NP-MRD: Showing NP-Card for (4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one (NP0194907)

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Record Information

Version

2.0

Created at

2022-09-04 12:39:47 UTC

Updated at

2022-09-04 12:39:47 UTC

NP-MRD ID

NP0194907

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

Description

Alpha-Cyperone, also known as α-cyperone, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. (4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one is found in Cyperus alopecuroides, Cyperus corymbosus, Cyperus rotundus and Magnolia alba. (4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one was first documented in 2022 (PMID: 35531691). Based on a literature review a small amount of articles have been published on alpha-Cyperone (PMID: 36053011) (PMID: 35427911) (PMID: 35356235) (PMID: 35114351).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    3.5698    0.9853    1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9225    0.1295    0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7082   -0.6815   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -0.0225    0.5627 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0899   -1.4226    0.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3415   -1.7533    0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2579   -0.8433    0.1451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9255   -1.6282   -0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -0.4088    1.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726    0.3438    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6795    1.6085   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2867    2.7306   -0.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    1.5298   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6144    2.7360   -1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    0.3793   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    0.3029   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0370    1.6009    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384    1.0836    1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963   -0.4554   -1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7743   -0.3627   -0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6341   -1.7706   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0634    0.6409    1.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -2.0912    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429   -1.6469    1.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7029   -1.8381    1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4365   -2.8182    0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0351   -1.0341   -1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8623   -2.1132   -0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2406   -2.4852   -1.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933    0.3414    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9008   -1.2502    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309    0.5783    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599   -0.2048   -0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2499    3.6108   -0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579    2.6754   -2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670    2.9563   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    1.1873   -1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -0.5897   -1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16  4  1  0
 15  7  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  1 17  1  0
  1 18  1  0
  4 22  1  1
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
M  END


  Mrv1652309042214392D          

 16 17  0  0  1  0            999 V2000
    0.0000   -2.4750    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   -1.2375    0.0000 C   0  0  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194907

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@@]2(C)CCC(=O)C(C)=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3/t12-,15+/m1/s1

> <INCHI_KEY>
KUFXJZXMWHNCEH-DOMZBBRYSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.253546403475045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,7R)-1,4a-dimethyl-7-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

> <JCHEM_LOGP>
3.8083682056666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.788972738672884

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
67.879

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,7R)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+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  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+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
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   15                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7   16                                                  
CONECT   16   15    4                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
a-Cyperone	Generator
Α-cyperone	Generator

Chemical Formula

C₁₅H₂₂O

Average Mass

218.3400 Da

Monoisotopic Mass

218.16707 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@@]2(C)CCC(=O)C(C)=C2C1

InChI Identifier

InChI=1S/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3/t12-,15+/m1/s1

InChI Key

KUFXJZXMWHNCEH-DOMZBBRYSA-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
Cyperus alopecuroides	LOTUS Database	35616633
Cyperus corymbosus	LOTUS Database	35616633
Cyperus rotundus	LOTUS Database	35616633
Michelia alba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

C00012759

Chemspider ID

4954527

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6452086

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qiao N, Wang Q, Tao Y, Wu J, Fang Y, Ni Y, Ding X: alpha-Cyperone ameliorates depression in mammary gland hyperplasia and chronic unpredictable mild stress rat by regulating hormone, inflammation, and oxidative stress. Immunopharmacol Immunotoxicol. 2023 Feb;45(1):73-82. doi: 10.1080/08923973.2022.2115925. Epub 2022 Sep 2. [PubMed:36053011 ]
Zhang Y, Tang JF, Tian QH, Chen RY, Wang W, Wang WX, Yan JZ, Zhang H: [Discrimination of quality markers of Shujin Huoxue Capsules based on five principles coupled with cobweb model]. Zhongguo Zhong Yao Za Zhi. 2022 May;47(9):2440-2448. doi: 10.19540/j.cnki.cjcmm.20210525.304. [PubMed:35531691 ]
Deng M, Xie P, Liu J, Zhou Y, Chen Z, Ma Y, Yang J: alpha-Cyperone Improves Rat Spinal Cord Tissue Damage via Akt/Nrf2 and NF-kappaB Pathways. J Surg Res. 2022 Aug;276:331-339. doi: 10.1016/j.jss.2022.02.006. Epub 2022 Apr 12. [PubMed:35427911 ]
Lu J, Li W, Xu N, Yao P, Wang S, Fu C, Pei J, Chen H, Wang S: Quality Status Analysis and Intrinsic Connection Research of Growing place, Morphological Characteristics, and Quality of Chinese Medicine: Cyperi Rhizoma (Xiangfu) as a Case Study. Evid Based Complement Alternat Med. 2022 Mar 21;2022:8309832. doi: 10.1155/2022/8309832. eCollection 2022. [PubMed:35356235 ]
Alavi M, Karimi N: Antibacterial, hemoglobin/albumin-interaction, and molecular docking properties of phytogenic AgNPs functionalized by three antibiotics of penicillin, amoxicillin, and tetracycline. Microb Pathog. 2022 Mar;164:105427. doi: 10.1016/j.micpath.2022.105427. Epub 2022 Jan 31. [PubMed:35114351 ]
LOTUS database [Link]

Showing NP-Card for (4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one (NP0194907)

MOL for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D MOL for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D SDF for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D-SDF for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

PDB for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D PDB for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

SMILES for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

INCHI for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

Structure for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)

3D Structure for NP0194907 ((4as,7r)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one)