NP-MRD: Showing NP-Card for 4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate (NP0218816)

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Record Information

Version

1.0

Created at

2022-09-05 19:36:14 UTC

Updated at

2022-09-05 19:36:14 UTC

NP-MRD ID

NP0218816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate

Description

4-(Hexa-2,4-diyn-1-ylidene)-3'H-3,6-dioxaspiro[bicyclo[3.1.0]Hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate is found in Leucanthemum monspeliense. 4-(Hexa-2,4-diyn-1-ylidene)-3'H-3,6-dioxaspiro[bicyclo[3.1.0]Hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191516312D          

 23 25  0  0  0  0            999 V2000
    3.1424    6.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    5.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2955    4.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    4.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4487    3.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0252    2.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4267    2.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2457    1.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4048    1.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255    1.5829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3830    0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639    0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025   -0.2326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2453   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839   -1.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0496   -1.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2924   -1.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967   -2.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -2.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6841    0.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8956    0.5372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796    1.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  3  0  0  0  0
  3  4  1  0  0  0  0
  4  5  3  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC#CC#CC=C1OC2(OC=CC2OC(=O)C=C(C)C)C2OC12

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-4-5-6-7-8-13-16-17(22-16)18(23-13)14(9-10-20-18)21-15(19)11-12(2)3/h8-11,14,16-17H,1-3H3

> <INCHI_KEY>
QUUPHSUNZQFZDQ-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.321

> <EXACT_MASS>
312.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.277429142177084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(hexa-2,4-diyn-1-ylidene)-3'H-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
3.481324899666667

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.14250578587931

> <JCHEM_POLAR_SURFACE_AREA>
57.290000000000006

> <JCHEM_REFRACTIVITY>
85.50640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(hexa-2,4-diyn-1-ylidene)-3'H-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       5.866  11.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.075  10.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.285   9.211   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.495   7.890   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.704   6.568   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.914   5.246   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.663   3.901   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.192   3.717   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.489   2.205   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.834   2.955   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.963   1.907   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.315   0.510   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.786   0.694   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.738  -0.434   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.191  -1.906   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.143  -3.034   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.693  -2.249   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.146  -3.721   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.647  -4.064   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.098  -4.849   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.144   1.456   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.672   1.003   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.015   2.504   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13   21                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    9   22   23                                                  
CONECT   22   21   23                                                       
CONECT   23   22    7   21                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
4-(Hexa-2,4-diyn-1-ylidene)-3'H-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3210 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

4-(hexa-2,4-diyn-1-ylidene)-3'H-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate

Traditional Name

4-(hexa-2,4-diyn-1-ylidene)-3'H-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC#CC#CC=C1OC2(OC=CC2OC(=O)C=C(C)C)C2OC12

InChI Identifier

InChI=1S/C18H16O5/c1-4-5-6-7-8-13-16-17(22-16)18(23-13)14(9-10-20-18)21-15(19)11-12(2)3/h8-11,14,16-17H,1-3H3

InChI Key

QUUPHSUNZQFZDQ-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
Leucanthemum monspeliense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Ketal
Fatty acid ester
Para-dioxane
Dihydrofuran
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.66	ALOGPS
logP	3.48	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.51 m³·mol⁻¹	ChemAxon
Polarizability	32.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate (NP0218816)

MOL for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

3D MOL for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

3D SDF for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

3D-SDF for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

PDB for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

3D PDB for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

SMILES for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

INCHI for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

Structure for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)

3D Structure for NP0218816 (4-(hexa-2,4-diyn-1-ylidene)-3'h-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,2'-furan]-3'-yl 3-methylbut-2-enoate)