NP-MRD: Showing NP-Card for (1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid (NP0219094)

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Record Information

Version

2.0

Created at

2022-09-05 19:58:39 UTC

Updated at

2022-09-05 19:58:39 UTC

NP-MRD ID

NP0219094

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid

Description

3-Oxo-2,19alpha,22alpha-trihydroxy-24-norurs-1,4,12-triene-28-oic acid belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Based on a literature review very few articles have been published on 3-Oxo-2,19alpha,22alpha-trihydroxy-24-norurs-1,4,12-triene-28-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052221582D          

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M  END

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M  END


  Mrv1652309052221582D          

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 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  1  0  0  0
 13 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
  8 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219094

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](O)[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C=C(O)C(=O)C(C)=C5CC[C@@]34C)[C@@H]2[C@]1(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O6/c1-15-13-21(31)29(24(33)34)12-11-26(4)18(23(29)28(15,6)35)7-8-20-25(3)14-19(30)22(32)16(2)17(25)9-10-27(20,26)5/h7,14-15,20-21,23,30-31,35H,8-13H2,1-6H3,(H,33,34)/t15-,20-,21+,23-,25+,26-,27-,28-,29-/m1/s1

> <INCHI_KEY>
NCWRZLRFPGSMMS-GJBWZMOUSA-N

> <FORMULA>
C29H40O6

> <MOLECULAR_WEIGHT>
484.633

> <EXACT_MASS>
484.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.53229849285758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,4aS,6aS,6bR,12aS,12bS,14bS)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,10,12a,12b,13,14b-hexadecahydropicene-4a-carboxylic acid

> <JCHEM_LOGP>
3.4071499356666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.845747398800215

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.54112321157139

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0403267010590493

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
135.16530000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,4aS,6aS,6bR,12aS,12bS,14bS)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.206  -5.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874  -5.803   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -5.803   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.954  -5.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.574  -5.803   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.804  -4.469   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.114  -5.803   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.034  -5.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.494  -5.803   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.885  -5.605   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.751  -6.510   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.114 -11.137   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.750 -11.343   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.498 -10.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.644  -9.804   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   19                                             
CONECT    7    6                                                            
CONECT    8    6    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12   14   17   21                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11    6   20                                             
CONECT   20   19                                                            
CONECT   21   13   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   12   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    8    3   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
3-oxo-2,19a,22a-Trihydroxy-24-norurs-1,4,12-triene-28-Oate	Generator
3-oxo-2,19a,22a-Trihydroxy-24-norurs-1,4,12-triene-28-Oic acid	Generator
3-oxo-2,19alpha,22alpha-Trihydroxy-24-norurs-1,4,12-triene-28-Oate	Generator
3-oxo-2,19Α,22α-trihydroxy-24-norurs-1,4,12-triene-28-Oate	Generator
3-oxo-2,19Α,22α-trihydroxy-24-norurs-1,4,12-triene-28-Oic acid	Generator

Chemical Formula

C₂₉H₄₀O₆

Average Mass

484.6330 Da

Monoisotopic Mass

484.28249 Da

IUPAC Name

(1R,2R,4S,4aS,6aS,6bR,12aS,12bS,14bS)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,10,12a,12b,13,14b-hexadecahydropicene-4a-carboxylic acid

Traditional Name

(1R,2R,4S,4aS,6aS,6bR,12aS,12bS,14bS)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](O)[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C=C(O)C(=O)C(C)=C5CC[C@@]34C)[C@@H]2[C@]1(C)O)C(O)=O

InChI Identifier

InChI=1S/C29H40O6/c1-15-13-21(31)29(24(33)34)12-11-26(4)18(23(29)28(15,6)35)7-8-20-25(3)14-19(30)22(32)16(2)17(25)9-10-27(20,26)5/h7,14-15,20-21,23,30-31,35H,8-13H2,1-6H3,(H,33,34)/t15-,20-,21+,23-,25+,26-,27-,28-,29-/m1/s1

InChI Key

NCWRZLRFPGSMMS-GJBWZMOUSA-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 beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Cyclic alcohol
Tertiary alcohol
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Enol
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	3.41	ChemAxon
pKa (Strongest Acidic)	4.54	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	135.17 m³·mol⁻¹	ChemAxon
Polarizability	53.53 Å³	ChemAxon
Number of Rings	5	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

9765940

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11591177

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid (NP0219094)

MOL for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

3D MOL for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

3D SDF for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

3D-SDF for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

PDB for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

3D PDB for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

SMILES for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

INCHI for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

Structure for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)

3D Structure for NP0219094 ((1r,2r,4s,4as,6as,6br,12as,12bs,14bs)-1,4,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-oxo-2,3,4,5,6,7,8,12b,13,14b-decahydropicene-4a-carboxylic acid)