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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:08:01 UTC

Update Date

2022-03-07 02:57:01 UTC

HMDB ID

HMDB0041446

Secondary Accession Numbers

HMDB41446

Metabolite Identification

Common Name

Rosmaricine

Description

Rosmaricine belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Rosmaricine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0041446
     RDKit          3D
Rosmaricine
 52 55  0  0  0  0  0  0  0  0999 V2000
    5.2371    0.2292   -0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100    0.2509    0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2198   -0.3320    1.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0666    0.0009    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2338    1.0603   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    0.8777   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388   -0.3942    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489   -1.4459    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769   -2.6570    0.7652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135   -1.2091    0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014   -2.2475    0.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813   -0.5231   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987   -1.8837   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351   -1.8436   -0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7092   -0.5218   -0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301    0.3496    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    1.6109    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208   -0.3629    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446    0.5994    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605    1.7401   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    1.1066   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854   -0.1841   -1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.9799   -2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    2.0342   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311    2.8997   -1.4187 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -0.2090   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0597   -0.5552   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    1.1681   -1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6006    1.4328    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2519    0.1190    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378    0.0666    2.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.4146    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176    1.9935   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148   -3.4995    1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762   -3.1662    1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -2.5920   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698   -2.1919    0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -2.1217   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771   -2.6378   -0.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655    0.0477   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8158   -0.7320   -0.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489    1.2627    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    2.0330   -0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367    2.3290    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8843   -0.5610    2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977    0.1883    2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1833   -1.3744    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    0.8531    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014    2.6220   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012    2.6636    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9043    2.3704   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624    3.7308   -1.6510 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 20 24  1  0
 24 25  1  0
 10  4  1  0
 19 12  1  0
 24  6  1  0
 22 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
M  END


  Mrv0541 02241219042D          

 25 28  0  0  0  0            999 V2000
    2.2112   -1.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444   -1.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -1.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264   -0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189    1.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189    1.8865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775    0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700    1.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112    1.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775   -1.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2112   -0.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600   -0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112   -0.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031   -0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031    0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7956    1.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7956   -0.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549   -1.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5624   -1.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3857   -0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    0.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 20  1  0  0  0  0
  4 24  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  6 25  1  0  0  0  0
  7  8  1  0  0  0  0
  7 19  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041446

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C(O)C(O)=C2C(=C1)C(N)C1OC(=O)C22CCCC(C)(C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H27NO4/c1-9(2)10-8-11-12(15(23)14(10)22)20-7-5-6-19(3,4)17(20)16(13(11)21)25-18(20)24/h8-9,13,16-17,22-23H,5-7,21H2,1-4H3

> <INCHI_KEY>
NFXKGLBUURRKEA-UHFFFAOYSA-N

> <FORMULA>
C20H27NO4

> <MOLECULAR_WEIGHT>
345.4327

> <EXACT_MASS>
345.194008357

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.01689308141441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-amino-3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
3.152797107267953

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.87103893936423

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.321722330930493

> <JCHEM_PKA_STRONGEST_BASIC>
8.35404237558417

> <JCHEM_POLAR_SURFACE_AREA>
92.78000000000002

> <JCHEM_REFRACTIVITY>
94.37109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-amino-3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041446
     RDKit          3D
Rosmaricine
 52 55  0  0  0  0  0  0  0  0999 V2000
    5.2371    0.2292   -0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100    0.2509    0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2198   -0.3320    1.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0666    0.0009    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2338    1.0603   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    0.8777   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388   -0.3942    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489   -1.4459    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769   -2.6570    0.7652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135   -1.2091    0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014   -2.2475    0.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813   -0.5231   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987   -1.8837   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351   -1.8436   -0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7092   -0.5218   -0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301    0.3496    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    1.6109    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208   -0.3629    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446    0.5994    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605    1.7401   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    1.1066   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854   -0.1841   -1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.9799   -2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    2.0342   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311    2.8997   -1.4187 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -0.2090   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0597   -0.5552   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    1.1681   -1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6006    1.4328    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2519    0.1190    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378    0.0666    2.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.4146    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176    1.9935   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148   -3.4995    1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762   -3.1662    1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -2.5920   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698   -2.1919    0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -2.1217   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771   -2.6378   -0.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655    0.0477   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8158   -0.7320   -0.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489    1.2627    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    2.0330   -0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367    2.3290    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8843   -0.5610    2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977    0.1883    2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1833   -1.3744    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    0.8531    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014    2.6220   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012    2.6636    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9043    2.3704   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624    3.7308   -1.6510 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 20 24  1  0
 24 25  1  0
 10  4  1  0
 19 12  1  0
 24  6  1  0
 22 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.128  -2.862   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.696  -3.632   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.155  -2.751   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.155  -1.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.476  -0.219   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.366   1.210   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.155   2.091   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.155   3.521   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -5.558   1.321   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.237   2.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.128   3.632   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.558  -1.871   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.128  -0.990   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.339  -0.219   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.128  -1.100   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.806  -0.219   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.806   1.321   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.485   2.091   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.164   1.321   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.164  -0.219   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.485  -0.990   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.596  -2.531   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.916  -2.421   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.587  -1.210   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.577   0.330   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   20   24                                             
CONECT    5    4    6   13                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11   17                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    1    5   12   14                                             
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16   15   17   21                                                  
CONECT   17   10   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19    7   18   20                                                  
CONECT   20    4   19   21                                                  
CONECT   21   16   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24                                                            
CONECT   24    4   23   25                                                  
CONECT   25    6   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0041446
HETATM    1  C1  UNL     1       5.237   0.229  -0.919  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.510   0.251   0.442  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.220  -0.332   1.588  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.067   0.001   0.254  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.234   1.060  -0.140  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.875   0.878  -0.214  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.339  -0.394   0.095  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.149  -1.446   0.485  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.577  -2.657   0.765  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.513  -1.209   0.557  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.301  -2.248   0.944  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.081  -0.523  -0.213  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.699  -1.884  -0.072  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.035  -1.844  -0.789  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.709  -0.522  -0.785  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.330   0.350   0.388  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.162   1.611   0.265  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.721  -0.363   1.654  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.845   0.599   0.398  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.460   1.740  -0.517  1.00  0.00           C  
HETATM   21  O3  UNL     1      -1.649   1.107  -1.802  1.00  0.00           O  
HETATM   22  C19 UNL     1      -1.185  -0.184  -1.696  1.00  0.00           C  
HETATM   23  O4  UNL     1      -0.894  -0.980  -2.595  1.00  0.00           O  
HETATM   24  C20 UNL     1      -0.011   2.034  -0.412  1.00  0.00           C  
HETATM   25  N1  UNL     1       0.531   2.900  -1.419  1.00  0.00           N  
HETATM   26  H1  UNL     1       4.504  -0.209  -1.671  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.060  -0.555  -0.854  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.606   1.168  -1.288  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.601   1.433   0.651  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.252   0.119   1.625  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.738   0.067   2.525  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.298  -1.415   1.616  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.718   1.994  -0.376  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.015  -3.500   1.043  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.976  -3.166   1.164  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.086  -2.592  -0.700  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.870  -2.192   0.944  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.878  -2.122  -1.870  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.677  -2.638  -0.361  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.666   0.048  -1.721  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.816  -0.732  -0.643  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.249   1.263   0.261  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.995   2.033  -0.763  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.037   2.329   1.069  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.884  -0.561   2.349  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.498   0.188   2.238  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.183  -1.374   1.404  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.541   0.853   1.421  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.101   2.622  -0.388  1.00  0.00           H  
HETATM   50  H25 UNL     1       0.101   2.664   0.561  1.00  0.00           H  
HETATM   51  H26 UNL     1       0.904   2.370  -2.195  1.00  0.00           H  
HETATM   52  H27 UNL     1      -0.062   3.731  -1.651  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   29
CONECT    3   30   31   32
CONECT    4    5    5   10
CONECT    5    6   33
CONECT    6    7    7   24
CONECT    7    8   12
CONECT    8    9   10   10
CONECT    9   34
CONECT   10   11
CONECT   11   35
CONECT   12   13   19   22
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   40   41
CONECT   16   17   18   19
CONECT   17   42   43   44
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   24   49
CONECT   21   22
CONECT   22   23   23
CONECT   24   25   50
CONECT   25   51   52
END

HMDB0041446
     RDKit          3D
Rosmaricine
 52 55  0  0  0  0  0  0  0  0999 V2000
    5.2371    0.2292   -0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100    0.2509    0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2198   -0.3320    1.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0666    0.0009    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2338    1.0603   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    0.8777   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388   -0.3942    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489   -1.4459    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769   -2.6570    0.7652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135   -1.2091    0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014   -2.2475    0.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813   -0.5231   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987   -1.8837   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351   -1.8436   -0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7092   -0.5218   -0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301    0.3496    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    1.6109    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208   -0.3629    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446    0.5994    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605    1.7401   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    1.1066   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854   -0.1841   -1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.9799   -2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    2.0342   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311    2.8997   -1.4187 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -0.2090   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0597   -0.5552   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    1.1681   -1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6006    1.4328    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2519    0.1190    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378    0.0666    2.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.4146    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176    1.9935   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148   -3.4995    1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762   -3.1662    1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -2.5920   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698   -2.1919    0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782   -2.1217   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771   -2.6378   -0.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655    0.0477   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8158   -0.7320   -0.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489    1.2627    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    2.0330   -0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367    2.3290    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8843   -0.5610    2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977    0.1883    2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1833   -1.3744    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    0.8531    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014    2.6220   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012    2.6636    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9043    2.3704   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624    3.7308   -1.6510 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 20 24  1  0
 24 25  1  0
 10  4  1  0
 19 12  1  0
 24  6  1  0
 22 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rosmaricine	MeSH
Rosmaricine hydrochloride	MeSH

Chemical Formula

C₂₀H₂₇NO₄

Average Molecular Weight

345.4327

Monoisotopic Molecular Weight

345.194008357

IUPAC Name

8-amino-3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

Traditional Name

8-amino-3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

CAS Registry Number

3650-11-1

SMILES

CC(C)C1=C(O)C(O)=C2C(=C1)C(N)C1OC(=O)C22CCCC(C)(C)C12

InChI Identifier

InChI=1S/C20H27NO4/c1-9(2)10-8-11-12(15(23)14(10)22)20-7-5-6-19(3,4)17(20)16(13(11)21)25-18(20)24/h8-9,13,16-17,22-23H,5-7,21H2,1-4H3

InChI Key

NFXKGLBUURRKEA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Phenanthrene
Benzoxepine
Tetralin
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Amine
Organopnictogen compound
Primary amine
Carbonyl group
Organic nitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0041446)
Cell membrane (HMDB: HMDB0041446)

Cellular substructure

Extracellular (HMDB: HMDB0041446)
Membrane (HMDB: HMDB0041446)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041446)

Source

Endogenous

Endogenous (HMDB: HMDB0041446)

Plant

Plant (HMDB: HMDB0041446)

Animal

Animal (HMDB: HMDB0041446)

Exogenous

Food

Food (HMDB: HMDB0041446)

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0041446)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0041446)

Cellular process

Cell signaling (HMDB: HMDB0041446)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0041446)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0041446)

Nutrient

Nutrient (HMDB: HMDB0041446)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041446)

Emulsifier (HMDB: HMDB0041446)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	199 - 200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.51	ALOGPS
logP	3.15	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	8.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.37 m³·mol⁻¹	ChemAxon
Polarizability	37.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.989	31661259
DarkChem	[M-H]-	176.568	31661259
DeepCCS	[M-2H]-	220.771	30932474
DeepCCS	[M+Na]+	195.998	30932474
AllCCS	[M+H]+	182.3	32859911
AllCCS	[M+H-H2O]+	179.4	32859911
AllCCS	[M+NH4]+	184.9	32859911
AllCCS	[M+Na]+	185.6	32859911
AllCCS	[M-H]-	189.9	32859911
AllCCS	[M+Na-2H]-	190.1	32859911
AllCCS	[M+HCOO]-	190.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rosmaricine	CC(C)C1=C(O)C(O)=C2C(=C1)C(N)C1OC(=O)C22CCCC(C)(C)C12	3869.0	Standard polar	33892256
Rosmaricine	CC(C)C1=C(O)C(O)=C2C(=C1)C(N)C1OC(=O)C22CCCC(C)(C)C12	2954.4	Standard non polar	33892256
Rosmaricine	CC(C)C1=C(O)C(O)=C2C(=C1)C(N)C1OC(=O)C22CCCC(C)(C)C12	2945.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rosmaricine,1TMS,isomer #1	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N	2840.5	Semi standard non polar	33892256
Rosmaricine,1TMS,isomer #2	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N	2849.2	Semi standard non polar	33892256
Rosmaricine,1TMS,isomer #3	CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C	2881.8	Semi standard non polar	33892256
Rosmaricine,2TMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N	2836.1	Semi standard non polar	33892256
Rosmaricine,2TMS,isomer #2	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C	2860.6	Semi standard non polar	33892256
Rosmaricine,2TMS,isomer #3	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C	2858.9	Semi standard non polar	33892256
Rosmaricine,2TMS,isomer #4	CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C)[Si](C)(C)C	2859.0	Semi standard non polar	33892256
Rosmaricine,3TMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C	2859.6	Semi standard non polar	33892256
Rosmaricine,3TMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C	2938.7	Standard non polar	33892256
Rosmaricine,3TMS,isomer #2	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C)[Si](C)(C)C	2881.2	Semi standard non polar	33892256
Rosmaricine,3TMS,isomer #2	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C)[Si](C)(C)C	3011.0	Standard non polar	33892256
Rosmaricine,3TMS,isomer #3	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C)[Si](C)(C)C	2869.5	Semi standard non polar	33892256
Rosmaricine,3TMS,isomer #3	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C)[Si](C)(C)C	2979.0	Standard non polar	33892256
Rosmaricine,4TMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C)[Si](C)(C)C	2922.8	Semi standard non polar	33892256
Rosmaricine,4TMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C)[Si](C)(C)C	3063.7	Standard non polar	33892256
Rosmaricine,1TBDMS,isomer #1	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N	3111.6	Semi standard non polar	33892256
Rosmaricine,1TBDMS,isomer #2	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N	3123.8	Semi standard non polar	33892256
Rosmaricine,1TBDMS,isomer #3	CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C(C)(C)C	3117.9	Semi standard non polar	33892256
Rosmaricine,2TBDMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N	3308.8	Semi standard non polar	33892256
Rosmaricine,2TBDMS,isomer #2	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C(C)(C)C	3314.0	Semi standard non polar	33892256
Rosmaricine,2TBDMS,isomer #3	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C(C)(C)C	3296.0	Semi standard non polar	33892256
Rosmaricine,2TBDMS,isomer #4	CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3283.8	Semi standard non polar	33892256
Rosmaricine,3TBDMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C(C)(C)C	3448.7	Semi standard non polar	33892256
Rosmaricine,3TBDMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N[Si](C)(C)C(C)(C)C	3544.1	Standard non polar	33892256
Rosmaricine,3TBDMS,isomer #2	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3540.6	Semi standard non polar	33892256
Rosmaricine,3TBDMS,isomer #2	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3601.0	Standard non polar	33892256
Rosmaricine,3TBDMS,isomer #3	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3511.0	Semi standard non polar	33892256
Rosmaricine,3TBDMS,isomer #3	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3574.6	Standard non polar	33892256
Rosmaricine,4TBDMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3720.1	Semi standard non polar	33892256
Rosmaricine,4TBDMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C13CCCC(C)(C)C1C(OC3=O)C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3806.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmaricine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gei-5129000000-5a8be4035dec4a16738c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmaricine GC-MS (2 TMS) - 70eV, Positive	splash10-0089-2001900000-dbcbbe8b78e1db6f0948	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmaricine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 10V, Positive-QTOF	splash10-0002-0009000000-33b196583a5c22a0e199	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 20V, Positive-QTOF	splash10-0gba-1329000000-9c9e4b5bbcab7c58d62d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 40V, Positive-QTOF	splash10-0a4i-6592000000-1d1969940b142be01877	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 10V, Negative-QTOF	splash10-0006-0009000000-357a54e7a3424d01062f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 20V, Negative-QTOF	splash10-0006-0009000000-d6919b7cc887373cd7e3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 40V, Negative-QTOF	splash10-0kfw-0193000000-d92aeec7abf3a51d498d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 10V, Positive-QTOF	splash10-0002-0009000000-54f432e2fc68cf88491c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 20V, Positive-QTOF	splash10-0002-0009000000-9b9f0be09737a5a22177	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 40V, Positive-QTOF	splash10-00y0-0093000000-ed483b9d159ca1757acc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 10V, Negative-QTOF	splash10-0006-0009000000-b93210fa3a7d33f09930	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 20V, Negative-QTOF	splash10-0006-0019000000-227dc897fe7fff07a92c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmaricine 40V, Negative-QTOF	splash10-016r-1269000000-4fffe4ec391d9b8d8aff	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021397

KNApSAcK ID

Not Available

Chemspider ID

293130

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

330877

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Rosmaricine (HMDB0041446)

MOL for HMDB0041446 (Rosmaricine)

3D MOL for HMDB0041446 (Rosmaricine)

3D SDF for HMDB0041446 (Rosmaricine)

3D-SDF for HMDB0041446 (Rosmaricine)

PDB for HMDB0041446 (Rosmaricine)

3D PDB for HMDB0041446 (Rosmaricine)

SMILES for HMDB0041446 (Rosmaricine)

INCHI for HMDB0041446 (Rosmaricine)

Structure for HMDB0041446 (Rosmaricine)

3D Structure for HMDB0041446 (Rosmaricine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra