NP-MRD: Showing NP-Card for (1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one (NP0232519)

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Record Information

Version

2.0

Created at

2022-09-06 13:47:12 UTC

Updated at

2022-09-06 13:47:12 UTC

NP-MRD ID

NP0232519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

Description

Coagulin F belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. (1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one is found in Withania coagulans. (1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one was first documented in 1998 (PMID: 9644072). Based on a literature review very few articles have been published on Coagulin F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062215472D          

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M  END

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M  END


  Mrv1652309062215472D          

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M  END
> <DATABASE_ID>
NP0232519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(CO)C(=O)O[C@H](C1)[C@@]1(C)O[C@@]23CC[C@H]1[C@@]2(C)CC[C@H]1[C@H]3CC=C2C=CCC(=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O5/c1-16-14-23(32-24(31)18(16)15-29)27(4)21-11-13-28(33-27)20-9-8-17-6-5-7-22(30)26(17,3)19(20)10-12-25(21,28)2/h5-6,8,19-21,23,29H,7,9-15H2,1-4H3/t19-,20+,21-,23+,25+,26-,27-,28+/m0/s1

> <INCHI_KEY>
XLKFUJPNXPVFRF-LXSIAZRUSA-N

> <FORMULA>
C28H36O5

> <MOLECULAR_WEIGHT>
452.591

> <EXACT_MASS>
452.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
42.13071355978229

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,10R,11S,14R,15S,16S)-16-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0^{1,14}.0^{2,11}.0^{5,10}]nonadeca-4,6-dien-9-one

> <JCHEM_LOGP>
3.807156935666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.476040226105287

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.749032244762613

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8539271164036695

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
126.87309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,10R,11S,14R,15S,16S)-16-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0^{1,14}.0^{2,11}.0^{5,10}]nonadeca-4,6-dien-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.587  -4.050   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.074  -3.766   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.929  -4.935   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.418  -6.388   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.096  -6.671   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.442  -4.651   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.445  -5.820   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.953  -3.199   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.951  -2.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.462  -0.577   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.804  -1.332   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.439   0.613   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.897   2.055   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.378   2.306   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.400   1.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.943  -0.326   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.238   0.663   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.041   1.632   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.113  -0.604   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.648  -0.479   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.307   0.913   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.432   2.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.091   3.571   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.626   3.696   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.502   2.430   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.037   2.554   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.912   1.288   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.253  -0.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.718  -0.229   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.059  -1.621   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.842   1.038   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.183  -0.354   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.437  -2.313   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   17   22                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16   13   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   13   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   25   21   32                                             
CONECT   32   31                                                            
CONECT   33    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
27-Hydroxy-14,20-epoxy-1-oxowitha-3,5,24-trienolide	MeSH

Chemical Formula

C₂₈H₃₆O₅

Average Mass

452.5910 Da

Monoisotopic Mass

452.25627 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=C(CO)C(=O)O[C@H](C1)[C@@]1(C)O[C@@]23CC[C@H]1[C@@]2(C)CC[C@H]1[C@H]3CC=C2C=CCC(=O)[C@]12C

InChI Identifier

InChI=1S/C28H36O5/c1-16-14-23(32-24(31)18(16)15-29)27(4)21-11-13-28(33-27)20-9-8-17-6-5-7-22(30)26(17,3)19(20)10-12-25(21,28)2/h5-6,8,19-21,23,29H,7,9-15H2,1-4H3/t19-,20+,21-,23+,25+,26-,27-,28+/m0/s1

InChI Key

XLKFUJPNXPVFRF-LXSIAZRUSA-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
Withania coagulans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
1-oxosteroid
Oxosteroid
Naphthofuran
Dihydropyranone
Cyclohexenone
Oxane
Pyran
Oxolane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Primary alcohol
Organic oxygen compound
Carbonyl group
Alcohol
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

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

24941991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Atta-ur-Rahman A, Choudhary MI, Qureshi S, Gul W, Yousaf M: Two new ergostane-type steroidal lactones from Withania coagulans. J Nat Prod. 1998 Jun 26;61(6):812-4. doi: 10.1021/np970478p. [PubMed:9644072 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one (NP0232519)

MOL for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D MOL for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D SDF for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D-SDF for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

PDB for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D PDB for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

SMILES for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

INCHI for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

Structure for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D Structure for NP0232519 ((1r,2r,10r,11s,14r,15s,16s)-16-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)