NP-MRD: Showing NP-Card for Lycopersiconolide (NP0047699)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:29 UTC

Updated at

2022-03-17 20:44:30 UTC

NP-MRD ID

NP0047699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lycopersiconolide

Description

Lycopersiconolide belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Lycopersiconolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, lycopersiconolide has been detected, but not quantified in, garden tomato. This could make lycopersiconolide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307172D          

 26 30  0  0  0  0            999 V2000
    6.5077    0.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9706    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6816   -1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8616   -1.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1476    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877    0.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276    0.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8677    0.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9902   -1.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -1.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1703   -0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4789   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5303   -0.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190   -0.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7103   -0.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820   -0.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5581    0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297   -0.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8390   -0.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    0.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459    0.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2989   -0.4367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873    1.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -0.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 11  1  0  0  0  0
 18 17  1  0  0  0  0
 20  1  1  0  0  0  0
 20  8  1  0  0  0  0
 20 12  1  0  0  0  0
 20 15  1  0  0  0  0
 21  2  1  0  0  0  0
 21  9  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22  3  1  0  0  0  0
 22 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 13  1  0  0  0  0
 24 19  2  0  0  0  0
 25 22  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  1  0  0  0  0
M  END


  Mrv0541 05061307172D          

 26 30  0  0  0  0            999 V2000
    6.5077    0.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9706    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6816   -1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8616   -1.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1476    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877    0.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276    0.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8677    0.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9902   -1.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -1.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1703   -0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4789   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5303   -0.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190   -0.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7103   -0.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820   -0.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5581    0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297   -0.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8390   -0.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    0.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459    0.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2989   -0.4367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873    1.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -0.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 11  1  0  0  0  0
 18 17  1  0  0  0  0
 20  1  1  0  0  0  0
 20  8  1  0  0  0  0
 20 12  1  0  0  0  0
 20 15  1  0  0  0  0
 21  2  1  0  0  0  0
 21  9  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22  3  1  0  0  0  0
 22 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 13  1  0  0  0  0
 24 19  2  0  0  0  0
 25 22  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-20-8-6-13(23)10-12(20)4-5-14-15(20)7-9-21(2)16(14)11-17-18(21)22(3,25)19(24)26-17/h12-18,23,25H,4-11H2,1-3H3

> <INCHI_KEY>
OCPGSVYCKLXPSO-UHFFFAOYSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.503

> <EXACT_MASS>
362.245709576

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
41.257469704659016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-one

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.804876914333335

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2963963211217

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.273486322040938

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569558947805795

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
98.13769999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.148   1.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.412   1.541   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.174   1.865   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.472  -2.957   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.942  -2.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.209   0.765   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.617   1.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.678   0.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.086   1.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.915  -1.886   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.642  -2.232   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.385  -1.717   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.827  -0.645   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.323  -1.377   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.235  -0.137   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.793  -1.208   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.313  -1.454   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.642   0.050   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.162  -0.196   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.766  -0.306   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.174   0.203   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.312   0.828   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      17.358  -0.815   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.658   0.132   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.950   2.233   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.781  -1.607   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    5   12                                                       
CONECT    5    4   14                                                       
CONECT    6    8   13                                                       
CONECT    7    9   15                                                       
CONECT    8    6   20                                                       
CONECT    9    7   21                                                       
CONECT   10   12   13                                                       
CONECT   11   16   17                                                       
CONECT   12    4   10   20                                                  
CONECT   13    6   10   23                                                  
CONECT   14    5   15   16                                                  
CONECT   15    7   14   20                                                  
CONECT   16   11   14   21                                                  
CONECT   17   11   18   26                                                  
CONECT   18   17   21   22                                                  
CONECT   19   22   24   26                                                  
CONECT   20    1    8   12   15                                             
CONECT   21    2    9   16   18                                             
CONECT   22    3   18   19   25                                             
CONECT   23   13                                                            
CONECT   24   19                                                            
CONECT   25   22                                                            
CONECT   26   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
3b,16b,20S-Trihydroxy-5a-pregnane-20-carboxylic acid 22,16-lactone	HMDB
3b,20S-Dihydroxy-5a-pregnane-20,16b-carbolactone	HMDB

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5030 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

7,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-one

Traditional Name

7,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-one

CAS Registry Number

110612-29-8

SMILES

CC1(O)C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC1=O

InChI Identifier

InChI=1S/C22H34O4/c1-20-8-6-13(23)10-12(20)4-5-14-15(20)7-9-21(2)16(14)11-17-18(21)22(3,25)19(24)26-17/h12-18,23,25H,4-11H2,1-3H3

InChI Key

OCPGSVYCKLXPSO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
20-hydroxysteroid
3-hydroxysteroid
Hydroxysteroid
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	3.17	ALOGPS
logP	2.8	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.27	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	98.14 m³·mol⁻¹	ChemAxon
Polarizability	41.26 Å³	ChemAxon
Number of Rings	5	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

HMDB0033677

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011780

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

14186883

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Lycopersiconolide (NP0047699)

MOL for NP0047699 (Lycopersiconolide)

3D MOL for NP0047699 (Lycopersiconolide)

3D SDF for NP0047699 (Lycopersiconolide)

3D-SDF for NP0047699 (Lycopersiconolide)

PDB for NP0047699 (Lycopersiconolide)

3D PDB for NP0047699 (Lycopersiconolide)

SMILES for NP0047699 (Lycopersiconolide)

INCHI for NP0047699 (Lycopersiconolide)

Structure for NP0047699 (Lycopersiconolide)

3D Structure for NP0047699 (Lycopersiconolide)