NP-MRD: Showing NP-Card for Manshurolide (NP0058997)

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Record Information

Version

2.0

Created at

2022-04-28 04:17:20 UTC

Updated at

2022-04-28 04:17:20 UTC

NP-MRD ID

NP0058997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Manshurolide

Description

Manshurolide belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Manshurolide is found in Aristolochia cucurbitafolia , Aristolochia cucurbitifolia, Aristolochia heterophylla, Aristolochia heterophylla Hemsl , Aristolochia manshuriensis and Aristolochia mollissima. Manshurolide was first documented in 2016 (PMID: 27203803). Based on a literature review very few articles have been published on Manshurolide (PMID: 30200734).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    3.8864   -0.8169   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449   -0.0361    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6020    1.2579   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024    1.9564   -0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940    2.4495    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973    2.0051    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993    1.2781    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.6452    0.0378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0281   -0.3954   -0.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -1.6550   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9269   -2.5996    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5711   -1.9730    0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -1.5521   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5105   -0.7655    0.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9510    1.8209   -0.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7129    2.4010   -0.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674    3.1160   -1.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246   -0.1749   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6172   -1.5618   -0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1289   -1.4163    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087    1.8735    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8252    1.2986   -1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7731    2.7735   -1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257    2.2964    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5142    3.5823    0.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    0.9809    2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871    0.2874    0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1294   -0.0793   -1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769   -0.6410   -1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9436   -3.2174   -0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413   -3.3036    0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8666   -2.0589    0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -2.5883    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -1.0871   -1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971   -2.5113   -0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782   -1.4989    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284   -0.0903    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 14  2  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  1
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
M  END


  Mrv1652304282206172D          

 17 18  0  0  1  0            999 V2000
    4.1977    0.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6010   -0.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4259   -0.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4076   -1.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5827   -1.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1611   -2.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3361   -2.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9328   -1.4167    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1515   -1.1517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1621   -0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4761    0.1315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511    0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544   -0.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3727    0.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8475    0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
  1 15  1  0  0  0  0
  7 16  1  0  0  0  0
  3 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CCC2=C[C@H](C\C(C)=C\CC1)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-11-5-3-7-12(2)9-14-10-13(8-4-6-11)15(16)17-14/h6-7,10,14H,3-5,8-9H2,1-2H3/b11-6+,12-7+/t14-/m0/s1

> <INCHI_KEY>
JOQILOMKLDOWGX-RSPBECQPSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.323

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.4051639374018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E,8E,11S)-5,9-dimethyl-12-oxabicyclo[9.2.1]tetradeca-1(14),4,8-trien-13-one

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
3.8378288149999995

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.660684630091477

> <JCHEM_PKA_STRONGEST_BASIC>
-6.881923488786097

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
71.1483

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E,8E,11S)-5,9-dimethyl-12-oxabicyclo[9.2.1]tetradeca-1(14),4,8-trien-13-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.836   1.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.589  -0.017   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.128  -0.037   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.881  -1.380   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.094  -2.704   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.554  -2.684   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.767  -4.008   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.227  -3.988   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.475  -2.644   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.016  -2.150   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.036  -0.610   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.755   0.245   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.509   0.023   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.262  -1.321   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.296   1.346   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.520  -5.351   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.915   1.287   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13    1                                                       
CONECT   16    7                                                            
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3230 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

(4E,8E,11S)-5,9-dimethyl-12-oxabicyclo[9.2.1]tetradeca-1(14),4,8-trien-13-one

Traditional Name

(4E,8E,11S)-5,9-dimethyl-12-oxabicyclo[9.2.1]tetradeca-1(14),4,8-trien-13-one

CAS Registry Number

Not Available

SMILES

C\C1=C/CCC2=C[C@H](C\C(C)=C\CC1)OC2=O

InChI Identifier

InChI=1S/C15H20O2/c1-11-5-3-7-12(2)9-14-10-13(8-4-6-11)15(16)17-14/h6-7,10,14H,3-5,8-9H2,1-2H3/b11-6+,12-7+/t14-/m0/s1

InChI Key

JOQILOMKLDOWGX-RSPBECQPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aristolochia cucurbitafolia	Plant	KNApSAcK
Aristolochia cucurbitifolia	LOTUS Database	35616633
Aristolochia heterophylla	LOTUS Database	35616633
Aristolochia heterophylla Hemsl	Plant	KNApSAcK
Aristolochia manshuriensis	Plant	KNApSAcK
Aristolochia mollissima	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.14	ALOGPS
logP	3.84	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.15 m³·mol⁻¹	ChemAxon
Polarizability	25.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00012469

Chemspider ID

29419762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14527198

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bu MM, Yu SQ, Dong CZ: [Chemical constituents from fruits of Aristolochia mollissima and their nematicidal activity against root-knot nematode]. Zhongguo Zhong Yao Za Zhi. 2018 Aug;43(16):3307-3314. doi: 10.19540/j.cnki.cjcmm.20180514.001. [PubMed:30200734 ]
Schaubach S, Gebauer K, Ungeheuer F, Hoffmeister L, Ilg MK, Wirtz C, Furstner A: A Two-Component Alkyne Metathesis Catalyst System with an Improved Substrate Scope and Functional Group Tolerance: Development and Applications to Natural Product Synthesis. Chemistry. 2016 Jun 13;22(25):8494-507. doi: 10.1002/chem.201601163. Epub 2016 May 20. [PubMed:27203803 ]

Showing NP-Card for Manshurolide (NP0058997)

MOL for NP0058997 (Manshurolide)

3D MOL for NP0058997 (Manshurolide)

3D SDF for NP0058997 (Manshurolide)

3D-SDF for NP0058997 (Manshurolide)

PDB for NP0058997 (Manshurolide)

3D PDB for NP0058997 (Manshurolide)

SMILES for NP0058997 (Manshurolide)

INCHI for NP0058997 (Manshurolide)

Structure for NP0058997 (Manshurolide)

3D Structure for NP0058997 (Manshurolide)