NP-MRD: Showing NP-Card for 17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one (NP0218236)

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Record Information

Version

2.0

Created at

2022-09-05 18:50:31 UTC

Updated at

2022-09-05 18:50:31 UTC

NP-MRD ID

NP0218236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one

Description

17-Hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]Nonadec-5-en-7-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one is found in Diplospora dubia. 17-Hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]Nonadec-5-en-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201501302D          

 24 28  0  0  0  0            999 V2000
    1.5709    1.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9760    0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898    1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148    1.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    0.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327    0.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5175   -0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2312   -0.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632   -0.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -0.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -0.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9815   -0.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1553   -1.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1103    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522    0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1462    1.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1341    0.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7588   -0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5347   -0.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -1.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6560   -1.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0205   -0.8451    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 14 24  1  0  0  0  0
M  END


  Mrv1533004201501302D          

 24 28  0  0  0  0            999 V2000
    1.5709    1.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9760    0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898    1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148    1.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    0.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327    0.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5175   -0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2312   -0.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632   -0.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -0.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -0.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9815   -0.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1553   -1.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1103    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522    0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1462    1.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1341    0.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7588   -0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5347   -0.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -1.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6560   -1.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0205   -0.8451    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 14 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3OC(=O)C=C3C1CCC13CC(CCC21)C(O)(CO)C3

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-18-6-5-15-13(8-17(22)24-15)14(18)4-7-19-9-12(2-3-16(18)19)20(23,10-19)11-21/h8,12,14-16,21,23H,2-7,9-11H2,1H3

> <INCHI_KEY>
GCGHKCGNVBKLKA-UHFFFAOYSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.73501699508251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
2.047105620666666

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.685427150174842

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.777946778476912

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0757507495330314

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
89.73599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       2.932   2.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.689   0.846   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.461   2.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.001   2.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.769   0.841   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.274   0.518   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.433  -1.014   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.765  -1.786   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.025  -1.638   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.996  -0.491   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.456  -0.489   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.699  -1.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.156  -1.868   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.286  -0.556   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.206   0.226   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.031   0.844   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.273   2.270   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.332   2.318   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.117   0.876   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.416  -0.720   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.865  -0.197   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.088  -2.106   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.224  -3.381   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.038  -1.578   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19   24                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    2   14                                                  
CONECT   20   16   21   22   24                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   20   14                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one

Traditional Name

17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one

CAS Registry Number

Not Available

SMILES

CC12CCC3OC(=O)C=C3C1CCC13CC(CCC21)C(O)(CO)C3

InChI Identifier

InChI=1S/C20H28O4/c1-18-6-5-15-13(8-17(22)24-15)14(18)4-7-19-9-12(2-3-16(18)19)20(23,10-19)11-21/h8,12,14-16,21,23H,2-7,9-11H2,1H3

InChI Key

GCGHKCGNVBKLKA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Diplospora dubia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Steroid
17-oxasteroid
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary 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	1.61	ALOGPS
logP	2.05	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.74 m³·mol⁻¹	ChemAxon
Polarizability	36.74 Å³	ChemAxon
Number of Rings	5	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

73023608

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one (NP0218236)

MOL for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

3D MOL for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

3D SDF for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

3D-SDF for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

PDB for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

3D PDB for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

SMILES for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

INCHI for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

Structure for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)

3D Structure for NP0218236 (17-hydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-5-en-7-one)