NP-MRD: Showing NP-Card for 2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione (NP0319785)

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Record Information

Version

2.0

Created at

2022-09-11 21:00:22 UTC

Updated at

2022-09-11 21:00:22 UTC

NP-MRD ID

NP0319785

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione

Description

4',5',13',15',17'-Pentahydroxy-3,4,10',16',20'-pentamethyl-5H-spiro[furan-2,14'-pentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]Icosan]-7'-ene-5,9'-dione 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. 2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione is found in Jaborosa odonelliana. 4',5',13',15',17'-Pentahydroxy-3,4,10',16',20'-pentamethyl-5H-spiro[furan-2,14'-pentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]Icosan]-7'-ene-5,9'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251513392D          

 36 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004251513392D          

 36 41  0  0  0  0            999 V2000
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    3.7127   -0.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -1.6834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3098   -0.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    0.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 16 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 13 35  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319785

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)C2(OC(=O)C(C)=C2C)C2(O)CC3C(CC(O)C4(O)CC=CC(=O)C34C)C3CCC1(O)C23C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O8/c1-13-14(2)28(36-22(13)32)21(31)15(3)25(33)10-8-17-16-11-20(30)26(34)9-6-7-19(29)23(26,4)18(16)12-27(28,35)24(17,25)5/h6-7,15-18,20-21,30-31,33-35H,8-12H2,1-5H3

> <INCHI_KEY>
OSAOWATUTILJKL-UHFFFAOYSA-N

> <FORMULA>
C28H38O8

> <MOLECULAR_WEIGHT>
502.604

> <EXACT_MASS>
502.256668184

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.99188464715479

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4',5',13',15',17'-pentahydroxy-3,4,10',16',20'-pentamethyl-5H-spiro[furan-2,14'-pentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icosan]-7'-ene-5,9'-dione

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.0285000776666657

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.209190615783449

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.702406365791152

> <JCHEM_PKA_STRONGEST_BASIC>
-3.230806364276969

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
129.68509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4',5',13',15',17'-pentahydroxy-3,4,10',16',20'-pentamethylspiro[furan-2,14'-pentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icosan]-7'-ene-5,9'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.078  -2.209   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.453  -1.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.090   0.143   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.464  -0.077   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.205   1.206   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.781   1.792   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.898   3.328   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.713   4.423   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.395   3.691   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.029   2.511   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.382   3.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.255   5.364   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.682   0.772   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.990   2.294   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.313   1.622   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.668   0.890   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.711  -0.649   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.066  -1.381   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.378  -0.573   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.302  -1.904   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.334   0.966   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.834   0.232   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.645   1.774   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.601   3.313   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.246   4.045   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.935   3.237   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.029   4.956   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.979   1.698   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.991   3.158   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.400  -1.457   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.123  -2.971   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.596  -3.176   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.930  -1.787   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.982  -3.142   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.045  -0.725   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.290   0.244   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10   13                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    5   14   15   35                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   28                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   16   21   29                                             
CONECT   29   28                                                            
CONECT   30   17   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    2   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   13   30   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₈

Average Mass

502.6040 Da

Monoisotopic Mass

502.25667 Da

IUPAC Name

4',5',13',15',17'-pentahydroxy-3,4,10',16',20'-pentamethyl-5H-spiro[furan-2,14'-pentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icosan]-7'-ene-5,9'-dione

Traditional Name

4',5',13',15',17'-pentahydroxy-3,4,10',16',20'-pentamethylspiro[furan-2,14'-pentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icosan]-7'-ene-5,9'-dione

CAS Registry Number

Not Available

SMILES

CC1C(O)C2(OC(=O)C(C)=C2C)C2(O)CC3C(CC(O)C4(O)CC=CC(=O)C34C)C3CCC1(O)C23C

InChI Identifier

InChI=1S/C28H38O8/c1-13-14(2)28(36-22(13)32)21(31)15(3)25(33)10-8-17-16-11-20(30)26(34)9-6-7-19(29)23(26,4)18(16)12-27(28,35)24(17,25)5/h6-7,15-18,20-21,30-31,33-35H,8-12H2,1-5H3

InChI Key

OSAOWATUTILJKL-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
Jaborosa odonelliana	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
22-hydroxysteroid
12-hydroxysteroid
6-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
1-oxosteroid
17-hydroxysteroid
Oxosteroid
Cyclohexenone
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Carbonyl group
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	0.93	ALOGPS
logP	1.03	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	129.69 m³·mol⁻¹	ChemAxon
Polarizability	52.99 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

85297970

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione (NP0319785)

MOL for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

3D MOL for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

3D SDF for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

3D-SDF for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

PDB for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

3D PDB for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

SMILES for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

INCHI for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

Structure for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)

3D Structure for NP0319785 (2a,4,5a,10a,11-pentahydroxy-3,3',4',6b,12c-pentamethyl-2,3,4,6,6a,10,11,12,12a,12b-decahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-5',7-dione)