NP-MRD: Showing NP-Card for 24-Methylenecycloartan-3-ol (NP0048300)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:16 UTC

Updated at

2022-03-17 20:54:16 UTC

NP-MRD ID

NP0048300

Secondary Accession Numbers

None

Natural Product Identification

Common Name

24-Methylenecycloartan-3-ol

Description

24-Methylenecycloartan-3-ol belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. 24-Methylenecycloartan-3-ol is found in Actaea simplex, Amaranthus retroflexus, Amaranthus tricolor, Ammocharis coranica, Arabidopsis thaliana, Archidendron chevalieri, Arctium lappa, Avena sativa, Beta vulgaris, Camellia oleifera, Camellia sasanqua, Carthamus tinctorius, Citrus aurantium, Clerodendrum splendens, Costus tonkinensis, Diplopterygium glaucum, Dracaena cinnabari, Elaeagnus angustifolia, Eucalyptus microcorys, Euphorbia aleppica, Euphorbia antiquorum, Euphorbia boetica, Euphorbia cyparissias, Euphorbia ebracteolata, Euphorbia esula, Euphorbia peplus , Euphorbia guyoniana, Euphorbia heteradena, Euphorbia iberica, Euphorbia kansui, Euphorbia lactea, Euphorbia lathyris , Euphorbia myrsinites, Euphorbia nicaeensis, Euphorbia oxyphylla, Euphorbia piscatoria, Euphorbia retusa, Euphorbia rigida, Euphorbia segetalis , Euphorbia seguieriana, Ficus fistulosa, Gleichenia japonica, Helianthus annuus, Hippophae rhamnoides, Hoya australis, Ixeris chinensis, Lagerstroemia speciosa, Larix gmelinii, Larix kaempferi, Larix kaempferi (Lamb.) Carr, Lophostemon confertus, Mangifera indica, Melia azedarach, Musa paradisiaca, Neolitsea sericea, Nicotiana tabacum, Nigella sativa , Olea europaea, Ononis natrix, Paeonia emodi, Panax ginseng, Panax quinquefolius, Pandanus boninensis, Pentatropis spiralis, Phytolacca americana, Pisum sativum, Polypodium formosanum, Populus tremuloides, Salvia breviflora, Salvia nemorosa, Salvia sylvestris, Sambucus nigra, Scutellaria discolor, Sesamum radiatum, Sideritis discolor, Solanum chacoense Bitt., Solanum melongena, Sparganium eurycarpum, Sparganium stoloniferum, Stauntonia hexaphylla, Symphoricarpos albus, Tillandsia recurvata, Tillandsia usneoides, Trichilia claussenii, Ulva intestinalis, Ulva lactuca, Vahlia capensis, Vigna angularis, Vitellaria paradoxa, Xanthoceras sorbifolia , Zantedeschia aethiopica and Zea mays. 24-Methylenecycloartan-3-ol was first documented in 1958 (PMID: 13573499). 24-Methylenecycloartan-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 10691725) (PMID: 14622971) (PMID: 17337022).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007292D          

 35 39  0  0  0  0            999 V2000
 9999.9762 9998.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.839110000.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9998.0653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.976210001.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.263810000.1351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1260 9999.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9999.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264410000.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549910000.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5499 9999.7278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2644 9999.3154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8374 9999.3069    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5519 9998.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2664 9998.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6055 9997.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6477 9997.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8448 9998.4795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.4078 9998.4829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1223 9998.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.978910000.5528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9788 9999.7278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.7635 9999.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.248310000.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763510000.8078    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763510001.6328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479210002.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192810001.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510002.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210001.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337810002.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510002.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049910002.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210001.2182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8347 9997.7681    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
  6 12  1  0  0  0  0
 10 12  1  0  0  0  0
 14 11  1  0  0  0  0
 11  5  1  1  0  0  0
 18 19  1  0  0  0  0
 19 16  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
  7 18  1  0  0  0  0
 12 17  1  0  0  0  0
 17 13  1  0  0  0  0
 18  3  1  1  0  0  0
 12  2  1  1  0  0  0
 10  2  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 34  1  6  0  0  0
 25 26  1  0  0  0  0
 25 33  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 32  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
  8 20  1  0  0  0  0
 11 21  1  0  0  0  0
 20  4  1  1  0  0  0
 21  1  1  6  0  0  0
 17 35  1  6  0  0  0
M  END


  Mrv1652309272007292D          

 35 39  0  0  0  0            999 V2000
 9999.9762 9998.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.839110000.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9998.0653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.976210001.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.263810000.1351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1260 9999.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9999.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264410000.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.549910000.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5499 9999.7278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2644 9999.3154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8374 9999.3069    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5519 9998.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2664 9998.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6055 9997.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6477 9997.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8448 9998.4795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.4078 9998.4829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1223 9998.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.978910000.5528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9788 9999.7278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.7635 9999.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.248310000.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763510000.8078    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.763510001.6328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.479210002.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192810001.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510002.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210001.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337810002.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510002.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049910002.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210001.2182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8347 9997.7681    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
  6 12  1  0  0  0  0
 10 12  1  0  0  0  0
 14 11  1  0  0  0  0
 11  5  1  1  0  0  0
 18 19  1  0  0  0  0
 19 16  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
  7 18  1  0  0  0  0
 12 17  1  0  0  0  0
 17 13  1  0  0  0  0
 18  3  1  1  0  0  0
 12  2  1  1  0  0  0
 10  2  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 34  1  6  0  0  0
 25 26  1  0  0  0  0
 25 33  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 32  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
  8 20  1  0  0  0  0
 11 21  1  0  0  0  0
 20  4  1  1  0  0  0
 21  1  1  6  0  0  0
 17 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0048300

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C)[C@H](C)CCC(=C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H52O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h20,22-26,32H,3,9-19H2,1-2,4-8H3/t22-,23-,24+,25+,26+,28-,29+,30-,31+/m1/s1

> <INCHI_KEY>
BDHQMRXFDYJGII-UEBIAWITSA-N

> <FORMULA>
C31H52O

> <MOLECULAR_WEIGHT>
440.744

> <EXACT_MASS>
440.401816286

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
56.664181224475705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

> <ALOGPS_LOGP>
6.52

> <JCHEM_LOGP>
7.892615146

> <ALOGPS_LOGS>
-6.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489408976606935

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351325136321267

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
135.50929999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

> <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    8666.6228664.614   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6338666.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6368663.055   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8666.6228669.248   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8665.2928666.919   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8661.3028666.143   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.9688665.373   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.2948668.469   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.9608667.699   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.9608666.159   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.2948665.389   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.6308665.373   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.9648663.063   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2978663.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.3308661.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.2768661.878   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.6448663.828   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8659.9618663.835   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8661.2958663.065   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6278667.699   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.6278666.159   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.0928665.683   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.9978666.929   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0928668.175   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.0928669.715   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.4288670.481   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.7608669.715   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.0968670.481   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4328669.715   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8674.7648670.481   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8673.4328668.175   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8672.0968672.021   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8666.7608670.481   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0    8669.4288668.941   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0    8662.6258662.500   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   12   10                                                       
CONECT    3   18                                                            
CONECT    4   20                                                            
CONECT    5   11                                                            
CONECT    6    7   12                                                       
CONECT    7    6   18                                                       
CONECT    8    9   20                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12    2                                             
CONECT   11   10   14    5   21                                             
CONECT   12    6   10   17    2                                             
CONECT   13   14   17                                                       
CONECT   14   13   11                                                       
CONECT   15   19                                                            
CONECT   16   19                                                            
CONECT   17   19   12   13   35                                             
CONECT   18   19    7    3                                                  
CONECT   19   18   16   15   17                                             
CONECT   20   21   24    8    4                                             
CONECT   21   20   22   11    1                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   25   34   20   23                                             
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33   25                                                            
CONECT   34   24                                                            
CONECT   35   17                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
(3beta,9beta)-24-Methylene-9,19-cyclolanostan-3-ol	ChEBI
24(28)-Methylenecycloartanol	ChEBI
24-Methylene cycloartanol	ChEBI
24-Methylene-9beta,19-cyclo-lanostan-3beta-ol	ChEBI
24-Methylene-cycloartanol	ChEBI
24-Methylenecycloartan-3beta-ol	ChEBI
4alpha,4beta,14alpha-Trimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-3beta-ol	Kegg
24-Methylenecycloartanol	Kegg
(3b,9b)-24-Methylene-9,19-cyclolanostan-3-ol	Generator
(3Β,9β)-24-methylene-9,19-cyclolanostan-3-ol	Generator
24-Methylene-9b,19-cyclo-lanostan-3b-ol	Generator
24-Methylene-9β,19-cyclo-lanostan-3β-ol	Generator
24-Methylenecycloartan-3b-ol	Generator
24-Methylenecycloartan-3β-ol	Generator
4a,4b,14a-Trimethyl-9b,19-cyclo-5a-ergost-24(24(1))-en-3b-ol	Generator
4Α,4β,14α-trimethyl-9β,19-cyclo-5α-ergost-24(24(1))-en-3β-ol	Generator
(3beta)-24-Methylene-9,19-cyclolanostan-3-ol	PhytoBank
(3β)-24-Methylene-9,19-cyclolanostan-3-ol	PhytoBank
24-Methylencycloartan-3beta-ol	PhytoBank
24-Methylencycloartan-3β-ol	PhytoBank
24-Methylene-9,19-cyclolanostan-3beta-ol	PhytoBank
24-Methylene-9,19-cyclolanostan-3β-ol	PhytoBank
24-Methylidenecycloartanol	PhytoBank
3beta-Hydroxy-24-methylenecycloartane	PhytoBank
3β-Hydroxy-24-methylenecycloartane	PhytoBank
9,19-Cyclo-24-methylenelanostan-3beta-ol	PhytoBank
9,19-Cyclo-24-methylenelanostan-3β-ol	PhytoBank
24-Methylenecycloartenol	PhytoBank

Chemical Formula

C₃₁H₅₂O

Average Mass

440.7440 Da

Monoisotopic Mass

440.40182 Da

IUPAC Name

(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

Traditional Name

(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

CAS Registry Number

1449-09-8

SMILES

[H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C)[C@H](C)CCC(=C)C(C)C

InChI Identifier

InChI=1S/C31H52O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h20,22-26,32H,3,9-19H2,1-2,4-8H3/t22-,23-,24+,25+,26+,28-,29+,30-,31+/m1/s1

InChI Key

BDHQMRXFDYJGII-UEBIAWITSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actaea simplex	LOTUS Database	35616633
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Amaranthus retroflexus	LOTUS Database	35616633
Amaranthus tricolor	LOTUS Database	35616633
Ammocharis coranica	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Archidendron chevalieri	LOTUS Database	35616633
Arctium lappa	LOTUS Database	35616633
Avena sativa	LOTUS Database	35616633
Beta vulgaris	LOTUS Database	35616633
Brassica oleracea var. italica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Camellia oleifera	LOTUS Database	35616633
Camellia sasanqua	LOTUS Database	35616633
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Carthamus tinctorius	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Clerodendrum splendens	LOTUS Database	35616633
Cocos nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea arabica L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Costus tonkinensis	LOTUS Database	35616633
Cucumis melo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Diplopterygium glaucum	LOTUS Database	35616633
Dracaena cinnabari	LOTUS Database	35616633
Elaeagnus angustifolia	LOTUS Database	35616633
Eucalyptus microcorys	LOTUS Database	35616633
Euphorbia aleppica	LOTUS Database	35616633
Euphorbia antiquorum	LOTUS Database	35616633
Euphorbia boetica	LOTUS Database	35616633
Euphorbia cyparissias	LOTUS Database	35616633
Euphorbia ebracteolata	LOTUS Database	35616633
Euphorbia esula	LOTUS Database	35616633
Euphorbia Euphorbia peplus	Plant	KNApSAcK
Euphorbia guyoniana	Plant	KNApSAcK
Euphorbia heteradena	LOTUS Database	35616633
Euphorbia iberica	LOTUS Database	35616633
Euphorbia kansui	LOTUS Database	35616633
Euphorbia lactea	LOTUS Database	35616633
Euphorbia lathyris	Plant	KNApSAcK
Euphorbia myrsinites	LOTUS Database	35616633
Euphorbia nicaeensis	LOTUS Database	35616633
Euphorbia oxyphylla	LOTUS Database	35616633
Euphorbia piscatoria	LOTUS Database	35616633
Euphorbia retusa	LOTUS Database	35616633
Euphorbia rigida	LOTUS Database	35616633
Euphorbia segetalis	Plant	KNApSAcK
Euphorbia seguieriana	LOTUS Database	35616633
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ficus fistulosa	LOTUS Database	35616633
Gleichenia japonica	LOTUS Database	35616633
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus annuus	LOTUS Database	35616633
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hippophae rhamnoides	LOTUS Database	35616633
Hoya australis	LOTUS Database	35616633
Ixeris chinensis	LOTUS Database	35616633
Lagerstroemia speciosa	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Larix kaempferi (Lamb.) Carr	Plant	KNApSAcK
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lophostemon confertus	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Melia azedarach	LOTUS Database	35616633
Momordica charantia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Musa paradisiaca	LOTUS Database	35616633
Musa x paradisiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Neolitsea sericea	LOTUS Database	35616633
Nicotiana tabacum	LOTUS Database	35616633
Nigella sativa	Plant	KNApSAcK
Oenothera biennis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Olea europaea	LOTUS Database	35616633
Ononis natrix	LOTUS Database	35616633
Oryza sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Paeonia emodi	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Panax quinquefolius	LOTUS Database	35616633
Pandanus boninensis	LOTUS Database	35616633
Pentatropis spiralis	LOTUS Database	35616633
Persea americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phytolacca americana	LOTUS Database	35616633
Pisum sativum	LOTUS Database	35616633
Polypodium formosanum	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633
Prunus cerasus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus dulcis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia breviflora	Plant	KNApSAcK
Salvia nemorosa	Plant	KNApSAcK
Salvia x sylvestris	LOTUS Database	35616633
Sambucus nigra	LOTUS Database	35616633
Scutellaria discolor	LOTUS Database	35616633
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sesamum radiatum	LOTUS Database	35616633
Sideritis discolor	Plant	KNApSAcK
Solanum chacoense Bitt.	Plant	KNApSAcK
Solanum melongena	LOTUS Database	35616633
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sparganium eurycarpum	LOTUS Database	35616633
Sparganium stoloniferum	Plant	KNApSAcK
Stauntonia hexaphylla	LOTUS Database	35616633
Symphoricarpos albus	LOTUS Database	35616633
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tillandsia recurvata	LOTUS Database	35616633
Tillandsia usneoides	LOTUS Database	35616633
Trichilia claussenii	LOTUS Database	35616633
Ulva intestinalis	LOTUS Database	35616633
Ulva lactuca	LOTUS Database	35616633
Vahlia capensis	LOTUS Database	35616633
Vigna angularis	LOTUS Database	35616633
Vitellaria paradoxa	LOTUS Database	35616633
Xanthoceras sorbifolium	Plant	KNApSAcK
Zantedeschia aethiopica	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triterpenoid (CHEBI:1307 )
Cycloartanols and derivatives (C08830 )
Cycloartane (C08830 )

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	6.52	ALOGPS
logP	7.89	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.84	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	5	ChemAxon
Refractivity	135.51 m³·mol⁻¹	ChemAxon
Polarizability	56.66 Å³	ChemAxon
Number of Rings	5	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

FDB014438

KNApSAcK ID

C00003661

Chemspider ID

Not Available

KEGG Compound ID

C08830

BioCyc ID

CPD-696

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94204

PDB ID

Not Available

ChEBI ID

1307

Good Scents ID

Not Available

References

General References

Giner JL, Berkowitz JD, Andersson T: Nonpolar components of the latex of Euphorbia peplus. J Nat Prod. 2000 Feb;63(2):267-9. doi: 10.1021/np990081g. [PubMed:10691725 ]
OHTA G, SHIMIZU M: A new triterpenoid alcohol, 24-methylenecycloartanol, as its ferulate, from rice bran oil. Chem Pharm Bull (Tokyo). 1958 Jun;6(3):325-6. doi: 10.1248/cpb.6.325. [PubMed:13573499 ]
Zhou W, Nes WD: Sterol methyltransferase2: purification, properties, and inhibition. Arch Biochem Biophys. 2003 Dec 1;420(1):18-34. doi: 10.1016/j.abb.2003.08.029. [PubMed:14622971 ]
Haba H, Lavaud C, Harkat H, Alabdul Magid A, Marcourt L, Benkhaled M: Diterpenoids and triterpenoids from Euphorbia guyoniana. Phytochemistry. 2007 May;68(9):1255-60. doi: 10.1016/j.phytochem.2007.01.017. Epub 2007 Mar 6. [PubMed:17337022 ]

Showing NP-Card for 24-Methylenecycloartan-3-ol (NP0048300)

MOL for NP0048300 (24-Methylenecycloartan-3-ol)

3D MOL for NP0048300 (24-Methylenecycloartan-3-ol)

3D SDF for NP0048300 (24-Methylenecycloartan-3-ol)

3D-SDF for NP0048300 (24-Methylenecycloartan-3-ol)

PDB for NP0048300 (24-Methylenecycloartan-3-ol)

3D PDB for NP0048300 (24-Methylenecycloartan-3-ol)

SMILES for NP0048300 (24-Methylenecycloartan-3-ol)

INCHI for NP0048300 (24-Methylenecycloartan-3-ol)

Structure for NP0048300 (24-Methylenecycloartan-3-ol)

3D Structure for NP0048300 (24-Methylenecycloartan-3-ol)