NP-MRD: Showing NP-Card for (1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione (NP0141477)

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Record Information

Version

2.0

Created at

2022-09-01 19:48:49 UTC

Updated at

2022-09-01 19:48:50 UTC

NP-MRD ID

NP0141477

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione

Description

(1S,4R,7S,12S)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]Heptadeca-5,10-diene-9,15-dione belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. (1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione is found in Neolitsea aciculata. Based on a literature review very few articles have been published on (1S,4R,7S,12S)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]Heptadeca-5,10-diene-9,15-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309012221482D          

 21 25  0  0  1  0            999 V2000
    4.1243    2.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3848    1.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2518    0.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738    0.7684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7269   -0.0239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761   -0.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379   -1.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -0.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177   -0.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    0.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368    0.8270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2200    0.9686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4107    1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706    2.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418    2.2776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0388    2.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193    2.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6168    2.2647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4019    1.5286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858    1.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273    1.5035    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
  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
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  6  0  0  0
  4 19  1  1  0  0  0
 15 20  1  1  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 15 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141477

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@@]23O[C@@H]1CC[C@]14OC1[C@@H](OC4=O)C2=C(C)C(=O)O3

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c1-6-5-15-9(7(2)12(16)21-15)10-11-14(20-11,13(17)18-10)4-3-8(6)19-15/h5,8,10-11H,3-4H2,1-2H3/t8-,10+,11?,14+,15+/m1/s1

> <INCHI_KEY>
RRNMDHLOLUUHIK-ABZZKLJDSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.271

> <EXACT_MASS>
290.079038171

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.23820913951856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,7S,12S)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1^{4,7}.0^{1,13}.0^{7,11}]heptadeca-5,10-diene-9,15-dione

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
1.8039846036666667

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.075453662697433

> <JCHEM_POLAR_SURFACE_AREA>
74.36

> <JCHEM_REFRACTIVITY>
68.11000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,7S,12S)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1^{4,7}.0^{1,13}.0^{7,11}]heptadeca-5,10-diene-9,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0       7.699   4.129   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.318   3.446   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.070   1.839   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.431   1.434   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.090  -0.045   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.062  -1.201   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.364  -2.711   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.675  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.340  -1.299   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.798   1.013   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.189   1.544   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.411   1.808   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.767   3.391   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.185   3.990   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.638   4.251   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.939   5.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.583   5.294   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.885   4.227   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.483   2.853   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.347   3.067   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.171   2.807   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10   19                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20   21                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2   19                                                  
CONECT   19   18    4                                                       
CONECT   20   15   21                                                       
CONECT   21   20   11   15                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₆

Average Mass

290.2710 Da

Monoisotopic Mass

290.07904 Da

IUPAC Name

(1S,4R,7S,12S)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1^{4,7}.0^{1,13}.0^{7,11}]heptadeca-5,10-diene-9,15-dione

Traditional Name

(1S,4R,7S,12S)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1^{4,7}.0^{1,13}.0^{7,11}]heptadeca-5,10-diene-9,15-dione

CAS Registry Number

Not Available

SMILES

CC1=C[C@@]23O[C@@H]1CC[C@]14OC1[C@@H](OC4=O)C2=C(C)C(=O)O3

InChI Identifier

InChI=1S/C15H14O6/c1-6-5-15-9(7(2)12(16)21-15)10-11-14(20-11,13(17)18-10)4-3-8(6)19-15/h5,8,10-11H,3-4H2,1-2H3/t8-,10+,11?,14+,15+/m1/s1

InChI Key

RRNMDHLOLUUHIK-ABZZKLJDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Neolitsea aciculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Gamma butyrolactone
Dicarboxylic acid or derivatives
2-furanone
Para-dioxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	0.85	ALOGPS
logP	1.8	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.11 m³·mol⁻¹	ChemAxon
Polarizability	27.24 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

162821311

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione (NP0141477)

MOL for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

3D MOL for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

3D SDF for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

3D-SDF for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

PDB for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

3D PDB for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

SMILES for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

INCHI for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

Structure for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)

3D Structure for NP0141477 ((1s,4r,7s,12s)-5,10-dimethyl-8,14,16,17-tetraoxapentacyclo[10.2.2.1⁴,⁷.0¹,¹³.0⁷,¹¹]heptadeca-5,10-diene-9,15-dione)