NP-MRD: Showing NP-Card for chaetovirexylarione E (NP0341822)

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Record Information

Version

2.0

Created at

2024-09-21 06:55:15 UTC

Updated at

2025-06-12 01:07:57 UTC

NP-MRD ID

NP0341822

Natural Product DOI

https://doi.org/10.57994/3308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chaetovirexylarione E

Description

Chaetovirexylarione E belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Based on a literature review very few articles have been published on chaetovirexylarione E.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 06052309272D          

 28 31  0  0  1  0            999 V2000
    1.0930   -2.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -2.3740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608   -1.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232   -1.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911    0.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481   -0.0792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5535    0.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2159    1.2321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1213    2.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9730    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676    0.0847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8247   -0.2431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052   -0.4071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4998   -1.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7428   -0.8988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1626   -1.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -1.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715    0.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091   -0.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0520   -0.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997    1.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8943    1.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6198    1.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393    1.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037   -1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  6  0  0  0
 14 12  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  6  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  4 18  1  0  0  0  0
  5 19  2  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
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 28  2  0  0  0  0
  3 28  1  0  0  0  0
M  END


  Mrv2104 06052309272D          

 28 31  0  0  1  0            999 V2000
    1.0930   -2.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -2.3740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608   -1.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232   -1.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911    0.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481   -0.0792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5535    0.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2159    1.2321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1213    2.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9730    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676    0.0847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8247   -0.2431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052   -0.4071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4998   -1.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7428   -0.8988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1626   -1.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -1.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715    0.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091   -0.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0520   -0.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997    1.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8943    1.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6198    1.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393    1.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037   -1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  6  0  0  0
 14 12  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  6  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  4 18  1  0  0  0  0
  5 19  2  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
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 28  2  0  0  0  0
  3 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0341822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C[C@@H](C)[C@]3(O[C@@H](C)C[C@H](O)[C@@H]3O)OC2=C2C(=O)C=C(CO)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O8/c1-9-4-12-15(25-3)7-16-17(13(22)6-11(8-21)26-16)18(12)28-20(9)19(24)14(23)5-10(2)27-20/h6-7,9-10,14,19,21,23-24H,4-5,8H2,1-3H3/t9-,10+,14+,19+,20+/m1/s1

> <INCHI_KEY>
FFLBTXNGZDCIJD-CHAVOOBZSA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.13369920916377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,3'R,4S,6S)-3,4-dihydroxy-8'-(hydroxymethyl)-5'-methoxy-3',6-dimethyl-4',10'-dihydro-3'H-spiro[oxane-2,2'-pyrano[2,3-f]chromen]-10'-one

> <JCHEM_LOGP>
0.8019295043333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.221517616792417

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.294706873446062

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0834411705724794

> <JCHEM_POLAR_SURFACE_AREA>
114.68

> <JCHEM_REFRACTIVITY>
99.14359999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,3'R,4S,6S)-3,4-dihydroxy-8'-(hydroxymethyl)-5'-methoxy-3',6-dimethyl-3',4'-dihydrospiro[oxane-2,2'-pyrano[2,3-f]chromen]-10'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-JUN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-23         0                                  
HETATM    1  C   UNK     0       2.040  -5.349   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.277  -4.431   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.100  -2.902   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.337  -1.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.160  -0.454   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.397   0.464   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.810  -0.148   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.633   1.382   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.870   2.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.693   3.830   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.283   1.688   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.460   0.158   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.873  -0.454   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.223  -0.760   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.400  -2.290   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.986  -1.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.770  -3.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.750  -2.596   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.747   0.158   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.510  -0.760   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.097  -0.148   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.080   1.382   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.493   1.994   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.669   3.524   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.157   2.300   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.570   1.688   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.807   2.606   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.687  -2.290   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14   16                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14                                                            
CONECT   16    7   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    4                                                       
CONECT   19    5   20   26                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   19   27                                                  
CONECT   27   26                                                            
CONECT   28   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

(2S,3S,3'R,4S,6S)-3,4-dihydroxy-8'-(hydroxymethyl)-5'-methoxy-3',6-dimethyl-4',10'-dihydro-3'H-spiro[oxane-2,2'-pyrano[2,3-f]chromen]-10'-one

Traditional Name

(2S,3S,3'R,4S,6S)-3,4-dihydroxy-8'-(hydroxymethyl)-5'-methoxy-3',6-dimethyl-3',4'-dihydrospiro[oxane-2,2'-pyrano[2,3-f]chromen]-10'-one

CAS Registry Number

Not Available

SMILES

COC1=C2C[C@@H](C)[C@]3(O[C@@H](C)C[C@H](O)[C@@H]3O)OC2=C2C(=O)C=C(CO)OC2=C1

InChI Identifier

InChI=1S/C20H24O8/c1-9-4-12-15(25-3)7-16-17(13(22)6-11(8-21)26-16)18(12)28-20(9)19(24)14(23)5-10(2)27-20/h6-7,9-10,14,19,21,23-24H,4-5,8H2,1-3H3/t9-,10+,14+,19+,20+/m1/s1

InChI Key

FFLBTXNGZDCIJD-CHAVOOBZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	sitian_zhang@163.com	huazhong university of science and technology	sitian zhang	2024-09-21	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	sitian_zhang@163.com	huazhong university of science and technology	sitian zhang	2024-09-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	sitian_zhang@163.com	huazhong university of science and technology	sitian zhang	2024-09-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	sitian_zhang@163.com	huazhong university of science and technology	sitian zhang	2024-09-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	sitian_zhang@163.com	huazhong university of science and technology	sitian zhang	2024-09-21	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	sitian_zhang@163.com	huazhong university of science and technology	sitian zhang	2024-09-21	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	sitian_zhang@163.com	huazhong university of science and technology	sitian zhang	2024-09-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.203706235 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.203706235, CDCl₃, simulated)	sitian_zhang@163.com	huazhong university of science and technology	sitian zhang	2024-09-21	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Long-chain fatty alcohols

Alternative Parents

Substituents

Long chain fatty alcohol
Chromone
1-benzopyran
Benzopyran
Chromane
Anisole
Ketal
Pyranone
Dihydropyranone
Alkyl aryl ether
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
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	0.8	ChemAxon
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.14 m³·mol⁻¹	ChemAxon
Polarizability	40.13 Å³	ChemAxon
Number of Rings	4	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

Showing NP-Card for chaetovirexylarione E (NP0341822)

MOL for NP0341822 (chaetovirexylarione E)

3D MOL for NP0341822 (chaetovirexylarione E)

3D SDF for NP0341822 (chaetovirexylarione E)

3D-SDF for NP0341822 (chaetovirexylarione E)

PDB for NP0341822 (chaetovirexylarione E)

3D PDB for NP0341822 (chaetovirexylarione E)

SMILES for NP0341822 (chaetovirexylarione E)

INCHI for NP0341822 (chaetovirexylarione E)

Structure for NP0341822 (chaetovirexylarione E)

3D Structure for NP0341822 (chaetovirexylarione E)