NP-MRD: Showing NP-Card for (3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione (NP0218554)

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Record Information

Version

2.0

Created at

2022-09-05 19:15:13 UTC

Updated at

2022-09-05 19:15:13 UTC

NP-MRD ID

NP0218554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione

Description

(3S,6R,7S,10S,11R)-7-hydroxy-3,10,14-trimethyl-6-(propan-2-yl)tricyclo[9.3.0.0³,⁷]Tetradec-1(14)-ene-4,9-dione belongs to the class of organic compounds known as fusicoccane diterpenoids. These are diterpenoids with a structure based on a 20-carbon dicyclopenta[a,d]cyclooctane skeleton (5->8->5 ring system) known as fusicoccane. Based on a literature review very few articles have been published on (3S,6R,7S,10S,11R)-7-hydroxy-3,10,14-trimethyl-6-(propan-2-yl)tricyclo[9.3.0.0³,⁷]Tetradec-1(14)-ene-4,9-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221152D          

 23 25  0  0  1  0            999 V2000
    1.1157    0.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -0.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -0.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -0.9873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0736   -0.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7653    0.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -1.6848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8766   -2.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6878   -2.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -1.7495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0033   -2.4169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -3.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -2.5117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0949   -3.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -1.7495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5401   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -0.8826    0.0000 C   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
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21  3  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC(=O)[C@@]2(C)CC3=C(C)CC[C@@H]3[C@H](C)C(=O)C[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-11(2)16-8-18(22)19(5)9-15-12(3)6-7-14(15)13(4)17(21)10-20(16,19)23/h11,13-14,16,23H,6-10H2,1-5H3/t13-,14+,16+,19+,20-/m0/s1

> <INCHI_KEY>
FDQSYXUCFFFBAK-LEBLXQRQSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.521502437742626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6R,7S,10S,11R)-7-hydroxy-3,10,14-trimethyl-6-(propan-2-yl)tricyclo[9.3.0.0^{3,7}]tetradec-1(14)-ene-4,9-dione

> <JCHEM_LOGP>
3.5937936146666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.175425283981692

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.782739814206423

> <JCHEM_PKA_STRONGEST_BASIC>
-3.329693132723616

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
91.11149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R,7S,10S,11R)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0^{3,7}]tetradec-1(14)-ene-4,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.083   0.692   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.962  -0.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.133  -1.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.556  -1.254   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.978  -1.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.737  -0.322   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.149  -0.843   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.028   0.692   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.462  -1.647   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.103  -3.145   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.103  -4.316   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.617  -4.035   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.589  -5.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.568  -3.266   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.473  -4.512   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.978  -4.688   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.556  -5.278   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.556  -6.818   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.133  -4.688   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.044  -5.777   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.543  -3.266   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.008  -3.145   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.649  -1.647   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10    5   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4570 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(3S,6R,7S,10S,11R)-7-hydroxy-3,10,14-trimethyl-6-(propan-2-yl)tricyclo[9.3.0.0^{3,7}]tetradec-1(14)-ene-4,9-dione

Traditional Name

(3S,6R,7S,10S,11R)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0^{3,7}]tetradec-1(14)-ene-4,9-dione

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC(=O)[C@@]2(C)CC3=C(C)CC[C@@H]3[C@H](C)C(=O)C[C@]12O

InChI Identifier

InChI=1S/C20H30O3/c1-11(2)16-8-18(22)19(5)9-15-12(3)6-7-14(15)13(4)17(21)10-20(16,19)23/h11,13-14,16,23H,6-10H2,1-5H3/t13-,14+,16+,19+,20-/m0/s1

InChI Key

FDQSYXUCFFFBAK-LEBLXQRQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fusicoccane diterpenoids. These are diterpenoids with a structure based on a 20-carbon dicyclopenta[a,d]cyclooctane skeleton (5->8->5 ring system) known as fusicoccane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Fusicoccane diterpenoids

Alternative Parents

Substituents

Fusicoccane diterpenoid
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	3.59	ChemAxon
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.11 m³·mol⁻¹	ChemAxon
Polarizability	36.52 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

162890496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione (NP0218554)

MOL for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

3D MOL for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

3D SDF for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

3D-SDF for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

PDB for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

3D PDB for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

SMILES for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

INCHI for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

Structure for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)

3D Structure for NP0218554 ((3s,6r,7s,10s,11r)-7-hydroxy-6-isopropyl-3,10,14-trimethyltricyclo[9.3.0.0³,⁷]tetradec-1(14)-ene-4,9-dione)