NP-MRD: Showing NP-Card for 22beta-Hydroxymaytenin (NP0074336)

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Record Information

Version

2.0

Created at

2022-04-28 19:30:36 UTC

Updated at

2022-04-28 19:30:36 UTC

NP-MRD ID

NP0074336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22beta-Hydroxymaytenin

Description

22-Hydroxytingenone, also known as tingenin b, belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. 22beta-Hydroxymaytenin is found in Acanthothamnus aphyllus, Catha edulis, Cheiloclinium cognatum, Elaeodendron croceum, Gymnosporia cassinoides, Peritassa campestris, Salacia campestris, Salacia chinensis, Salacia reticulata and Tripterygium wilfordii. 22beta-Hydroxymaytenin was first documented in 2019 (PMID: 30445109). Based on a literature review very few articles have been published on 22-Hydroxytingenone (PMID: 34411914).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221302D          

 32 36  0  0  1  0            999 V2000
    6.0770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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   -3.2397   -1.2682   -0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221302D          

 32 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0074336

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2[C@@](C)(CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]23C)[C@H](O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O4/c1-15-13-21-26(4,24(32)22(15)30)10-12-27(5)20-8-7-17-16(2)23(31)19(29)14-18(17)25(20,3)9-11-28(21,27)6/h7-8,14-15,21,24,31-32H,9-13H2,1-6H3/t15-,21-,24-,25+,26-,27-,28+/m1/s1

> <INCHI_KEY>
QIRUFAFQGKOTKA-ZRWKYKNNSA-N

> <FORMULA>
C28H36O4

> <MOLECULAR_WEIGHT>
436.592

> <EXACT_MASS>
436.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.55251595550277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6bS,8aR,9S,11R,12aS,12bS,14aR)-3,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydropicene-2,10-dione

> <ALOGPS_LOGP>
5.08

> <JCHEM_LOGP>
4.200325099333335

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.959480945364323

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.752315528117872

> <JCHEM_PKA_STRONGEST_BASIC>
-3.462479182472717

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
128.55929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6bS,8aR,9S,11R,12aS,12bS,14aR)-3,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,9,11,12,12a,13,14-octahydropicene-2,10-dione

> <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  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+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   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.034   3.437   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       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.644  -0.564   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       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.114  -1.897   0.000  0.00  0.00           C+0
CONECT    1    2    7   32                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6   11   30                                             
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   26   29                                             
CONECT    9    8   10   12   28                                             
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   15   22                                                  
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   16   12   25   27                                             
CONECT   25   24   26                                                       
CONECT   26   25    8                                                       
CONECT   27   24                                                            
CONECT   28    9                                                            
CONECT   29    8                                                            
CONECT   30    5                                                            
CONECT   31    4                                                            
CONECT   32    1                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
Tingenin b	MeSH

Chemical Formula

C₂₈H₃₆O₄

Average Mass

436.5920 Da

Monoisotopic Mass

436.26136 Da

IUPAC Name

(6bS,8aR,9S,11R,12aS,12bS,14aR)-3,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydropicene-2,10-dione

Traditional Name

(6bS,8aR,9S,11R,12aS,12bS,14aR)-3,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,9,11,12,12a,13,14-octahydropicene-2,10-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2[C@@](C)(CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]23C)[C@H](O)C1=O

InChI Identifier

InChI=1S/C28H36O4/c1-15-13-21-26(4,24(32)22(15)30)10-12-27(5)20-8-7-17-16(2)23(31)19(29)14-18(17)25(20,3)9-11-28(21,27)6/h7-8,14-15,21,24,31-32H,9-13H2,1-6H3/t15-,21-,24-,25+,26-,27-,28+/m1/s1

InChI Key

QIRUFAFQGKOTKA-ZRWKYKNNSA-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
Acanthothamnus aphyllus	LOTUS Database	35616633
Catha edulis	LOTUS Database	35616633
Cheiloclinium cognatum	Plant	KNApSAcK
Elaeodendron croceum	LOTUS Database	35616633
Gymnosporia cassinoides	LOTUS Database	35616633
Peritassa campestris	LOTUS Database	35616633
Salacia campestris	Plant	KNApSAcK
Salacia chinensis	LOTUS Database	35616633
Salacia reticulata	LOTUS Database	35616633
Tripterygium wilfordii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Enol
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	5.08	ALOGPS
logP	4.2	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	128.56 m³·mol⁻¹	ChemAxon
Polarizability	49.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

65923

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73147

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rodrigues ACBDC, Bomfim LM, Neves SP, Soares MBP, Dias RB, Valverde LF, Rocha CAG, Costa EV, da Silva FMA, Rocha WC, Koolen HHF, Bezerra DP: Tingenone and 22-hydroxytingenone target oxidative stress through downregulation of thioredoxin, leading to DNA double-strand break and JNK/p38-mediated apoptosis in acute myeloid leukemia HL-60 cells. Biomed Pharmacother. 2021 Oct;142:112034. doi: 10.1016/j.biopha.2021.112034. Epub 2021 Aug 16. [PubMed:34411914 ]
Rodrigues ACBDC, Oliveira FP, Dias RB, Sales CBS, Rocha CAG, Soares MBP, Costa EV, Silva FMAD, Rocha WC, Koolen HHF, Bezerra DP: In vitro and in vivo anti-leukemia activity of the stem bark of Salacia impressifolia (Miers) A. C. Smith (Celastraceae). J Ethnopharmacol. 2019 Mar 1;231:516-524. doi: 10.1016/j.jep.2018.11.008. Epub 2018 Nov 13. [PubMed:30445109 ]

Showing NP-Card for 22beta-Hydroxymaytenin (NP0074336)

MOL for NP0074336 (22beta-Hydroxymaytenin)

3D MOL for NP0074336 (22beta-Hydroxymaytenin)

3D SDF for NP0074336 (22beta-Hydroxymaytenin)

3D-SDF for NP0074336 (22beta-Hydroxymaytenin)

PDB for NP0074336 (22beta-Hydroxymaytenin)

3D PDB for NP0074336 (22beta-Hydroxymaytenin)

SMILES for NP0074336 (22beta-Hydroxymaytenin)

INCHI for NP0074336 (22beta-Hydroxymaytenin)

Structure for NP0074336 (22beta-Hydroxymaytenin)

3D Structure for NP0074336 (22beta-Hydroxymaytenin)