2006-962093. [PubMed:17262477 ]
Ly VT, Brock B: Effects of CYP inhibitors on precocene I metabolism and toxicity in rat liver slices. Chem Biol Interact. 2011 Sep 5;193(2):109-18. doi: 10.1016/j.cbi.2011.05.011. Epub 2011 Jul 1. [PubMed:21741958 ]
Baldellou MI, Belles X: Effects of precocenes on ovarian development of the seed bug, Oxycarenus lavaterae (F.). Rev Esp Fisiol. 1986 Sep;42(3):315-7. [PubMed:3797775 ]

Showing NP-Card for Precocene 1 (NP0002898)

MOL for NP0002898 (Precocene 1)

3D MOL for NP0002898 (Precocene 1)

3D SDF for NP0002898 (Precocene 1)

3D-SDF for NP0002898 (Precocene 1)

PDB for NP0002898 (Precocene 1)

3D PDB for NP0002898 (Precocene 1)

SMILES for NP0002898 (Precocene 1)

INCHI for NP0002898 (Precocene 1)

Structure for NP0002898 (Precocene 1)

3D Structure for NP0002898 (Precocene 1)