NP-MRD: Showing NP-Card for 2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol (NP0242964)

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Record Information

Version

2.0

Created at

2022-09-07 03:25:01 UTC

Updated at

2022-09-07 03:25:01 UTC

NP-MRD ID

NP0242964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol

Description

2-(7,7,10B-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-1H,2H,3H,4aH,5H,7H,8H,9H,10H,10aH,10bH-naphtho[2,1-b]pyran-3-yl)propan-2-ol belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol is found in Aspergillus purpureus. 2-(7,7,10B-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-1H,2H,3H,4aH,5H,7H,8H,9H,10H,10aH,10bH-naphtho[2,1-b]pyran-3-yl)propan-2-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121512212D          

 36 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 04121512212D          

 36 40  0  0  0  0            999 V2000
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    4.0334    0.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479    1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    0.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479   -0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334    0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9938    1.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7785    2.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2092    1.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389    2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9319    2.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529   -1.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2096   -0.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9463   -0.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5610   -3.8719    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
  2  4  1  0  0  0  0
  2  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
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  2  0  0  0  0
 17 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 10 36  1  0  0  0  0
  5 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CCC2(C)C(CC=C3C2CCC(CC2=CN(C4=CC=CC=C24)C(C)(C)C=C)C3(C)C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C33H47NO2/c1-9-30(2,3)34-21-22(24-12-10-11-13-27(24)34)20-23-14-15-26-25(31(23,4)5)16-17-29-33(26,8)19-18-28(36-29)32(6,7)35/h9-13,16,21,23,26,28-29,35H,1,14-15,17-20H2,2-8H3

> <INCHI_KEY>
BDIIYBDSOVLLMV-UHFFFAOYSA-N

> <FORMULA>
C33H47NO2

> <MOLECULAR_WEIGHT>
489.744

> <EXACT_MASS>
489.360679757

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.1832878462216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-1H,2H,3H,4aH,5H,7H,8H,9H,10H,10aH,10bH-naphtho[2,1-b]pyran-3-yl)propan-2-ol

> <ALOGPS_LOGP>
8.05

> <JCHEM_LOGP>
7.5018138400000005

> <ALOGPS_LOGS>
-5.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.32609522539514

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0935659484121647

> <JCHEM_POLAR_SURFACE_AREA>
34.39

> <JCHEM_REFRACTIVITY>
150.60350000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.05e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1H,2H,3H,4aH,5H,8H,9H,10H,10aH-naphtho[2,1-b]pyran-3-yl)propan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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      13.832 -10.981   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.802  -9.837   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.946  -8.806   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.657 -10.867   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.771  -8.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.265  -9.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.234  -7.868   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.710  -6.403   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.204  -6.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.217  -6.083   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.693  -4.618   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.662  -3.474   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.156  -3.794   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.680  -5.259   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.174  -5.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.143  -4.435   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.619  -2.970   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.589  -1.826   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.064  -0.361   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.159   0.885   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.064   2.131   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       7.529   1.655   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.863   2.425   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.196   1.655   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.196   0.115   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.863  -0.655   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.529   0.115   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.589   3.596   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.053   4.071   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.124   3.120   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.113   5.060   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.606   5.380   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.125  -2.650   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.858  -1.133   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.233  -1.580   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.247  -7.228   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11   36                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   22                                                  
CONECT   28   21   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32                                                       
CONECT   32   31                                                            
CONECT   33   17   13   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   10    5                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₇NO₂

Average Mass

489.7440 Da

Monoisotopic Mass

489.36068 Da

IUPAC Name

2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-1H,2H,3H,4aH,5H,7H,8H,9H,10H,10aH,10bH-naphtho[2,1-b]pyran-3-yl)propan-2-ol

Traditional Name

2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1H,2H,3H,4aH,5H,8H,9H,10H,10aH-naphtho[2,1-b]pyran-3-yl)propan-2-ol

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CCC2(C)C(CC=C3C2CCC(CC2=CN(C4=CC=CC=C24)C(C)(C)C=C)C3(C)C)O1

InChI Identifier

InChI=1S/C33H47NO2/c1-9-30(2,3)34-21-22(24-12-10-11-13-27(24)34)20-23-14-15-26-25(31(23,4)5)16-17-29-33(26,8)19-18-28(36-29)32(6,7)35/h9-13,16,21,23,26,28-29,35H,1,14-15,17-20H2,2-8H3

InChI Key

BDIIYBDSOVLLMV-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
Emericella purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
N-alkylindole
3-alkylindole
Indole
Indole or derivatives
Oxane
Pyran
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary alcohol
Oxacycle
Ether
Azacycle
Dialkyl ether
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	8.05	ALOGPS
logP	7.5	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	14.33	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	34.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	150.6 m³·mol⁻¹	ChemAxon
Polarizability	59.18 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

73024504

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol (NP0242964)

MOL for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

3D MOL for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

3D SDF for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

3D-SDF for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

PDB for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

3D PDB for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

SMILES for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

INCHI for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

Structure for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)

3D Structure for NP0242964 (2-(7,7,10b-trimethyl-8-{[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl)propan-2-ol)