NP-MRD: Showing NP-Card for methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate (NP0248244)

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Record Information

Version

2.0

Created at

2022-09-07 10:25:15 UTC

Updated at

2022-09-07 10:25:15 UTC

NP-MRD ID

NP0248244

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate

Description

Methyl (2S,3R,4aR,12bS,14aS,14bS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,2,3,4,4a,5,11,12b,13,14,14a,14b-dodecahydropicene-2-carboxylate belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone. methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate is found in Orthosphenia mexicana and Peritassa campestris. Based on a literature review very few articles have been published on methyl (2S,3R,4aR,12bS,14aS,14bS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,2,3,4,4a,5,11,12b,13,14,14a,14b-dodecahydropicene-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072212252D          

 36 40  0  0  1  0            999 V2000
    1.3637   -1.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2205   -2.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -2.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4733   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309072212252D          

 36 40  0  0  1  0            999 V2000
    1.3637   -1.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0248244

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)C[C@H]2[C@]3(C)CC[C@@]4(C)C5=CC(=O)C(O)=C(C)C5=CC=C4C3=C(C)C[C@@]2(C)C(=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O6/c1-15-13-29(5)21(14-30(6,26(35)36-7)25(34)24(29)33)28(4)11-10-27(3)18(22(15)28)9-8-17-16(2)23(32)20(31)12-19(17)27/h8-9,12,21,25,32,34H,10-11,13-14H2,1-7H3/t21-,25-,27+,28-,29+,30-/m0/s1

> <INCHI_KEY>
JBKXDADFFNVBTG-ZYWUOJASSA-N

> <FORMULA>
C30H36O6

> <MOLECULAR_WEIGHT>
492.612

> <EXACT_MASS>
492.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.83336595611618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3R,4aR,12bS,14aS,14bS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,2,3,4,4a,5,11,12b,13,14,14a,14b-dodecahydropicene-2-carboxylate

> <JCHEM_LOGP>
3.6316607266666683

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.708959249822165

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.726206711567826

> <JCHEM_PKA_STRONGEST_BASIC>
-3.473819218898968

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
140.20350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3R,4aR,12bS,14aS,14bS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.546  -3.576   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.278  -5.093   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.831  -5.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.349  -4.630   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  C   UNK     0      -0.883  -6.610   0.000  0.00  0.00           C+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       3.644  -7.136   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.114  -5.803   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.114 -11.137   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.184  -9.804   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       5.184 -12.471   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.874 -11.137   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       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   35                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   11   27                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   26                                             
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   13   27                                                  
CONECT   27   26    9   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30    8   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    5   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S,3R,4ar,12BS,14as,14BS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,2,3,4,4a,5,11,12b,13,14,14a,14b-dodecahydropicene-2-carboxylic acid	Generator

Chemical Formula

C₃₀H₃₆O₆

Average Mass

492.6120 Da

Monoisotopic Mass

492.25119 Da

IUPAC Name

methyl (2S,3R,4aR,12bS,14aS,14bS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,2,3,4,4a,5,11,12b,13,14,14a,14b-dodecahydropicene-2-carboxylate

Traditional Name

methyl (2S,3R,4aR,12bS,14aS,14bS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)C[C@H]2[C@]3(C)CC[C@@]4(C)C5=CC(=O)C(O)=C(C)C5=CC=C4C3=C(C)C[C@@]2(C)C(=O)[C@@H]1O

InChI Identifier

InChI=1S/C30H36O6/c1-15-13-29(5)21(14-30(6,26(35)36-7)25(34)24(29)33)28(4)11-10-27(3)18(22(15)28)9-8-17-16(2)23(32)20(31)12-19(17)27/h8-9,12,21,25,32,34H,10-11,13-14H2,1-7H3/t21-,25-,27+,28-,29+,30-/m0/s1

InChI Key

JBKXDADFFNVBTG-ZYWUOJASSA-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
Orthosphenia mexicana	LOTUS Database	35616633
Peritassa campestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

3-hydroxysteroids

Alternative Parents

Substituents

3-hydroxysteroid
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Methyl ester
Carboxylic acid ester
Cyclic ketone
Ketone
Secondary alcohol
Enol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
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	3.63	ChemAxon
pKa (Strongest Acidic)	9.73	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	140.2 m³·mol⁻¹	ChemAxon
Polarizability	54.83 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

10191000

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21579199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate (NP0248244)

MOL for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

3D MOL for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

3D SDF for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

3D-SDF for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

PDB for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

3D PDB for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

SMILES for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

INCHI for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

Structure for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)

3D Structure for NP0248244 (methyl (2s,3r,4ar,12bs,14as,14bs)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-4,11-dioxo-1,3,5,13,14,14b-hexahydropicene-2-carboxylate)