NP-MRD: Showing NP-Card for 3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one (NP0209967)

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Record Information

Version

2.0

Created at

2022-09-05 07:34:55 UTC

Updated at

2022-09-05 07:34:55 UTC

NP-MRD ID

NP0209967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one

Description

3,11'-Dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-1,5-dihydro-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]Tridecane]-1'(13'),9',11'-trien-5-one belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. 3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one is found in Penicillium citrinum. Based on a literature review very few articles have been published on 3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-1,5-dihydro-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]Tridecane]-1'(13'),9',11'-trien-5-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052209342D          

 35 38  0  0  0  0            999 V2000
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M  END

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  Mrv1652309052209342D          

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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0209967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(C)C(=O)C1=C(O)C2(OC3=CC(O)=C(C)C4=C3C(OC(C)C4C)C2C)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO6/c1-8-9-10-11-12-14(2)24(31)23-26(32)28(29(7)27(23)33)17(5)25-22-20(35-28)13-19(30)16(4)21(22)15(3)18(6)34-25/h13-15,17-18,25,30,32H,8-12H2,1-7H3

> <INCHI_KEY>
YSKWCQSQBCPRCU-UHFFFAOYSA-N

> <FORMULA>
C28H39NO6

> <MOLECULAR_WEIGHT>
485.621

> <EXACT_MASS>
485.27773798

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.23915480866831

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-1,5-dihydro-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0^{5,13}]tridecane]-1'(12'),9'(13'),10'-trien-5-one

> <JCHEM_LOGP>
6.154185804000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.718477643351905

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4158572251554489

> <JCHEM_PKA_STRONGEST_BASIC>
2.1104650565678305

> <JCHEM_POLAR_SURFACE_AREA>
96.30000000000001

> <JCHEM_REFRACTIVITY>
134.7808

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0^{5,13}]tridecane]-1'(12'),9'(13'),10'-trien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0     -12.769   8.732   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.435   9.502   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.101   8.732   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.768   9.502   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.434   8.732   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.100   9.502   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.766   8.732   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.766   7.192   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.433   9.502   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.433  11.042   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.099   8.732   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.692   9.358   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.372  10.865   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.338   8.214   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.243   6.968   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.775   7.129   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.680   5.883   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.212   6.044   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.117   4.798   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.838   7.451   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.370   7.612   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.933   8.697   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.401   8.536   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.496   9.782   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.123  11.189   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.654  11.350   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.280  12.757   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.559  10.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.091  10.265   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.965   9.621   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.489  11.086   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -0.432   6.880   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       0.195   5.474   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.938   7.201   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.083   6.170   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   34                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   30   32                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   16   24                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22   29                                                  
CONECT   29   28                                                            
CONECT   30   24   14   31                                                  
CONECT   31   30                                                            
CONECT   32   14   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   11   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO₆

Average Mass

485.6210 Da

Monoisotopic Mass

485.27774 Da

IUPAC Name

3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-1,5-dihydro-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0^{5,13}]tridecane]-1'(12'),9'(13'),10'-trien-5-one

Traditional Name

3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0^{5,13}]tridecane]-1'(12'),9'(13'),10'-trien-5-one

CAS Registry Number

Not Available

SMILES

CCCCCCC(C)C(=O)C1=C(O)C2(OC3=CC(O)=C(C)C4=C3C(OC(C)C4C)C2C)N(C)C1=O

InChI Identifier

InChI=1S/C28H39NO6/c1-8-9-10-11-12-14(2)24(31)23-26(32)28(29(7)27(23)33)17(5)25-22-20(35-28)13-19(30)16(4)21(22)15(3)18(6)34-25/h13-15,17-18,25,30,32H,8-12H2,1-7H3

InChI Key

YSKWCQSQBCPRCU-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
Penicillium citrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Tertiary carboxylic acid amide
Pyrroline
Lactam
Ketone
Carboxamide group
Oxacycle
Azacycle
Ether
Enol
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	6.15	ChemAxon
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	2.11	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.78 m³·mol⁻¹	ChemAxon
Polarizability	55.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162958884

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one (NP0209967)

MOL for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

3D MOL for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

3D SDF for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

3D-SDF for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

PDB for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

3D PDB for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

SMILES for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

INCHI for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

Structure for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)

3D Structure for NP0209967 (3,11'-dihydroxy-1,4',7',8',10'-pentamethyl-4-(2-methyloctanoyl)-2',6'-dioxaspiro[pyrrole-2,3'-tricyclo[7.3.1.0⁵,¹³]tridecane]-1'(12'),9'(13'),10'-trien-5-one)