NP-MRD: Showing NP-Card for Buxomeline (NP0066870)

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Record Information

Version

2.0

Created at

2022-04-28 11:06:15 UTC

Updated at

2022-04-28 11:06:15 UTC

NP-MRD ID

NP0066870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Buxomeline

Description

Methyl (1R,12S,14S,19R,21S)-21-hydroxy-19-methyl-20-oxa-5,15-diazahexacyclo[12.4.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]Henicosa-3,6,8,10,17-pentaene-3-carboxylate belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Buxomeline is found in Melodinus celastroides. Based on a literature review very few articles have been published on methyl (1R,12S,14S,19R,21S)-21-hydroxy-19-methyl-20-oxa-5,15-diazahexacyclo[12.4.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]Henicosa-3,6,8,10,17-pentaene-3-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282213062D          

 27 32  0  0  1  0            999 V2000
    5.2699    0.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8148    0.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5507   -0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7418   -0.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1970    0.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4129   -0.2598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5193   -1.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766   -1.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038   -1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9803   -0.5552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6738   -0.1269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7996    0.8365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2333    1.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097    1.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    0.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2344    0.7534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3115    0.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550    0.5397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -0.3410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5261   -0.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8277   -0.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0188   -2.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937   -2.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862   -3.0517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5284   -3.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3345   -1.3192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 17 13  1  6  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 12 22  1  1  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 27  1  0  0  0  0
  4 27  1  0  0  0  0
M  END


  Mrv1652304282213062D          

 27 32  0  0  1  0            999 V2000
    5.2699    0.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8148    0.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5507   -0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7418   -0.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1970    0.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4129   -0.2598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5193   -1.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766   -1.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038   -1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9803   -0.5552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6738   -0.1269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7996    0.8365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2333    1.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097    1.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    0.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2344    0.7534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3115    0.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550    0.5397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -0.3410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5261   -0.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8277   -0.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0188   -2.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937   -2.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862   -3.0517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5284   -3.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3345   -1.3192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 17 13  1  6  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 12 22  1  1  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 27  1  0  0  0  0
  4 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2NC3=CC=CC=C3[C@@]22C[C@@H]3O[C@H](C)[C@@]4(C1)C=CCN3[C@]24O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O4/c1-12-19-8-5-9-23-16(27-12)11-20(21(19,23)25)14-6-3-4-7-15(14)22-17(20)13(10-19)18(24)26-2/h3-8,12,16,22,25H,9-11H2,1-2H3/t12-,16+,19+,20+,21-/m1/s1

> <INCHI_KEY>
DANNLLVHDDUBFO-PKQOHKHLSA-N

> <FORMULA>
C21H22N2O4

> <MOLECULAR_WEIGHT>
366.417

> <EXACT_MASS>
366.157957196

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
56.779789532179365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12S,14S,19R,21S)-21-hydroxy-19-methyl-20-oxa-5,15-diazahexacyclo[12.4.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-3,6,8,10,17-pentaene-3-carboxylate

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.6581468019999992

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.106522599004908

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.121361147617694

> <JCHEM_PKA_STRONGEST_BASIC>
4.994694788910337

> <JCHEM_POLAR_SURFACE_AREA>
71.03

> <JCHEM_REFRACTIVITY>
101.9378

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12S,14S,19R,21S)-21-hydroxy-19-methyl-20-oxa-5,15-diazahexacyclo[12.4.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-3,6,8,10,17-pentaene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.837   1.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.854   0.647   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.361  -0.812   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.851  -1.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.834   0.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.327   1.501   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.371  -0.485   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.569  -2.143   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.370  -3.191   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.927  -2.629   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.697  -1.036   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.991  -0.237   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.226   1.561   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.169   2.609   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.818   1.933   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.819   0.182   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.171   1.406   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.181   1.199   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.343   1.007   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.236  -0.637   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.982  -1.531   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.278  -1.750   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.635  -4.708   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.082  -5.237   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.454  -5.697   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.720  -7.213   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       8.091  -2.462   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12   18                                             
CONECT    8    7    9   27                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16   20                                             
CONECT   12   11    7   13   22                                             
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   13   18   19                                                  
CONECT   18   17    7                                                       
CONECT   19   17   20                                                       
CONECT   20   19   11   21                                                  
CONECT   21   20                                                            
CONECT   22   12                                                            
CONECT   23    9   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27    8    4                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,12S,14S,19R,21S)-21-hydroxy-19-methyl-20-oxa-5,15-diazahexacyclo[12.4.2.1,.0,.0,.0,]henicosa-3,6,8,10,17-pentaene-3-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₂N₂O₄

Average Mass

366.4170 Da

Monoisotopic Mass

366.15796 Da

IUPAC Name

methyl (1R,12S,14S,19R,21S)-21-hydroxy-19-methyl-20-oxa-5,15-diazahexacyclo[12.4.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-3,6,8,10,17-pentaene-3-carboxylate

Traditional Name

methyl (1R,12S,14S,19R,21S)-21-hydroxy-19-methyl-20-oxa-5,15-diazahexacyclo[12.4.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-3,6,8,10,17-pentaene-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2NC3=CC=CC=C3[C@@]22C[C@@H]3O[C@H](C)[C@@]4(C1)C=CCN3[C@]24O

InChI Identifier

InChI=1S/C21H22N2O4/c1-12-19-8-5-9-23-16(27-12)11-20(21(19,23)25)14-6-3-4-7-15(14)22-17(20)13(10-19)18(24)26-2/h3-8,12,16,22,25H,9-11H2,1-2H3/t12-,16+,19+,20+,21-/m1/s1

InChI Key

DANNLLVHDDUBFO-PKQOHKHLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melodinus celastroides	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Dihydroindole
Secondary aliphatic/aromatic amine
Oxepane
Benzenoid
N-alkylpyrrolidine
Oxazinane
1,3-oxazinane
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Hemiaminal
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Secondary amine
Monocarboxylic acid or derivatives
Enamine
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	1.82	ALOGPS
logP	1.66	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.12	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.94 m³·mol⁻¹	ChemAxon
Polarizability	56.78 Å³	ChemAxon
Number of Rings	6	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

163067994

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Buxomeline (NP0066870)

MOL for NP0066870 (Buxomeline)

3D MOL for NP0066870 (Buxomeline)

3D SDF for NP0066870 (Buxomeline)

3D-SDF for NP0066870 (Buxomeline)

PDB for NP0066870 (Buxomeline)

3D PDB for NP0066870 (Buxomeline)

SMILES for NP0066870 (Buxomeline)

INCHI for NP0066870 (Buxomeline)

Structure for NP0066870 (Buxomeline)

3D Structure for NP0066870 (Buxomeline)