NP-MRD: Showing NP-Card for Millefolacton B8 (NP0333149)

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Record Information

Version

1.0

Created at

2024-05-11 14:48:24 UTC

Updated at

2024-05-13 01:15:02 UTC

NP-MRD ID

NP0333149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Millefolacton B8

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232317242D          

 29 32  0  0  1  0            999 V2000
    3.3613   -0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8327   -0.1263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0096   -0.1816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7027    0.5842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3361    1.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126    0.8216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4961    1.4048    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    0.3520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4220    0.8519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5268    0.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    1.6306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6189    2.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6755    1.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7889    2.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    1.9381    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -0.4711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2287   -1.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6115   -0.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874   -1.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023   -0.8991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0719   -1.5773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7193   -2.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -2.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -3.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0142   -3.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890   -3.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345    0.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8003    0.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  8 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 11  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
  8 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
 20 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 22 27  2  0  0  0  0
  2 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END


  Mrv2104 01232317242D          

 29 32  0  0  1  0            999 V2000
    3.3613   -0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8327   -0.1263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0096   -0.1816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7027    0.5842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3361    1.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126    0.8216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4961    1.4048    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    0.3520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4220    0.8519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5268    0.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    1.6306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6189    2.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6755    1.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7889    2.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    1.9381    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -0.4711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2287   -1.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6115   -0.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874   -1.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023   -0.8991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0719   -1.5773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7193   -2.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -2.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -3.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0142   -3.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890   -3.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345    0.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8003    0.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  8 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 11  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
  8 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
 20 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 22 27  2  0  0  0  0
  2 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@H]3OC(=O)[C@@H](C)[C@@H]3[C@H](C[C@](C)(O)[C@@]11O[C@H]1[C@@H](O)[C@]2(C)Cl)OC(=O)C(\C)=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C20H27ClO7/c1-6-8(2)16(23)26-10-7-18(4,25)20-13(12-11(10)9(3)17(24)27-12)19(5,21)14(22)15(20)28-20/h6,9-15,22,25H,7H2,1-5H3/b8-6-/t9-,10-,11+,12-,13-,14+,15-,18-,19+,20+/m0/s1

> <INCHI_KEY>
MYCJGXXQLIFKON-GVHNVQKJSA-N

> <FORMULA>
C20H27ClO7

> <MOLECULAR_WEIGHT>
414.88

> <EXACT_MASS>
414.1445309

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.43797427789872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4S,5R,6S,9S,10R,11R,12R,13S)-11-chloro-2,12-dihydroxy-2,6,11-trimethyl-7-oxo-8,14-dioxatetracyclo[8.4.0.0^{1,13}.0^{5,9}]tetradecan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.6150983610000007

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.760726947053296

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.852760782389721

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3740693421506394

> <JCHEM_POLAR_SURFACE_AREA>
105.59

> <JCHEM_REFRACTIVITY>
98.35849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,5R,6S,9S,10R,11R,12R,13S)-11-chloro-2,12-dihydroxy-2,6,11-trimethyl-7-oxo-8,14-dioxatetracyclo[8.4.0.0^{1,13}.0^{5,9}]tetradecan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-23         0                                  
HETATM    1  C   UNK     0       6.274  -1.418   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.288  -0.236   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.751  -0.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.178   1.090   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.361   2.077   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.703   1.534   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       2.793   2.622   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0       0.437   0.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.788   1.590   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.983   0.063   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.279   3.044   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.155   4.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.261   3.009   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.473   4.534   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       2.675   3.618   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       0.333  -0.879   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.427  -2.219   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.141  -0.436   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.470  -1.919   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.991  -1.678   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.868  -2.944   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.209  -4.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.675  -4.463   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.798  -3.197   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.016  -5.855   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.893  -7.121   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.086  -5.603   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.664   1.257   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.094   1.830   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   28                                                       
CONECT    6    4    7    8   13                                             
CONECT    7    6                                                            
CONECT    8    6    9   10   16                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    8                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    8   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   22                                                            
CONECT   28    2    5   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₇ClO₇

Average Mass

414.8800 Da

Monoisotopic Mass

414.14453 Da

IUPAC Name

(1R,2S,4S,5R,6S,9S,10R,11R,12R,13S)-11-chloro-2,12-dihydroxy-2,6,11-trimethyl-7-oxo-8,14-dioxatetracyclo[8.4.0.0^{1,13}.0^{5,9}]tetradecan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1R,2S,4S,5R,6S,9S,10R,11R,12R,13S)-11-chloro-2,12-dihydroxy-2,6,11-trimethyl-7-oxo-8,14-dioxatetracyclo[8.4.0.0^{1,13}.0^{5,9}]tetradecan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@H]3OC(=O)[C@@H](C)[C@@H]3[C@H](C[C@](C)(O)[C@@]11O[C@H]1[C@@H](O)[C@]2(C)Cl)OC(=O)C(\C)=C/C

InChI Identifier

InChI=1S/C20H27ClO7/c1-6-8(2)16(23)26-10-7-18(4,25)20-13(12-11(10)9(3)17(24)27-12)19(5,21)14(22)15(20)28-20/h6,9-15,22,25H,7H2,1-5H3/b8-6-/t9-,10-,11+,12-,13-,14+,15-,18-,19+,20+/m0/s1

InChI Key

MYCJGXXQLIFKON-GVHNVQKJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lijun702@ms.xjb.ac.cn	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lijun702@ms.xjb.ac.cn	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lijun702@ms.xjb.ac.cn	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lijun702@ms.xjb.ac.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	lijun702@ms.xjb.ac.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	lijun702@ms.xjb.ac.cn	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
millefolium		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	1.62	ChemAxon
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.36 m³·mol⁻¹	ChemAxon
Polarizability	41.44 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	No	ChemAxon

External Links

Not Available

References

General References

Li H, Liu L, Liu G, Li J, Aisa HA: Chlorine-containing guaianolide sesquiterpenoids from Achillea millefolium L. with inhibitory effects against LPS-induced NO release in BV-2 microglial cells. Phytochemistry. 2023 Mar;207:113567. doi: 10.1016/j.phytochem.2022.113567. Epub 2022 Dec 19. [PubMed:36549383 ]

Showing NP-Card for Millefolacton B8 (NP0333149)

MOL for NP0333149 (Millefolacton B8)

3D MOL for NP0333149 (Millefolacton B8)

3D SDF for NP0333149 (Millefolacton B8)

3D-SDF for NP0333149 (Millefolacton B8)

PDB for NP0333149 (Millefolacton B8)

3D PDB for NP0333149 (Millefolacton B8)

SMILES for NP0333149 (Millefolacton B8)

INCHI for NP0333149 (Millefolacton B8)

Structure for NP0333149 (Millefolacton B8)

3D Structure for NP0333149 (Millefolacton B8)