NP-MRD: Showing NP-Card for 4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione (NP0279777)

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Record Information

Version

2.0

Created at

2022-09-09 05:17:22 UTC

Updated at

2022-09-09 05:17:22 UTC

NP-MRD ID

NP0279777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione

Description

4-(Butan-2-yl)-4,9-dihydroxy-8-methyl-9-(propan-2-yl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]Nonadec-13-ene-3,6,10-trione belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione is found in Parsonsia alboflavescens. 4-(Butan-2-yl)-4,9-dihydroxy-8-methyl-9-(propan-2-yl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]Nonadec-13-ene-3,6,10-trione is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502122D          

 32 34  0  0  0  0            999 V2000
    6.9588    0.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380    1.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557    0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8349    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9944   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6764    0.0539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5699   -1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3695   -0.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5937   -0.0045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9450   -1.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7209   -2.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2964   -2.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9212   -2.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2598   -3.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6642   -2.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4406   -3.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8973   -3.3832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2283   -3.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2825   -2.4999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8424   -1.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6192   -0.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9467   -2.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  5  1  0  0  0  0
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 30 31  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004201502122D          

 32 34  0  0  0  0            999 V2000
    6.9588    0.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0279777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1(O)CC(=O)OC(C)C(O)(C(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C23H35NO8/c1-6-14(4)22(28)11-18(25)31-15(5)23(29,13(2)3)21(27)30-12-16-7-9-24-10-8-17(19(16)24)32-20(22)26/h7,13-15,17,19,28-29H,6,8-12H2,1-5H3

> <INCHI_KEY>
XXPWCNYNIAEAFN-UHFFFAOYSA-N

> <FORMULA>
C23H35NO8

> <MOLECULAR_WEIGHT>
453.532

> <EXACT_MASS>
453.236267091

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.10990447631305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(butan-2-yl)-4,9-dihydroxy-8-methyl-9-(propan-2-yl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
1.689015599999998

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.00921557746768

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.213092801817794

> <JCHEM_PKA_STRONGEST_BASIC>
6.922772167485743

> <JCHEM_POLAR_SURFACE_AREA>
122.60000000000002

> <JCHEM_REFRACTIVITY>
114.14319999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      12.990   1.733   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.458   1.888   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.557   0.639   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.025   0.793   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.189  -0.766   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.463   0.101   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.264  -1.869   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.756  -1.491   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.175  -0.008   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.831  -2.594   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.412  -4.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.487  -5.179   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.920  -4.455   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.552  -5.859   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.306  -5.124   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.756  -5.645   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.420  -6.660   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.501  -5.937   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.575  -7.040   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.008  -6.315   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.934  -5.212   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.441  -5.591   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.456  -6.774   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.026  -6.203   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       6.127  -4.667   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       5.306  -3.364   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.291  -2.180   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.786  -3.005   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.278  -2.626   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.697  -1.144   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.622  -0.041   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.367  -4.487   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   30                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   18                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29    5   31                                                  
CONECT   31   30                                                            
CONECT   32   28   22   25                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₅NO₈

Average Mass

453.5320 Da

Monoisotopic Mass

453.23627 Da

IUPAC Name

4-(butan-2-yl)-4,9-dihydroxy-8-methyl-9-(propan-2-yl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione

Traditional Name

4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione

CAS Registry Number

Not Available

SMILES

CCC(C)C1(O)CC(=O)OC(C)C(O)(C(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23

InChI Identifier

InChI=1S/C23H35NO8/c1-6-14(4)22(28)11-18(25)31-15(5)23(29,13(2)3)21(27)30-12-16-7-9-24-10-8-17(19(16)24)32-20(22)26/h7,13-15,17,19,28-29H,6,8-12H2,1-5H3

InChI Key

XXPWCNYNIAEAFN-UHFFFAOYSA-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
Parsonsia alboflavescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Tricarboxylic acid or derivatives
Pyrrolizine
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Alcohol
Carbonyl group
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	1.16	ALOGPS
logP	1.69	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.21	ChemAxon
pKa (Strongest Basic)	6.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	114.14 m³·mol⁻¹	ChemAxon
Polarizability	47.11 Å³	ChemAxon
Number of Rings	3	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

LOTUS database [Link]

Showing NP-Card for 4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione (NP0279777)

MOL for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

3D MOL for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

3D SDF for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

3D-SDF for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

PDB for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

3D PDB for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

SMILES for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

INCHI for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

Structure for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)

3D Structure for NP0279777 (4,9-dihydroxy-9-isopropyl-8-methyl-4-(sec-butyl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹⁶,¹⁹]nonadec-13-ene-3,6,10-trione)