NP-MRD: Showing NP-Card for 2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one (NP0307192)

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Record Information

Version

2.0

Created at

2022-09-11 00:09:15 UTC

Updated at

2022-09-11 00:09:15 UTC

NP-MRD ID

NP0307192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one

Description

2-Hydroxy-9a-methoxy-3,4a,5-trimethyl-4H,4aH,5H,6H,8aH,9H,9aH-cyclohexa[f]indol-6-one belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. 2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one is found in Senecio flavus. 2-Hydroxy-9a-methoxy-3,4a,5-trimethyl-4H,4aH,5H,6H,8aH,9H,9aH-cyclohexa[f]indol-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.8304   -1.4406    1.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138   -0.3452    1.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -0.3506    0.1894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8166   -1.4906   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317   -1.2509    0.1582 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4822   -2.2322   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877   -2.1237   -0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2903   -1.0596    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3029   -1.2554    1.1341 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5720    0.2361    0.3753 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6133    0.9169    1.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1561    0.1048   -0.1187 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1711    0.4268   -1.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2540    1.1441    0.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850    0.9552   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8402    1.6590   -0.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    3.0203   -1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270    0.9101   -1.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9721    1.2591   -1.9871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9288   -0.3338   -0.5928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592   -2.4107    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1732   -1.3455    2.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8158   -1.4764    1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950   -1.6674   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421   -2.4222    0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320   -1.4714    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0774   -3.0054   -1.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -2.7992   -0.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658    0.8972   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6365    0.7890    2.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    1.9924    1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163    0.4869    2.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302    1.5333   -1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552    0.0869   -2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -0.0345   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0948    0.9128    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299    2.1522    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    3.6956   -1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5725    3.3918   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202    3.0892   -2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204   -1.1443   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 15  3  1  0
 20  3  1  0
 12  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  7 28  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 20 41  1  0
M  END


  Mrv1533004171517562D          

 20 22  0  0  0  0            999 V2000
    3.2190   -0.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516   -0.7025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 N   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 12  1  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
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC12CC3C=CC(=O)C(C)C3(C)CC1=C(C)C(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO3/c1-9-12-8-15(3)10(2)13(18)6-5-11(15)7-16(12,20-4)17-14(9)19/h5-6,10-11H,7-8H2,1-4H3,(H,17,19)

> <INCHI_KEY>
WVEFQNOWFOGYOJ-UHFFFAOYSA-N

> <FORMULA>
C16H21NO3

> <MOLECULAR_WEIGHT>
275.348

> <EXACT_MASS>
275.15214354

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.49760927182669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9a-methoxy-3,4a,5-trimethyl-1H,2H,4H,4aH,5H,6H,8aH,9H,9aH-cyclohexa[f]indole-2,6-dione

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
2.0188033730000012

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.845976484770148

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.873194346743785

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4282219981078438

> <JCHEM_POLAR_SURFACE_AREA>
55.400000000000006

> <JCHEM_REFRACTIVITY>
77.18809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9a-methoxy-3,4a,5-trimethyl-1H,4H,5H,8aH,9H-cyclohexa[f]indole-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.009  -0.406   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.763  -1.311   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.592  -5.153   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.983  -6.323   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.014  -3.613   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       3.459  -2.367   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15   20                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    3   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₁NO₃

Average Mass

275.3480 Da

Monoisotopic Mass

275.15214 Da

IUPAC Name

9a-methoxy-3,4a,5-trimethyl-1H,2H,4H,4aH,5H,6H,8aH,9H,9aH-cyclohexa[f]indole-2,6-dione

Traditional Name

9a-methoxy-3,4a,5-trimethyl-1H,4H,5H,8aH,9H-cyclohexa[f]indole-2,6-dione

CAS Registry Number

Not Available

SMILES

COC12CC3C=CC(=O)C(C)C3(C)CC1=C(C)C(=O)N2

InChI Identifier

InChI=1S/C16H21NO3/c1-9-12-8-15(3)10(2)13(18)6-5-11(15)7-16(12,20-4)17-14(9)19/h5-6,10-11H,7-8H2,1-4H3,(H,17,19)

InChI Key

WVEFQNOWFOGYOJ-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
Senecio flavus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Cyclohexenone
Pyrroline
Cyclic ketone
Secondary carboxylic acid amide
Lactam
Ketone
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
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	1.51	ALOGPS
logP	2.02	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
pKa (Strongest Basic)	-0.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.19 m³·mol⁻¹	ChemAxon
Polarizability	29.5 Å³	ChemAxon
Number of Rings	3	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 2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one (NP0307192)

MOL for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

3D MOL for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

3D SDF for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

3D-SDF for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

PDB for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

3D PDB for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

SMILES for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

INCHI for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

Structure for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)

3D Structure for NP0307192 (2-hydroxy-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-cyclohexa[f]indol-6-one)