NP-MRD: Showing NP-Card for (2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione (NP0295913)

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Record Information

Version

1.0

Created at

2022-09-10 05:11:22 UTC

Updated at

2022-09-10 05:11:22 UTC

NP-MRD ID

NP0295913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione

Description

Hapalosin belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group. It was first documented in 2004 (PMID: 15176838). Based on a literature review a significant number of articles have been published on Hapalosin (PMID: 22470225) (PMID: 26335778) (PMID: 33919559) (PMID: 33599093) (PMID: 29940102) (PMID: 27973631).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102207112D          

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 17 18  2  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  2  0  0  0  0
 17 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0295913

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC[C@H]1OC(=O)C[C@@H](O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@@H](OC(=O)[C@H]1C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H43NO6/c1-6-7-8-9-13-16-24-20(4)28(33)35-26(19(2)3)27(32)29(5)22(23(30)18-25(31)34-24)17-21-14-11-10-12-15-21/h10-12,14-15,19-20,22-24,26,30H,6-9,13,16-18H2,1-5H3/t20-,22-,23+,24+,26-/m0/s1

> <INCHI_KEY>
NJNAHFYVTBZQHU-LFFUDGMSSA-N

> <FORMULA>
C28H43NO6

> <MOLECULAR_WEIGHT>
489.653

> <EXACT_MASS>
489.309038109

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.52480346446954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,6R,10R,11S)-5-benzyl-10-heptyl-6-hydroxy-4,11-dimethyl-2-(propan-2-yl)-1,9-dioxa-4-azacyclododecane-3,8,12-trione

> <JCHEM_LOGP>
5.4439259643333315

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.380954585310928

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.301079167132535

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1045062765841926

> <JCHEM_POLAR_SURFACE_AREA>
93.14000000000001

> <JCHEM_REFRACTIVITY>
133.8185

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,6R,10R,11S)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.000  13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       2.667   9.240   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.240   8.946   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   15   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    8   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₃NO₆

Average Mass

489.6530 Da

Monoisotopic Mass

489.30904 Da

IUPAC Name

(2S,5S,6R,10R,11S)-5-benzyl-10-heptyl-6-hydroxy-4,11-dimethyl-2-(propan-2-yl)-1,9-dioxa-4-azacyclododecane-3,8,12-trione

Traditional Name

(2S,5S,6R,10R,11S)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione

CAS Registry Number

Not Available

SMILES

CCCCCCC[C@H]1OC(=O)C[C@@H](O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@@H](OC(=O)[C@H]1C)C(C)C

InChI Identifier

InChI=1S/C28H43NO6/c1-6-7-8-9-13-16-24-20(4)28(33)35-26(19(2)3)27(32)29(5)22(23(30)18-25(31)34-24)17-21-14-11-10-12-15-21/h10-12,14-15,19-20,22-24,26,30H,6-9,13,16-18H2,1-5H3/t20-,22-,23+,24+,26-/m0/s1

InChI Key

NJNAHFYVTBZQHU-LFFUDGMSSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolide lactams

Sub Class

Not Available

Direct Parent

Macrolide lactams

Alternative Parents

Substituents

Macrolide lactam
Macrolide
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	5.44	ChemAxon
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.14 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.82 m³·mol⁻¹	ChemAxon
Polarizability	55.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

117421

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133055

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim H, Krunic A, Lantvit D, Shen Q, Kroll DJ, Swanson SM, Orjala J: Nitrile-Containing Fischerindoles from the Cultured Cyanobacterium Fischerella sp. Tetrahedron. 2012 Apr 15;68(15):3205-3209. doi: 10.1016/j.tet.2012.02.048. [PubMed:22470225 ]
Micallef ML, D'Agostino PM, Sharma D, Viswanathan R, Moffitt MC: Genome mining for natural product biosynthetic gene clusters in the Subsection V cyanobacteria. BMC Genomics. 2015 Sep 3;16(1):669. doi: 10.1186/s12864-015-1855-z. [PubMed:26335778 ]
Jin X, Miller ES, Lindsey JS: Natural Product Gene Clusters in the Filamentous Nostocales Cyanobacterium HT-58-2. Life (Basel). 2021 Apr 18;11(4):356. doi: 10.3390/life11040356. [PubMed:33919559 ]
Figueiredo SAC, Preto M, Moreira G, Martins TP, Abt K, Melo A, Vasconcelos VM, Leao PN: Discovery of Cyanobacterial Natural Products Containing Fatty Acid Residues*. Angew Chem Int Ed Engl. 2021 Apr 26;60(18):10064-10072. doi: 10.1002/anie.202015105. Epub 2021 Mar 22. [PubMed:33599093 ]
D'Agostino PM, Gulder TAM: Direct Pathway Cloning Combined with Sequence- and Ligation-Independent Cloning for Fast Biosynthetic Gene Cluster Refactoring and Heterologous Expression. ACS Synth Biol. 2018 Jul 20;7(7):1702-1708. doi: 10.1021/acssynbio.8b00151. Epub 2018 Jul 3. [PubMed:29940102 ]
Si CM, Shao LP, Mao ZY, Zhou W, Wei BG: An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (-)-hapalosin. Org Biomol Chem. 2017 Jan 18;15(3):649-661. doi: 10.1039/c6ob02523d. [PubMed:27973631 ]
Dai CF, Cheng F, Xu HC, Ruan YP, Huang PQ: Diversity-oriented asymmetric synthesis of hapalosin: construction of three small C9/C4/C3-modified hapalosin analogue libraries. J Comb Chem. 2007 May-Jun;9(3):386-94. doi: 10.1021/cc060166h. Epub 2007 Mar 15. [PubMed:17358084 ]
Agoston K, Geyer A: Regioselective conversion of the secondary hydroxyl groups of D-glucuronic acid without the requirement of O-protecting groups. Chemistry. 2005 Oct 21;11(21):6407-13. doi: 10.1002/chem.200500515. [PubMed:16094680 ]
Palomo C, Oiarbide M, Garcia JM, Gonzalez A, Pazos R, Odriozola JM, Banuelos P, Tello M, Linden A: A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization. J Org Chem. 2004 Jun 11;69(12):4126-34. doi: 10.1021/jo0497499. [PubMed:15176838 ]
LOTUS database [Link]

Showing NP-Card for (2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione (NP0295913)

MOL for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

3D MOL for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

3D SDF for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

3D-SDF for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

PDB for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

3D PDB for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

SMILES for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

INCHI for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

Structure for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)

3D Structure for NP0295913 ((2s,5s,6r,10r,11s)-5-benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-azacyclododecane-3,8,12-trione)