Structure

Physi-Chem Properties

Molecular Weight:  486.33
Volume:  520.695
LogP:  3.909
LogD:  4.108
LogS:  -3.419
# Rotatable Bonds:  3
TPSA:  94.83
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.416
Synthetic Accessibility Score:  4.864
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.695
MDCK Permeability:  7.154667400754988e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.08
30% Bioavailability (F30%):  0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  88.3008041381836%
Volume Distribution (VD):  0.57
Pgp-substrate:  4.266695499420166%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.533
CYP2C19-inhibitor:  0.008
CYP2C19-substrate:  0.872
CYP2C9-inhibitor:  0.114
CYP2C9-substrate:  0.52
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.137
CYP3A4-inhibitor:  0.094
CYP3A4-substrate:  0.093

ADMET: Excretion

Clearance (CL):  1.516
Half-life (T1/2):  0.515

ADMET: Toxicity

hERG Blockers:  0.038
Human Hepatotoxicity (H-HT):  0.403
Drug-inuced Liver Injury (DILI):  0.003
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.065
Maximum Recommended Daily Dose:  0.082
Skin Sensitization:  0.067
Carcinogencity:  0.012
Eye Corrosion:  0.342
Eye Irritation:  0.402
Respiratory Toxicity:  0.923

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC213832

Natural Product ID:  NPC213832
Common Name*:   3Alpha-Hydroxylup-20(29)-Ene-23,28-Dioic Acid
IUPAC Name:   (1R,3aS,5aR,5bR,7aR,8S,9R,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,8-dicarboxylic acid
Synonyms:  
Standard InCHIKey:  NSLGONDVJPFEEN-JOPFMIIHSA-N
Standard InCHI:  InChI=1S/C30H46O5/c1-17(2)18-9-14-30(25(34)35)16-15-27(4)19(23(18)30)7-8-20-26(3)12-11-22(31)29(6,24(32)33)21(26)10-13-28(20,27)5/h18-23,31H,1,7-16H2,2-6H3,(H,32,33)(H,34,35)/t18-,19+,20+,21+,22+,23+,26+,27+,28+,29-,30-/m0/s1
SMILES:  CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@H]([C@@]1(C)C(=O)O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1271534
PubChem CID:   14466871
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)89267-5]
NPO6003 Halorosellinia oceanica Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[11454459]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12882150]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[15666542]
NPO10814 Ilex latifolia Species Aquifoliaceae Eukaryota n.a. stem n.a. PMID[16252920]
NPO12610 Diospyros dendo Species Ebenaceae Eukaryota n.a. n.a. n.a. PMID[16441080]
NPO3029 Daedalea dickinsii Species Coriolaceae Eukaryota n.a. mycelium n.a. PMID[17986791]
NPO17954 Narcissus tazetta Species Amaryllidaceae Eukaryota n.a. Turkey n.a. PMID[19299148]
NPO6003 Halorosellinia oceanica Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[20218656]
NPO29834 Acanthopanax koreanum n.a. n.a. n.a. n.a. n.a. n.a. PMID[20621475]
NPO29834 Acanthopanax koreanum n.a. n.a. n.a. steamed leaves n.a. n.a. PMID[20932756]
NPO6003 Halorosellinia oceanica Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[21265556]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota Tubers n.a. n.a. PMID[23356207]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32129622]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. trunk bark n.a. PMID[556731]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[9392889]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Tuber n.a. n.a. Database[FooDB]
NPO22136 Hedysarum alpinum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Tubers n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17954 Narcissus tazetta Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10814 Ilex latifolia Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29834 Acanthopanax koreanum n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO29219 Primula veris Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5200 Diphylleia grayi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5200 Diphylleia grayi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10814 Ilex latifolia Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29219 Primula veris Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17954 Narcissus tazetta Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5200 Diphylleia grayi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12836 Mentha javanica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29219 Primula veris Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13061 Balanocarpus zeylanicus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3568 Myristica dactyloides Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1349 Zanthoxylum zanthoxyloides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24374 Brunsvigia orientalis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6003 Halorosellinia oceanica Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17954 Narcissus tazetta Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14426 Halictus sexcinctus Species Halictidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22136 Hedysarum alpinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12610 Diospyros dendo Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12019 Orontium japonicum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3029 Daedalea dickinsii Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10670 Bidens frondosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25663 Piscidia piscipula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23922 Helichrysum oxyphyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15944 Primnoa resedaeformis Species Primnoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23679 Streptomyces roseiscleroticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25131 Parmelia weberi Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5200 Diphylleia grayi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12781 Schefflera heptaphylla Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10814 Ilex latifolia Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15495 Narcissus cantabricus Species Amaryllidaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 110100.0 nM PMID[549778]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 222900.0 nM PMID[549778]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 246900.0 nM PMID[549779]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition < 50.0 % PMID[549776]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 54.0 ug.mL-1 PMID[549777]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 IC50 = 64400.0 nM PMID[549779]
NPT2 Others Unspecified Ratio CC50/IC50 = 3.8 n.a. PMID[549779]

☑ 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 NPC213832 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 NPC57954
0.988 High Similarity NPC471900
0.9759 High Similarity NPC269360
0.9759 High Similarity NPC264005
0.9651 High Similarity NPC287118
0.9651 High Similarity NPC473690
0.9651 High Similarity NPC471902
0.9647 High Similarity NPC169933
0.9639 High Similarity NPC2783
0.9535 High Similarity NPC475416
0.9535 High Similarity NPC471901
0.9524 High Similarity NPC33768
0.9518 High Similarity NPC294438
0.9518 High Similarity NPC264317
0.9412 High Similarity NPC474719
0.9412 High Similarity NPC146937
0.9412 High Similarity NPC16377
0.9405 High Similarity NPC12774
0.9302 High Similarity NPC220498
0.9286 High Similarity NPC201655
0.9186 High Similarity NPC4309
0.9101 High Similarity NPC277399
0.908 High Similarity NPC247312
0.908 High Similarity NPC271974
0.907 High Similarity NPC134197
0.907 High Similarity NPC57469
0.9048 High Similarity NPC475726
0.9048 High Similarity NPC472743
0.9 High Similarity NPC263135
0.9 High Similarity NPC288906
0.9 High Similarity NPC205173
0.9 High Similarity NPC266431
0.8989 High Similarity NPC291373
0.8989 High Similarity NPC244356
0.8989 High Similarity NPC224060
0.8966 High Similarity NPC211162
0.8966 High Similarity NPC183374
0.8941 High Similarity NPC74595
0.8941 High Similarity NPC264665
0.8941 High Similarity NPC475745
0.8941 High Similarity NPC474482
0.8901 High Similarity NPC234564
0.8876 High Similarity NPC160506
0.8876 High Similarity NPC288833
0.8876 High Similarity NPC324341
0.8876 High Similarity NPC966
0.8876 High Similarity NPC228784
0.8876 High Similarity NPC155120
0.8876 High Similarity NPC282616
0.8864 High Similarity NPC475921
0.8864 High Similarity NPC474704
0.8837 High Similarity NPC98270
0.8837 High Similarity NPC292553
0.8824 High Similarity NPC471037
0.8804 High Similarity NPC253586
0.8791 High Similarity NPC210214
0.8764 High Similarity NPC86372
0.8764 High Similarity NPC172361
0.8736 High Similarity NPC269396
0.8736 High Similarity NPC472738
0.8736 High Similarity NPC187545
0.8736 High Similarity NPC80590
0.8736 High Similarity NPC98236
0.8721 High Similarity NPC474233
0.8721 High Similarity NPC475509
0.8696 High Similarity NPC327788
0.8681 High Similarity NPC303863
0.8681 High Similarity NPC222047
0.8681 High Similarity NPC47853
0.8667 High Similarity NPC211403
0.8667 High Similarity NPC6255
0.8667 High Similarity NPC198242
0.8667 High Similarity NPC471588
0.8652 High Similarity NPC24772
0.8652 High Similarity NPC293048
0.8652 High Similarity NPC270768
0.8652 High Similarity NPC234346
0.8652 High Similarity NPC59263
0.8652 High Similarity NPC130520
0.8652 High Similarity NPC61543
0.8652 High Similarity NPC121798
0.8652 High Similarity NPC263393
0.8652 High Similarity NPC116146
0.8652 High Similarity NPC225585
0.8652 High Similarity NPC127689
0.8636 High Similarity NPC474684
0.8636 High Similarity NPC142361
0.8636 High Similarity NPC4643
0.8617 High Similarity NPC180733
0.8617 High Similarity NPC108371
0.8617 High Similarity NPC94906
0.8617 High Similarity NPC37047
0.8617 High Similarity NPC41971
0.8605 High Similarity NPC245866
0.8605 High Similarity NPC471036
0.8605 High Similarity NPC5280
0.8605 High Similarity NPC291320
0.8587 High Similarity NPC148523
0.8571 High Similarity NPC201459
0.8571 High Similarity NPC298554
0.8571 High Similarity NPC192744
0.8571 High Similarity NPC475061
0.8571 High Similarity NPC294263
0.8556 High Similarity NPC470589
0.8556 High Similarity NPC126369
0.8556 High Similarity NPC130278
0.8556 High Similarity NPC111110
0.8554 High Similarity NPC474433
0.8554 High Similarity NPC68828
0.8554 High Similarity NPC298168
0.8554 High Similarity NPC143133
0.8539 High Similarity NPC52169
0.8539 High Similarity NPC182797
0.8539 High Similarity NPC472739
0.8539 High Similarity NPC242864
0.8526 High Similarity NPC75941
0.8526 High Similarity NPC71706
0.8523 High Similarity NPC70661
0.8523 High Similarity NPC168231
0.8523 High Similarity NPC28252
0.8523 High Similarity NPC55309
0.8511 High Similarity NPC16911
0.8511 High Similarity NPC164349
0.8511 High Similarity NPC472028
0.8511 High Similarity NPC78427
0.8495 Intermediate Similarity NPC201657
0.8495 Intermediate Similarity NPC329910
0.8495 Intermediate Similarity NPC13949
0.8495 Intermediate Similarity NPC132824
0.8495 Intermediate Similarity NPC98874
0.8495 Intermediate Similarity NPC120708
0.8488 Intermediate Similarity NPC110780
0.8478 Intermediate Similarity NPC474529
0.8478 Intermediate Similarity NPC78580
0.8478 Intermediate Similarity NPC209868
0.8478 Intermediate Similarity NPC184006
0.8478 Intermediate Similarity NPC23621
0.8478 Intermediate Similarity NPC470385
0.8478 Intermediate Similarity NPC470386
0.8478 Intermediate Similarity NPC469982
0.8462 Intermediate Similarity NPC250753
0.8462 Intermediate Similarity NPC189520
0.8444 Intermediate Similarity NPC25906
0.8444 Intermediate Similarity NPC143232
0.8444 Intermediate Similarity NPC198664
0.8444 Intermediate Similarity NPC274330
0.8444 Intermediate Similarity NPC290972
0.8444 Intermediate Similarity NPC64872
0.8438 Intermediate Similarity NPC271980
0.8438 Intermediate Similarity NPC124544
0.8438 Intermediate Similarity NPC193934
0.8434 Intermediate Similarity NPC78067
0.8434 Intermediate Similarity NPC246445
0.8434 Intermediate Similarity NPC278091
0.8434 Intermediate Similarity NPC4209
0.8434 Intermediate Similarity NPC93662
0.8427 Intermediate Similarity NPC159046
0.8427 Intermediate Similarity NPC102683
0.8427 Intermediate Similarity NPC233836
0.8427 Intermediate Similarity NPC88716
0.8427 Intermediate Similarity NPC51700
0.8427 Intermediate Similarity NPC130577
0.8427 Intermediate Similarity NPC252714
0.8427 Intermediate Similarity NPC98442
0.8427 Intermediate Similarity NPC96496
0.8427 Intermediate Similarity NPC187376
0.8427 Intermediate Similarity NPC259009
0.8427 Intermediate Similarity NPC293564
0.8427 Intermediate Similarity NPC242468
0.8427 Intermediate Similarity NPC18064
0.8427 Intermediate Similarity NPC165895
0.8427 Intermediate Similarity NPC68160
0.8427 Intermediate Similarity NPC171203
0.8427 Intermediate Similarity NPC307426
0.8427 Intermediate Similarity NPC142415
0.8421 Intermediate Similarity NPC287676
0.8409 Intermediate Similarity NPC190704
0.8409 Intermediate Similarity NPC76518
0.8409 Intermediate Similarity NPC471034
0.8404 Intermediate Similarity NPC261935
0.8404 Intermediate Similarity NPC106112
0.8387 Intermediate Similarity NPC195715
0.8387 Intermediate Similarity NPC470229
0.8387 Intermediate Similarity NPC88310
0.8387 Intermediate Similarity NPC23241
0.8387 Intermediate Similarity NPC279974
0.8387 Intermediate Similarity NPC470232
0.8372 Intermediate Similarity NPC474484
0.8372 Intermediate Similarity NPC103754
0.837 Intermediate Similarity NPC229281
0.837 Intermediate Similarity NPC470375
0.837 Intermediate Similarity NPC86368
0.837 Intermediate Similarity NPC470376
0.8352 Intermediate Similarity NPC149761
0.8352 Intermediate Similarity NPC227467
0.8352 Intermediate Similarity NPC210037
0.8352 Intermediate Similarity NPC180849
0.8352 Intermediate Similarity NPC261994
0.8352 Intermediate Similarity NPC470378
0.8352 Intermediate Similarity NPC477872

  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 NPC213832 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
0.9518 High Similarity NPD7520 Clinical (unspecified phase)
0.8876 High Similarity NPD8035 Phase 2
0.8876 High Similarity NPD8034 Phase 2
0.8434 Intermediate Similarity NPD6117 Approved
0.8333 Intermediate Similarity NPD6116 Phase 1
0.8261 Intermediate Similarity NPD7515 Phase 2
0.8235 Intermediate Similarity NPD6114 Approved
0.8235 Intermediate Similarity NPD6115 Approved
0.8235 Intermediate Similarity NPD6118 Approved
0.8235 Intermediate Similarity NPD6697 Approved
0.8193 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD7748 Approved
0.7889 Intermediate Similarity NPD4786 Approved
0.7849 Intermediate Similarity NPD5328 Approved
0.7789 Intermediate Similarity NPD6399 Phase 3
0.7778 Intermediate Similarity NPD4788 Approved
0.7738 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD3618 Phase 1
0.7684 Intermediate Similarity NPD6079 Approved
0.7667 Intermediate Similarity NPD3667 Approved
0.7653 Intermediate Similarity NPD7902 Approved
0.7647 Intermediate Similarity NPD6675 Approved
0.7647 Intermediate Similarity NPD5739 Approved
0.7647 Intermediate Similarity NPD6402 Approved
0.7647 Intermediate Similarity NPD7128 Approved
0.764 Intermediate Similarity NPD7525 Registered
0.7576 Intermediate Similarity NPD7638 Approved
0.75 Intermediate Similarity NPD6881 Approved
0.75 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6899 Approved
0.75 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7640 Approved
0.75 Intermediate Similarity NPD7639 Approved
0.7475 Intermediate Similarity NPD4755 Approved
0.7475 Intermediate Similarity NPD6084 Phase 2
0.7475 Intermediate Similarity NPD6083 Phase 2
0.7431 Intermediate Similarity NPD7115 Discovery
0.7429 Intermediate Similarity NPD6372 Approved
0.7429 Intermediate Similarity NPD6373 Approved
0.7423 Intermediate Similarity NPD4202 Approved
0.7404 Intermediate Similarity NPD5701 Approved
0.7404 Intermediate Similarity NPD5697 Approved
0.7374 Intermediate Similarity NPD5221 Approved
0.7374 Intermediate Similarity NPD5222 Approved
0.7374 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD4697 Phase 3
0.7368 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6883 Approved
0.7358 Intermediate Similarity NPD7102 Approved
0.7358 Intermediate Similarity NPD7290 Approved
0.7347 Intermediate Similarity NPD7900 Approved
0.7347 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7645 Phase 2
0.7327 Intermediate Similarity NPD4696 Approved
0.7327 Intermediate Similarity NPD5285 Approved
0.7327 Intermediate Similarity NPD5286 Approved
0.7327 Intermediate Similarity NPD4700 Approved
0.7326 Intermediate Similarity NPD6081 Approved
0.7312 Intermediate Similarity NPD3133 Approved
0.7312 Intermediate Similarity NPD3665 Phase 1
0.7312 Intermediate Similarity NPD3666 Approved
0.73 Intermediate Similarity NPD5173 Approved
0.7292 Intermediate Similarity NPD4753 Phase 2
0.729 Intermediate Similarity NPD6869 Approved
0.729 Intermediate Similarity NPD6847 Approved
0.729 Intermediate Similarity NPD6650 Approved
0.729 Intermediate Similarity NPD6617 Approved
0.729 Intermediate Similarity NPD6649 Approved
0.729 Intermediate Similarity NPD8130 Phase 1
0.7273 Intermediate Similarity NPD3703 Phase 2
0.7264 Intermediate Similarity NPD6014 Approved
0.7264 Intermediate Similarity NPD6012 Approved
0.7264 Intermediate Similarity NPD6013 Approved
0.7222 Intermediate Similarity NPD8297 Approved
0.7222 Intermediate Similarity NPD6882 Approved
0.7209 Intermediate Similarity NPD4789 Approved
0.7209 Intermediate Similarity NPD4245 Approved
0.7209 Intermediate Similarity NPD4244 Approved
0.7188 Intermediate Similarity NPD5737 Approved
0.7188 Intermediate Similarity NPD6672 Approved
0.7184 Intermediate Similarity NPD5226 Approved
0.7184 Intermediate Similarity NPD4633 Approved
0.7184 Intermediate Similarity NPD5211 Phase 2
0.7184 Intermediate Similarity NPD5225 Approved
0.7184 Intermediate Similarity NPD5224 Approved
0.7176 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD5360 Phase 3
0.717 Intermediate Similarity NPD6011 Approved
0.7158 Intermediate Similarity NPD7146 Approved
0.7158 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7521 Approved
0.7158 Intermediate Similarity NPD7334 Approved
0.7158 Intermediate Similarity NPD6409 Approved
0.7158 Intermediate Similarity NPD6684 Approved
0.7158 Intermediate Similarity NPD5330 Approved
0.7156 Intermediate Similarity NPD8133 Approved
0.7143 Intermediate Similarity NPD6411 Approved
0.7143 Intermediate Similarity NPD4224 Phase 2
0.713 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD3668 Phase 3
0.7115 Intermediate Similarity NPD5174 Approved
0.7115 Intermediate Similarity NPD5175 Approved
0.71 Intermediate Similarity NPD5695 Phase 3
0.7093 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD3698 Phase 2
0.7087 Intermediate Similarity NPD5223 Approved
0.7079 Intermediate Similarity NPD6942 Approved
0.7079 Intermediate Similarity NPD7339 Approved
0.7059 Intermediate Similarity NPD5696 Approved
0.7048 Intermediate Similarity NPD5141 Approved
0.7037 Intermediate Similarity NPD4634 Approved
0.7024 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7632 Discontinued
0.701 Intermediate Similarity NPD6903 Approved
0.6981 Remote Similarity NPD4768 Approved
0.6981 Remote Similarity NPD4767 Approved
0.6979 Remote Similarity NPD5279 Phase 3
0.697 Remote Similarity NPD7637 Suspended
0.6952 Remote Similarity NPD4754 Approved
0.6949 Remote Similarity NPD7736 Approved
0.6939 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6101 Approved
0.6932 Remote Similarity NPD5777 Approved
0.6931 Remote Similarity NPD4629 Approved
0.6931 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6931 Remote Similarity NPD5210 Approved
0.693 Remote Similarity NPD6319 Approved
0.6915 Remote Similarity NPD4223 Phase 3
0.6915 Remote Similarity NPD4221 Approved
0.6893 Remote Similarity NPD4225 Approved
0.6891 Remote Similarity NPD7319 Approved
0.6889 Remote Similarity NPD3702 Approved
0.6875 Remote Similarity NPD5329 Approved
0.6875 Remote Similarity NPD6274 Approved
0.6875 Remote Similarity NPD6868 Approved
0.6852 Remote Similarity NPD4730 Approved
0.6852 Remote Similarity NPD5128 Approved
0.6852 Remote Similarity NPD4729 Approved
0.6852 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6848 Remote Similarity NPD3671 Phase 1
0.6848 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6847 Remote Similarity NPD4632 Approved
0.6842 Remote Similarity NPD7100 Approved
0.6842 Remote Similarity NPD7101 Approved
0.6838 Remote Similarity NPD7492 Approved
0.6814 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6813 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6804 Remote Similarity NPD6098 Approved
0.68 Remote Similarity NPD5281 Approved
0.68 Remote Similarity NPD5284 Approved
0.6783 Remote Similarity NPD6054 Approved
0.6783 Remote Similarity NPD6059 Approved
0.678 Remote Similarity NPD6616 Approved
0.678 Remote Similarity NPD7507 Approved
0.6771 Remote Similarity NPD4197 Approved
0.6768 Remote Similarity NPD6673 Approved
0.6768 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6080 Approved
0.6768 Remote Similarity NPD6904 Approved
0.6759 Remote Similarity NPD6412 Phase 2
0.6754 Remote Similarity NPD6335 Approved
0.6752 Remote Similarity NPD8328 Phase 3
0.6742 Remote Similarity NPD4758 Discontinued
0.6727 Remote Similarity NPD5249 Phase 3
0.6727 Remote Similarity NPD5251 Approved
0.6727 Remote Similarity NPD5247 Approved
0.6727 Remote Similarity NPD5250 Approved
0.6727 Remote Similarity NPD5248 Approved
0.6724 Remote Similarity NPD6909 Approved
0.6724 Remote Similarity NPD6908 Approved
0.6723 Remote Similarity NPD7078 Approved
0.6723 Remote Similarity NPD8293 Discontinued
0.6697 Remote Similarity NPD5168 Approved
0.6667 Remote Similarity NPD5364 Discontinued
0.6667 Remote Similarity NPD3617 Approved
0.6667 Remote Similarity NPD5215 Approved
0.6667 Remote Similarity NPD5216 Approved
0.6667 Remote Similarity NPD6008 Approved
0.6667 Remote Similarity NPD8418 Phase 2
0.6667 Remote Similarity NPD6009 Approved
0.6667 Remote Similarity NPD6317 Approved
0.6667 Remote Similarity NPD5217 Approved
0.6667 Remote Similarity NPD6370 Approved
0.6636 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6633 Remote Similarity NPD4689 Approved
0.6633 Remote Similarity NPD4138 Approved
0.6633 Remote Similarity NPD4693 Phase 3
0.6633 Remote Similarity NPD4688 Approved
0.6633 Remote Similarity NPD4690 Approved
0.6633 Remote Similarity NPD5205 Approved
0.6632 Remote Similarity NPD5369 Approved
0.6609 Remote Similarity NPD6313 Approved
0.6609 Remote Similarity NPD6314 Approved
0.6593 Remote Similarity NPD6926 Approved
0.6593 Remote Similarity NPD6924 Approved
0.6581 Remote Similarity NPD6015 Approved
0.6581 Remote Similarity NPD6016 Approved
0.6577 Remote Similarity NPD5169 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