NP-MRD: Showing NP-Card for Porellapinguisanolide (NP0064381)

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Record Information

Version

2.0

Created at

2022-04-28 08:37:28 UTC

Updated at

2022-04-28 08:37:28 UTC

NP-MRD ID

NP0064381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Porellapinguisanolide

Description

Porellapinguisanolide belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Porellapinguisanolide is found in Porella cordaeana, Porella platyphylla and Trocholejeunea sandvicensis. Based on a literature review very few articles have been published on Porellapinguisanolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    1.4261   -2.1336   -1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -0.7947   -0.8369 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8573    0.2327   -0.3682 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2601   -0.2773   -0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1196    0.8281    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155    1.6703   -0.5345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447    0.7918    0.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999    1.5347    0.5207 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6476    2.1068   -0.7178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625    1.4556   -1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5246    1.7668   -2.1553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7253    0.5357    0.5656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1672    0.5302    2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692    1.0022   -0.3131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6345    2.1465    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872   -0.2707   -0.4131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6120   -0.1593   -1.4183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5776   -1.2736   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671   -0.8316    0.0735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2303   -1.8122    1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5338   -2.1994   -1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693   -2.9586   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802   -2.4987   -2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -0.4086   -1.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3079   -1.0797    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6938   -0.5551   -1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118    0.9100    1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2092    2.3482    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3355    0.1359    2.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2362    1.6202    2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1482    0.1064    2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5278    1.2709   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9001    2.9538    0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3081    2.5353   -0.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1372    1.9059    1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1560   -0.5280    0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630   -1.0220   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8756   -2.3102   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3794   -1.1163   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898   -1.6075    1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087   -2.8765    0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6747   -1.6744    1.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  1
 19  2  1  0
  2  1  1  0
  2  3  1  0
  3  4  1  1
  4  5  1  0
  5  6  2  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  1
 12 14  1  0
 12 19  1  0
 10  3  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 14 32  1  6
 16 36  1  1
 17 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
  2 24  1  6
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  1
 13 29  1  0
 13 30  1  0
 13 31  1  0
M  END


  Mrv1652304282210372D          

 20 22  0  0  1  0            999 V2000
    2.2614    0.5726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3584    1.3919    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1676    1.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706    0.8329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0105    0.2271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1714   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3899    0.7358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    1.9786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9581    1.8909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5152    1.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041    1.2920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832    0.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    0.1377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0401    0.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232    2.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129    3.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4780    4.0202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554    2.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6002    2.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3121   -0.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  1  0  0  0
  4  7  1  6  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  1  0  0  0
  9 14  1  0  0  0  0
  9 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 18  1  1  0  0  0
  2 19  1  1  0  0  0
  1 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H](O)C[C@@]2(C)[C@H](C)[C@]3(CC=O)O[C@@H](OC3=O)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-8-10(17)7-13(3)9(2)15(5-6-16)11(18)19-12(20-15)14(8,13)4/h6,8-10,12,17H,5,7H2,1-4H3/t8-,9+,10+,12-,13+,14-,15+/m1/s1

> <INCHI_KEY>
YZAVUVDOBXZQNS-JLPLLFGXSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.63790377335107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,2S,3S,4S,6S,7S,8S)-4-hydroxy-2,3,6,7-tetramethyl-9-oxo-10,11-dioxatricyclo[6.2.1.0^{2,6}]undecan-8-yl]acetaldehyde

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.2515498500000004

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.914021185946808

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.9621418914859

> <JCHEM_PKA_STRONGEST_BASIC>
-2.836674898044903

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
69.6503

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,2S,3S,4S,6S,7S,8S)-4-hydroxy-2,3,6,7-tetramethyl-9-oxo-10,11-dioxatricyclo[6.2.1.0^{2,6}]undecan-8-yl]acetaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.221   1.069   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.402   2.598   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.913   2.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.665   1.555   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.620   0.424   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.920  -1.086   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.194   1.374   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.320   3.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.788   3.530   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.962   2.231   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.568   2.412   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.462   0.774   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.913   0.257   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.941   1.753   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.977   4.838   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.704   6.196   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.892   7.504   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.837   5.144   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.854   4.071   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.316  -0.468   0.000  0.00  0.00           C+0
CONECT    1    2    5   13   20                                             
CONECT    2    1    3    8   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4                                                            
CONECT    8    2    9   18                                                  
CONECT    9    8   10   14   15                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    1   14                                                  
CONECT   14   13    9                                                       
CONECT   15    9   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    8                                                            
CONECT   19    2                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

2-[(1S,2S,3S,4S,6S,7S,8S)-4-hydroxy-2,3,6,7-tetramethyl-9-oxo-10,11-dioxatricyclo[6.2.1.0^{2,6}]undecan-8-yl]acetaldehyde

Traditional Name

2-[(1S,2S,3S,4S,6S,7S,8S)-4-hydroxy-2,3,6,7-tetramethyl-9-oxo-10,11-dioxatricyclo[6.2.1.0^{2,6}]undecan-8-yl]acetaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](O)C[C@@]2(C)[C@H](C)[C@]3(CC=O)O[C@@H](OC3=O)[C@@]12C

InChI Identifier

InChI=1S/C15H22O5/c1-8-10(17)7-13(3)9(2)15(5-6-16)11(18)19-12(20-15)14(8,13)4/h6,8-10,12,17H,5,7H2,1-4H3/t8-,9+,10+,12-,13+,14-,15+/m1/s1

InChI Key

YZAVUVDOBXZQNS-JLPLLFGXSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Porella cordaeana	Plant	KNApSAcK
Porella platyphylla	LOTUS Database	35616633
Trocholejeunea sandvicensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Not Available

Direct Parent

Lactones

Alternative Parents

Substituents

Caprolactone
Oxepane
Oxane
Meta-dioxolane
Alpha-hydrogen aldehyde
Cyclic alcohol
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Oxacycle
Organic oxide
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
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	1.37	ALOGPS
logP	1.25	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.96	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.65 m³·mol⁻¹	ChemAxon
Polarizability	28.64 Å³	ChemAxon
Number of Rings	3	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

C00021343

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

14563790

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Porellapinguisanolide (NP0064381)

MOL for NP0064381 (Porellapinguisanolide)

3D MOL for NP0064381 (Porellapinguisanolide)

3D SDF for NP0064381 (Porellapinguisanolide)

3D-SDF for NP0064381 (Porellapinguisanolide)

PDB for NP0064381 (Porellapinguisanolide)

3D PDB for NP0064381 (Porellapinguisanolide)

SMILES for NP0064381 (Porellapinguisanolide)

INCHI for NP0064381 (Porellapinguisanolide)

Structure for NP0064381 (Porellapinguisanolide)

3D Structure for NP0064381 (Porellapinguisanolide)