NP-MRD: Showing NP-Card for versiol (NP0321457)

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Record Information

Version

2.0

Created at

2022-09-11 23:40:22 UTC

Updated at

2022-09-11 23:40:22 UTC

NP-MRD ID

NP0321457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

versiol

Description

Versiol belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. versiol is found in Aspergillus silvaticus, Penicillium decumbens and Penicillium striatisporum. versiol was first documented in 2005 (PMID: 15844954). Based on a literature review a small amount of articles have been published on Versiol (PMID: 25835225) (PMID: 28654255) (PMID: 31817515) (PMID: 30598828).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -3.8055    0.8679   -0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1162    0.5377    0.5116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9685    1.4318    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062    1.1062    0.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4332    1.9457    0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6871    1.4857    0.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9725    0.0408    0.6168 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2112   -0.6740    1.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    0.0199    0.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551    0.5070   -1.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1215    0.7778   -1.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1469   -0.2716   -1.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564   -0.8647   -2.5671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9036   -0.5890   -0.2149 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0926   -2.1064   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4873   -0.2460    0.0349 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2820   -1.1274    0.9575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2747   -0.5987    2.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7387   -0.9255    0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3520    0.3730   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8618    0.5263   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8557    1.9769   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    0.6906    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620    2.4214    1.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    3.0078    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833    2.1518    1.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5630    0.0956    2.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -1.4101    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3760   -1.2117    2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518    1.4656   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029   -0.1828   -1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483    1.8057   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    0.7555   -3.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861   -2.4003   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583   -2.5214    0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3347   -2.5628   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0414   -0.2572   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497   -2.1823    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0580   -0.9354    2.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3536   -1.5098    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9326   -1.4136   -0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 19  1  0
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
  4  3  2  0
  3  2  1  0
 14 16  1  0
 14  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
 19 40  1  0
 19 41  1  0
 17 38  1  1
 18 39  1  0
 16 37  1  6
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
  3 24  1  0
M  END


  Mrv1652309122201402D          

 19 21  0  0  1  0            999 V2000
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16  4  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H](O)[C@H]2C(C=C[C@]3(C)OCCC(=O)[C@]23C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O3/c1-10-8-11-4-6-15(2)16(3,13(18)5-7-19-15)14(11)12(17)9-10/h4,6,8,10,12,14,17H,5,7,9H2,1-3H3/t10-,12+,14-,15+,16-/m1/s1

> <INCHI_KEY>
SXHZNZFKZCCMFJ-ZZIHQOKHSA-N

> <FORMULA>
C16H22O3

> <MOLECULAR_WEIGHT>
262.349

> <EXACT_MASS>
262.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.83997744596801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,8S,10S,10aS,10bR)-10-hydroxy-4a,8,10b-trimethyl-1H,2H,3H,4aH,8H,9H,10H,10aH,10bH-naphtho[2,1-b]pyran-1-one

> <JCHEM_LOGP>
1.7731404333333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.31195566241993

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.816801447828265

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8782618117318073

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
75.39390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,8S,10S,10aS,10bR)-10-hydroxy-4a,8,10b-trimethyl-2H,3H,8H,9H,10H,10aH-naphtho[2,1-b]pyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.955   1.127   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.725  -0.206   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.415  -4.207   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   14                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15   16                                             
CONECT   15   14                                                            
CONECT   16   14    4   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂O₃

Average Mass

262.3490 Da

Monoisotopic Mass

262.15689 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H](O)[C@H]2C(C=C[C@]3(C)OCCC(=O)[C@]23C)=C1

InChI Identifier

InChI=1S/C16H22O3/c1-10-8-11-4-6-15(2)16(3,13(18)5-7-19-15)14(11)12(17)9-10/h4,6,8,10,12,14,17H,5,7,9H2,1-3H3/t10-,12+,14-,15+,16-/m1/s1

InChI Key

SXHZNZFKZCCMFJ-ZZIHQOKHSA-N

Experimental Spectra

Not Available

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
Aspergillus silvaticus	LOTUS Database	35616633
Penicillium decumbens	LOTUS Database	35616633
Penicillium striatisporum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthalene
Oxane
Pyran
Ketone
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043103

Chemspider ID

23076317

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101042985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stewart M, Capon RJ, Lacey E, Tennant S, Gill JH: Calbistrin E and two other new metabolites from an Australian isolate of Penicillium striatisporum. J Nat Prod. 2005 Apr;68(4):581-4. doi: 10.1021/np049614y. [PubMed:15844954 ]
Fu Y, Wu P, Xue J, Wei X, Li H: Versicorin, a new lovastatin analogue from the fungus Aspergillus versicolor SC0156. Nat Prod Res. 2015;29(14):1363-8. doi: 10.1080/14786419.2015.1026342. Epub 2015 Apr 2. [PubMed:25835225 ]
Cho N, Ransom TT, Sigmund J, Tran T, Cichewicz RH, Goetz M, Beutler JA: Growth Inhibition of Colon Cancer and Melanoma Cells by Versiol Derivatives from a Paraconiothyrium Species. J Nat Prod. 2017 Jul 28;80(7):2037-2044. doi: 10.1021/acs.jnatprod.7b00170. Epub 2017 Jun 27. [PubMed:28654255 ]
Niu S, Xia M, Chen M, Liu X, Li Z, Xie Y, Shao Z, Zhang G: Cytotoxic Polyketides Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum MCCC 3A00292. Mar Drugs. 2019 Dec 5;17(12). pii: md17120686. doi: 10.3390/md17120686. [PubMed:31817515 ]
Grijseels S, Pohl C, Nielsen JC, Wasil Z, Nygard Y, Nielsen J, Frisvad JC, Nielsen KF, Workman M, Larsen TO, Driessen AJM, Frandsen RJN: Identification of the decumbenone biosynthetic gene cluster in Penicillium decumbens and the importance for production of calbistrin. Fungal Biol Biotechnol. 2018 Dec 19;5:18. doi: 10.1186/s40694-018-0063-4. eCollection 2018. [PubMed:30598828 ]
LOTUS database [Link]

Showing NP-Card for versiol (NP0321457)

MOL for NP0321457 (versiol)

3D MOL for NP0321457 (versiol)

3D SDF for NP0321457 (versiol)

3D-SDF for NP0321457 (versiol)

PDB for NP0321457 (versiol)

3D PDB for NP0321457 (versiol)

SMILES for NP0321457 (versiol)

INCHI for NP0321457 (versiol)

Structure for NP0321457 (versiol)

3D Structure for NP0321457 (versiol)