NP-MRD: Showing NP-Card for 1-hydroarmillaricin (NP0332589)

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Record Information

Version

2.0

Created at

2024-02-29 00:01:58 UTC

Updated at

2024-09-03 04:19:42 UTC

NP-MRD ID

NP0332589

Natural Product DOI

https://doi.org/10.57994/1849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-hydroarmillaricin

Description

1-Hydroarmillaricin belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof. Based on a literature review very few articles have been published on 1-hydroarmillaricin.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02292400022D          

 31 34  0  0  1  0            999 V2000
   -0.4133   -1.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874   -1.6963    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -0.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    0.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.4336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4079    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    1.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.6627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2455   -1.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    0.0359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897   -1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -1.1322    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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 21  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
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 21 27  1  0  0  0  0
 22 28  1  1  0  0  0
 22 29  1  0  0  0  0
 29 16  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 15 31  1  0  0  0  0
M  END


  Mrv2104 02292400022D          

 31 34  0  0  1  0            999 V2000
   -0.4133   -1.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874   -1.6963    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -0.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    0.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.4336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4079    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    1.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.6627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2455   -1.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    0.0359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897   -1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -1.1322    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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 21  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
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 21 27  1  0  0  0  0
 22 28  1  1  0  0  0
 22 29  1  0  0  0  0
 29 16  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 15 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC(C)(C)CC1=CC(CO)=C1[C@@H](C[C@]21C)OC(=O)C1=C(C)C(Cl)=C(OC)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO5/c1-12-19(16(27)7-17(29-5)21(12)25)22(28)30-18-10-24(4)15-9-23(2,3)8-13(15)6-14(11-26)20(18)24/h6-7,15,18,26-27H,8-11H2,1-5H3/t15-,18+,24+/m0/s1

> <INCHI_KEY>
KMYUFDYJMJSFKN-PQNFPLSNSA-N

> <FORMULA>
C24H29ClO5

> <MOLECULAR_WEIGHT>
432.94

> <EXACT_MASS>
432.1703517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
47.01946936418876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_LOGP>
4.941867983666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.106138380260045

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.324082151841216

> <JCHEM_PKA_STRONGEST_BASIC>
-2.752375388606139

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
117.68009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-FEB-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-FEB-24         0                                  
HETATM    1  O   UNK     0      -0.771  -3.067   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.225  -1.595   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.726  -1.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.774  -2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.321  -3.852   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.275  -2.038   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -6.323  -3.166   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -5.729  -0.566   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.230  -0.223   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.684   1.249   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.681   0.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.180   0.220   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.132   1.348   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.177  -0.466   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.324  -0.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.628   0.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.348   1.371   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.529   2.675   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.249   4.037   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.887   1.428   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.706   0.124   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.986  -1.237   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.058  -2.342   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.441  -1.664   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.971  -3.110   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.934  -1.288   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.223  -0.140   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       4.167   0.067   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       3.447  -1.294   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.901  -2.766   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.143  -2.113   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11    3   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17   29                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   28   29                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   21                                                       
CONECT   28   22                                                            
CONECT   29   22   16   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   15                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₉ClO₅

Average Mass

432.9400 Da

Monoisotopic Mass

432.17035 Da

IUPAC Name

(2R,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Traditional Name

(2R,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

CAS Registry Number

Not Available

SMILES

[H][C@]12CC(C)(C)CC1=CC(CO)=C1[C@@H](C[C@]21C)OC(=O)C1=C(C)C(Cl)=C(OC)C=C1O

InChI Identifier

InChI=1S/C24H29ClO5/c1-12-19(16(27)7-17(29-5)21(12)25)22(28)30-18-10-24(4)15-9-23(2,3)8-13(15)6-14(11-26)20(18)24/h6-7,15,18,26-27H,8-11H2,1-5H3/t15-,18+,24+/m0/s1

InChI Key

KMYUFDYJMJSFKN-PQNFPLSNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Illudanes and illudins

Alternative Parents

Substituents

Illudane sesquiterpenoid
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Halobenzoic acid or derivatives
3-halobenzoic acid or derivatives
Salicylic acid or derivatives
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
4-chlorophenol
M-cresol
4-halophenol
Benzoyl
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Halobenzene
Fatty acid ester
Chlorobenzene
Alkyl aryl ether
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.94	ChemAxon
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-2.8	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	117.68 m³·mol⁻¹	ChemAxon
Polarizability	47.02 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

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

Not Available

Showing NP-Card for 1-hydroarmillaricin (NP0332589)

MOL for NP0332589 (1-hydroarmillaricin)

3D MOL for NP0332589 (1-hydroarmillaricin)

3D SDF for NP0332589 (1-hydroarmillaricin)

3D-SDF for NP0332589 (1-hydroarmillaricin)

PDB for NP0332589 (1-hydroarmillaricin)

3D PDB for NP0332589 (1-hydroarmillaricin)

SMILES for NP0332589 (1-hydroarmillaricin)

INCHI for NP0332589 (1-hydroarmillaricin)

Structure for NP0332589 (1-hydroarmillaricin)

3D Structure for NP0332589 (1-hydroarmillaricin)