Structure

Physi-Chem Properties

Molecular Weight:  573.37
Volume:  586.684
LogP:  3.606
LogD:  3.548
LogS:  -3.773
# Rotatable Bonds:  3
TPSA:  120.64
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  7
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.327
Synthetic Accessibility Score:  5.926
Fsp3:  0.879
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.512
MDCK Permeability:  1.3039503755862825e-05
Pgp-inhibitor:  0.479
Pgp-substrate:  0.908
Human Intestinal Absorption (HIA):  0.945
20% Bioavailability (F20%):  0.879
30% Bioavailability (F30%):  0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.014
Plasma Protein Binding (PPB):  86.76140594482422%
Volume Distribution (VD):  0.953
Pgp-substrate:  6.46656608581543%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.198
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.853
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.764
CYP3A4-inhibitor:  0.406
CYP3A4-substrate:  0.393

ADMET: Excretion

Clearance (CL):  2.246
Half-life (T1/2):  0.524

ADMET: Toxicity

hERG Blockers:  0.78
Human Hepatotoxicity (H-HT):  0.265
Drug-inuced Liver Injury (DILI):  0.16
AMES Toxicity:  0.27
Rat Oral Acute Toxicity:  0.544
Maximum Recommended Daily Dose:  0.906
Skin Sensitization:  0.297
Carcinogencity:  0.611
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.964

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

  Natural Product: NPC297058

Natural Product ID:  NPC297058
Common Name*:   Cycloposine
IUPAC Name:   (2R,3R,4S,5S,6R)-2-[(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   Cycloposine
Standard InCHIKey:  OSOOWXRUSUHLOX-PBFVMIKGSA-N
Standard InCHI:  InChI=1S/C33H51NO7/c1-16-11-25-27(34-14-16)18(3)33(41-25)10-8-21-22-6-5-19-12-20(7-9-32(19,4)24(22)13-23(21)17(33)2)39-31-30(38)29(37)28(36)26(15-35)40-31/h5,16,18,20-22,24-31,34-38H,6-15H2,1-4H3/t16-,18+,20-,21-,22-,24-,25+,26+,27-,28+,29-,30+,31+,32-,33-/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC3=C(C)[C@]5(CC[C@@H]43)O[C@H]3[C@H]([C@H]5C)NC[C@H](C3)C)C2)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1241233
PubChem CID:   25078000
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides
          • [CHEMONTID:0002364] Steroidal saponins

*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
NPO1073 Phlomis samia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[11520237]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. bark n.a. PMID[15283458]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. stem n.a. PMID[15577257]
NPO4250 Gloriosa superba Species Colchicaceae Eukaryota n.a. n.a. n.a. PMID[32372642]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9051910]
NPO4250 Gloriosa superba Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4250 Gloriosa superba Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4250 Gloriosa superba Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9596 Baeria coronaria n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO1073 Phlomis samia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11380 Neurolaena macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12742 Botryotrichum peruvianum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14649 Thais orbita Species Muricidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12144 Fontanesia phillyreoides Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5237 Stevia isomeca Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13582 Leucopaxillus giganteus Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ 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
NPT2 Others Unspecified EC50 > 700.0 nM PMID[519003]

☑ 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 NPC297058 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
0.874 High Similarity NPC296686
0.8548 High Similarity NPC28280
0.8548 High Similarity NPC304646
0.8485 Intermediate Similarity NPC15249
0.8485 Intermediate Similarity NPC25455
0.8421 Intermediate Similarity NPC122819
0.8358 Intermediate Similarity NPC150057
0.8358 Intermediate Similarity NPC147753
0.8295 Intermediate Similarity NPC478138
0.8116 Intermediate Similarity NPC287885
0.8106 Intermediate Similarity NPC265275
0.8106 Intermediate Similarity NPC94881
0.8106 Intermediate Similarity NPC48886
0.791 Intermediate Similarity NPC317654
0.791 Intermediate Similarity NPC96010
0.7879 Intermediate Similarity NPC469943
0.7721 Intermediate Similarity NPC478136
0.7638 Intermediate Similarity NPC14630
0.7638 Intermediate Similarity NPC157530
0.7638 Intermediate Similarity NPC250089
0.7609 Intermediate Similarity NPC478139
0.7519 Intermediate Similarity NPC13190
0.748 Intermediate Similarity NPC33053
0.7462 Intermediate Similarity NPC112274
0.7462 Intermediate Similarity NPC314306
0.746 Intermediate Similarity NPC93352
0.7447 Intermediate Similarity NPC477072
0.7442 Intermediate Similarity NPC170974
0.7442 Intermediate Similarity NPC191439
0.7442 Intermediate Similarity NPC103627
0.7405 Intermediate Similarity NPC51154
0.7405 Intermediate Similarity NPC478137
0.7385 Intermediate Similarity NPC208189
0.7385 Intermediate Similarity NPC472987
0.7385 Intermediate Similarity NPC473021
0.7385 Intermediate Similarity NPC65034
0.7364 Intermediate Similarity NPC473328
0.7364 Intermediate Similarity NPC28844
0.7364 Intermediate Similarity NPC473318
0.7357 Intermediate Similarity NPC201359
0.7348 Intermediate Similarity NPC11548
0.7328 Intermediate Similarity NPC231797
0.7328 Intermediate Similarity NPC42171
0.7323 Intermediate Similarity NPC470885
0.7323 Intermediate Similarity NPC187400
0.7323 Intermediate Similarity NPC221562
0.731 Intermediate Similarity NPC180770
0.731 Intermediate Similarity NPC302276
0.7308 Intermediate Similarity NPC141433
0.7308 Intermediate Similarity NPC65155
0.7293 Intermediate Similarity NPC477029
0.7293 Intermediate Similarity NPC477030
0.7287 Intermediate Similarity NPC476540
0.7287 Intermediate Similarity NPC476541
0.7287 Intermediate Similarity NPC476539
0.7287 Intermediate Similarity NPC476538
0.7273 Intermediate Similarity NPC469348
0.7273 Intermediate Similarity NPC469347
0.7266 Intermediate Similarity NPC181845
0.7266 Intermediate Similarity NPC309448
0.7252 Intermediate Similarity NPC197231
0.7239 Intermediate Similarity NPC20979
0.7239 Intermediate Similarity NPC100048
0.7239 Intermediate Similarity NPC476690
0.7231 Intermediate Similarity NPC42482
0.7231 Intermediate Similarity NPC472901
0.7231 Intermediate Similarity NPC253645
0.7231 Intermediate Similarity NPC40440
0.7231 Intermediate Similarity NPC147835
0.7231 Intermediate Similarity NPC477027
0.7231 Intermediate Similarity NPC85001
0.7231 Intermediate Similarity NPC306131
0.7231 Intermediate Similarity NPC477026
0.7231 Intermediate Similarity NPC70204
0.7231 Intermediate Similarity NPC475670
0.7231 Intermediate Similarity NPC95920
0.7226 Intermediate Similarity NPC20035
0.7222 Intermediate Similarity NPC285231
0.7222 Intermediate Similarity NPC470434
0.7222 Intermediate Similarity NPC21568
0.7219 Intermediate Similarity NPC36463
0.7219 Intermediate Similarity NPC298005
0.7211 Intermediate Similarity NPC162910
0.7209 Intermediate Similarity NPC231340
0.7209 Intermediate Similarity NPC230507
0.7209 Intermediate Similarity NPC190395
0.7209 Intermediate Similarity NPC14704
0.7209 Intermediate Similarity NPC470432
0.7209 Intermediate Similarity NPC305423
0.7209 Intermediate Similarity NPC283829
0.7209 Intermediate Similarity NPC113044
0.7209 Intermediate Similarity NPC161676
0.7209 Intermediate Similarity NPC226642
0.72 Intermediate Similarity NPC61717
0.72 Intermediate Similarity NPC244380
0.7197 Intermediate Similarity NPC19888
0.7188 Intermediate Similarity NPC75608
0.7185 Intermediate Similarity NPC475403
0.7185 Intermediate Similarity NPC10366
0.7185 Intermediate Similarity NPC160888
0.7183 Intermediate Similarity NPC139585
0.7165 Intermediate Similarity NPC272015
0.7165 Intermediate Similarity NPC176012
0.7164 Intermediate Similarity NPC148965
0.7154 Intermediate Similarity NPC220427
0.7154 Intermediate Similarity NPC472897
0.7154 Intermediate Similarity NPC98696
0.7154 Intermediate Similarity NPC472896
0.7143 Intermediate Similarity NPC469942
0.7143 Intermediate Similarity NPC282669
0.7133 Intermediate Similarity NPC262050
0.7132 Intermediate Similarity NPC472898
0.7132 Intermediate Similarity NPC195560
0.7132 Intermediate Similarity NPC242748
0.7132 Intermediate Similarity NPC472900
0.7132 Intermediate Similarity NPC473476
0.7132 Intermediate Similarity NPC473633
0.7132 Intermediate Similarity NPC476085
0.7132 Intermediate Similarity NPC473923
0.7132 Intermediate Similarity NPC472899
0.7132 Intermediate Similarity NPC474569
0.7132 Intermediate Similarity NPC229962
0.7125 Intermediate Similarity NPC473040
0.7121 Intermediate Similarity NPC475247
0.7121 Intermediate Similarity NPC124677
0.7121 Intermediate Similarity NPC477028
0.7121 Intermediate Similarity NPC477032
0.7121 Intermediate Similarity NPC294129
0.712 Intermediate Similarity NPC473890
0.712 Intermediate Similarity NPC243728
0.712 Intermediate Similarity NPC474164
0.7114 Intermediate Similarity NPC298469
0.7114 Intermediate Similarity NPC141669
0.7109 Intermediate Similarity NPC31907
0.7109 Intermediate Similarity NPC472252
0.7109 Intermediate Similarity NPC286969
0.7109 Intermediate Similarity NPC16520
0.7109 Intermediate Similarity NPC120123
0.7109 Intermediate Similarity NPC471885
0.7109 Intermediate Similarity NPC131479
0.7109 Intermediate Similarity NPC189852
0.7109 Intermediate Similarity NPC157659
0.7109 Intermediate Similarity NPC473020
0.7109 Intermediate Similarity NPC211879
0.7109 Intermediate Similarity NPC471886
0.7109 Intermediate Similarity NPC155010
0.7109 Intermediate Similarity NPC471888
0.7109 Intermediate Similarity NPC8039
0.7109 Intermediate Similarity NPC245280
0.7109 Intermediate Similarity NPC114874
0.7109 Intermediate Similarity NPC471887
0.7109 Intermediate Similarity NPC213190
0.7101 Intermediate Similarity NPC43842
0.7099 Intermediate Similarity NPC224098
0.7099 Intermediate Similarity NPC46190
0.7099 Intermediate Similarity NPC477809
0.7099 Intermediate Similarity NPC102016
0.7099 Intermediate Similarity NPC195116
0.7099 Intermediate Similarity NPC128133
0.7099 Intermediate Similarity NPC84956
0.7099 Intermediate Similarity NPC244086
0.7099 Intermediate Similarity NPC309278
0.7099 Intermediate Similarity NPC302057
0.7099 Intermediate Similarity NPC150372
0.7099 Intermediate Similarity NPC470433
0.7099 Intermediate Similarity NPC171073
0.7099 Intermediate Similarity NPC248746
0.7099 Intermediate Similarity NPC208383
0.7099 Intermediate Similarity NPC6806
0.7099 Intermediate Similarity NPC232054
0.7099 Intermediate Similarity NPC475550
0.7099 Intermediate Similarity NPC300557
0.7099 Intermediate Similarity NPC194207
0.7099 Intermediate Similarity NPC476835
0.7099 Intermediate Similarity NPC73243
0.7099 Intermediate Similarity NPC475333
0.7099 Intermediate Similarity NPC22779
0.7099 Intermediate Similarity NPC218571
0.7099 Intermediate Similarity NPC249265
0.7099 Intermediate Similarity NPC221110
0.7099 Intermediate Similarity NPC180459
0.7099 Intermediate Similarity NPC285253
0.7099 Intermediate Similarity NPC95051
0.709 Intermediate Similarity NPC477810
0.708 Intermediate Similarity NPC198325
0.708 Intermediate Similarity NPC50689
0.708 Intermediate Similarity NPC233391
0.708 Intermediate Similarity NPC107607
0.708 Intermediate Similarity NPC207243
0.7077 Intermediate Similarity NPC317534
0.7075 Intermediate Similarity NPC265908
0.7068 Intermediate Similarity NPC254255
0.7068 Intermediate Similarity NPC473567
0.7068 Intermediate Similarity NPC216595
0.7067 Intermediate Similarity NPC214821
0.7067 Intermediate Similarity NPC298067
0.7063 Intermediate Similarity NPC5358
0.7063 Intermediate Similarity NPC216260
0.7063 Intermediate Similarity NPC158088
0.7059 Intermediate Similarity NPC218093

  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 NPC297058 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
0.8421 Intermediate Similarity NPD8449 Approved
0.8358 Intermediate Similarity NPD8450 Suspended
0.7462 Intermediate Similarity NPD6430 Approved
0.7462 Intermediate Similarity NPD6429 Approved
0.7029 Intermediate Similarity NPD8033 Approved
0.6957 Remote Similarity NPD8377 Approved
0.6957 Remote Similarity NPD8294 Approved
0.6906 Remote Similarity NPD8296 Approved
0.6906 Remote Similarity NPD8378 Approved
0.6906 Remote Similarity NPD8335 Approved
0.6906 Remote Similarity NPD8380 Approved
0.6906 Remote Similarity NPD8379 Approved
0.6691 Remote Similarity NPD7328 Approved
0.6691 Remote Similarity NPD7327 Approved
0.6645 Remote Similarity NPD7625 Phase 1
0.6643 Remote Similarity NPD7516 Approved
0.6569 Remote Similarity NPD7335 Phase 2
0.6569 Remote Similarity NPD7337 Clinical (unspecified phase)
0.6569 Remote Similarity NPD7336 Phase 2
0.6549 Remote Similarity NPD7503 Approved
0.6531 Remote Similarity NPD8392 Approved
0.6531 Remote Similarity NPD8391 Approved
0.6531 Remote Similarity NPD8390 Approved
0.6507 Remote Similarity NPD8337 Approved
0.6507 Remote Similarity NPD8336 Approved
0.6483 Remote Similarity NPD8451 Approved
0.6438 Remote Similarity NPD8448 Approved
0.6429 Remote Similarity NPD4830 Approved
0.6429 Remote Similarity NPD4832 Approved
0.6429 Remote Similarity NPD4831 Approved
0.6403 Remote Similarity NPD3731 Phase 3
0.637 Remote Similarity NPD7507 Approved
0.6316 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6309 Remote Similarity NPD6914 Discontinued
0.6308 Remote Similarity NPD7991 Discontinued
0.6301 Remote Similarity NPD8341 Approved
0.6301 Remote Similarity NPD8340 Approved
0.6301 Remote Similarity NPD8299 Approved
0.6301 Remote Similarity NPD8342 Approved
0.6286 Remote Similarity NPD8133 Approved
0.6268 Remote Similarity NPD8137 Clinical (unspecified phase)
0.625 Remote Similarity NPD8415 Approved
0.6242 Remote Similarity NPD7319 Approved
0.6233 Remote Similarity NPD7829 Approved
0.6233 Remote Similarity NPD7830 Approved
0.6225 Remote Similarity NPD8338 Approved
0.6204 Remote Similarity NPD6412 Phase 2
0.6164 Remote Similarity NPD6436 Phase 3
0.6159 Remote Similarity NPD8174 Phase 2
0.6122 Remote Similarity NPD7122 Discontinued
0.6096 Remote Similarity NPD8517 Approved
0.6096 Remote Similarity NPD8444 Approved
0.6096 Remote Similarity NPD8515 Approved
0.6096 Remote Similarity NPD8513 Phase 3
0.6096 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6096 Remote Similarity NPD8516 Approved
0.6043 Remote Similarity NPD6686 Approved
0.6031 Remote Similarity NPD8171 Discontinued
0.6027 Remote Similarity NPD8346 Approved
0.6027 Remote Similarity NPD8345 Approved
0.6027 Remote Similarity NPD8347 Approved
0.6014 Remote Similarity NPD5357 Phase 1
0.6013 Remote Similarity NPD6845 Suspended
0.6 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6 Remote Similarity NPD4835 Approved
0.6 Remote Similarity NPD4837 Approved
0.6 Remote Similarity NPD4836 Approved
0.6 Remote Similarity NPD4838 Approved
0.5986 Remote Similarity NPD8269 Approved
0.5986 Remote Similarity NPD8268 Approved
0.5986 Remote Similarity NPD8267 Approved
0.5986 Remote Similarity NPD8266 Approved
0.596 Remote Similarity NPD7736 Approved
0.5946 Remote Similarity NPD8080 Discontinued
0.5946 Remote Similarity NPD6370 Approved
0.5906 Remote Similarity NPD7642 Approved
0.5894 Remote Similarity NPD8074 Phase 3
0.5894 Remote Similarity NPD8293 Discontinued
0.5879 Remote Similarity NPD8389 Clinical (unspecified phase)
0.5878 Remote Similarity NPD6908 Approved
0.5878 Remote Similarity NPD6909 Approved
0.5862 Remote Similarity NPD7755 Approved
0.5862 Remote Similarity NPD7754 Approved
0.5852 Remote Similarity NPD4282 Approved
0.5845 Remote Similarity NPD8087 Discontinued
0.5844 Remote Similarity NPD7260 Phase 2
0.5822 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5814 Remote Similarity NPD8308 Discontinued
0.5813 Remote Similarity NPD8384 Approved
0.5811 Remote Similarity NPD6059 Approved
0.5811 Remote Similarity NPD6054 Approved
0.5804 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5804 Remote Similarity NPD2204 Approved
0.58 Remote Similarity NPD8328 Phase 3
0.5786 Remote Similarity NPD6640 Phase 3
0.5782 Remote Similarity NPD7641 Discontinued
0.5769 Remote Similarity NPD7524 Approved
0.5758 Remote Similarity NPD3122 Phase 3
0.5758 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5753 Remote Similarity NPD6940 Discontinued
0.5725 Remote Similarity NPD4159 Approved
0.5724 Remote Similarity NPD8273 Phase 1
0.5714 Remote Similarity NPD7115 Discovery
0.5693 Remote Similarity NPD7638 Approved
0.5674 Remote Similarity NPD7333 Discontinued
0.5667 Remote Similarity NPD8470 Clinical (unspecified phase)
0.5667 Remote Similarity NPD6921 Approved
0.5667 Remote Similarity NPD6016 Approved
0.5667 Remote Similarity NPD6015 Approved
0.5659 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5658 Remote Similarity NPD7492 Approved
0.5658 Remote Similarity NPD591 Approved
0.5658 Remote Similarity NPD577 Phase 3
0.5652 Remote Similarity NPD7639 Approved
0.5652 Remote Similarity NPD7640 Approved
0.5634 Remote Similarity NPD8140 Approved
0.5629 Remote Similarity NPD5988 Approved
0.5625 Remote Similarity NPD7237 Clinical (unspecified phase)
0.5621 Remote Similarity NPD6616 Approved
0.5612 Remote Similarity NPD7999 Approved
0.5603 Remote Similarity NPD8170 Clinical (unspecified phase)

  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