NP-MRD: Showing NP-Card for (3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one (NP0298463)

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Record Information

Version

2.0

Created at

2022-09-10 09:43:48 UTC

Updated at

2022-09-10 09:43:48 UTC

NP-MRD ID

NP0298463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one

Description

TENUIFOLIDE A, also known as isotenuifolide a, belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. (3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one is found in Cinnamomum tenuifolium. (3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one was first documented in 2009 (PMID: 19754130). Based on a literature review very few articles have been published on TENUIFOLIDE A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102211432D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102211432D          

 35 35  0  0  1  0            999 V2000
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   10.4901    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2046    2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9191    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6335    2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3480    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0625    2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4914    2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2059    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9204    2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6348    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3493    2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944    4.2001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6790    3.9451    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  6 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0298463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCCCCCC\C=C1\[C@H](O)C(=C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H58O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-30-31(33)29(2)35-32(30)34/h28,31,33H,2-27H2,1H3/b30-28-/t31-/m1/s1

> <INCHI_KEY>
RXXMEENDMWGIGU-JHDDAZIHSA-N

> <FORMULA>
C32H58O3

> <MOLECULAR_WEIGHT>
490.813

> <EXACT_MASS>
490.438595728

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
67.17026184520026

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z,4S)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one

> <JCHEM_LOGP>
11.636253582999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.968293103937235

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.379884274877147

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6642440151797535

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
151.3547

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,4S)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.099  10.551   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.194   9.305   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.346   9.305   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.822   7.840   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.287   7.364   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.424   6.935   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.424   5.395   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.910   4.625   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.244   5.395   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.577   4.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.911   5.395   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.245   4.625   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.578   5.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.912   4.625   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.246   5.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.579   4.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.913   5.395   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.247   4.625   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.581   5.395   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.914   4.625   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.248   5.395   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.582   4.625   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.915   5.395   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.249   4.625   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.583   5.395   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.916   4.625   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.250   5.395   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      27.584   4.625   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.917   5.395   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.251   4.625   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      31.585   5.395   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.918   4.625   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      34.252   5.395   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.670   7.840   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.134   7.364   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   34                                                  
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                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34    6    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

View in JSmol

Synonyms

Value	Source
Isotenuifolide a	MeSH

Chemical Formula

C₃₂H₅₈O₃

Average Mass

490.8130 Da

Monoisotopic Mass

490.43860 Da

IUPAC Name

(3Z,4S)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one

Traditional Name

(3Z,4S)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCC\C=C1\[C@H](O)C(=C)OC1=O

InChI Identifier

InChI=1S/C32H58O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-30-31(33)29(2)35-32(30)34/h28,31,33H,2-27H2,1H3/b30-28-/t31-/m1/s1

InChI Key

RXXMEENDMWGIGU-JHDDAZIHSA-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
Cinnamomum tenuifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxolanes

Sub Class

Not Available

Direct Parent

Oxolanes

Alternative Parents

Substituents

Enol ester
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	11.64	ChemAxon
pKa (Strongest Acidic)	11.38	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	151.35 m³·mol⁻¹	ChemAxon
Polarizability	67.17 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

C00047932

Chemspider ID

24653493

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44557419

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin RJ, Cheng MJ, Huang JC, Lo WL, Yeh YT, Yen CM, Lu CM, Chen CY: Cytotoxic compounds from the stems of Cinnamomum tenuifolium. J Nat Prod. 2009 Oct;72(10):1816-24. doi: 10.1021/np900225p. [PubMed:19754130 ]
LOTUS database [Link]

Showing NP-Card for (3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one (NP0298463)

MOL for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

3D MOL for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

3D SDF for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

3D-SDF for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

PDB for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

3D PDB for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

SMILES for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

INCHI for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

Structure for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)

3D Structure for NP0298463 ((3z,4s)-3-heptacosylidene-4-hydroxy-5-methylideneoxolan-2-one)