NP-MRD: Showing NP-Card for (2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid (NP0330996)

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Record Information

Version

1.0

Created at

2022-09-12 16:53:37 UTC

Updated at

2022-09-12 16:53:37 UTC

NP-MRD ID

NP0330996

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid

Description

It was first documented in 2022 (PMID: 36130844). Based on a literature review a significant number of articles have been published on (2R,4aS,6aS,12bR,14aS,14bS)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2,9-dicarboxylic acid (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840) (PMID: 36130836) (PMID: 36130839).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218532D          

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  Mrv1652309122218532D          

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  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 12 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  1  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@](C)(C[C@@H]1[C@]1(C)CC[C@@]3(C)C4=C(C(=O)C=C3[C@@]1(C)CC2)C(C(O)=O)=C(O)C(O)=C4)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O7/c1-25-6-7-26(2,24(35)36)14-19(25)29(5)11-9-27(3)15-12-17(31)22(32)21(23(33)34)20(15)16(30)13-18(27)28(29,4)10-8-25/h12-13,19,31-32H,6-11,14H2,1-5H3,(H,33,34)(H,35,36)/t19-,25+,26+,27-,28+,29-/m0/s1

> <INCHI_KEY>
IGEUWSSSLAVCIX-HTKZLECJSA-N

> <FORMULA>
C29H36O7

> <MOLECULAR_WEIGHT>
496.6

> <EXACT_MASS>
496.246103499

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.865253133631555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aS,6aS,12bR,14aS,14bS)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2,9-dicarboxylic acid

> <JCHEM_LOGP>
5.913038753333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.487182767261961

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4953049225834025

> <JCHEM_PKA_STRONGEST_BASIC>
-6.6537966965731465

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
134.50369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aS,6aS,12bR,14aS,14bS)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -6.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.898  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.128  -6.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.588  -6.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.818  -5.184   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.048  -6.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.278  -5.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.508  -6.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.032  -6.517   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.802  -7.851   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.802  -5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.032  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.802  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.342  -2.516   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.112  -1.183   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.112  -3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.652  -3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.342  -5.184   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.112  -6.517   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.342  -7.851   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.652  -6.517   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.508  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.262  -2.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.278  -2.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.818  -2.516   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.588  -3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.358  -2.516   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.128  -3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.898  -2.516   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.438  -2.516   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.171  -1.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.886  -1.990   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -10.065  -2.980   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -9.153  -0.473   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.208  -3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.438  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28   36                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   26                                             
CONECT    6    5                                                            
CONECT    7    5    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   12    7   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   27   28                                             
CONECT   27   26                                                            
CONECT   28   26    2   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32   35                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   36                                                       
CONECT   36   35    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2R,4AS,6as,12BR,14as,14BS)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2,9-dicarboxylate	Generator

Chemical Formula

C₂₉H₃₆O₇

Average Mass

496.6000 Da

Monoisotopic Mass

496.24610 Da

IUPAC Name

(2R,4aS,6aS,12bR,14aS,14bS)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2,9-dicarboxylic acid

Traditional Name

(2R,4aS,6aS,12bR,14aS,14bS)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@](C)(C[C@@H]1[C@]1(C)CC[C@@]3(C)C4=C(C(=O)C=C3[C@@]1(C)CC2)C(C(O)=O)=C(O)C(O)=C4)C(O)=O

InChI Identifier

InChI=1S/C29H36O7/c1-25-6-7-26(2,24(35)36)14-19(25)29(5)11-9-27(3)15-12-17(31)22(32)21(23(33)34)20(15)16(30)13-18(27)28(29,4)10-8-25/h12-13,19,31-32H,6-11,14H2,1-5H3,(H,33,34)(H,35,36)/t19-,25+,26+,27-,28+,29-/m0/s1

InChI Key

IGEUWSSSLAVCIX-HTKZLECJSA-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

Classification

Not classified

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	5.91	ChemAxon
pKa (Strongest Acidic)	2.5	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	134.5 m³·mol⁻¹	ChemAxon
Polarizability	53.87 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

162911260

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
Yu H, Cai G, Wu J, Li Q: Clinical Phenotypic Variability and Significance of Pneumolabyrinth After Tympanum-Penetrating Injury. Ear Nose Throat J. 2022 Sep 21:1455613221128132. doi: 10.1177/01455613221128132. [PubMed:36130836 ]
Silverman A, Beres S: Child Neurology: Horner Syndrome in an Otherwise Well-Appearing Infant. Neurology. 2022 Sep 21. pii: WNL.0000000000201377. doi: 10.1212/WNL.0000000000201377. [PubMed:36130839 ]
Harada Y, Wang SH, Juel VC: Clinical Reasoning: A 36-Year-Old Man With Asymmetric Muscle Weakness. Neurology. 2022 Sep 21. pii: WNL.0000000000201379. doi: 10.1212/WNL.0000000000201379. [PubMed:36130838 ]
Guest O, Memon AA, Chukweubuka A, Zaheer M, Siddiqi N: Robotic low anterior resection for locally advanced rectal cancer - A video vignette. Colorectal Dis. 2022 Sep 21. doi: 10.1111/codi.16345. [PubMed:36130837 ]
Pellicori P, Kalra PR, Clark AL, Friday JM, Cleland JGF: Chronic kidney disease (CKD) and CKD-ism in heart failure - what a mess! Eur J Heart Fail. 2022 Sep 21. doi: 10.1002/ejhf.2696. [PubMed:36130835 ]
LOTUS database [Link]

Showing NP-Card for (2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid (NP0330996)

MOL for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

3D MOL for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

3D SDF for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

3D-SDF for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

PDB for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

3D PDB for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

SMILES for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

INCHI for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

Structure for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)

3D Structure for NP0330996 ((2r,4as,6as,12br,14as,14bs)-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2,9-dicarboxylic acid)