NP-MRD: Showing NP-Card for Heracleifolinol (NP0066514)

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Record Information

Version

2.0

Created at

2022-04-28 10:46:10 UTC

Updated at

2022-04-28 10:46:10 UTC

NP-MRD ID

NP0066514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Heracleifolinol

Description

(10S,23R,24R)-3beta,10:16Beta,23-Diepoxy-9,10-seco-9beta,19-cyclo-5alpha-lanost-8-ene-15alpha,16,24,25-tetraol 24-acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Heracleifolinol is found in Actaea heracleifolia and Cimicifuga heracleifolia KOMAROV . Based on a literature review very few articles have been published on (10S,23R,24R)-3beta,10:16Beta,23-Diepoxy-9,10-seco-9beta,19-cyclo-5alpha-lanost-8-ene-15alpha,16,24,25-tetraol 24-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212462D          

 39 44  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282212462D          

 39 44  0  0  1  0            999 V2000
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    6.1552    0.6925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0330   -0.1234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6784   -0.6372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4461   -0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5684    0.4807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9230    0.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3361    0.7828    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9816    0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6270   -0.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4954    0.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4677   -0.3765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4584    1.5987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2261    1.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3484    2.7166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8715    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5562   -1.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1916    1.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2812    1.8746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5365    1.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676   -0.0772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 25 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 21 34  1  1  0  0  0
 19 35  1  1  0  0  0
 18 36  1  1  0  0  0
 17 37  1  1  0  0  0
 16 38  1  6  0  0  0
  4 39  1  6  0  0  0
  1 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0066514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](O[C@@]2(O)[C@H](O)[C@@]3(C)C4=C(CC[C@]3(C)[C@@H]12)C[C@]12CC[C@H](O1)C(C)(C)[C@@H]2CC4)[C@@H](OC(C)=O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O7/c1-17-15-21(25(28(5,6)35)37-18(2)33)38-32(36)24(17)29(7)13-11-19-16-31-14-12-23(39-31)27(3,4)22(31)10-9-20(19)30(29,8)26(32)34/h17,21-26,34-36H,9-16H2,1-8H3/t17-,21-,22+,23+,24-,25-,26-,29-,30-,31+,32-/m1/s1

> <INCHI_KEY>
MRPSSAZAIPQONH-LAGJWBHSSA-N

> <FORMULA>
C32H50O7

> <MOLECULAR_WEIGHT>
546.745

> <EXACT_MASS>
546.35565395

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
62.053413018927216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-1-[(1S,6R,7R,8R,10R,12R,13R,14R,18S,20S)-12,13-dihydroxy-6,8,14,19,19-pentamethyl-11,23-dioxahexacyclo[18.2.1.0^{1,18}.0^{3,15}.0^{6,14}.0^{7,12}]tricos-3(15)-en-10-yl]-2-hydroxy-2-methylpropyl acetate

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
3.631334989666666

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.517222285781031

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.889762307833669

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1404000729299595

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
146.43860000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-[(1S,6R,7R,8R,10R,12R,13R,14R,18S,20S)-12,13-dihydroxy-6,8,14,19,19-pentamethyl-11,23-dioxahexacyclo[18.2.1.0^{1,18}.0^{3,15}.0^{6,14}.0^{7,12}]tricos-3(15)-en-10-yl]-2-hydroxy-2-methylpropyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.096   1.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.952   0.575   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.048  -0.606   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.882   0.348   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.267   1.949   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.004   2.734   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.532   4.181   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.975   3.880   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.507   2.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.973   2.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494   0.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.666  -0.348   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.120  -0.555   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.376  -1.715   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.915  -1.782   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.743  -0.484   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.032   0.882   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.112   1.980   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.490   1.293   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.262  -0.230   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.466  -1.190   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.899  -0.626   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.128   0.897   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.923   1.856   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      15.561   1.461   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.766   0.502   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.970  -0.457   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.725   1.707   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      15.806  -0.703   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      15.789   2.984   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.222   3.548   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      17.450   5.071   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      18.427   2.589   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.238  -2.713   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.558   2.831   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.858   3.499   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.468   2.315   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.592  -1.768   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.926  -0.144   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13   39                                             
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    4                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20   38                                             
CONECT   17   16   11   18   37                                             
CONECT   18   17   19   36                                                  
CONECT   19   18   20   24   35                                             
CONECT   20   19   16   21                                                  
CONECT   21   20   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26   30                                                  
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   21                                                            
CONECT   35   19                                                            
CONECT   36   18                                                            
CONECT   37   17                                                            
CONECT   38   16                                                            
CONECT   39    4    1                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
(10S,23R,24R)-3b,10:16b,23-Diepoxy-9,10-seco-9b,19-cyclo-5a-lanost-8-ene-15a,16,24,25-tetraol 24-acetate	Generator
(10S,23R,24R)-3b,10:16b,23-Diepoxy-9,10-seco-9b,19-cyclo-5a-lanost-8-ene-15a,16,24,25-tetraol 24-acetic acid	Generator
(10S,23R,24R)-3beta,10:16beta,23-Diepoxy-9,10-seco-9beta,19-cyclo-5alpha-lanost-8-ene-15alpha,16,24,25-tetraol 24-acetic acid	Generator
(10S,23R,24R)-3Β,10:16β,23-diepoxy-9,10-seco-9β,19-cyclo-5α-lanost-8-ene-15α,16,24,25-tetraol 24-acetate	Generator
(10S,23R,24R)-3Β,10:16β,23-diepoxy-9,10-seco-9β,19-cyclo-5α-lanost-8-ene-15α,16,24,25-tetraol 24-acetic acid	Generator

Chemical Formula

C₃₂H₅₀O₇

Average Mass

546.7450 Da

Monoisotopic Mass

546.35565 Da

IUPAC Name

(1R)-1-[(1S,6R,7R,8R,10R,12R,13R,14R,18S,20S)-12,13-dihydroxy-6,8,14,19,19-pentamethyl-11,23-dioxahexacyclo[18.2.1.0^{1,18}.0^{3,15}.0^{6,14}.0^{7,12}]tricos-3(15)-en-10-yl]-2-hydroxy-2-methylpropyl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](O[C@@]2(O)[C@H](O)[C@@]3(C)C4=C(CC[C@]3(C)[C@@H]12)C[C@]12CC[C@H](O1)C(C)(C)[C@@H]2CC4)[C@@H](OC(C)=O)C(C)(C)O

InChI Identifier

InChI=1S/C32H50O7/c1-17-15-21(25(28(5,6)35)37-18(2)33)38-32(36)24(17)29(7)13-11-19-16-31-14-12-23(39-31)27(3,4)22(31)10-9-20(19)30(29,8)26(32)34/h17,21-26,34-36H,9-16H2,1-8H3/t17-,21-,22+,23+,24-,25-,26-,29-,30-,31+,32-/m1/s1

InChI Key

MRPSSAZAIPQONH-LAGJWBHSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Actaea heracleifolia	LOTUS Database	35616633
Cimicifuga heracleifolia KOMAROV	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oxane
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.49	ALOGPS
logP	3.63	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	10.89	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	146.44 m³·mol⁻¹	ChemAxon
Polarizability	62.05 Å³	ChemAxon
Number of Rings	6	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

100936509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Heracleifolinol (NP0066514)

MOL for NP0066514 (Heracleifolinol)

3D MOL for NP0066514 (Heracleifolinol)

3D SDF for NP0066514 (Heracleifolinol)

3D-SDF for NP0066514 (Heracleifolinol)

PDB for NP0066514 (Heracleifolinol)

3D PDB for NP0066514 (Heracleifolinol)

SMILES for NP0066514 (Heracleifolinol)

INCHI for NP0066514 (Heracleifolinol)

Structure for NP0066514 (Heracleifolinol)

3D Structure for NP0066514 (Heracleifolinol)