NP-MRD: Showing NP-Card for (1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one (NP0155614)

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Record Information

Version

2.0

Created at

2022-09-02 12:42:16 UTC

Updated at

2022-09-02 12:42:17 UTC

NP-MRD ID

NP0155614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one

Description

202522-40-5 Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one is found in Vernonanthura squamulosa. Based on a literature review very few articles have been published on 202522-40-5.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022214422D          

 24 26  0  0  1  0            999 V2000
    7.6573   -1.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323   -1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214   -0.9133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5964   -0.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855   -0.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652   -0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5836    1.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633    1.3409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5936    2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480    0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8804   -0.6303    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1650   -1.0412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    0.2449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923   -1.1837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7769   -1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620   -1.9911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -0.8609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6398   -1.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109    1.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227    0.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    0.7266    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0155614

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOCC1=C2[C@@H](O)C[C@@](C)(O)[C@]3(O)CC[C@@](C)(O3)\C=C2\OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O7/c1-4-22-9-10-13-11(18)7-16(3,20)17(21)6-5-15(2,24-17)8-12(13)23-14(10)19/h8,11,18,20-21H,4-7,9H2,1-3H3/b12-8+/t11-,15+,16+,17-/m0/s1

> <INCHI_KEY>
NQJAGJJBDQOCPP-WYMINXBFSA-N

> <FORMULA>
C17H24O7

> <MOLECULAR_WEIGHT>
340.372

> <EXACT_MASS>
340.152203113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.5266597575949

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,8S,10R,11S)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-5-one

> <ALOGPS_LOGP>
0.15

> <JCHEM_LOGP>
-0.43091798233333334

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.72253788078934

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.972606666031483

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1086497835912414

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
86.16239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,10R,11S)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-5-one

> <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      14.294  -3.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.754  -3.040   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.987  -1.705   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.447  -1.701   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.680  -0.366   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.148  -0.202   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.832   1.306   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.689   2.339   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.158   2.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.841   4.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.823   1.736   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.193   0.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.510  -1.177   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.175  -1.944   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.794   0.457   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.652  -2.210   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.317  -2.977   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.969  -3.717   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.183  -2.374   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.519  -1.607   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.661  -2.640   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.167   2.073   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.309   1.039   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.816   1.356   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13    9                                                       
CONECT   16   13   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19    6   21                                                  
CONECT   21   20                                                            
CONECT   22    7   23                                                       
CONECT   23   22    5   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₇

Average Mass

340.3720 Da

Monoisotopic Mass

340.15220 Da

IUPAC Name

(1R,8S,10R,11S)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-5-one

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCOCC1=C2[C@@H](O)C[C@@](C)(O)[C@]3(O)CC[C@@](C)(O3)\C=C2\OC1=O

InChI Identifier

InChI=1S/C17H24O7/c1-4-22-9-10-13-11(18)7-16(3,20)17(21)6-5-15(2,24-17)8-12(13)23-14(10)19/h8,11,18,20-21H,4-7,9H2,1-3H3/b12-8+/t11-,15+,16+,17-/m0/s1

InChI Key

NQJAGJJBDQOCPP-WYMINXBFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vernonanthura squamulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Enol ester
Tertiary alcohol
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Polyol
Oxacycle
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
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	0.15	ALOGPS
logP	-0.43	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.97	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.16 m³·mol⁻¹	ChemAxon
Polarizability	34.53 Å³	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

62895358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15381647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one (NP0155614)

MOL for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

3D MOL for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

3D SDF for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

3D-SDF for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

PDB for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

3D PDB for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

SMILES for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

INCHI for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

Structure for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)

3D Structure for NP0155614 ((1r,2e,8s,10r,11s)-6-(ethoxymethyl)-8,10,11-trihydroxy-1,10-dimethyl-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-2,6-dien-5-one)