NP-MRD: Showing NP-Card for (1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione (NP0194806)

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Record Information

Version

2.0

Created at

2022-09-04 12:33:01 UTC

Updated at

2022-09-04 12:33:01 UTC

NP-MRD ID

NP0194806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione

Description

Jaborosalactone 1 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. (1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione is found in Jaborosa runcinata. Based on a literature review a small amount of articles have been published on jaborosalactone 1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214332D          

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M  END

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M  END


  Mrv1652309042214332D          

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M  END
> <DATABASE_ID>
NP0194806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)[C@]2(OC1=O)C(=O)C(C)=C1CC[C@H]3[C@@H]4C[C@H]5O[C@]55CC=CC(=O)[C@]5(C)[C@H]4C[C@@]2(O)[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O6/c1-13-15(3)28(34-23(13)31)22(30)14(2)17-8-9-18-16-11-21-26(33-21)10-6-7-20(29)25(26,5)19(16)12-27(28,32)24(17,18)4/h6-7,16,18-19,21,32H,8-12H2,1-5H3/t16-,18-,19-,21+,24+,25-,26+,27+,28-/m0/s1

> <INCHI_KEY>
HUXPYRJEVUAXLN-YCEUDUMWSA-N

> <FORMULA>
C28H32O6

> <MOLECULAR_WEIGHT>
464.558

> <EXACT_MASS>
464.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.90018391715743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,2'S,4'R,6'S,11'R,12'S,14'R,21'S)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5H-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0^{2,12}.0^{4,6}.0^{6,11}.0^{18,21}]henicosane]-8',17'-diene-5,10',16'-trione

> <JCHEM_LOGP>
3.856217721666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.646542228565302

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.95835616030411

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6877790242002852

> <JCHEM_POLAR_SURFACE_AREA>
93.19999999999999

> <JCHEM_REFRACTIVITY>
124.63559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,4'R,6'S,11'R,12'S,14'R,21'S)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0^{2,12}.0^{4,6}.0^{6,11}.0^{18,21}]henicosane]-8',17'-diene-5,10',16'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.684   4.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.462   2.871   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   2.880   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.026   4.031   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.437   3.413   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.285   1.881   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.322   0.743   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.827   1.072   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.864  -0.066   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.901  -1.204   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.397  -1.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.435  -2.672   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.968  -4.139   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.463  -4.469   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.426  -3.331   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.921  -3.660   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.893  -1.863   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.388  -2.192   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.855  -0.725   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.351  -1.054   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.019   0.213   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.922  -1.324   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.781   1.551   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.693   0.311   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.479   0.204   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.114  -1.199   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.975  -2.237   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.146  -3.767   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.637  -1.475   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.234  -2.110   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.948   0.033   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.911   1.172   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.701   1.533   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.233   2.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    9   12   17                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23   25                                             
CONECT   22   21                                                            
CONECT   23   21    3    6   24                                             
CONECT   24   23                                                            
CONECT   25   21   26   31   33                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   25   32                                                  
CONECT   32   31                                                            
CONECT   33   25    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₆

Average Mass

464.5580 Da

Monoisotopic Mass

464.21989 Da

IUPAC Name

(1'S,2R,2'S,4'R,6'S,11'R,12'S,14'R,21'S)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5H-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0^{2,12}.0^{4,6}.0^{6,11}.0^{18,21}]henicosane]-8',17'-diene-5,10',16'-trione

Traditional Name

(1'S,2R,2'S,4'R,6'S,11'R,12'S,14'R,21'S)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0^{2,12}.0^{4,6}.0^{6,11}.0^{18,21}]henicosane]-8',17'-diene-5,10',16'-trione

CAS Registry Number

Not Available

SMILES

CC1=C(C)[C@]2(OC1=O)C(=O)C(C)=C1CC[C@H]3[C@@H]4C[C@H]5O[C@]55CC=CC(=O)[C@]5(C)[C@H]4C[C@@]2(O)[C@]13C

InChI Identifier

InChI=1S/C28H32O6/c1-13-15(3)28(34-23(13)31)22(30)14(2)17-8-9-18-16-11-21-26(33-21)10-6-7-20(29)25(26,5)19(16)12-27(28,32)24(17,18)4/h6-7,16,18-19,21,32H,8-12H2,1-5H3/t16-,18-,19-,21+,24+,25-,26+,27+,28-/m0/s1

InChI Key

HUXPYRJEVUAXLN-YCEUDUMWSA-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
Jaborosa runcinata	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
Oxepane
Cyclohexenone
Alpha-acyloxy ketone
2-furanone
Cyclic alcohol
Dihydrofuran
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
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	3.86	ChemAxon
pKa (Strongest Acidic)	12.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	124.64 m³·mol⁻¹	ChemAxon
Polarizability	48.9 Å³	ChemAxon
Number of Rings	7	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

8703510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10528114

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione (NP0194806)

MOL for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

3D MOL for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

3D SDF for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

3D-SDF for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

PDB for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

3D PDB for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

SMILES for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

INCHI for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

Structure for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)

3D Structure for NP0194806 ((1's,2r,2's,4'r,6's,11'r,12's,14'r,21's)-14'-hydroxy-3,4,11',17',21'-pentamethyl-5'-oxaspiro[furan-2,15'-hexacyclo[12.6.1.0²,¹².0⁴,⁶.0⁶,¹¹.0¹⁸,²¹]henicosane]-8',17'-diene-5,10',16'-trione)