NP-MRD: Showing NP-Card for (3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate (NP0225088)

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Record Information

Version

2.0

Created at

2022-09-06 03:42:11 UTC

Updated at

2022-09-06 03:42:11 UTC

NP-MRD ID

NP0225088

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate

Description

Torrubiellutin C 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. (3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate is found in Conoideocrella luteorostrata. (3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate was first documented in 2014 (PMID: 24445589). Based on a literature review very few articles have been published on Torrubiellutin C (PMID: 35909083).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062205422D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062205422D          

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 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0225088

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO6/c1-17-13-14-25(31)29(7)24(16-23-11-9-8-10-12-23)28(33)34-21(5)20(4)27(35-22(6)30)19(3)15-18(2)26(17)32/h8-15,17,19-21,24,26-27,32H,16H2,1-7H3/b14-13+,18-15-/t17-,19+,20+,21+,24+,26+,27-/m1/s1

> <INCHI_KEY>
AONWYFVWMXMNLE-ZWIHURBOSA-N

> <FORMULA>
C28H39NO6

> <MOLECULAR_WEIGHT>
485.621

> <EXACT_MASS>
485.27773798

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.61828960258092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6E,8R,9S,10Z,12S,13R,14S,15S)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate

> <JCHEM_LOGP>
3.8609245483333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.842221916758515

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.80958424254755

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2746838380374427

> <JCHEM_POLAR_SURFACE_AREA>
93.14000000000001

> <JCHEM_REFRACTIVITY>
135.89140000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6E,8R,9S,10Z,12S,13R,14S,15S)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.650  -3.167   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.333  -2.368   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.366  -0.828   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.017  -3.109   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.261  -0.626   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.686  -0.043   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.230   0.518   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.000   1.852   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.374   3.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.506   1.532   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.176   0.145   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.034   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       8.002  -0.000   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.295  -3.717   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   21   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    5   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
5-Epi-torrubiellutin C	MeSH

Chemical Formula

C₂₈H₃₉NO₆

Average Mass

485.6210 Da

Monoisotopic Mass

485.27774 Da

IUPAC Name

(3S,6E,8R,9S,10Z,12S,13R,14S,15S)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate

Traditional Name

(3S,6E,8R,9S,10Z,12S,13R,14S,15S)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H39NO6/c1-17-13-14-25(31)29(7)24(16-23-11-9-8-10-12-23)28(33)34-21(5)20(4)27(35-22(6)30)19(3)15-18(2)26(17)32/h8-15,17,19-21,24,26-27,32H,16H2,1-7H3/b14-13+,18-15-/t17-,19+,20+,21+,24+,26+,27-/m1/s1

InChI Key

AONWYFVWMXMNLE-ZWIHURBOSA-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
Conoideocrella luteorostrata	LOTUS Database	35616633

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
Alpha-amino acid ester
Macrolactam
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen 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	3.86	ChemAxon
pKa (Strongest Acidic)	18.81	ChemAxon
pKa (Strongest Basic)	-0.27	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	4	ChemAxon
Refractivity	135.89 m³·mol⁻¹	ChemAxon
Polarizability	53.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

44204105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Murokawa S, Furukawa K, Kawano Y, Nihei T, Suzuki Y, Yasui E, Nagumo S: Reductive S(N) 2' Reaction of Epoxydienoate with Borane and its Application to the Synthesis and Structural Revision of an Antitumor Active Torrubiellutin Analogue. Chem Asian J. 2022 Sep 14;17(18):e202200650. doi: 10.1002/asia.202200650. Epub 2022 Aug 18. [PubMed:35909083 ]
Singh A, Mahipal B, Chandrasekhar S, Ummanni R: 5-epi-Torrubiellutin C shows antiproliferative activity on DU145 prostate cancer cells through inactivation of the AKT/mTOR pathway. Anticancer Drugs. 2014 Apr;25(4):385-92. doi: 10.1097/CAD.0000000000000064. [PubMed:24445589 ]
LOTUS database [Link]

Showing NP-Card for (3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate (NP0225088)

MOL for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

3D MOL for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

3D SDF for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

3D-SDF for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

PDB for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

3D PDB for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

SMILES for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

INCHI for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

Structure for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)

3D Structure for NP0225088 ((3s,6e,8r,9s,10z,12s,13r,14s,15s)-3-benzyl-9-hydroxy-4,8,10,12,14,15-hexamethyl-2,5-dioxo-1-oxa-4-azacyclopentadeca-6,10-dien-13-yl acetate)