NP-MRD: Showing NP-Card for 8-dichlororugulovasines B (NP0333398)

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Record Information

Version

2.0

Created at

2024-06-10 02:47:44 UTC

Updated at

2024-09-03 04:22:14 UTC

NP-MRD ID

NP0333398

Natural Product DOI

https://doi.org/10.57994/2787

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-dichlororugulovasines B

Description

8-Chlororugulovasine 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. 8-dichlororugulovasines B was first documented in 2015 (PMID: 26404231). Based on a literature review very few articles have been published on 8-Chlororugulovasine B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02222305232D          

 21 24  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
   -0.1057    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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 15 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333398

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H]1CC2=CNC3=C(Cl)C=CC(=C23)[C@@]11OC(=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15ClN2O2/c1-8-6-16(21-15(8)20)10-3-4-11(17)14-13(10)9(7-19-14)5-12(16)18-2/h3-4,6-7,12,18-19H,5H2,1-2H3/t12-,16-/m1/s1

> <INCHI_KEY>
SDYOUVJWVNBXPX-MLGOLLRUSA-N

> <FORMULA>
C16H15ClN2O2

> <MOLECULAR_WEIGHT>
302.76

> <EXACT_MASS>
302.0822054

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.877800106934334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,6'R)-11'-chloro-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>
3.0782338096666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.905194084252816

> <JCHEM_PKA_STRONGEST_BASIC>
9.205012002838608

> <JCHEM_POLAR_SURFACE_AREA>
54.12

> <JCHEM_REFRACTIVITY>
81.3724

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6'R)-11'-chloro-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  N   UNK     0      -0.197   1.138   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.022   2.079   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.138   3.615   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -0.133   4.484   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       2.526   4.282   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.798   3.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.790   1.575   0.000  0.00  0.00           C+0
HETATM   21  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   20                                             
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   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    4   21                                                  
CONECT   21   20   12   15                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₅ClN₂O₂

Average Mass

302.7600 Da

Monoisotopic Mass

302.08221 Da

IUPAC Name

(2R,6'R)-11'-chloro-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)-11'-chloro-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=CNC3=C(Cl)C=CC(=C23)[C@@]11OC(=O)C(C)=C1

InChI Identifier

InChI=1S/C16H15ClN2O2/c1-8-6-16(21-15(8)20)10-3-4-11(17)14-13(10)9(7-19-14)5-12(16)18-2/h3-4,6-7,12,18-19H,5H2,1-2H3/t12-,16-/m1/s1

InChI Key

SDYOUVJWVNBXPX-MLGOLLRUSA-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
Talaromyces 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
Aryl chloride
Aryl halide
2-furanone
Benzenoid
Dihydrofuran
Heteroaromatic compound
Pyrrole
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Azacycle
Secondary amine
Oxacycle
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Amine
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
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	3.08	ChemAxon
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	9.21	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	81.37 m³·mol⁻¹	ChemAxon
Polarizability	30.88 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

C00011245

Chemspider ID

143001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162891

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 8-dichlororugulovasines B (NP0333398)

MOL for NP0333398 (8-dichlororugulovasines B)

3D MOL for NP0333398 (8-dichlororugulovasines B)

3D SDF for NP0333398 (8-dichlororugulovasines B)

3D-SDF for NP0333398 (8-dichlororugulovasines B)

PDB for NP0333398 (8-dichlororugulovasines B)

3D PDB for NP0333398 (8-dichlororugulovasines B)

SMILES for NP0333398 (8-dichlororugulovasines B)

INCHI for NP0333398 (8-dichlororugulovasines B)

Structure for NP0333398 (8-dichlororugulovasines B)

3D Structure for NP0333398 (8-dichlororugulovasines B)