NP-MRD: Showing NP-Card for (+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid (NP0072628)

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Record Information

Version

1.0

Created at

2022-04-28 17:56:53 UTC

Updated at

2022-04-28 17:56:53 UTC

NP-MRD ID

NP0072628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid

Description

1Beta,3beta,5alpha,23,24-Pentahydroxy-30-noroleana-12,20(29)-diene-28-oic acid belongs to the class of organic compounds known as 11-hydroxysteroids. These are steroids carrying a hydroxyl group at the 11-position of the steroid backbone. (+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid is found in Paeonia emodi . Based on a literature review very few articles have been published on 1beta,3beta,5alpha,23,24-Pentahydroxy-30-noroleana-12,20(29)-diene-28-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219562D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282219562D          

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    2.6907    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  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
  6  7  1  1  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 13 16  1  1  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 29  1  6  0  0  0
 21 30  1  6  0  0  0
 20 31  1  6  0  0  0
 19 32  1  1  0  0  0
 12 33  1  6  0  0  0
  5 34  1  6  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@]3(O)[C@](C)([C@H](O)C[C@H](O)C3(CO)CO)[C@H]1CC=C1[C@@H]3CC(=C)CC[C@@]3(CC[C@@]21C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O7/c1-17-7-8-27(23(34)35)11-9-24(2)18(19(27)13-17)5-6-20-25(24,3)10-12-29(36)26(20,4)21(32)14-22(33)28(29,15-30)16-31/h5,19-22,30-33,36H,1,6-16H2,2-4H3,(H,34,35)/t19-,20-,21+,22-,24+,25+,26-,27-,29-/m0/s1

> <INCHI_KEY>
QNGKJIVXPKRSAZ-CNNHGBCPSA-N

> <FORMULA>
C29H44O7

> <MOLECULAR_WEIGHT>
504.664

> <EXACT_MASS>
504.308703757

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.77482674468244

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6aS,6bR,8aS,10S,12R,12aS,12bS,14bS)-8a,10,12-trihydroxy-9,9-bis(hydroxymethyl)-6a,6b,12a-trimethyl-2-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
1.0786008110000007

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.550273516846058

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.420067263935815

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8548495947676145

> <JCHEM_POLAR_SURFACE_AREA>
138.45

> <JCHEM_REFRACTIVITY>
135.32229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6aS,6bR,8aS,10S,12R,12aS,12bS,14bS)-8a,10,12-trihydroxy-9,9-bis(hydroxymethyl)-6a,6b,12a-trimethyl-2-methylidene-3,4,5,6,7,8,10,11,12,12b,13,14b-dodecahydro-1H-picene-4a-carboxylic acid

> <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      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.114  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.102   2.197   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.850   4.366   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334   3.437   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15   34                                             
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   17   33                                             
CONECT   13   12    8   14   16                                             
CONECT   14   13   15                                                       
CONECT   15   14    5                                                       
CONECT   16   13                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24   32                                             
CONECT   20   19   11   21   31                                             
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   19   25   27                                             
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27                                                            
CONECT   29   23                                                            
CONECT   30   21                                                            
CONECT   31   20                                                            
CONECT   32   19                                                            
CONECT   33   12                                                            
CONECT   34    5   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
1b,3b,5a,23,24-Pentahydroxy-30-noroleana-12,20(29)-diene-28-Oate	Generator
1b,3b,5a,23,24-Pentahydroxy-30-noroleana-12,20(29)-diene-28-Oic acid	Generator
1beta,3beta,5alpha,23,24-Pentahydroxy-30-noroleana-12,20(29)-diene-28-Oate	Generator
1Β,3β,5α,23,24-pentahydroxy-30-noroleana-12,20(29)-diene-28-Oate	Generator
1Β,3β,5α,23,24-pentahydroxy-30-noroleana-12,20(29)-diene-28-Oic acid	Generator

Chemical Formula

C₂₉H₄₄O₇

Average Mass

504.6640 Da

Monoisotopic Mass

504.30870 Da

IUPAC Name

(4aS,6aS,6bR,8aS,10S,12R,12aS,12bS,14bS)-8a,10,12-trihydroxy-9,9-bis(hydroxymethyl)-6a,6b,12a-trimethyl-2-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aS,6aS,6bR,8aS,10S,12R,12aS,12bS,14bS)-8a,10,12-trihydroxy-9,9-bis(hydroxymethyl)-6a,6b,12a-trimethyl-2-methylidene-3,4,5,6,7,8,10,11,12,12b,13,14b-dodecahydro-1H-picene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@]3(O)[C@](C)([C@H](O)C[C@H](O)C3(CO)CO)[C@H]1CC=C1[C@@H]3CC(=C)CC[C@@]3(CC[C@@]21C)C(O)=O

InChI Identifier

InChI=1S/C29H44O7/c1-17-7-8-27(23(34)35)11-9-24(2)18(19(27)13-17)5-6-20-25(24,3)10-12-29(36)26(20,4)21(32)14-22(33)28(29,15-30)16-31/h5,19-22,30-33,36H,1,6-16H2,2-4H3,(H,34,35)/t19-,20-,21+,22-,24+,25+,26-,27-,29-/m0/s1

InChI Key

QNGKJIVXPKRSAZ-CNNHGBCPSA-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
Paeonia emodi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 11-hydroxysteroids. These are steroids carrying a hydroxyl group at the 11-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

11-hydroxysteroids

Alternative Parents

Substituents

11-hydroxysteroid
11-alpha-hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Alcohol
Primary alcohol
Organic oxide
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	2.16	ALOGPS
logP	1.08	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	135.32 m³·mol⁻¹	ChemAxon
Polarizability	55.77 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

8776997

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10601624

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid (NP0072628)

MOL for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

3D MOL for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

3D SDF for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

3D-SDF for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

PDB for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

3D PDB for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

SMILES for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

INCHI for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

Structure for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)

3D Structure for NP0072628 ((+)-1beta,3beta,5alpha,23,24-Pentahydroxy-30-norolean-12,20(29)-dien-28-oic acid)