NP-MRD: Showing NP-Card for asterolaurin B (NP0034891)

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Record Information

Version

2.0

Created at

2021-06-20 18:29:25 UTC

Updated at

2021-06-30 00:05:34 UTC

NP-MRD ID

NP0034891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

asterolaurin B

Provided By

JEOL Database JEOL Logo

Description

CHEMBL1088450 belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. asterolaurin B is found in Asterospicularia laurae. asterolaurin B was first documented in 2009 (Lin, Y. -C., et al.). Based on a literature review very few articles have been published on CHEMBL1088450.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


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  Mrv1652306202120293D          

 71 72  0  0  0  0            999 V2000
    3.3392   -1.9304   -2.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -2.8284   -1.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -4.1186   -1.3101 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7047   -4.0906   -0.2592 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9620   -3.7930   -0.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -3.2116    0.9998 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5034   -3.5568    1.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264   -1.7012    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -1.0825    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490   -0.8915    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -1.2647    1.1077 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1887   -1.3182   -0.2143 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3114   -1.0727    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158    0.1879    0.7933 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0823    1.2771    0.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435    2.2052    1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    3.2617    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821    2.1900    2.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325    0.6104    0.7714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7070    1.0770   -0.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944    0.6825   -1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0779    1.2560   -2.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8176   -0.3157   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562    1.7353    1.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    1.4260    2.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603    2.6688    3.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4851    0.2967    3.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -1.9411   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -3.0155   -1.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148   -2.9634   -1.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5484   -4.2492   -2.5506 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0922   -4.3800   -3.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811   -5.7627   -4.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4643   -3.5151   -4.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -2.6831   -0.9377 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8183   -1.0180   -2.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3119   -2.0904   -2.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -4.8753   -0.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9887   -4.4990   -2.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267   -5.1258    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6051   -3.7706   -0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5387   -3.5276    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -3.0032    2.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6248   -1.4046    1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8440    0.0121    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2201   -1.3490   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983    0.1765    0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -0.5050    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9077   -2.2050    1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5238   -0.5038   -0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344    0.0142    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454    4.0248    1.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    3.7382   -0.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1847    2.8173   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8400   -0.2298    1.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658    1.8331   -1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119    0.4557   -3.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3140    1.9734   -2.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0420    1.7751   -2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -0.6489    0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8196    0.1244   -0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8007   -1.2006   -1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690    3.3924    3.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222    2.4197    4.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403    3.0942    3.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.8999   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2901   -2.1695   -2.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4603   -5.9349   -4.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209   -6.4985   -3.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -5.8659   -5.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3738   -3.4630   -0.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  0  0  0  0
  4  3  1  0  0  0  0
  2  1  2  3  0  0  0
  3  2  1  0  0  0  0
 21 23  1  0  0  0  0
  2 35  1  0  0  0  0
 14 15  1  0  0  0  0
 35 12  1  0  0  0  0
 30 31  1  0  0  0  0
 12 11  1  0  0  0  0
  8  9  1  0  0  0  0
 11 10  1  0  0  0  0
 35 71  1  1  0  0  0
 10  8  2  0  0  0  0
 19 24  1  0  0  0  0
 28 13  2  0  0  0  0
  4  5  1  0  0  0  0
  8  6  1  0  0  0  0
 12 50  1  6  0  0  0
  6  4  1  0  0  0  0
 15 16  1  0  0  0  0
 29 30  1  0  0  0  0
 16 18  2  0  0  0  0
 13 14  1  0  0  0  0
 16 17  1  0  0  0  0
 30 35  1  0  0  0  0
 24 25  1  0  0  0  0
 14 19  1  0  0  0  0
 31 32  1  0  0  0  0
 12 13  1  0  0  0  0
 32 33  1  0  0  0  0
 19 20  1  0  0  0  0
 32 34  2  0  0  0  0
 25 26  1  0  0  0  0
 20 21  2  3  0  0  0
 25 27  2  0  0  0  0
 28 29  1  0  0  0  0
  6  7  1  0  0  0  0
 28 66  1  0  0  0  0
 30 67  1  6  0  0  0
  4 40  1  1  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
 11 48  1  0  0  0  0
 11 49  1  0  0  0  0
 10 47  1  0  0  0  0
  6 42  1  1  0  0  0
 14 51  1  1  0  0  0
 19 55  1  1  0  0  0
 20 56  1  0  0  0  0
 22 57  1  0  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
 23 60  1  0  0  0  0
 23 61  1  0  0  0  0
 23 62  1  0  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
  9 46  1  0  0  0  0
  5 41  1  0  0  0  0
 17 52  1  0  0  0  0
 17 53  1  0  0  0  0
 17 54  1  0  0  0  0
 33 68  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
 26 63  1  0  0  0  0
 26 64  1  0  0  0  0
 26 65  1  0  0  0  0
  7 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034891

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])\C(=C([H])/C([H])([H])[C@]2([H])C(=C([H])O[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2([H])C(=C([H])[H])C([H])([H])[C@@]1([H])O[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O9/c1-13(2)10-22(33-16(5)27)25(34-17(6)28)20-12-32-26(35-18(7)29)23-15(4)11-21(30)24(31)14(3)8-9-19(20)23/h8,10,12,19,21-26,30-31H,4,9,11H2,1-3,5-7H3/b14-8-/t19-,21-,22+,23+,24+,25-,26-/m1/s1

> <INCHI_KEY>
VFJIIFXMPRKDFM-SQZAKAIFSA-N

> <FORMULA>
C26H36O9

> <MOLECULAR_WEIGHT>
492.565

> <EXACT_MASS>
492.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.1187446096546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S)-1-[(1R,4aS,8S,9R,11aR)-1-(acetyloxy)-8,9-dihydroxy-7-methyl-11-methylidene-1H,4aH,5H,8H,9H,10H,11H,11aH-cyclonona[c]pyran-4-yl]-1-(acetyloxy)-4-methylpent-3-en-2-yl acetate

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.5111720720000015

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.042785762571825

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.493504448926899

> <JCHEM_PKA_STRONGEST_BASIC>
-3.203597867466363

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
127.41949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S)-1-[(1R,4aS,8S,9R,11aR)-1-(acetyloxy)-8,9-dihydroxy-7-methyl-11-methylidene-1H,4aH,5H,8H,9H,10H,11aH-cyclonona[c]pyran-4-yl]-1-(acetyloxy)-4-methylpent-3-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 72  0  0  0  0  0  0  0  0999 V2000
    3.3392   -1.9304   -2.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -2.8284   -1.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -4.1186   -1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7047   -4.0906   -0.2592 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9620   -3.7930   -0.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -3.2116    0.9998 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5034   -3.5568    1.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264   -1.7012    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -1.0825    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490   -0.8915    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -1.2647    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887   -1.3182   -0.2143 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3114   -1.0727    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158    0.1879    0.7933 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0823    1.2771    0.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435    2.2052    1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    3.2617    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821    2.1900    2.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325    0.6104    0.7714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7070    1.0770   -0.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944    0.6825   -1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0779    1.2560   -2.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8176   -0.3157   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562    1.7353    1.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    1.4260    2.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603    2.6688    3.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4851    0.2967    3.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -1.9411   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -3.0155   -1.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148   -2.9634   -1.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5484   -4.2492   -2.5506 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0922   -4.3800   -3.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811   -5.7627   -4.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4643   -3.5151   -4.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -2.6831   -0.9377 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8183   -1.0180   -2.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3119   -2.0904   -2.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -4.8753   -0.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9887   -4.4990   -2.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267   -5.1258    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6051   -3.7706   -0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5387   -3.5276    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -3.0032    2.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6248   -1.4046    1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8440    0.0121    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2201   -1.3490   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983    0.1765    0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -0.5050    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9077   -2.2050    1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5238   -0.5038   -0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344    0.0142    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454    4.0248    1.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    3.7382   -0.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1847    2.8173   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8400   -0.2298    1.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658    1.8331   -1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119    0.4557   -3.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3140    1.9734   -2.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0420    1.7751   -2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -0.6489    0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8196    0.1244   -0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8007   -1.2006   -1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690    3.3924    3.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222    2.4197    4.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403    3.0942    3.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.8999   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2901   -2.1695   -2.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4603   -5.9349   -4.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209   -6.4985   -3.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -5.8659   -5.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3738   -3.4630   -0.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  0
  4  3  1  0
  2  1  2  3
  3  2  1  0
 21 23  1  0
  2 35  1  0
 14 15  1  0
 35 12  1  0
 30 31  1  0
 12 11  1  0
  8  9  1  0
 11 10  1  0
 35 71  1  1
 10  8  2  0
 19 24  1  0
 28 13  2  0
  4  5  1  0
  8  6  1  0
 12 50  1  6
  6  4  1  0
 15 16  1  0
 29 30  1  0
 16 18  2  0
 13 14  1  0
 16 17  1  0
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 24 25  1  0
 14 19  1  0
 31 32  1  0
 12 13  1  0
 32 33  1  0
 19 20  1  0
 32 34  2  0
 25 26  1  0
 20 21  2  3
 25 27  2  0
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  6  7  1  0
 28 66  1  0
 30 67  1  6
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 11 48  1  0
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 33 68  1  0
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 33 70  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
  7 43  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  C   UNK     0       3.339  -1.930  -2.461  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.831  -2.828  -1.599  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.579  -4.119  -1.310  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.705  -4.091  -0.259  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.962  -3.793  -0.887  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.480  -3.212   1.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.503  -3.557   1.949  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.526  -1.701   0.820  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.876  -1.083   0.530  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.449  -0.892   0.882  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.009  -1.265   1.108  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.189  -1.318  -0.214  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.311  -1.073   0.013  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.716   0.188   0.793  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.082   1.277   0.253  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.544   2.205   1.130  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.309   3.262   0.394  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.382   2.190   2.341  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.232   0.610   0.771  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.707   1.077  -0.591  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.794   0.683  -1.285  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.078   1.256  -2.650  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.818  -0.316  -0.817  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.456   1.735   1.650  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.547   1.426   2.972  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.760   2.669   3.780  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.485   0.297   3.438  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.212  -1.941  -0.477  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.951  -3.015  -1.277  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.315  -2.963  -1.948  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.548  -4.249  -2.551  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.092  -4.380  -3.821  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.381  -5.763  -4.321  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.464  -3.515  -4.482  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.450  -2.683  -0.938  0.00  0.00           C+0
HETATM   36  H   UNK     0       2.818  -1.018  -2.731  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.312  -2.090  -2.922  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.846  -4.875  -0.998  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.989  -4.499  -2.256  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.827  -5.126   0.088  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.605  -3.771  -0.152  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.539  -3.528   1.458  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.341  -3.003   2.734  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.625  -1.405   1.259  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.844   0.012   0.576  0.00  0.00           H+0
HETATM   46  H   UNK     0       6.220  -1.349  -0.473  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.598   0.177   0.719  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.621  -0.505   1.792  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.908  -2.205   1.659  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.524  -0.504  -0.871  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.434   0.014   1.838  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.645   4.025   1.102  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.663   3.738  -0.348  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.185   2.817  -0.085  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.840  -0.230   1.120  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.066   1.833  -1.043  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.112   0.456  -3.396  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.314   1.973  -2.968  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.042   1.775  -2.651  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.665  -0.649   0.211  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.820   0.124  -0.863  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.801  -1.201  -1.462  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.969   3.392   3.569  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.722   2.420   4.844  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.740   3.094   3.551  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.279  -1.900  -0.302  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.290  -2.170  -2.708  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.460  -5.935  -4.331  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.121  -6.498  -3.688  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.002  -5.866  -5.342  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.374  -3.463  -0.165  0.00  0.00           H+0
CONECT    1    2   36   37                                                  
CONECT    2    1    3   35                                                  
CONECT    3    4    2   38   39                                             
CONECT    4    3    5    6   40                                             
CONECT    5    4   41                                                       
CONECT    6    8    4    7   42                                             
CONECT    7    6   43                                                       
CONECT    8    9   10    6                                                  
CONECT    9    8   44   45   46                                             
CONECT   10   11    8   47                                                  
CONECT   11   12   10   48   49                                             
CONECT   12   35   11   50   13                                             
CONECT   13   28   14   12                                                  
CONECT   14   15   13   19   51                                             
CONECT   15   14   16                                                       
CONECT   16   15   18   17                                                  
CONECT   17   16   52   53   54                                             
CONECT   18   16                                                            
CONECT   19   24   14   20   55                                             
CONECT   20   19   21   56                                                  
CONECT   21   22   23   20                                                  
CONECT   22   21   57   58   59                                             
CONECT   23   21   60   61   62                                             
CONECT   24   19   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   63   64   65                                             
CONECT   27   25                                                            
CONECT   28   13   29   66                                                  
CONECT   29   30   28                                                       
CONECT   30   31   29   35   67                                             
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   68   69   70                                             
CONECT   34   32                                                            
CONECT   35    2   12   71   30                                             
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   14                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   17                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   22                                                            
CONECT   60   23                                                            
CONECT   61   23                                                            
CONECT   62   23                                                            
CONECT   63   26                                                            
CONECT   64   26                                                            
CONECT   65   26                                                            
CONECT   66   28                                                            
CONECT   67   30                                                            
CONECT   68   33                                                            
CONECT   69   33                                                            
CONECT   70   33                                                            
CONECT   71   35                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  144    0
END

RDKit          3D

71 72  0  0  0  0  0  0  0  0999 V2000
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    2.8306   -2.8284   -1.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5034   -3.5568    1.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8757   -1.0825    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490   -0.8915    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -1.2647    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887   -1.3182   -0.2143 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3114   -1.0727    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158    0.1879    0.7933 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0823    1.2771    0.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3811   -5.7627   -4.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4643   -3.5151   -4.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8267   -5.1258    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6248   -1.4046    1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8440    0.0121    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2201   -1.3490   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6208   -0.5050    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9077   -2.2050    1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
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 21 22  1  0
  4  3  1  0
  2  1  2  3
  3  2  1  0
 21 23  1  0
  2 35  1  0
 14 15  1  0
 35 12  1  0
 30 31  1  0
 12 11  1  0
  8  9  1  0
 11 10  1  0
 35 71  1  1
 10  8  2  0
 19 24  1  0
 28 13  2  0
  4  5  1  0
  8  6  1  0
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M  END

View in JSmol

Synonyms

Value	Source
(1R,2S)-1-[(1R,4AS,8S,9R,11ar)-1-(acetyloxy)-8,9-dihydroxy-7-methyl-11-methylidene-1H,4ah,5H,8H,9H,10H,11H,11ah-cyclonona[c]pyran-4-yl]-1-(acetyloxy)-4-methylpent-3-en-2-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₆O₉

Average Mass

492.5650 Da

Monoisotopic Mass

492.23593 Da

IUPAC Name

(1R,2S)-1-[(1R,4aS,8S,9R,11aR)-1-(acetyloxy)-8,9-dihydroxy-7-methyl-11-methylidene-1H,4aH,5H,8H,9H,10H,11H,11aH-cyclonona[c]pyran-4-yl]-1-(acetyloxy)-4-methylpent-3-en-2-yl acetate

Traditional Name

(1R,2S)-1-[(1R,4aS,8S,9R,11aR)-1-(acetyloxy)-8,9-dihydroxy-7-methyl-11-methylidene-1H,4aH,5H,8H,9H,10H,11aH-cyclonona[c]pyran-4-yl]-1-(acetyloxy)-4-methylpent-3-en-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])\C(=C([H])/C([H])([H])[C@]2([H])C(=C([H])O[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2([H])C(=C([H])[H])C([H])([H])[C@@]1([H])O[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H36O9/c1-13(2)10-22(33-16(5)27)25(34-17(6)28)20-12-32-26(35-18(7)29)23-15(4)11-21(30)24(31)14(3)8-9-19(20)23/h8,10,12,19,21-26,30-31H,4,9,11H2,1-3,5-7H3/b14-8-/t19-,21-,22+,23+,24+,25-,26-/m1/s1

InChI Key

VFJIIFXMPRKDFM-SQZAKAIFSA-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
Asterospicularia laurae	JEOL database	Lin, Y. -C., et al, J. Nat. Prod. 72, 1911 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Tricarboxylic acid or derivatives
1,2-diol
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.71	ALOGPS
logP	1.51	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.49	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.42 m³·mol⁻¹	ChemAxon
Polarizability	52.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

24677303

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46186997

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin, Y. -C., et al. (2009). Lin, Y. -C., et al, J. Nat. Prod. 72, 1911 (2009). J. Nat. Prod..

Showing NP-Card for asterolaurin B (NP0034891)

MOL for NP0034891 (asterolaurin B)

3D MOL for NP0034891 (asterolaurin B)

3D SDF for NP0034891 (asterolaurin B)

3D-SDF for NP0034891 (asterolaurin B)

PDB for NP0034891 (asterolaurin B)

3D PDB for NP0034891 (asterolaurin B)

SMILES for NP0034891 (asterolaurin B)

INCHI for NP0034891 (asterolaurin B)

Structure for NP0034891 (asterolaurin B)

3D Structure for NP0034891 (asterolaurin B)