NP-MRD: Showing NP-Card for waixenicin a (NP0239649)

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Record Information

Version

2.0

Created at

2022-09-06 23:17:17 UTC

Updated at

2022-09-06 23:17:17 UTC

NP-MRD ID

NP0239649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

waixenicin a

Description

Waixenicin A belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. waixenicin a is found in Sarcothelia edmondsoni. waixenicin a was first documented in 2019 (PMID: 31219801). Based on a literature review a small amount of articles have been published on waixenicin A (PMID: 33080445) (PMID: 32994545) (PMID: 32430797) (PMID: 31947967).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201172D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072201172D          

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M  END
> <DATABASE_ID>
NP0239649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC\C(C)=C\C[C@H](OC(C)=O)C1=CO[C@H](OC(C)=O)[C@@H]2[C@@H]1CCC(C)=CCCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O7/c1-16-8-7-9-18(3)25-22(12-10-16)23(15-31-26(25)33-21(6)29)24(32-20(5)28)13-11-17(2)14-30-19(4)27/h8,11,15,22,24-26H,3,7,9-10,12-14H2,1-2,4-6H3/b16-8?,17-11+/t22-,24+,25+,26-/m1/s1

> <INCHI_KEY>
DCZJIZRGTZFSQY-VWQHOESYSA-N

> <FORMULA>
C26H36O7

> <MOLECULAR_WEIGHT>
460.567

> <EXACT_MASS>
460.246103499

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.15527870657255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,5S)-5-[(1R,4aS,11aR)-1-(acetyloxy)-7-methyl-11-methylidene-1H,4aH,5H,6H,9H,10H,11H,11aH-cyclonona[c]pyran-4-yl]-5-(acetyloxy)-2-methylpent-2-en-1-yl acetate

> <JCHEM_LOGP>
3.455111736333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.887330189251623

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
125.10969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,5S)-5-[(1R,4aS,11aR)-1-(acetyloxy)-7-methyl-11-methylidene-1H,4aH,5H,6H,9H,10H,11aH-cyclonona[c]pyran-4-yl]-5-(acetyloxy)-2-methylpent-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.220  -2.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.990  -1.180   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.990   2.720   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.506   2.987   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.774   4.504   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.840   2.217   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.367   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.840  -0.677   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.174  -1.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.508  -0.677   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.508   0.863   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.841   1.633   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.841   3.173   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.508   3.943   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.175   3.943   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.509   3.173   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.842   3.943   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.176   3.173   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.842   5.483   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.841  -1.447   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.175  -0.677   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.175   0.863   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.509  -1.447   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.174  -2.987   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.840  -3.757   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.506  -2.987   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.173  -3.757   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.173  -5.297   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.161  -6.067   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.506  -6.067   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.506  -1.447   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12   26                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   12   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   11   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28    2   10                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₇

Average Mass

460.5670 Da

Monoisotopic Mass

460.24610 Da

IUPAC Name

(2E,5S)-5-[(1R,4aS,11aR)-1-(acetyloxy)-7-methyl-11-methylidene-1H,4aH,5H,6H,9H,10H,11H,11aH-cyclonona[c]pyran-4-yl]-5-(acetyloxy)-2-methylpent-2-en-1-yl acetate

Traditional Name

(2E,5S)-5-[(1R,4aS,11aR)-1-(acetyloxy)-7-methyl-11-methylidene-1H,4aH,5H,6H,9H,10H,11aH-cyclonona[c]pyran-4-yl]-5-(acetyloxy)-2-methylpent-2-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC\C(C)=C\C[C@H](OC(C)=O)C1=CO[C@H](OC(C)=O)[C@@H]2[C@@H]1CCC(C)=CCCC2=C

InChI Identifier

InChI=1S/C26H36O7/c1-16-8-7-9-18(3)25-22(12-10-16)23(15-31-26(25)33-21(6)29)24(32-20(5)28)13-11-17(2)14-30-19(4)27/h8,11,15,22,24-26H,3,7,9-10,12-14H2,1-2,4-6H3/b16-8?,17-11+/t22-,24+,25+,26-/m1/s1

InChI Key

DCZJIZRGTZFSQY-VWQHOESYSA-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
Sarcothelia edmondsoni	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Tricarboxylic acid or derivatives
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
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	3.46	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	125.11 m³·mol⁻¹	ChemAxon
Polarizability	50.16 Å³	ChemAxon
Number of Rings	2	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

73755210

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wong R, Gong H, Alanazi R, Bondoc A, Luck A, Sabha N, Horgen FD, Fleig A, Rutka JT, Feng ZP, Sun HS: Inhibition of TRPM7 with waixenicin A reduces glioblastoma cellular functions. Cell Calcium. 2020 Dec;92:102307. doi: 10.1016/j.ceca.2020.102307. Epub 2020 Oct 14. [PubMed:33080445 ]
Sun HS, Horgen FD, Romo D, Hull KG, Kiledal SA, Fleig A, Feng ZP: Waixenicin A, a marine-derived TRPM7 inhibitor: a promising CNS drug lead. Acta Pharmacol Sin. 2020 Dec;41(12):1519-1524. doi: 10.1038/s41401-020-00512-4. Epub 2020 Sep 29. [PubMed:32994545 ]
Turlova E, Wong R, Xu B, Li F, Du L, Habbous S, Horgen FD, Fleig A, Feng ZP, Sun HS: TRPM7 Mediates Neuronal Cell Death Upstream of Calcium/Calmodulin-Dependent Protein Kinase II and Calcineurin Mechanism in Neonatal Hypoxic-Ischemic Brain Injury. Transl Stroke Res. 2021 Feb;12(1):164-184. doi: 10.1007/s12975-020-00810-3. Epub 2020 May 19. [PubMed:32430797 ]
Liu H, Dilger JP, Lin J: The Role of Transient Receptor Potential Melastatin 7 (TRPM7) in Cell Viability: A Potential Target to Suppress Breast Cancer Cell Cycle. Cancers (Basel). 2020 Jan 4;12(1):131. doi: 10.3390/cancers12010131. [PubMed:31947967 ]
Xing J, Wang M, Hong J, Gao Y, Liu Y, Gu H, Dong J, Li L: TRPM7 channel inhibition exacerbates pulmonary arterial hypertension through MEK/ERK pathway. Aging (Albany NY). 2019 Jun 19;11(12):4050-4065. doi: 10.18632/aging.102036. [PubMed:31219801 ]
LOTUS database [Link]

Showing NP-Card for waixenicin a (NP0239649)

MOL for NP0239649 (waixenicin a)

3D MOL for NP0239649 (waixenicin a)

3D SDF for NP0239649 (waixenicin a)

3D-SDF for NP0239649 (waixenicin a)

PDB for NP0239649 (waixenicin a)

3D PDB for NP0239649 (waixenicin a)

SMILES for NP0239649 (waixenicin a)

INCHI for NP0239649 (waixenicin a)

Structure for NP0239649 (waixenicin a)

3D Structure for NP0239649 (waixenicin a)