NP-MRD: Showing NP-Card for Spiratine B (NP0067292)

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Record Information

Version

1.0

Created at

2022-04-28 11:51:19 UTC

Updated at

2022-04-28 11:51:19 UTC

NP-MRD ID

NP0067292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spiratine B

Description

Spiratie B belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. Spiratine B is found in Spiraea japonica and Spiraea japonica var.acuta. It was first documented in 2022 (PMID: 35487649). Based on a literature review a significant number of articles have been published on Spiratie B (PMID: 35487635) (PMID: 35487578) (PMID: 35487545) (PMID: 35487543).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213512D          

 30 34  0  0  1  0            999 V2000
    3.9284    0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2238    1.6301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9774    1.9659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7477    1.6705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8104    1.0738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2642    0.1063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5268    0.3398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9792    1.0296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6014    1.6670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4361    1.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6722    2.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945    3.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718    3.5302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7601    4.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581    2.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    2.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833    2.6322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034    3.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228    0.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4603    0.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    0.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939   -0.2958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9430   -0.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447    0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0345   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7881    0.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0835    0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5330    2.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2379    2.9563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  8 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  1  0  0  0
 22 23  1  0  0  0  0
  7 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  1  0  0  0
  3 30  1  6  0  0  0
M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
   -4.0183   -2.7385    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -1.9622    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566   -0.6343    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -0.3290   -0.0542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1542    0.0148   -1.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661   -1.0981   -1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231   -2.3444   -1.0002 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3161   -2.5573   -1.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033   -1.5483   -0.0804 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7473   -1.3538   -0.3383 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1118   -1.1241   -1.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468   -0.8490   -1.9847 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2349   -0.2162   -1.0958 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4565   -0.9272   -1.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7341   -0.0629    0.3101 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3114    1.1850    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -1.2343    1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219   -2.3189    1.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4757   -2.5931    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617   -0.1466    0.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4941    1.0207   -0.0880 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0439    2.2712    0.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2623    3.1416   -0.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381    4.4791   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297    2.7244   -2.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.8752    0.5658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6583    2.0141    0.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041    2.6783    1.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9362    3.9082    1.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7674    2.1855    2.7174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3100   -2.4311    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3550   -3.6868    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312    0.1348    0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4863   -0.6321    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.9611   -1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050    0.2802   -2.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1163   -0.7682   -1.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847   -1.3269   -2.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3491   -3.2101   -1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951   -2.4762   -2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -3.6111   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791   -2.0207    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4632   -1.1612   -2.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4698    0.8059   -1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2723   -1.8867   -1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2670    0.9579    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6548    1.6551    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509    1.9245    0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6551   -0.8799    2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2363   -1.6291    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843   -3.2544    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6836   -2.1331    2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -3.4103    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617   -2.9968   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0020   -0.3332    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    0.8728   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008    4.4557   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7519    4.9459    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    5.1366   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7122    0.6207    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0260    3.6356    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7917    4.4413    2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6695    4.5596    0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 25  2  0
 23 22  1  0
 22 21  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 26  4  1  0
  4  5  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 19  1  1
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  1
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
 15 20  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
 20 21  1  0
  9  4  1  0
 10 11  1  0
  3  4  1  0
 20 10  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 21 56  1  6
 26 60  1  1
 29 61  1  0
 29 62  1  0
 29 63  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  6
  8 40  1  0
  8 41  1  0
  9 42  1  1
 19 53  1  0
 19 54  1  0
 18 51  1  0
 18 52  1  0
 17 49  1  0
 17 50  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 13 44  1  6
 14 45  1  0
 11 43  1  0
 20 55  1  1
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
M  END


  Mrv1652304282213512D          

 30 34  0  0  1  0            999 V2000
    3.9284    0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2238    1.6301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9774    1.9659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7477    1.6705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8104    1.0738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2642    0.1063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5268    0.3398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9792    1.0296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6014    1.6670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4361    1.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6722    2.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945    3.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718    3.5302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7601    4.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581    2.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    2.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833    2.6322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034    3.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228    0.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4603    0.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    0.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939   -0.2958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9430   -0.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447    0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0345   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7881    0.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0835    0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5330    2.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2379    2.9563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  8 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  1  0  0  0
 22 23  1  0  0  0  0
  7 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  1  0  0  0
  3 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0067292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@]23CC[C@@H](C[C@H]2[C@@]24CCC[C@@](C)([C@@H](O)N=C2)[C@@H]14)C(=C)C3

> <INCHI_IDENTIFIER>
InChI=1S/C24H33NO5/c1-13-11-23-9-6-16(13)10-17(23)24-8-5-7-22(4,21(28)25-12-24)19(24)18(29-14(2)26)20(23)30-15(3)27/h12,16-21,28H,1,5-11H2,2-4H3/t16-,17+,18-,19+,20+,21+,22+,23+,24+/m0/s1

> <INCHI_KEY>
SKHHEQWFHJZHLK-AMJQQQQASA-N

> <FORMULA>
C24H33NO5

> <MOLECULAR_WEIGHT>
415.53

> <EXACT_MASS>
415.235873167

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.9121405253886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4S,7R,8S,9S,10S,11R,12R)-9-(acetyloxy)-12-hydroxy-11-methyl-5-methylidene-13-azapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadec-13-en-8-yl acetate

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.4136239380000015

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.314832497008624

> <JCHEM_PKA_STRONGEST_BASIC>
2.8963494041397255

> <JCHEM_POLAR_SURFACE_AREA>
85.19000000000001

> <JCHEM_REFRACTIVITY>
109.03829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,7R,8S,9S,10S,11R,12R)-9-(acetyloxy)-12-hydroxy-11-methyl-5-methylidene-13-azapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadec-13-en-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.333   1.605   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.884   3.043   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.291   3.670   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.729   3.118   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.979   2.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.960   0.198   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.583   0.634   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.561   1.922   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.723   3.112   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.281   3.407   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.721   5.003   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.016   6.473   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.481   6.590   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.886   7.744   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.708   4.613   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.351   5.564   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.955   4.913   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.486   7.098   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.776   1.621   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.726   0.468   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.134   0.223   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.909  -0.552   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.494  -0.586   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.563   0.892   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.308   2.603   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.398  -0.353   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.804   0.274   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.356   1.712   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.195   3.969   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.777   5.518   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5   28   29                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7   26                                             
CONECT    7    6    8   23                                                  
CONECT    8    7    9   19   25                                             
CONECT    9    8   10   15                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22    7                                                       
CONECT   24   22   25                                                       
CONECT   25   24    8                                                       
CONECT   26    6   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    4                                                       
CONECT   29    4                                                            
CONECT   30    3                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₃NO₅

Average Mass

415.5300 Da

Monoisotopic Mass

415.23587 Da

IUPAC Name

(1R,2S,4S,7R,8S,9S,10S,11R,12R)-9-(acetyloxy)-12-hydroxy-11-methyl-5-methylidene-13-azapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadec-13-en-8-yl acetate

Traditional Name

(1R,2S,4S,7R,8S,9S,10S,11R,12R)-9-(acetyloxy)-12-hydroxy-11-methyl-5-methylidene-13-azapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadec-13-en-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@]23CC[C@@H](C[C@H]2[C@@]24CCC[C@@](C)([C@@H](O)N=C2)[C@@H]14)C(=C)C3

InChI Identifier

InChI=1S/C24H33NO5/c1-13-11-23-9-6-16(13)10-17(23)24-8-5-7-22(4,21(28)25-12-24)19(24)18(29-14(2)26)20(23)30-15(3)27/h12,16-21,28H,1,5-11H2,2-4H3/t16-,17+,18-,19+,20+,21+,22+,23+,24+/m0/s1

InChI Key

SKHHEQWFHJZHLK-AMJQQQQASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Spiraea japonica	LOTUS Database	35616633
Spiraea japonica var.acuta	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Tetrahydropyridine
Dicarboxylic acid or derivatives
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Alkanolamine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Imine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
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	2.95	ALOGPS
logP	2.41	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.31	ChemAxon
pKa (Strongest Basic)	2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.04 m³·mol⁻¹	ChemAxon
Polarizability	44.91 Å³	ChemAxon
Number of Rings	5	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

10210046

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10645523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Teng Z, Zheng W, Jiang S, Hong SB, Zhu Z, Zang Y: Role of melatonin in promoting plant growth by regulating carbon assimilation and ATP accumulation. Plant Sci. 2022 Jun;319:111276. doi: 10.1016/j.plantsci.2022.111276. Epub 2022 Mar 30. [PubMed:35487649 ]
Nakabayashi K, Shimizu T, Takahashi K, Ando H: Emergent option in complicated acute type B aortic dissection. BMJ Case Rep. 2022 Apr 29;15(4). pii: 15/4/e249204. doi: 10.1136/bcr-2022-249204. [PubMed:35487635 ]
Tan HX, Wragg KM, Kelly HG, Esterbauer R, Dixon BJ, Lau JSY, Flanagan KL, van de Sandt CE, Kedzierska K, McMahon JH, Wheatley AK, Juno JA, Kent SJ: Cutting Edge: SARS-CoV-2 Infection Induces Robust Germinal Center Activity in the Human Tonsil. J Immunol. 2022 Apr 29. pii: jimmunol.2101199. doi: 10.4049/jimmunol.2101199. [PubMed:35487578 ]
Nyirahabihirwe F, Kamali I, Barnhart DA, Gakuru JP, Musafiri T, Rwamuhinda DD, Mutabazi P, Mukayirabuka S, Makuza JD, Kassim N, Mubiligi JM, Ndahimana JD, Kateera F: Implementation of Refugees' Inclusion in National Viral Hepatitis B and Hepatitis C Screening Campaign in Mahama Refugee Camp, Rwanda. Glob Health Sci Pract. 2022 Apr 29;10(2). pii: GHSP-D-21-00349. doi: 10.9745/GHSP-D-21-00349. Print 2022 Apr 28. [PubMed:35487545 ]
Iyengar K, Gupta M, Pal S, Kaur K, Singla N, Verma M, Dhiman A, Singla R, Rohilla M, Suri V, Aggarwal N, Singh T, Goel P, Goel NK, Pant R, Gaur KL, Gehlot H, Bhati I, Verma M, Agarwal S, Acharya R, Singh K, Chauhan M, Rastogi R, Bedi R, Pancholi P, Nayak B, Modi B, Nakum K, Trivedi A, Aggarwal S, Patel S: Baseline Assessment of Evidence-Based Intrapartum Care Practices in Medical Schools in 3 States in India: A Mixed-Methods Study. Glob Health Sci Pract. 2022 Apr 29;10(2). pii: GHSP-D-21-00590. doi: 10.9745/GHSP-D-21-00590. Print 2022 Apr 28. [PubMed:35487543 ]

Showing NP-Card for Spiratine B (NP0067292)

MOL for NP0067292 (Spiratine B)

3D MOL for NP0067292 (Spiratine B)

3D SDF for NP0067292 (Spiratine B)

3D-SDF for NP0067292 (Spiratine B)

PDB for NP0067292 (Spiratine B)

3D PDB for NP0067292 (Spiratine B)

SMILES for NP0067292 (Spiratine B)

INCHI for NP0067292 (Spiratine B)

Structure for NP0067292 (Spiratine B)

3D Structure for NP0067292 (Spiratine B)