NP-MRD: Showing NP-Card for (1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one (NP0177831)

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Record Information

Version

2.0

Created at

2022-09-03 15:43:36 UTC

Updated at

2022-09-03 15:43:36 UTC

NP-MRD ID

NP0177831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one

Description

16-Hydroxyalstonisine belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. (1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one is found in Alstonia macrophylla. (1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one was first documented in 2004 (PMID: 15104482). Based on a literature review very few articles have been published on 16-Hydroxyalstonisine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032217432D          

 26 30  0  0  1  0            999 V2000
    6.9256    3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3802    2.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715    2.9804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6436    2.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4524    1.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7158    1.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1704    0.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3616    0.6349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6827   -0.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982    1.4167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3228    1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191    1.2675    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1011    0.4426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9146   -0.0585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0938   -0.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5172    0.4488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2708   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7629   -1.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -0.3474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -1.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824    0.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    0.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    1.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9923    2.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495    1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8446    0.9265    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10  4  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 16 26  1  0  0  0  0
M  END


  Mrv1652309032217432D          

 26 30  0  0  1  0            999 V2000
    6.9256    3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3802    2.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715    2.9804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6436    2.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4524    1.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7158    1.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1704    0.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3616    0.6349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6827   -0.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0982    1.4167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3228    1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191    1.2675    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1011    0.4426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9146   -0.0585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0938   -0.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5172    0.4488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2708   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7629   -1.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -0.3474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -1.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824    0.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    0.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    1.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9923    2.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495    1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8446    0.9265    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10  4  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 16 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0177831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@@]2(C[C@H]3N[C@@H]2C[C@H]2C(=COC[C@@]32O)C(C)=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O4/c1-11(23)12-9-26-10-20(25)14(12)7-16-19(8-17(20)21-16)13-5-3-4-6-15(13)22(2)18(19)24/h3-6,9,14,16-17,21,25H,7-8,10H2,1-2H3/t14-,16+,17+,19-,20-/m0/s1

> <INCHI_KEY>
HXDMVLNKWWFVGR-CIJNOWTPSA-N

> <FORMULA>
C20H22N2O4

> <MOLECULAR_WEIGHT>
354.406

> <EXACT_MASS>
354.157957196

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.58811818194992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2'S,3S,7'S,9'R)-6'-acetyl-2'-hydroxy-1-methyl-1,2-dihydro-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2-one

> <JCHEM_LOGP>
0.046399644999999226

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.71040761989307

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.14269554352816

> <JCHEM_PKA_STRONGEST_BASIC>
9.58091356819348

> <JCHEM_POLAR_SURFACE_AREA>
78.86999999999999

> <JCHEM_REFRACTIVITY>
94.41190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2'S,3S,7'S,9'R)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      12.928   6.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.910   5.259   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.400   5.563   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.401   3.800   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.911   3.496   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.403   2.037   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.385   0.881   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.875   1.185   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.474  -0.233   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.383   2.645   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.936   3.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.622   2.366   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       9.522   0.826   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      11.041  -0.109   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.508  -0.264   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.432   0.838   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.972  -0.632   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.891  -1.868   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       6.432  -0.648   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.541  -1.904   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.941   0.811   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.527   1.422   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.350   2.952   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.586   3.870   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.999   3.259   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.177   1.730   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12   17   26                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21   16                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₄

Average Mass

354.4060 Da

Monoisotopic Mass

354.15796 Da

IUPAC Name

(1'R,2'S,3S,7'S,9'R)-6'-acetyl-2'-hydroxy-1-methyl-1,2-dihydro-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2-one

Traditional Name

(1'R,2'S,3S,7'S,9'R)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2-one

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@@]2(C[C@H]3N[C@@H]2C[C@H]2C(=COC[C@@]32O)C(C)=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C20H22N2O4/c1-11(23)12-9-26-10-20(25)14(12)7-16-19(8-17(20)21-16)13-5-3-4-6-15(13)22(2)18(19)24/h3-6,9,14,16-17,21,25H,7-8,10H2,1-2H3/t14-,16+,17+,19-,20-/m0/s1

InChI Key

HXDMVLNKWWFVGR-CIJNOWTPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alstonia macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Indole or derivatives
Aralkylamine
Benzenoid
Piperidine
Vinylogous ester
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Lactam
Ketone
Carboxamide group
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	0.046	ChemAxon
pKa (Strongest Acidic)	13.14	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.87 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.41 m³·mol⁻¹	ChemAxon
Polarizability	36.59 Å³	ChemAxon
Number of Rings	5	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

101730879

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kam TS, Choo YM: New indole alkaloids from Alstonia macrophylla. J Nat Prod. 2004 Apr;67(4):547-52. doi: 10.1021/np034041v. [PubMed:15104482 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one (NP0177831)

MOL for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

3D MOL for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

3D SDF for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

3D-SDF for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

PDB for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

3D PDB for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

SMILES for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

INCHI for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

Structure for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)

3D Structure for NP0177831 ((1'r,2's,3s,7's,9'r)-6'-acetyl-2'-hydroxy-1-methyl-4'-oxa-12'-azaspiro[indole-3,10'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2-one)