NP-MRD: Showing NP-Card for 12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione (NP0185685)

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Record Information

Version

2.0

Created at

2022-09-04 01:11:41 UTC

Updated at

2022-09-04 01:11:41 UTC

NP-MRD ID

NP0185685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione

Description

12,17-Dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]Hexacos-3-ene-7,22,26-trione belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. 12,17-Dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]Hexacos-3-ene-7,22,26-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171514582D          

 37 43  0  0  0  0            999 V2000
    5.9980    1.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6274    2.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 35  1  0  0  0  0
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 31 37  1  0  0  0  0
M  END

     RDKit          3D

 77 83  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004171514582D          

 37 43  0  0  0  0            999 V2000
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    1.9268    0.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7183   -0.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1844    0.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092    0.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4520   -0.2452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2509   -0.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8871   -0.5644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9951   -0.9930    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
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 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
 13 15  1  0  0  0  0
 13 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
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  2  0  0  0  0
 25 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CCC(C)(O)C3C4C5C6C(C(C)C5=O)(C5OC(=O)C(C)C5CCC6(C)O)C4C(C)=C3C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O7/c1-11-15-7-9-28(5,34)21-17(23(15)36-26(11)32)13(3)20-18(21)19-22(31)14(4)30(20)24(19)29(6,35)10-8-16-12(2)27(33)37-25(16)30/h11-12,14-16,18-21,23-25,34-35H,7-10H2,1-6H3

> <INCHI_KEY>
IZSZKQWJVIKEFE-UHFFFAOYSA-N

> <FORMULA>
C30H40O7

> <MOLECULAR_WEIGHT>
512.643

> <EXACT_MASS>
512.277403628

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.16940114701419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.122134556333333

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.020523934843997

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.411761661715346

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9125096213501145

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
133.82529999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      11.196   2.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.897   1.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.464   2.029   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.147   3.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.771   4.228   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.373   3.583   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.055   5.090   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.833   3.609   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.005   2.088   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.396   1.721   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.199   2.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.627   0.775   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.009   1.453   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.040   2.650   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.961   2.665   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.402   0.796   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.756  -0.703   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.804  -1.914   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.291  -3.375   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.759  -3.841   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.052  -4.290   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.063  -5.830   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.799  -3.394   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.264  -1.926   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.295  -0.729   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.930  -0.043   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.369  -0.869   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.887   1.497   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.467   2.229   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.597   0.032   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.074  -0.403   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.944   0.868   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.484   0.842   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.310  -0.458   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.802  -0.073   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.989  -1.054   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.591  -1.854   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   32                                                  
CONECT   10    9   11   30                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24   12   26   30                                             
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   11   29                                                  
CONECT   29   28                                                            
CONECT   30   25   10   31                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31    9   33                                                  
CONECT   33   32    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34    2   36                                                  
CONECT   36   35                                                            
CONECT   37   31                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₇

Average Mass

512.6430 Da

Monoisotopic Mass

512.27740 Da

IUPAC Name

12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione

Traditional Name

12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione

CAS Registry Number

Not Available

SMILES

CC1C2CCC(C)(O)C3C4C5C6C(C(C)C5=O)(C5OC(=O)C(C)C5CCC6(C)O)C4C(C)=C3C2OC1=O

InChI Identifier

InChI=1S/C30H40O7/c1-11-15-7-9-28(5,34)21-17(23(15)36-26(11)32)13(3)20-18(21)19-22(31)14(4)30(20)24(19)29(6,35)10-8-16-12(2)27(33)37-25(16)30/h11-12,14-16,18-21,23-25,34-35H,7-10H2,1-6H3

InChI Key

IZSZKQWJVIKEFE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
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	2.71	ALOGPS
logP	2.12	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.41	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	133.83 m³·mol⁻¹	ChemAxon
Polarizability	55.17 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

73657093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione (NP0185685)

MOL for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

3D MOL for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

3D SDF for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

3D-SDF for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

PDB for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

3D PDB for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

SMILES for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

INCHI for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

Structure for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)

3D Structure for NP0185685 (12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacos-3-ene-7,22,26-trione)