NP-MRD: Showing NP-Card for ajucampylanoid T (NP0333085)

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Record Information

Version

2.0

Created at

2024-05-08 21:55:57 UTC

Updated at

2024-09-03 04:21:09 UTC

NP-MRD ID

NP0333085

Natural Product DOI

https://doi.org/10.57994/2384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajucampylanoid T

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212300322D          

 28 30  0  0  1  0            999 V2000
    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  2  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
    1.6771   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304   -3.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394   -4.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -4.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650   -5.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5065   -6.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640   -6.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -4.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429   -4.7988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4675   -2.9320    0.0000 O   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
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  6  0  0  0
 20 18  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 20  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
 22 28  2  0  0  0  0
M  END


  Mrv2104 01212300322D          

 28 30  0  0  1  0            999 V2000
    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  2  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
    1.6771   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304   -3.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394   -4.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -4.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650   -5.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5065   -6.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640   -6.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -4.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429   -4.7988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4675   -2.9320    0.0000 O   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
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  6  0  0  0
 20 18  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 20  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
 22 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333085

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCCC(=C)[C@]1(C)[C@@H](O)C[C@@H](C)[C@]2(C)CCC1C(O)C(OCC)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O5/c1-6-26-20-18(24)15(19(25)27-20)10-11-21(4)14(3)12-17(23)22(5)13(2)8-7-9-16(21)22/h14-18,20,23-24H,2,6-12H2,1,3-5H3/t14-,15?,16-,17+,18?,20?,21+,22+/m1/s1

> <INCHI_KEY>
QFSXIAHSEUEGRR-ULLDDFLPSA-N

> <FORMULA>
C22H36O5

> <MOLECULAR_WEIGHT>
380.525

> <EXACT_MASS>
380.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
43.579729142003615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-5-ethoxy-4-hydroxyoxolan-2-one

> <JCHEM_LOGP>
3.495082312000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.905378922243026

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4673861255800567

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
102.80959999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-{2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-5-ethoxy-4-hydroxyoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.131  -5.707   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.120  -6.887   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.657  -6.779   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.234  -8.207   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.054  -9.197   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.161 -10.733   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.545 -11.408   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.653 -12.944   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.748  -8.381   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.320  -8.958   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.473  -5.473   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    8    5   13                                                  
CONECT   13   12                                                            
CONECT   14    6                                                            
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20    2   27                                             
CONECT   27   26                                                            
CONECT   28   22                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₆O₅

Average Mass

380.5250 Da

Monoisotopic Mass

380.25627 Da

IUPAC Name

3-{2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-5-ethoxy-4-hydroxyoxolan-2-one

Traditional Name

3-{2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-5-ethoxy-4-hydroxyoxolan-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)CCC1C(O)C(OCC)OC1=O

InChI Identifier

InChI=1S/C22H36O5/c1-6-26-20-18(24)15(19(25)27-20)10-11-21(4)14(3)12-17(23)22(5)13(2)8-7-9-16(21)22/h14-18,20,23-24H,2,6-12H2,1,3-5H3/t14-,15?,16-,17+,18?,20?,21+,22+/m1/s1

InChI Key

QFSXIAHSEUEGRR-ULLDDFLPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	pengsh56@mail2.sysu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 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
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 acid ester
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Gamma butyrolactone
Tetrahydrofuran
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)	12.91	ChemAxon
pKa (Strongest Basic)	-0.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.81 m³·mol⁻¹	ChemAxon
Polarizability	43.58 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 ]

Showing NP-Card for ajucampylanoid T (NP0333085)

MOL for NP0333085 (ajucampylanoid T)

3D MOL for NP0333085 (ajucampylanoid T)

3D SDF for NP0333085 (ajucampylanoid T)

3D-SDF for NP0333085 (ajucampylanoid T)

PDB for NP0333085 (ajucampylanoid T)

3D PDB for NP0333085 (ajucampylanoid T)

SMILES for NP0333085 (ajucampylanoid T)

INCHI for NP0333085 (ajucampylanoid T)

Structure for NP0333085 (ajucampylanoid T)

3D Structure for NP0333085 (ajucampylanoid T)