NP-MRD: Showing NP-Card for 4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol (NP0239441)

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Record Information

Version

2.0

Created at

2022-09-06 23:02:40 UTC

Updated at

2022-09-06 23:02:40 UTC

NP-MRD ID

NP0239441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol

Description

4-[3,4A,6-trimethyl-2-(4-methylhex-2-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]-2H-pyrrole-2,5-diol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol is found in Talaromyces convolutus. 4-[3,4A,6-trimethyl-2-(4-methylhex-2-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]-2H-pyrrole-2,5-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201503092D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004201503092D          

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    4.0303    2.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766    3.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    3.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8579    4.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7716    5.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6115    4.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978    3.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366    2.2295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    2.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166    2.6100    0.0000 O   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
  5  3  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  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
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0239441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C=C(C)C1C(C2CCC(C)CC2(C)C=C1C)C(=O)C1=CC(O)(CC2=CC=C(O)C=C2)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H43NO4/c1-7-19(2)14-21(4)27-22(5)16-31(6)15-20(3)8-13-26(31)28(27)29(35)25-18-32(37,33-30(25)36)17-23-9-11-24(34)12-10-23/h9-12,14,16,18-20,26-28,34,37H,7-8,13,15,17H2,1-6H3,(H,33,36)

> <INCHI_KEY>
DZMMOKIPXHQOJN-UHFFFAOYSA-N

> <FORMULA>
C32H43NO4

> <MOLECULAR_WEIGHT>
505.699

> <EXACT_MASS>
505.319208869

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.68126251573693

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-5-hydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydro-1H-pyrrol-2-one

> <ALOGPS_LOGP>
5.32

> <JCHEM_LOGP>
6.657150961999999

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.968337385366368

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.47837292155386

> <JCHEM_PKA_STRONGEST_BASIC>
-1.48791634087425

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
150.44030000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.26e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1H-naphthalene-1-carbonyl]-5-hydroxy-5-[(4-hydroxyphenyl)methyl]-1H-pyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.408   1.684   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.438   2.828   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.469   1.684   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.684   3.733   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.523   5.265   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.116   5.891   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.955   7.423   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.201   8.328   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.040   9.860   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.608   7.702   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.769   6.170   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       5.668   4.162   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       4.162   3.842   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.018   4.872   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    8   20                                                  
CONECT   20   19                                                            
CONECT   21    9   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   36                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   35                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28                                                       
CONECT   35   25   36                                                       
CONECT   36   35   23   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₃NO₄

Average Mass

505.6990 Da

Monoisotopic Mass

505.31921 Da

IUPAC Name

3-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-5-hydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydro-1H-pyrrol-2-one

Traditional Name

3-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1H-naphthalene-1-carbonyl]-5-hydroxy-5-[(4-hydroxyphenyl)methyl]-1H-pyrrol-2-one

CAS Registry Number

Not Available

SMILES

CCC(C)C=C(C)C1C(C2CCC(C)CC2(C)C=C1C)C(=O)C1=CC(O)(CC2=CC=C(O)C=C2)NC1=O

InChI Identifier

InChI=1S/C32H43NO4/c1-7-19(2)14-21(4)27-22(5)16-31(6)15-20(3)8-13-26(31)28(27)29(35)25-18-32(37,33-30(25)36)17-23-9-11-24(34)12-10-23/h9-12,14,16,18-20,26-28,34,37H,7-8,13,15,17H2,1-6H3,(H,33,36)

InChI Key

DZMMOKIPXHQOJN-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
Talaromyces convolutus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Cyclic carboximidic acid
Ketone
Alkanolamine
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
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	5.32	ALOGPS
logP	6.66	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	150.44 m³·mol⁻¹	ChemAxon
Polarizability	58.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

72615835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol (NP0239441)

MOL for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

3D MOL for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

3D SDF for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

3D-SDF for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

PDB for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

3D PDB for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

SMILES for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

INCHI for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

Structure for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)

3D Structure for NP0239441 (4-[3,4a,6-trimethyl-2-(4-methylhex-2-en-2-yl)-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-2-[(4-hydroxyphenyl)methyl]pyrrole-2,5-diol)