NP-MRD: Showing NP-Card for 2,8-dichlororugulovasines B (NP0333400)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-06-10 02:53:36 UTC

Updated at

2024-09-03 04:22:15 UTC

NP-MRD ID

NP0333400

Natural Product DOI

https://doi.org/10.57994/2789

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,8-dichlororugulovasines B

Description

2,8-Dichlororugulovasines B belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. 2,8-dichlororugulovasines B was first documented in 2015 (PMID: 26404231). Based on a literature review very few articles have been published on 2,8-dichlororugulovasines B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02222305292D          

 22 25  0  0  1  0            999 V2000
    4.6940   -0.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999    0.2467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9134    1.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2700    1.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678   -0.5450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9374   -1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054   -1.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662   -0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1719   -0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934   -0.8482    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1057    0.6099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    1.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098    1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0715    2.4020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0346    1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303    0.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286    0.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 22  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333400

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H]1CC2=C(Cl)NC3=C(Cl)C=CC(=C23)[C@@]11OC(=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14Cl2N2O2/c1-7-6-16(22-15(7)21)9-3-4-10(17)13-12(9)8(14(18)20-13)5-11(16)19-2/h3-4,6,11,19-20H,5H2,1-2H3/t11-,16-/m1/s1

> <INCHI_KEY>
IENLABAWRVNXDR-BDJLRTHQSA-N

> <FORMULA>
C16H14Cl2N2O2

> <MOLECULAR_WEIGHT>
337.2

> <EXACT_MASS>
336.0432331

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
33.26336246999654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,6'R)-3',11'-dichloro-4-methyl-6'-(methylamino)-5H-2'-azaspiro[furan-2,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),3',8'(12'),9'-tetraen-5-one

> <JCHEM_LOGP>
3.3972891416666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.785747727914398

> <JCHEM_PKA_STRONGEST_BASIC>
9.066357013220852

> <JCHEM_POLAR_SURFACE_AREA>
54.12

> <JCHEM_REFRACTIVITY>
86.17829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6'R)-3',11'-dichloro-4-methyl-6'-(methylamino)-2'-azaspiro[furan-2,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),3',8'(12'),9'-tetraen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-FEB-23         0                                  
HETATM    1  C   UNK     0       8.762  -0.313   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.338   0.272   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.027  -0.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.853   0.461   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.438   1.885   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.974   1.769   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.971   2.942   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.420  -1.017   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.483  -2.131   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.050  -3.609   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.924  -1.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.860  -0.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.321  -0.312   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -0.548  -1.583   0.000  0.00  0.00          Cl+0
HETATM   15  N   UNK     0      -0.197   1.138   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.022   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.138   3.615   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -0.133   4.484   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       2.526   4.282   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.798   3.413   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.790   1.575   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.293   1.211   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8   21                                             
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21   12   16                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄Cl₂N₂O₂

Average Mass

337.2000 Da

Monoisotopic Mass

336.04323 Da

IUPAC Name

(2R,6'R)-3',11'-dichloro-4-methyl-6'-(methylamino)-5H-2'-azaspiro[furan-2,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),3',8'(12'),9'-tetraen-5-one

Traditional Name

(2R,6'R)-3',11'-dichloro-4-methyl-6'-(methylamino)-2'-azaspiro[furan-2,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),3',8'(12'),9'-tetraen-5-one

CAS Registry Number

Not Available

SMILES

CN[C@@H]1CC2=C(Cl)NC3=C(Cl)C=CC(=C23)[C@@]11OC(=O)C(C)=C1

InChI Identifier

InChI=1S/C16H14Cl2N2O2/c1-7-6-16(22-15(7)21)9-3-4-10(17)13-12(9)8(14(18)20-13)5-11(16)19-2/h3-4,6,11,19-20H,5H2,1-2H3/t11-,16-/m1/s1

InChI Key

IENLABAWRVNXDR-BDJLRTHQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	livia.soman@unifesp.br	Unifesp - Universidade Federal de São Paulo	Lívia Soman	2024-06-10	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
wortmannii		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Isoindole or derivatives
Aralkylamine
Benzenoid
Substituted pyrrole
2-furanone
Aryl halide
Aryl chloride
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrole
Dihydrofuran
Lactone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen 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	3.4	ChemAxon
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.18 m³·mol⁻¹	ChemAxon
Polarizability	33.26 Å³	ChemAxon
Number of Rings	4	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

Not Available

Showing NP-Card for 2,8-dichlororugulovasines B (NP0333400)

MOL for NP0333400 (2,8-dichlororugulovasines B)

3D MOL for NP0333400 (2,8-dichlororugulovasines B)

3D SDF for NP0333400 (2,8-dichlororugulovasines B)

3D-SDF for NP0333400 (2,8-dichlororugulovasines B)

PDB for NP0333400 (2,8-dichlororugulovasines B)

3D PDB for NP0333400 (2,8-dichlororugulovasines B)

SMILES for NP0333400 (2,8-dichlororugulovasines B)

INCHI for NP0333400 (2,8-dichlororugulovasines B)

Structure for NP0333400 (2,8-dichlororugulovasines B)

3D Structure for NP0333400 (2,8-dichlororugulovasines B)