NP-MRD: Showing NP-Card for ent-Sandaracopimaradiene (NP0045578)

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Record Information

Version

2.0

Created at

2022-03-17 19:32:10 UTC

Updated at

2022-03-17 19:32:10 UTC

NP-MRD ID

NP0045578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-Sandaracopimaradiene

Description

Ent-Sandaracopimaradiene belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Thus, ent-sandaracopimaradiene is considered to be an isoprenoid lipid molecule. ent-Sandaracopimaradiene is found in Amphibolis antarctica, Araucaria columnaris, Cinnamomum burmannii, Cistus creticus, Cryptomeria japonica, Cupressus sempervirens, Diaporthe amygdali, Halocarpus biformis, Juniperus brevifolia, Kaempferia marginata, Manoao colensoi, Sitka spruce, Pilocarpus jaborandi, Pinus mugo subsp. Mugo , Pinus nigra, Pinus sylvestris, Pinus taeda, Prumnopitys andina, Prumnopitys ferruginoides, Salvia mellifera, Salvia parryi, Sequoiadendron giganteum, Thujopsis dolabrata, Xylia xylocarpa and Xylopia sericea . ent-Sandaracopimaradiene was first documented in 1966 (PMID: 5950472). Ent-Sandaracopimaradiene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 15277764) (PMID: 21323642).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007472D          

 22 24  0  0  0  0            999 V2000
 9998.932710000.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.792110001.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.505410001.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.076810001.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6488 9999.4808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.648010000.3061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9335 9999.8936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6480 9998.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3625 9999.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3625 9999.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.219310000.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5048 9999.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.362410001.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.647910001.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.076910000.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.076910001.1302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9324 9998.3560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5050 9999.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9334 9999.0687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.7031 9998.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7454 9998.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2191 9998.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  6  7  1  0  0  0  0
  6 10  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
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 15 16  1  0  0  0  0
 16  2  1  0  0  0  0
 16  4  1  1  0  0  0
 11  7  1  0  0  0  0
 14  6  1  0  0  0  0
 10 15  2  0  0  0  0
  6  5  1  6  0  0  0
  7  1  1  1  0  0  0
 19 17  1  6  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19  8  1  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@](C)(C=C)C=C1CC[C@@]1([H])C(C)(C)CCC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-6-19(4)13-10-16-15(14-19)8-9-17-18(2,3)11-7-12-20(16,17)5/h6,14,16-17H,1,7-13H2,2-5H3/t16-,17-,19-,20+/m0/s1

> <INCHI_KEY>
XDSYKASBVOZOAG-QGZVKYPTSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.4681

> <EXACT_MASS>
272.250401024

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.74907885152137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,4bS,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene

> <ALOGPS_LOGP>
5.81

> <JCHEM_LOGP>
5.8754919800000005

> <ALOGPS_LOGS>
-6.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
88.61759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.34e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-sandaracopimaradiene

> <JCHEM_VEBER_RULE>
1

$$$$

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    8664.6748668.009   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.0128669.548   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8671.3438668.775   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.6778670.314   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8666.0118665.697   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8666.0108667.238   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.6768666.468   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.0108664.158   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.3438664.928   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.3438666.468   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3438667.239   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.0098666.469   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3438669.546   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.0098668.776   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.6778667.236   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.6778668.776   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0    8664.6748663.598   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0    8662.0098664.928   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6768664.928   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8662.3798662.957   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8664.3258662.976   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8663.3428664.159   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    3   16                                                       
CONECT    3    2                                                            
CONECT    4   16                                                            
CONECT    5    6                                                            
CONECT    6    7   10   14    5                                             
CONECT    7    6   11    1   19                                             
CONECT    8    9   19                                                       
CONECT    9    8   10                                                       
CONECT   10    6    9   15                                                  
CONECT   11   12    7                                                       
CONECT   12   11   18                                                       
CONECT   13   14   16                                                       
CONECT   14   13    6                                                       
CONECT   15   16   10                                                       
CONECT   16   13   15    2    4                                             
CONECT   17   19                                                            
CONECT   18   22   12                                                       
CONECT   19   17   22    7    8                                             
CONECT   20   22                                                            
CONECT   21   22                                                            
CONECT   22   20   21   18   19                                             
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(-)-8(14),15-Isopimaradiene	ChEBI
(-)-Isopimara-8(14),15-diene	ChEBI
(-)-Sandaracopimaradiene	ChEBI
(4AS,4BS,7R,10as)-1,1,4a,7-tetramethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene	ChEBI
Sandaracopimaradiene	ChEBI
13-Isopimaradiene	PhytoBank
8(14),15-Isopimaradiene	PhytoBank
Sandaracopimara-8(14),15-diene	PhytoBank

Chemical Formula

C₂₀H₃₂

Average Mass

272.4681 Da

Monoisotopic Mass

272.25040 Da

IUPAC Name

(4aS,4bS,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene

Traditional Name

(+)-sandaracopimaradiene

CAS Registry Number

21738-16-9

SMILES

[H][C@]12CC[C@](C)(C=C)C=C1CC[C@@]1([H])C(C)(C)CCC[C@]21C

InChI Identifier

InChI=1S/C20H32/c1-6-19(4)13-10-16-15(14-19)8-9-17-18(2,3)11-7-12-20(16,17)5/h6,14,16-17H,1,7-13H2,2-5H3/t16-,17-,19-,20+/m0/s1

InChI Key

XDSYKASBVOZOAG-QGZVKYPTSA-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
Amphibolis antarctica	LOTUS Database	35616633
Araucaria columnaris	LOTUS Database	35616633
Cinnamomum burmanni	LOTUS Database	35616633
Cistus creticus	Plant	KNApSAcK
Cryptomeria japonica	LOTUS Database	35616633
Cupressus sempervirens	LOTUS Database	35616633
Fusicoccum amygdali	LOTUS Database	35616633
Halocarpus biformis	LOTUS Database	35616633
Juniperus brevifolia	LOTUS Database	35616633
Kaempferia marginata	LOTUS Database	35616633
Lagarostrobos colensoi	LOTUS Database	35616633
Oryza sativa	FooDB	KNAPSACK
Picea sitchensis	-	KNApSAcK
Pilocarpus jaborandi	LOTUS Database	35616633
Pinus mugo subsp. Mugo	Plant	KNApSAcK
Pinus nigra	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Pinus taeda	Plant	KNApSAcK
Prumnopitys andina	LOTUS Database	35616633
Prumnopitys ferruginoides	LOTUS Database	35616633
Salvia mellifera	LOTUS Database	35616633
Salvia parryi	LOTUS Database	35616633
Sequoiadendron giganteum	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633
Xylia xylocarpa	LOTUS Database	35616633
Xylopia sericea	Plant	KNApSAcK

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

Pimarane diterpenoid
Diterpenoid
Phenanthrene
Hydrophenanthrene
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diterpene (CHEBI:63708 )
Pimarane diterpenoids (LMPR0104080001 )

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	5.81	ALOGPS
logP	5.88	ChemAxon
logS	-6.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.62 m³·mol⁻¹	ChemAxon
Polarizability	34.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001468

KNApSAcK ID

Not Available

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

443469

PDB ID

Not Available

ChEBI ID

63708

Good Scents ID

Not Available

References

General References

Kenmoku H, Tanaka M, Ogiyama K, Kato N, Sassa T: Identification of (+)-phyllocladene, (--)-sandaracopimaradiene, and (+)-kaurene as new fungal metabolites from fusicoccin-producing Phomopsis amygdali F6. Biosci Biotechnol Biochem. 2004 Jul;68(7):1574-7. doi: 10.1271/bbb.68.1574. [PubMed:15277764 ]
Morrone D, Hillwig ML, Mead ME, Lowry L, Fulton DB, Peters RJ: Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals. Biochem J. 2011 May 1;435(3):589-95. doi: 10.1042/BJ20101429. [PubMed:21323642 ]
Johnston P, Sheppard RC, Stehr CE, Turner S: The synthesis of (-)-sandaracopimaradiene from androstane derivatives. J Chem Soc Perkin 1. 1966;20:1847-56. doi: 10.1039/j39660001847. [PubMed:5950472 ]

Showing NP-Card for ent-Sandaracopimaradiene (NP0045578)

MOL for NP0045578 (ent-Sandaracopimaradiene)

3D MOL for NP0045578 (ent-Sandaracopimaradiene)

3D SDF for NP0045578 (ent-Sandaracopimaradiene)

3D-SDF for NP0045578 (ent-Sandaracopimaradiene)

PDB for NP0045578 (ent-Sandaracopimaradiene)

3D PDB for NP0045578 (ent-Sandaracopimaradiene)

SMILES for NP0045578 (ent-Sandaracopimaradiene)

INCHI for NP0045578 (ent-Sandaracopimaradiene)

Structure for NP0045578 (ent-Sandaracopimaradiene)

3D Structure for NP0045578 (ent-Sandaracopimaradiene)