NP-MRD: Showing NP-Card for (+)-Aspirochlorine (NP0078314)

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Record Information

Version

2.0

Created at

2022-04-28 23:24:45 UTC

Updated at

2022-04-28 23:24:45 UTC

NP-MRD ID

NP0078314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Aspirochlorine

Description

Aspirochlorin belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (+)-Aspirochlorine is found in Aspergillus flavus. Based on a literature review very few articles have been published on aspirochlorin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -3.3190   -0.4102    2.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455   -0.7602    1.6141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631   -0.4433    0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391   -0.6329   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8201   -1.4196   -0.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836    0.0980   -1.9963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0225    1.3312   -1.7450 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938    1.3067   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1425    2.2970   -0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    0.1261   -0.0709 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2164    0.4240    1.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5605    0.2454    0.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457    0.6876    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9930    0.3809    0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1496    0.8629    1.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955   -0.4046   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6428   -0.8460   -0.9429 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9362   -0.8508   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844   -0.5420   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2861   -0.8727   -0.8128 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2251   -0.6844   -2.5965 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064   -0.8610   -3.1974 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9614   -1.2860    2.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8207    0.1401    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2917    0.2668    2.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8006    0.2946   -2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3878    2.1824   -2.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    1.3145    2.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0809    1.4380    2.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290   -1.4745   -1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0779   -1.9080   -0.4714 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  1
 11 12  1  0
 12 19  2  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 16 14  1  0
 14 15  1  0
 14 13  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 10  3  1  0
 20 10  1  0
 22  6  1  0
 13 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  6
  7 27  1  0
 18 30  1  0
 15 29  1  0
 13 28  1  0
 20 31  1  6
M  END


  Mrv1652304292201242D          

 22 25  0  0  1  0            999 V2000
    1.4188   -0.4208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7674    0.4164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4069    1.2413    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545    1.5300    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831    0.8965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1145    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8785   -0.3030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302   -0.6066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3040   -1.3999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8779   -1.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7085    0.8467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0776   -0.3206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    0.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514   -0.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -0.8983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6548   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2190   -0.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9798    0.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1764    0.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5440    1.3377    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0224   -0.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 11  1  1  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  1 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)[C@H]2NC(=O)[C@@]11OC3=C(C=C(Cl)C(O)=C3)[C@@H]1SS2

> <INCHI_IDENTIFIER>
InChI=1S/C12H9ClN2O5S2/c1-19-15-10(17)9-14-11(18)12(15)8(21-22-9)4-2-5(13)6(16)3-7(4)20-12/h2-3,8-9,16H,1H3,(H,14,18)/t8-,9-,12+/m0/s1

> <INCHI_KEY>
XMFSSFONDVHNFO-HOTUBEGUSA-N

> <FORMULA>
C12H9ClN2O5S2

> <MOLECULAR_WEIGHT>
360.78

> <EXACT_MASS>
359.9641414

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
31.810985639850333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,12S)-6-chloro-5-hydroxy-15-methoxy-2-oxa-10,11-dithia-13,15-diazatetracyclo[10.2.2.0^{1,9}.0^{3,8}]hexadeca-3(8),4,6-triene-14,16-dione

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
2.054567214666667

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.521564554382982

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.777322651207114

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5672539533340935

> <JCHEM_POLAR_SURFACE_AREA>
88.10000000000001

> <JCHEM_REFRACTIVITY>
80.2367

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,12S)-6-chloro-5-hydroxy-15-methoxy-2-oxa-10,11-dithia-13,15-diazatetracyclo[10.2.2.0^{1,9}.0^{3,8}]hexadeca-3(8),4,6-triene-14,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       2.648  -0.785   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.299   0.777   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       2.626   2.317   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       1.035   2.856   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      -0.155   1.673   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.214   0.015   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.640  -0.566   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       0.990  -1.132   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.567  -2.613   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.639  -3.719   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.323   1.580   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.493   0.147   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.145  -0.598   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.876   0.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.323  -0.874   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.971  -1.677   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.822  -1.224   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.875  -0.100   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.429   1.373   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.929   1.724   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       8.482   2.497   0.000  0.00  0.00          Cl+0
HETATM   22  O   UNK     0       9.375  -0.451   0.000  0.00  0.00           O+0
CONECT    1    2    8   12   16                                             
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    1    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    5   12                                                       
CONECT   12   11    1   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15    1                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   14                                                       
CONECT   21   19                                                            
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₉ClN₂O₅S₂

Average Mass

360.7800 Da

Monoisotopic Mass

359.96414 Da

IUPAC Name

(1S,9S,12S)-6-chloro-5-hydroxy-15-methoxy-2-oxa-10,11-dithia-13,15-diazatetracyclo[10.2.2.0^{1,9}.0^{3,8}]hexadeca-3(8),4,6-triene-14,16-dione

Traditional Name

(1S,9S,12S)-6-chloro-5-hydroxy-15-methoxy-2-oxa-10,11-dithia-13,15-diazatetracyclo[10.2.2.0^{1,9}.0^{3,8}]hexadeca-3(8),4,6-triene-14,16-dione

CAS Registry Number

Not Available

SMILES

CON1C(=O)[C@H]2NC(=O)[C@@]11OC3=C(C=C(Cl)C(O)=C3)[C@@H]1SS2

InChI Identifier

InChI=1S/C12H9ClN2O5S2/c1-19-15-10(17)9-14-11(18)12(15)8(21-22-9)4-2-5(13)6(16)3-7(4)20-12/h2-3,8-9,16H,1H3,(H,14,18)/t8-,9-,12+/m0/s1

InChI Key

XMFSSFONDVHNFO-HOTUBEGUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus flavus	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Thiodioxopiperazine
Coumaran
Dioxopiperazine
2-halophenol
2,5-dioxopiperazine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl chloride
Aryl halide
Benzenoid
1,4-diazinane
Piperazine
Carboxamide group
Lactam
Organic disulfide
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Oxacycle
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
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	1.79	ALOGPS
logP	2.05	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.24 m³·mol⁻¹	ChemAxon
Polarizability	31.81 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

C00042248

Chemspider ID

67158887

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13945563

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Aspirochlorine (NP0078314)

MOL for NP0078314 ((+)-Aspirochlorine)

3D MOL for NP0078314 ((+)-Aspirochlorine)

3D SDF for NP0078314 ((+)-Aspirochlorine)

3D-SDF for NP0078314 ((+)-Aspirochlorine)

PDB for NP0078314 ((+)-Aspirochlorine)

3D PDB for NP0078314 ((+)-Aspirochlorine)

SMILES for NP0078314 ((+)-Aspirochlorine)

INCHI for NP0078314 ((+)-Aspirochlorine)

Structure for NP0078314 ((+)-Aspirochlorine)

3D Structure for NP0078314 ((+)-Aspirochlorine)