NP-MRD: Showing NP-Card for 12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde (NP0320443)

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Record Information

Version

2.0

Created at

2022-09-11 22:05:45 UTC

Updated at

2022-09-11 22:05:45 UTC

NP-MRD ID

NP0320443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde

Description

12-(5,6-Dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]Tetradeca-4,8-diene-8-carbaldehyde belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position. Based on a literature review very few articles have been published on 12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]Tetradeca-4,8-diene-8-carbaldehyde.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122200052D          

 29 31  0  0  0  0            999 V2000
    1.1157   -2.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -1.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -0.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    0.0099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -0.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949    0.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.5897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    0.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -0.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -0.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766    0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6878   -0.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012    0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1370    1.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8616    2.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3974    2.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505    2.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    2.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2008    3.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    1.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -1.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -1.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736   -2.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -1.3149    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  2  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
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  4  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 14  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END


  Mrv1652309122200052D          

 29 31  0  0  0  0            999 V2000
    1.1157   -2.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -1.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -0.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    0.0099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -0.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949    0.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.5897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    0.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -0.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -0.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766    0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6878   -0.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012    0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1370    1.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8616    2.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3974    2.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505    2.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    2.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2008    3.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    1.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -1.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -1.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736   -2.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -1.3149    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  2  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
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  4  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 14  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C=CC(O)C(C)(C)O)C1CCC2(C)CC3C(C(=O)C=C3C)C(C=O)=CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O4/c1-15(6-9-22(28)24(3,4)29)18-10-11-25(5)13-19-16(2)12-21(27)23(19)17(14-26)7-8-20(18)25/h6-7,9,12,14-15,18-20,22-23,28-29H,8,10-11,13H2,1-5H3

> <INCHI_KEY>
ZCYAUPOUCSSQGA-UHFFFAOYSA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.559

> <EXACT_MASS>
400.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.76390823441116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0^{3,7}]tetradeca-4,8-diene-8-carbaldehyde

> <JCHEM_LOGP>
3.5306766549999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.81938545550901

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.223932293577253

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1165399160996943

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
118.1191

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0^{3,7}]tetradeca-4,8-diene-8-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.083  -4.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.962  -3.455   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.649  -2.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.008  -1.153   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.008   0.018   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.543  -1.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.133   0.391   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.044   1.480   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.442   2.967   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.556   0.980   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.978   0.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.568  -1.032   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.103  -1.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.103   0.018   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.617  -0.262   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.589   1.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.589   2.641   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.075   4.093   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.075   5.264   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.561   4.373   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.047   4.654   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.841   5.888   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.280   2.859   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.462  -2.650   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.149  -3.455   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.978  -2.455   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.737  -3.976   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.556  -3.044   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.133  -2.455   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   29                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   12   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₄

Average Mass

400.5590 Da

Monoisotopic Mass

400.26136 Da

IUPAC Name

12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0^{3,7}]tetradeca-4,8-diene-8-carbaldehyde

Traditional Name

12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0^{3,7}]tetradeca-4,8-diene-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C=CC(O)C(C)(C)O)C1CCC2(C)CC3C(C(=O)C=C3C)C(C=O)=CCC12

InChI Identifier

InChI=1S/C25H36O4/c1-15(6-9-22(28)24(3,4)29)18-10-11-25(5)13-19-16(2)12-21(27)23(19)17(14-26)7-8-20(18)25/h6-7,9,12,14-15,18-20,22-23,28-29H,8,10-11,13H2,1-5H3

InChI Key

ZCYAUPOUCSSQGA-UHFFFAOYSA-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 ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Ophiobolane sesterterpenoids

Alternative Parents

Substituents

Ophiobolane sesterterpenoid
Tertiary alcohol
Secondary alcohol
Ketone
1,2-diol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	3.53	ChemAxon
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	-3.1	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	5	ChemAxon
Refractivity	118.12 m³·mol⁻¹	ChemAxon
Polarizability	45.76 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

162995365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde (NP0320443)

MOL for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

3D MOL for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

3D SDF for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

3D-SDF for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

PDB for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

3D PDB for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

SMILES for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

INCHI for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

Structure for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)

3D Structure for NP0320443 (12-(5,6-dihydroxy-6-methylhept-3-en-2-yl)-1,4-dimethyl-6-oxotricyclo[9.3.0.0³,⁷]tetradeca-4,8-diene-8-carbaldehyde)