NP-MRD: Showing NP-Card for (3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione (NP0159271)

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Record Information

Version

2.0

Created at

2022-09-02 17:00:02 UTC

Updated at

2022-09-02 17:00:03 UTC

NP-MRD ID

NP0159271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione

Description

Elisabanolide belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione is found in Antillogorgia elisabethae. (3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione was first documented in 1998 (PMID: 11672336). Based on a literature review very few articles have been published on elisabanolide (PMID: 10814100).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022219002D          

 23 26  0  0  1  0            999 V2000
    0.8466   -1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3330   -0.9854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0025   -0.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846    0.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076    0.3595    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8554    1.0346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6433    1.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6693    0.7198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2553    0.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1685   -1.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4625   -0.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3336   -1.7591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2852   -0.6723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2496   -1.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0433   -0.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2256   -1.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870   -0.3773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9141    0.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8996    1.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3604    0.1493    0.0000 C   0  0  1  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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 23 20  1  6  0  0  0
  8 23  1  0  0  0  0
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2CC3([C@@H]1CC[C@H](C)C3=O)C(=O)[C@]1(C)[C@H]2C(C)(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O4/c1-9-6-7-12-10(2)11-8-19(12,14(9)20)15(21)18(5)13(11)17(3,4)23-16(18)22/h9-13H,6-8H2,1-5H3/t9-,10-,11-,12+,13+,18-,19?/m0/s1

> <INCHI_KEY>
UXNTVDPSNWKYNJ-VCHANUIPSA-N

> <FORMULA>
C19H26O4

> <MOLECULAR_WEIGHT>
318.413

> <EXACT_MASS>
318.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.50113552481373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,7S,8S,9S,10R,13S)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0^{1,10}.0^{3,7}]pentadecane-2,4,14-trione

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
3.8662507823333323

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0332696883643635

> <JCHEM_POLAR_SURFACE_AREA>
60.44

> <JCHEM_REFRACTIVITY>
84.5918

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,7S,8S,9S,10R,13S)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0^{1,10}.0^{3,7}]pentadecane-2,4,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.580  -3.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.488  -1.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.871  -0.416   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.771   0.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.307   0.671   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.330   1.931   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.934   3.419   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.849   1.344   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.077   0.217   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.105  -0.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.048  -1.995   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.620  -3.425   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.463  -1.763   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.223  -3.284   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.999  -1.255   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.933  -2.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.414  -1.862   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.754  -3.364   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.429  -0.704   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.641   0.619   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.040   1.264   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.146   2.077   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.139   0.279   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11   13                                             
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20    8   15                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₄

Average Mass

318.4130 Da

Monoisotopic Mass

318.18311 Da

IUPAC Name

(3S,7S,8S,9S,10R,13S)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0^{1,10}.0^{3,7}]pentadecane-2,4,14-trione

Traditional Name

(3S,7S,8S,9S,10R,13S)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0^{1,10}.0^{3,7}]pentadecane-2,4,14-trione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2CC3([C@@H]1CC[C@H](C)C3=O)C(=O)[C@]1(C)[C@H]2C(C)(C)OC1=O

InChI Identifier

InChI=1S/C19H26O4/c1-9-6-7-12-10(2)11-8-19(12,14(9)20)15(21)18(5)13(11)17(3,4)23-16(18)22/h9-13H,6-8H2,1-5H3/t9-,10-,11-,12+,13+,18-,19?/m0/s1

InChI Key

UXNTVDPSNWKYNJ-VCHANUIPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Antillogorgia elisabethae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	2.8	ALOGPS
logP	3.87	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.59 m³·mol⁻¹	ChemAxon
Polarizability	34.5 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

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

15377595

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rodriguez AD, Ramirez C, Rodriguez II, Barnes CL: Novel terpenoids from the West Indian sea whip Pseudopterogorgia elisabethae (Bayer). Elisapterosins A and B: rearranged diterpenes possessing an unprecedented cagelike framework. J Org Chem. 2000 Mar 10;65(5):1390-8. doi: 10.1021/jo9914869. [PubMed:10814100 ]
Rodriguez AD, Gonzalez E, Huang SD: Unusual Terpenes with Novel Carbon Skeletons from the West Indian Sea Whip Pseudopterogorgia elisabethae (Octocorallia)(1). J Org Chem. 1998 Oct 2;63(20):7083-7091. doi: 10.1021/jo981385v. [PubMed:11672336 ]
LOTUS database [Link]

Showing NP-Card for (3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione (NP0159271)

MOL for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

3D MOL for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

3D SDF for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

3D-SDF for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

PDB for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

3D PDB for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

SMILES for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

INCHI for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

Structure for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)

3D Structure for NP0159271 ((3s,7s,8s,9s,10r,13s)-3,6,6,9,13-pentamethyl-5-oxatetracyclo[6.6.1.0¹,¹⁰.0³,⁷]pentadecane-2,4,14-trione)