NP-MRD: Showing NP-Card for ajucampylanoid H (NP0333073)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2024-05-08 21:10:37 UTC

Updated at

2024-05-10 00:17:08 UTC

NP-MRD ID

NP0333073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajucampylanoid H

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01202323472D          

 24 27  0  0  1  0            999 V2000
    0.9254   -1.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9802   -1.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032   -1.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2645   -2.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0890   -2.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -3.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325   -3.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9824   -3.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0978   -1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0732   -0.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3019   -1.6506    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  2  0  0  0  0
  5  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 13  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 15  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
 23 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23  2  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC[C@H]3C(=O)O[C@@H](C[C@@H](C)[C@]1(C)CCC1=COC=C1)[C@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-13-11-17-20(3)15(18(21)23-17)5-4-6-16(20)19(13,2)9-7-14-8-10-22-12-14/h8,10,12-13,15-17H,4-7,9,11H2,1-3H3/t13-,15+,16-,17+,19+,20+/m1/s1

> <INCHI_KEY>
XXQAFIMDGMHQGO-MCYDHMDPSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.17251425505614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,8R,9S,10R,12R)-9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one

> <JCHEM_LOGP>
4.660585436666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7841265592620212

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
88.224

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,8R,9S,10R,12R)-9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

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  C   UNK     0       1.727  -3.238   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.696  -3.445   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.233  -3.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.094  -4.614   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.633  -4.668   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.057  -6.149   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.781  -7.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.567  -6.062   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.182  -1.890   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.633   2.359   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.078   3.605   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.737  -0.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       4.297  -3.081   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   10   23                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15                                                            
CONECT   17   13   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   15   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17    2   24                                             
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(1S,4R,8R,9S,10R,12R)-9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one

Traditional Name

(1S,4R,8R,9S,10R,12R)-9-[2-(furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC[C@H]3C(=O)O[C@@H](C[C@@H](C)[C@]1(C)CCC1=COC=C1)[C@]23C

InChI Identifier

InChI=1S/C20H28O3/c1-13-11-17-20(3)15(18(21)23-17)5-4-6-16(20)19(13,2)9-7-14-8-10-22-12-14/h8,10,12-13,15-17H,4-7,9,11H2,1-3H3/t13-,15+,16-,17+,19+,20+/m1/s1

InChI Key

XXQAFIMDGMHQGO-MCYDHMDPSA-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, 400 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

Not Available

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	4.66	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.22 m³·mol⁻¹	ChemAxon
Polarizability	36.17 Å³	ChemAxon
Number of Rings	4	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

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 H (NP0333073)

MOL for NP0333073 (ajucampylanoid H)

3D MOL for NP0333073 (ajucampylanoid H)

3D SDF for NP0333073 (ajucampylanoid H)

3D-SDF for NP0333073 (ajucampylanoid H)

PDB for NP0333073 (ajucampylanoid H)

3D PDB for NP0333073 (ajucampylanoid H)

SMILES for NP0333073 (ajucampylanoid H)

INCHI for NP0333073 (ajucampylanoid H)

Structure for NP0333073 (ajucampylanoid H)

3D Structure for NP0333073 (ajucampylanoid H)