NP-MRD: Showing NP-Card for [(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol (NP0195444)

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Record Information

Version

2.0

Created at

2022-09-04 13:18:27 UTC

Updated at

2022-09-04 13:18:27 UTC

NP-MRD ID

NP0195444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol

Description

Candol B belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. [(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol is found in Amentotaxus formosana, Annona squamosa, Calocephalus knappii, Casearia corymbosa, Croton kongensis, Disynaphia multicrenulata, Espeletia tunjana, Lasianthaea fruticosa, Mikania vitifolia, Oyedaea verbesinoides, Ozothamnus argophyllus, Sagittaria trifolia, Sideritis canariensis, Sideritis candicans, Sideritis cystosiphon, Sideritis ferrensis, Sideritis infernalis, Sideritis soluta, Sideritis sventenii, Stevia lucida, Syzygiella tasmanica, Thlaspi arvense and Xylopia frutescens. [(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol was first documented in 2002 (PMID: 11942680). Candol B is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    4.4633    0.6744    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -0.2326    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3526   -0.2176    1.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -0.9855    0.5373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2500   -1.5833    1.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1294   -1.3180    0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589    0.1718    0.5068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5406    0.7035    0.5480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5652   -0.4002    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    1.0239    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7622   -0.0480    2.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7969    1.9436   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6925    2.5368   -0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.9683   -0.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.4375   -0.7231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0245    0.0488   -2.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0079   -0.1487   -0.6253 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4082   -0.9451   -1.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305   -1.0337   -1.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4193   -1.3995   -0.4408 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2769   -2.1605    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4942    1.5184    1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2679    0.5868   -0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071    0.8143    1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5600   -0.7881    2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3366   -2.6666    1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2499   -1.0954    2.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1629   -1.8285   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8819   -1.6668    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5985    0.6589    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0634   -1.1180   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4995    0.0077   -0.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8288   -0.9866    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8711    1.4521    2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554    1.8130    2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315    0.0983    3.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2210    2.7627    0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6841    1.7316   -0.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934    3.6376   -0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9204    2.4477   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    2.2111   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972    2.3349    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228   -1.0291   -2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792    0.3895   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    0.6796   -2.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    0.7318   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1968   -0.3773   -2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090   -1.9031   -1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2575   -1.8722   -2.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.0703   -2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211   -2.0167   -0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139   -2.9074   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -2.5860    1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21  4  1  0
  4  3  1  1
  3  2  1  0
  2  1  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  4 17  1  0
 15  7  1  0
 15 17  1  0
  2 20  1  0
 17 46  1  1
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 21 52  1  0
 21 53  1  0
  3 24  1  0
  3 25  1  0
  1 22  1  0
  1 23  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
M  END


  Mrv1652304302019202D          

 23 26  0  0  0  0            999 V2000
 9993.7632 9995.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0506 9993.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3361 9993.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3361 9992.6053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4757 9994.6792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7632 9993.4324    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7615 9995.0857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.7615 9994.2605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9994.4761 9993.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1906 9994.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0507 9995.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3362 9995.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3362 9994.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0507 9993.8482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.2720 9996.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3667 9996.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9364 9996.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4773 9995.5112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.7577 9996.8504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.9572 9995.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2120 9996.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1852 9995.0883    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.0291 9996.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  6  0  0  0
 14  8  1  0  0  0  0
  8  6  1  1  0  0  0
 11  7  1  0  0  0  0
  7  1  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 15  1  6  0  0  0
 19 15  1  6  0  0  0
 21 23  2  0  0  0  0
 18  7  1  0  0  0  0
 18  5  1  1  0  0  0
 10 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CO)CCC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O/c1-14-11-20-10-7-16-18(2,13-21)8-4-9-19(16,3)17(20)6-5-15(14)12-20/h15-17,21H,1,4-13H2,2-3H3/t15-,16-,17+,18-,19-,20-/m1/s1

> <INCHI_KEY>
TUJQVRFWMWRMIO-DAUOMPHXSA-N

> <FORMULA>
C20H32O

> <MOLECULAR_WEIGHT>
288.475

> <EXACT_MASS>
288.24531565

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.472277681656394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
4.335367008666668

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.592349954751715

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2275061297915997

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
87.4211

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 30-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-20         0                                  
HETATM    1  C   UNK     0    8655.0258659.040   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8653.6948653.631   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8652.3618654.403   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8652.3618652.863   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8656.3558656.734   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8655.0258654.407   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8655.0228657.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8655.0228655.953   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8656.3558655.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8657.6898655.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8653.6958658.263   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8652.3618657.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8652.3618655.953   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8653.6958655.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8657.8418659.271   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8656.1518659.813   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8657.2158660.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8656.3588658.288   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.7488660.787   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8659.1208658.039   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8659.5968659.503   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8657.6798657.498   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8661.1218659.710   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    4   14                                                       
CONECT    3   14                                                            
CONECT    4    2                                                            
CONECT    5   18                                                            
CONECT    6    8                                                            
CONECT    7    8   11    1   18                                             
CONECT    8    7    9   14    6                                             
CONECT    9    8   10                                                       
CONECT   10    9   22                                                       
CONECT   11   12    7                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    2    3    8                                             
CONECT   15   22   19                                                       
CONECT   16   17   18                                                       
CONECT   17   16   19                                                       
CONECT   18   16   22    7    5                                             
CONECT   19   17   21   15                                                  
CONECT   20   21   22                                                       
CONECT   21   19   20   23                                                  
CONECT   22   18   20   15   10                                             
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
(-)-Kaur-16-en-19-ol	HMDB
(4beta)-Kaur-16-en-18-ol	HMDB
(4β)-Kaur-16-en-18-ol	HMDB
16-Kauren-18-ol	HMDB
4beta-Kaur-16-en-19-ol	HMDB
4β-Kaur-16-en-19-ol	HMDB
Candol B	HMDB
Ent-18-Hydroxykaur-16-ene	HMDB
Kaur-16-en-19-ol	HMDB
ent-Kaur-16-en-19-ol	HMDB

Chemical Formula

C₂₀H₃₂O

Average Mass

288.4750 Da

Monoisotopic Mass

288.24532 Da

IUPAC Name

[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

Traditional Name

[(1S,4S,5S,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl]methanol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CO)CCC[C@@]21C

InChI Identifier

InChI=1S/C20H32O/c1-14-11-20-10-7-16-18(2,13-21)8-4-9-19(16,3)17(20)6-5-15(14)12-20/h15-17,21H,1,4-13H2,2-3H3/t15-,16-,17+,18-,19-,20-/m1/s1

InChI Key

TUJQVRFWMWRMIO-DAUOMPHXSA-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
Amentotaxus formosana	LOTUS Database	35616633
Annona squamosa	LOTUS Database	35616633
Calocephalus knappii	LOTUS Database	35616633
Casearia corymbosa	LOTUS Database	35616633
Croton kongensis	LOTUS Database	35616633
Disynaphia multicrenulata	LOTUS Database	35616633
Espeletia tunjana	LOTUS Database	35616633
Lasianthaea fruticosa	LOTUS Database	35616633
Mikania vitifolia	LOTUS Database	35616633
Oyedaea verbesinoides	LOTUS Database	35616633
Ozothamnus argophyllus	LOTUS Database	35616633
Sagittaria trifolia	LOTUS Database	35616633
Sideritis canariensis	LOTUS Database	35616633
Sideritis candicans	LOTUS Database	35616633
Sideritis cystosiphon	LOTUS Database	35616633
Sideritis ferrensis	LOTUS Database	35616633
Sideritis infernalis	LOTUS Database	35616633
Sideritis soluta	LOTUS Database	35616633
Sideritis sventenii	LOTUS Database	35616633
Stevia lucida	LOTUS Database	35616633
Syzygiella tasmanica	LOTUS Database	35616633
Thlaspi arvense	LOTUS Database	35616633
Xylopia frutescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
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	3.98	ALOGPS
logP	4.34	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.42 m³·mol⁻¹	ChemAxon
Polarizability	35.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036727

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015700

KNApSAcK ID

C00031762

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101289732

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Topcu G, Goren AC, Kilic T, Yildiz YK, Tumen G: Diterpenes from Sideritis trojana. Nat Prod Lett. 2002 Feb;16(1):33-7. doi: 10.1080/1057563029001/4827. [PubMed:11942680 ]
LOTUS database [Link]

Showing NP-Card for [(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol (NP0195444)

MOL for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

3D MOL for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

3D SDF for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

3D-SDF for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

PDB for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

3D PDB for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

SMILES for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

INCHI for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

Structure for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)

3D Structure for NP0195444 ([(1s,4s,5s,9s,10r,13r)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl]methanol)