NP-MRD: Showing NP-Card for (1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one (NP0235594)

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Record Information

Version

2.0

Created at

2022-09-06 18:17:08 UTC

Updated at

2022-09-06 18:17:08 UTC

NP-MRD ID

NP0235594

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one

Description

Strongylophorine-8 belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. (1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one is found in Petrosia durissima. (1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one was first documented in 2007 (PMID: 17407351). Based on a literature review very few articles have been published on strongylophorine-8 (PMID: 21982768).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220172D          

 31 35  0  0  1  0            999 V2000
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    4.6141   -0.1169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1455   -0.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3306    0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5179    0.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9887    0.1667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.2336   -1.4462    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


  Mrv1652309062220172D          

 31 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0235594

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)CC[C@H]2[C@@](C)(CC[C@H]3[C@]4(C)CCC[C@]23COC4=O)[C@@H]1CC1=CC(O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O5/c1-23-11-7-20-24(2)9-4-10-26(20,15-31-22(24)29)19(23)8-12-25(3,30)21(23)14-16-13-17(27)5-6-18(16)28/h5-6,13,19-21,27-28,30H,4,7-12,14-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,26-/m0/s1

> <INCHI_KEY>
PRLHXGOJZIVTIS-VRRJBYJJSA-N

> <FORMULA>
C26H36O5

> <MOLECULAR_WEIGHT>
428.569

> <EXACT_MASS>
428.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.861708828772876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,6S,7R,10R,11S)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0^{1,10}.0^{2,7}]heptadecan-12-one

> <JCHEM_LOGP>
4.658937215333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.717412713434843

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.846098300745066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.903132679056152

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
118.0107

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6S,7R,10R,11S)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0^{1,10}.0^{2,7}]heptadecan-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       9.945   0.554   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.613  -0.218   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.605  -1.396   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.084   1.228   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.567   1.493   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.579   0.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.062   0.576   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.748   1.379   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.251   1.018   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.448  -0.296   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.809  -1.793   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.436  -2.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.123  -2.596   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.884  -4.117   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.393  -2.607   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.423  -0.921   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.074  -0.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.603  -2.052   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.120  -2.316   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.108  -1.135   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.637  -2.581   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.625  -1.400   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.154  -2.846   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.167  -4.027   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.650  -3.763   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.662  -4.944   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.145  -4.679   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.191  -6.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.708  -6.655   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.696  -5.474   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.213  -5.738   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8   16   17                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   17                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    7                                                       
CONECT   17   11    7   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    6   21   22                                             
CONECT   21   20                                                            
CONECT   22   20    2   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   24   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₅

Average Mass

428.5690 Da

Monoisotopic Mass

428.25627 Da

IUPAC Name

(1S,2S,5S,6S,7R,10R,11S)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0^{1,10}.0^{2,7}]heptadecan-12-one

Traditional Name

(1S,2S,5S,6S,7R,10R,11S)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0^{1,10}.0^{2,7}]heptadecan-12-one

CAS Registry Number

Not Available

SMILES

C[C@]1(O)CC[C@H]2[C@@](C)(CC[C@H]3[C@]4(C)CCC[C@]23COC4=O)[C@@H]1CC1=CC(O)=CC=C1O

InChI Identifier

InChI=1S/C26H36O5/c1-23-11-7-20-24(2)9-4-10-26(20,15-31-22(24)29)19(23)8-12-25(3,30)21(23)14-16-13-17(27)5-6-18(16)28/h5-6,13,19-21,27-28,30H,4,7-12,14-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,26-/m0/s1

InChI Key

PRLHXGOJZIVTIS-VRRJBYJJSA-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
Petrosia durissima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

Oxosteroid
3-oxo-5-alpha-steroid
Naphthopyran
Naphthalene
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Delta valerolactone
Delta_valerolactone
Phenol
Monocyclic benzene moiety
Oxane
Benzenoid
Pyran
Cyclic alcohol
Tertiary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	4.66	ChemAxon
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	118.01 m³·mol⁻¹	ChemAxon
Polarizability	47.86 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

23283193

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14564373

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Warabi K, Patrick BO, Austin P, Roskelley CD, Roberge M, Andersen RJ: Strongylophorine-26, an inhibitor of cancer cell Invasion: SAR revealed by synthesis of analogues. J Nat Prod. 2007 May;70(5):736-40. doi: 10.1021/np060481l. Epub 2007 Apr 4. [PubMed:17407351 ]
Sasaki S, Tozawa T, Van Wagoner RM, Ireland CM, Harper MK, Satoh T: Strongylophorine-8, a pro-electrophilic compound from the marine sponge Petrosia (Strongylophora) corticata, provides neuroprotection through Nrf2/ARE pathway. Biochem Biophys Res Commun. 2011 Nov 11;415(1):6-10. doi: 10.1016/j.bbrc.2011.09.114. Epub 2011 Oct 1. [PubMed:21982768 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one (NP0235594)

MOL for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

3D MOL for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

3D SDF for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

3D-SDF for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

PDB for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

3D PDB for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

SMILES for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

INCHI for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

Structure for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)

3D Structure for NP0235594 ((1s,2s,5s,6s,7r,10r,11s)-6-[(2,5-dihydroxyphenyl)methyl]-5-hydroxy-5,7,11-trimethyl-13-oxatetracyclo[9.3.3.0¹,¹⁰.0²,⁷]heptadecan-12-one)