NP-MRD: Showing NP-Card for (1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0161912)

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Record Information

Version

2.0

Created at

2022-09-02 20:13:04 UTC

Updated at

2022-09-02 20:13:04 UTC

NP-MRD ID

NP0161912

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

Description

Puberuline, also known as fructigenine a or rugulosuvine b, belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one is found in Agathosma martiana and Penicillium aurantiogriseum. (1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one was first documented in 2007 (PMID: 18095438). Based on a literature review very few articles have been published on Puberuline (PMID: 30155084).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022222132D          

 33 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022222132D          

 33 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0161912

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N1[C@H]2N3[C@@H](C[C@]2(C2=CC=CC=C12)C(C)(C)C=C)C(O)=N[C@@H](CC1=CC=CC=C1)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H29N3O3/c1-5-26(3,4)27-16-22-23(32)28-20(15-18-11-7-6-8-12-18)24(33)30(22)25(27)29(17(2)31)21-14-10-9-13-19(21)27/h5-14,20,22,25H,1,15-16H2,2-4H3,(H,28,32)/t20-,22-,25-,27+/m0/s1

> <INCHI_KEY>
UHFSGFDEMVYYRX-YSDDDFLKSA-N

> <FORMULA>
C27H29N3O3

> <MOLECULAR_WEIGHT>
443.547

> <EXACT_MASS>
443.220891806

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
48.14896309231585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,7S,9R)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.9806808496666664

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.22064246413272

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.572013872013839

> <JCHEM_PKA_STRONGEST_BASIC>
1.2404974004158347

> <JCHEM_POLAR_SURFACE_AREA>
73.21000000000001

> <JCHEM_REFRACTIVITY>
125.40660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,7S,9R)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.473   4.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.007   4.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.662   2.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.268   2.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.056   3.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.440   2.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.533   3.795   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       9.409   1.275   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.284  -1.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.738  -0.739   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.028   0.773   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.483   1.279   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.648   0.271   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.358  -1.241   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.903  -1.746   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.374  -2.255   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       6.499   0.265   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       3.848  -0.980   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       4.039  -2.508   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.812  -3.438   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.458  -3.106   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.121   0.265   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.788   1.275   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   23   33                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   12   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    8   23                                                  
CONECT   23   22    6   24                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28    6                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Fructigenine a	MeSH
Rugulosuvine b	MeSH

Chemical Formula

C₂₇H₂₉N₃O₃

Average Mass

443.5470 Da

Monoisotopic Mass

443.22089 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)N1[C@H]2N3[C@@H](C[C@]2(C2=CC=CC=C12)C(C)(C)C=C)C(O)=N[C@@H](CC1=CC=CC=C1)C3=O

InChI Identifier

InChI=1S/C27H29N3O3/c1-5-26(3,4)27-16-22-23(32)28-20(15-18-11-7-6-8-12-18)24(33)30(22)25(27)29(17(2)31)21-14-10-9-13-19(21)27/h5-14,20,22,25H,1,15-16H2,2-4H3,(H,28,32)/t20-,22-,25-,27+/m0/s1

InChI Key

UHFSGFDEMVYYRX-YSDDDFLKSA-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
Agathosma martiana	LOTUS Database	35616633
Penicillium aurantiogriseum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting 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

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Benzenoid
Acetamide
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
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

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

2340622

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3083399

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nunez F, Westphal CD, Bermudez E, Asensio MA: Production of secondary metabolites by some terverticillate penicillia on carbohydrate-rich and meat substrates. J Food Prot. 2007 Dec;70(12):2829-36. doi: 10.4315/0362-028x-70.12.2829. [PubMed:18095438 ]
Hagiwara K, Tabuchi T, Urabe D, Inoue M: Expeditious synthesis of the fused hexacycle of puberuline C via a radical-based cyclization/translocation/cyclization process. Chem Sci. 2016 Jul 1;7(7):4372-4378. doi: 10.1039/c6sc00671j. Epub 2016 Mar 18. [PubMed:30155084 ]
LOTUS database [Link]

Showing NP-Card for (1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0161912)

MOL for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D MOL for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D SDF for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D-SDF for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

PDB for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D PDB for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

SMILES for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

INCHI for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

Structure for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D Structure for NP0161912 ((1r,4s,7s,9r)-16-acetyl-4-benzyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)