NP-MRD: Showing NP-Card for salvileucalin B (NP0038616)

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Record Information

Version

2.0

Created at

2021-06-20 21:15:35 UTC

Updated at

2021-06-30 00:11:30 UTC

NP-MRD ID

NP0038616

Secondary Accession Numbers

None

Natural Product Identification

Common Name

salvileucalin B

Provided By

JEOL Database JEOL Logo

Description

Salvileucalin B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. salvileucalin B is found in Salvia leucantha Cav. salvileucalin B was first documented in 2008 (PMID: 18788744). Based on a literature review a small amount of articles have been published on salvileucalin B (PMID: 20088588) (PMID: 20180530) (PMID: 21174417) (PMID: 21770370).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123153D          

 39 45  0  0  0  0            999 V2000
   -5.5647   -2.4003    0.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663   -1.7692    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828   -1.1766    1.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.4854    1.5699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4173   -0.7061    0.2207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4096   -1.4881   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874   -1.8441   -1.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -1.3540   -2.3333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7658    0.1900   -2.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6173    0.2976   -0.5990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1279    1.5654   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    1.6225    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.3947    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074   -0.8062    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -1.8751    1.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6958   -2.7293    0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701   -2.3563    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964   -3.4811   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715   -4.5250   -0.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -4.0704    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -1.1540    2.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    0.1862    2.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385    1.0612    3.0141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -0.9956   -0.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7191   -1.8472   -1.3709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1923    0.5693    1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932   -0.9198    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -2.4238   -2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -1.6590   -3.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    0.5994   -2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    0.7128   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    2.4883   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    2.5609    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -2.4948    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476   -1.3860   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1262   -3.6937   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823   -4.8061    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645   -1.6339   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002   -2.9179   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0  0  0  0
 17 16  1  0  0  0  0
 15 16  1  0  0  0  0
 24 14  1  0  0  0  0
 22 23  2  0  0  0  0
 10 24  1  0  0  0  0
 13 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 15  1  0  0  0  0
 15 14  1  0  0  0  0
 16 20  2  0  0  0  0
 24 25  1  6  0  0  0
  8 25  1  0  0  0  0
 14 13  2  0  0  0  0
  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
  5  6  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 20 19  1  0  0  0  0
  6  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
 19 18  1  0  0  0  0
  2  1  2  0  0  0  0
 10  5  1  0  0  0  0
 24  5  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 11 32  1  0  0  0  0
 12 33  1  0  0  0  0
 15 34  1  1  0  0  0
 20 37  1  0  0  0  0
 18 36  1  0  0  0  0
 17 35  1  0  0  0  0
 25 38  1  0  0  0  0
 25 39  1  0  0  0  0
  8 29  1  6  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  7 28  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
M  END

     RDKit          3D

 39 45  0  0  0  0  0  0  0  0999 V2000
   -5.5647   -2.4003    0.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663   -1.7692    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828   -1.1766    1.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.4854    1.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -0.7061    0.2207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4096   -1.4881   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874   -1.8441   -1.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -1.3540   -2.3333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7658    0.1900   -2.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6173    0.2976   -0.5990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1279    1.5654   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    1.6225    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.3947    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074   -0.8062    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -1.8751    1.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6958   -2.7293    0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701   -2.3563    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964   -3.4811   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715   -4.5250   -0.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -4.0704    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -1.1540    2.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    0.1862    2.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385    1.0612    3.0141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -0.9956   -0.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7191   -1.8472   -1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1923    0.5693    1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932   -0.9198    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -2.4238   -2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -1.6590   -3.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    0.5994   -2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    0.7128   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    2.4883   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    2.5609    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -2.4948    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476   -1.3860   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1262   -3.6937   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823   -4.8061    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645   -1.6339   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002   -2.9179   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0
 17 16  1  0
 15 16  1  0
 24 14  1  0
 22 23  2  0
 10 24  1  0
 13 22  1  0
 22 21  1  0
 21 15  1  0
 15 14  1  0
 16 20  2  0
 24 25  1  6
  8 25  1  0
 14 13  2  0
  8  7  1  0
  7  6  2  0
  5  6  1  0
 10 11  1  1
 11 12  2  0
 12 13  1  0
 20 19  1  0
  6  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
 19 18  1  0
  2  1  2  0
 10  5  1  0
 24  5  1  0
  8  9  1  0
 10  9  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  1
 20 37  1  0
 18 36  1  0
 17 35  1  0
 25 38  1  0
 25 39  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
  7 28  1  0
  4 26  1  0
  4 27  1  0
M  END


  Mrv1652306202123153D          

 39 45  0  0  0  0            999 V2000
   -5.5647   -2.4003    0.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663   -1.7692    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828   -1.1766    1.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.4854    1.5699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4173   -0.7061    0.2207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4096   -1.4881   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874   -1.8441   -1.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -1.3540   -2.3333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7658    0.1900   -2.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6173    0.2976   -0.5990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1279    1.5654   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    1.6225    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.3947    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074   -0.8062    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -1.8751    1.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6958   -2.7293    0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701   -2.3563    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964   -3.4811   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715   -4.5250   -0.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -4.0704    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -1.1540    2.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    0.1862    2.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385    1.0612    3.0141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -0.9956   -0.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7191   -1.8472   -1.3709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1923    0.5693    1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932   -0.9198    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -2.4238   -2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -1.6590   -3.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    0.5994   -2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    0.7128   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    2.4883   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    2.5609    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -2.4948    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476   -1.3860   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1262   -3.6937   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823   -4.8061    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645   -1.6339   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002   -2.9179   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0  0  0  0
 17 16  1  0  0  0  0
 15 16  1  0  0  0  0
 24 14  1  0  0  0  0
 22 23  2  0  0  0  0
 10 24  1  0  0  0  0
 13 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 15  1  0  0  0  0
 15 14  1  0  0  0  0
 16 20  2  0  0  0  0
 24 25  1  6  0  0  0
  8 25  1  0  0  0  0
 14 13  2  0  0  0  0
  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
  5  6  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 20 19  1  0  0  0  0
  6  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
 19 18  1  0  0  0  0
  2  1  2  0  0  0  0
 10  5  1  0  0  0  0
 24  5  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 11 32  1  0  0  0  0
 12 33  1  0  0  0  0
 15 34  1  1  0  0  0
 20 37  1  0  0  0  0
 18 36  1  0  0  0  0
 17 35  1  0  0  0  0
 25 38  1  0  0  0  0
 25 39  1  0  0  0  0
  8 29  1  6  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  7 28  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038616

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C(=C([H])O1)[C@@]1([H])OC(=O)C2=C1[C@@]13C([H])([H])[C@@]4([H])C([H])=C5C(=O)OC([H])([H])[C@@]15[C@]3(C([H])=C2[H])C4([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O5/c21-16-12-1-3-18-6-10-5-13-17(22)24-9-20(13,18)19(18,7-10)14(12)15(25-16)11-2-4-23-8-11/h1-5,8,10,15H,6-7,9H2/t10-,15+,18+,19+,20+/m0/s1

> <INCHI_KEY>
ZWSRRRRYHMMHQC-MDOCMBDYSA-N

> <FORMULA>
C20H14O5

> <MOLECULAR_WEIGHT>
334.327

> <EXACT_MASS>
334.084123551

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.57837159814683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,9S,11S,17S)-3-(furan-3-yl)-4,15-dioxahexacyclo[9.6.1.0^{1,9}.0^{2,6}.0^{9,17}.0^{13,17}]octadeca-2(6),7,12-triene-5,14-dione

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
1.5107083806666668

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.11944397849613

> <JCHEM_PKA_STRONGEST_BASIC>
-2.890336054838408

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
86.81049999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,9S,11S,17S)-3-(furan-3-yl)-4,15-dioxahexacyclo[9.6.1.0^{1,9}.0^{2,6}.0^{9,17}.0^{13,17}]octadeca-2(6),7,12-triene-5,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 45  0  0  0  0  0  0  0  0999 V2000
   -5.5647   -2.4003    0.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663   -1.7692    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828   -1.1766    1.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.4854    1.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -0.7061    0.2207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4096   -1.4881   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874   -1.8441   -1.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -1.3540   -2.3333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7658    0.1900   -2.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6173    0.2976   -0.5990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1279    1.5654   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    1.6225    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.3947    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074   -0.8062    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -1.8751    1.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6958   -2.7293    0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701   -2.3563    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964   -3.4811   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715   -4.5250   -0.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -4.0704    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -1.1540    2.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    0.1862    2.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385    1.0612    3.0141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -0.9956   -0.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7191   -1.8472   -1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1923    0.5693    1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932   -0.9198    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -2.4238   -2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -1.6590   -3.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    0.5994   -2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    0.7128   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    2.4883   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    2.5609    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -2.4948    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476   -1.3860   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1262   -3.6937   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823   -4.8061    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645   -1.6339   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002   -2.9179   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0
 17 16  1  0
 15 16  1  0
 24 14  1  0
 22 23  2  0
 10 24  1  0
 13 22  1  0
 22 21  1  0
 21 15  1  0
 15 14  1  0
 16 20  2  0
 24 25  1  6
  8 25  1  0
 14 13  2  0
  8  7  1  0
  7  6  2  0
  5  6  1  0
 10 11  1  1
 11 12  2  0
 12 13  1  0
 20 19  1  0
  6  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
 19 18  1  0
  2  1  2  0
 10  5  1  0
 24  5  1  0
  8  9  1  0
 10  9  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  1
 20 37  1  0
 18 36  1  0
 17 35  1  0
 25 38  1  0
 25 39  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
  7 28  1  0
  4 26  1  0
  4 27  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -5.565  -2.400   0.076  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.566  -1.769   0.359  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.283  -1.177   1.565  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.998  -0.485   1.570  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.417  -0.706   0.221  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.410  -1.488  -0.508  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.187  -1.844  -1.784  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.847  -1.354  -2.333  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.766   0.190  -2.119  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.617   0.298  -0.599  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.128   1.565  -0.004  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.129   1.623   0.899  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.475   0.395   1.337  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.107  -0.806   0.882  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.846  -1.875   1.602  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.696  -2.729   0.722  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.870  -2.356   0.001  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.296  -3.481  -0.664  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.471  -4.525  -0.403  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.514  -4.070   0.444  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.657  -1.154   2.548  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.476   0.186   2.382  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.038   1.061   3.014  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.957  -0.996  -0.119  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.719  -1.847  -1.371  0.00  0.00           C+0
HETATM   26  H   UNK     0      -3.192   0.569   1.785  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.393  -0.920   2.371  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.885  -2.424  -2.377  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.699  -1.659  -3.372  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.882   0.599  -2.621  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.659   0.713  -2.477  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.602   2.488  -0.331  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.219   2.561   1.319  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.148  -2.495   2.177  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.348  -1.386  -0.025  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.126  -3.694  -1.324  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.782  -4.806   0.750  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.265  -1.634  -1.805  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.800  -2.918  -1.157  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    6    3    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26   27                                             
CONECT    5    6    4   10   24                                             
CONECT    6    7    5    2                                                  
CONECT    7    8    6   28                                                  
CONECT    8   25    7    9   29                                             
CONECT    9    8   10   30   31                                             
CONECT   10   24   11    5    9                                             
CONECT   11   10   12   32                                                  
CONECT   12   11   13   33                                                  
CONECT   13   22   14   12                                                  
CONECT   14   24   15   13                                                  
CONECT   15   16   21   14   34                                             
CONECT   16   17   15   20                                                  
CONECT   17   18   16   35                                                  
CONECT   18   17   19   36                                                  
CONECT   19   20   18                                                       
CONECT   20   16   19   37                                                  
CONECT   21   22   15                                                       
CONECT   22   23   13   21                                                  
CONECT   23   22                                                            
CONECT   24   14   10   25    5                                             
CONECT   25   24    8   38   39                                             
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   15                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
CONECT   38   25                                                            
CONECT   39   25                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

RDKit          3D

39 45  0  0  0  0  0  0  0  0999 V2000
   -5.5647   -2.4003    0.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663   -1.7692    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828   -1.1766    1.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.4854    1.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -0.7061    0.2207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4096   -1.4881   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874   -1.8441   -1.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -1.3540   -2.3333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7658    0.1900   -2.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6173    0.2976   -0.5990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1279    1.5654   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    1.6225    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.3947    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074   -0.8062    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -1.8751    1.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6958   -2.7293    0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701   -2.3563    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964   -3.4811   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715   -4.5250   -0.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -4.0704    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -1.1540    2.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    0.1862    2.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385    1.0612    3.0141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -0.9956   -0.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7191   -1.8472   -1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1923    0.5693    1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932   -0.9198    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -2.4238   -2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -1.6590   -3.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    0.5994   -2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    0.7128   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    2.4883   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    2.5609    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -2.4948    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476   -1.3860   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1262   -3.6937   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823   -4.8061    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645   -1.6339   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002   -2.9179   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0
 17 16  1  0
 15 16  1  0
 24 14  1  0
 22 23  2  0
 10 24  1  0
 13 22  1  0
 22 21  1  0
 21 15  1  0
 15 14  1  0
 16 20  2  0
 24 25  1  6
  8 25  1  0
 14 13  2  0
  8  7  1  0
  7  6  2  0
  5  6  1  0
 10 11  1  1
 11 12  2  0
 12 13  1  0
 20 19  1  0
  6  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
 19 18  1  0
  2  1  2  0
 10  5  1  0
 24  5  1  0
  8  9  1  0
 10  9  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  1
 20 37  1  0
 18 36  1  0
 17 35  1  0
 25 38  1  0
 25 39  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
  7 28  1  0
  4 26  1  0
  4 27  1  0
M  END

View in JSmol

Synonyms

Value	Source
(+)-Salvileucalin b	ChEBI

Chemical Formula

C₂₀H₁₄O₅

Average Mass

334.3270 Da

Monoisotopic Mass

334.08412 Da

IUPAC Name

(1R,3S,9S,11S,17S)-3-(furan-3-yl)-4,15-dioxahexacyclo[9.6.1.0^{1,9}.0^{2,6}.0^{9,17}.0^{13,17}]octadeca-2(6),7,12-triene-5,14-dione

Traditional Name

(1R,3S,9S,11S,17S)-3-(furan-3-yl)-4,15-dioxahexacyclo[9.6.1.0^{1,9}.0^{2,6}.0^{9,17}.0^{13,17}]octadeca-2(6),7,12-triene-5,14-dione

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C(=C([H])O1)[C@@]1([H])OC(=O)C2=C1[C@@]13C([H])([H])[C@@]4([H])C([H])=C5C(=O)OC([H])([H])[C@@]15[C@]3(C([H])=C2[H])C4([H])[H]

InChI Identifier

InChI=1S/C20H14O5/c21-16-12-1-3-18-6-10-5-13-17(22)24-9-20(13,18)19(18,7-10)14(12)15(25-16)11-2-4-23-8-11/h1-5,8,10,15H,6-7,9H2/t10-,15+,18+,19+,20+/m0/s1

InChI Key

ZWSRRRRYHMMHQC-MDOCMBDYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia leucantha	JEOL database	Aoyagi, Y., et al, Org. Lett. 10, 4429 (2008)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.11	ALOGPS
logP	1.51	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.12	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.81 m³·mol⁻¹	ChemAxon
Polarizability	32.58 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28466272

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

66154

Good Scents ID

Not Available

References

General References

Aoyagi Y, Yamazaki A, Nakatsugawa C, Fukaya H, Takeya K, Kawauchi S, Izumi H: Salvileucalin B, a novel diterpenoid with an unprecedented rearranged neoclerodane skeleton from Salvia leucantha Cav. Org Lett. 2008 Oct 16;10(20):4429-32. doi: 10.1021/ol801620u. Epub 2008 Sep 13. [PubMed:18788744 ]
Levin S, Nani RR, Reisman SE: Rapid assembly of the salvileucalin B norcaradiene core. Org Lett. 2010 Feb 19;12(4):780-3. doi: 10.1021/ol902848k. [PubMed:20088588 ]
Tantillo DJ: How an enzyme might accelerate an intramolecular Diels-Alder reaction: theozymes for the formation of salvileucalin B. Org Lett. 2010 Mar 19;12(6):1164-7. doi: 10.1021/ol9028435. [PubMed:20180530 ]
Levin S, Nani RR, Reisman SE: Enantioselective total synthesis of (+)-salvileucalin B. J Am Chem Soc. 2011 Feb 2;133(4):774-6. doi: 10.1021/ja110192b. [PubMed:21174417 ]
Tseng CC, Ding H, Li A, Guan Y, Chen DY: A modular synthesis of salvileucalin B structural domains. Org Lett. 2011 Aug 19;13(16):4410-3. doi: 10.1021/ol201748x. Epub 2011 Jul 19. [PubMed:21770370 ]
Aoyagi, Y., et al. (2008). Aoyagi, Y., et al, Org. Lett. 10, 4429 (2008). Org. Lett..

Showing NP-Card for salvileucalin B (NP0038616)

MOL for NP0038616 (salvileucalin B)

3D MOL for NP0038616 (salvileucalin B)

3D SDF for NP0038616 (salvileucalin B)

3D-SDF for NP0038616 (salvileucalin B)

PDB for NP0038616 (salvileucalin B)

3D PDB for NP0038616 (salvileucalin B)

SMILES for NP0038616 (salvileucalin B)

INCHI for NP0038616 (salvileucalin B)

Structure for NP0038616 (salvileucalin B)

3D Structure for NP0038616 (salvileucalin B)