NP-MRD: Showing NP-Card for stypotriol (NP0148234)

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Record Information

Version

2.0

Created at

2022-09-02 03:57:29 UTC

Updated at

2022-09-02 03:57:29 UTC

NP-MRD ID

NP0148234

Secondary Accession Numbers

None

Natural Product Identification

Common Name

stypotriol

Description

Stypotriol belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. stypotriol is found in Stypopodium flabelliforme and Stypopodium zonale. stypotriol was first documented in 2009 (PMID: 19768979). Based on a literature review very few articles have been published on Stypotriol (PMID: 21673894).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205572D          

 31 35  0  0  1  0            999 V2000
    6.0659   -1.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6798   -0.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1181    0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7319    1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1702    1.8104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9074    1.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213    1.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4692    0.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5404   -0.5162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6565    0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022205572D          

 31 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0148234

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H]2[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@@]2(C)[C@]11CC2=C(O1)C(C)=CC(O)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O4/c1-15-13-18(28)22(30)17-14-27(31-23(15)17)16(2)7-8-20-25(5)11-10-21(29)24(3,4)19(25)9-12-26(20,27)6/h13,16,19-21,28-30H,7-12,14H2,1-6H3/t16-,19-,20+,21-,25-,26+,27-/m0/s1

> <INCHI_KEY>
HJSZCMVJNUBOQM-JZFVXYNCSA-N

> <FORMULA>
C27H40O4

> <MOLECULAR_WEIGHT>
428.613

> <EXACT_MASS>
428.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.67720196710233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-2',4'b,7,8',8',10'a-hexamethyl-3',4',4'a,4'b,5',6',7',8',8'a,9',10',10'a-dodecahydro-2'H,3H-spiro[1-benzofuran-2,1'-phenanthrene]-4,5,7'-triol

> <ALOGPS_LOGP>
5.73

> <JCHEM_LOGP>
5.960921963666667

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.24283082577012

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.903977606479916

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8350820116931555

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
122.53859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-2',4'b,7,8',8',10'a-hexamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3H-spiro[1-benzofuran-2,1'-phenanthrene]-4,5,7'-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      11.323  -1.952   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.602  -0.591   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.420   0.714   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.700   2.075   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.518   3.379   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.161   2.131   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.440   3.492   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.342   0.826   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.063  -0.535   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.992  -1.641   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.609  -0.964   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.825   0.561   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.553  -2.503   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.857  -3.321   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.192  -3.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.887  -2.405   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.943  -0.866   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.638  -0.048   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.582  -1.587   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.278  -0.769   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.027   0.049   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.029   1.588   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.276   2.406   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.390   2.309   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.444   3.524   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.422   3.452   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.695   1.491   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.055   2.212   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.360   1.394   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.304  -0.145   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.375   0.961   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   30                                             
CONECT   12   11    8                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   17   11   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
Stypotriol triacetate	MeSH

Chemical Formula

C₂₇H₄₀O₄

Average Mass

428.6130 Da

Monoisotopic Mass

428.29266 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H]2[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@@]2(C)[C@]11CC2=C(O1)C(C)=CC(O)=C2O

InChI Identifier

InChI=1S/C27H40O4/c1-15-13-18(28)22(30)17-14-27(31-23(15)17)16(2)7-8-20-25(5)11-10-21(29)24(3,4)19(25)9-12-26(20,27)6/h13,16,19-21,28-30H,7-12,14H2,1-6H3/t16-,19-,20+,21-,25-,26+,27-/m0/s1

InChI Key

HJSZCMVJNUBOQM-JZFVXYNCSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Stypopodium flabelliforme	LOTUS Database	35616633
Stypopodium zonale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Spongiane diterpenoid
Phenanthrene
Coumaran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Cyclic alcohol
Secondary alcohol
Oxacycle
Ether
Organoheterocyclic compound
Polyol
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	5.73	ALOGPS
logS	-5	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043047

Chemspider ID

10469911

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23424859

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pereira DM, Cheel J, Areche C, San-Martin A, Rovirosa J, Silva LR, Valentao P, Andrade PB: Anti-proliferative activity of meroditerpenoids isolated from the brown alga Stypopodium flabelliforme against several cancer cell lines. Mar Drugs. 2011;9(5):852-862. doi: 10.3390/md9050852. Epub 2011 May 13. [PubMed:21673894 ]
Munoz MA, Areche C, San-Martin A, Rovirosa J, Joseph-Nathan P: VCD determination of the absolute configuration of stypotriol. Nat Prod Commun. 2009 Aug;4(8):1037-40. [PubMed:19768979 ]
LOTUS database [Link]

Showing NP-Card for stypotriol (NP0148234)

MOL for NP0148234 (stypotriol)

3D MOL for NP0148234 (stypotriol)

3D SDF for NP0148234 (stypotriol)

3D-SDF for NP0148234 (stypotriol)

PDB for NP0148234 (stypotriol)

3D PDB for NP0148234 (stypotriol)

SMILES for NP0148234 (stypotriol)

INCHI for NP0148234 (stypotriol)

Structure for NP0148234 (stypotriol)

3D Structure for NP0148234 (stypotriol)