NP-MRD: Showing NP-Card for (1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate (NP0210335)

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Record Information

Version

2.0

Created at

2022-09-05 08:05:36 UTC

Updated at

2022-09-05 08:05:36 UTC

NP-MRD ID

NP0210335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate

Description

SCHEMBL5934762 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate is found in Betula pendula. Based on a literature review very few articles have been published on SCHEMBL5934762.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210052D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052210052D          

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    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9702   -4.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0698   -1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2328   -2.4739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833    0.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4788    1.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    0.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  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  6  0  0  0
 27 28  1  6  0  0  0
 27 29  1  6  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 36 26  1  1  0  0  0
  5 36  1  0  0  0  0
 22 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210335

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@@]21C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H52O4/c1-20(2)11-10-15-32(9,35)22-12-17-31(8)27(22)23(36-21(3)33)19-25-29(6)16-14-26(34)28(4,5)24(29)13-18-30(25,31)7/h11,22-25,27,35H,10,12-19H2,1-9H3/t22-,23+,24-,25+,27-,29-,30+,31+,32-/m0/s1

> <INCHI_KEY>
KVXMPQFKQBICKI-UQVKNAHLSA-N

> <FORMULA>
C32H52O4

> <MOLECULAR_WEIGHT>
500.764

> <EXACT_MASS>
500.386560154

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
59.50147799362285

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,7R,10R,11R,14S,15R,16R)-14-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-16-yl acetate

> <JCHEM_LOGP>
6.5365909209999975

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.960996935135256

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.766072068445371

> <JCHEM_PKA_STRONGEST_BASIC>
-2.901118864592693

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
145.56510000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7R,10R,11R,14S,15R,16R)-14-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-16-yl acetate

> <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       6.244  -1.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.728  -1.036   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.205   0.413   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.735  -2.213   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.312  -7.735   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.678  -7.823   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.997  -2.728   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.435  -4.618   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.164  -2.457   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.416  -1.030   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.529   0.185   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.051   1.612   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.894   2.828   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.577   1.822   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   10   17                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    8   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    7   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   24   36                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   36                                                  
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   26    5   22                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₅₂O₄

Average Mass

500.7640 Da

Monoisotopic Mass

500.38656 Da

IUPAC Name

(1R,2R,7R,10R,11R,14S,15R,16R)-14-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-16-yl acetate

Traditional Name

(1R,2R,7R,10R,11R,14S,15R,16R)-14-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-16-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@@]21C)OC(C)=O

InChI Identifier

InChI=1S/C32H52O4/c1-20(2)11-10-15-32(9,35)22-12-17-31(8)27(22)23(36-21(3)33)19-25-29(6)16-14-26(34)28(4,5)24(29)13-18-30(25,31)7/h11,22-25,27,35H,10,12-19H2,1-9H3/t22-,23+,24-,25+,27-,29-,30+,31+,32-/m0/s1

InChI Key

KVXMPQFKQBICKI-UQVKNAHLSA-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
Betula pendula	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
20-hydroxysteroid
Steroid ester
3-oxosteroid
Hydroxysteroid
Oxosteroid
14-alpha-methylsteroid
3-oxo-5-alpha-steroid
Steroid
Tertiary alcohol
Ketone
Carboxylic acid ester
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	6.54	ChemAxon
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.57 m³·mol⁻¹	ChemAxon
Polarizability	59.5 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

69612182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate (NP0210335)

MOL for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D MOL for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D SDF for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D-SDF for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

PDB for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D PDB for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

SMILES for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

INCHI for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

Structure for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D Structure for NP0210335 ((1s,3ar,3br,5ar,9ar,9br,11r,11ar)-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethyl-7-oxo-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)