Structure

Physi-Chem Properties

Molecular Weight:  984.49
Volume:  946.947
LogP:  1.872
LogD:  1.824
LogS:  -3.587
# Rotatable Bonds:  13
TPSA:  284.35
# H-Bond Aceptor:  20
# H-Bond Donor:  8
# Rings:  9
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.103
Synthetic Accessibility Score:  6.768
Fsp3:  0.898
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.421
MDCK Permeability:  0.00022867319057695568
Pgp-inhibitor:  0.0
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.775
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.335

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.18
Plasma Protein Binding (PPB):  45.321022033691406%
Volume Distribution (VD):  0.218
Pgp-substrate:  19.491567611694336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.987
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.12
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.002
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.035
CYP3A4-inhibitor:  0.324
CYP3A4-substrate:  0.799

ADMET: Excretion

Clearance (CL):  0.516
Half-life (T1/2):  0.463

ADMET: Toxicity

hERG Blockers:  0.591
Human Hepatotoxicity (H-HT):  0.201
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.333
Rat Oral Acute Toxicity:  0.908
Maximum Recommended Daily Dose:  0.981
Skin Sensitization:  0.922
Carcinogencity:  0.765
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.976

Download Data

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

  Natural Product: NPC329675

Natural Product ID:  NPC329675
Common Name*:   Madagascarensilide D
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)-4-methoxy-5-[(2S,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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 D
Standard InCHIKey:  FNMTWOGECNNJOI-ASYHMFTESA-N
Standard InCHI:  InChI=1S/C49H76O20/c1-23-42(67-37-17-32(59-5)43(24(2)63-37)68-38-18-33(60-6)44(25(3)64-38)69-45-41(56)40(55)39(54)34(20-50)66-45)31(52)16-36(62-23)65-27-7-12-47(22-51)29-8-11-46(4)28(26-15-35(53)61-21-26)10-14-49(46,58)30(29)9-13-48(47,57)19-27/h15,22-25,27-34,36-45,50,52,54-58H,7-14,16-21H2,1-6H3/t23-,24-,25-,27+,28-,29+,30-,31+,32+,33-,34-,36+,37+,38+,39-,40+,41-,42-,43-,44+,45+,46-,47+,48+,49+/m1/s1
SMILES:  CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1644524
PubChem CID:   53322208
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 = 290.0 nM PMID[558504]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 480.0 nM PMID[558504]

☑ 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 NPC329675 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
0.9839 High Similarity NPC329636
0.9758 High Similarity NPC116075
0.9758 High Similarity NPC247190
0.9758 High Similarity NPC32793
0.9758 High Similarity NPC146857
0.9758 High Similarity NPC469749
0.9683 High Similarity NPC59288
0.9516 High Similarity NPC471352
0.9516 High Similarity NPC70542
0.9516 High Similarity NPC17896
0.9516 High Similarity NPC6108
0.9516 High Similarity NPC140092
0.9516 High Similarity NPC232785
0.9516 High Similarity NPC469754
0.9516 High Similarity NPC188234
0.9516 High Similarity NPC471360
0.9516 High Similarity NPC469755
0.9516 High Similarity NPC471359
0.9516 High Similarity NPC469753
0.9516 High Similarity NPC276838
0.9516 High Similarity NPC180079
0.9516 High Similarity NPC469751
0.9516 High Similarity NPC89514
0.9516 High Similarity NPC86159
0.9516 High Similarity NPC197707
0.9516 High Similarity NPC471358
0.9516 High Similarity NPC125077
0.9516 High Similarity NPC284406
0.9516 High Similarity NPC471361
0.9516 High Similarity NPC469752
0.9516 High Similarity NPC10823
0.9516 High Similarity NPC219085
0.9516 High Similarity NPC9499
0.9516 High Similarity NPC251866
0.9516 High Similarity NPC329986
0.9444 High Similarity NPC477709
0.9444 High Similarity NPC476221
0.9365 High Similarity NPC93416
0.9355 High Similarity NPC469757
0.9355 High Similarity NPC471357
0.9355 High Similarity NPC117702
0.9355 High Similarity NPC329784
0.9355 High Similarity NPC146456
0.9355 High Similarity NPC240070
0.9355 High Similarity NPC179412
0.9355 High Similarity NPC471356
0.9286 High Similarity NPC16569
0.9286 High Similarity NPC159338
0.9286 High Similarity NPC253456
0.9274 High Similarity NPC250556
0.9274 High Similarity NPC469750
0.9213 High Similarity NPC42670
0.9213 High Similarity NPC19124
0.9206 High Similarity NPC91
0.9141 High Similarity NPC104585
0.9141 High Similarity NPC157817
0.9141 High Similarity NPC142756
0.9141 High Similarity NPC225385
0.9141 High Similarity NPC298783
0.9113 High Similarity NPC27363
0.9113 High Similarity NPC208193
0.9113 High Similarity NPC308262
0.9113 High Similarity NPC117445
0.9032 High Similarity NPC474423
0.9032 High Similarity NPC74259
0.9 High Similarity NPC171619
0.8976 High Similarity NPC311534
0.8952 High Similarity NPC314535
0.8952 High Similarity NPC173555
0.8952 High Similarity NPC474908
0.8952 High Similarity NPC475590
0.8952 High Similarity NPC475419
0.8952 High Similarity NPC120390
0.8931 High Similarity NPC289700
0.8931 High Similarity NPC62172
0.888 High Similarity NPC264336
0.8871 High Similarity NPC72260
0.8871 High Similarity NPC475556
0.8871 High Similarity NPC475629
0.8846 High Similarity NPC88668
0.8837 High Similarity NPC173347
0.8797 High Similarity NPC290746
0.8797 High Similarity NPC79250
0.8797 High Similarity NPC75616
0.879 High Similarity NPC469756
0.879 High Similarity NPC30483
0.879 High Similarity NPC236973
0.879 High Similarity NPC32177
0.879 High Similarity NPC292467
0.879 High Similarity NPC55532
0.879 High Similarity NPC470897
0.8788 High Similarity NPC127656
0.873 High Similarity NPC193893
0.872 High Similarity NPC476150
0.872 High Similarity NPC470312
0.872 High Similarity NPC474466
0.872 High Similarity NPC476127
0.872 High Similarity NPC475136
0.8702 High Similarity NPC476779
0.8651 High Similarity NPC231518
0.8651 High Similarity NPC475219
0.8651 High Similarity NPC40749
0.8647 High Similarity NPC477236
0.864 High Similarity NPC329905
0.8636 High Similarity NPC476777
0.8636 High Similarity NPC476778
0.8629 High Similarity NPC87250
0.8629 High Similarity NPC27507
0.8629 High Similarity NPC84987
0.8629 High Similarity NPC309034
0.8629 High Similarity NPC471354
0.8629 High Similarity NPC244402
0.8629 High Similarity NPC196429
0.8629 High Similarity NPC77319
0.8629 High Similarity NPC142066
0.8629 High Similarity NPC474418
0.8629 High Similarity NPC34390
0.8629 High Similarity NPC158344
0.8629 High Similarity NPC93883
0.8629 High Similarity NPC471351
0.8629 High Similarity NPC157376
0.8629 High Similarity NPC99728
0.8629 High Similarity NPC50305
0.8629 High Similarity NPC471353
0.8629 High Similarity NPC471355
0.8629 High Similarity NPC473852
0.8629 High Similarity NPC243196
0.8571 High Similarity NPC110700
0.8571 High Similarity NPC135369
0.8571 High Similarity NPC279915
0.856 High Similarity NPC83287
0.855 High Similarity NPC43589
0.855 High Similarity NPC300655
0.855 High Similarity NPC222951
0.855 High Similarity NPC311178
0.855 High Similarity NPC477493
0.8548 High Similarity NPC193382
0.8548 High Similarity NPC99620
0.8548 High Similarity NPC5311
0.8548 High Similarity NPC72772
0.8548 High Similarity NPC199428
0.8548 High Similarity NPC310341
0.8548 High Similarity NPC469794
0.8538 High Similarity NPC23020
0.8538 High Similarity NPC472269
0.8538 High Similarity NPC472268
0.8538 High Similarity NPC470475
0.8538 High Similarity NPC112492
0.8538 High Similarity NPC470476
0.8538 High Similarity NPC472270
0.8504 High Similarity NPC475182
0.8496 Intermediate Similarity NPC477234
0.8496 Intermediate Similarity NPC248703
0.8492 Intermediate Similarity NPC29639
0.8492 Intermediate Similarity NPC5883
0.8492 Intermediate Similarity NPC44899
0.8492 Intermediate Similarity NPC304260
0.8485 Intermediate Similarity NPC322904
0.8485 Intermediate Similarity NPC324933
0.8485 Intermediate Similarity NPC475177
0.8485 Intermediate Similarity NPC233223
0.8485 Intermediate Similarity NPC473679
0.8485 Intermediate Similarity NPC183816
0.8485 Intermediate Similarity NPC196874
0.8485 Intermediate Similarity NPC155529
0.8485 Intermediate Similarity NPC475444
0.8485 Intermediate Similarity NPC476776
0.8485 Intermediate Similarity NPC477195
0.8485 Intermediate Similarity NPC319719
0.848 Intermediate Similarity NPC152615
0.848 Intermediate Similarity NPC474483
0.8473 Intermediate Similarity NPC47995
0.8473 Intermediate Similarity NPC477235
0.8473 Intermediate Similarity NPC265841
0.8468 Intermediate Similarity NPC84949
0.8468 Intermediate Similarity NPC69576
0.8468 Intermediate Similarity NPC31354
0.8468 Intermediate Similarity NPC471633
0.8462 Intermediate Similarity NPC470516
0.845 Intermediate Similarity NPC318135
0.845 Intermediate Similarity NPC248202
0.845 Intermediate Similarity NPC473505
0.8433 Intermediate Similarity NPC158350
0.8425 Intermediate Similarity NPC107607
0.8425 Intermediate Similarity NPC108072
0.8421 Intermediate Similarity NPC475487
0.8413 Intermediate Similarity NPC218093
0.8413 Intermediate Similarity NPC473459
0.8413 Intermediate Similarity NPC469822
0.8409 Intermediate Similarity NPC476780
0.8409 Intermediate Similarity NPC476775
0.8409 Intermediate Similarity NPC476774
0.8409 Intermediate Similarity NPC271610
0.84 Intermediate Similarity NPC137414
0.8397 Intermediate Similarity NPC220838
0.8397 Intermediate Similarity NPC245094
0.8397 Intermediate Similarity NPC114306
0.8397 Intermediate Similarity NPC477490
0.8397 Intermediate Similarity NPC45606

  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 NPC329675 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
0.9516 High Similarity NPD7319 Approved
0.9274 High Similarity NPD7507 Approved
0.8952 High Similarity NPD8296 Approved
0.8952 High Similarity NPD8335 Approved
0.8952 High Similarity NPD8378 Approved
0.8952 High Similarity NPD8380 Approved
0.8952 High Similarity NPD8379 Approved
0.8871 High Similarity NPD8377 Approved
0.8871 High Similarity NPD8294 Approved
0.8651 High Similarity NPD8033 Approved
0.856 High Similarity NPD7328 Approved
0.856 High Similarity NPD7327 Approved
0.8492 Intermediate Similarity NPD7516 Approved
0.8387 Intermediate Similarity NPD8133 Approved
0.812 Intermediate Similarity NPD7736 Approved
0.8092 Intermediate Similarity NPD8328 Phase 3
0.791 Intermediate Similarity NPD8293 Discontinued
0.784 Intermediate Similarity NPD6686 Approved
0.7803 Intermediate Similarity NPD8517 Approved
0.7803 Intermediate Similarity NPD8515 Approved
0.7803 Intermediate Similarity NPD8516 Approved
0.7803 Intermediate Similarity NPD7503 Approved
0.7744 Intermediate Similarity NPD6370 Approved
0.7669 Intermediate Similarity NPD8513 Phase 3
0.7634 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD7492 Approved
0.7619 Intermediate Similarity NPD6412 Phase 2
0.7594 Intermediate Similarity NPD6059 Approved
0.7594 Intermediate Similarity NPD6054 Approved
0.7574 Intermediate Similarity NPD6616 Approved
0.7518 Intermediate Similarity NPD7078 Approved
0.7463 Intermediate Similarity NPD6319 Approved
0.746 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6016 Approved
0.7407 Intermediate Similarity NPD6015 Approved
0.7353 Intermediate Similarity NPD5988 Approved
0.7339 Intermediate Similarity NPD7638 Approved
0.7328 Intermediate Similarity NPD6882 Approved
0.7328 Intermediate Similarity NPD8297 Approved
0.728 Intermediate Similarity NPD7640 Approved
0.728 Intermediate Similarity NPD7639 Approved
0.7239 Intermediate Similarity NPD6009 Approved
0.7239 Intermediate Similarity NPD7115 Discovery
0.7231 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD7320 Approved
0.7143 Intermediate Similarity NPD4632 Approved
0.7132 Intermediate Similarity NPD5739 Approved
0.7132 Intermediate Similarity NPD6402 Approved
0.7132 Intermediate Similarity NPD7128 Approved
0.7132 Intermediate Similarity NPD6675 Approved
0.7099 Intermediate Similarity NPD6373 Approved
0.7099 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD6372 Approved
0.7092 Intermediate Similarity NPD6033 Approved
0.7086 Intermediate Similarity NPD7625 Phase 1
0.7023 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD6899 Approved
0.7023 Intermediate Similarity NPD6881 Approved
0.6992 Remote Similarity NPD6650 Approved
0.6992 Remote Similarity NPD6649 Approved
0.6992 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6992 Remote Similarity NPD8130 Phase 1
0.6947 Remote Similarity NPD5701 Approved
0.6947 Remote Similarity NPD5697 Approved
0.694 Remote Similarity NPD6053 Discontinued
0.6917 Remote Similarity NPD6883 Approved
0.6917 Remote Similarity NPD7290 Approved
0.6917 Remote Similarity NPD7102 Approved
0.6917 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6917 Remote Similarity NPD4634 Approved
0.687 Remote Similarity NPD6008 Approved
0.6866 Remote Similarity NPD6847 Approved
0.6866 Remote Similarity NPD6869 Approved
0.6866 Remote Similarity NPD6617 Approved
0.6842 Remote Similarity NPD6014 Approved
0.6842 Remote Similarity NPD6013 Approved
0.6842 Remote Similarity NPD6012 Approved
0.6809 Remote Similarity NPD6067 Discontinued
0.6809 Remote Similarity NPD7604 Phase 2
0.68 Remote Similarity NPD8171 Discontinued
0.6786 Remote Similarity NPD5983 Phase 2
0.6783 Remote Similarity NPD8074 Phase 3
0.6769 Remote Similarity NPD7632 Discontinued
0.6767 Remote Similarity NPD6011 Approved
0.6741 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6726 Remote Similarity NPD7799 Discontinued
0.6719 Remote Similarity NPD4755 Approved
0.6713 Remote Similarity NPD6336 Discontinued
0.6692 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6692 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4225 Approved
0.6641 Remote Similarity NPD5211 Phase 2
0.6615 Remote Similarity NPD5285 Approved
0.6615 Remote Similarity NPD4700 Approved
0.6615 Remote Similarity NPD5286 Approved
0.6615 Remote Similarity NPD4696 Approved
0.6614 Remote Similarity NPD7748 Approved
0.6589 Remote Similarity NPD6084 Phase 2
0.6589 Remote Similarity NPD6083 Phase 2
0.6589 Remote Similarity NPD7902 Approved
0.6552 Remote Similarity NPD8448 Approved
0.6549 Remote Similarity NPD6921 Approved
0.6547 Remote Similarity NPD6274 Approved
0.6544 Remote Similarity NPD6371 Approved
0.6541 Remote Similarity NPD5141 Approved
0.6531 Remote Similarity NPD8392 Approved
0.6531 Remote Similarity NPD8391 Approved
0.6531 Remote Similarity NPD8390 Approved
0.6525 Remote Similarity NPD7100 Approved
0.6525 Remote Similarity NPD7101 Approved
0.6515 Remote Similarity NPD5225 Approved
0.6515 Remote Similarity NPD5226 Approved
0.6515 Remote Similarity NPD4633 Approved
0.6515 Remote Similarity NPD5224 Approved
0.651 Remote Similarity NPD8450 Suspended
0.6507 Remote Similarity NPD8337 Approved
0.6507 Remote Similarity NPD8336 Approved
0.6493 Remote Similarity NPD4767 Approved
0.6493 Remote Similarity NPD4768 Approved
0.6483 Remote Similarity NPD8451 Approved
0.6466 Remote Similarity NPD5174 Approved
0.6466 Remote Similarity NPD5175 Approved
0.6457 Remote Similarity NPD8035 Phase 2
0.6457 Remote Similarity NPD7515 Phase 2
0.6457 Remote Similarity NPD8034 Phase 2
0.6454 Remote Similarity NPD6335 Approved
0.6443 Remote Similarity NPD8338 Approved
0.6443 Remote Similarity NPD8449 Approved
0.6439 Remote Similarity NPD5223 Approved
0.6434 Remote Similarity NPD6909 Approved
0.6434 Remote Similarity NPD6908 Approved
0.6429 Remote Similarity NPD5328 Approved
0.6419 Remote Similarity NPD5956 Approved
0.6406 Remote Similarity NPD4202 Approved
0.6397 Remote Similarity NPD4729 Approved
0.6397 Remote Similarity NPD4730 Approved
0.6385 Remote Similarity NPD4697 Phase 3
0.6383 Remote Similarity NPD6317 Approved
0.6378 Remote Similarity NPD6698 Approved
0.6378 Remote Similarity NPD46 Approved
0.6357 Remote Similarity NPD7900 Approved
0.6357 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6349 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6345 Remote Similarity NPD7830 Approved
0.6345 Remote Similarity NPD7829 Approved
0.6343 Remote Similarity NPD4754 Approved
0.6338 Remote Similarity NPD6313 Approved
0.6338 Remote Similarity NPD6314 Approved
0.6328 Remote Similarity NPD6079 Approved
0.6319 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6308 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6308 Remote Similarity NPD5695 Phase 3
0.6304 Remote Similarity NPD5251 Approved
0.6304 Remote Similarity NPD5250 Approved
0.6304 Remote Similarity NPD5247 Approved
0.6304 Remote Similarity NPD5248 Approved
0.6304 Remote Similarity NPD5249 Phase 3
0.6301 Remote Similarity NPD8341 Approved
0.6301 Remote Similarity NPD8340 Approved
0.6301 Remote Similarity NPD8299 Approved
0.6301 Remote Similarity NPD8342 Approved
0.6288 Remote Similarity NPD5696 Approved
0.6288 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6279 Remote Similarity NPD6399 Phase 3
0.6277 Remote Similarity NPD5128 Approved
0.624 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6234 Remote Similarity NPD6334 Approved
0.6234 Remote Similarity NPD6333 Approved
0.6233 Remote Similarity NPD7642 Approved
0.622 Remote Similarity NPD6903 Approved
0.6202 Remote Similarity NPD5693 Phase 1
0.6202 Remote Similarity NPD7637 Suspended
0.6202 Remote Similarity NPD7983 Approved
0.6194 Remote Similarity NPD5344 Discontinued
0.619 Remote Similarity NPD5330 Approved
0.619 Remote Similarity NPD7334 Approved
0.619 Remote Similarity NPD6409 Approved
0.619 Remote Similarity NPD7146 Approved
0.619 Remote Similarity NPD6684 Approved
0.619 Remote Similarity NPD7521 Approved
0.6172 Remote Similarity NPD4753 Phase 2
0.6169 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6164 Remote Similarity NPD8080 Discontinued
0.6159 Remote Similarity NPD7260 Phase 2
0.6154 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6143 Remote Similarity NPD5215 Approved
0.6143 Remote Similarity NPD5216 Approved
0.6143 Remote Similarity NPD5217 Approved
0.6136 Remote Similarity NPD5222 Approved
0.6136 Remote Similarity NPD5221 Approved
0.6136 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6096 Remote Similarity NPD8444 Approved
0.609 Remote Similarity NPD5173 Approved
0.6084 Remote Similarity NPD6868 Approved
0.6077 Remote Similarity NPD6411 Approved
0.6071 Remote Similarity NPD5761 Phase 2
0.6071 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5169 Approved
0.6071 Remote Similarity NPD5135 Approved
0.6071 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