NP-MRD: Showing NP-Card for 2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene (NP0078189)

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Record Information

Version

2.0

Created at

2022-04-28 23:18:36 UTC

Updated at

2022-04-28 23:18:36 UTC

NP-MRD ID

NP0078189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene

Description

(1S,2R,7S,11S,12R,13S)-3-Methylene-7,13,14-trimethyl-2,13-ethanobicyclo[8.3.1]Tetradeca-10(14)-ene-11,12-diol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene is found in Nasutitermes costalis, Nasutitermes guayanae and Nasutitermes nigriceps. Based on a literature review very few articles have been published on (1S,2R,7S,11S,12R,13S)-3-Methylene-7,13,14-trimethyl-2,13-ethanobicyclo[8.3.1]Tetradeca-10(14)-ene-11,12-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292201182D          

 22 24  0  0  1  0            999 V2000
    3.4731    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7433   -0.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9557    0.1869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9844    1.0159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6375    1.4992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3427    1.1128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0160    1.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    2.3223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    1.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804    0.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1062    0.0527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0387    0.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7671    1.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7843    1.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3698    2.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    2.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035    2.4337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7949    1.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0549    1.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    3.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9047    1.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8117   -0.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 17 20  1  6  0  0  0
  4 21  1  1  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCCC(=C)[C@@H]2CC[C@@]3(C)[C@@H]2C(C)=C(CC1)[C@H](O)[C@@H]3O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-12-6-5-7-13(2)15-10-11-20(4)17(15)14(3)16(9-8-12)18(21)19(20)22/h12,15,17-19,21-22H,2,5-11H2,1,3-4H3/t12-,15-,17+,18-,19-,20-/m0/s1

> <INCHI_KEY>
KKUYFJMPBSOTQV-HUWKJKRASA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.474

> <EXACT_MASS>
304.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
35.72085295636735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,6S,10S,11R,12S,15S)-6,12,16-trimethyl-2-methylidenetricyclo[7.5.2.0^{12,15}]hexadec-9(16)-ene-10,11-diol

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.769862638

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.755564474674127

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.335506564165392

> <JCHEM_PKA_STRONGEST_BASIC>
-3.376254440416731

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
91.00679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S,10S,11R,12S,15S)-6,12,16-trimethyl-2-methylidenetricyclo[7.5.2.0^{12,15}]hexadec-9(16)-ene-10,11-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.483   0.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.121  -0.278   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.651   0.349   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.704   1.896   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.923   2.799   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.240   2.077   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.496   2.967   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.819   4.335   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.334   2.548   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.083   1.305   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.065   0.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.939   1.709   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.299   2.432   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.464   3.418   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.557   4.648   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.177   4.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.793   4.543   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.084   3.474   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.569   1.873   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.475   5.924   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.555   3.429   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.248  -1.813   0.000  0.00  0.00           C+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    9   21                                             
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    1                                                       
CONECT   20   17                                                            
CONECT   21    4                                                            
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₂

Average Mass

304.4740 Da

Monoisotopic Mass

304.24023 Da

IUPAC Name

(1R,6S,10S,11R,12S,15S)-6,12,16-trimethyl-2-methylidenetricyclo[7.5.2.0^{12,15}]hexadec-9(16)-ene-10,11-diol

Traditional Name

(1R,6S,10S,11R,12S,15S)-6,12,16-trimethyl-2-methylidenetricyclo[7.5.2.0^{12,15}]hexadec-9(16)-ene-10,11-diol

CAS Registry Number

Not Available

SMILES

C[C@H]1CCCC(=C)[C@@H]2CC[C@@]3(C)[C@@H]2C(C)=C(CC1)[C@H](O)[C@@H]3O

InChI Identifier

InChI=1S/C20H32O2/c1-12-6-5-7-13(2)15-10-11-20(4)17(15)14(3)16(9-8-12)18(21)19(20)22/h12,15,17-19,21-22H,2,5-11H2,1,3-4H3/t12-,15-,17+,18-,19-,20-/m0/s1

InChI Key

KKUYFJMPBSOTQV-HUWKJKRASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nasutitermes costalis	LOTUS Database	35616633
Nasutitermes guayanae	Animalia	KNApSAcK
Nasutitermes nigriceps	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Trinervitane or kempane diterpenoid
Diterpenoid
Secondary alcohol
1,2-diol
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	3.8	ALOGPS
logP	3.77	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	-3.4	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	91.01 m³·mol⁻¹	ChemAxon
Polarizability	35.72 Å³	ChemAxon
Number of Rings	3	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

9510674

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11335728

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene (NP0078189)

MOL for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

3D MOL for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

3D SDF for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

3D-SDF for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

PDB for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

3D PDB for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

SMILES for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

INCHI for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

Structure for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)

3D Structure for NP0078189 (2alpha,3alpha-Dihydroxy-1(15),8(19)-trinervitadiene)