NP-MRD: Showing NP-Card for 10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one (NP0325529)

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Record Information

Version

2.0

Created at

2022-09-12 06:20:58 UTC

Updated at

2022-09-12 06:20:59 UTC

NP-MRD ID

NP0325529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one

Description

10,14-Dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]Tetradec-6-en-5-one belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. 10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one is found in Smyrnium perfoliatum. 10,14-Dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]Tetradec-6-en-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171515452D          

 22 25  0  0  0  0            999 V2000
    1.7979   -0.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516   -0.7025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3115   -3.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509   -3.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC12CC3(C)C(O)C4OC4C(C)(O)C3CC1=C(C)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O6/c1-7-8-5-9-14(2,6-16(8,20-4)22-13(7)18)11(17)10-12(21-10)15(9,3)19/h9-12,17,19H,5-6H2,1-4H3

> <INCHI_KEY>
HUCZJKIJFGRTPM-UHFFFAOYSA-N

> <FORMULA>
C16H22O6

> <MOLECULAR_WEIGHT>
310.346

> <EXACT_MASS>
310.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.442919424304627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one

> <ALOGPS_LOGP>
0.37

> <JCHEM_LOGP>
0.6844173503333335

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.99658345925949

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.379490988778926

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3617730846191503

> <JCHEM_POLAR_SURFACE_AREA>
88.52

> <JCHEM_REFRACTIVITY>
75.58019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one

> <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       3.356  -0.685   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.763  -1.311   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591  -1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.592  -3.613   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.915  -6.333   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.935  -6.333   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.983  -6.323   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.014  -3.613   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.459  -2.367   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17   22                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7   15                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    9   12                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12    5   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂O₆

Average Mass

310.3460 Da

Monoisotopic Mass

310.14164 Da

IUPAC Name

10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one

Traditional Name

10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one

CAS Registry Number

Not Available

SMILES

COC12CC3(C)C(O)C4OC4C(C)(O)C3CC1=C(C)C(=O)O2

InChI Identifier

InChI=1S/C16H22O6/c1-7-8-5-9-14(2,6-16(8,20-4)22-13(7)18)11(17)10-12(21-10)15(9,3)19/h9-12,17,19H,5-6H2,1-4H3

InChI Key

HUCZJKIJFGRTPM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Smyrnium perfoliatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Ketal
Oxepane
2-furanone
Cyclic alcohol
Dihydrofuran
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
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	0.37	ALOGPS
logP	0.68	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.58 m³·mol⁻¹	ChemAxon
Polarizability	31.44 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one (NP0325529)

MOL for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

3D MOL for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

3D SDF for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

3D-SDF for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

PDB for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

3D PDB for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

SMILES for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

INCHI for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

Structure for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)

3D Structure for NP0325529 (10,14-dihydroxy-3-methoxy-1,6,10-trimethyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradec-6-en-5-one)