NP-MRD: Showing NP-Card for 2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one (NP0147508)

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Record Information

Version

2.0

Created at

2022-09-02 03:07:38 UTC

Updated at

2022-09-02 03:07:38 UTC

NP-MRD ID

NP0147508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one

Description

SURINONE A belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. 2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one is found in Peperomia leptostachya. 2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one was first documented in 2003 (PMID: 12809722). Based on a literature review very few articles have been published on SURINONE A (PMID: 17547458).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205072D          

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 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0147508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CCC(=O)C(C(=O)CCCCCCCCCCCCCCC2=CC=C3OCOC3=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O6/c29-22(27-23(30)16-17-24(31)28(27)32)14-12-10-8-6-4-2-1-3-5-7-9-11-13-21-15-18-25-26(19-21)34-20-33-25/h15,18-19,24,31-32H,1-14,16-17,20H2

> <INCHI_KEY>
RTNTXKREQUWGAI-UHFFFAOYSA-N

> <FORMULA>
C28H40O6

> <MOLECULAR_WEIGHT>
472.622

> <EXACT_MASS>
472.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.88807553439604

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[15-(2H-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
6.7381943316666675

> <ALOGPS_LOGS>
-5.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.310658878953014

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0165161018439632

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3067423830469718

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
132.67569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[15-(2H-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -8.002 -20.020   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.002 -18.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668 -17.710   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001 -17.710   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -17.710   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334 -17.710   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -17.710   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -17.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -17.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003 -17.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337 -15.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670 -17.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.135 -18.186   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      17.040 -16.940   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.135 -15.694   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -9.336 -17.710   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -10.669 -20.020   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -12.003 -17.710   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -13.337 -18.480   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.669 -15.400   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.002 -15.400   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26    2   27   33                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₆

Average Mass

472.6220 Da

Monoisotopic Mass

472.28249 Da

IUPAC Name

2-[15-(2H-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one

Traditional Name

2-[15-(2H-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

OC1CCC(=O)C(C(=O)CCCCCCCCCCCCCCC2=CC=C3OCOC3=C2)=C1O

InChI Identifier

InChI=1S/C28H40O6/c29-22(27-23(30)16-17-24(31)28(27)32)14-12-10-8-6-4-2-1-3-5-7-9-11-13-21-15-18-25-26(19-21)34-20-33-25/h15,18-19,24,31-32H,1-14,16-17,20H2

InChI Key

RTNTXKREQUWGAI-UHFFFAOYSA-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
Peperomia leptostachya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Cyclohexenone
Benzenoid
Vinylogous acid
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Enol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

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	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.86	ALOGPS
logP	6.74	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	3.02	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	132.68 m³·mol⁻¹	ChemAxon
Polarizability	55.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037867

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

21579137

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li N, Wu JL, Hasegawa T, Sakai J, Bai LM, Wang LY, Kakuta S, Furuya Y, Ogura H, Kataoka T, Tomida A, Tsuruo T, Ando M: Bioactive polyketides from Peperomia duclouxii. J Nat Prod. 2007 Jun;70(6):998-1001. doi: 10.1021/np070089n. Epub 2007 Jun 5. [PubMed:17547458 ]
Cheng MJ, Lee SJ, Chang YY, Wu SH, Tsai IL, Jayaprakasam B, Chen IS: Chemical and cytotoxic constituents from Peperomia sui. Phytochemistry. 2003 Jul;63(5):603-8. doi: 10.1016/s0031-9422(03)00183-3. [PubMed:12809722 ]
LOTUS database [Link]

Showing NP-Card for 2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one (NP0147508)

MOL for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

3D MOL for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

3D SDF for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

3D-SDF for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

PDB for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

3D PDB for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

SMILES for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

INCHI for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

Structure for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)

3D Structure for NP0147508 (2-[15-(2h-1,3-benzodioxol-5-yl)pentadecanoyl]-3,4-dihydroxycyclohex-2-en-1-one)