NP-MRD: Showing NP-Card for 2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate (NP0188760)

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Record Information

Version

1.0

Created at

2022-09-04 05:08:44 UTC

Updated at

2022-09-04 05:08:45 UTC

NP-MRD ID

NP0188760

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate

Description

Erectquione B belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. 2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate is found in Hypericum erectum. It was first documented in 2010 (PMID: 20127665). Based on a literature review a significant number of articles have been published on Erectquione B (PMID: 36057864) (PMID: 36057863) (PMID: 36057862) (PMID: 36057861).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207082D          

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 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 21 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 28 34  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0188760

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OC1=C(CC=C(C)C)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(OC(=O)C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O6/c1-17(2)11-10-12-21(9)14-16-23-24(30)22(15-13-18(3)4)26(34-28(32)19(5)6)25(31)27(23)35-29(33)20(7)8/h11,13-14,19-20H,10,12,15-16H2,1-9H3/b21-14+

> <INCHI_KEY>
LLCTZEXRKYOVJM-KGENOOAVSA-N

> <FORMULA>
C29H40O6

> <MOLECULAR_WEIGHT>
484.633

> <EXACT_MASS>
484.282489008

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.81481307672272

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate

> <JCHEM_LOGP>
7.176601764999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.92801160423277

> <JCHEM_POLAR_SURFACE_AREA>
86.74000000000001

> <JCHEM_REFRACTIVITY>
142.58939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   34                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   28   11   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₆

Average Mass

484.6330 Da

Monoisotopic Mass

484.28249 Da

IUPAC Name

2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate

Traditional Name

2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC1=C(CC=C(C)C)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(OC(=O)C(C)C)C1=O

InChI Identifier

InChI=1S/C29H40O6/c1-17(2)11-10-12-21(9)14-16-23-24(30)22(15-13-18(3)4)26(34-28(32)19(5)6)25(31)27(23)35-29(33)20(7)8/h11,13-14,19-20H,10,12,15-16H2,1-9H3/b21-14+

InChI Key

LLCTZEXRKYOVJM-KGENOOAVSA-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
Hypericum erectum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

Prenylbenzoquinone
Monocyclic monoterpenoid
Monoterpenoid
P-benzoquinone
Quinone
Dicarboxylic acid or derivatives
Enol ester
Ketone
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	7.18	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	86.74 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	142.59 m³·mol⁻¹	ChemAxon
Polarizability	55.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4475950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317014

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Moon HI: Antiplasmodial and cytotoxic activity of phloroglucinol derivatives from Hypericum erectum Thunb. Phytother Res. 2010 Jun;24(6):941-4. doi: 10.1002/ptr.3104. [PubMed:20127665 ]
Poon AWC, Hofstaetter L, Judd-Lam S: Social connectedness of carers: An Australian national survey of carers. Health Soc Care Community. 2022 Sep 4. doi: 10.1111/hsc.13987. [PubMed:36057864 ]
Johnson-Laghi KA, Woo SM, Zafar Z, Fernandez S, Desale S, Robertazzi SE, Smith CI, Thomas AM, Lalos AT, Georgia SJ, Jenkins ML, Faust TW, Fishbein TM, Satoskar RS, Rangnekar AS, Hsu CC: Alcohol-associated liver disease predicts increased post-liver transplant opioid use. Clin Transplant. 2022 Sep 4:e14811. doi: 10.1111/ctr.14811. [PubMed:36057863 ]
Michael GC, Grema BA, Ashimi AO, Olawumi AL, Umar ZA, Mahmoud Z, Aji SA: Predictors of Satisfaction with Wound Care Services in an Outpatient Setting in Kano, Nigeria. West Afr J Med. 2022 Aug 31;39(8):800-807. [PubMed:36057862 ]
Jouglar E, Laprie A, Isfan F, Dumont B, Thebaud E, Escande A, Supiot S: Locoregional failure after postoperative flank irradiation for nephroblastoma: Results from the French cohort of the SIOP-2001 trial. Pediatr Blood Cancer. 2022 Sep 4:e29950. doi: 10.1002/pbc.29950. [PubMed:36057861 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate (NP0188760)

MOL for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

3D MOL for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

3D SDF for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

3D-SDF for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

PDB for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

3D PDB for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

SMILES for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

INCHI for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

Structure for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)

3D Structure for NP0188760 (2-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-(3-methylbut-2-en-1-yl)-5-[(2-methylpropanoyl)oxy]-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylpropanoate)