NP-MRD: Showing NP-Card for (1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate (NP0203983)

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Record Information

Version

2.0

Created at

2022-09-04 23:34:22 UTC

Updated at

2022-09-04 23:34:22 UTC

NP-MRD ID

NP0203983

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate

Description

(10Beta)-9,21-Didehydroryanodol 3-(1H-pyrrole-2-carboxylate) belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate is found in Ryania speciosa. Based on a literature review very few articles have been published on (10beta)-9,21-Didehydroryanodol 3-(1H-pyrrole-2-carboxylate).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201342D          

 35 40  0  0  1  0            999 V2000
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M  END

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  Mrv1652309052201342D          

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 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  1  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 29 34  1  0  0  0  0
 10 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0203983

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@]1(O)[C@@H](OC(=O)C2=CC=CN2)[C@@]2(O)[C@@]3(C)C[C@]4(O)O[C@@]5([C@@H](O)C(=C)CC[C@]35O)[C@@]2(O)[C@]14C

> <INCHI_IDENTIFIER>
InChI=1S/C25H33NO9/c1-12(2)22(31)17(34-16(28)14-7-6-10-26-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)8-9-20(18,24)29/h6-7,10,12,15,17,26-27,29-33H,3,8-9,11H2,1-2,4-5H3/t15-,17+,18-,19-,20-,21-,22+,23+,24+,25+/m0/s1

> <INCHI_KEY>
BPFNBBLVUYSFRK-NLMSCGQMSA-N

> <FORMULA>
C25H33NO9

> <MOLECULAR_WEIGHT>
491.537

> <EXACT_MASS>
491.215531647

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
44.36606334545724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6S,7S,9S,10S,11S,12R,13S,14R)-2,6,9,11,13,14-hexahydroxy-7,10-dimethyl-3-methylidene-11-(propan-2-yl)-15-oxapentacyclo[7.5.1.0^{1,6}.0^{7,13}.0^{10,14}]pentadecan-12-yl 1H-pyrrole-2-carboxylate

> <JCHEM_LOGP>
-0.16783997333333436

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.84229992725322

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.21829037516573

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5571291916151226

> <JCHEM_POLAR_SURFACE_AREA>
172.7

> <JCHEM_REFRACTIVITY>
118.7634

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6S,7S,9S,10S,11S,12R,13S,14R)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0^{1,6}.0^{7,13}.0^{10,14}]pentadecan-12-yl 1H-pyrrole-2-carboxylate

> <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      12.146   1.910   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.146   0.739   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.686  -0.732   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.531  -1.805   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.979  -1.410   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.265  -2.923   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.655  -2.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.813  -3.377   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.914  -3.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.170  -2.346   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.833  -3.111   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.474  -1.238   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.335   0.068   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.586   1.047   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.228   2.545   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.673   0.276   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.230   1.751   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.389  -1.117   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.238  -2.141   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.298   0.285   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.706   1.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.624   2.866   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.134   2.477   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.031   4.351   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.070   5.554   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.916   6.840   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.401   6.432   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       6.473   4.894   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       3.859  -0.280   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.896  -1.481   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.946   0.961   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.616   2.465   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.415   0.790   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.288  -0.909   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.275  -2.070   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8    9   18                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   34                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    5   14   16                                             
CONECT   14   13    2   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17   18   34                                             
CONECT   17   16                                                            
CONECT   18   16    7   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   20   30   31   34                                             
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   10   16   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
(10b)-9,21-Didehydroryanodol 3-(1H-pyrrole-2-carboxylate)	Generator
(10b)-9,21-Didehydroryanodol 3-(1H-pyrrole-2-carboxylic acid)	Generator
(10beta)-9,21-Didehydroryanodol 3-(1H-pyrrole-2-carboxylic acid)	Generator
(10Β)-9,21-didehydroryanodol 3-(1H-pyrrole-2-carboxylate)	Generator
(10Β)-9,21-didehydroryanodol 3-(1H-pyrrole-2-carboxylic acid)	Generator

Chemical Formula

C₂₅H₃₃NO₉

Average Mass

491.5370 Da

Monoisotopic Mass

491.21553 Da

IUPAC Name

(1R,2S,6S,7S,9S,10S,11S,12R,13S,14R)-2,6,9,11,13,14-hexahydroxy-7,10-dimethyl-3-methylidene-11-(propan-2-yl)-15-oxapentacyclo[7.5.1.0^{1,6}.0^{7,13}.0^{10,14}]pentadecan-12-yl 1H-pyrrole-2-carboxylate

Traditional Name

(1R,2S,6S,7S,9S,10S,11S,12R,13S,14R)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0^{1,6}.0^{7,13}.0^{10,14}]pentadecan-12-yl 1H-pyrrole-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC(C)[C@@]1(O)[C@@H](OC(=O)C2=CC=CN2)[C@@]2(O)[C@@]3(C)C[C@]4(O)O[C@@]5([C@@H](O)C(=C)CC[C@]35O)[C@@]2(O)[C@]14C

InChI Identifier

InChI=1S/C25H33NO9/c1-12(2)22(31)17(34-16(28)14-7-6-10-26-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)8-9-20(18,24)29/h6-7,10,12,15,17,26-27,29-33H,3,8-9,11H2,1-2,4-5H3/t15-,17+,18-,19-,20-,21-,22+,23+,24+,25+/m0/s1

InChI Key

BPFNBBLVUYSFRK-NLMSCGQMSA-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 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

Substituents

Ryanodane diterpenoid
Diterpenoid
Pyrrole-2-carboxylic acid or derivatives
Oxepane
Substituted pyrrole
Oxane
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Pyrrole
Cyclic alcohol
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
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	-0.17	ChemAxon
pKa (Strongest Acidic)	11.22	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	172.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.76 m³·mol⁻¹	ChemAxon
Polarizability	44.37 Å³	ChemAxon
Number of Rings	6	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

101177506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate (NP0203983)

MOL for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

3D MOL for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

3D SDF for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

3D-SDF for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

PDB for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

3D PDB for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

SMILES for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

INCHI for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

Structure for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)

3D Structure for NP0203983 ((1r,2s,6s,7s,9s,10s,11s,12r,13s,14r)-2,6,9,11,13,14-hexahydroxy-11-isopropyl-7,10-dimethyl-3-methylidene-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl 1h-pyrrole-2-carboxylate)