Structure

Physi-Chem Properties

Molecular Weight:  822.44
Volume:  807.776
LogP:  3.024
LogD:  2.729
LogS:  -4.245
# Rotatable Bonds:  10
TPSA:  205.2
# H-Bond Aceptor:  15
# H-Bond Donor:  5
# Rings:  8
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.168
Synthetic Accessibility Score:  6.333
Fsp3:  0.884
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.981
MDCK Permeability:  0.00010110389848705381
Pgp-inhibitor:  0.001
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.024
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.121
Plasma Protein Binding (PPB):  62.09258270263672%
Volume Distribution (VD):  0.476
Pgp-substrate:  15.908648490905762%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.987
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.328
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.004
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.049
CYP3A4-inhibitor:  0.649
CYP3A4-substrate:  0.908

ADMET: Excretion

Clearance (CL):  3.353
Half-life (T1/2):  0.12

ADMET: Toxicity

hERG Blockers:  0.855
Human Hepatotoxicity (H-HT):  0.257
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.853
Rat Oral Acute Toxicity:  0.971
Maximum Recommended Daily Dose:  0.99
Skin Sensitization:  0.921
Carcinogencity:  0.861
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.979

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC329636

Natural Product ID:  NPC329636
Common Name*:   Madagascarensilide C
IUPAC Name:   (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5R,6R)-5-[(2S,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms:   Madagascarensilide C
Standard InCHIKey:  OKKMMWPTBZXHLN-QTRLOGHOSA-N
Standard InCHI:  InChI=1S/C43H66O15/c1-22-37(47)31(50-5)17-35(53-22)58-39-24(3)55-36(18-32(39)51-6)57-38-23(2)54-34(16-30(38)45)56-26-7-12-41(21-44)28-8-11-40(4)27(25-15-33(46)52-20-25)10-14-43(40,49)29(28)9-13-42(41,48)19-26/h15,21-24,26-32,34-39,45,47-49H,7-14,16-20H2,1-6H3/t22-,23-,24-,26+,27-,28+,29-,30+,31-,32+,34+,35+,36+,37+,38-,39-,40-,41+,42+,43+/m1/s1
SMILES:  CC1C(C(CC(O1)OC2C(OC(CC2OC)OC3C(OC(CC3O)OC4CCC5(C6CCC7(C(CCC7(C6CCC5(C4)O)O)C8=CC(=O)OC8)C)C=O)C)C)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1644521
PubChem CID:   53323542
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001555] Cardenolides and derivatives
            • [CHEMONTID:0001559] Cardenolide glycosides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO33348 leptadenia madagascariensis Species Apocynaceae Eukaryota n.a. Madagascar dry forest n.a. PMID[21159516]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT179 Cell Line A2780 Homo sapiens IC50 = 170.0 nM PMID[498397]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 370.0 nM PMID[498397]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC329636 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
0.9919 High Similarity NPC194716
0.9918 High Similarity NPC116075
0.9918 High Similarity NPC32793
0.9918 High Similarity NPC146857
0.9918 High Similarity NPC247190
0.9918 High Similarity NPC469749
0.9839 High Similarity NPC329675
0.968 High Similarity NPC59288
0.9672 High Similarity NPC471358
0.9672 High Similarity NPC140092
0.9672 High Similarity NPC232785
0.9672 High Similarity NPC471361
0.9672 High Similarity NPC6108
0.9672 High Similarity NPC70542
0.9672 High Similarity NPC471360
0.9672 High Similarity NPC86159
0.9672 High Similarity NPC10823
0.9672 High Similarity NPC197707
0.9672 High Similarity NPC469754
0.9672 High Similarity NPC471359
0.9672 High Similarity NPC469752
0.9672 High Similarity NPC188234
0.9672 High Similarity NPC9499
0.9672 High Similarity NPC284406
0.9672 High Similarity NPC469753
0.9672 High Similarity NPC276838
0.9672 High Similarity NPC89514
0.9672 High Similarity NPC219085
0.9672 High Similarity NPC469755
0.9672 High Similarity NPC125077
0.9672 High Similarity NPC180079
0.9672 High Similarity NPC329986
0.9672 High Similarity NPC469751
0.9672 High Similarity NPC471352
0.9672 High Similarity NPC17896
0.9672 High Similarity NPC251866
0.9597 High Similarity NPC477709
0.9597 High Similarity NPC476221
0.9516 High Similarity NPC93416
0.9508 High Similarity NPC117702
0.9508 High Similarity NPC471356
0.9508 High Similarity NPC471357
0.9508 High Similarity NPC179412
0.9508 High Similarity NPC146456
0.9508 High Similarity NPC329784
0.9508 High Similarity NPC240070
0.9508 High Similarity NPC469757
0.9435 High Similarity NPC16569
0.9435 High Similarity NPC159338
0.9435 High Similarity NPC253456
0.9426 High Similarity NPC469750
0.9426 High Similarity NPC250556
0.936 High Similarity NPC19124
0.936 High Similarity NPC42670
0.9355 High Similarity NPC91
0.9286 High Similarity NPC225385
0.9286 High Similarity NPC157817
0.9286 High Similarity NPC104585
0.9286 High Similarity NPC142756
0.9286 High Similarity NPC298783
0.9262 High Similarity NPC27363
0.9141 High Similarity NPC171619
0.912 High Similarity NPC311534
0.9098 High Similarity NPC314535
0.9098 High Similarity NPC173555
0.907 High Similarity NPC289700
0.907 High Similarity NPC62172
0.9016 High Similarity NPC475629
0.9016 High Similarity NPC72260
0.9016 High Similarity NPC475556
0.8984 High Similarity NPC88668
0.8976 High Similarity NPC173347
0.8952 High Similarity NPC117445
0.8952 High Similarity NPC308262
0.8952 High Similarity NPC208193
0.8943 High Similarity NPC120390
0.8943 High Similarity NPC475419
0.8943 High Similarity NPC474908
0.8943 High Similarity NPC475590
0.8934 High Similarity NPC55532
0.8934 High Similarity NPC30483
0.8934 High Similarity NPC236973
0.8934 High Similarity NPC32177
0.8934 High Similarity NPC469756
0.8934 High Similarity NPC470897
0.8934 High Similarity NPC292467
0.8931 High Similarity NPC75616
0.8871 High Similarity NPC74259
0.8871 High Similarity NPC264336
0.8871 High Similarity NPC474423
0.8871 High Similarity NPC193893
0.8862 High Similarity NPC475136
0.8862 High Similarity NPC470312
0.8862 High Similarity NPC474466
0.8862 High Similarity NPC476150
0.8862 High Similarity NPC476127
0.879 High Similarity NPC40749
0.879 High Similarity NPC231518
0.879 High Similarity NPC475219
0.878 High Similarity NPC329905
0.8779 High Similarity NPC127656
0.877 High Similarity NPC474418
0.877 High Similarity NPC93883
0.877 High Similarity NPC50305
0.877 High Similarity NPC142066
0.877 High Similarity NPC471354
0.877 High Similarity NPC243196
0.877 High Similarity NPC471353
0.877 High Similarity NPC34390
0.877 High Similarity NPC244402
0.877 High Similarity NPC196429
0.877 High Similarity NPC471351
0.877 High Similarity NPC158344
0.877 High Similarity NPC309034
0.877 High Similarity NPC157376
0.877 High Similarity NPC99728
0.877 High Similarity NPC471355
0.877 High Similarity NPC77319
0.877 High Similarity NPC84987
0.877 High Similarity NPC473852
0.877 High Similarity NPC87250
0.877 High Similarity NPC27507
0.8699 High Similarity NPC83287
0.8689 High Similarity NPC193382
0.8689 High Similarity NPC72772
0.8689 High Similarity NPC99620
0.8689 High Similarity NPC469794
0.8689 High Similarity NPC199428
0.8689 High Similarity NPC310341
0.8689 High Similarity NPC5311
0.8647 High Similarity NPC79250
0.8647 High Similarity NPC290746
0.8629 High Similarity NPC5883
0.8629 High Similarity NPC44899
0.8629 High Similarity NPC304260
0.8629 High Similarity NPC29639
0.8626 High Similarity NPC248703
0.8618 High Similarity NPC152615
0.8618 High Similarity NPC474483
0.8615 High Similarity NPC155529
0.8607 High Similarity NPC471633
0.8607 High Similarity NPC69576
0.8607 High Similarity NPC84949
0.8607 High Similarity NPC31354
0.8583 High Similarity NPC318135
0.8561 High Similarity NPC158350
0.856 High Similarity NPC107607
0.855 High Similarity NPC476779
0.8548 High Similarity NPC218093
0.8538 High Similarity NPC477493
0.8527 High Similarity NPC477490
0.8527 High Similarity NPC114306
0.8527 High Similarity NPC245094
0.8516 High Similarity NPC47113
0.8516 High Similarity NPC174367
0.8496 Intermediate Similarity NPC477236
0.8492 Intermediate Similarity NPC170084
0.8492 Intermediate Similarity NPC476204
0.8485 Intermediate Similarity NPC476777
0.8485 Intermediate Similarity NPC476778
0.848 Intermediate Similarity NPC291820
0.848 Intermediate Similarity NPC81222
0.8473 Intermediate Similarity NPC477195
0.8473 Intermediate Similarity NPC471855
0.8468 Intermediate Similarity NPC290693
0.8468 Intermediate Similarity NPC203862
0.8462 Intermediate Similarity NPC476966
0.8462 Intermediate Similarity NPC231529
0.845 Intermediate Similarity NPC298841
0.845 Intermediate Similarity NPC42399
0.8425 Intermediate Similarity NPC28532
0.8421 Intermediate Similarity NPC279915
0.8421 Intermediate Similarity NPC110700
0.8413 Intermediate Similarity NPC472004
0.8413 Intermediate Similarity NPC135369
0.8413 Intermediate Similarity NPC281840
0.8409 Intermediate Similarity NPC316915
0.8409 Intermediate Similarity NPC475487
0.84 Intermediate Similarity NPC239293
0.84 Intermediate Similarity NPC469822
0.8397 Intermediate Similarity NPC300655
0.8397 Intermediate Similarity NPC311178
0.8397 Intermediate Similarity NPC222951
0.8397 Intermediate Similarity NPC43589
0.8387 Intermediate Similarity NPC196931
0.8387 Intermediate Similarity NPC137414
0.8385 Intermediate Similarity NPC23020
0.8385 Intermediate Similarity NPC472268
0.8385 Intermediate Similarity NPC470476
0.8385 Intermediate Similarity NPC472269
0.8385 Intermediate Similarity NPC470475
0.8385 Intermediate Similarity NPC472270
0.8385 Intermediate Similarity NPC112492
0.8374 Intermediate Similarity NPC102619
0.8359 Intermediate Similarity NPC41129
0.8346 Intermediate Similarity NPC475182
0.8346 Intermediate Similarity NPC477234
0.8333 Intermediate Similarity NPC183816
0.8333 Intermediate Similarity NPC475177
0.8333 Intermediate Similarity NPC478154

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC329636 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
0.9672 High Similarity NPD7319 Approved
0.9426 High Similarity NPD7507 Approved
0.9098 High Similarity NPD8378 Approved
0.9098 High Similarity NPD8335 Approved
0.9098 High Similarity NPD8296 Approved
0.9098 High Similarity NPD8380 Approved
0.9098 High Similarity NPD8379 Approved
0.9016 High Similarity NPD8377 Approved
0.9016 High Similarity NPD8294 Approved
0.879 High Similarity NPD8033 Approved
0.8699 High Similarity NPD7327 Approved
0.8699 High Similarity NPD7328 Approved
0.8629 High Similarity NPD7516 Approved
0.8374 Intermediate Similarity NPD8133 Approved
0.8244 Intermediate Similarity NPD7736 Approved
0.8077 Intermediate Similarity NPD8328 Phase 3
0.803 Intermediate Similarity NPD8293 Discontinued
0.7967 Intermediate Similarity NPD6686 Approved
0.7923 Intermediate Similarity NPD7503 Approved
0.7863 Intermediate Similarity NPD6370 Approved
0.7786 Intermediate Similarity NPD8517 Approved
0.7786 Intermediate Similarity NPD8513 Phase 3
0.7786 Intermediate Similarity NPD8515 Approved
0.7786 Intermediate Similarity NPD8516 Approved
0.7752 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD7492 Approved
0.7742 Intermediate Similarity NPD6412 Phase 2
0.771 Intermediate Similarity NPD6059 Approved
0.771 Intermediate Similarity NPD6054 Approved
0.7687 Intermediate Similarity NPD6616 Approved
0.763 Intermediate Similarity NPD7078 Approved
0.7581 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD6319 Approved
0.7519 Intermediate Similarity NPD6015 Approved
0.7519 Intermediate Similarity NPD6016 Approved
0.7463 Intermediate Similarity NPD5988 Approved
0.7459 Intermediate Similarity NPD7638 Approved
0.7442 Intermediate Similarity NPD6882 Approved
0.7442 Intermediate Similarity NPD8297 Approved
0.7398 Intermediate Similarity NPD7640 Approved
0.7398 Intermediate Similarity NPD7639 Approved
0.7348 Intermediate Similarity NPD7115 Discovery
0.7348 Intermediate Similarity NPD6009 Approved
0.7344 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD7320 Approved
0.7252 Intermediate Similarity NPD4632 Approved
0.7244 Intermediate Similarity NPD6402 Approved
0.7244 Intermediate Similarity NPD5739 Approved
0.7244 Intermediate Similarity NPD6675 Approved
0.7244 Intermediate Similarity NPD7128 Approved
0.7209 Intermediate Similarity NPD6372 Approved
0.7209 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD6373 Approved
0.7194 Intermediate Similarity NPD6033 Approved
0.7181 Intermediate Similarity NPD7625 Phase 1
0.7132 Intermediate Similarity NPD6881 Approved
0.7132 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD6899 Approved
0.7099 Intermediate Similarity NPD6650 Approved
0.7099 Intermediate Similarity NPD8130 Phase 1
0.7099 Intermediate Similarity NPD6649 Approved
0.7054 Intermediate Similarity NPD5697 Approved
0.7054 Intermediate Similarity NPD5701 Approved
0.7045 Intermediate Similarity NPD6053 Discontinued
0.7023 Intermediate Similarity NPD6883 Approved
0.7023 Intermediate Similarity NPD4634 Approved
0.7023 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD7290 Approved
0.7023 Intermediate Similarity NPD7102 Approved
0.6977 Remote Similarity NPD6008 Approved
0.697 Remote Similarity NPD6847 Approved
0.697 Remote Similarity NPD6869 Approved
0.697 Remote Similarity NPD6617 Approved
0.697 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6947 Remote Similarity NPD6014 Approved
0.6947 Remote Similarity NPD6012 Approved
0.6947 Remote Similarity NPD6013 Approved
0.6911 Remote Similarity NPD8171 Discontinued
0.6906 Remote Similarity NPD6067 Discontinued
0.6906 Remote Similarity NPD7604 Phase 2
0.6884 Remote Similarity NPD5983 Phase 2
0.6879 Remote Similarity NPD8074 Phase 3
0.6875 Remote Similarity NPD7632 Discontinued
0.687 Remote Similarity NPD6011 Approved
0.6842 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6825 Remote Similarity NPD4755 Approved
0.6809 Remote Similarity NPD6336 Discontinued
0.6807 Remote Similarity NPD7799 Discontinued
0.6794 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6794 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6772 Remote Similarity NPD4225 Approved
0.6744 Remote Similarity NPD5211 Phase 2
0.672 Remote Similarity NPD7748 Approved
0.6719 Remote Similarity NPD5285 Approved
0.6719 Remote Similarity NPD4696 Approved
0.6719 Remote Similarity NPD4700 Approved
0.6719 Remote Similarity NPD5286 Approved
0.6693 Remote Similarity NPD6083 Phase 2
0.6693 Remote Similarity NPD6084 Phase 2
0.6693 Remote Similarity NPD7902 Approved
0.6643 Remote Similarity NPD6921 Approved
0.6642 Remote Similarity NPD6371 Approved
0.6642 Remote Similarity NPD6274 Approved
0.6641 Remote Similarity NPD5141 Approved
0.6621 Remote Similarity NPD8390 Approved
0.6621 Remote Similarity NPD8392 Approved
0.6621 Remote Similarity NPD8391 Approved
0.6619 Remote Similarity NPD7100 Approved
0.6619 Remote Similarity NPD7101 Approved
0.6615 Remote Similarity NPD5224 Approved
0.6615 Remote Similarity NPD5225 Approved
0.6615 Remote Similarity NPD5226 Approved
0.6615 Remote Similarity NPD4633 Approved
0.6597 Remote Similarity NPD8336 Approved
0.6597 Remote Similarity NPD8337 Approved
0.6591 Remote Similarity NPD4767 Approved
0.6591 Remote Similarity NPD4768 Approved
0.6573 Remote Similarity NPD8451 Approved
0.6565 Remote Similarity NPD5175 Approved
0.6565 Remote Similarity NPD5174 Approved
0.656 Remote Similarity NPD8034 Phase 2
0.656 Remote Similarity NPD8035 Phase 2
0.656 Remote Similarity NPD7515 Phase 2
0.6547 Remote Similarity NPD6335 Approved
0.6538 Remote Similarity NPD5223 Approved
0.6532 Remote Similarity NPD5328 Approved
0.6531 Remote Similarity NPD8338 Approved
0.6528 Remote Similarity NPD8448 Approved
0.6525 Remote Similarity NPD6909 Approved
0.6525 Remote Similarity NPD6908 Approved
0.6508 Remote Similarity NPD4202 Approved
0.6507 Remote Similarity NPD5956 Approved
0.6493 Remote Similarity NPD4729 Approved
0.6493 Remote Similarity NPD4730 Approved
0.6484 Remote Similarity NPD4697 Phase 3
0.648 Remote Similarity NPD6698 Approved
0.648 Remote Similarity NPD46 Approved
0.6475 Remote Similarity NPD6317 Approved
0.6457 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6457 Remote Similarity NPD7900 Approved
0.6452 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6439 Remote Similarity NPD4754 Approved
0.6434 Remote Similarity NPD7829 Approved
0.6434 Remote Similarity NPD7830 Approved
0.6429 Remote Similarity NPD6079 Approved
0.6429 Remote Similarity NPD6313 Approved
0.6429 Remote Similarity NPD6314 Approved
0.6419 Remote Similarity NPD8449 Approved
0.6408 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6406 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6406 Remote Similarity NPD5695 Phase 3
0.6397 Remote Similarity NPD5251 Approved
0.6397 Remote Similarity NPD5248 Approved
0.6397 Remote Similarity NPD5247 Approved
0.6397 Remote Similarity NPD5249 Phase 3
0.6397 Remote Similarity NPD5250 Approved
0.6389 Remote Similarity NPD8340 Approved
0.6389 Remote Similarity NPD8342 Approved
0.6389 Remote Similarity NPD8341 Approved
0.6389 Remote Similarity NPD8299 Approved
0.6385 Remote Similarity NPD5696 Approved
0.6385 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6378 Remote Similarity NPD6399 Phase 3
0.6376 Remote Similarity NPD8450 Suspended
0.637 Remote Similarity NPD5128 Approved
0.6341 Remote Similarity NPD7520 Clinical (unspecified phase)
0.632 Remote Similarity NPD6903 Approved
0.6319 Remote Similarity NPD7642 Approved
0.6316 Remote Similarity NPD6333 Approved
0.6316 Remote Similarity NPD6334 Approved
0.6299 Remote Similarity NPD7637 Suspended
0.6299 Remote Similarity NPD5693 Phase 1
0.6299 Remote Similarity NPD7983 Approved
0.629 Remote Similarity NPD6409 Approved
0.629 Remote Similarity NPD5330 Approved
0.629 Remote Similarity NPD6684 Approved
0.629 Remote Similarity NPD7521 Approved
0.629 Remote Similarity NPD7334 Approved
0.629 Remote Similarity NPD7146 Approved
0.6288 Remote Similarity NPD5344 Discontinued
0.627 Remote Similarity NPD4753 Phase 2
0.625 Remote Similarity NPD7966 Clinical (unspecified phase)
0.625 Remote Similarity NPD8080 Discontinued
0.6242 Remote Similarity NPD7260 Phase 2
0.6241 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6232 Remote Similarity NPD5215 Approved
0.6232 Remote Similarity NPD5216 Approved
0.6232 Remote Similarity NPD5217 Approved
0.6231 Remote Similarity NPD5221 Approved
0.6231 Remote Similarity NPD5222 Approved
0.6231 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6183 Remote Similarity NPD5173 Approved
0.6172 Remote Similarity NPD6411 Approved
0.617 Remote Similarity NPD6868 Approved
0.616 Remote Similarity NPD3618 Phase 1
0.6159 Remote Similarity NPD5169 Approved
0.6159 Remote Similarity NPD5135 Approved
0.6159 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6145 Remote Similarity NPD5761 Phase 2
0.6145 Remote Similarity NPD5760 Phase 2

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data