NP-MRD: Showing NP-Card for 10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid (NP0301654)

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Record Information

Version

2.0

Created at

2022-09-10 14:45:21 UTC

Updated at

2022-09-10 14:45:22 UTC

NP-MRD ID

NP0301654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid

Description

10,11-Dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,14,14a,14b-dodecahydropicene-2-carboxylic acid belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. 10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid is found in Celastrus orbiculatus and Tripterygium hypoglaucum. 10,11-Dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,14,14a,14b-dodecahydropicene-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518552D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004231518552D          

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  8 30  2  0  0  0  0
 16 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(O)=CC2=C1C=CC1(C)C2=CCC2(C)C3CC(C)(CCC3(C)CCC12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O4/c1-17-18-7-9-27(4)20(19(18)15-21(30)23(17)31)8-10-28(5)22-16-26(3,24(32)33)12-11-25(22,2)13-14-29(27,28)6/h7-9,15,22,30-31H,10-14,16H2,1-6H3,(H,32,33)

> <INCHI_KEY>
CBCMYJMFDLVEHM-UHFFFAOYSA-N

> <FORMULA>
C29H38O4

> <MOLECULAR_WEIGHT>
450.619

> <EXACT_MASS>
450.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.14824363989618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,14,14a,14b-dodecahydropicene-2-carboxylic acid

> <ALOGPS_LOGP>
6.65

> <JCHEM_LOGP>
6.7630191186666675

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.487231284929303

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.687588231325415

> <JCHEM_PKA_STRONGEST_BASIC>
-6.278684546557749

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
132.64210000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1H-picene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -0.206 -11.137   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.206  -5.803   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.076  -5.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.574 -11.137   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.023 -11.335   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.791  -6.610   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.058  -5.093   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.971  -7.600   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   24                                             
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   31                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   12   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    9   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    2    8                                                  
CONECT   31   16   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
10,11-Dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,14,14a,14b-dodecahydropicene-2-carboxylate	Generator

Chemical Formula

C₂₉H₃₈O₄

Average Mass

450.6190 Da

Monoisotopic Mass

450.27701 Da

IUPAC Name

10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,14,14a,14b-dodecahydropicene-2-carboxylic acid

Traditional Name

10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1H-picene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(O)=CC2=C1C=CC1(C)C2=CCC2(C)C3CC(C)(CCC3(C)CCC12C)C(O)=O

InChI Identifier

InChI=1S/C29H38O4/c1-17-18-7-9-27(4)20(19(18)15-21(30)23(17)31)8-10-28(5)22-16-26(3,24(32)33)12-11-25(22,2)13-14-29(27,28)6/h7-9,15,22,30-31H,10-14,16H2,1-6H3,(H,32,33)

InChI Key

CBCMYJMFDLVEHM-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
Celastrus orbiculatus	LOTUS Database	35616633
Tripterygium hypoglaucum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
2-naphthol
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	6.65	ALOGPS
logP	6.76	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.69	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.64 m³·mol⁻¹	ChemAxon
Polarizability	52.15 Å³	ChemAxon
Number of Rings	5	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

85122768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid (NP0301654)

MOL for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

3D MOL for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

3D SDF for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

3D-SDF for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

PDB for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

3D PDB for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

SMILES for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

INCHI for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

Structure for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)

3D Structure for NP0301654 (10,11-dihydroxy-2,4a,6a,6b,9,14a-hexamethyl-3,4,5,6,14,14b-hexahydro-1h-picene-2-carboxylic acid)