NP-MRD: Showing NP-Card for (1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate (NP0219143)

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Record Information

Version

2.0

Created at

2022-09-05 20:02:58 UTC

Updated at

2022-09-05 20:02:58 UTC

NP-MRD ID

NP0219143

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate

Description

Penstemide aglycone belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate is found in Penstemon serrulatus. Based on a literature review very few articles have been published on Penstemide aglycone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222022D          

 21 22  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   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 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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165   -1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5152   -0.8205    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
  8 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0219143

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O5/c1-10(2)6-14(19)21-15-16(3)12(8-18)4-5-13(16)11(7-17)9-20-15/h4,9-10,13,15,17-18H,5-8H2,1-3H3/t13-,15-,16+/m0/s1

> <INCHI_KEY>
WIGSASLHMYPLHW-CWRNSKLLSA-N

> <FORMULA>
C16H24O5

> <MOLECULAR_WEIGHT>
296.363

> <EXACT_MASS>
296.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.642969880975244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,7aS)-4,7-bis(hydroxymethyl)-7a-methyl-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <JCHEM_LOGP>
1.0700137969999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.397111212023297

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.79069734411232

> <JCHEM_PKA_STRONGEST_BASIC>
-2.738697222329697

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
78.65259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7aS)-4,7-bis(hydroxymethyl)-7a-methyl-1H,4aH,5H-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.608  -1.941   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.577  -3.085   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.828  -1.532   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    8   14   21                                             
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₄O₅

Average Mass

296.3630 Da

Monoisotopic Mass

296.16237 Da

IUPAC Name

(1S,4aS,7aS)-4,7-bis(hydroxymethyl)-7a-methyl-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

Traditional Name

(1S,4aS,7aS)-4,7-bis(hydroxymethyl)-7a-methyl-1H,4aH,5H-cyclopenta[c]pyran-1-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@@H]1OC=C(CO)[C@@H]2CC=C(CO)[C@@]12C

InChI Identifier

InChI=1S/C16H24O5/c1-10(2)6-14(19)21-15-16(3)12(8-18)4-5-13(16)11(7-17)9-20-15/h4,9-10,13,15,17-18H,5-8H2,1-3H3/t13-,15-,16+/m0/s1

InChI Key

WIGSASLHMYPLHW-CWRNSKLLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penstemon serrulatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Bicyclic monoterpenoid
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen compound
Primary alcohol
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
logP	1.07	ChemAxon
pKa (Strongest Acidic)	14.79	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.65 m³·mol⁻¹	ChemAxon
Polarizability	31.64 Å³	ChemAxon
Number of Rings	2	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

24718932

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44576038

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate (NP0219143)

MOL for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D MOL for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D SDF for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D-SDF for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

PDB for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D PDB for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

SMILES for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

INCHI for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

Structure for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D Structure for NP0219143 ((1s,4as,7as)-4,7-bis(hydroxymethyl)-7a-methyl-1h,4ah,5h-cyclopenta[c]pyran-1-yl 3-methylbutanoate)