NP-MRD: Showing NP-Card for Cicholosumin G (NP0333675)

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Record Information

Version

2.0

Created at

2024-07-31 23:48:33 UTC

Updated at

2026-02-22 09:04:56 UTC

NP-MRD ID

NP0333675

Natural Product DOI

https://doi.org/10.57994/3154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cicholosumin G

Description

Cicholosumin G belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11. Cicholosumin G was first documented in 2024 (PMID: 39032793). Based on a literature review very few articles have been published on Cicholosumin G.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04152302222D          

 21 23  0  0  1  0            999 V2000
    4.2989    2.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409    2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553    1.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770    1.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013    0.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9800    0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0539   -0.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025   -0.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001    2.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2717    0.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284    0.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    0.7547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0769    0.3315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5718   -0.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4722   -0.2296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556    0.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7799    1.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513    0.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302    1.2690    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    1.5590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1159    2.2040    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  2  0  0  0  0
  3 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 19  1  1  0  0  0
 12 20  1  0  0  0  0
 20 17  1  1  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333675

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C=C3C(CO)=CC(=O)C3=C(C)C[C@@H]1OC(=O)[C@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-7-3-12-10(15(2,19)14(18)20-12)5-9-8(6-16)4-11(17)13(7)9/h4-5,10,12,16,19H,3,6H2,1-2H3/t10-,12-,15+/m0/s1

> <INCHI_KEY>
GMVITULQUCTRDQ-ITDIGPHOSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.227928397784417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,9aS)-3-hydroxy-5-(hydroxymethyl)-3,8-dimethyl-2H,3H,3aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione

> <JCHEM_LOGP>
-0.2374968213333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.057632925029333

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.224615964899073

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7739610816916533

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
72.9502

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,9aS)-3-hydroxy-5-(hydroxymethyl)-3,8-dimethyl-3aH,9H,9aH-azuleno[6,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-23         0                                  
HETATM    1  C   UNK     0       8.025   5.502   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.356   4.114   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.317   2.910   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.850   3.048   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.456   1.632   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.296   0.619   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.434  -0.915   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.831  -1.562   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      10.640   4.370   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.974   1.409   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.586   0.741   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.199   1.409   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.877   0.619   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.801  -0.613   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.748  -0.429   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.717   1.632   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.322   3.048   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.216   1.289   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       6.403   2.369   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       4.856   2.910   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.816   4.114   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4                                                            
CONECT   10    3    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19   20                                             
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16   20                                                       
CONECT   18   16                                                            
CONECT   19   12                                                            
CONECT   20   12   17   21                                                  
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₅

Average Mass

276.2880 Da

Monoisotopic Mass

276.09977 Da

IUPAC Name

(3R,3aS,9aS)-3-hydroxy-5-(hydroxymethyl)-3,8-dimethyl-2H,3H,3aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione

Traditional Name

(3R,3aS,9aS)-3-hydroxy-5-(hydroxymethyl)-3,8-dimethyl-3aH,9H,9aH-azuleno[6,5-b]furan-2,7-dione

CAS Registry Number

Not Available

SMILES

[H][C@]12C=C3C(CO)=CC(=O)C3=C(C)C[C@@H]1OC(=O)[C@]2(C)O

InChI Identifier

InChI=1S/C15H16O5/c1-7-3-12-10(15(2,19)14(18)20-12)5-9-8(6-16)4-11(17)13(7)9/h4-5,10,12,16,19H,3,6H2,1-2H3/t10-,12-,15+/m0/s1

InChI Key

GMVITULQUCTRDQ-ITDIGPHOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	XinJiang Technical Institute of Physics and Chemistry Chinese Academy of Sciences	Zheyang Wei	2024-07-31	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	[email protected]	XinJiang Technical Institute of Physics and Chemistry Chinese Academy of Sciences	Zheyang Wei	2024-07-31	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Cichorium glandulosum		Not Available
Cichorium glandulosum		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Xanthanolides

Alternative Parents

Substituents

Xanthanolide-skeleton
Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty alcohol ester
Fatty alcohol
Fatty acid ester
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Gamma butyrolactone
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Tertiary alcohol
Enone
Acryloyl-group
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	-0.24	ChemAxon
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.95 m³·mol⁻¹	ChemAxon
Polarizability	28.23 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

Wei Z, Turak A, Li B, Aisa HA: Guaianolide sesquiterpene lactones from Cichorium glandulosum and their anti-neuroinflammation activities. Phytochemistry. 2024 Jul 19;226:114223. doi: 10.1016/j.phytochem.2024.114223. [PubMed:39032793 ]
DOI: 10.1016/j.phytochem.2024.114223
PII: s0031942224002607

Showing NP-Card for Cicholosumin G (NP0333675)

MOL for NP0333675 (Cicholosumin G)

3D MOL for NP0333675 (Cicholosumin G)

3D SDF for NP0333675 (Cicholosumin G)

3D-SDF for NP0333675 (Cicholosumin G)

PDB for NP0333675 (Cicholosumin G)

3D PDB for NP0333675 (Cicholosumin G)

SMILES for NP0333675 (Cicholosumin G)

INCHI for NP0333675 (Cicholosumin G)

Structure for NP0333675 (Cicholosumin G)

3D Structure for NP0333675 (Cicholosumin G)