NP-MRD: Showing NP-Card for Bisacurone C (NP0141012)

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Record Information

Version

1.0

Created at

2022-06-29 22:05:20 UTC

Updated at

2022-06-29 22:05:20 UTC

NP-MRD ID

NP0141012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bisacurone C

Description

Bisacurone C belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Bisacurone C is found in Curcuma xanthorrhiza. It was first documented in 2018 (PMID: 29662734). Based on a literature review a significant number of articles have been published on Bisacurone C (PMID: 34774052) (PMID: 32802138) (PMID: 31394768) (PMID: 30809971).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
   -5.0253   -0.8882   -0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4367    0.4680   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3485    1.6484   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1454    0.6759   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1922   -0.4164   -0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5268   -1.6212   -0.5676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7100   -0.1626   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905   -1.0657    0.5783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7038   -0.6744    1.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969   -0.8914    0.6896 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6266    0.5293    1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997    1.1291    0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.3206    0.3074 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0068    1.2340   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3371   -0.5553    1.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081   -0.3845   -0.8874 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8771    0.5982   -1.8021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1497   -1.2544   -0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8780   -1.2778   -1.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1389   -0.8252   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6352   -1.5806    0.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1360    1.9805    1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4007    1.3981   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0132    2.4700   -0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317    1.6864   -0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901   -0.3514   -1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463    0.8889   -0.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078   -2.1023    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2246    0.2960    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887   -0.6285    2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625   -1.4399    2.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7298   -1.5242    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    1.1435    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9441    2.1587    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7833    2.2717    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1131    1.2231   -1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417    0.9335    0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1560   -1.4990    1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.9644   -1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8846    0.6555   -1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656   -2.3084   -0.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983   -1.2934   -1.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  8 10  1  0
 10 18  1  0
 18 16  1  0
 16 17  1  0
 16 13  1  0
 13 14  1  0
 13 15  1  1
 13 12  1  0
 12 11  2  0
 11 10  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
  8 28  1  6
  7 26  1  0
  7 27  1  0
  4 25  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
 10 32  1  1
 18 41  1  0
 18 42  1  0
 16 39  1  6
 17 40  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 12 34  1  0
 11 33  1  0
M  END

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.057   3.670   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   16   17                                             
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₃

Average Mass

252.3540 Da

Monoisotopic Mass

252.17254 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H24O3/c1-10(2)7-13(16)8-11(3)12-5-6-15(4,18)14(17)9-12/h5-7,11-12,14,17-18H,8-9H2,1-4H3/t11-,12+,14+,15+/m0/s1

InChI Key

QJOWFYQIUZMPRY-CTHBEMJXSA-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
Curcuma xanthorrhiza	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Bisabolane sesquiterpenoid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
1,2-diol
Ketone
Secondary alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055416

Chemspider ID

10259029

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14287399

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Uchio R, Kawasaki K, Okuda-Hanafusa C, Saji R, Muroyama K, Murosaki S, Yamamoto Y, Hirose Y: Curcuma longa extract improves serum inflammatory markers and mental health in healthy participants who are overweight: a randomized, double-blind, placebo-controlled trial. Nutr J. 2021 Nov 13;20(1):91. doi: 10.1186/s12937-021-00748-8. [PubMed:34774052 ]
An S, Jang E, Lee JH: Preclinical Evidence of Curcuma longa and Its Noncurcuminoid Constituents against Hepatobiliary Diseases: A Review. Evid Based Complement Alternat Med. 2020 Jul 28;2020:8761435. doi: 10.1155/2020/8761435. eCollection 2020. [PubMed:32802138 ]
Uchio R, Muroyama K, Okuda-Hanafusa C, Kawasaki K, Yamamoto Y, Murosaki S: Hot Water Extract of Curcuma longa L. Improves Serum Inflammatory Markers and General Health in Subjects with Overweight or Prehypertension/Mild Hypertension: A Randomized, Double-Blind, Placebo-Controlled Trial. Nutrients. 2019 Aug 7;11(8). pii: nu11081822. doi: 10.3390/nu11081822. [PubMed:31394768 ]
Asada K, Ohara T, Muroyama K, Yamamoto Y, Murosaki S: Effects of hot water extract of Curcuma longa on human epidermal keratinocytes in vitro and skin conditions in healthy participants: A randomized, double-blind, placebo-controlled trial. J Cosmet Dermatol. 2019 Dec;18(6):1866-1874. doi: 10.1111/jocd.12890. Epub 2019 Feb 27. [PubMed:30809971 ]
Kawasaki K, Muroyama K, Murosaki S: Effect of a water extract of Curcuma longa on emotional states in healthy participants. Biosci Microbiota Food Health. 2018;37(2):25-29. doi: 10.12938/bmfh.17-020. Epub 2018 Feb 2. [PubMed:29662734 ]

Showing NP-Card for Bisacurone C (NP0141012)

MOL for NP0141012 (Bisacurone C)

3D MOL for NP0141012 (Bisacurone C)

3D SDF for NP0141012 (Bisacurone C)

3D-SDF for NP0141012 (Bisacurone C)

PDB for NP0141012 (Bisacurone C)

3D PDB for NP0141012 (Bisacurone C)

SMILES for NP0141012 (Bisacurone C)

INCHI for NP0141012 (Bisacurone C)

Structure for NP0141012 (Bisacurone C)

3D Structure for NP0141012 (Bisacurone C)