NP-MRD: Showing NP-Card for ajucampylanoid J (NP0333075)

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Record Information

Version

2.0

Created at

2024-05-08 21:17:40 UTC

Updated at

2024-09-03 04:21:07 UTC

NP-MRD ID

NP0333075

Natural Product DOI

https://doi.org/10.57994/2374

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajucampylanoid J

Description

Ajucampylanoid J belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. ajucampylanoid J was first documented in 2023 (PMID: 37566645). Based on a literature review very few articles have been published on ajucampylanoid J.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01202323542D          

 25 27  0  0  1  0            999 V2000
   -1.0017   -4.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9442   -4.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -3.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -2.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7043   -2.0135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445   -3.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  6  0  0  0
 17 15  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  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
 23 22  1  0  0  0  0
 23 17  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  1  0  0  0
 19 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCCC(=C)[C@]1(C)[C@@H](O)C[C@@H](C)[C@]2(C)CCC1=CC(=O)OC1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-12-6-5-7-15-19(3,13(2)10-16(21)20(12,15)4)9-8-14-11-17(22)24-18(14)23/h11,13,15-16,18,21,23H,1,5-10H2,2-4H3/t13-,15-,16+,18?,19+,20+/m1/s1

> <INCHI_KEY>
ULLNNMZEEFFTNG-ZJMWWDIHSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.46212502340306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-5-hydroxy-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
3.501583277000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.800284743124598

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.974692755671862

> <JCHEM_PKA_STRONGEST_BASIC>
-0.46744478716189547

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
92.74909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-5-hydroxy-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JAN-23         0                                  
HETATM    1  O   UNK     0      -1.870  -9.019   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.762  -7.482   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.942  -6.492   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.365  -5.065   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.181  -3.759   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.456  -6.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.829  -5.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.161  -3.992   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    4    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   23                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   10   24                                             
CONECT   24   23                                                            
CONECT   25   19                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

4-{2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-5-hydroxy-2,5-dihydrofuran-2-one

Traditional Name

4-{2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-5-hydroxy-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

[H][C@]12CCCC(=C)[C@]1(C)[C@@H](O)C[C@@H](C)[C@]2(C)CCC1=CC(=O)OC1O

InChI Identifier

InChI=1S/C20H30O4/c1-12-6-5-7-15-19(3,13(2)10-16(21)20(12,15)4)9-8-14-11-17(22)24-18(14)23/h11,13,15-16,18,21,23H,1,5-10H2,2-4H3/t13-,15-,16+,18?,19+,20+/m1/s1

InChI Key

ULLNNMZEEFFTNG-ZJMWWDIHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ajuga campylantha		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Clerodane diterpenoid
Diterpenoid
Diterpene lactone
Fatty alcohol ester
Fatty acid ester
Fatty acyl
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
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	3.5	ChemAxon
pKa (Strongest Acidic)	9.97	ChemAxon
pKa (Strongest Basic)	-0.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.75 m³·mol⁻¹	ChemAxon
Polarizability	37.46 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

Peng X, Tan Q, Zhang Z, Wu D, Xu J, Zhou H, Gu Q: Discovery of neo-Clerodane Diterpenoids from Ajuga campylantha as Neuroprotective Agents against Ferroptosis and Neuroinflammation. J Nat Prod. 2023 Aug 25;86(8):2006-2021. doi: 10.1021/acs.jnatprod.3c00447. Epub 2023 Aug 11. [PubMed:37566645 ]
DOI: 10.1021/acs.jnatprod.3c00447

Showing NP-Card for ajucampylanoid J (NP0333075)

MOL for NP0333075 (ajucampylanoid J)

3D MOL for NP0333075 (ajucampylanoid J)

3D SDF for NP0333075 (ajucampylanoid J)

3D-SDF for NP0333075 (ajucampylanoid J)

PDB for NP0333075 (ajucampylanoid J)

3D PDB for NP0333075 (ajucampylanoid J)

SMILES for NP0333075 (ajucampylanoid J)

INCHI for NP0333075 (ajucampylanoid J)

Structure for NP0333075 (ajucampylanoid J)

3D Structure for NP0333075 (ajucampylanoid J)