NP-MRD: Showing NP-Card for 3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione (NP0057697)

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Record Information

Version

2.0

Created at

2022-04-28 03:06:44 UTC

Updated at

2022-04-28 03:06:44 UTC

NP-MRD ID

NP0057697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione

Description

(1R,2R,3R,7S,8S,10R)-3,10-dihydroxy-3,10-dimethyl-6,12-bis(propan-2-yl)tricyclo[6.2.2.0²,⁷]Dodeca-5,11-diene-4,9-dione belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione is found in Callitris macleayana. Based on a literature review very few articles have been published on (1R,2R,3R,7S,8S,10R)-3,10-dihydroxy-3,10-dimethyl-6,12-bis(propan-2-yl)tricyclo[6.2.2.0²,⁷]Dodeca-5,11-diene-4,9-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282205062D          

 24 26  0  0  1  0            999 V2000
    1.9969    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0794   -0.0825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7939   -0.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2110    1.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3572    1.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6679   -1.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -1.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9475   -1.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5680   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1577   -0.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2825    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1450    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215    0.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860    1.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498   -0.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3946    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1897    1.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  6  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 13 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
 16 23  1  0  0  0  0
 16 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0057697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC(=O)[C@](C)(O)[C@H]2[C@H]3C=C(C(C)C)[C@H]([C@@H]12)C(=O)[C@]3(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-9(2)11-7-13-17-15(16(11)18(22)19(13,5)23)12(10(3)4)8-14(21)20(17,6)24/h7-10,13,15-17,23-24H,1-6H3/t13-,15-,16-,17+,19-,20+/m1/s1

> <INCHI_KEY>
YNYHPBIGKWCFOA-WBUZRZPQSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
17.515873385594002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3R,7S,8S,10R)-3,10-dihydroxy-3,10-dimethyl-6,12-bis(propan-2-yl)tricyclo[6.2.2.0^{2,7}]dodeca-5,11-diene-4,9-dione

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
2.5398129210000007

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.272073255804195

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.5428450711917

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6722875736603484

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
94.03679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,7S,8S,10R)-3,10-dihydroxy-6,12-diisopropyl-3,10-dimethyltricyclo[6.2.2.0^{2,7}]dodeca-5,11-diene-4,9-dione

> <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       3.728   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.882  -0.154   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.215  -0.616   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.395   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.395   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.861   2.242   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.061   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.267   3.646   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.900   3.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.980  -2.447   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.321  -3.348   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.635  -3.345   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.394  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.060  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.294  -0.946   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.060   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.394   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.137   1.283   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.137   0.257   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.587   0.543   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.454   1.868   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.200  -1.181   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.737   1.748   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.354   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    7   17                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1    8    9                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23   24                                             
CONECT   17   16    1   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16                                                            
CONECT   24   16                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

(1R,2R,3R,7S,8S,10R)-3,10-dihydroxy-3,10-dimethyl-6,12-bis(propan-2-yl)tricyclo[6.2.2.0^{2,7}]dodeca-5,11-diene-4,9-dione

Traditional Name

(1R,2R,3R,7S,8S,10R)-3,10-dihydroxy-6,12-diisopropyl-3,10-dimethyltricyclo[6.2.2.0^{2,7}]dodeca-5,11-diene-4,9-dione

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC(=O)[C@](C)(O)[C@H]2[C@H]3C=C(C(C)C)[C@H]([C@@H]12)C(=O)[C@]3(C)O

InChI Identifier

InChI=1S/C20H28O4/c1-9(2)11-7-13-17-15(16(11)18(22)19(13,5)23)12(10(3)4)8-14(21)20(17,6)24/h7-10,13,15-17,23-24H,1-6H3/t13-,15-,16-,17+,19-,20+/m1/s1

InChI Key

YNYHPBIGKWCFOA-WBUZRZPQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Callitris macleayana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cyclohexenone
Acyloin
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.52	ALOGPS
logP	2.54	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.04 m³·mol⁻¹	ChemAxon
Polarizability	17.52 Å³	ChemAxon
Number of Rings	3	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

162882154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione (NP0057697)

MOL for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

3D MOL for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

3D SDF for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

3D-SDF for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

PDB for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

3D PDB for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

SMILES for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

INCHI for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

Structure for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)

3D Structure for NP0057697 (3,10-Dihydroxy-5,11-dielementhadiene-4,9-dione)