NP-MRD: Showing NP-Card for (1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol (NP0266591)

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Record Information

Version

2.0

Created at

2022-09-08 10:58:58 UTC

Updated at

2022-09-08 10:58:58 UTC

NP-MRD ID

NP0266591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol

Description

Caryolan-1,9beta-diol belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). (1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol is found in Cyperus longus. (1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol was first documented in 2015 (PMID: 26344038). Based on a literature review very few articles have been published on caryolan-1,9beta-diol (PMID: 33140544).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.6838    0.0827   -1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793   -0.1636   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1453    0.1562    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -1.5738   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679   -0.8974    0.4713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3123    0.2883   -0.3999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7137    1.4893    0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6324    1.6688   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7434    0.8926    0.0913 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5377    1.8609    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3744   -0.2556    0.9698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016   -1.2937    0.2460 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7365   -2.4972    0.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812   -1.4869   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514   -1.1388   -1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6952    0.3361   -0.9767 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9826    0.4505   -0.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6564   -0.4081   -0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474   -0.1913   -2.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8748    1.1774   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0558   -0.7179    2.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2436    0.3744    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673    1.0611    1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263   -1.8137   -1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5745   -2.3135    0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430   -0.5864    1.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1559    0.1616   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    1.4378    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310    2.3944   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515    2.7748   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351    1.4163   -1.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702    1.5210    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595    2.8346    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9722    2.0439    1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -0.7633    1.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    0.0716    1.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685   -2.3710    1.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9235   -2.5830   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -0.9579   -1.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0190   -1.7821   -0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8047   -1.3647   -2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    0.9339   -1.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352   -0.2682    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  6  2  1  0
 16  9  1  0
 12  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  6
 17 43  1  0
M  END


  Mrv1652309082212592D          

 17 19  0  0  1  0            999 V2000
    4.5339    1.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224    1.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712    2.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737    0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.6368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9110    1.4483    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5033    2.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7300    2.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9529    2.1761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4269    2.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979    1.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1266    0.1108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4035   -0.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3016    0.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6733    0.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    1.4644    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2759    1.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0266591

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-13(2)8-11-10(13)4-6-14(3)9-15(11,17)7-5-12(14)16/h10-12,16-17H,4-9H2,1-3H3/t10-,11+,12-,14-,15+/m0/s1

> <INCHI_KEY>
SFJOMLIUSIKKRA-CUZKYEQNSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.371

> <EXACT_MASS>
238.193280077

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.27673328793252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,8S,9S)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecane-1,9-diol

> <JCHEM_LOGP>
2.196222674333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.931980188317752

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.298007985875216

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9291348809027538

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
68.0174

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8S,9S)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecane-1,9-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.463   2.148   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.949   2.426   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.226   3.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.671   0.911   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.156   1.189   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.434   2.703   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.673   4.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.229   4.579   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.779   4.062   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.797   5.248   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.356   2.408   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.970   0.207   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.487  -1.244   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.430   0.217   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.257   1.215   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.000   2.734   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.515   3.011   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
Caryolan-1,9b-diol	Generator
Caryolan-1,9β-diol	Generator

Chemical Formula

C₁₅H₂₆O₂

Average Mass

238.3710 Da

Monoisotopic Mass

238.19328 Da

IUPAC Name

(1R,2R,5S,8S,9S)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecane-1,9-diol

Traditional Name

(1R,2R,5S,8S,9S)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecane-1,9-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H26O2/c1-13(2)8-11-10(13)4-6-14(3)9-15(11,17)7-5-12(14)16/h10-12,16-17H,4-9H2,1-3H3/t10-,11+,12-,14-,15+/m0/s1

InChI Key

SFJOMLIUSIKKRA-CUZKYEQNSA-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
Cyperus longus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Hydrocarbon derivative
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	2.2	ChemAxon
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-2.9	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	68.02 m³·mol⁻¹	ChemAxon
Polarizability	28.28 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

C00022010

Chemspider ID

23327608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559977

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rodriguez-Chavez JL, Coballase-Urrutia E, Sicilia-Argumedo G, Ramirez-Apan T, Delgado G: Toxicological evaluation of the natural products and some semisynthetic derivatives of Heterotheca inuloides Cass (Asteraceae). J Ethnopharmacol. 2015 Dec 4;175:256-65. doi: 10.1016/j.jep.2015.08.055. Epub 2015 Sep 5. [PubMed:26344038 ]
Wu J, Zhu Y, Zhang M, Li H, Sun P: Micaryolanes A and B, Two New Caryolane-Type Sesquiterpenoids from Marine Streptomyces sp. AH25. Chem Biodivers. 2020 Dec;17(12):e2000769. doi: 10.1002/cbdv.202000769. Epub 2020 Nov 26. [PubMed:33140544 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol (NP0266591)

MOL for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

3D MOL for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

3D SDF for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

3D-SDF for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

PDB for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

3D PDB for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

SMILES for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

INCHI for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

Structure for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)

3D Structure for NP0266591 ((1r,2r,5s,8s,9s)-4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol)