Structure

Physi-Chem Properties

Molecular Weight:  395.25
Volume:  434.199
LogP:  5.932
LogD:  4.302
LogS:  -6.099
# Rotatable Bonds:  11
TPSA:  38.77
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.281
Synthetic Accessibility Score:  2.636
Fsp3:  0.48
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.956
MDCK Permeability:  2.6476531274965964e-05
Pgp-inhibitor:  0.994
Pgp-substrate:  0.017
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.97
30% Bioavailability (F30%):  0.779

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.136
Plasma Protein Binding (PPB):  98.617431640625%
Volume Distribution (VD):  1.256
Pgp-substrate:  1.259626865386963%

ADMET: Metabolism

CYP1A2-inhibitor:  0.919
CYP1A2-substrate:  0.279
CYP2C19-inhibitor:  0.84
CYP2C19-substrate:  0.239
CYP2C9-inhibitor:  0.41
CYP2C9-substrate:  0.93
CYP2D6-inhibitor:  0.959
CYP2D6-substrate:  0.916
CYP3A4-inhibitor:  0.969
CYP3A4-substrate:  0.199

ADMET: Excretion

Clearance (CL):  6.64
Half-life (T1/2):  0.231

ADMET: Toxicity

hERG Blockers:  0.941
Human Hepatotoxicity (H-HT):  0.603
Drug-inuced Liver Injury (DILI):  0.131
AMES Toxicity:  0.062
Rat Oral Acute Toxicity:  0.047
Maximum Recommended Daily Dose:  0.303
Skin Sensitization:  0.983
Carcinogencity:  0.731
Eye Corrosion:  0.034
Eye Irritation:  0.124
Respiratory Toxicity:  0.966

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

  Natural Product: NPC220923

Natural Product ID:  NPC220923
Common Name*:   Piperchabamide C
IUPAC Name:   (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-1-piperidin-1-yltrideca-2,4,12-trien-1-one
Synonyms:  
Standard InCHIKey:  AVGVCMDFODSDCK-ODWZBEOQSA-N
Standard InCHI:  InChI=1S/C25H33NO3/c27-25(26-18-12-9-13-19-26)15-11-8-6-4-2-1-3-5-7-10-14-22-16-17-23-24(20-22)29-21-28-23/h6,8,10-11,14-17,20H,1-5,7,9,12-13,18-19,21H2/b8-6+,14-10+,15-11+
SMILES:  C(CC/C=C/C=C/C(=O)N1CCCCC1)CCC/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL270620
PubChem CID:   44454018
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000296] Benzodioxoles

*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
NPO10274 Pothomorphe peltata n.a. n.a. n.a. n.a. Dominican Republic n.a. PMID[11430019]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[14695795]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[16872768]
NPO3968 Dracontium loretense Species Araceae Eukaryota corms Iquitos, Peru 2005-MAY PMID[19341262]
NPO3968 Dracontium loretense Species Araceae Eukaryota n.a. n.a. n.a. PMID[19341262]
NPO10666 Verbesina virginica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19485332]
NPO26237 Piper longum Species Piperaceae Eukaryota fruits n.a. n.a. PMID[20839888]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. PMID[22909174]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[23149469]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23434420]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota Fruits n.a. n.a. PMID[23506561]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota leaves n.a. n.a. PMID[25127165]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. PMID[25988621]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12383 Frullania brasiliensis Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27487 Silene banksia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10459 Brickellia longifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9950 Coelogyne nitida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3968 Dracontium loretense Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10274 Pothomorphe peltata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO230 Palisota barteri Species Commelinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9166 Monascus rubropunctatus Species Fellodistomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11511 Cochlearia officinalis Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO876 Didymosphaeria enalia Species Didymosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO43 Leifsonia aquatica Species Microbacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6880 Crocus corsicus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12488 Bupleurum rigidum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23642 Penicillium tardum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2393 Matsumurella chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13059 Abies webbiana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10666 Verbesina virginica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12383 Frullania brasiliensis Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27487 Silene banksia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6428 Euphorbia wangii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8639 Agaricus xanthodermus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7536 Mycoplasma mycoides Species Mycoplasmataceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11137 Dichotomanthes tristaniicarpa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2840 Podocarpus minor Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO964 Homalium laurifolium Species Salicaceae 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
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 42.0 % PMID[522309]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 52.0 % PMID[522309]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 68.0 % PMID[522309]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 9.4 % PMID[522310]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 17.6 % PMID[522310]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = -10.2 % PMID[522310]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = -11.0 % PMID[522310]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 52.0 % PMID[522311]
NPT1460 Cell Line L929 Mus musculus Inhibition = 2.0 % PMID[522311]
NPT1460 Cell Line L929 Mus musculus Inhibition = 25.0 % PMID[522311]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 42.0 % PMID[522311]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 68.0 % PMID[522311]
NPT1460 Cell Line L929 Mus musculus Inhibition = 92.0 % PMID[522311]
NPT993 Cell Line Hepatocyte Mus musculus IC50 = 6700.0 nM PMID[522311]
NPT1460 Cell Line L929 Mus musculus IC50 = 42000.0 nM PMID[522311]
NPT2 Others Unspecified Inhibition = 23.0 % PMID[522311]
NPT2 Others Unspecified Inhibition = 86.0 % PMID[522311]
NPT2 Others Unspecified Inhibition = 9.0 % PMID[522311]
NPT2 Others Unspecified Inhibition = 10.0 % PMID[522311]
NPT2 Others Unspecified IC50 = 42000.0 nM PMID[522311]

☑ 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 NPC220923 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
0.9922 High Similarity NPC99078
0.9846 High Similarity NPC252107
0.9845 High Similarity NPC255817
0.9845 High Similarity NPC277042
0.9845 High Similarity NPC230698
0.9845 High Similarity NPC73883
0.9845 High Similarity NPC251454
0.9845 High Similarity NPC196609
0.9845 High Similarity NPC136330
0.9845 High Similarity NPC205178
0.9767 High Similarity NPC167096
0.9695 High Similarity NPC470707
0.9394 High Similarity NPC96406
0.9323 High Similarity NPC145446
0.9323 High Similarity NPC137172
0.9318 High Similarity NPC94280
0.9318 High Similarity NPC103947
0.9318 High Similarity NPC45783
0.9318 High Similarity NPC159150
0.9318 High Similarity NPC193673
0.9318 High Similarity NPC328419
0.9254 High Similarity NPC95366
0.9254 High Similarity NPC225745
0.9254 High Similarity NPC248505
0.9248 High Similarity NPC180647
0.9167 High Similarity NPC217574
0.9037 High Similarity NPC469808
0.8889 High Similarity NPC471073
0.8889 High Similarity NPC270811
0.8881 High Similarity NPC318862
0.8832 High Similarity NPC28641
0.8832 High Similarity NPC194359
0.8768 High Similarity NPC231572
0.8592 High Similarity NPC244338
0.8531 High Similarity NPC469978
0.8514 High Similarity NPC169742
0.8299 Intermediate Similarity NPC470088
0.8247 Intermediate Similarity NPC231198
0.8227 Intermediate Similarity NPC416184
0.8227 Intermediate Similarity NPC7018
0.82 Intermediate Similarity NPC470708
0.8169 Intermediate Similarity NPC214036
0.8169 Intermediate Similarity NPC113236
0.8121 Intermediate Similarity NPC223125
0.8045 Intermediate Similarity NPC69670
0.8013 Intermediate Similarity NPC223124
0.7987 Intermediate Similarity NPC475959
0.7987 Intermediate Similarity NPC106786
0.7971 Intermediate Similarity NPC218323
0.7955 Intermediate Similarity NPC111225
0.7949 Intermediate Similarity NPC59567
0.7943 Intermediate Similarity NPC118419
0.7941 Intermediate Similarity NPC256167
0.7929 Intermediate Similarity NPC470706
0.7914 Intermediate Similarity NPC291449
0.7914 Intermediate Similarity NPC172403
0.7914 Intermediate Similarity NPC41331
0.7895 Intermediate Similarity NPC212643
0.7895 Intermediate Similarity NPC199209
0.7868 Intermediate Similarity NPC114845
0.7862 Intermediate Similarity NPC241055
0.7842 Intermediate Similarity NPC156944
0.7842 Intermediate Similarity NPC251466
0.7801 Intermediate Similarity NPC160193
0.7786 Intermediate Similarity NPC99798
0.7786 Intermediate Similarity NPC157740
0.7786 Intermediate Similarity NPC64948
0.7786 Intermediate Similarity NPC191302
0.7778 Intermediate Similarity NPC57501
0.7778 Intermediate Similarity NPC148898
0.7778 Intermediate Similarity NPC11147
0.777 Intermediate Similarity NPC207541
0.777 Intermediate Similarity NPC170583
0.777 Intermediate Similarity NPC71105
0.777 Intermediate Similarity NPC246133
0.777 Intermediate Similarity NPC152186
0.777 Intermediate Similarity NPC182147
0.7769 Intermediate Similarity NPC31279
0.773 Intermediate Similarity NPC147247
0.773 Intermediate Similarity NPC246974
0.773 Intermediate Similarity NPC469977
0.7712 Intermediate Similarity NPC119669
0.7708 Intermediate Similarity NPC473463
0.7698 Intermediate Similarity NPC300955
0.7692 Intermediate Similarity NPC127326
0.7677 Intermediate Similarity NPC41178
0.7677 Intermediate Similarity NPC76079
0.7677 Intermediate Similarity NPC78733
0.7677 Intermediate Similarity NPC93593
0.7677 Intermediate Similarity NPC138487
0.7677 Intermediate Similarity NPC216459
0.7673 Intermediate Similarity NPC306669
0.7673 Intermediate Similarity NPC168409
0.7671 Intermediate Similarity NPC193528
0.7667 Intermediate Similarity NPC145304
0.7662 Intermediate Similarity NPC233029
0.7662 Intermediate Similarity NPC210148
0.7643 Intermediate Similarity NPC85830
0.7639 Intermediate Similarity NPC266425
0.7632 Intermediate Similarity NPC37144
0.7632 Intermediate Similarity NPC59907
0.7628 Intermediate Similarity NPC146288
0.7628 Intermediate Similarity NPC31311
0.7628 Intermediate Similarity NPC234392
0.7619 Intermediate Similarity NPC471650
0.7609 Intermediate Similarity NPC193484
0.7605 Intermediate Similarity NPC116007
0.7597 Intermediate Similarity NPC476579
0.7591 Intermediate Similarity NPC344161
0.7586 Intermediate Similarity NPC282477
0.7586 Intermediate Similarity NPC284855
0.7569 Intermediate Similarity NPC477706
0.7568 Intermediate Similarity NPC314682
0.7554 Intermediate Similarity NPC298486
0.7551 Intermediate Similarity NPC254610
0.7534 Intermediate Similarity NPC475828
0.7532 Intermediate Similarity NPC329640
0.7517 Intermediate Similarity NPC213206
0.7517 Intermediate Similarity NPC474915
0.7517 Intermediate Similarity NPC328750
0.7517 Intermediate Similarity NPC188163
0.7515 Intermediate Similarity NPC169387
0.7515 Intermediate Similarity NPC477259
0.75 Intermediate Similarity NPC477694
0.75 Intermediate Similarity NPC83511
0.75 Intermediate Similarity NPC4669
0.75 Intermediate Similarity NPC477705
0.7484 Intermediate Similarity NPC306902
0.7484 Intermediate Similarity NPC215829
0.7484 Intermediate Similarity NPC97072
0.7484 Intermediate Similarity NPC474852
0.7484 Intermediate Similarity NPC477559
0.7484 Intermediate Similarity NPC266753
0.7484 Intermediate Similarity NPC232924
0.7484 Intermediate Similarity NPC8337
0.7484 Intermediate Similarity NPC160298
0.7484 Intermediate Similarity NPC85747
0.7483 Intermediate Similarity NPC167944
0.7483 Intermediate Similarity NPC231884
0.7483 Intermediate Similarity NPC42793
0.7482 Intermediate Similarity NPC301641
0.7482 Intermediate Similarity NPC80241
0.7468 Intermediate Similarity NPC211296
0.7451 Intermediate Similarity NPC95075
0.7451 Intermediate Similarity NPC253883
0.7451 Intermediate Similarity NPC90844
0.7445 Intermediate Similarity NPC277460
0.744 Intermediate Similarity NPC102760
0.7439 Intermediate Similarity NPC67978
0.7439 Intermediate Similarity NPC303581
0.7436 Intermediate Similarity NPC476580
0.7434 Intermediate Similarity NPC130926
0.7426 Intermediate Similarity NPC268317
0.7423 Intermediate Similarity NPC86469
0.7421 Intermediate Similarity NPC118804
0.7421 Intermediate Similarity NPC477080
0.7421 Intermediate Similarity NPC111485
0.7413 Intermediate Similarity NPC286683
0.7407 Intermediate Similarity NPC474858
0.7397 Intermediate Similarity NPC160692
0.7376 Intermediate Similarity NPC249788
0.7375 Intermediate Similarity NPC135006
0.7372 Intermediate Similarity NPC120075
0.7372 Intermediate Similarity NPC280001
0.7372 Intermediate Similarity NPC185738
0.7368 Intermediate Similarity NPC179309
0.7365 Intermediate Similarity NPC131204
0.7365 Intermediate Similarity NPC301050
0.7365 Intermediate Similarity NPC307682
0.7362 Intermediate Similarity NPC474324
0.7362 Intermediate Similarity NPC57812
0.7355 Intermediate Similarity NPC469540
0.7355 Intermediate Similarity NPC219162
0.7355 Intermediate Similarity NPC469539
0.7351 Intermediate Similarity NPC138438
0.7351 Intermediate Similarity NPC908
0.7349 Intermediate Similarity NPC308267
0.7349 Intermediate Similarity NPC181905
0.7346 Intermediate Similarity NPC232514
0.7346 Intermediate Similarity NPC276944
0.7346 Intermediate Similarity NPC238530
0.7346 Intermediate Similarity NPC225774
0.7343 Intermediate Similarity NPC301713
0.7321 Intermediate Similarity NPC27887
0.732 Intermediate Similarity NPC185838
0.7317 Intermediate Similarity NPC473748
0.7317 Intermediate Similarity NPC475845
0.7315 Intermediate Similarity NPC230968
0.7315 Intermediate Similarity NPC102260
0.7315 Intermediate Similarity NPC253429
0.731 Intermediate Similarity NPC476748
0.7303 Intermediate Similarity NPC136860
0.7303 Intermediate Similarity NPC476567
0.7303 Intermediate Similarity NPC128019
0.7301 Intermediate Similarity NPC329717
0.7301 Intermediate Similarity NPC476432
0.7301 Intermediate Similarity NPC219341
0.7301 Intermediate Similarity NPC24264
0.7296 Intermediate Similarity NPC57512
0.7286 Intermediate Similarity NPC471877

  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 NPC220923 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
0.9845 High Similarity NPD2492 Phase 1
0.8345 Intermediate Similarity NPD5297 Approved
0.8027 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5718 Phase 2
0.7857 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD7110 Phase 1
0.7582 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD3885 Approved
0.7552 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD824 Approved
0.7483 Intermediate Similarity NPD6895 Approved
0.7483 Intermediate Similarity NPD6896 Approved
0.7468 Intermediate Similarity NPD5978 Approved
0.7468 Intermediate Similarity NPD5977 Approved
0.7452 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD4210 Discontinued
0.7389 Intermediate Similarity NPD6385 Approved
0.7389 Intermediate Similarity NPD6873 Phase 2
0.7389 Intermediate Similarity NPD6386 Approved
0.7381 Intermediate Similarity NPD7280 Phase 3
0.7381 Intermediate Similarity NPD7281 Phase 3
0.7375 Intermediate Similarity NPD5604 Discontinued
0.7372 Intermediate Similarity NPD5536 Phase 2
0.7351 Intermediate Similarity NPD4237 Approved
0.7351 Intermediate Similarity NPD4236 Phase 3
0.7338 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD6875 Approved
0.7325 Intermediate Similarity NPD6876 Approved
0.7301 Intermediate Similarity NPD4166 Phase 2
0.7297 Intermediate Similarity NPD2653 Approved
0.7279 Intermediate Similarity NPD3142 Approved
0.7279 Intermediate Similarity NPD3140 Approved
0.7266 Intermediate Similarity NPD1357 Approved
0.7254 Intermediate Similarity NPD1421 Approved
0.7254 Intermediate Similarity NPD1420 Approved
0.7248 Intermediate Similarity NPD6111 Discontinued
0.7248 Intermediate Similarity NPD743 Approved
0.7244 Intermediate Similarity NPD3639 Approved
0.7244 Intermediate Similarity NPD3641 Approved
0.7244 Intermediate Similarity NPD3640 Phase 3
0.7234 Intermediate Similarity NPD3705 Approved
0.7226 Intermediate Similarity NPD4584 Approved
0.7226 Intermediate Similarity NPD3146 Approved
0.7226 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD5457 Discontinued
0.7188 Intermediate Similarity NPD2977 Approved
0.7188 Intermediate Similarity NPD2978 Approved
0.7143 Intermediate Similarity NPD6382 Discontinued
0.7135 Intermediate Similarity NPD6618 Phase 2
0.7124 Intermediate Similarity NPD5177 Phase 3
0.7108 Intermediate Similarity NPD2898 Approved
0.7105 Intermediate Similarity NPD3656 Approved
0.7097 Intermediate Similarity NPD7124 Phase 2
0.7095 Intermediate Similarity NPD3530 Approved
0.7095 Intermediate Similarity NPD2674 Phase 3
0.7095 Intermediate Similarity NPD3531 Approved
0.7095 Intermediate Similarity NPD3532 Approved
0.7095 Intermediate Similarity NPD2245 Discovery
0.7092 Intermediate Similarity NPD2667 Approved
0.7092 Intermediate Similarity NPD2668 Approved
0.7088 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5313 Approved
0.7083 Intermediate Similarity NPD5312 Approved
0.708 Intermediate Similarity NPD5283 Phase 1
0.7067 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4357 Discontinued
0.7044 Intermediate Similarity NPD4017 Approved
0.7039 Intermediate Similarity NPD1725 Approved
0.7037 Intermediate Similarity NPD5353 Approved
0.7032 Intermediate Similarity NPD2219 Phase 1
0.7032 Intermediate Similarity NPD5241 Discontinued
0.7027 Intermediate Similarity NPD3144 Approved
0.7027 Intermediate Similarity NPD3145 Approved
0.7025 Intermediate Similarity NPD6031 Approved
0.7025 Intermediate Similarity NPD6030 Approved
0.702 Intermediate Similarity NPD7119 Phase 2
0.7014 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD3060 Approved
0.7013 Intermediate Similarity NPD4162 Approved
0.7011 Intermediate Similarity NPD3349 Phase 2
0.7011 Intermediate Similarity NPD7291 Discontinued
0.7006 Intermediate Similarity NPD1424 Approved
0.7 Intermediate Similarity NPD6297 Approved
0.6993 Remote Similarity NPD1375 Discontinued
0.6986 Remote Similarity NPD7905 Discontinued
0.6975 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6975 Remote Similarity NPD5773 Approved
0.6975 Remote Similarity NPD5772 Approved
0.6968 Remote Similarity NPD5481 Discontinued
0.6957 Remote Similarity NPD4773 Phase 2
0.6957 Remote Similarity NPD4772 Phase 2
0.6948 Remote Similarity NPD1044 Clinical (unspecified phase)
0.6948 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6944 Remote Similarity NPD2232 Approved
0.6944 Remote Similarity NPD2233 Approved
0.6944 Remote Similarity NPD2230 Approved
0.6937 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6936 Remote Similarity NPD6853 Approved
0.6936 Remote Similarity NPD6851 Approved
0.6933 Remote Similarity NPD3109 Approved
0.6933 Remote Similarity NPD3110 Approved
0.6928 Remote Similarity NPD6107 Approved
0.6923 Remote Similarity NPD3447 Discontinued
0.6923 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1670 Discontinued
0.6918 Remote Similarity NPD2122 Discontinued
0.6918 Remote Similarity NPD4727 Phase 1
0.6914 Remote Similarity NPD3383 Approved
0.6914 Remote Similarity NPD3382 Approved
0.6914 Remote Similarity NPD7298 Approved
0.6914 Remote Similarity NPD3384 Approved
0.6913 Remote Similarity NPD3374 Clinical (unspecified phase)
0.691 Remote Similarity NPD6493 Phase 3
0.6905 Remote Similarity NPD4481 Phase 3
0.6899 Remote Similarity NPD4739 Approved
0.6889 Remote Similarity NPD1358 Approved
0.6886 Remote Similarity NPD6071 Discontinued
0.6879 Remote Similarity NPD5295 Discontinued
0.6879 Remote Similarity NPD2120 Phase 2
0.6875 Remote Similarity NPD4124 Clinical (unspecified phase)
0.6872 Remote Similarity NPD5582 Discontinued
0.6871 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6867 Remote Similarity NPD5677 Discontinued
0.6859 Remote Similarity NPD5754 Discontinued
0.6855 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6849 Remote Similarity NPD2922 Phase 1
0.6846 Remote Similarity NPD5746 Approved
0.6839 Remote Similarity NPD7153 Discontinued
0.6836 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6829 Remote Similarity NPD2560 Approved
0.6829 Remote Similarity NPD2563 Approved
0.6824 Remote Similarity NPD2040 Clinical (unspecified phase)
0.6818 Remote Similarity NPD2161 Phase 2
0.6815 Remote Similarity NPD3134 Approved
0.6813 Remote Similarity NPD5976 Discontinued
0.6813 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6812 Remote Similarity NPD228 Approved
0.6809 Remote Similarity NPD3596 Phase 2
0.6803 Remote Similarity NPD4098 Discontinued
0.68 Remote Similarity NPD1336 Approved
0.6796 Remote Similarity NPD4420 Approved
0.6792 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6788 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6788 Remote Similarity NPD6788 Approved
0.6783 Remote Similarity NPD2595 Approved
0.6783 Remote Similarity NPD2594 Approved
0.678 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6772 Remote Similarity NPD160 Clinical (unspecified phase)
0.677 Remote Similarity NPD3687 Approved
0.677 Remote Similarity NPD3686 Approved
0.6768 Remote Similarity NPD4585 Approved
0.6766 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6766 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6757 Remote Similarity NPD7018 Phase 2
0.6755 Remote Similarity NPD5745 Approved
0.6753 Remote Similarity NPD4108 Discontinued
0.6752 Remote Similarity NPD6331 Phase 2
0.6752 Remote Similarity NPD6658 Clinical (unspecified phase)
0.675 Remote Similarity NPD7314 Clinical (unspecified phase)
0.675 Remote Similarity NPD1975 Clinical (unspecified phase)
0.6747 Remote Similarity NPD8031 Discontinued
0.6747 Remote Similarity NPD7833 Phase 2
0.6747 Remote Similarity NPD7831 Phase 2
0.6747 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6747 Remote Similarity NPD1309 Phase 2
0.6747 Remote Similarity NPD1307 Phase 2
0.6746 Remote Similarity NPD2388 Discontinued
0.6746 Remote Similarity NPD5242 Approved
0.6743 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5163 Phase 2
0.6728 Remote Similarity NPD3866 Clinical (unspecified phase)
0.6727 Remote Similarity NPD5967 Approved
0.6726 Remote Similarity NPD7802 Discontinued
0.6724 Remote Similarity NPD7549 Discontinued
0.6713 Remote Similarity NPD2486 Discontinued
0.6707 Remote Similarity NPD7248 Discontinued
0.669 Remote Similarity NPD3294 Phase 2
0.6689 Remote Similarity NPD1039 Discontinued
0.6689 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6687 Remote Similarity NPD2335 Discontinued
0.6687 Remote Similarity NPD2592 Discontinued
0.6687 Remote Similarity NPD4123 Phase 3
0.6686 Remote Similarity NPD3051 Approved
0.6685 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7201 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4084 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1669 Approved
0.6667 Remote Similarity NPD6830 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