Natural Product: NPC474092

Natural Product ID:  NPC474092
Common Name:   3-O-[(1''-Hydroxyoctadecyloxy)-2'-Hydroxypropanoyl]Lupeol
IUPAC Name:   [(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] 2-hydroxy-3-(1-hydroxynonadecoxy)propanoate
Synonyms:  
Molecular Formula:   C52H92O5
Standard InCHIKey:  VAYVSQURRUAKLA-GPGLTNOESA-N
Standard InCHI:  InChI=1S/C52H92O5/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-45(54)56-37-41(53)47(55)57-44-31-33-50(7)42(48(44,4)5)30-34-52(9)43(50)28-27-40-46-39(38(2)3)29-32-49(46,6)35-36-51(40,52)8/h39-46,53-54H,2,10-37H2,1,3-9H3/t39-,40+,41?,42-,43+,44-,45?,46+,49+,50-,51+,52+/m0/s1
Canonical SMILES:  CCCCCCCCCCCCCCCCCCC(OCC(C(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C)C)C)O)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
NPO12483 Holarrhena floribunda Species Apocynaceae Eukaryota PMID[16441070]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 391000 ug/ml 26483137
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 500000 nM 8691203
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 391000 ug/ml 8691203
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 500000 nM 20805391

  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 NPC474092 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
0.8632 High Similarity NPC287118
0.8632 High Similarity NPC473690
0.8632 High Similarity NPC471902
0.8558 High Similarity NPC11035
0.8526 High Similarity NPC475416
0.8526 High Similarity NPC471901
0.8462 Intermediate Similarity NPC5280
0.8447 Intermediate Similarity NPC88744
0.8396 Intermediate Similarity NPC146563
0.8387 Intermediate Similarity NPC168231
0.8381 Intermediate Similarity NPC272242
0.837 Intermediate Similarity NPC239362
0.8365 Intermediate Similarity NPC473844
0.8365 Intermediate Similarity NPC91583
0.8365 Intermediate Similarity NPC240125
0.8365 Intermediate Similarity NPC51947
0.8316 Intermediate Similarity NPC213832
0.8316 Intermediate Similarity NPC57954
0.8302 Intermediate Similarity NPC243572
0.8302 Intermediate Similarity NPC470543
0.83 Intermediate Similarity NPC317019
0.8283 Intermediate Similarity NPC278939
0.8283 Intermediate Similarity NPC473555
0.8283 Intermediate Similarity NPC471770
0.8252 Intermediate Similarity NPC165405
0.8252 Intermediate Similarity NPC473199
0.8241 Intermediate Similarity NPC137414
0.8241 Intermediate Similarity NPC469820
0.8241 Intermediate Similarity NPC469823
0.8224 Intermediate Similarity NPC73986
0.8224 Intermediate Similarity NPC102619
0.8211 Intermediate Similarity NPC4309
0.8211 Intermediate Similarity NPC471900
0.8208 Intermediate Similarity NPC1876
0.8208 Intermediate Similarity NPC275668
0.8208 Intermediate Similarity NPC204392
0.8208 Intermediate Similarity NPC91838
0.8208 Intermediate Similarity NPC240734
0.82 Intermediate Similarity NPC157739
0.8198 Intermediate Similarity NPC470478
0.8182 Intermediate Similarity NPC472989
0.8173 Intermediate Similarity NPC234160
0.8148 Intermediate Similarity NPC54395
0.8137 Intermediate Similarity NPC94919
0.8132 Intermediate Similarity NPC304194
0.8125 Intermediate Similarity NPC220498
0.8105 Intermediate Similarity NPC269360
0.8105 Intermediate Similarity NPC264005
0.8105 Intermediate Similarity NPC33768
0.8095 Intermediate Similarity NPC472988
0.8095 Intermediate Similarity NPC224414
0.8095 Intermediate Similarity NPC38217
0.8091 Intermediate Similarity NPC469822
0.8041 Intermediate Similarity NPC169933
0.8022 Intermediate Similarity NPC305835
0.802 Intermediate Similarity NPC280825
0.802 Intermediate Similarity NPC234287
0.8019 Intermediate Similarity NPC51925
0.8019 Intermediate Similarity NPC296761
0.8019 Intermediate Similarity NPC154085
0.8019 Intermediate Similarity NPC43976
0.8019 Intermediate Similarity NPC125361
0.8 Intermediate Similarity NPC2783
0.8 Intermediate Similarity NPC12774
0.8 Intermediate Similarity NPC156651
0.7982 Intermediate Similarity NPC469821
0.7981 Intermediate Similarity NPC31430
0.7981 Intermediate Similarity NPC85593
0.798 Intermediate Similarity NPC277399
0.7979 Intermediate Similarity NPC299963
0.7959 Intermediate Similarity NPC160506
0.7959 Intermediate Similarity NPC48463
0.7959 Intermediate Similarity NPC219516
0.7944 Intermediate Similarity NPC242611
0.7944 Intermediate Similarity NPC106760
0.7941 Intermediate Similarity NPC7341
0.7941 Intermediate Similarity NPC473200
0.7935 Intermediate Similarity NPC206735
0.7928 Intermediate Similarity NPC239293
0.7925 Intermediate Similarity NPC195708
0.7917 Intermediate Similarity NPC252714
0.7913 Intermediate Similarity NPC273962
0.79 Intermediate Similarity NPC205173
0.7895 Intermediate Similarity NPC294438
0.7895 Intermediate Similarity NPC98270
0.7895 Intermediate Similarity NPC264317
0.7879 Intermediate Similarity NPC291373
0.7879 Intermediate Similarity NPC475061
0.7872 Intermediate Similarity NPC473742
0.787 Intermediate Similarity NPC285410
0.787 Intermediate Similarity NPC31839
0.787 Intermediate Similarity NPC65167
0.787 Intermediate Similarity NPC250481
0.787 Intermediate Similarity NPC263827
0.787 Intermediate Similarity NPC114188
0.787 Intermediate Similarity NPC270586
0.7864 Intermediate Similarity NPC88000
0.7864 Intermediate Similarity NPC121072
0.7864 Intermediate Similarity NPC472023
0.7864 Intermediate Similarity NPC470054
0.7864 Intermediate Similarity NPC289670
0.7864 Intermediate Similarity NPC129372
0.7864 Intermediate Similarity NPC4831
0.7864 Intermediate Similarity NPC31346
0.7864 Intermediate Similarity NPC21064
0.7864 Intermediate Similarity NPC309425
0.7864 Intermediate Similarity NPC47566
0.7864 Intermediate Similarity NPC160734
0.785 Intermediate Similarity NPC265655
0.785 Intermediate Similarity NPC8431
0.7843 Intermediate Similarity NPC102426
0.7843 Intermediate Similarity NPC469725
0.7843 Intermediate Similarity NPC300179
0.7838 Intermediate Similarity NPC224121
0.7835 Intermediate Similarity NPC16377
0.7835 Intermediate Similarity NPC474719
0.7835 Intermediate Similarity NPC146937
0.783 Intermediate Similarity NPC470170
0.783 Intermediate Similarity NPC283849
0.783 Intermediate Similarity NPC287269
0.783 Intermediate Similarity NPC470169
0.7822 Intermediate Similarity NPC327788
0.7818 Intermediate Similarity NPC116024
0.781 Intermediate Similarity NPC470060
0.781 Intermediate Similarity NPC470057
0.781 Intermediate Similarity NPC470062
0.781 Intermediate Similarity NPC470061
0.781 Intermediate Similarity NPC173583
0.781 Intermediate Similarity NPC470058
0.781 Intermediate Similarity NPC470064
0.781 Intermediate Similarity NPC470059
0.781 Intermediate Similarity NPC470043
0.78 Intermediate Similarity NPC211238
0.7798 Intermediate Similarity NPC48249
0.7798 Intermediate Similarity NPC1046
0.7798 Intermediate Similarity NPC100383
0.7798 Intermediate Similarity NPC80843
0.7789 Intermediate Similarity NPC475509
0.7788 Intermediate Similarity NPC288694
0.7788 Intermediate Similarity NPC154452
0.7788 Intermediate Similarity NPC159036
0.7788 Intermediate Similarity NPC177701
0.7788 Intermediate Similarity NPC136816
0.7788 Intermediate Similarity NPC312553
0.7788 Intermediate Similarity NPC470053
0.7788 Intermediate Similarity NPC31085
0.7778 Intermediate Similarity NPC120539
0.7778 Intermediate Similarity NPC90630
0.7778 Intermediate Similarity NPC129340
0.7778 Intermediate Similarity NPC101450
0.7778 Intermediate Similarity NPC475243
0.7768 Intermediate Similarity NPC286347
0.7767 Intermediate Similarity NPC94906
0.7766 Intermediate Similarity NPC472504
0.7757 Intermediate Similarity NPC177246
0.7757 Intermediate Similarity NPC284807
0.7757 Intermediate Similarity NPC28198
0.7757 Intermediate Similarity NPC476123
0.7757 Intermediate Similarity NPC230888
0.7757 Intermediate Similarity NPC63841
0.7757 Intermediate Similarity NPC295389
0.7755 Intermediate Similarity NPC253618
0.7755 Intermediate Similarity NPC77001
0.7745 Intermediate Similarity NPC253586
0.7745 Intermediate Similarity NPC76486
0.7736 Intermediate Similarity NPC470055
0.7736 Intermediate Similarity NPC475494
0.7736 Intermediate Similarity NPC470056
0.7736 Intermediate Similarity NPC265127
0.7732 Intermediate Similarity NPC134197
0.7727 Intermediate Similarity NPC144068
0.7727 Intermediate Similarity NPC475208
0.7727 Intermediate Similarity NPC238935
0.7723 Intermediate Similarity NPC210214
0.7717 Intermediate Similarity NPC102708
0.7714 Intermediate Similarity NPC473020
0.7714 Intermediate Similarity NPC155010
0.7714 Intermediate Similarity NPC16573
0.7714 Intermediate Similarity NPC31907
0.7714 Intermediate Similarity NPC131479
0.7714 Intermediate Similarity NPC211879
0.7714 Intermediate Similarity NPC471467
0.7714 Intermediate Similarity NPC213190
0.7714 Intermediate Similarity NPC472252
0.7714 Intermediate Similarity NPC245280
0.7714 Intermediate Similarity NPC120123
0.7714 Intermediate Similarity NPC286969
0.7714 Intermediate Similarity NPC157659
0.7714 Intermediate Similarity NPC114874
0.7714 Intermediate Similarity NPC16520
0.7714 Intermediate Similarity NPC189852
0.7714 Intermediate Similarity NPC473198
0.7714 Intermediate Similarity NPC8039
0.7708 Intermediate Similarity NPC201655
0.7706 Intermediate Similarity NPC274833
0.7706 Intermediate Similarity NPC292196
0.77 Intermediate Similarity NPC246860
0.7699 Intermediate Similarity NPC469945
0.7699 Intermediate Similarity NPC114441
0.7699 Intermediate Similarity NPC475171

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474092 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
0.7959 Intermediate Similarity NPD8035 Phase 2
0.7959 Intermediate Similarity NPD8034 Phase 2
0.7895 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD8133 Approved
0.7522 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD7736 Approved
0.7436 Intermediate Similarity NPD8328 Phase 3
0.7328 Intermediate Similarity NPD8377 Approved
0.7328 Intermediate Similarity NPD8294 Approved
0.7304 Intermediate Similarity NPD7327 Approved
0.7304 Intermediate Similarity NPD7328 Approved
0.7265 Intermediate Similarity NPD8380 Approved
0.7265 Intermediate Similarity NPD8335 Approved
0.7265 Intermediate Similarity NPD8379 Approved
0.7265 Intermediate Similarity NPD8033 Approved
0.7265 Intermediate Similarity NPD8378 Approved
0.7265 Intermediate Similarity NPD8296 Approved
0.725 Intermediate Similarity NPD8293 Discontinued
0.7241 Intermediate Similarity NPD7516 Approved
0.7168 Intermediate Similarity NPD8297 Approved
0.7131 Intermediate Similarity NPD7319 Approved
0.7115 Intermediate Similarity NPD7748 Approved
0.7091 Intermediate Similarity NPD7128 Approved
0.7091 Intermediate Similarity NPD6402 Approved
0.7091 Intermediate Similarity NPD5739 Approved
0.7091 Intermediate Similarity NPD6675 Approved
0.7069 Intermediate Similarity NPD7115 Discovery
0.7059 Intermediate Similarity NPD6370 Approved
0.7054 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD6412 Phase 2
0.7025 Intermediate Similarity NPD7507 Approved
0.7018 Intermediate Similarity NPD6882 Approved
0.701 Intermediate Similarity NPD7525 Registered
0.7009 Intermediate Similarity NPD7638 Approved
0.7009 Intermediate Similarity NPD4225 Approved
0.6964 Remote Similarity NPD7320 Approved
0.6964 Remote Similarity NPD6881 Approved
0.6964 Remote Similarity NPD6899 Approved
0.6947 Remote Similarity NPD6117 Approved
0.6944 Remote Similarity NPD7640 Approved
0.6944 Remote Similarity NPD7639 Approved
0.6942 Remote Similarity NPD7492 Approved
0.693 Remote Similarity NPD8130 Phase 1
0.6923 Remote Similarity NPD7515 Phase 2
0.6916 Remote Similarity NPD6083 Phase 2
0.6916 Remote Similarity NPD7902 Approved
0.6916 Remote Similarity NPD6084 Phase 2
0.6907 Remote Similarity NPD7645 Phase 2
0.6903 Remote Similarity NPD6372 Approved
0.6903 Remote Similarity NPD6373 Approved
0.6891 Remote Similarity NPD6054 Approved
0.6891 Remote Similarity NPD6319 Approved
0.6891 Remote Similarity NPD6059 Approved
0.6885 Remote Similarity NPD6616 Approved
0.6875 Remote Similarity NPD5701 Approved
0.6875 Remote Similarity NPD5697 Approved
0.6875 Remote Similarity NPD6116 Phase 1
0.6857 Remote Similarity NPD8171 Discontinued
0.6857 Remote Similarity NPD6399 Phase 3
0.6848 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7290 Approved
0.6842 Remote Similarity NPD7102 Approved
0.6842 Remote Similarity NPD6883 Approved
0.6833 Remote Similarity NPD7503 Approved
0.6829 Remote Similarity NPD7078 Approved
0.6814 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6804 Remote Similarity NPD6697 Approved
0.6804 Remote Similarity NPD6118 Approved
0.6804 Remote Similarity NPD6115 Approved
0.6804 Remote Similarity NPD6114 Approved
0.6783 Remote Similarity NPD6650 Approved
0.6783 Remote Similarity NPD6869 Approved
0.6783 Remote Similarity NPD6847 Approved
0.6783 Remote Similarity NPD6649 Approved
0.6783 Remote Similarity NPD6617 Approved
0.6754 Remote Similarity NPD6014 Approved
0.6754 Remote Similarity NPD6013 Approved
0.6754 Remote Similarity NPD6012 Approved
0.6737 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6696 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6694 Remote Similarity NPD6015 Approved
0.6694 Remote Similarity NPD6016 Approved
0.6667 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD6686 Approved
0.6639 Remote Similarity NPD6009 Approved
0.6639 Remote Similarity NPD5988 Approved
0.6638 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6636 Remote Similarity NPD7900 Approved
0.6636 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6635 Remote Similarity NPD5737 Approved
0.6635 Remote Similarity NPD6672 Approved
0.6606 Remote Similarity NPD4755 Approved
0.6604 Remote Similarity NPD7637 Suspended
0.6574 Remote Similarity NPD5695 Phase 3
0.6571 Remote Similarity NPD5328 Approved
0.6569 Remote Similarity NPD4786 Approved
0.6552 Remote Similarity NPD4634 Approved
0.6545 Remote Similarity NPD5696 Approved
0.6518 Remote Similarity NPD7632 Discontinued
0.6514 Remote Similarity NPD5221 Approved
0.6514 Remote Similarity NPD4697 Phase 3
0.6514 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6514 Remote Similarity NPD5222 Approved
0.6495 Remote Similarity NPD7339 Approved
0.6495 Remote Similarity NPD6942 Approved
0.6486 Remote Similarity NPD4696 Approved
0.6486 Remote Similarity NPD5285 Approved
0.6486 Remote Similarity NPD4700 Approved
0.6486 Remote Similarity NPD5286 Approved
0.6476 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4788 Approved
0.6455 Remote Similarity NPD5173 Approved
0.6449 Remote Similarity NPD6079 Approved
0.6442 Remote Similarity NPD3618 Phase 1
0.6417 Remote Similarity NPD6274 Approved
0.6417 Remote Similarity NPD6868 Approved
0.6415 Remote Similarity NPD4753 Phase 2
0.6393 Remote Similarity NPD7100 Approved
0.6393 Remote Similarity NPD7101 Approved
0.6381 Remote Similarity NPD7524 Approved
0.6378 Remote Similarity NPD6033 Approved
0.6373 Remote Similarity NPD3667 Approved
0.6372 Remote Similarity NPD5211 Phase 2
0.6372 Remote Similarity NPD4633 Approved
0.6372 Remote Similarity NPD5225 Approved
0.6372 Remote Similarity NPD5224 Approved
0.6372 Remote Similarity NPD5226 Approved
0.6354 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6354 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6337 Remote Similarity NPD6928 Phase 2
0.632 Remote Similarity NPD7604 Phase 2
0.6316 Remote Similarity NPD5174 Approved
0.6316 Remote Similarity NPD5175 Approved
0.6311 Remote Similarity NPD6335 Approved
0.6296 Remote Similarity NPD6411 Approved
0.629 Remote Similarity NPD6909 Approved
0.629 Remote Similarity NPD6908 Approved
0.629 Remote Similarity NPD5983 Phase 2
0.6286 Remote Similarity NPD7334 Approved
0.6286 Remote Similarity NPD6409 Approved
0.6286 Remote Similarity NPD5330 Approved
0.6286 Remote Similarity NPD7146 Approved
0.6286 Remote Similarity NPD6684 Approved
0.6286 Remote Similarity NPD7521 Approved
0.6286 Remote Similarity NPD6098 Approved
0.6283 Remote Similarity NPD5223 Approved
0.6281 Remote Similarity NPD6940 Discontinued
0.6263 Remote Similarity NPD6933 Approved
0.6263 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6262 Remote Similarity NPD6673 Approved
0.6262 Remote Similarity NPD6080 Approved
0.6262 Remote Similarity NPD6904 Approved
0.6262 Remote Similarity NPD6051 Approved
0.6261 Remote Similarity NPD5141 Approved
0.625 Remote Similarity NPD4789 Approved
0.6239 Remote Similarity NPD4202 Approved
0.623 Remote Similarity NPD6317 Approved
0.622 Remote Similarity NPD6336 Discontinued
0.6207 Remote Similarity NPD4767 Approved
0.6207 Remote Similarity NPD4768 Approved
0.619 Remote Similarity NPD6067 Discontinued
0.6186 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6179 Remote Similarity NPD6313 Approved
0.6179 Remote Similarity NPD6314 Approved
0.6174 Remote Similarity NPD4754 Approved
0.6168 Remote Similarity NPD6903 Approved
0.616 Remote Similarity NPD8516 Approved
0.616 Remote Similarity NPD8515 Approved
0.616 Remote Similarity NPD8517 Approved
0.616 Remote Similarity NPD6921 Approved
0.616 Remote Similarity NPD8513 Phase 3
0.6154 Remote Similarity NPD6695 Phase 3
0.6146 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6146 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6132 Remote Similarity NPD5279 Phase 3
0.6126 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6126 Remote Similarity NPD5210 Approved
0.6126 Remote Similarity NPD4629 Approved
0.6111 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6101 Approved
0.6102 Remote Similarity NPD4730 Approved
0.6102 Remote Similarity NPD4729 Approved
0.6102 Remote Similarity NPD5128 Approved
0.6095 Remote Similarity NPD3666 Approved
0.6095 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6095 Remote Similarity NPD3133 Approved
0.6095 Remote Similarity NPD3665 Phase 1
0.6075 Remote Similarity NPD7750 Discontinued
0.6061 Remote Similarity NPD6926 Approved
0.6061 Remote Similarity NPD6924 Approved
0.6038 Remote Similarity NPD5329 Approved
0.6032 Remote Similarity NPD6291 Clinical (unspecified phase)
0.602 Remote Similarity NPD6081 Approved
0.602 Remote Similarity NPD5777 Approved
0.6 Remote Similarity NPD5251 Approved
0.6 Remote Similarity NPD5250 Approved
0.6 Remote Similarity NPD5249 Phase 3
0.6 Remote Similarity NPD6050 Approved
0.6 Remote Similarity NPD5248 Approved

Structure

External Identifiers

PubChem CID   44566237
ChEMBL   CHEMBL461073
ZINC  

Physicochemical Properties

Molecular Weight:  796.69
ALogP:  -2.3322
MLogP:  6.63
XLogP:  20.867
# Rotatable Bonds:  34
Polar Surface Area:  75.99
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  57

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Biological Activities  
Similar NPs/Drugs