NP-MRD: Showing NP-Card for 3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin (NP0063834)

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Record Information

Version

1.0

Created at

2022-04-28 08:10:30 UTC

Updated at

2022-04-28 08:10:30 UTC

NP-MRD ID

NP0063834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin

Description

(1S,3R,6S,7S,10S,13S)-13-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]Tetradec-11-en-8-one 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. 3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin is found in Artemisia adamsii. Based on a literature review very few articles have been published on (1S,3R,6S,7S,10S,13S)-13-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]Tetradec-11-en-8-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282210102D          

 19 22  0  0  1  0            999 V2000
   -0.0435   -1.2544    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7635   -1.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498   -0.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961    0.0732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4560   -0.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114    0.8716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3835    1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2081    1.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415    0.9270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5820    0.1175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3026   -0.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168    0.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606    1.0254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9624    1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6992    0.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3765   -1.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791   -2.0080    0.0000 O   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
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
  6 16  1  1  0  0  0
  6 17  1  0  0  0  0
  4 17  1  6  0  0  0
  2 18  1  0  0  0  0
  1 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0063834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2CC[C@@]3(C)O[C@]33C[C@H](O)C(C)=C3[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-7-9-4-5-14(3)15(19-14)6-10(16)8(2)11(15)12(9)18-13(7)17/h7,9-10,12,16H,4-6H2,1-3H3/t7-,9-,10-,12-,14+,15-/m0/s1

> <INCHI_KEY>
PSMFNVQGICNHHA-UYCONBJKSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.45695655695628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,6S,7S,10S,13S)-13-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-11-en-8-one

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
0.8750612583333333

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.473723859429612

> <JCHEM_PKA_STRONGEST_BASIC>
-3.028993183885488

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
68.06040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6S,7S,10S,13S)-13-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-11-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.081  -2.342   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.425  -2.021   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.586  -0.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.179   0.137   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.851  -1.008   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.208   1.627   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.716   2.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.255   2.905   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.251   1.730   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.953   0.219   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.298  -0.531   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.427   0.517   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.938   0.219   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.780   1.914   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.530   3.259   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.368   2.640   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.305   0.546   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.570  -3.052   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.708  -3.748   0.000  0.00  0.00           O+0
CONECT    1    2    5   19                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6   17                                             
CONECT    5    4    1                                                       
CONECT    6    4    7   16   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14                                                            
CONECT   16    6                                                            
CONECT   17    6    4                                                       
CONECT   18    2                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(1S,3R,6S,7S,10S,13S)-13-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-11-en-8-one

Traditional Name

(1S,3R,6S,7S,10S,13S)-13-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-11-en-8-one

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2CC[C@@]3(C)O[C@]33C[C@H](O)C(C)=C3[C@H]2OC1=O

InChI Identifier

InChI=1S/C15H20O4/c1-7-9-4-5-14(3)15(19-14)6-10(16)8(2)11(15)12(9)18-13(7)17/h7,9-10,12,16H,4-6H2,1-3H3/t7-,9-,10-,12-,14+,15-/m0/s1

InChI Key

PSMFNVQGICNHHA-UYCONBJKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia adamsii	Plant	KNApSAcK

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
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
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	1.24	ALOGPS
logP	0.88	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	14.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.06 m³·mol⁻¹	ChemAxon
Polarizability	28.46 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

163105566

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin (NP0063834)

MOL for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

3D MOL for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

3D SDF for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

3D-SDF for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

PDB for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

3D PDB for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

SMILES for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

INCHI for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

Structure for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)

3D Structure for NP0063834 (3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin)