Natural Product: NPC475307

Natural Product ID:  NPC475307
Common Name:   Lupulin A
IUPAC Name:   [(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2S,3aS,5S,6aR)-5-methoxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] (2R)-2-methylbutanoate
Synonyms:  
Molecular Formula:   C30H46O11
Standard InCHIKey:  UEZOFWAZJUOMCN-BVDQYQNCSA-N
Standard InCHI:  InChI=1S/C30H46O11/c1-8-15(2)26(34)41-25-20(33)12-21-28(6,22-10-19-11-24(35-7)40-27(19)39-22)16(3)9-23(38-18(5)32)29(21,13-36-17(4)31)30(25)14-37-30/h15-16,19-25,27,33H,8-14H2,1-7H3/t15-,16-,19+,20-,21-,22+,23+,24+,25+,27-,28+,29+,30-/m1/s1
Canonical SMILES:  CO[C@@H]1C[C@H]2[C@@H](O1)O[C@@H](C2)[C@@]1(C)[C@H](C)C[C@@H]([C@@]2([C@@H]1C[C@@H](O)[C@@H]([C@@]12CO1)OC(=O)[C@@H](CC)C)COC(=O)C)OC(=O)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO3534 Ajuga lupulina Species Lamiaceae Eukaryota PMID[8759163]
NPO18973 Ajuga pseudoiva Species Lamiaceae Eukaryota Leaves Tunisian PMID[10727804]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 1.5 mm 18625775
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa IZ = 3 mm 19075057
NPT19 Organism Escherichia coli Escherichia coli IZ = 3 mm 19075057

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC475307 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9535 High Similarity NPC470872
0.9302 High Similarity NPC474008
0.9195 High Similarity NPC110365
0.9195 High Similarity NPC45833
0.9195 High Similarity NPC213658
0.9195 High Similarity NPC62202
0.9186 High Similarity NPC235402
0.907 High Similarity NPC18953
0.8652 High Similarity NPC471410
0.8652 High Similarity NPC471411
0.8621 High Similarity NPC477447
0.8621 High Similarity NPC470155
0.8621 High Similarity NPC477446
0.8617 High Similarity NPC475785
0.8617 High Similarity NPC475765
0.8605 High Similarity NPC471217
0.8605 High Similarity NPC472951
0.8605 High Similarity NPC471216
0.8605 High Similarity NPC472943
0.8605 High Similarity NPC186588
0.8526 High Similarity NPC266417
0.8506 High Similarity NPC470154
0.8506 High Similarity NPC470156
0.8506 High Similarity NPC71541
0.8462 Intermediate Similarity NPC476435
0.8444 Intermediate Similarity NPC268633
0.8333 Intermediate Similarity NPC86217
0.8315 Intermediate Similarity NPC241959
0.8298 Intermediate Similarity NPC122083
0.8298 Intermediate Similarity NPC211845
0.8298 Intermediate Similarity NPC182740
0.8298 Intermediate Similarity NPC256104
0.8295 Intermediate Similarity NPC211049
0.828 Intermediate Similarity NPC470114
0.8261 Intermediate Similarity NPC221993
0.8261 Intermediate Similarity NPC476379
0.8247 Intermediate Similarity NPC292775
0.8242 Intermediate Similarity NPC107603
0.8235 Intermediate Similarity NPC305939
0.8229 Intermediate Similarity NPC252056
0.8229 Intermediate Similarity NPC238796
0.8229 Intermediate Similarity NPC203434
0.8229 Intermediate Similarity NPC237071
0.8211 Intermediate Similarity NPC151214
0.8211 Intermediate Similarity NPC191915
0.8202 Intermediate Similarity NPC216800
0.8191 Intermediate Similarity NPC475878
0.8182 Intermediate Similarity NPC186594
0.8163 Intermediate Similarity NPC470030
0.814 Intermediate Similarity NPC107963
0.8125 Intermediate Similarity NPC57964
0.8125 Intermediate Similarity NPC94582
0.8125 Intermediate Similarity NPC21897
0.8111 Intermediate Similarity NPC474253
0.8111 Intermediate Similarity NPC475820
0.8111 Intermediate Similarity NPC474284
0.8111 Intermediate Similarity NPC213737
0.8111 Intermediate Similarity NPC474346
0.81 Intermediate Similarity NPC139181
0.81 Intermediate Similarity NPC476837
0.81 Intermediate Similarity NPC97260
0.809 Intermediate Similarity NPC116320
0.809 Intermediate Similarity NPC119922
0.8081 Intermediate Similarity NPC108227
0.8081 Intermediate Similarity NPC475574
0.8081 Intermediate Similarity NPC476512
0.8081 Intermediate Similarity NPC472081
0.8065 Intermediate Similarity NPC471221
0.8061 Intermediate Similarity NPC472144
0.8043 Intermediate Similarity NPC235196
0.8043 Intermediate Similarity NPC477283
0.8043 Intermediate Similarity NPC155531
0.8043 Intermediate Similarity NPC215968
0.8043 Intermediate Similarity NPC228593
0.8023 Intermediate Similarity NPC472950
0.8023 Intermediate Similarity NPC472952
0.8021 Intermediate Similarity NPC113500
0.8021 Intermediate Similarity NPC3538
0.8021 Intermediate Similarity NPC477224
0.8 Intermediate Similarity NPC2096
0.8 Intermediate Similarity NPC134967
0.8 Intermediate Similarity NPC208912
0.8 Intermediate Similarity NPC114700
0.8 Intermediate Similarity NPC310138
0.8 Intermediate Similarity NPC470029
0.798 Intermediate Similarity NPC51579
0.7979 Intermediate Similarity NPC82955
0.7979 Intermediate Similarity NPC20822
0.7959 Intermediate Similarity NPC472273
0.7959 Intermediate Similarity NPC472145
0.7957 Intermediate Similarity NPC472396
0.7957 Intermediate Similarity NPC5943
0.7955 Intermediate Similarity NPC272841
0.7955 Intermediate Similarity NPC177343
0.7955 Intermediate Similarity NPC252483
0.7955 Intermediate Similarity NPC43463
0.7955 Intermediate Similarity NPC191345
0.7941 Intermediate Similarity NPC166079
0.7935 Intermediate Similarity NPC478111
0.7921 Intermediate Similarity NPC34562
0.7917 Intermediate Similarity NPC311246
0.7917 Intermediate Similarity NPC167644
0.7895 Intermediate Similarity NPC50443
0.7895 Intermediate Similarity NPC18536
0.7879 Intermediate Similarity NPC209798
0.7879 Intermediate Similarity NPC471374
0.7879 Intermediate Similarity NPC471375
0.7872 Intermediate Similarity NPC128475
0.7857 Intermediate Similarity NPC156377
0.7857 Intermediate Similarity NPC296936
0.7857 Intermediate Similarity NPC235109
0.7849 Intermediate Similarity NPC131365
0.7843 Intermediate Similarity NPC100078
0.7835 Intermediate Similarity NPC175
0.7835 Intermediate Similarity NPC30687
0.783 Intermediate Similarity NPC477489
0.7826 Intermediate Similarity NPC79308
0.7812 Intermediate Similarity NPC5632
0.7812 Intermediate Similarity NPC293609
0.7812 Intermediate Similarity NPC210759
0.7812 Intermediate Similarity NPC59006
0.7812 Intermediate Similarity NPC473066
0.7812 Intermediate Similarity NPC149966
0.7812 Intermediate Similarity NPC307167
0.7812 Intermediate Similarity NPC229801
0.7802 Intermediate Similarity NPC154043
0.7802 Intermediate Similarity NPC60018
0.7802 Intermediate Similarity NPC202688
0.78 Intermediate Similarity NPC471426
0.78 Intermediate Similarity NPC471428
0.78 Intermediate Similarity NPC471427
0.7778 Intermediate Similarity NPC477223
0.7778 Intermediate Similarity NPC198549
0.7778 Intermediate Similarity NPC113976
0.7778 Intermediate Similarity NPC477222
0.7767 Intermediate Similarity NPC291414
0.7767 Intermediate Similarity NPC306776
0.7766 Intermediate Similarity NPC210658
0.7766 Intermediate Similarity NPC161928
0.7766 Intermediate Similarity NPC140446
0.7766 Intermediate Similarity NPC43912
0.7757 Intermediate Similarity NPC97002
0.7755 Intermediate Similarity NPC473067
0.7755 Intermediate Similarity NPC473065
0.7755 Intermediate Similarity NPC473064
0.7755 Intermediate Similarity NPC82633
0.7755 Intermediate Similarity NPC215570
0.7742 Intermediate Similarity NPC266651
0.7742 Intermediate Similarity NPC290612
0.7742 Intermediate Similarity NPC477445
0.7732 Intermediate Similarity NPC277774
0.7727 Intermediate Similarity NPC136424
0.7723 Intermediate Similarity NPC477225
0.7723 Intermediate Similarity NPC476838
0.7723 Intermediate Similarity NPC476839
0.7717 Intermediate Similarity NPC477285
0.7717 Intermediate Similarity NPC111582
0.7708 Intermediate Similarity NPC473542
0.7708 Intermediate Similarity NPC279329
0.7701 Intermediate Similarity NPC166250
0.7701 Intermediate Similarity NPC308489
0.7701 Intermediate Similarity NPC470151
0.77 Intermediate Similarity NPC473638
0.7692 Intermediate Similarity NPC126753
0.7685 Intermediate Similarity NPC79193
0.7684 Intermediate Similarity NPC56777
0.7684 Intermediate Similarity NPC201607
0.7677 Intermediate Similarity NPC142264
0.7677 Intermediate Similarity NPC163685
0.7677 Intermediate Similarity NPC476510
0.7677 Intermediate Similarity NPC145553
0.7677 Intermediate Similarity NPC116683
0.7653 Intermediate Similarity NPC305418
0.7653 Intermediate Similarity NPC473774
0.7653 Intermediate Similarity NPC24960
0.7653 Intermediate Similarity NPC45959
0.7653 Intermediate Similarity NPC252253
0.7647 Intermediate Similarity NPC213528
0.7647 Intermediate Similarity NPC80640
0.7647 Intermediate Similarity NPC244969
0.7634 Intermediate Similarity NPC474156
0.7634 Intermediate Similarity NPC65133
0.7629 Intermediate Similarity NPC36372
0.7624 Intermediate Similarity NPC80417
0.7624 Intermediate Similarity NPC41843
0.7619 Intermediate Similarity NPC207693
0.7609 Intermediate Similarity NPC477286
0.7609 Intermediate Similarity NPC477284
0.7609 Intermediate Similarity NPC286719
0.7604 Intermediate Similarity NPC131466
0.7604 Intermediate Similarity NPC473472
0.76 Intermediate Similarity NPC233649
0.76 Intermediate Similarity NPC470591
0.76 Intermediate Similarity NPC74466
0.76 Intermediate Similarity NPC470632
0.76 Intermediate Similarity NPC470028
0.7582 Intermediate Similarity NPC16449
0.7582 Intermediate Similarity NPC475456
0.7576 Intermediate Similarity NPC477494
0.7576 Intermediate Similarity NPC92196

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC475307 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7374 Intermediate Similarity NPD8171 Discontinued
0.7356 Intermediate Similarity NPD7532 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD3670 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD3669 Approved
0.7333 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD1700 Approved
0.6964 Remote Similarity NPD8133 Approved
0.6957 Remote Similarity NPD7516 Approved
0.6909 Remote Similarity NPD4061 Clinical (unspecified phase)
0.687 Remote Similarity NPD7328 Approved
0.687 Remote Similarity NPD7327 Approved
0.6842 Remote Similarity NPD6928 Phase 2
0.6809 Remote Similarity NPD6697 Approved
0.6809 Remote Similarity NPD6118 Approved
0.6809 Remote Similarity NPD6115 Approved
0.6809 Remote Similarity NPD6114 Approved
0.6739 Remote Similarity NPD1811 Approved
0.6739 Remote Similarity NPD1810 Approved
0.6702 Remote Similarity NPD6116 Phase 1
0.6696 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6695 Remote Similarity NPD8380 Approved
0.6695 Remote Similarity NPD8296 Approved
0.6695 Remote Similarity NPD8379 Approved
0.6695 Remote Similarity NPD8335 Approved
0.6695 Remote Similarity NPD8378 Approved
0.6667 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6667 Remote Similarity NPD371 Approved
0.6667 Remote Similarity NPD6686 Approved
0.6638 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6612 Remote Similarity NPD7507 Approved
0.661 Remote Similarity NPD8294 Approved
0.661 Remote Similarity NPD8377 Approved
0.6598 Remote Similarity NPD1780 Approved
0.6598 Remote Similarity NPD1779 Approved
0.6596 Remote Similarity NPD6117 Approved
0.6585 Remote Similarity NPD7319 Approved
0.6555 Remote Similarity NPD8033 Approved
0.6552 Remote Similarity NPD6940 Discontinued
0.6484 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6412 Phase 2
0.6429 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6423 Remote Similarity NPD8293 Discontinued
0.6413 Remote Similarity NPD2686 Approved
0.6413 Remote Similarity NPD2687 Approved
0.6413 Remote Similarity NPD2254 Approved
0.6396 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6396 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6383 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6371 Remote Similarity NPD7736 Approved
0.6364 Remote Similarity NPD6370 Approved
0.6311 Remote Similarity NPD8328 Phase 3
0.6281 Remote Similarity NPD7503 Approved
0.626 Remote Similarity NPD7492 Approved
0.621 Remote Similarity NPD6616 Approved
0.6198 Remote Similarity NPD6059 Approved
0.6198 Remote Similarity NPD6054 Approved
0.616 Remote Similarity NPD7078 Approved
0.6148 Remote Similarity NPD6921 Approved
0.6146 Remote Similarity NPD3703 Phase 2
0.6126 Remote Similarity NPD5344 Discontinued
0.6091 Remote Similarity NPD4225 Approved
0.6091 Remote Similarity NPD7638 Approved
0.6048 Remote Similarity NPD6067 Discontinued
0.6047 Remote Similarity NPD2267 Suspended
0.6036 Remote Similarity NPD7640 Approved
0.6036 Remote Similarity NPD7639 Approved
0.6017 Remote Similarity NPD6882 Approved
0.6016 Remote Similarity NPD6016 Approved
0.6016 Remote Similarity NPD6015 Approved
0.6 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5981 Remote Similarity NPD8034 Phase 2
0.5981 Remote Similarity NPD8035 Phase 2
0.5979 Remote Similarity NPD3702 Approved
0.5968 Remote Similarity NPD5988 Approved
0.5963 Remote Similarity NPD7991 Discontinued
0.5957 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5957 Remote Similarity NPD3700 Clinical (unspecified phase)
0.595 Remote Similarity NPD6009 Approved
0.5935 Remote Similarity NPD6319 Approved
0.5929 Remote Similarity NPD8082 Approved
0.5929 Remote Similarity NPD8139 Approved
0.5929 Remote Similarity NPD8085 Approved
0.5929 Remote Similarity NPD7632 Discontinued
0.5929 Remote Similarity NPD8084 Approved
0.5929 Remote Similarity NPD8138 Approved
0.5929 Remote Similarity NPD8086 Approved
0.5929 Remote Similarity NPD8083 Approved
0.5913 Remote Similarity NPD6008 Approved
0.5887 Remote Similarity NPD8517 Approved
0.5887 Remote Similarity NPD8515 Approved
0.5887 Remote Similarity NPD8516 Approved
0.5887 Remote Similarity NPD8513 Phase 3
0.5882 Remote Similarity NPD8297 Approved
0.5877 Remote Similarity NPD8275 Approved
0.5877 Remote Similarity NPD8276 Approved
0.5865 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5777 Approved
0.5833 Remote Similarity NPD4632 Approved
0.5826 Remote Similarity NPD8081 Approved
0.582 Remote Similarity NPD7115 Discovery
0.5812 Remote Similarity NPD7320 Approved
0.5776 Remote Similarity NPD7128 Approved
0.5776 Remote Similarity NPD6402 Approved
0.5776 Remote Similarity NPD8393 Approved
0.5776 Remote Similarity NPD5739 Approved
0.5776 Remote Similarity NPD6675 Approved
0.5763 Remote Similarity NPD6373 Approved
0.5763 Remote Similarity NPD6372 Approved
0.5755 Remote Similarity NPD7524 Approved
0.5752 Remote Similarity NPD6648 Approved
0.5741 Remote Similarity NPD3168 Discontinued
0.5736 Remote Similarity NPD6033 Approved
0.5729 Remote Similarity NPD4244 Approved
0.5729 Remote Similarity NPD4245 Approved
0.5726 Remote Similarity NPD8140 Approved
0.5726 Remote Similarity NPD8307 Discontinued
0.5699 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5684 Remote Similarity NPD5360 Phase 3
0.5684 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5684 Remote Similarity NPD229 Approved
0.5678 Remote Similarity NPD6881 Approved
0.5678 Remote Similarity NPD6899 Approved
0.567 Remote Similarity NPD6081 Approved
0.5669 Remote Similarity NPD7604 Phase 2
0.5667 Remote Similarity NPD6650 Approved
0.5667 Remote Similarity NPD6649 Approved
0.5638 Remote Similarity NPD4224 Phase 2
0.5636 Remote Similarity NPD6399 Phase 3
0.563 Remote Similarity NPD8306 Approved
0.563 Remote Similarity NPD8305 Approved
0.5625 Remote Similarity NPD3698 Phase 2
0.5614 Remote Similarity NPD8418 Phase 2

Structure

External Identifiers

PubChem CID   44566822
ChEMBL   CHEMBL503258
ZINC  

Physicochemical Properties

Molecular Weight:  582.30
ALogP:  -1.2911
MLogP:  3.55
XLogP:  3.019
# Rotatable Bonds:  19
Polar Surface Area:  139.35
# H-Bond Aceptor:  11
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  41

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Biological Activities  
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