NP-MRD: Showing NP-Card for 7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione (NP0224862)

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Record Information

Version

2.0

Created at

2022-09-06 03:24:54 UTC

Updated at

2022-09-06 03:24:54 UTC

NP-MRD ID

NP0224862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione

Description

Fruticulin A belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione is found in Salvia corrugata and Salvia fruticulosa. 7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione was first documented in 2010 (PMID: 20683904). Based on a literature review a small amount of articles have been published on Fruticulin A (PMID: 25435893) (PMID: 24120298) (PMID: 19682878).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205242D          

 24 26  0  0  0  0            999 V2000
    6.2673    1.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    0.8219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742    1.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578    2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530    2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366    3.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    2.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733    0.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014    1.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.8219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    2.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753    1.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5541    3.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226    2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390    3.5528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109    2.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    3.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    3.1503    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=C2CC=C3C(O)=C(C(C)C)C(=O)C(=O)C3=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O4/c1-10(2)17-18(21)15-6-5-14-11(3)7-13(24-4)8-12(14)9-16(15)19(22)20(17)23/h6-10,21H,5H2,1-4H3

> <INCHI_KEY>
NZMUXZBQDVLKSD-UHFFFAOYSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.376

> <EXACT_MASS>
324.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.64007232068868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-14-methoxy-12-methyl-6-(propan-2-yl)tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione

> <JCHEM_LOGP>
4.128291950666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.35184068939217

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.144165810181126

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8278548964632515

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
95.7731

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0^{3,8}]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      11.699   1.988   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.227   1.534   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.099   2.582   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.441   4.083   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.312   5.130   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.655   6.632   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.841   4.677   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.498   3.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.627   2.128   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.111   2.507   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.723   3.175   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.594   2.128   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.937   0.626   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.123   2.582   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.006   1.534   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.780   4.083   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.692   4.537   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.821   3.489   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.034   6.038   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.909   5.130   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.566   6.632   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.380   4.677   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.341   5.881   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.881   5.881   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   11   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    7                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Fruticuline a	MeSH

Chemical Formula

C₂₀H₂₀O₄

Average Mass

324.3760 Da

Monoisotopic Mass

324.13616 Da

IUPAC Name

7-hydroxy-14-methoxy-12-methyl-6-(propan-2-yl)tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione

Traditional Name

7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0^{3,8}]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C2CC=C3C(O)=C(C(C)C)C(=O)C(=O)C3=CC2=C1

InChI Identifier

InChI=1S/C20H20O4/c1-10(2)17-18(21)15-6-5-14-11(3)7-13(24-4)8-12(14)9-16(15)19(22)20(17)23/h6-10,21H,5H2,1-4H3

InChI Key

NZMUXZBQDVLKSD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia corrugata	LOTUS Database	35616633
Salvia fruticulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anisole
Cyclohexenone
Alkyl aryl ether
Vinylogous acid
Cyclic ketone
Ketone
Ether
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	4.13	ChemAxon
pKa (Strongest Acidic)	5.14	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.77 m³·mol⁻¹	ChemAxon
Polarizability	35.64 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

321392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

362046

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Piccinelli AC, Figueiredo de Santana Aquino D, Morato PN, Kuraoka-Oliveira AM, Strapasson RL, Dos Santos EP, Stefanello ME, Oliveira RJ, Kassuya CA: Anti-Inflammatory and Antihyperalgesic Activities of Ethanolic Extract and Fruticulin A from Salvia lachnostachys Leaves in Mice. Evid Based Complement Alternat Med. 2014;2014:835914. doi: 10.1155/2014/835914. Epub 2014 Nov 10. [PubMed:25435893 ]
Giacomelli E, Bertrand S, Nievergelt A, Zwick V, Simoes-Pires C, Marcourt L, Rivara-Minten E, Cuendet M, Bisio A, Wolfender JL: Cancer chemopreventive diterpenes from Salvia corrugata. Phytochemistry. 2013 Dec;96:257-64. doi: 10.1016/j.phytochem.2013.09.011. Epub 2013 Oct 10. [PubMed:24120298 ]
Monticone M, Bisio A, Daga A, Giannoni P, Giaretti W, Maffei M, Pfeffer U, Romeo F, Quarto R, Romussi G, Corte G, Castagnola P: Demethyl fruticulin A (SCO-1) causes apoptosis by inducing reactive oxygen species in mitochondria. J Cell Biochem. 2010 Dec 1;111(5):1149-59. doi: 10.1002/jcb.22801. [PubMed:20683904 ]
Giannoni P, Narcisi R, De Totero D, Romussi G, Quarto R, Bisio A: The administration of demethyl fruticulin A from Salvia corrugata to mammalian cells lines induces "anoikis", a special form of apoptosis. Phytomedicine. 2010 May;17(6):449-56. doi: 10.1016/j.phymed.2009.07.007. Epub 2009 Aug 13. [PubMed:19682878 ]
LOTUS database [Link]

Showing NP-Card for 7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione (NP0224862)

MOL for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

3D MOL for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

3D SDF for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

3D-SDF for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

PDB for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

3D PDB for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

SMILES for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

INCHI for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

Structure for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)

3D Structure for NP0224862 (7-hydroxy-6-isopropyl-14-methoxy-12-methyltricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,6,8,11,13-hexaene-4,5-dione)