NP-MRD: Showing NP-Card for (1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate (NP0324043)

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Record Information

Version

2.0

Created at

2022-09-12 03:51:47 UTC

Updated at

2022-09-12 03:51:47 UTC

NP-MRD ID

NP0324043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate

Description

1,15-Seco-1,2,9,21-tetradehydro-2,15-dideoxy-8beta-hydroxy-15-oxoryanodol 3-(1H-pyrrole-2-carboxylate) belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate is found in Ryania speciosa. Based on a literature review very few articles have been published on 1,15-Seco-1,2,9,21-tetradehydro-2,15-dideoxy-8beta-hydroxy-15-oxoryanodol 3-(1H-pyrrole-2-carboxylate).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205512D          

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M  END

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M  END


  Mrv1652309122205512D          

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 25 34  1  0  0  0  0
  8 34  1  0  0  0  0
 17 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0324043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(C)[C@@]2(O)[C@@](O)([C@@H]1OC(=O)C1=CC=CN1)[C@@]1(C)CC(=O)O[C@@]22[C@H](O)C(=C)[C@@H](O)C[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO9/c1-11(2)17-13(4)23(32)24(33,19(17)34-20(30)14-7-6-8-26-14)21(5)10-16(28)35-25(23)18(29)12(3)15(27)9-22(21,25)31/h6-8,11,15,18-19,26-27,29,31-33H,3,9-10H2,1-2,4-5H3/t15-,18+,19+,21-,22-,23+,24+,25+/m0/s1

> <INCHI_KEY>
INKREVWPFYFIDX-PNKLSOHESA-N

> <FORMULA>
C25H31NO9

> <MOLECULAR_WEIGHT>
489.521

> <EXACT_MASS>
489.199881582

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.125406478724244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,6S,7S,8S,10S,12R)-2,6,8,10,12-pentahydroxy-3,7-dimethyl-11-methylidene-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0^{1,8}.0^{2,6}]pentadec-3-en-5-yl 1H-pyrrole-2-carboxylate

> <JCHEM_LOGP>
-0.5552739676666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.376772220063106

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.593340398714306

> <JCHEM_PKA_STRONGEST_BASIC>
-3.036264615071098

> <JCHEM_POLAR_SURFACE_AREA>
169.54

> <JCHEM_REFRACTIVITY>
120.03979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,6S,7S,8S,10S,12R)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0^{1,8}.0^{2,6}]pentadec-3-en-5-yl 1H-pyrrole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.384  -2.748   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.263  -1.692   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.617  -0.193   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.157  -0.228   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.496   0.863   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.021   0.421   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.482   0.401   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.567   2.145   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.890   3.651   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.070   1.783   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.420   0.387   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.120   0.367   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.106  -0.992   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667  -1.078   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.788  -2.134   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.434  -3.633   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.803  -0.339   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.475  -1.725   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.273  -0.796   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.195  -2.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.162   0.461   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.702   0.481   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.455   1.825   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.489  -0.842   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.241   1.695   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.698   3.166   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.200   3.506   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.245   2.375   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.657   4.976   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.115   5.471   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.096   7.011   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.625   7.468   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       6.736   6.210   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       3.783   1.201   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.038   2.719   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8   14                                             
CONECT    7    6                                                            
CONECT    8    6    9   10   34                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    6   15   17                                             
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18   19   34                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   25    8   17   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
1,15-Seco-1,2,9,21-tetradehydro-2,15-dideoxy-8b-hydroxy-15-oxoryanodol 3-(1H-pyrrole-2-carboxylate)	Generator
1,15-Seco-1,2,9,21-tetradehydro-2,15-dideoxy-8b-hydroxy-15-oxoryanodol 3-(1H-pyrrole-2-carboxylic acid)	Generator
1,15-Seco-1,2,9,21-tetradehydro-2,15-dideoxy-8beta-hydroxy-15-oxoryanodol 3-(1H-pyrrole-2-carboxylic acid)	Generator
1,15-Seco-1,2,9,21-tetradehydro-2,15-dideoxy-8β-hydroxy-15-oxoryanodol 3-(1H-pyrrole-2-carboxylate)	Generator
1,15-Seco-1,2,9,21-tetradehydro-2,15-dideoxy-8β-hydroxy-15-oxoryanodol 3-(1H-pyrrole-2-carboxylic acid)	Generator

Chemical Formula

C₂₅H₃₁NO₉

Average Mass

489.5210 Da

Monoisotopic Mass

489.19988 Da

IUPAC Name

(1R,2R,5R,6S,7S,8S,10S,12R)-2,6,8,10,12-pentahydroxy-3,7-dimethyl-11-methylidene-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0^{1,8}.0^{2,6}]pentadec-3-en-5-yl 1H-pyrrole-2-carboxylate

Traditional Name

(1R,2R,5R,6S,7S,8S,10S,12R)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0^{1,8}.0^{2,6}]pentadec-3-en-5-yl 1H-pyrrole-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(C)[C@@]2(O)[C@@](O)([C@@H]1OC(=O)C1=CC=CN1)[C@@]1(C)CC(=O)O[C@@]22[C@H](O)C(=C)[C@@H](O)C[C@]12O

InChI Identifier

InChI=1S/C25H31NO9/c1-11(2)17-13(4)23(32)24(33,19(17)34-20(30)14-7-6-8-26-14)21(5)10-16(28)35-25(23)18(29)12(3)15(27)9-22(21,25)31/h6-8,11,15,18-19,26-27,29,31-33H,3,9-10H2,1-2,4-5H3/t15-,18+,19+,21-,22-,23+,24+,25+/m0/s1

InChI Key

INKREVWPFYFIDX-PNKLSOHESA-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
Ryania speciosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Caprolactone
Pyrrole-2-carboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxepane
Dicarboxylic acid or derivatives
Oxane
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Alcohol
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	-0.56	ChemAxon
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	169.54 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.04 m³·mol⁻¹	ChemAxon
Polarizability	49.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

101177509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate (NP0324043)

MOL for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

3D MOL for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

3D SDF for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

3D-SDF for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

PDB for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

3D PDB for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

SMILES for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

INCHI for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

Structure for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)

3D Structure for NP0324043 ((1r,2r,5r,6s,7s,8s,10s,12r)-2,6,8,10,12-pentahydroxy-4-isopropyl-3,7-dimethyl-11-methylidene-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-5-yl 1h-pyrrole-2-carboxylate)