NP-MRD: Showing NP-Card for ajucampylanoid Q (NP0333082)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-05-08 21:45:06 UTC

Updated at

2024-09-03 04:21:08 UTC

NP-MRD ID

NP0333082

Natural Product DOI

https://doi.org/10.57994/2381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajucampylanoid Q

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212300212D          

 31 34  0  0  1  0            999 V2000
    0.8400   -2.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8735   -1.4350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0558   -1.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2575   -2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751   -2.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665   -3.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -2.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8749   -3.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6666   -3.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884   -2.1793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6449   -1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4970   -1.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230   -0.6489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1830   -0.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844   -0.2150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5399    0.3949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -1.0011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3258   -0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0814    0.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    1.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    1.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409   -1.1772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2170   -0.3712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8270   -0.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -1.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359   -2.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299   -2.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -1.6110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1240   -2.2210    0.0000 H   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  2  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
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  6  0  0  0
 18 16  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30  2  1  0  0  0  0
 30 31  1  1  0  0  0
M  END


  Mrv2104 01212300212D          

 31 34  0  0  1  0            999 V2000
    0.8400   -2.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8735   -1.4350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0558   -1.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2575   -2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751   -2.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665   -3.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -2.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8749   -3.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6666   -3.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884   -2.1793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6449   -1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4970   -1.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230   -0.6489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1830   -0.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844   -0.2150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5399    0.3949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -1.0011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3258   -0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0814    0.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    1.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    1.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409   -1.1772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2170   -0.3712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8270   -0.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -1.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359   -2.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299   -2.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -1.6110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1240   -2.2210    0.0000 H   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  2  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
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  6  0  0  0
 18 16  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30  2  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCC[C@]3(CO3)[C@]1(COC(C)=O)[C@@H](O)C[C@@H](C)[C@]2(C)CCC1=CC(OC)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O7/c1-14-10-18(25)23(13-28-15(2)24)17(6-5-8-22(23)12-29-22)21(14,3)9-7-16-11-19(27-4)30-20(16)26/h11,14,17-19,25H,5-10,12-13H2,1-4H3/t14-,17-,18+,19?,21+,22+,23+/m1/s1

> <INCHI_KEY>
QWYIPUHTKBEREI-LDSWVEIGSA-N

> <FORMULA>
C23H34O7

> <MOLECULAR_WEIGHT>
422.518

> <EXACT_MASS>
422.230453435

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.204464779240034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4aR,5S,6R,8S,8aR)-8-hydroxy-5-[2-(5-methoxy-2-oxo-2,5-dihydrofuran-3-yl)ethyl]-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxiran]-8a-yl]methyl acetate

> <JCHEM_LOGP>
2.682439173666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.52090603675868

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.822192433342314

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0083560797032103

> <JCHEM_POLAR_SURFACE_AREA>
94.59

> <JCHEM_REFRACTIVITY>
108.36279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,5S,6R,8S,8aR)-8-hydroxy-5-[2-(5-methoxy-2-oxo-5H-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

> <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       1.568  -4.217   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.630  -2.679   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.104  -2.884   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.481  -4.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.007  -4.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.738  -5.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.253  -5.594   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.366  -6.658   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.844  -6.225   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.458  -4.068   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.070  -3.401   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.794  -1.886   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.163  -1.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.342  -0.883   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.200  -0.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.704  -0.401   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.741   0.737   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.172  -1.869   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.341  -0.338   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.752   0.280   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.921   1.811   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.332   2.429   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.681   2.723   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.676  -2.197   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.005  -0.693   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.144  -1.730   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.144  -3.665   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.107  -4.803   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.603  -4.475   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.135  -3.007   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       2.098  -4.146   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   13   30                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24   30                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   25   26   27                                             
CONECT   25   24   26                                                       
CONECT   26   25   24                                                       
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   18    2   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₄O₇

Average Mass

422.5180 Da

Monoisotopic Mass

422.23045 Da

IUPAC Name

[(1R,4aR,5S,6R,8S,8aR)-8-hydroxy-5-[2-(5-methoxy-2-oxo-2,5-dihydrofuran-3-yl)ethyl]-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxiran]-8a-yl]methyl acetate

Traditional Name

(1R,4aR,5S,6R,8S,8aR)-8-hydroxy-5-[2-(5-methoxy-2-oxo-5H-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC[C@]3(CO3)[C@]1(COC(C)=O)[C@@H](O)C[C@@H](C)[C@]2(C)CCC1=CC(OC)OC1=O

InChI Identifier

InChI=1S/C23H34O7/c1-14-10-18(25)23(13-28-15(2)24)17(6-5-8-22(23)12-29-22)21(14,3)9-7-16-11-19(27-4)30-20(16)26/h11,14,17-19,25H,5-10,12-13H2,1-4H3/t14-,17-,18+,19?,21+,22+,23+/m1/s1

InChI Key

QWYIPUHTKBEREI-LDSWVEIGSA-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
campylantha		Not Available

Chemical Taxonomy

Classification

Not classified

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	2.68	ChemAxon
pKa (Strongest Acidic)	8.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	108.36 m³·mol⁻¹	ChemAxon
Polarizability	46.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

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 Q (NP0333082)

MOL for NP0333082 (ajucampylanoid Q)

3D MOL for NP0333082 (ajucampylanoid Q)

3D SDF for NP0333082 (ajucampylanoid Q)

3D-SDF for NP0333082 (ajucampylanoid Q)

PDB for NP0333082 (ajucampylanoid Q)

3D PDB for NP0333082 (ajucampylanoid Q)

SMILES for NP0333082 (ajucampylanoid Q)

INCHI for NP0333082 (ajucampylanoid Q)

Structure for NP0333082 (ajucampylanoid Q)

3D Structure for NP0333082 (ajucampylanoid Q)