NP-MRD: Showing NP-Card for Acremoauxin A (NP0050707)

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Record Information

Version

2.0

Created at

2022-04-27 22:02:57 UTC

Updated at

2022-04-27 22:02:58 UTC

NP-MRD ID

NP0050707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acremoauxin A

Description

Acremoauxin A belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. Acremoauxin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Acremoauxin A is found in Acremonium roseum, Acremonium rutilum and Apis cerana. Acremoauxin A was first documented in 2007 (PMID: 17900115). Based on a literature review very few articles have been published on acremoauxin A (PMID: 22692953).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200022D          

 23 24  0  0  1  0            999 V2000
   -0.5889   -2.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256   -2.2047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1256   -1.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400   -2.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400   -3.4422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545   -2.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690   -2.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9835   -2.2047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6979   -2.6172    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4124   -2.2047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4124   -1.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1269   -2.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413   -2.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6979   -3.4422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9835   -1.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3426   -2.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946   -2.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821   -3.6092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6751   -3.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016   -2.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565   -1.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4045   -1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5975   -1.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  1  0  0  0
  8 15  1  1  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  2  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 16 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050707

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](C(=O)OC[C@@H](O)[C@H](O)[C@H](O)CO)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO6/c1-9(11-6-17-12-5-3-2-4-10(11)12)16(22)23-8-14(20)15(21)13(19)7-18/h2-6,9,13-15,17-21H,7-8H2,1H3/t9-,13-,14-,15-/m1/s1

> <INCHI_KEY>
YBXVDDODTFXOHM-SEWBAHNZSA-N

> <FORMULA>
C16H21NO6

> <MOLECULAR_WEIGHT>
323.345

> <EXACT_MASS>
323.1368874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.47371223303531

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl (2R)-2-(1H-indol-3-yl)propanoate

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
-0.18247040533333314

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.739044923071212

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.754048869845917

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742037151631964

> <JCHEM_POLAR_SURFACE_AREA>
123.01000000000002

> <JCHEM_REFRACTIVITY>
81.97550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acremoauxin A

> <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      -1.099  -4.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.234  -4.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.234  -2.575   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.568  -4.885   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.568  -6.425   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.902  -4.115   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.235  -4.885   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.569  -4.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.903  -4.885   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.236  -4.115   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.236  -2.575   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.570  -4.885   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.904  -4.115   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.903  -6.425   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.569  -2.575   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.506  -4.259   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.537  -5.403   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -2.767  -6.737   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -1.260  -6.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.043  -5.083   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.519  -3.619   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.488  -2.474   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.982  -2.794   0.000  0.00  0.00           C+0
CONECT    1    2   16   19                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    9                                                            
CONECT   15    8                                                            
CONECT   16    1   17   23                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    1                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
2-(3-Indolyl)propanoylmannitol	ChEBI

Chemical Formula

C₁₆H₂₁NO₆

Average Mass

323.3450 Da

Monoisotopic Mass

323.13689 Da

IUPAC Name

(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl (2R)-2-(1H-indol-3-yl)propanoate

Traditional Name

acremoauxin A

CAS Registry Number

Not Available

SMILES

C[C@@H](C(=O)OC[C@@H](O)[C@H](O)[C@H](O)CO)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C16H21NO6/c1-9(11-6-17-12-5-3-2-4-10(11)12)16(22)23-8-14(20)15(21)13(19)7-18/h2-6,9,13-15,17-21H,7-8H2,1H3/t9-,13-,14-,15-/m1/s1

InChI Key

YBXVDDODTFXOHM-SEWBAHNZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acremonium roseum	Fungi	KNApSAcK
Acremonium rutilum	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
Pentose monosaccharide
3-alkylindole
Indole
Monosaccharide
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolyl carboxylate ester (CHEBI:2431 )
pentitol derivative (CHEBI:2431 )

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	0.63	ALOGPS
logP	-0.18	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.75	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	123.01 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	81.98 m³·mol⁻¹	ChemAxon
Polarizability	33.47 Å³	ChemAxon
Number of Rings	2	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

C00001524

Chemspider ID

390231

KEGG Compound ID

C08468

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441556

PDB ID

Not Available

ChEBI ID

2431

Good Scents ID

Not Available

References

General References

Talontsi FM, Nwemeguela Kenla TJ, Dittrich B, Douanla-Meli C, Laatsch H: Paeciloside A, a new antimicrobial and cytotoxic polyketide from Paecilomyces sp. strain CAFT156. Planta Med. 2012 Jun;78(10):1020-3. doi: 10.1055/s-0031-1298622. Epub 2012 Jun 12. [PubMed:22692953 ]
Richter JM, Whitefield BW, Maimone TJ, Lin DW, Castroviejo MP, Baran PS: Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: total synthesis of acremoauxin A and oxazinin 3. J Am Chem Soc. 2007 Oct 24;129(42):12857-69. doi: 10.1021/ja074392m. Epub 2007 Sep 27. [PubMed:17900115 ]

Showing NP-Card for Acremoauxin A (NP0050707)

MOL for NP0050707 (Acremoauxin A)

3D MOL for NP0050707 (Acremoauxin A)

3D SDF for NP0050707 (Acremoauxin A)

3D-SDF for NP0050707 (Acremoauxin A)

PDB for NP0050707 (Acremoauxin A)

3D PDB for NP0050707 (Acremoauxin A)

SMILES for NP0050707 (Acremoauxin A)

INCHI for NP0050707 (Acremoauxin A)

Structure for NP0050707 (Acremoauxin A)

3D Structure for NP0050707 (Acremoauxin A)