NP-MRD: Showing NP-Card for (1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol (NP0325259)

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Record Information

Version

2.0

Created at

2022-09-12 05:52:25 UTC

Updated at

2022-09-12 05:52:25 UTC

NP-MRD ID

NP0325259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol

Description

Nominine belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. (1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol is found in Aconitum seravschanicum and Aspergillus alliaceus. (1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol was first documented in 2003 (PMID: 12556185). Based on a literature review a significant number of articles have been published on Nominine (PMID: 32888673) (PMID: 18046691) (PMID: 18027969) (PMID: 16819859) (PMID: 15352194).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207522D          

 30 33  0  0  1  0            999 V2000
    2.6043   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3493    0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5423    0.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874    1.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394    1.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0325    1.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5845    2.6010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7775    2.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365    3.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435    3.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1984    2.2579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9521    2.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464    1.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534    1.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0054    2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8124    1.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0673    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743    0.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153    0.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9013    0.8602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7083    0.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633   -0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633   -1.4308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479   -1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -1.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1768   -0.3509    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
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  4  5  1  0  0  0  0
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  5 13  1  0  0  0  0
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 25 30  1  0  0  0  0
M  END

     RDKit          3D

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    3.7987    2.7871    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122207522D          

 30 33  0  0  1  0            999 V2000
    2.6043   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0325259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H](O)C2(CCC=C(C)C)[C@H](CC3=CNC4=CC=CC=C34)C(=C)CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO/c1-19(2)9-8-15-28-24(17-22-18-29-25-11-7-6-10-23(22)25)20(3)14-16-27(28,5)21(4)12-13-26(28)30/h6-7,9-11,18,21,24,26,29-30H,3,8,12-17H2,1-2,4-5H3/t21-,24-,26+,27?,28?/m1/s1

> <INCHI_KEY>
BSSPRCKKWJRAJZ-JFRAZZIDSA-N

> <FORMULA>
C28H39NO

> <MOLECULAR_WEIGHT>
405.626

> <EXACT_MASS>
405.30316488

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.357636180973806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,8R)-8-[(1H-indol-3-yl)methyl]-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-ol

> <JCHEM_LOGP>
6.886405166666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.23708341949329

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.665249563537685

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9447068173912214

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
127.5771

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,8R)-8-(1H-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1H-naphthalen-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.861  -1.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.385   0.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.879   0.781   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.403   2.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.434   3.391   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.927   3.711   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.958   4.855   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.451   5.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.988   6.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.495   5.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.970   4.215   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.377   4.841   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.940   3.070   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.446   2.750   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.477   3.895   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.983   3.574   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.459   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.965   1.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.429   0.965   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.416   1.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.922   1.286   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.398  -0.179   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.493  -1.425   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       7.398  -2.671   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       8.863  -2.195   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.196  -2.965   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.530  -2.195   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.530  -0.655   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.196   0.115   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.863  -0.655   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14   20                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   13    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   22   25                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO

Average Mass

405.6260 Da

Monoisotopic Mass

405.30316 Da

IUPAC Name

(1S,4R,8R)-8-[(1H-indol-3-yl)methyl]-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-ol

Traditional Name

(1S,4R,8R)-8-(1H-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1H-naphthalen-1-ol

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H](O)C2(CCC=C(C)C)[C@H](CC3=CNC4=CC=CC=C34)C(=C)CCC12C

InChI Identifier

InChI=1S/C28H39NO/c1-19(2)9-8-15-28-24(17-22-18-29-25-11-7-6-10-23(22)25)20(3)14-16-27(28,5)21(4)12-13-26(28)30/h6-7,9-11,18,21,24,26,29-30H,3,8,12-17H2,1-2,4-5H3/t21-,24-,26+,27?,28?/m1/s1

InChI Key

BSSPRCKKWJRAJZ-JFRAZZIDSA-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
Aconitum zeravschanicum	LOTUS Database	35616633
Aspergillus alliaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Cyclic alcohol
Secondary alcohol
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
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	6.89	ChemAxon
pKa (Strongest Acidic)	14.67	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.02 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.58 m³·mol⁻¹	ChemAxon
Polarizability	49.36 Å³	ChemAxon
Number of Rings	4	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

C00024936

Chemspider ID

10143267

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11969862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang S, Zhang JF, Chen L, Gao F, Zhou XL: Diterpenoid alkaloids from Aconitum anthoroideum that offer protection against MPP(+)-Induced apoptosis of SH-SY5Y cells and acetylcholinesterase inhibitory activity. Phytochemistry. 2020 Oct;178:112459. doi: 10.1016/j.phytochem.2020.112459. Epub 2020 Jul 23. [PubMed:32888673 ]
Peese KM, Gin DY: Asymmetric synthetic access to the hetisine alkaloids: total synthesis of (+)-nominine. Chemistry. 2008;14(5):1654-65. doi: 10.1002/chem.200701290. [PubMed:18046691 ]
Hutt OE, Mander LN: Studies toward the total synthesis of nominine. J Org Chem. 2007 Dec 21;72(26):10130-40. doi: 10.1021/jo701995u. Epub 2007 Nov 21. [PubMed:18027969 ]
Peese KM, Gin DY: Efficient synthetic access to the hetisine C20-diterpenoid alkaloids. A concise synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions. J Am Chem Soc. 2006 Jul 12;128(27):8734-5. doi: 10.1021/ja0625430. [PubMed:16819859 ]
Muratake H, Natsume M: Total synthesis of (+/-)-nominine, a heptacyclic hetisine-type aconite alkaloid. Angew Chem Int Ed Engl. 2004 Sep 6;43(35):4646-9. doi: 10.1002/anie.200460332. [PubMed:15352194 ]
Liu Y, McWhorter WW Jr, Hadden CE: Novel rearrangement of a 2-aryl-3-alkyl-3H-indol-3-ol to a 1,4,5,6-tetrahydro-2,6-methano-1-benzazocin-3(2H)-one with implications for the biosynthesis of aspernomine. Org Lett. 2003 Feb 6;5(3):333-5. doi: 10.1021/ol0202417. [PubMed:12556185 ]
LOTUS database [Link]

Showing NP-Card for (1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol (NP0325259)

MOL for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

3D MOL for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

3D SDF for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

3D-SDF for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

PDB for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

3D PDB for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

SMILES for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

INCHI for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

Structure for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)

3D Structure for NP0325259 ((1s,4r,8r)-8-(1h-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-ol)