Natural Product: NPC477291

Natural Product ID:  NPC477291
Common Name:   [(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-[3-[4-(3-aminopropyl)piperazin-1-yl]propylcarbamoyl]-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] acetate
IUPAC Name:   [(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-[3-[4-(3-aminopropyl)piperazin-1-yl]propylcarbamoyl]-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] acetate
Synonyms:  
Molecular Formula:   C42H72N4O3
Standard InCHIKey:  IUJKWMKQXCXZKK-BLNYKQIKSA-N
Standard InCHI:  InChI=1S/C42H72N4O3/c1-29-13-18-42(37(48)44-22-10-24-46-27-25-45(26-28-46)23-9-21-43)20-19-40(7)32(36(42)30(29)2)11-12-34-39(6)16-15-35(49-31(3)47)38(4,5)33(39)14-17-41(34,40)8/h11,29-30,33-36H,9-10,12-28,43H2,1-8H3,(H,44,48)/t29-,30+,33+,34-,35+,36+,39+,40-,41-,42+/m1/s1
Canonical SMILES:  NCCCN1CCN(CC1)CCCN=C([C@@]12CC[C@H]([C@@H]([C@H]2C2=CC[C@H]3[C@@]([C@@]2(CC1)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)OC(=O)C)C)C)O
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
NPO26571 Ilex paraguariensis Species Aquifoliaceae Eukaryota leaves Mato Leitao, RS, Brazil PMID[18192087]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 460 nM 17967541
NPT2 Others Unspecified Ratio = 0.37 17967541
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 170 nM 17967541
NPT171 Cell Line MRC5 Homo sapiens IC50 = 1610 nM 17967541
NPT2249 Individual Protein Histidine-rich protein Plasmodium falciparum Inhibition = 12.9 % 17967541
NPT2249 Individual Protein Histidine-rich protein Plasmodium falciparum Inhibition = 24.6 % 17967541
NPT2249 Individual Protein Histidine-rich protein Plasmodium falciparum IC50 > 20000000 nM 17967541
NPT2249 Individual Protein Histidine-rich protein Plasmodium falciparum Ratio IC50 > 3.4 17967541
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens IC50 > 500000 nM 18192087

  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 NPC477291 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
0.9231 High Similarity NPC477292
0.7699 Intermediate Similarity NPC258130
0.75 Intermediate Similarity NPC191965
0.7429 Intermediate Similarity NPC84121
0.7429 Intermediate Similarity NPC137306
0.7282 Intermediate Similarity NPC290495
0.7282 Intermediate Similarity NPC195334
0.7212 Intermediate Similarity NPC286786
0.7156 Intermediate Similarity NPC120840
0.7156 Intermediate Similarity NPC113989
0.7143 Intermediate Similarity NPC132386
0.7115 Intermediate Similarity NPC108476
0.7091 Intermediate Similarity NPC285184
0.7091 Intermediate Similarity NPC77099
0.7091 Intermediate Similarity NPC470590
0.7091 Intermediate Similarity NPC60755
0.7083 Intermediate Similarity NPC79238
0.7064 Intermediate Similarity NPC30522
0.7031 Intermediate Similarity NPC237286
0.7027 Intermediate Similarity NPC86368
0.7 Intermediate Similarity NPC474728
0.6972 Remote Similarity NPC40552
0.6972 Remote Similarity NPC246708
0.6964 Remote Similarity NPC184006
0.6964 Remote Similarity NPC78580
0.6964 Remote Similarity NPC215700
0.6964 Remote Similarity NPC74751
0.6964 Remote Similarity NPC23621
0.6964 Remote Similarity NPC296164
0.6944 Remote Similarity NPC10005
0.6944 Remote Similarity NPC329943
0.6944 Remote Similarity NPC9892
0.6944 Remote Similarity NPC91525
0.6942 Remote Similarity NPC474459
0.6942 Remote Similarity NPC66862
0.693 Remote Similarity NPC158347
0.693 Remote Similarity NPC474164
0.6929 Remote Similarity NPC472458
0.6909 Remote Similarity NPC470588
0.6903 Remote Similarity NPC23241
0.6903 Remote Similarity NPC474727
0.6903 Remote Similarity NPC195715
0.6885 Remote Similarity NPC469968
0.6885 Remote Similarity NPC474452
0.6885 Remote Similarity NPC80834
0.6881 Remote Similarity NPC51700
0.6881 Remote Similarity NPC130577
0.6881 Remote Similarity NPC46912
0.6881 Remote Similarity NPC68160
0.6881 Remote Similarity NPC98442
0.6881 Remote Similarity NPC142415
0.6881 Remote Similarity NPC242468
0.6881 Remote Similarity NPC102683
0.6881 Remote Similarity NPC162107
0.6881 Remote Similarity NPC307426
0.6881 Remote Similarity NPC88716
0.6881 Remote Similarity NPC18064
0.6881 Remote Similarity NPC293564
0.6881 Remote Similarity NPC171203
0.6875 Remote Similarity NPC474436
0.6875 Remote Similarity NPC63118
0.6875 Remote Similarity NPC49776
0.686 Remote Similarity NPC472313
0.685 Remote Similarity NPC242692
0.6842 Remote Similarity NPC327179
0.6842 Remote Similarity NPC230151
0.6838 Remote Similarity NPC176012
0.6829 Remote Similarity NPC478137
0.6818 Remote Similarity NPC181225
0.6818 Remote Similarity NPC17733
0.6818 Remote Similarity NPC470629
0.6818 Remote Similarity NPC290690
0.6818 Remote Similarity NPC52169
0.6818 Remote Similarity NPC224145
0.6818 Remote Similarity NPC473242
0.6818 Remote Similarity NPC182797
0.6818 Remote Similarity NPC474512
0.6807 Remote Similarity NPC86906
0.6792 Remote Similarity NPC142163
0.6789 Remote Similarity NPC72638
0.6789 Remote Similarity NPC325594
0.6783 Remote Similarity NPC476878
0.6783 Remote Similarity NPC26413
0.6783 Remote Similarity NPC476879
0.6777 Remote Similarity NPC85001
0.6777 Remote Similarity NPC95920
0.6777 Remote Similarity NPC253645
0.6777 Remote Similarity NPC147835
0.6757 Remote Similarity NPC198664
0.6757 Remote Similarity NPC127689
0.6757 Remote Similarity NPC274330
0.6757 Remote Similarity NPC270768
0.6757 Remote Similarity NPC225585
0.6757 Remote Similarity NPC95246
0.6757 Remote Similarity NPC293048
0.6757 Remote Similarity NPC59263
0.6757 Remote Similarity NPC234346
0.6757 Remote Similarity NPC121798
0.6757 Remote Similarity NPC25906
0.6757 Remote Similarity NPC64872
0.6757 Remote Similarity NPC475049
0.6757 Remote Similarity NPC290972
0.6757 Remote Similarity NPC161751
0.6757 Remote Similarity NPC130520
0.6757 Remote Similarity NPC61543
0.6757 Remote Similarity NPC143232
0.6757 Remote Similarity NPC474972
0.6757 Remote Similarity NPC263393
0.6731 Remote Similarity NPC101475
0.6731 Remote Similarity NPC157996
0.6731 Remote Similarity NPC34177
0.6731 Remote Similarity NPC84868
0.6731 Remote Similarity NPC40394
0.6726 Remote Similarity NPC74855
0.6726 Remote Similarity NPC136313
0.6726 Remote Similarity NPC295643
0.6726 Remote Similarity NPC272075
0.6726 Remote Similarity NPC214756
0.6726 Remote Similarity NPC307335
0.6724 Remote Similarity NPC471966
0.6724 Remote Similarity NPC58942
0.6724 Remote Similarity NPC477876
0.6724 Remote Similarity NPC477875
0.6724 Remote Similarity NPC260149
0.6721 Remote Similarity NPC72753
0.6696 Remote Similarity NPC210037
0.6696 Remote Similarity NPC7260
0.6696 Remote Similarity NPC470589
0.6696 Remote Similarity NPC273621
0.6696 Remote Similarity NPC126369
0.6696 Remote Similarity NPC172361
0.6696 Remote Similarity NPC290614
0.6696 Remote Similarity NPC477872
0.6696 Remote Similarity NPC291028
0.6696 Remote Similarity NPC130278
0.6696 Remote Similarity NPC86372
0.6696 Remote Similarity NPC227467
0.6696 Remote Similarity NPC18872
0.6696 Remote Similarity NPC120968
0.6696 Remote Similarity NPC111110
0.6667 Remote Similarity NPC474989
0.6667 Remote Similarity NPC476195
0.6667 Remote Similarity NPC22955
0.6667 Remote Similarity NPC474789
0.6667 Remote Similarity NPC196753
0.6667 Remote Similarity NPC98386
0.6667 Remote Similarity NPC473576
0.6667 Remote Similarity NPC158662
0.6667 Remote Similarity NPC474963
0.6667 Remote Similarity NPC246956
0.6667 Remote Similarity NPC470396
0.6667 Remote Similarity NPC5280
0.6667 Remote Similarity NPC474571
0.6667 Remote Similarity NPC475156
0.6667 Remote Similarity NPC300499
0.6667 Remote Similarity NPC230295
0.6667 Remote Similarity NPC254567
0.6667 Remote Similarity NPC91010
0.6667 Remote Similarity NPC99168
0.6667 Remote Similarity NPC474190
0.6667 Remote Similarity NPC253807
0.6667 Remote Similarity NPC52108
0.6639 Remote Similarity NPC218602
0.6637 Remote Similarity NPC474525
0.6637 Remote Similarity NPC966
0.6637 Remote Similarity NPC472149
0.6637 Remote Similarity NPC306541
0.6637 Remote Similarity NPC105189
0.6637 Remote Similarity NPC155120
0.6637 Remote Similarity NPC84319
0.6637 Remote Similarity NPC25299
0.6637 Remote Similarity NPC282616
0.6637 Remote Similarity NPC235884
0.6637 Remote Similarity NPC288833
0.6637 Remote Similarity NPC324341
0.6637 Remote Similarity NPC145067
0.6637 Remote Similarity NPC476064
0.6637 Remote Similarity NPC4036
0.6637 Remote Similarity NPC52021
0.6637 Remote Similarity NPC300351
0.6637 Remote Similarity NPC65120
0.6637 Remote Similarity NPC71074
0.6637 Remote Similarity NPC158030
0.6637 Remote Similarity NPC187722
0.6637 Remote Similarity NPC233455
0.6637 Remote Similarity NPC228784
0.6636 Remote Similarity NPC116202
0.6636 Remote Similarity NPC474970
0.6635 Remote Similarity NPC290598
0.6635 Remote Similarity NPC122418
0.6635 Remote Similarity NPC120098
0.6635 Remote Similarity NPC27765
0.6635 Remote Similarity NPC265328
0.6635 Remote Similarity NPC30590
0.661 Remote Similarity NPC473160
0.661 Remote Similarity NPC476132
0.661 Remote Similarity NPC233012
0.661 Remote Similarity NPC54909
0.661 Remote Similarity NPC235920
0.661 Remote Similarity NPC96784

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477291 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
0.6964 Remote Similarity NPD7748 Approved
0.6783 Remote Similarity NPD7902 Approved
0.6762 Remote Similarity NPD7645 Phase 2
0.6637 Remote Similarity NPD7515 Phase 2
0.6522 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7900 Approved
0.641 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6212 Remote Similarity NPD6909 Approved
0.6212 Remote Similarity NPD6908 Approved
0.6207 Remote Similarity NPD8035 Phase 2
0.6207 Remote Similarity NPD8034 Phase 2
0.6202 Remote Similarity NPD7754 Approved
0.6202 Remote Similarity NPD7755 Approved
0.6115 Remote Similarity NPD8449 Approved
0.6106 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6094 Remote Similarity NPD8077 Approved
0.6094 Remote Similarity NPD8078 Approved
0.608 Remote Similarity NPD7990 Approved
0.608 Remote Similarity NPD7989 Approved
0.6071 Remote Similarity NPD8450 Suspended
0.6053 Remote Similarity NPD8308 Discontinued
0.6047 Remote Similarity NPD8298 Phase 2
0.6033 Remote Similarity NPD7638 Approved
0.6017 Remote Similarity NPD6399 Phase 3
0.6017 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5984 Remote Similarity NPD7639 Approved
0.5984 Remote Similarity NPD7640 Approved
0.5971 Remote Similarity NPD6914 Discontinued
0.5952 Remote Similarity NPD7646 Clinical (unspecified phase)
0.5948 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5946 Remote Similarity NPD7525 Registered
0.5873 Remote Similarity NPD5357 Phase 1
0.5862 Remote Similarity NPD3573 Approved
0.5857 Remote Similarity NPD7751 Phase 1
0.584 Remote Similarity NPD7986 Approved
0.584 Remote Similarity NPD7911 Approved
0.584 Remote Similarity NPD7912 Approved
0.584 Remote Similarity NPD7987 Approved
0.5833 Remote Similarity NPD5707 Approved
0.578 Remote Similarity NPD6942 Approved
0.578 Remote Similarity NPD7339 Approved
0.5776 Remote Similarity NPD7521 Approved
0.5776 Remote Similarity NPD6684 Approved
0.5776 Remote Similarity NPD3618 Phase 1
0.5776 Remote Similarity NPD7334 Approved
0.5776 Remote Similarity NPD7146 Approved
0.5776 Remote Similarity NPD6409 Approved
0.5776 Remote Similarity NPD5330 Approved
0.5772 Remote Similarity NPD8088 Phase 1
0.5766 Remote Similarity NPD8328 Phase 3
0.5766 Remote Similarity NPD7122 Discontinued
0.5763 Remote Similarity NPD5328 Approved
0.5748 Remote Similarity NPD6675 Approved
0.5748 Remote Similarity NPD5739 Approved
0.5748 Remote Similarity NPD8040 Discontinued
0.5748 Remote Similarity NPD6402 Approved
0.5748 Remote Similarity NPD7128 Approved
0.5739 Remote Similarity NPD4786 Approved
0.5738 Remote Similarity NPD7732 Phase 3
0.5738 Remote Similarity NPD7614 Phase 1
0.5736 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5727 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5726 Remote Similarity NPD6404 Discontinued
0.5714 Remote Similarity NPD5354 Approved
0.5702 Remote Similarity NPD3667 Approved
0.5691 Remote Similarity NPD7920 Phase 3
0.5691 Remote Similarity NPD7919 Phase 3
0.5678 Remote Similarity NPD6903 Approved
0.5676 Remote Similarity NPD8143 Approved
0.5676 Remote Similarity NPD8144 Approved
0.5672 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5667 Remote Similarity NPD6411 Approved
0.5667 Remote Similarity NPD6079 Approved
0.5662 Remote Similarity NPD8294 Approved
0.5662 Remote Similarity NPD8377 Approved
0.5659 Remote Similarity NPD7320 Approved
0.5659 Remote Similarity NPD6899 Approved
0.5659 Remote Similarity NPD6881 Approved
0.5649 Remote Similarity NPD8130 Phase 1
0.5643 Remote Similarity NPD7746 Phase 1
0.5643 Remote Similarity NPD7747 Phase 1
0.563 Remote Similarity NPD6051 Approved
0.563 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5625 Remote Similarity NPD7333 Discontinued
0.562 Remote Similarity NPD8296 Approved
0.562 Remote Similarity NPD8380 Approved
0.562 Remote Similarity NPD8335 Approved
0.562 Remote Similarity NPD8033 Approved
0.562 Remote Similarity NPD8379 Approved
0.562 Remote Similarity NPD6921 Approved
0.562 Remote Similarity NPD8378 Approved
0.5615 Remote Similarity NPD6373 Approved
0.5615 Remote Similarity NPD6372 Approved
0.5606 Remote Similarity NPD8297 Approved
0.5606 Remote Similarity NPD7337 Clinical (unspecified phase)
0.5606 Remote Similarity NPD7336 Phase 2
0.5606 Remote Similarity NPD7335 Phase 2
0.56 Remote Similarity NPD8418 Phase 2

Structure

External Identifiers

PubChem CID   25111796
ChEMBL   CHEMBL270215
ZINC  

Physicochemical Properties

Molecular Weight:  680.56
ALogP:  0.5902
MLogP:  5.31
XLogP:  9.338
# Rotatable Bonds:  20
Polar Surface Area:  91.39
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  49

Download Data

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Biological Activities  
Similar NPs/Drugs