NP-MRD: Showing NP-Card for phomactinine (NP0331736)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2023-07-29 00:11:25 UTC

Updated at

2024-09-03 04:16:42 UTC

NP-MRD ID

NP0331736

Natural Product DOI

https://doi.org/10.57994/0767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

phomactinine

Description

Phomactinine belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. phomactinine was first documented in 2023 (PMID: 37490470). Based on a literature review very few articles have been published on phomactinine.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 07292300112D          

 24 27  0  0  1  0            999 V2000
    1.7028   -0.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767    0.0825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1897    0.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    1.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5775    1.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8059    0.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2463    1.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9123    1.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551    0.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9837   -0.3652    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7454   -0.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4968   -1.0312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3170   -1.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -0.7652    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2159   -0.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3694   -1.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628   -1.6994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5230   -2.3632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.9425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3432   -0.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5225   -0.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3486   -1.0782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618   -1.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -2.2992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 12 10  1  0  0  0  0
 12 13  1  6  0  0  0
 10 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  1  0  0  0
 19 17  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](O)[C@@]23[C@H]4O[C@]4(C)CC\C=C(C)\CC[C@@]1(C)C2=CNC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H29NO3/c1-12-6-5-8-19(4)16(24-19)20-14(11-21-17(20)23)18(3,9-7-12)13(2)10-15(20)22/h6,11,13,15-16,22H,5,7-10H2,1-4H3,(H,21,23)/b12-6+/t13-,15+,16+,18-,19-,20-/m1/s1

> <INCHI_KEY>
DDFPSYZDBGJXBB-FYVYODAKSA-N

> <FORMULA>
C20H29NO3

> <MOLECULAR_WEIGHT>
331.456

> <EXACT_MASS>
331.214743798

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.97114693259999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,7E,11R,16S,18R)-16-hydroxy-4,8,11,18-tetramethyl-3-oxa-14-azatetracyclo[9.4.3.0^{1,12}.0^{2,4}]octadeca-7,12-dien-15-one

> <JCHEM_LOGP>
2.065108540666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.553692546219326

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.093097144928919

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0929374710237996

> <JCHEM_POLAR_SURFACE_AREA>
61.86

> <JCHEM_REFRACTIVITY>
93.40359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,7E,11R,16S,18R)-16-hydroxy-4,8,11,18-tetramethyl-3-oxa-14-azatetracyclo[9.4.3.0^{1,12}.0^{2,4}]octadeca-7,12-dien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUL-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUL-23         0                                  
HETATM    1  C   UNK     0       3.178  -0.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.436   0.154   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.087   1.223   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.996   2.467   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.678   2.358   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.104   0.879   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.926   3.260   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.170   2.351   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.689   0.888   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.303  -0.682   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.725  -0.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.394  -1.925   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.925  -2.090   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.801  -1.428   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.270  -1.263   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.423  -2.837   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.091  -3.172   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.576  -4.411   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.863  -1.759   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.241  -0.351   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.709  -0.507   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       4.384  -2.013   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       5.715  -2.787   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.391  -4.292   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   10                                                       
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20   23                                             
CONECT   20   19    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₉NO₃

Average Mass

331.4560 Da

Monoisotopic Mass

331.21474 Da

IUPAC Name

(1R,2R,4R,7E,11R,16S,18R)-16-hydroxy-4,8,11,18-tetramethyl-3-oxa-14-azatetracyclo[9.4.3.0^{1,12}.0^{2,4}]octadeca-7,12-dien-15-one

Traditional Name

(1R,2R,4R,7E,11R,16S,18R)-16-hydroxy-4,8,11,18-tetramethyl-3-oxa-14-azatetracyclo[9.4.3.0^{1,12}.0^{2,4}]octadeca-7,12-dien-15-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](O)[C@@]23[C@H]4O[C@]4(C)CC\C=C(C)\CC[C@@]1(C)C2=CNC3=O

InChI Identifier

InChI=1S/C20H29NO3/c1-12-6-5-8-19(4)16(24-19)20-14(11-21-17(20)23)18(3,9-7-12)13(2)10-15(20)22/h6,11,13,15-16,22H,5,7-10H2,1-4H3,(H,21,23)/b12-6+/t13-,15+,16+,18-,19-,20-/m1/s1

InChI Key

DDFPSYZDBGJXBB-FYVYODAKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	rgsberlinck@iqsc.usp.br	Not Available	Not Available	2023-07-29	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Isoindolone
Isoindole or derivatives
Fatty acyl
N-acyl-amine
Fatty amide
Pyrroline
Cyclic alcohol
Secondary alcohol
Lactam
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
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	2.07	ChemAxon
pKa (Strongest Acidic)	13.09	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.86 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.4 m³·mol⁻¹	ChemAxon
Polarizability	35.97 Å³	ChemAxon
Number of Rings	4	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

da Silva Oliveira L, Crnkovic CM, de Amorim MR, Navarro-Vazquez A, Paz TA, Freire VF, Takaki M, Venancio T, Ferreira AG, de Freitas Saito R, Chammas R, Berlinck RGS: Phomactinine, the First Nitrogen-Bearing Phomactin, Produced by Biatriospora sp. CBMAI 1333. J Nat Prod. 2023 Aug 25;86(8):2065-2072. doi: 10.1021/acs.jnatprod.3c00383. Epub 2023 Jul 25. [PubMed:37490470 ]

Showing NP-Card for phomactinine (NP0331736)

MOL for NP0331736 (phomactinine)

3D MOL for NP0331736 (phomactinine)

3D SDF for NP0331736 (phomactinine)

3D-SDF for NP0331736 (phomactinine)

PDB for NP0331736 (phomactinine)

3D PDB for NP0331736 (phomactinine)

SMILES for NP0331736 (phomactinine)

INCHI for NP0331736 (phomactinine)

Structure for NP0331736 (phomactinine)

3D Structure for NP0331736 (phomactinine)