NP-MRD: Showing NP-Card for 11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one (NP0328201)

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Record Information

Version

2.0

Created at

2022-09-12 11:27:33 UTC

Updated at

2022-09-12 11:27:34 UTC

NP-MRD ID

NP0328201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

Description

11,12-Dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]Tetracos-17-en-22-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one is found in Tripterygium wilfordii. 11,12-Dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]Tetracos-17-en-22-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181503462D          

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M  END

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M  END


  Mrv1533004181503462D          

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    3.0561   -2.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9503   -1.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2936   -0.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238   -0.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010   -0.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994   -1.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6293   -0.4695    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 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
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 25 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 14 33  1  0  0  0  0
 19 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(OC1=O)C1(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C)C5CCC34C)C1C2

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-25(2)20-10-11-30(7)21(28(20,5)15-19(31)23(25)32)9-8-17-18-14-26(3)16-22(34-24(26)33)27(18,4)12-13-29(17,30)6/h8,18-23,31-32H,9-16H2,1-7H3

> <INCHI_KEY>
RMZYLHSFNGKWCT-UHFFFAOYSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.109414546957744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
4.953589883999999

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.155801752111156

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.627313693012464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1598164618201103

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
133.0093

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -8.922  -2.033   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.464  -2.532   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.227  -1.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.208  -3.880   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -9.748  -3.910   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -7.412  -5.199   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.156  -6.547   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.872  -5.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.129  -3.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.333  -5.138   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.925  -2.501   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.181  -1.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.641  -1.123   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.845  -2.441   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.102  -1.093   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.589  -3.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.793  -5.108   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.253  -5.078   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.510  -3.729   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.030  -3.699   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.621  -5.121   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.101  -5.546   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.360  -7.064   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.628  -3.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.292  -2.091   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.441  -3.116   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.356  -4.654   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.705  -5.398   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.774  -2.350   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.415  -0.950   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.978  -1.032   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.562  -1.062   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.306  -2.411   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.175  -0.876   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   11                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   27                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   25   20   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   14   19   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

Traditional Name

11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

CAS Registry Number

Not Available

SMILES

CC12CC(OC1=O)C1(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C)C5CCC34C)C1C2

InChI Identifier

InChI=1S/C30H46O4/c1-25(2)20-10-11-30(7)21(28(20,5)15-19(31)23(25)32)9-8-17-18-14-26(3)16-22(34-24(26)33)27(18,4)12-13-29(17,30)6/h8,18-23,31-32H,9-16H2,1-7H3

InChI Key

RMZYLHSFNGKWCT-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

Species Name	Source	Reference
Tripterygium wilfordii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Caprolactone
Oxepane
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
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	5.38	ALOGPS
logP	4.95	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.63	ChemAxon
pKa (Strongest Basic)	-3.2	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	0	ChemAxon
Refractivity	133.01 m³·mol⁻¹	ChemAxon
Polarizability	55.11 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

73809772

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one (NP0328201)

MOL for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D MOL for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D SDF for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D-SDF for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

PDB for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D PDB for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

SMILES for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

INCHI for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

Structure for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D Structure for NP0328201 (11,12-dihydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)