NP-MRD: Showing NP-Card for Zeorin (NP0066370)

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Record Information

Version

2.0

Created at

2022-04-28 10:38:50 UTC

Updated at

2022-04-28 10:38:50 UTC

NP-MRD ID

NP0066370

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Zeorin

Description

Zeorin belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30). Thus, zeorin is considered to be a hopanoid. Zeorin is found in Adiantum edgeworthii, Anaptychia hypoglauca, Anaptychia speciosa, Arenaria kansuensis, Asterella blumeana, Cladonia deformis, Coccifera plurota, Conocephalum japonicum, Conoideocrella luteorostrata, Conoideocrella tenuis, Cyathus helenae, Aspergillus falconensis, Frullania brasiliensis, Glochidion sp., Heterodermia diademata, Hypotrachyna nepalensis, Iris missouriensis, Lepraria latebrarum, Nephroma arcticum, Parmelia leucotyliza, Peltigera aphthosa, Peltigera polydactylon, Physcia aipolia, Plagiochasma rupestre, Radula complanata, Reboulia hemisphaerica, Tripterygium wilfordii and Urceolaria cretacea. Zeorin was first documented in 2017 (PMID: 28491237). Based on a literature review a small amount of articles have been published on zeorin (PMID: 32376482) (PMID: 33967344) (PMID: 33576270) (PMID: 32791845).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212382D          

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M  END


  Mrv1652304282212382D          

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    5.3147    3.0684    0.0000 C   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
  7 15  1  1  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 20 23  1  6  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 16 27  1  6  0  0  0
 12 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
M  END
> <DATABASE_ID>
NP0066370

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3[C@@H](O)C[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O2/c1-25(2)14-9-15-28(6)23-11-10-22-27(5)16-12-19(26(3,4)32)20(27)13-17-29(22,7)30(23,8)18-21(31)24(25)28/h19-24,31-32H,9-18H2,1-8H3/t19-,20-,21-,22+,23+,24-,27-,28+,29+,30+/m0/s1

> <INCHI_KEY>
KYBLAIAGFNCVHL-PMVHANJISA-N

> <FORMULA>
C30H52O2

> <MOLECULAR_WEIGHT>
444.744

> <EXACT_MASS>
444.396730914

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
55.62181023706379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6S,9S,10R,13R,14R,19S,20S)-6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-20-ol

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
6.324577606999999

> <ALOGPS_LOGS>
-6.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.477491190507745

> <JCHEM_PKA_STRONGEST_BASIC>
-0.08943832062407286

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
132.9669

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.68e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6S,9S,10R,13R,14R,19S,20S)-6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-20-ol

> <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       9.931   1.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.681   2.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.890   4.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.351   4.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.601   2.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.391   1.498   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.061   2.796   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.271   4.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.021   5.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.560   5.486   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.310   6.832   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.731   4.094   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.982   2.749   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.772   1.427   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.312   1.451   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.442   2.726   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.651   4.048   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.401   5.393   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.941   5.416   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.850   3.704   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.987   2.171   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.429   1.566   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.010   4.717   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.170   5.730   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.997   5.877   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.023   3.557   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.089   1.329   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.481   5.440   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.409   5.652   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.851   1.474   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.184   5.024   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.921   5.728   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
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   15                                                  
CONECT    8    7    9   12   29                                             
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   19   28                                             
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17   22   27                                             
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   12                                                       
CONECT   20   17   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   16                                                       
CONECT   23   20   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   16                                                            
CONECT   28   12                                                            
CONECT   29    8                                                            
CONECT   30    5                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₂O₂

Average Mass

444.7440 Da

Monoisotopic Mass

444.39673 Da

IUPAC Name

(1R,2R,5S,6S,9S,10R,13R,14R,19S,20S)-6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-20-ol

Traditional Name

(1R,2R,5S,6S,9S,10R,13R,14R,19S,20S)-6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-20-ol

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3[C@@H](O)C[C@@]12C

InChI Identifier

InChI=1S/C30H52O2/c1-25(2)14-9-15-28(6)23-11-10-22-27(5)16-12-19(26(3,4)32)20(27)13-17-29(22,7)30(23,8)18-21(31)24(25)28/h19-24,31-32H,9-18H2,1-8H3/t19-,20-,21-,22+,23+,24-,27-,28+,29+,30+/m0/s1

InChI Key

KYBLAIAGFNCVHL-PMVHANJISA-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
Adiantum edgeworthii	LOTUS Database	35616633
Anaptychia hypoglauca	-	KNApSAcK
Anaptychia speciosa	-	KNApSAcK
Arenaria kansuensis	LOTUS Database	35616633
Asterella blumeana	LOTUS Database	35616633
Cladonia deformis	Fungi	KNApSAcK
Coccifera plurota	-	KNApSAcK
Conocephalum supradecompositum	LOTUS Database	35616633
Conoideocrella luteorostrata	LOTUS Database	35616633
Conoideocrella tenuis	LOTUS Database	35616633
Cyathus helenae	Fungi	KNApSAcK
Emericella falconensis	LOTUS Database	35616633
Frullania brasiliensis	Plant	KNApSAcK
Glochidion sp.	Plant	KNApSAcK
Heterodermia diademata	LOTUS Database	35616633
Hypotrachyna nepalensis	LOTUS Database	35616633
Iris missouriensis	LOTUS Database	35616633
Lepraria latebrarum	-	KNApSAcK
Nephroma arcticum	Fungi	KNApSAcK
Parmelia leucotyliza	Fungi	KNApSAcK
Peltigera aphthosa	LOTUS Database	35616633
Peltigera polydactylon	LOTUS Database	35616633
Physcia aipolia	LOTUS Database	35616633
Plagiochasma rupestre	LOTUS Database	35616633
Radula complanata	LOTUS Database	35616633
Reboulia hemisphaerica	Plant	KNApSAcK
Tripterygium wilfordii	LOTUS Database	35616633
Urceolaria cretacea	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Hopanoids

Direct Parent

Hopanoids

Alternative Parents

Substituents

Triterpenoid
Hopane-skeleton
20-hydroxysteroid
Hydroxysteroid
2-hydroxysteroid
Steroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diol (CHEBI:67966 )
hopanoid (CHEBI:67966 )
pentacyclic triterpenoid (CHEBI:67966 )

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	5.7	ALOGPS
logP	6.32	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	19.48	ChemAxon
pKa (Strongest Basic)	-0.089	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.97 m³·mol⁻¹	ChemAxon
Polarizability	55.62 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

C00023787

Chemspider ID

140607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zeorin

METLIN ID

Not Available

PubChem Compound

159931

PDB ID

Not Available

ChEBI ID

67966

Good Scents ID

Not Available

References

General References

Sadorn K, Saepua S, Punyain W, Saortep W, Choowong W, Rachtawee P, Pittayakhajonwut P: Chromanones and aryl glucoside analogs from the entomopathogenic fungus Aschersonia confluens BCC53152. Fitoterapia. 2020 Jul;144:104606. doi: 10.1016/j.fitote.2020.104606. Epub 2020 May 3. [PubMed:32376482 ]
Prateeksha G, Rana TS, Ashthana AK, Barik SK, Singh BN: Screening of cryptogamic secondary metabolites as putative inhibitors of SARS-CoV-2 main protease and ribosomal binding domain of spike glycoprotein by molecular docking and molecular dynamics approaches. J Mol Struct. 2021 Sep 15;1240:130506. doi: 10.1016/j.molstruc.2021.130506. Epub 2021 Apr 29. [PubMed:33967344 ]
Duong TH, Nguyen VK, Sichaem J, Tran TN, Do TH, Pham NK, Nguyen TA, Nguyen TH, Mai DT, Nguyen NH, Huynh BL: Reticulatin, a novel C43-spiroterpenoid from the lichen Parmotrema reticulatum growing in Vietnam. Nat Prod Res. 2022 Jul;36(14):3705-3712. doi: 10.1080/14786419.2021.1885032. Epub 2021 Feb 12. [PubMed:33576270 ]
Fouotsa H, Dzoyem JP, Lannang AM, Stammler HG, Mbazoa CD, Luhmer M, Nkengfack AE, Allemann E, Delie F, Meyer F, Sewald N: Antiproliferative activity of a new xanthone derivative from leaves of Garcinia nobilis Engl. Nat Prod Res. 2021 Dec;35(24):5604-5611. doi: 10.1080/14786419.2020.1806270. Epub 2020 Aug 13. [PubMed:32791845 ]
Thadhani VM, Karunaratne V: Potential of Lichen Compounds as Antidiabetic Agents with Antioxidative Properties: A Review. Oxid Med Cell Longev. 2017;2017:2079697. doi: 10.1155/2017/2079697. Epub 2017 Apr 12. [PubMed:28491237 ]

Showing NP-Card for Zeorin (NP0066370)

MOL for NP0066370 (Zeorin)

3D MOL for NP0066370 (Zeorin)

3D SDF for NP0066370 (Zeorin)

3D-SDF for NP0066370 (Zeorin)

PDB for NP0066370 (Zeorin)

3D PDB for NP0066370 (Zeorin)

SMILES for NP0066370 (Zeorin)

INCHI for NP0066370 (Zeorin)

Structure for NP0066370 (Zeorin)

3D Structure for NP0066370 (Zeorin)