NP-MRD: Showing NP-Card for Verrucellol A (NP0044669)

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Record Information

Version

2.0

Created at

2022-02-24 21:11:30 UTC

Updated at

2026-02-05 04:21:06 UTC

NP-MRD ID

NP0044669

Natural Product DOI

https://doi.org/10.57994/5366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Verrucellol A

Description

Verrucellol A was first documented in 2021 (PMID: 33966392). Based on a literature review very few articles have been published on (1R,3aR,4R,5R,7aR)-1-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-octahydro-1H-indene-4,5-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302242222112D          

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M  END

     RDKit          3D

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M  END


  Mrv1652302242222112D          

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M  END
> <DATABASE_ID>
NP0044669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@]2([H])[C@]1(C)CC[C@@H](O)[C@@]2(O)CCC1=C(C)C=CC(O)=C1)[C@H](C)\C=C\[C@@H](C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O3/c1-18(2)19(3)7-8-21(5)24-11-12-25-27(24,6)15-14-26(30)28(25,31)16-13-22-17-23(29)10-9-20(22)4/h7-10,17-19,21,24-26,29-31H,11-16H2,1-6H3/b8-7+/t19-,21-,24-,25-,26-,27-,28-/m1/s1

> <INCHI_KEY>
OMFMYOPWRZBPAD-ZXIHGUFVSA-N

> <FORMULA>
C28H44O3

> <MOLECULAR_WEIGHT>
428.657

> <EXACT_MASS>
428.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.71214862672828

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3aR,4R,5R,7aR)-1-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-octahydro-1H-indene-4,5-diol

> <ALOGPS_LOGP>
5.61

> <JCHEM_LOGP>
6.7389974833333355

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.46333519653352

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.435000816720562

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2392549906531354

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
130.1274

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3aR,4R,5R,7aR)-1-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-hexahydro-1H-indene-4,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-22         0                                  
HETATM    1  H   UNK     0      -1.789   0.184   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       2.530  -1.303   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.036   0.999   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.253  -4.203   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.807  -4.203   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.624  -5.509   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.163  -5.455   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.979  -6.761   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.256  -8.121   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.518  -6.707   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.241  -5.347   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.425  -4.041   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.148  -2.682   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.886  -4.095   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.287   2.552   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.726   3.192   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.232   3.513   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.708   4.977   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.263   2.368   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.787   0.904   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.769   2.688   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   25                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25    2   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄O₃

Average Mass

428.6570 Da

Monoisotopic Mass

428.32905 Da

IUPAC Name

(1R,3aR,4R,5R,7aR)-1-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-octahydro-1H-indene-4,5-diol

Traditional Name

(1R,3aR,4R,5R,7aR)-1-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-hexahydro-1H-indene-4,5-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@]2([H])[C@]1(C)CC[C@@H](O)[C@@]2(O)CCC1=C(C)C=CC(O)=C1)[C@H](C)\C=C\[C@@H](C)C(C)C

InChI Identifier

InChI=1S/C28H44O3/c1-18(2)19(3)7-8-21(5)24-11-12-25-27(24,6)15-14-26(30)28(25,31)16-13-22-17-23(29)10-9-20(22)4/h7-10,17-19,21,24-26,29-31H,11-16H2,1-6H3/b8-7+/t19-,21-,24-,25-,26-,27-,28-/m1/s1

InChI Key

OMFMYOPWRZBPAD-ZXIHGUFVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.0, Chloroform-d, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.0, Chloroform-d, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-05	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Verrucella umbraculum		Not Available
Verrucella umbraculum	Linington's dataset npmrd_submissions_20220207	33966392

Chemical Taxonomy

Classification

Not classified

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	5.61	ALOGPS
logP	6.74	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	10.44	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.13 m³·mol⁻¹	ChemAxon
Polarizability	51.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

109107859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li J, Sun YL, Tang H, Su L, Zheng GL, Zhang W: Immunosuppressive 9,10-Secosteroids from the Gorgonian Verrucella umbraculum Collected in the South China Sea. J Nat Prod. 2021 May 28;84(5):1671-1675. doi: 10.1021/acs.jnatprod.1c00200. Epub 2021 May 9. [PubMed:33966392 ]
DOI: 10.1021/acs.jnatprod.1c00200
PMID: 33966392

Showing NP-Card for Verrucellol A (NP0044669)

MOL for NP0044669 (Verrucellol A)

3D MOL for NP0044669 (Verrucellol A)

3D SDF for NP0044669 (Verrucellol A)

3D-SDF for NP0044669 (Verrucellol A)

PDB for NP0044669 (Verrucellol A)

3D PDB for NP0044669 (Verrucellol A)

SMILES for NP0044669 (Verrucellol A)

INCHI for NP0044669 (Verrucellol A)

Structure for NP0044669 (Verrucellol A)

3D Structure for NP0044669 (Verrucellol A)