NP-MRD: Showing NP-Card for Aspergillide A (NP0044065)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-11-12 23:48:08 UTC

Updated at

2021-11-26 17:45:02 UTC

NP-MRD ID

NP0044065

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspergillide A

Description

Aspergillide A is found in Aspergillus ostianus. It was first documented in 2008 (PMID: 18078344). Based on a literature review very few articles have been published on (1S,5S,11R,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]Pentadec-9-en-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -4.0071    1.7197    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6827    0.9850    0.5432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9805   -0.5198    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6184   -1.0097   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5671   -2.4236   -0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894   -2.9486   -0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8064   -2.4751    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853   -1.1748    0.2124 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0225   -1.3388    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5307    0.0861    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    1.1022   -0.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1305    2.3609    0.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    0.9111   -0.7645 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5489    1.6611    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128    2.1054   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5923    3.2283   -1.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971    1.4388   -0.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323   -0.4240   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8142    1.1878    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8405    2.7475    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2608    1.8487   -0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2425    1.1002    1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563   -0.9989    1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6859   -0.6248   -0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -0.8640    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642   -0.3559   -1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059   -2.4871   -1.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252   -3.0750   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -3.8935   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -3.1403    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3345   -0.6472    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577   -1.9548    1.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675   -1.7015   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176    0.3310    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6330    0.0382    0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068    1.0996   -1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1882    3.0327   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3118    1.3708   -1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1327    2.5620    0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539    1.1404    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 13 18  1  0
 17  2  1  0
 18  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  1
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  6
 12 37  1  0
 13 38  1  6
 14 39  1  0
 14 40  1  0
M  END


  Mrv1652311132100482D          

 18 19  0  0  1  0            999 V2000
    4.7289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.3645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    0.9355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6039    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.3645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2539    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  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  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  6  0  0  0
  8 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044065

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCCC=C[C@H]2CC[C@H](O)[C@H](CC(=O)O1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6,10-13,15H,2-3,5,7-9H2,1H3/t10-,11-,12-,13-/m0/s1

> <INCHI_KEY>
FDJDTDDUDZAAFP-CYDGBPFRSA-N

> <FORMULA>
C14H22O4

> <MOLECULAR_WEIGHT>
254.326

> <EXACT_MASS>
254.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.198180893248455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5S,11R,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.8305004899999993

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.173179964602149

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1604510834830206

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
68.1349

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,11R,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       8.827   5.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.057   4.414   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.827   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.057   1.746   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.517   1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   0.413   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.207   0.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.437   1.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.897   1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.127   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.127   5.747   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.437   4.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.207   5.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747   5.747   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.517   4.414   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.517   7.081   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.207   3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15    2                                                       
CONECT   17   15                                                            
CONECT   18   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₂O₄

Average Mass

254.3260 Da

Monoisotopic Mass

254.15181 Da

IUPAC Name

(1S,5S,11R,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

Traditional Name

(1S,5S,11R,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCCC=C[C@H]2CC[C@H](O)[C@H](CC(=O)O1)O2

InChI Identifier

InChI=1S/C14H22O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6,10-13,15H,2-3,5,7-9H2,1H3/t10-,11-,12-,13-/m0/s1

InChI Key

FDJDTDDUDZAAFP-CYDGBPFRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus ostianus	Fungi	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	1.65	ALOGPS
logP	1.83	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.17	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.13 m³·mol⁻¹	ChemAxon
Polarizability	27.2 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

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

156583123

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kito K, Ookura R, Yoshida S, Namikoshi M, Ooi T, Kusumi T: New cytotoxic 14-membered macrolides from marine-derived fungus Aspergillus ostianus. Org Lett. 2008 Jan 17;10(2):225-8. doi: 10.1021/ol702598q. Epub 2007 Dec 14. [PubMed:18078344 ]

Showing NP-Card for Aspergillide A (NP0044065)

MOL for NP0044065 (Aspergillide A)

3D MOL for NP0044065 (Aspergillide A)

3D SDF for NP0044065 (Aspergillide A)

3D-SDF for NP0044065 (Aspergillide A)

PDB for NP0044065 (Aspergillide A)

3D PDB for NP0044065 (Aspergillide A)

SMILES for NP0044065 (Aspergillide A)

INCHI for NP0044065 (Aspergillide A)

Structure for NP0044065 (Aspergillide A)

3D Structure for NP0044065 (Aspergillide A)