NP-MRD: Showing NP-Card for (+)-Serratenediol (NP0073721)

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Record Information

Version

2.0

Created at

2022-04-28 18:56:34 UTC

Updated at

2022-04-28 18:56:34 UTC

NP-MRD ID

NP0073721

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Serratenediol

Description

Serratenediol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-Serratenediol is found in Lycopodium complanatum, Diphasiastrum complanatum L.Holub, Huperzia lucidula, Huperzia serrata , Lycopodiella inundata, Lycopodium clavatum, Lycopodium megastacyum, Lycopodium phlegmara, Lycopodium cernuum , Phlegmariurus megastachyus, Picea jezoensis and Pinus armandii. (+)-Serratenediol was first documented in 2009 (PMID: 20055158). Serratenediol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 28102682) (PMID: 27686269) (PMID: 22613212).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006252D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309272006252D          

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    8.3228   -7.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7097   -7.3557    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -8.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2789   -6.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3821   -7.0554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8262   -9.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  5  1  0  0  0  0
  2  5  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 14  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
  8 10  1  0  0  0  0
 11  9  1  0  0  0  0
 14 12  1  0  0  0  0
  1 15  1  0  0  0  0
 16 15  1  0  0  0  0
  2 16  1  0  0  0  0
 17  1  1  0  0  0  0
 18 17  1  0  0  0  0
 18  3  1  0  0  0  0
 18  6  1  0  0  0  0
 16  9  1  0  0  0  0
 11  4  1  0  0  0  0
 11 19  1  6  0  0  0
  9 20  1  1  0  0  0
 10 21  1  1  0  0  0
 16 22  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 27 31  1  0  0  0  0
 31 28  1  0  0  0  0
 31 30  1  0  0  0  0
 25 27  1  0  0  0  0
 28 26  1  0  0  0  0
 31 29  1  0  0  0  0
 28 23  1  0  0  0  0
 28 32  1  1  0  0  0
 26 33  1  6  0  0  0
 27 34  1  6  0  0  0
  6 23  1  0  0  0  0
 17 26  1  0  0  0  0
 17 35  1  1  0  0  0
 18 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0073721

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4([H])C(C)(C)[C@@H](O)CC[C@]34C)CC1=CC[C@@]1([H])C(C)(C)[C@@H](O)CC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O2/c1-26(2)21-10-8-19-18-28(5)15-12-22-27(3,4)25(32)14-17-30(22,7)23(28)11-9-20(19)29(21,6)16-13-24(26)31/h8,20-25,31-32H,9-18H2,1-7H3/t20-,21-,22-,23-,24-,25-,28-,29+,30-/m0/s1

> <INCHI_KEY>
FMUNNDDBCLRMSL-PIGMOXAFSA-N

> <FORMULA>
C30H50O2

> <MOLECULAR_WEIGHT>
442.728

> <EXACT_MASS>
442.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
55.433839382742576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,6R,8S,11R,12S,15S,16R,19S,21R)-1,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0^{3,12}.0^{6,11}.0^{16,21}]tricos-3-ene-8,19-diol

> <ALOGPS_LOGP>
6.10

> <JCHEM_LOGP>
6.316851312333334

> <ALOGPS_LOGS>
-6.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.55417898435636

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.4894333906316

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5197011827304127

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
133.54869999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.69e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R,8S,11R,12S,15S,16R,19S,21R)-1,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0^{3,12}.0^{6,11}.0^{16,21}]tricos-3-ene-8,19-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      10.488 -13.434   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.330 -16.139   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.718 -16.808   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.730 -16.733   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.201 -17.187   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.234 -17.187   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.189 -12.699   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.724 -12.223   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.509 -14.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.580 -13.254   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.364 -15.236   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.361 -14.848   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.677 -16.282   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.900 -14.760   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.948 -13.434   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.988 -14.638   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.448 -14.638   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.105 -16.139   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       5.044 -13.730   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       6.852 -15.707   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.115 -12.778   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       7.523 -13.170   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      13.706 -16.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.247 -12.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.712 -12.224   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.927 -14.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.856 -13.255   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.071 -15.237   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.074 -14.849   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.758 -16.283   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.536 -14.761   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      14.391 -13.731   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0      12.585 -15.708   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      17.321 -12.779   0.000  0.00  0.00           O+0
HETATM   35  H   UNK     0      11.913 -13.170   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0      10.876 -17.662   0.000  0.00  0.00           C+0
CONECT    1   15   17                                                       
CONECT    2    3    5   16                                                  
CONECT    3    2   18                                                       
CONECT    4    5   11                                                       
CONECT    5    4    2                                                       
CONECT    6   18   23                                                       
CONECT    7    8    9                                                       
CONECT    8    7   10                                                       
CONECT    9    7   11   16   20                                             
CONECT   10   14    8   21                                                  
CONECT   11   14    9    4   19                                             
CONECT   12   14                                                            
CONECT   13   14                                                            
CONECT   14   10   11   13   12                                             
CONECT   15    1   16                                                       
CONECT   16   15    2    9   22                                             
CONECT   17    1   18   26   35                                             
CONECT   18   17    3    6   36                                             
CONECT   19   11                                                            
CONECT   20    9                                                            
CONECT   21   10                                                            
CONECT   22   16                                                            
CONECT   23   28    6                                                       
CONECT   24   25   26                                                       
CONECT   25   24   27                                                       
CONECT   26   24   28   33   17                                             
CONECT   27   31   25   34                                                  
CONECT   28   31   26   23   32                                             
CONECT   29   31                                                            
CONECT   30   31                                                            
CONECT   31   27   28   30   29                                             
CONECT   32   28                                                            
CONECT   33   26                                                            
CONECT   34   27                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Serrat-14-ene-3 beta,21 alpha-diol	MeSH
Serrat-14-ene-3,21-diol	MeSH
3beta-Hydroxyserrat-14-en-21alpha-ol	PhytoBank
3β-Hydroxyserrat-14-en-21α-ol	PhytoBank
C(14a)-Homo-27-norgammacer-14-ene-3beta,21alpha-diol	PhytoBank
C(14a)-Homo-27-norgammacer-14-ene-3β,21α-diol	PhytoBank
Cathaya D	PhytoBank
Serrat-14-en-3beta,21alpha-diol	PhytoBank
Serrat-14-en-3β,21α-diol	PhytoBank
Pinusenediol	PhytoBank
Pinusendiol	PhytoBank

Chemical Formula

C₃₀H₅₀O₂

Average Mass

442.7280 Da

Monoisotopic Mass

442.38108 Da

IUPAC Name

(1S,6R,8S,11R,12S,15S,16R,19S,21R)-1,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0^{3,12}.0^{6,11}.0^{16,21}]tricos-3-ene-8,19-diol

Traditional Name

(1S,6R,8S,11R,12S,15S,16R,19S,21R)-1,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0^{3,12}.0^{6,11}.0^{16,21}]tricos-3-ene-8,19-diol

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4([H])C(C)(C)[C@@H](O)CC[C@]34C)CC1=CC[C@@]1([H])C(C)(C)[C@@H](O)CC[C@]21C

InChI Identifier

InChI=1S/C30H50O2/c1-26(2)21-10-8-19-18-28(5)15-12-22-27(3,4)25(32)14-17-30(22,7)23(28)11-9-20(19)29(21,6)16-13-24(26)31/h8,20-25,31-32H,9-18H2,1-7H3/t20-,21-,22-,23-,24-,25-,28-,29+,30-/m0/s1

InChI Key

FMUNNDDBCLRMSL-PIGMOXAFSA-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
Diphasiastrum complanatum	Plant	KNApSAcK
Diphasiastrum complanatum L.Holub	Plant	KNApSAcK
Huperzia lucidula	LOTUS Database	35616633
Huperzia serrata	Plant	KNApSAcK
Lycopodiella inundata	LOTUS Database	35616633
Lycopodium clavatum	LOTUS Database	35616633
Lycopodium megastacyum	Plant	KNApSAcK
Lycopodium phlegmara	Plant	KNApSAcK
Palhinhaea cernua	Plant	KNApSAcK
Phlegmariurus megastachyus	LOTUS Database	35616633
Picea jezoensis	LOTUS Database	35616633
Pinus armandii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	6.1	ALOGPS
logP	6.32	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.52	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	0	ChemAxon
Refractivity	133.55 m³·mol⁻¹	ChemAxon
Polarizability	55.43 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

Not Available

Chemspider ID

144608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164947

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Deng TZ, Ai Y, Chen Y, Yang GZ: Triterpenoid from Lycopodium obscurum L. Yao Xue Xue Bao. 2009 Aug;44(8):891-4. [PubMed:20055158 ]
Saga Y, Araki T, Araya H, Saito K, Yamazaki M, Suzuki H, Kushiro T: Identification of Serratane Synthase Gene from the Fern Lycopodium clavatum. Org Lett. 2017 Feb 3;19(3):496-499. doi: 10.1021/acs.orglett.6b03659. Epub 2017 Jan 19. [PubMed:28102682 ]
Armijos C, Gilardoni G, Amay L, Lozano A, Bracco F, Ramirez J, Bec N, Larroque C, Finzi PV, Vidari G: Phytochemical and ethnomedicinal study of Huperzia species used in the traditional medicine of Saraguros in Southern Ecuador; AChE and MAO inhibitory activity. J Ethnopharmacol. 2016 Dec 4;193:546-554. doi: 10.1016/j.jep.2016.09.049. Epub 2016 Sep 28. [PubMed:27686269 ]
Ham YM, Yoon WJ, Park SY, Jung YH, Kim D, Jeon YJ, Wijesinghe WA, Kang SM, Kim KN: Investigation of the component of Lycopodium serratum extract that inhibits proliferation and mediates apoptosis of human HL-60 leukemia cells. Food Chem Toxicol. 2012 Aug;50(8):2629-34. doi: 10.1016/j.fct.2012.05.019. Epub 2012 May 18. [PubMed:22613212 ]

Showing NP-Card for (+)-Serratenediol (NP0073721)

MOL for NP0073721 ((+)-Serratenediol)

3D MOL for NP0073721 ((+)-Serratenediol)

3D SDF for NP0073721 ((+)-Serratenediol)

3D-SDF for NP0073721 ((+)-Serratenediol)

PDB for NP0073721 ((+)-Serratenediol)

3D PDB for NP0073721 ((+)-Serratenediol)

SMILES for NP0073721 ((+)-Serratenediol)

INCHI for NP0073721 ((+)-Serratenediol)

Structure for NP0073721 ((+)-Serratenediol)

3D Structure for NP0073721 ((+)-Serratenediol)