Structure

Physi-Chem Properties

Molecular Weight:  1180.6
Volume:  1161.584
LogP:  3.711
LogD:  2.072
LogS:  -3.189
# Rotatable Bonds:  17
TPSA:  353.65
# H-Bond Aceptor:  23
# H-Bond Donor:  10
# Rings:  8
# Heavy Atoms:  23

MedChem Properties

QED Drug-Likeness Score:  0.039
Synthetic Accessibility Score:  7.128
Fsp3:  0.833
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:  -5.75
MDCK Permeability:  0.0003016487171407789
Pgp-inhibitor:  0.984
Pgp-substrate:  0.986
Human Intestinal Absorption (HIA):  0.953
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.052
Plasma Protein Binding (PPB):  75.45564270019531%
Volume Distribution (VD):  0.399
Pgp-substrate:  6.318439483642578%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.039
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.145
CYP2C9-inhibitor:  0.02
CYP2C9-substrate:  0.01
CYP2D6-inhibitor:  0.061
CYP2D6-substrate:  0.03
CYP3A4-inhibitor:  0.176
CYP3A4-substrate:  0.046

ADMET: Excretion

Clearance (CL):  0.818
Half-life (T1/2):  0.797

ADMET: Toxicity

hERG Blockers:  0.223
Human Hepatotoxicity (H-HT):  0.913
Drug-inuced Liver Injury (DILI):  0.785
AMES Toxicity:  0.052
Rat Oral Acute Toxicity:  0.065
Maximum Recommended Daily Dose:  0.977
Skin Sensitization:  0.051
Carcinogencity:  0.005
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.834

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

  Natural Product: NPC470518

Natural Product ID:  NPC470518
Common Name*:   Bunkankasaponin F
IUPAC Name:   (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-acetyloxy-8-hydroxy-8a-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3-hydroxy-6-methyl-4,5-bis[[(Z)-2-methylbut-2-enoyl]oxy]oxan-2-yl]oxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:   bunkankasaponin F
Standard InCHIKey:  HUGSFZKDDNLHSO-ODXRRWNRSA-N
Standard InCHI:  InChI=1S/C60H92O23/c1-14-26(3)50(73)79-43-28(5)75-53(42(70)44(43)80-51(74)27(4)15-2)83-47-48(76-29(6)63)60(25-62)31(22-55(47,7)8)30-16-17-34-57(11)20-19-36(56(9,10)33(57)18-21-58(34,12)59(30,13)23-35(60)64)78-54-46(40(68)39(67)45(81-54)49(71)72)82-52-41(69)38(66)37(65)32(24-61)77-52/h14-16,28,31-48,52-54,61-62,64-70H,17-25H2,1-13H3,(H,71,72)/b26-14-,27-15-/t28-,31+,32-,33+,34-,35-,36+,37-,38+,39+,40+,41-,42-,43+,44-,45+,46-,47+,48+,52+,53+,54-,57+,58-,59-,60+/m1/s1
SMILES:  CC=C(C)C(=O)OC1C(OC(C(C1OC(=O)C(=CC)C)O)OC2C(C3(C(CC2(C)C)C4=CCC5C6(CCC(C(C6CCC5(C4(CC3O)C)C)(C)C)OC7C(C(C(C(O7)C(=O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)CO)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2058433
PubChem CID:   66552846
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene 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
NPO30992 Xanthoceras sorbifolia Species Sapindaceae Eukaryota wood n.a. n.a. PMID[10691716]
NPO30992 Xanthoceras sorbifolia Species Sapindaceae Eukaryota husks Inner Mongolia, China 2004-SEP PMID[18549275]
NPO30992 Xanthoceras sorbifolia Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[22801644]
NPO30992 Xanthoceras sorbifolia Species Sapindaceae Eukaryota leaves n.a. n.a. PMID[23313635]

☑ 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 4970.0 nM PMID[526687]
NPT547 Cell Line BGC-823 Homo sapiens IC50 = 11300.0 nM PMID[526687]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 4300.0 nM PMID[526687]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 2280.0 nM PMID[526687]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 2450.0 nM PMID[526687]
NPT81 Cell Line A549 Homo sapiens IC50 = 5760.0 nM PMID[526687]
NPT453 Cell Line HT-1080 Homo sapiens IC50 = 1750.0 nM PMID[526687]
NPT1171 Cell Line HEp-2 Homo sapiens IC50 = 4970.0 nM PMID[526687]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3240.0 nM PMID[526687]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5220.0 nM PMID[526687]

☑ 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 NPC470518 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
1.0 High Similarity NPC1314
1.0 High Similarity NPC269484
1.0 High Similarity NPC305793
1.0 High Similarity NPC107536
1.0 High Similarity NPC141600
1.0 High Similarity NPC97918
1.0 High Similarity NPC88311
1.0 High Similarity NPC472267
1.0 High Similarity NPC244296
1.0 High Similarity NPC273878
1.0 High Similarity NPC280029
1.0 High Similarity NPC11577
1.0 High Similarity NPC252289
1.0 High Similarity NPC82380
1.0 High Similarity NPC9470
1.0 High Similarity NPC252657
1.0 High Similarity NPC115656
0.9916 High Similarity NPC271610
0.9916 High Similarity NPC476780
0.9916 High Similarity NPC476774
0.9916 High Similarity NPC476775
0.9915 High Similarity NPC477192
0.9915 High Similarity NPC477191
0.9915 High Similarity NPC477193
0.9915 High Similarity NPC477194
0.9833 High Similarity NPC71391
0.9833 High Similarity NPC30279
0.9833 High Similarity NPC476776
0.9833 High Similarity NPC277212
0.9833 High Similarity NPC46823
0.9833 High Similarity NPC178264
0.9833 High Similarity NPC312650
0.9833 High Similarity NPC473918
0.9833 High Similarity NPC192765
0.9832 High Similarity NPC265841
0.9832 High Similarity NPC470913
0.9832 High Similarity NPC470912
0.9832 High Similarity NPC477196
0.9832 High Similarity NPC477076
0.9832 High Similarity NPC47995
0.9832 High Similarity NPC477079
0.9832 High Similarity NPC477077
0.9752 High Similarity NPC225791
0.975 High Similarity NPC477197
0.975 High Similarity NPC478155
0.975 High Similarity NPC25998
0.9748 High Similarity NPC475281
0.9748 High Similarity NPC477078
0.9748 High Similarity NPC329923
0.9748 High Similarity NPC477075
0.9672 High Similarity NPC476777
0.9672 High Similarity NPC476778
0.9669 High Similarity NPC478153
0.9669 High Similarity NPC478150
0.9669 High Similarity NPC478154
0.9669 High Similarity NPC477195
0.9669 High Similarity NPC478152
0.9593 High Similarity NPC279915
0.9593 High Similarity NPC110700
0.959 High Similarity NPC476779
0.959 High Similarity NPC478151
0.9587 High Similarity NPC173435
0.9587 High Similarity NPC301639
0.9587 High Similarity NPC476074
0.9587 High Similarity NPC45346
0.9587 High Similarity NPC134914
0.9587 High Similarity NPC475377
0.9587 High Similarity NPC264566
0.9587 High Similarity NPC478065
0.9587 High Similarity NPC329993
0.9587 High Similarity NPC478064
0.9587 High Similarity NPC262796
0.9587 High Similarity NPC172374
0.9587 High Similarity NPC475167
0.9421 High Similarity NPC470475
0.9339 High Similarity NPC470516
0.9333 High Similarity NPC471962
0.9333 High Similarity NPC247315
0.9333 High Similarity NPC471963
0.9328 High Similarity NPC213952
0.9322 High Similarity NPC118440
0.9322 High Similarity NPC236657
0.9262 High Similarity NPC470476
0.925 High Similarity NPC262199
0.925 High Similarity NPC202666
0.925 High Similarity NPC257211
0.925 High Similarity NPC14617
0.925 High Similarity NPC471961
0.925 High Similarity NPC471964
0.9244 High Similarity NPC222580
0.9244 High Similarity NPC22956
0.9244 High Similarity NPC104372
0.9244 High Similarity NPC31838
0.9244 High Similarity NPC11242
0.9244 High Similarity NPC223301
0.9244 High Similarity NPC62725
0.9244 High Similarity NPC301449
0.9244 High Similarity NPC302887
0.9244 High Similarity NPC159309
0.9244 High Similarity NPC114484
0.9244 High Similarity NPC86222
0.9244 High Similarity NPC297263
0.9244 High Similarity NPC171544
0.9244 High Similarity NPC64715
0.9244 High Similarity NPC187618
0.9174 High Similarity NPC23275
0.9174 High Similarity NPC33068
0.9167 High Similarity NPC471965
0.9167 High Similarity NPC131469
0.9167 High Similarity NPC80986
0.9167 High Similarity NPC10607
0.9167 High Similarity NPC187290
0.9167 High Similarity NPC162574
0.9167 High Similarity NPC4749
0.9167 High Similarity NPC475591
0.9167 High Similarity NPC313110
0.9167 High Similarity NPC236870
0.9167 High Similarity NPC21691
0.9098 High Similarity NPC284449
0.9098 High Similarity NPC285091
0.9091 High Similarity NPC258617
0.9091 High Similarity NPC478066
0.9091 High Similarity NPC30735
0.9091 High Similarity NPC283417
0.9091 High Similarity NPC200049
0.9091 High Similarity NPC281148
0.9091 High Similarity NPC302543
0.9091 High Similarity NPC2370
0.9091 High Similarity NPC235405
0.9091 High Similarity NPC44716
0.9076 High Similarity NPC469945
0.9076 High Similarity NPC114441
0.9076 High Similarity NPC39211
0.9076 High Similarity NPC35405
0.9076 High Similarity NPC214484
0.9076 High Similarity NPC11551
0.9076 High Similarity NPC309780
0.9076 High Similarity NPC473884
0.9076 High Similarity NPC472949
0.9076 High Similarity NPC157868
0.9076 High Similarity NPC192791
0.9076 High Similarity NPC6377
0.9076 High Similarity NPC208381
0.9076 High Similarity NPC180550
0.9076 High Similarity NPC475171
0.9068 High Similarity NPC224121
0.9055 High Similarity NPC141215
0.9055 High Similarity NPC190065
0.9055 High Similarity NPC471089
0.9016 High Similarity NPC160452
0.9016 High Similarity NPC470477
0.9008 High Similarity NPC40775
0.9008 High Similarity NPC107966
0.9008 High Similarity NPC249848
0.9008 High Similarity NPC235438
0.8992 High Similarity NPC286347
0.8992 High Similarity NPC470515
0.8992 High Similarity NPC471548
0.8984 High Similarity NPC596
0.8984 High Similarity NPC295885
0.8984 High Similarity NPC140045
0.8976 High Similarity NPC262813
0.896 High Similarity NPC43589
0.896 High Similarity NPC300655
0.896 High Similarity NPC222951
0.896 High Similarity NPC311178
0.8952 High Similarity NPC472270
0.8952 High Similarity NPC23020
0.8952 High Similarity NPC472269
0.8952 High Similarity NPC472268
0.8952 High Similarity NPC112492
0.8943 High Similarity NPC181066
0.8943 High Similarity NPC475368
0.8943 High Similarity NPC469947
0.8943 High Similarity NPC470218
0.8926 High Similarity NPC75417
0.8926 High Similarity NPC242840
0.8926 High Similarity NPC31193
0.8917 High Similarity NPC470517
0.8917 High Similarity NPC473401
0.8917 High Similarity NPC470915
0.8917 High Similarity NPC470911
0.8908 High Similarity NPC300419
0.8908 High Similarity NPC473405
0.8906 High Similarity NPC251998
0.8889 High Similarity NPC319719
0.8889 High Similarity NPC183816
0.8889 High Similarity NPC322904
0.8889 High Similarity NPC473679
0.8889 High Similarity NPC475444
0.8889 High Similarity NPC233223
0.8889 High Similarity NPC324933
0.8889 High Similarity NPC196874
0.8889 High Similarity NPC475177
0.8843 High Similarity NPC294112
0.8843 High Similarity NPC476127
0.8843 High Similarity NPC476150
0.8833 High Similarity NPC109588
0.8824 High Similarity NPC291903
0.8824 High Similarity NPC37134

  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 NPC470518 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
0.925 High Similarity NPD8328 Phase 3
0.875 High Similarity NPD8295 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD7319 Approved
0.7953 Intermediate Similarity NPD8294 Approved
0.7953 Intermediate Similarity NPD8377 Approved
0.7939 Intermediate Similarity NPD7736 Approved
0.7934 Intermediate Similarity NPD6686 Approved
0.7923 Intermediate Similarity NPD7507 Approved
0.7903 Intermediate Similarity NPD8133 Approved
0.7891 Intermediate Similarity NPD8380 Approved
0.7891 Intermediate Similarity NPD8513 Phase 3
0.7891 Intermediate Similarity NPD8379 Approved
0.7891 Intermediate Similarity NPD8515 Approved
0.7891 Intermediate Similarity NPD8378 Approved
0.7891 Intermediate Similarity NPD8296 Approved
0.7891 Intermediate Similarity NPD8335 Approved
0.7891 Intermediate Similarity NPD8517 Approved
0.7891 Intermediate Similarity NPD8516 Approved
0.7869 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7752 Intermediate Similarity NPD8033 Approved
0.7597 Intermediate Similarity NPD7516 Approved
0.7594 Intermediate Similarity NPD8293 Discontinued
0.7557 Intermediate Similarity NPD6370 Approved
0.7519 Intermediate Similarity NPD7327 Approved
0.7519 Intermediate Similarity NPD7328 Approved
0.75 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD7503 Approved
0.7444 Intermediate Similarity NPD7492 Approved
0.7405 Intermediate Similarity NPD6054 Approved
0.7405 Intermediate Similarity NPD6319 Approved
0.7388 Intermediate Similarity NPD6616 Approved
0.7333 Intermediate Similarity NPD7078 Approved
0.728 Intermediate Similarity NPD6412 Phase 2
0.7273 Intermediate Similarity NPD6059 Approved
0.7266 Intermediate Similarity NPD8297 Approved
0.7266 Intermediate Similarity NPD6882 Approved
0.7218 Intermediate Similarity NPD6015 Approved
0.7218 Intermediate Similarity NPD6016 Approved
0.719 Intermediate Similarity NPD7902 Approved
0.7188 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7115 Discovery
0.7176 Intermediate Similarity NPD6009 Approved
0.7164 Intermediate Similarity NPD5988 Approved
0.7131 Intermediate Similarity NPD7638 Approved
0.7131 Intermediate Similarity NPD4225 Approved
0.7083 Intermediate Similarity NPD7748 Approved
0.7073 Intermediate Similarity NPD7639 Approved
0.7073 Intermediate Similarity NPD7640 Approved
0.7054 Intermediate Similarity NPD6649 Approved
0.7054 Intermediate Similarity NPD6650 Approved
0.7031 Intermediate Similarity NPD6373 Approved
0.7031 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD6372 Approved
0.6977 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6963 Remote Similarity NPD6921 Approved
0.6957 Remote Similarity NPD8074 Phase 3
0.6953 Remote Similarity NPD6881 Approved
0.6953 Remote Similarity NPD6899 Approved
0.6947 Remote Similarity NPD4632 Approved
0.6942 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6942 Remote Similarity NPD7900 Approved
0.6929 Remote Similarity NPD5739 Approved
0.6929 Remote Similarity NPD6402 Approved
0.6929 Remote Similarity NPD7128 Approved
0.6929 Remote Similarity NPD6675 Approved
0.6923 Remote Similarity NPD8130 Phase 1
0.6917 Remote Similarity NPD7515 Phase 2
0.6875 Remote Similarity NPD5697 Approved
0.6846 Remote Similarity NPD7290 Approved
0.6846 Remote Similarity NPD7102 Approved
0.6846 Remote Similarity NPD6883 Approved
0.6822 Remote Similarity NPD7320 Approved
0.6794 Remote Similarity NPD6617 Approved
0.6794 Remote Similarity NPD6869 Approved
0.6794 Remote Similarity NPD6847 Approved
0.6786 Remote Similarity NPD6033 Approved
0.6769 Remote Similarity NPD6014 Approved
0.6769 Remote Similarity NPD6012 Approved
0.6769 Remote Similarity NPD6013 Approved
0.6744 Remote Similarity NPD5701 Approved
0.6744 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6739 Remote Similarity NPD7604 Phase 2
0.672 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6719 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6718 Remote Similarity NPD4634 Approved
0.6715 Remote Similarity NPD5983 Phase 2
0.6692 Remote Similarity NPD6011 Approved
0.6644 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6643 Remote Similarity NPD6336 Discontinued
0.6619 Remote Similarity NPD7830 Approved
0.6619 Remote Similarity NPD7829 Approved
0.6615 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6575 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7799 Discontinued
0.6562 Remote Similarity NPD7632 Discontinued
0.6557 Remote Similarity NPD6698 Approved
0.6557 Remote Similarity NPD46 Approved
0.6541 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6528 Remote Similarity NPD7260 Phase 2
0.6507 Remote Similarity NPD8415 Approved
0.6484 Remote Similarity NPD5344 Discontinued
0.6479 Remote Similarity NPD8448 Approved
0.6471 Remote Similarity NPD6274 Approved
0.6471 Remote Similarity NPD7625 Phase 1
0.6458 Remote Similarity NPD8392 Approved
0.6458 Remote Similarity NPD8391 Approved
0.6458 Remote Similarity NPD8390 Approved
0.6449 Remote Similarity NPD7101 Approved
0.6449 Remote Similarity NPD7100 Approved
0.6434 Remote Similarity NPD5211 Phase 2
0.6412 Remote Similarity NPD8368 Discontinued
0.6408 Remote Similarity NPD8451 Approved
0.6406 Remote Similarity NPD4696 Approved
0.6406 Remote Similarity NPD5286 Approved
0.6406 Remote Similarity NPD5285 Approved
0.6383 Remote Similarity NPD6067 Discontinued
0.6378 Remote Similarity NPD4755 Approved
0.6378 Remote Similarity NPD6083 Phase 2
0.6378 Remote Similarity NPD6084 Phase 2
0.6377 Remote Similarity NPD6335 Approved
0.6371 Remote Similarity NPD8034 Phase 2
0.6371 Remote Similarity NPD6411 Approved
0.6371 Remote Similarity NPD7983 Approved
0.6371 Remote Similarity NPD8035 Phase 2
0.635 Remote Similarity NPD6868 Approved
0.6343 Remote Similarity NPD6371 Approved
0.6336 Remote Similarity NPD5141 Approved
0.632 Remote Similarity NPD5778 Approved
0.632 Remote Similarity NPD5779 Approved
0.6312 Remote Similarity NPD8080 Discontinued
0.6311 Remote Similarity NPD3573 Approved
0.6308 Remote Similarity NPD5225 Approved
0.6308 Remote Similarity NPD4633 Approved
0.6308 Remote Similarity NPD5226 Approved
0.6308 Remote Similarity NPD5224 Approved
0.6304 Remote Similarity NPD6317 Approved
0.6301 Remote Similarity NPD8407 Phase 2
0.6299 Remote Similarity NPD4697 Phase 3
0.6299 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6299 Remote Similarity NPD5222 Approved
0.6299 Remote Similarity NPD5221 Approved
0.629 Remote Similarity NPD7838 Discovery
0.6288 Remote Similarity NPD6008 Approved
0.6279 Remote Similarity NPD4700 Approved
0.6268 Remote Similarity NPD7642 Approved
0.626 Remote Similarity NPD5174 Approved
0.626 Remote Similarity NPD5175 Approved
0.6259 Remote Similarity NPD6845 Suspended
0.6259 Remote Similarity NPD6314 Approved
0.6259 Remote Similarity NPD6313 Approved
0.625 Remote Similarity NPD5173 Approved
0.625 Remote Similarity NPD6053 Discontinued
0.6241 Remote Similarity NPD6908 Approved
0.6241 Remote Similarity NPD6909 Approved
0.6241 Remote Similarity NPD8444 Approved
0.624 Remote Similarity NPD6079 Approved
0.6235 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6233 Remote Similarity NPD5956 Approved
0.6231 Remote Similarity NPD5223 Approved
0.6224 Remote Similarity NPD8342 Approved
0.6224 Remote Similarity NPD8299 Approved
0.6224 Remote Similarity NPD8341 Approved
0.6224 Remote Similarity NPD8340 Approved
0.621 Remote Similarity NPD5328 Approved
0.621 Remote Similarity NPD6101 Approved
0.621 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6207 Remote Similarity NPD8337 Approved
0.6207 Remote Similarity NPD8336 Approved
0.6202 Remote Similarity NPD5696 Approved
0.6194 Remote Similarity NPD4730 Approved
0.6194 Remote Similarity NPD4729 Approved
0.619 Remote Similarity NPD8171 Discontinued
0.619 Remote Similarity NPD6399 Phase 3
0.6186 Remote Similarity NPD7645 Phase 2
0.618 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6165 Remote Similarity NPD4768 Approved
0.6165 Remote Similarity NPD4767 Approved
0.6158 Remote Similarity NPD8435 Approved
0.6154 Remote Similarity NPD6648 Approved
0.6149 Remote Similarity NPD8338 Approved
0.6129 Remote Similarity NPD5737 Approved
0.6129 Remote Similarity NPD6672 Approved
0.6127 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6127 Remote Similarity NPD6291 Clinical (unspecified phase)
0.612 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6103 Remote Similarity NPD5247 Approved
0.6103 Remote Similarity NPD5248 Approved
0.6103 Remote Similarity NPD5249 Phase 3
0.6103 Remote Similarity NPD5250 Approved
0.6103 Remote Similarity NPD5251 Approved
0.6098 Remote Similarity NPD3618 Phase 1
0.6094 Remote Similarity NPD5695 Phase 3
0.6094 Remote Similarity NPD1698 Clinical (unspecified phase)
0.608 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6075 Remote Similarity NPD8320 Phase 1
0.6075 Remote Similarity NPD8319 Approved
0.6074 Remote Similarity NPD5128 Approved
0.6067 Remote Similarity NPD8361 Approved
0.6067 Remote Similarity NPD8360 Approved
0.6057 Remote Similarity NPD8312 Approved

  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