NP-MRD: Showing NP-Card for (1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one (NP0227599)

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Record Information

Version

2.0

Created at

2022-09-06 06:58:28 UTC

Updated at

2022-09-06 06:58:28 UTC

NP-MRD ID

NP0227599

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one

Description

Cespitulactam J belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. (1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one is found in Conglomeratusclera coerulea. Based on a literature review very few articles have been published on cespitulactam J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062208582D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062208582D          

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 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 21 29  1  0  0  0  0
 24 29  1  0  0  0  0
 18 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  2  0  0  0  0
  9 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/[C@@H](O)CC(=C)CC[C@@H]2CCC3=C([C@@H](C1)N(CCC1=CNC4=CC=CC=C14)C3=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H38N2O2/c1-19-9-10-22-11-12-25-28(30(22,3)4)27(17-20(2)16-23(33)15-19)32(29(25)34)14-13-21-18-31-26-8-6-5-7-24(21)26/h5-8,16,18,22-23,27,31,33H,1,9-15,17H2,2-4H3/b20-16+/t22-,23+,27-/m1/s1

> <INCHI_KEY>
ABTDHHPHHKFQBT-USINTNLNSA-N

> <FORMULA>
C30H38N2O2

> <MOLECULAR_WEIGHT>
458.646

> <EXACT_MASS>
458.293328472

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.83296105653467

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3E,5S,10R)-5-hydroxy-15-[2-(1H-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0^{13,16}]heptadeca-3,13(16)-dien-14-one

> <JCHEM_LOGP>
5.1363192086666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.159321765160264

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.000491436631698

> <JCHEM_PKA_STRONGEST_BASIC>
0.4375926099274386

> <JCHEM_POLAR_SURFACE_AREA>
56.33

> <JCHEM_REFRACTIVITY>
139.54500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3E,5S,10R)-5-hydroxy-15-[2-(1H-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0^{13,16}]heptadeca-3,13(16)-dien-14-one

> <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      11.732   1.812   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.280   2.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.561   0.812   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.390  -0.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.938   0.326   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.695  -0.583   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.286   0.039   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.120   1.570   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.206   2.354   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.925   3.868   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.096   4.869   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.548   4.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.828   2.840   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.719   5.355   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.170   4.841   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.341   5.841   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.451   3.326   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.343   3.937   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.463   5.201   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.929   5.071   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.049   6.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.555   7.790   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       0.327   8.720   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -0.937   7.841   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.436   8.191   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.490   7.068   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.044   5.594   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.544   5.243   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.491   6.367   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.872   2.471   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.409   1.991   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.657   1.840   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.222   3.273   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.161   2.173   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   32                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2                                                       
CONECT   18   10   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   21   24                                                  
CONECT   30   18    8   31                                                  
CONECT   31   30                                                            
CONECT   32    9    5   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈N₂O₂

Average Mass

458.6460 Da

Monoisotopic Mass

458.29333 Da

IUPAC Name

(1R,3E,5S,10R)-5-hydroxy-15-[2-(1H-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0^{13,16}]heptadeca-3,13(16)-dien-14-one

Traditional Name

(1R,3E,5S,10R)-5-hydroxy-15-[2-(1H-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0^{13,16}]heptadeca-3,13(16)-dien-14-one

CAS Registry Number

Not Available

SMILES

C\C1=C/[C@@H](O)CC(=C)CC[C@@H]2CCC3=C([C@@H](C1)N(CCC1=CNC4=CC=CC=C14)C3=O)C2(C)C

InChI Identifier

InChI=1S/C30H38N2O2/c1-19-9-10-22-11-12-25-28(30(22,3)4)27(17-20(2)16-23(33)15-19)32(29(25)34)14-13-21-18-31-26-8-6-5-7-24(21)26/h5-8,16,18,22-23,27,31,33H,1,9-15,17H2,2-4H3/b20-16+/t22-,23+,27-/m1/s1

InChI Key

ABTDHHPHHKFQBT-USINTNLNSA-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
Conglomeratusclera coerulea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Isoindolone
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrole
Pyrroline
Carboxamide group
Lactam
Secondary alcohol
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Alcohol
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
logP	5.14	ChemAxon
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	0.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	139.54 m³·mol⁻¹	ChemAxon
Polarizability	51.83 Å³	ChemAxon
Number of Rings	5	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

23311119

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24762991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one (NP0227599)

MOL for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

3D MOL for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

3D SDF for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

3D-SDF for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

PDB for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

3D PDB for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

SMILES for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

INCHI for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

Structure for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)

3D Structure for NP0227599 ((1r,3e,5s,10r)-5-hydroxy-15-[2-(1h-indol-3-yl)ethyl]-3,17,17-trimethyl-7-methylidene-15-azatricyclo[8.5.2.0¹³,¹⁶]heptadeca-3,13(16)-dien-14-one)