NP-MRD: Showing NP-Card for 3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione (NP0328076)

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Record Information

Version

2.0

Created at

2022-09-12 11:13:04 UTC

Updated at

2022-09-12 11:13:04 UTC

NP-MRD ID

NP0328076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione

Description

3,8-Dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-2',6'-dihydro-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]Heptadecane-5,3'-pyran]-6',11,15-trione belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Based on a literature review very few articles have been published on 3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-2',6'-dihydro-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]Heptadecane-5,3'-pyran]-6',11,15-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213132D          

 34 39  0  0  0  0            999 V2000
    5.6078    0.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5410    1.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3441    1.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9760    1.0549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309122213132D          

 34 39  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0328076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C23C(=C)C4(C)OC(=O)C12OC1(C4O)C(=C)C2(CC(O)C31C)C=CC(=O)OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O9/c1-11-20(6)16(28)24-12(2)22(9-8-15(27)32-19(22,4)5)10-14(26)21(24,7)23(11)17(29)31-13(3)25(23,34-24)18(30)33-20/h8-9,13-14,16,26,28H,1-2,10H2,3-7H3

> <INCHI_KEY>
IEKBQVGQPACFOH-UHFFFAOYSA-N

> <FORMULA>
C25H28O9

> <MOLECULAR_WEIGHT>
472.49

> <EXACT_MASS>
472.173332482

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.97241799024039

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-2',6'-dihydro-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-6',11,15-trione

> <JCHEM_LOGP>
0.8471031286666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.522394566880457

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.728504119244395

> <JCHEM_PKA_STRONGEST_BASIC>
-3.013627548722593

> <JCHEM_POLAR_SURFACE_AREA>
128.59000000000003

> <JCHEM_REFRACTIVITY>
114.17779999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-6',11,15-trione

> <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      10.468   1.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.024   2.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.078   3.796   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.133   4.918   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.632   4.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.077   3.091   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.576   2.739   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.022   1.969   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.523   2.322   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.118   0.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.018   0.864   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.634   5.271   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.135   5.623   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.690   7.097   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.080   4.501   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.167   5.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.524   3.026   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.430   1.952   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.166   2.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.881   1.105   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.021  -0.173   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.515   1.020   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.505   2.261   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.932   0.781   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.951   4.122   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.824   5.391   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.994   3.973   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.411   4.401   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.658   5.745   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.861   2.531   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.454   3.683   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.487   4.881   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.309   3.318   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.629   4.111   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    9   12                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3   10   11                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   27                                             
CONECT   16   15                                                            
CONECT   17   15    2   18   33                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   27   31                                             
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25   33                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   19   15   28                                             
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   19   32                                                  
CONECT   32   31                                                            
CONECT   33   23   17   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₉

Average Mass

472.4900 Da

Monoisotopic Mass

472.17333 Da

IUPAC Name

3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-2',6'-dihydro-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-6',11,15-trione

Traditional Name

3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-6',11,15-trione

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C23C(=C)C4(C)OC(=O)C12OC1(C4O)C(=C)C2(CC(O)C31C)C=CC(=O)OC2(C)C

InChI Identifier

InChI=1S/C25H28O9/c1-11-20(6)16(28)24-12(2)22(9-8-15(27)32-19(22,4)5)10-14(26)21(24,7)23(11)17(29)31-13(3)25(23,34-24)18(30)33-20/h8-9,13-14,16,26,28H,1-2,10H2,3-7H3

InChI Key

IEKBQVGQPACFOH-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Furopyran
Furofuran
Oxepane
Delta_valerolactone
Dioxepane
Dihydropyranone
Delta valerolactone
1,4-dioxepane
Pyran
Oxane
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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
logP	0.85	ChemAxon
pKa (Strongest Acidic)	12.73	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	114.18 m³·mol⁻¹	ChemAxon
Polarizability	45.97 Å³	ChemAxon
Number of Rings	6	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

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

162991888

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione (NP0328076)

MOL for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D MOL for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D SDF for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D-SDF for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

PDB for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D PDB for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

SMILES for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

INCHI for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

Structure for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D Structure for NP0328076 (3,8-dihydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)