NP-MRD: Showing NP-Card for ajucampylanoid U (NP0333086)

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Record Information

Version

2.0

Created at

2024-05-08 21:59:26 UTC

Updated at

2024-09-03 04:21:09 UTC

NP-MRD ID

NP0333086

Natural Product DOI

https://doi.org/10.57994/2385

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajucampylanoid U

Description

Ajucampylanoid U belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. ajucampylanoid U was first documented in 2023 (PMID: 37566645). Based on a literature review very few articles have been published on ajucampylanoid U.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212300352D          

 15 16  0  0  1  0            999 V2000
   -0.0404   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    1.3686    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666    1.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1487   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    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
  4  6  2  0  0  0  0
  7  3  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333086

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=O)C1=C(C)C[C@@H]2O[C@@H](C[C@H]12)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O3/c1-3-13-11-5-8-9(6-12)7(2)4-10(8)14-11/h6,8,10-11H,3-5H2,1-2H3/t8-,10+,11+/m1/s1

> <INCHI_KEY>
GGVHVSWWMQXKJX-MIMYLULJSA-N

> <FORMULA>
C11H16O3

> <MOLECULAR_WEIGHT>
196.246

> <EXACT_MASS>
196.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.75491193087251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3aR,6aS)-2-ethoxy-5-methyl-2H,3H,3aH,6H,6aH-cyclopenta[b]furan-4-carbaldehyde

> <JCHEM_LOGP>
0.9355775289999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9455307752102717

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
53.27820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3aR,6aS)-2-ethoxy-5-methyl-2H,3H,3aH,6H,6aH-cyclopenta[b]furan-4-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 21-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-23         0                                  
HETATM    1  C   UNK     0      -0.075  -0.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.894   2.235   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       0.388   2.555   0.000  0.00  0.00           H+0
HETATM    6  O   UNK     0       2.924   3.379   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.744  -0.476   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.514  -1.810   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.054  -1.810   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.299  -1.722   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    9   14                                                       
CONECT   14    7   13   15                                                  
CONECT   15   14    2                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆O₃

Average Mass

196.2460 Da

Monoisotopic Mass

196.10994 Da

IUPAC Name

(2S,3aR,6aS)-2-ethoxy-5-methyl-2H,3H,3aH,6H,6aH-cyclopenta[b]furan-4-carbaldehyde

Traditional Name

(2S,3aR,6aS)-2-ethoxy-5-methyl-2H,3H,3aH,6H,6aH-cyclopenta[b]furan-4-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H]C(=O)C1=C(C)C[C@@H]2O[C@@H](C[C@H]12)OCC

InChI Identifier

InChI=1S/C11H16O3/c1-3-13-11-5-8-9(6-12)7(2)4-10(8)14-11/h6,8,10-11H,3-5H2,1-2H3/t8-,10+,11+/m1/s1

InChI Key

GGVHVSWWMQXKJX-MIMYLULJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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
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
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 iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

11-noriridane monoterpenoid
Bicyclic monoterpenoid
Tetrahydrofuran
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	0.94	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.28 m³·mol⁻¹	ChemAxon
Polarizability	21.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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 U (NP0333086)

MOL for NP0333086 (ajucampylanoid U)

3D MOL for NP0333086 (ajucampylanoid U)

3D SDF for NP0333086 (ajucampylanoid U)

3D-SDF for NP0333086 (ajucampylanoid U)

PDB for NP0333086 (ajucampylanoid U)

3D PDB for NP0333086 (ajucampylanoid U)

SMILES for NP0333086 (ajucampylanoid U)

INCHI for NP0333086 (ajucampylanoid U)

Structure for NP0333086 (ajucampylanoid U)

3D Structure for NP0333086 (ajucampylanoid U)