NP-MRD: Showing NP-Card for (5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0229115)

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Record Information

Version

2.0

Created at

2022-09-06 09:02:28 UTC

Updated at

2022-09-06 09:02:28 UTC

NP-MRD ID

NP0229115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

(5-Hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as iridoid o-glycosides. (5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Penstemon acuminatus. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton (5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161505012D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161505012D          

 37 40  0  0  0  0            999 V2000
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 17 18  2  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 20 33  1  0  0  0  0
 12 33  1  0  0  0  0
 16 33  1  0  0  0  0
  5 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)OCC2=CC(O)C3C=COC(OC4OC(CO)C(O)C(O)C4O)C23)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O12/c1-33-17-8-12(2-4-15(17)27)3-5-19(29)35-11-13-9-16(28)14-6-7-34-24(20(13)14)37-25-23(32)22(31)21(30)18(10-26)36-25/h2-9,14,16,18,20-28,30-32H,10-11H2,1H3

> <INCHI_KEY>
UBIOBPKBEZMDGP-UHFFFAOYSA-N

> <FORMULA>
C25H30O12

> <MOLECULAR_WEIGHT>
522.503

> <EXACT_MASS>
522.173726406

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.659456992396315

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-0.6092157716666665

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.206434395056707

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.865761775641907

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615635954

> <JCHEM_POLAR_SURFACE_AREA>
184.6

> <JCHEM_REFRACTIVITY>
127.18860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -9.449  -3.646   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.943  -3.325   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.912  -4.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.406  -4.150   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.376  -5.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.852  -6.759   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.358  -7.079   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.388  -5.934   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -8.895  -6.255   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   33                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   20   12   16                                                  
CONECT   34    5   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(5-Hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₀O₁₂

Average Mass

522.5030 Da

Monoisotopic Mass

522.17373 Da

IUPAC Name

(5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)OCC2=CC(O)C3C=COC(OC4OC(CO)C(O)C(O)C4O)C23)=CC=C1O

InChI Identifier

InChI=1S/C25H30O12/c1-33-17-8-12(2-4-15(17)27)3-5-19(29)35-11-13-9-16(28)14-6-7-34-24(20(13)14)37-25-23(32)22(31)21(30)18(10-26)36-25/h2-9,14,16,18,20-28,30-32H,10-11H2,1H3

InChI Key

UBIOBPKBEZMDGP-UHFFFAOYSA-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
Penstemon acuminatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Methoxyphenol
Bicyclic monoterpenoid
Monoterpenoid
Aromatic monoterpenoid
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Styrene
Phenol
Fatty acid ester
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Acetal
Primary alcohol
Carbonyl group
Alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-0.12	ALOGPS
logP	-0.61	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.19 m³·mol⁻¹	ChemAxon
Polarizability	51.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0229115)

MOL for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0229115 ((5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)