NP-MRD: Showing NP-Card for 4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol (NP0233770)

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Record Information

Version

2.0

Created at

2022-09-06 15:29:18 UTC

Updated at

2022-09-06 15:29:18 UTC

NP-MRD ID

NP0233770

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol

Description

4-(4-Hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1H,3H,4H,4aH,5H,6H,9H,10H,11H,11aH-cyclonona[c]pyran-1,9-diol belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. 4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol is found in Ovabunda macrospiculata. 4-(4-Hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1H,3H,4H,4aH,5H,6H,9H,10H,11H,11aH-cyclonona[c]pyran-1,9-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251506052D          

 24 25  0  0  0  0            999 V2000
    6.2734    2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6414    1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9236    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6414    0.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2734   -0.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9269   -0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697   -0.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    0.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    3.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    3.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4408    4.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7263    4.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533    5.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0283    3.6300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842    1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9269    2.2322    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  4  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  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  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 14 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233770

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)CC(=C)C2C(O)OCC(=CC=CC(C)(C)O)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-13-7-8-17-15(6-5-9-20(3,4)23)12-24-19(22)18(17)14(2)11-16(21)10-13/h5-6,9-10,16-19,21-23H,2,7-8,11-12H2,1,3-4H3

> <INCHI_KEY>
HGDULVKIUOELKF-UHFFFAOYSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.084444019134814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1H,3H,4H,4aH,5H,6H,9H,10H,11H,11aH-cyclonona[c]pyran-1,9-diol

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
1.9229640199999993

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.911535250193012

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.101513055666924

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1482880655334178

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
98.6987

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1H,3H,4aH,5H,6H,9H,10H,11aH-cyclonona[c]pyran-1,9-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      11.710   4.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.531   3.397   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.057   1.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.531   0.503   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.710  -0.487   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.197  -0.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.680  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.910  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.690   1.180   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.357   0.410   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.357  -1.130   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.023   1.180   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.023   2.720   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.357   3.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.357   5.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.023   5.800   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.023   7.340   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.689   8.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.356   8.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.459   9.443   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.919   6.776   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.690   2.720   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.680   3.899   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.197   4.167   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   22                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   14    9   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    2                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1H,3H,4H,4aH,5H,6H,9H,10H,11H,11aH-cyclonona[c]pyran-1,9-diol

Traditional Name

4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1H,3H,4aH,5H,6H,9H,10H,11aH-cyclonona[c]pyran-1,9-diol

CAS Registry Number

Not Available

SMILES

CC1=CC(O)CC(=C)C2C(O)OCC(=CC=CC(C)(C)O)C2CC1

InChI Identifier

InChI=1S/C20H30O4/c1-13-7-8-17-15(6-5-9-20(3,4)23)12-24-19(22)18(17)14(2)11-16(21)10-13/h5-6,9-10,16-19,21-23H,2,7-8,11-12H2,1,3-4H3

InChI Key

HGDULVKIUOELKF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ovabunda macrospiculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Tertiary alcohol
Secondary alcohol
Hemiacetal
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	2.28	ALOGPS
logP	1.92	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.7 m³·mol⁻¹	ChemAxon
Polarizability	38.08 Å³	ChemAxon
Number of Rings	2	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

73799051

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol (NP0233770)

MOL for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

3D MOL for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

3D SDF for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

3D-SDF for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

PDB for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

3D PDB for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

SMILES for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

INCHI for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

Structure for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)

3D Structure for NP0233770 (4-(4-hydroxy-4-methylpent-2-en-1-ylidene)-7-methyl-11-methylidene-1h,3h,4ah,5h,6h,9h,10h,11ah-cyclonona[c]pyran-1,9-diol)