NP-MRD: Showing NP-Card for 2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one (NP0205672)

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Record Information

Version

2.0

Created at

2022-09-05 01:37:59 UTC

Updated at

2022-09-05 01:37:59 UTC

NP-MRD ID

NP0205672

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one

Description

2,13'-Dihydroxy-4',4',7,7,12'-pentamethyl-8,9-dihydro-7H-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecan]-13'-en-9-one belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one is found in Penicillium herquei. Based on a literature review very few articles have been published on 2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8,9-dihydro-7H-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecan]-13'-en-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052203382D          

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M  END

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  2 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
  7 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205672

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCN2CC34CC5(C(O)=NC6=C5C=CC5=C6C(=O)CC(C)(C)O5)C(C)(C)C3CC12C(O)=N4

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O4/c1-14-8-9-30-13-25-12-26(24(4,5)18(25)11-27(14,30)22(33)29-25)15-6-7-17-19(20(15)28-21(26)32)16(31)10-23(2,3)34-17/h6-7,14,18H,8-13H2,1-5H3,(H,28,32)(H,29,33)

> <INCHI_KEY>
QHKDAOMEFDLNBK-UHFFFAOYSA-N

> <FORMULA>
C27H33N3O4

> <MOLECULAR_WEIGHT>
463.578

> <EXACT_MASS>
463.247106555

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.33024518394082

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8,9-dihydro-7H-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-9-one

> <JCHEM_LOGP>
0.8998539298209038

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
4.256664872832067

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.035513719349163

> <JCHEM_PKA_STRONGEST_BASIC>
8.789286380976952

> <JCHEM_POLAR_SURFACE_AREA>
94.72

> <JCHEM_REFRACTIVITY>
129.00699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8H-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-9-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       0.160  -1.406   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.334   0.124   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.894   1.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.234   2.521   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.364   2.471   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.543   3.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.133   3.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.524   3.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.787   2.934   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.338   4.372   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.499   5.663   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       8.876   4.291   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.275   2.804   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.984   1.965   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.065   0.427   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.437  -0.272   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.728   0.567   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.647   2.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.939   2.944   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.858   4.482   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.311   2.246   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.392   0.708   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.892   1.054   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.994  -0.710   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.101  -0.131   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.154   1.500   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.640   1.096   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.976  -0.030   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.557   1.444   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.391   0.174   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.780   0.814   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.160   1.284   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.533   0.585   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       2.743   2.628   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29   34                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   14   26                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   17                                                       
CONECT   26    9   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26    7   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    2    5   32                                             
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    7                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃N₃O₄

Average Mass

463.5780 Da

Monoisotopic Mass

463.24711 Da

IUPAC Name

2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8,9-dihydro-7H-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-9-one

Traditional Name

2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8H-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-9-one

CAS Registry Number

Not Available

SMILES

CC1CCN2CC34CC5(C(O)=NC6=C5C=CC5=C6C(=O)CC(C)(C)O5)C(C)(C)C3CC12C(O)=N4

InChI Identifier

InChI=1S/C27H33N3O4/c1-14-8-9-30-13-25-12-26(24(4,5)18(25)11-27(14,30)22(33)29-25)15-6-7-17-19(20(15)28-21(26)32)16(31)10-23(2,3)34-17/h6-7,14,18H,8-13H2,1-5H3,(H,28,32)(H,29,33)

InChI Key

QHKDAOMEFDLNBK-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 herquei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Chromone
3-alkylindole
Indolizidine
Indole or derivatives
Aryl alkyl ketone
Aryl ketone
Aralkylamine
Tetrahydropyridine
Alkyl aryl ether
Benzenoid
N-alkylpyrrolidine
Piperidine
Cyclic carboximidic acid
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Ketone
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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	0.9	ChemAxon
pKa (Strongest Acidic)	2.04	ChemAxon
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.72 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	129.01 m³·mol⁻¹	ChemAxon
Polarizability	51.33 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

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

162816139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one (NP0205672)

MOL for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

3D MOL for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

3D SDF for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

3D-SDF for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

PDB for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

3D PDB for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

SMILES for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

INCHI for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

Structure for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)

3D Structure for NP0205672 (2,13'-dihydroxy-4',4',7,7,12'-pentamethyl-8h-9',14'-diazaspiro[pyrano[2,3-g]indole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-9-one)