NP-MRD: Showing NP-Card for Morolic acid (NP0071510)

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Record Information

Version

2.0

Created at

2022-04-28 16:53:07 UTC

Updated at

2022-04-28 16:53:07 UTC

NP-MRD ID

NP0071510

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Morolic acid

Description

Morolic acid, also known as morolate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Morolic acid is found in Adina pilulifera, Brucea javanica, Corymbia citriodora, Eucalyptus grossa, Machaerocereus eruca, Mora excelsa Benth. , Ozothamnus ledifolius, Phoradendron reichenbachianum, Pistacia terebinthus , Serjania triquetra and Stenocereus eruca. Morolic acid was first documented in 2008 (PMID: 18300194). Based on a literature review a significant number of articles have been published on Morolic acid (PMID: 22360797) (PMID: 33322233) (PMID: 32311084) (PMID: 28881197) (PMID: 27214242) (PMID: 26762062).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218532D          

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     RDKit          3D

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M  END


  Mrv1652304282218532D          

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  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
  7 14  1  1  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 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
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 20 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 17 26  1  0  0  0  0
 17 27  1  0  0  0  0
 11 28  1  6  0  0  0
  8 29  1  1  0  0  0
  5 30  1  1  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  2 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0071510

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)C2=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h18-19,21-23,31H,8-17H2,1-7H3,(H,32,33)/t19-,21+,22-,23+,27+,28-,29-,30+/m1/s1

> <INCHI_KEY>
RGZSSKBTFGNUCG-VNTGHVHSSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.914150331831166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6aR,6bR,8aR,10S,12aR,12bR,14aS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
6.70

> <JCHEM_LOGP>
6.594833433333333

> <ALOGPS_LOGS>
-5.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433390176508

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.689889634050666

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351231316396878

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
133.62449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.80e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6aR,6bR,8aR,10S,12aR,12bR,14aS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-3,4,5,6,7,8,8a,10,11,12,12b,13,14,14a-tetradecahydropicene-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   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.510  -2.103   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.742  -1.380   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.885   3.635   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.397   3.643   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.650   2.920   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   30                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   29                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   22   28                                             
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26   27                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21   23                                             
CONECT   21   20   22                                                       
CONECT   22   21   11                                                       
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   17                                                            
CONECT   27   17                                                            
CONECT   28   11                                                            
CONECT   29    8                                                            
CONECT   30    5                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    2                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Morolate	Generator

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7110 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

(4aS,6aR,6bR,8aR,10S,12aR,12bR,14aS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aS,6aR,6bR,8aR,10S,12aR,12bR,14aS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-3,4,5,6,7,8,8a,10,11,12,12b,13,14,14a-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)C2=C1)C(O)=O

InChI Identifier

InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h18-19,21-23,31H,8-17H2,1-7H3,(H,32,33)/t19-,21+,22-,23+,27+,28-,29-,30+/m1/s1

InChI Key

RGZSSKBTFGNUCG-VNTGHVHSSA-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
Adina pilulifera	Plant	KNApSAcK
Brucea javanica	LOTUS Database	35616633
Corymbia citriodora	LOTUS Database	35616633
Eucalyptus grossa	LOTUS Database	35616633
Machaerocereus eruca	-	KNApSAcK
Mora excelsa Benth.	-	KNApSAcK
Ozothamnus ledifolius	LOTUS Database	35616633
Phoradendron reichenbachianum	LOTUS Database	35616633
Pistacia terebinthus	Plant	KNApSAcK
Serjania triquetra	LOTUS Database	35616633
Stenocereus eruca	Plant	KNApSAcK

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
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	6.7	ALOGPS
logP	6.59	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.69	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	54.91 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

C00030794

Chemspider ID

429158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

489944

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lopez-Martinez S, Navarrete-Vazquez G, Estrada-Soto S, Leon-Rivera I, Rios MY: Chemical constituents of the hemiparasitic plant Phoradendron brachystachyum DC Nutt (Viscaceae). Nat Prod Res. 2013;27(2):130-6. doi: 10.1080/14786419.2012.662646. Epub 2012 Feb 23. [PubMed:22360797 ]
Chae SI, Yi SA, Nam KH, Park KJ, Yun J, Kim KH, Lee J, Han JW: Morolic Acid 3-O-Caffeate Inhibits Adipogenesis by Regulating Epigenetic Gene Expression. Molecules. 2020 Dec 13;25(24). pii: molecules25245910. doi: 10.3390/molecules25245910. [PubMed:33322233 ]
Srisawat P, Yasumoto S, Fukushima EO, Robertlee J, Seki H, Muranaka T: Production of the bioactive plant-derived triterpenoid morolic acid in engineered Saccharomyces cerevisiae. Biotechnol Bioeng. 2020 Jul;117(7):2198-2208. doi: 10.1002/bit.27357. Epub 2020 May 8. [PubMed:32311084 ]
Lehbili M, Alabdul Magid A, Kabouche A, Voutquenne-Nazabadioko L, Abedini A, Morjani H, Sarazin T, Gangloff SC, Kabouche Z: Oleanane-type triterpene saponins from Calendula stellata. Phytochemistry. 2017 Dec;144:33-42. doi: 10.1016/j.phytochem.2017.08.015. Epub 2017 Sep 4. [PubMed:28881197 ]
Andre CM, Legay S, Deleruelle A, Nieuwenhuizen N, Punter M, Brendolise C, Cooney JM, Lateur M, Hausman JF, Larondelle Y, Laing WA: Multifunctional oxidosqualene cyclases and cytochrome P450 involved in the biosynthesis of apple fruit triterpenic acids. New Phytol. 2016 Sep;211(4):1279-94. doi: 10.1111/nph.13996. Epub 2016 May 23. [PubMed:27214242 ]
Li B, Gao JY, Gong LM, Liu PA, Li SX: [Chemical Constituents From Rhus chinensis Fruit Dregs]. Zhong Yao Cai. 2015 Jun;38(6):1209-11. [PubMed:26762062 ]
Guo YE, Wang LL, Li ZL, Niu SL, Liu XQ, Hua HM, Chen H, Chu J, Zhang TC: Triterpenes and xanthones from the stem bark of Garcinia tetralata. J Asian Nat Prod Res. 2011 May;13(5):440-3. doi: 10.1080/10286020.2011.568414. [PubMed:21534043 ]
Dorr CR, Yemets S, Kolomitsyna O, Krasutsky P, Mansky LM: Triterpene derivatives that inhibit human immunodeficiency virus type 1 replication. Bioorg Med Chem Lett. 2011 Jan 1;21(1):542-5. doi: 10.1016/j.bmcl.2010.10.078. [PubMed:21084190 ]
Jeong W, Hong SS, Kim N, Yang YT, Shin YS, Lee C, Hwang BY, Lee D: Bioactive triterpenoids from Callistemon lanceolatus. Arch Pharm Res. 2009 Jun;32(6):845-9. doi: 10.1007/s12272-009-1605-3. Epub 2009 Jun 26. [PubMed:19557361 ]
Li J, Lu Y, Su X, Li F, She Z, He X, Lin Y: A norsesquiterpene lactone and a benzoic acid derivative from the leaves of Cyclocarya paliurus and their glucosidase and glycogen phosphorylase inhibiting activities. Planta Med. 2008 Feb;74(3):287-9. doi: 10.1055/s-2008-1034309. Epub 2008 Feb 26. [PubMed:18300194 ]

Showing NP-Card for Morolic acid (NP0071510)

MOL for NP0071510 (Morolic acid)

3D MOL for NP0071510 (Morolic acid)

3D SDF for NP0071510 (Morolic acid)

3D-SDF for NP0071510 (Morolic acid)

PDB for NP0071510 (Morolic acid)

3D PDB for NP0071510 (Morolic acid)

SMILES for NP0071510 (Morolic acid)

INCHI for NP0071510 (Morolic acid)

Structure for NP0071510 (Morolic acid)

3D Structure for NP0071510 (Morolic acid)