NP-MRD: Showing NP-Card for 3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione (NP0191344)

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Record Information

Version

2.0

Created at

2022-09-04 08:16:22 UTC

Updated at

2022-09-04 08:16:22 UTC

NP-MRD ID

NP0191344

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione

Description

119694-49-4 Belongs to the class of organic compounds known as epipolythiodioxopiperazines. Epipolythiodioxopiperazines are compounds containing an epipolythiodioxopiperazine moiety, which consists of a 2,3-dithia-5,7-diazabicyclo[2.2.2]Octane-6,8-dione ring system. One distinct characteristics of Epipolythiodioxopiperazines is the presence of unique di- or polysulfide bridges. 3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione is found in Leptosphaeria maculans. 119694-49-4 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171503232D          

 27 31  0  0  0  0            999 V2000
    7.2353    1.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4286    1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8145    1.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1008    1.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739    0.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6618   -0.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8349   -0.8823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767    0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133   -0.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4038    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195    0.7527    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0311    1.4695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763    1.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2461    2.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0499    1.1797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366    0.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -0.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4223    1.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8744    2.6148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    1.0887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037    0.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157    1.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0945    0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1047   -0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8054   -0.0258    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  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
  5 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END


  Mrv1533004171503232D          

 27 31  0  0  0  0            999 V2000
    7.2353    1.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4286    1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8145    1.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1008    1.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739    0.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6618   -0.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8349   -0.8823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767    0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133   -0.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4038    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195    0.7527    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0311    1.4695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763    1.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2461    2.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0499    1.1797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366    0.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -0.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4223    1.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8744    2.6148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    1.0887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037    0.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157    1.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0945    0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1047   -0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8054   -0.0258    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  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
  5 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191344

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC2=C(C(=O)C3(O)CC45SSC(CO)(NC4=O)C(=O)N5C3C2)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H20N2O6S2/c1-7-14(2,3)10-8(25-7)4-9-15(24,11(10)21)5-17-12(22)18-16(6-20,26-27-17)13(23)19(9)17/h7,9,20,24H,4-6H2,1-3H3,(H,18,22)

> <INCHI_KEY>
OSRGMDLTJLMMIF-UHFFFAOYSA-N

> <FORMULA>
C17H20N2O6S2

> <MOLECULAR_WEIGHT>
412.48

> <EXACT_MASS>
412.07627872

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
39.20560498986272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadec-5(9)-ene-4,13,17-trione

> <ALOGPS_LOGP>
0.26

> <JCHEM_LOGP>
0.4326016343333331

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.339452653750012

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908436303732708

> <JCHEM_PKA_STRONGEST_BASIC>
-3.192850689512923

> <JCHEM_POLAR_SURFACE_AREA>
116.17

> <JCHEM_REFRACTIVITY>
98.87769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadec-5(9)-ene-4,13,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      13.506   2.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.000   2.141   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.854   3.170   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.521   2.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.845   0.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.702  -0.141   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.025  -1.647   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.237   0.332   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.339  -1.205   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.811  -0.349   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.487   0.529   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0       3.396   1.405   0.000  0.00  0.00           S+0
HETATM   13  S   UNK     0       3.791   2.743   0.000  0.00  0.00           S+0
HETATM   14  C   UNK     0       2.756   3.682   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.999   5.023   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.459   5.039   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       1.960   2.202   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.682   0.638   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.813  -0.633   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.522   3.593   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.366   4.881   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       5.297   2.032   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.913   1.838   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.056   2.870   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.376   0.733   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.395  -0.807   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.703  -0.048   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6   25                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   23                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   18   22                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17   20                                             
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18                                                            
CONECT   20   14   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   11   23                                                  
CONECT   23   22    8   24                                                  
CONECT   24   23    4                                                       
CONECT   25    5    2   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₀N₂O₆S₂

Average Mass

412.4800 Da

Monoisotopic Mass

412.07628 Da

IUPAC Name

3-hydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadec-5(9)-ene-4,13,17-trione

Traditional Name

3-hydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadec-5(9)-ene-4,13,17-trione

CAS Registry Number

Not Available

SMILES

CC1OC2=C(C(=O)C3(O)CC45SSC(CO)(NC4=O)C(=O)N5C3C2)C1(C)C

InChI Identifier

InChI=1S/C17H20N2O6S2/c1-7-14(2,3)10-8(25-7)4-9-15(24,11(10)21)5-17-12(22)18-16(6-20,26-27-17)13(23)19(9)17/h7,9,20,24H,4-6H2,1-3H3,(H,18,22)

InChI Key

OSRGMDLTJLMMIF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Leptosphaeria maculans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epipolythiodioxopiperazines. Epipolythiodioxopiperazines are compounds containing an epipolythiodioxopiperazine moiety, which consists of a 2,3-dithia-5,7-diazabicyclo[2.2.2]Octane-6,8-dione ring system. One distinct characteristics of Epipolythiodioxopiperazines is the presence of unique di- or polysulfide bridges.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Epipolythiodioxopiperazines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Epipolythiodioxopiperazine
Indole or derivatives
N-alkylpiperazine
Cyclohexenone
Dithiazinane
Dihydrofuran
Pyrrolidine
Tertiary alcohol
Tertiary carboxylic acid amide
Vinylogous ester
Secondary carboxylic acid amide
Carboxamide group
Ketone
Lactam
Organic disulfide
Oxacycle
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Primary alcohol
Organic oxide
Organic nitrogen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.26	ALOGPS
logP	0.43	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.17 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.88 m³·mol⁻¹	ChemAxon
Polarizability	39.21 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

189682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione (NP0191344)

MOL for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

3D MOL for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

3D SDF for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

3D-SDF for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

PDB for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

3D PDB for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

SMILES for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

INCHI for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

Structure for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)

3D Structure for NP0191344 (3,17-dihydroxy-14-(hydroxymethyl)-6,6,7-trimethyl-8-oxa-15,16-dithia-12,18-diazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁵,⁹]octadeca-5(9),17-diene-4,13-dione)