NP-MRD: Showing NP-Card for Lactapiperanol C (NP0047686)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:44:16 UTC

Updated at

2022-03-17 20:44:16 UTC

NP-MRD ID

NP0047686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lactapiperanol C

Description

Lactapiperanol C belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Lactapiperanol C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, lactapiperanol C has been detected, but not quantified in, mushrooms. Lactapiperanol C is found in Lactarius piperatus and Russula foetens. This could make lactapiperanol C a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241209402D          

 20 23  0  0  0  0            999 V2000
   -1.0684    0.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585   -0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    0.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429   -0.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6258    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542   -0.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3413   -0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -1.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -0.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088   -1.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684    1.5405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 18  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1OCC2(O)C(O)C3CC(C)(C)CC3C3(C)CC123

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O4/c1-13(2)5-9-10(6-13)14(3)7-15(14)12(19-4)20-8-16(15,18)11(9)17/h9-12,17-18H,5-8H2,1-4H3

> <INCHI_KEY>
DEBINYRQIQKNDF-UHFFFAOYSA-N

> <FORMULA>
C16H26O4

> <MOLECULAR_WEIGHT>
282.3752

> <EXACT_MASS>
282.18310932

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.296540640265164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-methoxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.0¹,³.0⁴,⁸]tridecane-9,10-diol

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
1.2409377616666661

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.492376117625373

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.519346214129946

> <JCHEM_PKA_STRONGEST_BASIC>
-3.373352378797758

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
73.19749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-methoxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.0¹,³.0⁴,⁸]tridecane-9,10-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.994   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.994  -0.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.661  -0.977   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.669  -0.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.669   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.661   2.102   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.133  -0.682   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.035   0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.133   1.804   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.461   1.804   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.370   0.564   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.461  -0.682   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.124   1.653   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.370  -0.207   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.661   3.644   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.661  -2.518   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.994  -1.748   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.936  -2.154   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.994   2.876   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.538  -3.644   0.000  0.00  0.00           C+0
CONECT    1    2    6   10   19                                             
CONECT    2    1    3   12   17                                             
CONECT    3    2    4   16   17                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5   15                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9   13   14                                             
CONECT    9    5    8                                                       
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12    2   11   18                                                  
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    6                                                            
CONECT   16    3                                                            
CONECT   17    2    3                                                       
CONECT   18   12   20                                                       
CONECT   19    1                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₆O₄

Average Mass

282.3752 Da

Monoisotopic Mass

282.18311 Da

IUPAC Name

13-methoxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.0¹,³.0⁴,⁸]tridecane-9,10-diol

Traditional Name

13-methoxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.0¹,³.0⁴,⁸]tridecane-9,10-diol

CAS Registry Number

243447-93-0

SMILES

COC1OCC2(O)C(O)C3CC(C)(C)CC3C3(C)CC123

InChI Identifier

InChI=1S/C16H26O4/c1-13(2)5-9-10(6-13)14(3)7-15(14)12(19-4)20-8-16(15,18)11(9)17/h9-12,17-18H,5-8H2,1-4H3

InChI Key

DEBINYRQIQKNDF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Lactarius piperatus	LOTUS Database	35616633
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Russula foetens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Not Available

Substituents

Not Available

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	1.19	ALOGPS
logP	1.24	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.2 m³·mol⁻¹	ChemAxon
Polarizability	31.3 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

HMDB0033630

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011724

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

85158920

PDB ID

Not Available

ChEBI ID

138779

Good Scents ID

Not Available

References

General References

Showing NP-Card for Lactapiperanol C (NP0047686)

MOL for NP0047686 (Lactapiperanol C)

3D MOL for NP0047686 (Lactapiperanol C)

3D SDF for NP0047686 (Lactapiperanol C)

3D-SDF for NP0047686 (Lactapiperanol C)

PDB for NP0047686 (Lactapiperanol C)

3D PDB for NP0047686 (Lactapiperanol C)

SMILES for NP0047686 (Lactapiperanol C)

INCHI for NP0047686 (Lactapiperanol C)

Structure for NP0047686 (Lactapiperanol C)

3D Structure for NP0047686 (Lactapiperanol C)