NP-MRD: Showing NP-Card for Cicholosumin F (NP0333674)

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Record Information

Version

2.0

Created at

2024-07-31 23:48:03 UTC

Updated at

2025-02-11 15:49:29 UTC

NP-MRD ID

NP0333674

Natural Product DOI

https://doi.org/10.57994/3153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cicholosumin F

Description

Cicholosumin F belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Cicholosumin F was first documented in 2024 (PMID: 39032793). Based on a literature review very few articles have been published on Cicholosumin F.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04152302212D          

 26 27  0  0  1  0            999 V2000
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524    0.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774    0.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9899   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9899    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774    1.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6713   -1.5938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3699   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871   -1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7885   -0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015   -2.1159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4509   -0.1509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    1.2466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 11  2  0  0  0  0
 12  4  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END


  Mrv2104 04152302212D          

 26 27  0  0  1  0            999 V2000
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524    0.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774    0.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9899   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9899    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774    1.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6713   -1.5938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3699   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871   -1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7885   -0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015   -2.1159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4509   -0.1509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    1.2466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 11  2  0  0  0  0
 12  4  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333674

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@@H](C)C[C@H](OC(=O)C(\C)=C/C)[C@H](C=C1C(C)=CC2=O)[C@H](C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-6-10(2)20(24)25-17-8-12(4)18-14(11(3)7-16(18)21)9-15(17)13(5)19(22)23/h6-7,9,12-13,15,17-18H,8H2,1-5H3,(H,22,23)/b10-6-/t12-,13-,15+,17-,18+/m0/s1

> <INCHI_KEY>
DLYIKCIVKQLMFI-DKMZTISNSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.3211141276714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(5R,6S,8S,8aR)-3,8-dimethyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-1-oxo-1,5,6,7,8,8a-hexahydroazulen-5-yl]propanoic acid

> <JCHEM_LOGP>
3.724740155333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.482295485635555

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.481859185352635

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7985673268905105

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
96.35599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(5R,6S,8S,8aR)-3,8-dimethyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-1-oxo-6,7,8,8a-tetrahydro-5H-azulen-5-yl]propanoic acid

> <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       5.916   2.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.968  -0.384   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.738   0.950   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.278   0.950   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.048  -0.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.048   2.284   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.278   3.617   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.968   2.284   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.720  -2.975   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.157  -4.409   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.243  -2.746   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.805  -1.312   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      11.203  -3.950   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       6.442  -0.282   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.114  -3.094   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.114   2.327   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    6                                                            
CONECT   12    4   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19    2   21   25                                             
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

(2S)-2-[(5R,6S,8S,8aR)-3,8-dimethyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-1-oxo-1,5,6,7,8,8a-hexahydroazulen-5-yl]propanoic acid

Traditional Name

(2S)-2-[(5R,6S,8S,8aR)-3,8-dimethyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-1-oxo-6,7,8,8a-tetrahydro-5H-azulen-5-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@@H](C)C[C@H](OC(=O)C(\C)=C/C)[C@H](C=C1C(C)=CC2=O)[C@H](C)C(O)=O

InChI Identifier

InChI=1S/C20H26O5/c1-6-10(2)20(24)25-17-8-12(4)18-14(11(3)7-16(18)21)9-15(17)13(5)19(22)23/h6-7,9,12-13,15,17-18H,8H2,1-5H3,(H,22,23)/b10-6-/t12-,13-,15+,17-,18+/m0/s1

InChI Key

DLYIKCIVKQLMFI-DKMZTISNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	weizheyang1002@126.com	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, 600.23370642, CD₃OD, simulated)	weizheyang1002@126.com	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

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Methyl-branched fatty acid
Fatty acid ester
Branched fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Acryloyl-group
Ketone
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.72	ChemAxon
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.36 m³·mol⁻¹	ChemAxon
Polarizability	37.32 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

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 F (NP0333674)

MOL for NP0333674 (Cicholosumin F)

3D MOL for NP0333674 (Cicholosumin F)

3D SDF for NP0333674 (Cicholosumin F)

3D-SDF for NP0333674 (Cicholosumin F)

PDB for NP0333674 (Cicholosumin F)

3D PDB for NP0333674 (Cicholosumin F)

SMILES for NP0333674 (Cicholosumin F)

INCHI for NP0333674 (Cicholosumin F)

Structure for NP0333674 (Cicholosumin F)

3D Structure for NP0333674 (Cicholosumin F)