NP-MRD: Showing NP-Card for 12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione (NP0274692)

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Record Information

Version

2.0

Created at

2022-09-08 22:10:28 UTC

Updated at

2022-09-08 22:10:28 UTC

NP-MRD ID

NP0274692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

Description

12'-Hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]Hexadecan]-6'-ene-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. 12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione is found in Melia azedarach. 12'-Hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]Hexadecan]-6'-ene-6,11',15'-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121514272D          

 32 36  0  0  0  0            999 V2000
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    0.7147    2.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355    1.4999    0.0000 C   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


  Mrv0541 04121514272D          

 32 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0274692

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C23C(=C)C(C)(CC4=C(C)C5(CCC24C)C=CC(=O)OC5(C)C)OC(=O)C13O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O7/c1-13-16-12-22(7)14(2)24(18(27)30-15(3)25(24,29)19(28)32-22)21(16,6)10-11-23(13)9-8-17(26)31-20(23,4)5/h8-9,15,29H,2,10-12H2,1,3-7H3

> <INCHI_KEY>
SMCXRHPIVKSWIP-UHFFFAOYSA-N

> <FORMULA>
C25H30O7

> <MOLECULAR_WEIGHT>
442.508

> <EXACT_MASS>
442.199153306

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.46615190779748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.5811001203333337

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.789516297145743

> <JCHEM_PKA_STRONGEST_BASIC>
-4.640465571628451

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
114.55069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -1.394   3.599   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.023   2.996   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   3.823   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.493   2.800   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.982   3.194   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.973   1.283   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.729  -0.076   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.244  -0.348   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.476  -1.479   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.211  -2.995   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.045  -1.798   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.146  -0.650   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.665  -0.904   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.204  -2.347   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.644   0.284   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.105   1.726   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.586   1.981   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.607   0.792   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.159   2.266   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.624   1.472   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.143   1.218   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.682  -0.225   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.201  -0.479   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.702  -1.413   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.184  -1.159   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.876  -2.668   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.773  -2.582   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.108  -1.245   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.719   0.225   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.240   0.464   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.339   1.468   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.153   1.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   18   31                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   28                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20   25                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    6   12   19                                             
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   15   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    9   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2    6   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₇

Average Mass

442.5080 Da

Monoisotopic Mass

442.19915 Da

IUPAC Name

12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

Traditional Name

12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C23C(=C)C(C)(CC4=C(C)C5(CCC24C)C=CC(=O)OC5(C)C)OC(=O)C13O

InChI Identifier

InChI=1S/C25H30O7/c1-13-16-12-22(7)14(2)24(18(27)30-15(3)25(24,29)19(28)32-22)21(16,6)10-11-23(13)9-8-17(26)31-20(23,4)5/h8-9,15,29H,2,10-12H2,1,3-7H3

InChI Key

SMCXRHPIVKSWIP-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
Melia azedarach	LOTUS Database	35616633

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

Furopyran
Tricarboxylic acid or derivatives
Delta valerolactone
Dihydropyranone
Delta_valerolactone
Gamma butyrolactone
Oxane
Pyran
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
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	2.89	ALOGPS
logP	2.58	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.79	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	114.55 m³·mol⁻¹	ChemAxon
Polarizability	45.47 Å³	ChemAxon
Number of Rings	5	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione (NP0274692)

MOL for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D MOL for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D SDF for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D-SDF for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

PDB for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D PDB for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

SMILES for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

INCHI for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

Structure for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D Structure for NP0274692 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)