NP-MRD: Showing NP-Card for sorbicillin (NP0308943)

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Record Information

Version

1.0

Created at

2022-09-11 03:08:09 UTC

Updated at

2024-05-02 08:06:25 UTC

NP-MRD ID

NP0308943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sorbicillin

Description

Sorbicillin belongs to the class of organic compounds known as xylenols. These are aromatic compounds that contain a xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups, and at least one hydroxyl group. sorbicillin is found in Huperzia serrata, Penicillium terrestre, Streptomyces olivaceus and Trichoderma longibrachiatum. Based on a literature review very few articles have been published on Sorbicillin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    6.5125    0.4316   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2683   -0.1934    0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654    0.1826   -0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9122   -0.4975    0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -0.1268    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5051   -0.7896    0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6420   -1.7280    1.5591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -0.3812    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0904    0.6384   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3754    1.0265   -0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    2.1247   -1.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216    0.3414   -0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7106    0.6792   -0.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2116   -0.6873    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3659   -1.4003    1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286   -1.0296    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6938   -2.0466    1.7951 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803    1.2303   -0.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1748   -0.3143   -0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0162    0.9327    0.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052   -1.0073    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9781    0.9935   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266   -1.3047    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6307    0.6860   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2589    1.1757   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7269    2.6581   -2.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1410    1.6671   -2.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3973    2.7920   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9064    1.4238   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3033   -1.4217    2.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3047   -2.4795    0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3187   -1.0271    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -2.5485    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
M  END


  Mrv1652309112205082D          

 17 17  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308943

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C=C\C(=O)C1=CC(C)=C(O)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O3/c1-4-5-6-7-12(15)11-8-9(2)13(16)10(3)14(11)17/h4-8,16-17H,1-3H3/b5-4+,7-6+

> <INCHI_KEY>
RKKPUBAAIGFXOG-YTXTXJHMSA-N

> <FORMULA>
C14H16O3

> <MOLECULAR_WEIGHT>
232.279

> <EXACT_MASS>
232.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.81077840643657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-1-(2,4-dihydroxy-3,5-dimethylphenyl)hexa-2,4-dien-1-one

> <JCHEM_LOGP>
4.270749145

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.356151125772088

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.953769449357875

> <JCHEM_PKA_STRONGEST_BASIC>
-6.597200040229393

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
71.14480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-1-(2,4-dihydroxy-3,5-dimethylphenyl)hexa-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
(2E,4E)-1-(2,4-Dihydroxy-3,5-dimethylphenyl)-2,4-hexadien-1-one	MeSH
3-Hydroxy-2,4-dimethyl-6-(1-oxo-hexa-2,4-dienyl)phenol	MeSH

Chemical Formula

C₁₄H₁₆O₃

Average Mass

232.2790 Da

Monoisotopic Mass

232.10994 Da

IUPAC Name

(2E,4E)-1-(2,4-dihydroxy-3,5-dimethylphenyl)hexa-2,4-dien-1-one

Traditional Name

(2E,4E)-1-(2,4-dihydroxy-3,5-dimethylphenyl)hexa-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

C\C=C\C=C\C(=O)C1=CC(C)=C(O)C(C)=C1O

InChI Identifier

InChI=1S/C14H16O3/c1-4-5-6-7-12(15)11-8-9(2)13(16)10(3)14(11)17/h4-8,16-17H,1-3H3/b5-4+,7-6+

InChI Key

RKKPUBAAIGFXOG-YTXTXJHMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	545103346@qq.com	Nanjing University of Chinese Medicine	Ying Zhang	2024-05-02	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
citrinum ZY-2		Not Available
Huperzia serrata	LOTUS Database	35616633
Penicillium terrestre	LOTUS Database	35616633
Streptomyces olivaceus	LOTUS Database	35616633
Trichoderma longibrachiatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xylenols. These are aromatic compounds that contain a xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups, and at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

Xylenols

Alternative Parents

Substituents

Xylenol
Benzoyl
M-xylene
Aryl ketone
Resorcinol
P-cresol
O-cresol
Phenol
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.27	ChemAxon
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.14 m³·mol⁻¹	ChemAxon
Polarizability	25.81 Å³	ChemAxon
Number of Rings	1	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

4525514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5376187

PDB ID

Not Available

ChEBI ID

167836

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Zhang Y, Zhang J, Du Q, Wu XM, Chen Y, Tan RX: Citrisorbicillinol, an undescribed hybrid sorbicillinoid with osteogenic activity from Penicillium citrinum ZY-2. Fitoterapia. 2024 Mar;173:105836. doi: 10.1016/j.fitote.2024.105836. Epub 2024 Jan 28. [PubMed:38286315 ]

Showing NP-Card for sorbicillin (NP0308943)

MOL for NP0308943 (sorbicillin)

3D MOL for NP0308943 (sorbicillin)

3D SDF for NP0308943 (sorbicillin)

3D-SDF for NP0308943 (sorbicillin)

PDB for NP0308943 (sorbicillin)

3D PDB for NP0308943 (sorbicillin)

SMILES for NP0308943 (sorbicillin)

INCHI for NP0308943 (sorbicillin)

Structure for NP0308943 (sorbicillin)

3D Structure for NP0308943 (sorbicillin)