NP-MRD: Showing NP-Card for Millefolacton B9 (NP0333150)

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Record Information

Version

2.0

Created at

2024-05-11 14:51:53 UTC

Updated at

2024-09-03 04:21:19 UTC

NP-MRD ID

NP0333150

Natural Product DOI

https://doi.org/10.57994/2450

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Millefolacton B9

Description

Millefolacton B9 belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Millefolacton B9 was first documented in 2023 (PMID: 36549383). Based on a literature review very few articles have been published on Millefolacton B9.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232317282D          

 29 32  0  0  1  0            999 V2000
    0.8971   -2.3908    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
    2.1890   -3.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0112   -2.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8364   -3.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -4.4256    0.0000 C   0  0  0  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
    1.6023   -0.8991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0096   -0.1816    0.0000 C   0  0  2  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
    3.0345    0.6736    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
    3.3613   -0.7598    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
    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
   -0.6115   -0.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -1.1886    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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  8  7  1  1  0  0  0
  9  8  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 21  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 18 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 26 29  1  0  0  0  0
  8 29  1  0  0  0  0
M  END


  Mrv2104 01232317282D          

 29 32  0  0  1  0            999 V2000
    0.8971   -2.3908    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
    2.1890   -3.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0112   -2.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8364   -3.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -4.4256    0.0000 C   0  0  0  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
    1.6023   -0.8991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0096   -0.1816    0.0000 C   0  0  2  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
    3.0345    0.6736    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
    3.3613   -0.7598    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
    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
   -0.6115   -0.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -1.1886    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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  8  7  1  1  0  0  0
  9  8  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 21  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 18 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 26 29  1  0  0  0  0
  8 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333150

> <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-KTOJYFSVSA-N

> <FORMULA>
C20H27ClO7

> <MOLECULAR_WEIGHT>
414.88

> <EXACT_MASS>
414.1445309

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.098459245917276

> <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 (2E)-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>
98.3585

> <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 (2E)-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  O   UNK     0       1.675  -4.463   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.209  -4.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.086  -5.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.621  -5.477   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.428  -6.995   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.305  -8.261   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.868  -2.944   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.991  -1.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.751  -0.339   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.178   1.090   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.361   2.077   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.664   1.257   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.288  -0.236   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.274  -1.418   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.094   1.830   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.703   1.534   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       2.793   2.622   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       0.437   0.657   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.788   1.590   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.983   0.063   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.279   3.044   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.155   4.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.261   3.009   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.473   4.534   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0       2.675   3.618   0.000  0.00  0.00          Cl+0
HETATM   26  C   UNK     0       0.333  -0.879   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.141  -0.436   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.427  -2.219   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.470  -1.919   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   10   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   26                                             
CONECT   19   18   20   21                                                  
CONECT   20   19   18                                                       
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24   25                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   18   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26    8                                                       
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 (2E)-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 (2E)-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-KTOJYFSVSA-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
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
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
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
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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
millefolium		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Fatty acyl
Oxane
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Halohydrin
Chlorohydrin
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
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	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	41.1 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

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

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Wikipedia Link

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METLIN ID

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PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

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Good Scents ID

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References

General References

Not Available

Showing NP-Card for Millefolacton B9 (NP0333150)

MOL for NP0333150 (Millefolacton B9)

3D MOL for NP0333150 (Millefolacton B9)

3D SDF for NP0333150 (Millefolacton B9)

3D-SDF for NP0333150 (Millefolacton B9)

PDB for NP0333150 (Millefolacton B9)

3D PDB for NP0333150 (Millefolacton B9)

SMILES for NP0333150 (Millefolacton B9)

INCHI for NP0333150 (Millefolacton B9)

Structure for NP0333150 (Millefolacton B9)

3D Structure for NP0333150 (Millefolacton B9)