Structure

Physi-Chem Properties

Molecular Weight:  218.17
Volume:  257.684
LogP:  5.381
LogD:  4.327
LogS:  -4.555
# Rotatable Bonds:  4
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.735
Synthetic Accessibility Score:  2.787
Fsp3:  0.467
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:  -4.572
MDCK Permeability:  1.9522673028404824e-05
Pgp-inhibitor:  0.806
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.994
30% Bioavailability (F30%):  0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.281
Plasma Protein Binding (PPB):  98.25858306884766%
Volume Distribution (VD):  6.858
Pgp-substrate:  4.162252902984619%

ADMET: Metabolism

CYP1A2-inhibitor:  0.966
CYP1A2-substrate:  0.891
CYP2C19-inhibitor:  0.912
CYP2C19-substrate:  0.777
CYP2C9-inhibitor:  0.749
CYP2C9-substrate:  0.939
CYP2D6-inhibitor:  0.753
CYP2D6-substrate:  0.805
CYP3A4-inhibitor:  0.485
CYP3A4-substrate:  0.387

ADMET: Excretion

Clearance (CL):  16.064
Half-life (T1/2):  0.178

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.722
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.033
Rat Oral Acute Toxicity:  0.058
Maximum Recommended Daily Dose:  0.906
Skin Sensitization:  0.59
Carcinogencity:  0.245
Eye Corrosion:  0.449
Eye Irritation:  0.978
Respiratory Toxicity:  0.769

Download Data

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

  Natural Product: NPC6597

Natural Product ID:  NPC6597
Common Name*:   (+)-Curcuphenol
IUPAC Name:   5-methyl-2-[(2S)-6-methylhept-5-en-2-yl]phenol
Synonyms:   (+)-Curcuphenol; (1S)-(+)-Curcuphenol; (S)-(+)-Curcuphenol
Standard InCHIKey:  BTXSROVNGICYFE-ZDUSSCGKSA-N
Standard InCHI:  InChI=1S/C15H22O/c1-11(2)6-5-7-13(4)14-9-8-12(3)10-15(14)16/h6,8-10,13,16H,5,7H2,1-4H3/t13-/m0/s1
SMILES:  CC(=CCC[C@H](C)c1ccc(C)cc1O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL451860
PubChem CID:   156118
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO40764 Parahigginsia sp. Species n.a. n.a. n.a. n.a. n.a. PMID[10217711]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12350137]
NPO26494 Didiscus oxeata Species Halichondriidae Eukaryota n.a. Rio Bueno, Jamaica n.a. PMID[12444675]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota rhizome n.a. n.a. PMID[12617587]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[23153397]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. leaf n.a. PMID[23901173]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[28068085]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9584408]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome Essent. Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26494 Didiscus oxeata Species Halichondriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24124 Curcuma longa Species Zingiberaceae 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
NPT168 Cell Line P388 Mus musculus IC50 = 7.0 ug.mL-1 PMID[531406]
NPT81 Cell Line A549 Homo sapiens MIC = 10.0 ug.mL-1 PMID[531406]
NPT180 Cell Line HCT-8 Homo sapiens MIC = 0.1 ug.mL-1 PMID[531406]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 209000.0 nM PMID[531407]
NPT168 Cell Line P388 Mus musculus IC50 = 0.1 ug.mL-1 PMID[531409]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 8.1 ug.mL-1 PMID[531409]
NPT36 Individual Protein Tyrosine-protein kinase SRC Homo sapiens IC50 = 35800.0 nM PMID[531410]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI > 20.0 % PMID[531410]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 20000.0 nM PMID[531410]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 37200.0 nM PMID[531410]
NPT784 Cell Line MDA-MB-468 Homo sapiens Activity = 95.65 % PMID[531410]
NPT396 Cell Line T47D Homo sapiens Activity = 110.61 % PMID[531410]
NPT457 Cell Line BT-549 Homo sapiens Activity = 114.49 % PMID[531410]
NPT82 Cell Line MDA-MB-231 Homo sapiens Activity = 97.07 % PMID[531410]
NPT83 Cell Line MCF7 Homo sapiens Activity = 97.84 % PMID[531410]
NPT384 Cell Line TK-10 Homo sapiens Activity = 109.99 % PMID[531410]
NPT368 Cell Line SN12C Homo sapiens Activity = 104.83 % PMID[531410]
NPT406 Cell Line RXF 393 Homo sapiens Activity = 103.08 % PMID[531410]
NPT308 Cell Line CAKI-1 Homo sapiens Activity = 107.0 % PMID[531410]
NPT369 Cell Line ACHN Homo sapiens Activity = 109.35 % PMID[531410]
NPT376 Cell Line A498 Homo sapiens Activity = 87.85 % PMID[531410]
NPT401 Cell Line 786-0 Homo sapiens Activity = 79.88 % PMID[531410]
NPT458 Cell Line IGROV-1 Homo sapiens Activity = 97.76 % PMID[531410]
NPT373 Cell Line SK-MEL-5 Homo sapiens Activity = 97.46 % PMID[531410]
NPT170 Cell Line SK-MEL-28 Homo sapiens Activity = 119.18 % PMID[531410]
NPT147 Cell Line SK-MEL-2 Homo sapiens Activity = 147.33 % PMID[531410]
NPT400 Cell Line MDA-MB-435 Homo sapiens Activity = 100.32 % PMID[531410]
NPT387 Cell Line M14 Homo sapiens Activity = 106.0 % PMID[531410]
NPT375 Cell Line Malme-3M Homo sapiens Activity = 114.51 % PMID[531410]
NPT390 Cell Line LOX IMVI Homo sapiens Activity = 107.4 % PMID[531410]
NPT380 Cell Line U-251 Homo sapiens Activity = 102.89 % PMID[531410]
NPT392 Cell Line SNB-75 Homo sapiens Activity = 94.35 % PMID[531410]
NPT383 Cell Line SNB-19 Homo sapiens Activity = 98.46 % PMID[531410]
NPT374 Cell Line SF-539 Homo sapiens Activity = 103.29 % PMID[531410]
NPT399 Cell Line SF-295 Homo sapiens Activity = 106.62 % PMID[531410]
NPT323 Cell Line SW-620 Homo sapiens Activity = 113.87 % PMID[531410]
NPT386 Cell Line KM12 Homo sapiens Activity = 93.79 % PMID[531410]
NPT139 Cell Line HT-29 Homo sapiens Activity = 102.73 % PMID[531410]
NPT391 Cell Line HCC 2998 Homo sapiens Activity = 99.54 % PMID[531410]
NPT407 Cell Line COLO 205 Homo sapiens Activity = 116.6 % PMID[531410]
NPT455 Cell Line NCI-H522 Homo sapiens Activity = 100.89 % PMID[531410]
NPT397 Cell Line NCI-H460 Homo sapiens Activity = 106.79 % PMID[531410]
NPT388 Cell Line NCI-H322M Homo sapiens Activity = 112.83 % PMID[531410]
NPT370 Cell Line NCI-H23 Homo sapiens Activity = 94.86 % PMID[531410]
NPT405 Cell Line NCI-H226 Homo sapiens Activity = 106.52 % PMID[531410]
NPT372 Cell Line HOP-92 Homo sapiens Activity = 84.95 % PMID[531410]
NPT379 Cell Line HOP-62 Homo sapiens Activity = 102.09 % PMID[531410]
NPT81 Cell Line A549 Homo sapiens Activity = 92.59 % PMID[531410]
NPT389 Cell Line RPMI-8226 Homo sapiens Activity = 99.89 % PMID[531410]
NPT112 Cell Line MOLT-4 Homo sapiens Activity = 102.06 % PMID[531410]
NPT111 Cell Line K562 Homo sapiens Activity = 93.03 % PMID[531410]
NPT116 Cell Line HL-60 Homo sapiens Activity = 85.65 % PMID[531410]
NPT404 Cell Line CCRF-CEM Homo sapiens Activity = 104.92 % PMID[531410]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 20000.0 nM PMID[531410]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 50000.0 nM PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 0.1 ug.mL-1 PMID[531406]
NPT20 Organism Candida albicans Candida albicans MIC = 8.0 ug.mL-1 PMID[531406]
NPT20 Organism Candida albicans Candida albicans MIC = 7.5 ug.mL-1 PMID[531408]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 7.5 ug.mL-1 PMID[531408]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 7.5 ug.mL-1 PMID[531408]
NPT20 Organism Candida albicans Candida albicans MFC = 12.5 ug ml-1 PMID[531408]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MFC = 12.5 ug ml-1 PMID[531408]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 12.5 ug ml-1 PMID[531408]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum MIC = 3.6 ug.mL-1 PMID[531408]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum MIC = 1.8 ug.mL-1 PMID[531408]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 8.3 ug.mL-1 PMID[531409]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 114.35 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 80.0 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 83.0 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 118.93 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 98.97 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 108.08 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 100.35 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 96.28 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 99.98 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 107.12 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 109.18 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 97.29 % PMID[531410]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 109.82 % PMID[531410]

☑ 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 NPC6597 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 NPC79241
0.989 High Similarity NPC312132
0.989 High Similarity NPC259512
0.9785 High Similarity NPC72729
0.9677 High Similarity NPC33675
0.9677 High Similarity NPC299762
0.9479 High Similarity NPC475225
0.9474 High Similarity NPC252105
0.9451 High Similarity NPC231150
0.9375 High Similarity NPC471228
0.9375 High Similarity NPC235762
0.9247 High Similarity NPC245187
0.9247 High Similarity NPC152415
0.9192 High Similarity NPC66834
0.9184 High Similarity NPC117115
0.9184 High Similarity NPC47284
0.9167 High Similarity NPC174911
0.9158 High Similarity NPC77492
0.914 High Similarity NPC3358
0.914 High Similarity NPC162314
0.914 High Similarity NPC306884
0.914 High Similarity NPC147284
0.914 High Similarity NPC94139
0.914 High Similarity NPC210497
0.914 High Similarity NPC55903
0.913 High Similarity NPC192
0.9121 High Similarity NPC27974
0.91 High Similarity NPC64586
0.9091 High Similarity NPC21594
0.9091 High Similarity NPC53740
0.9091 High Similarity NPC310456
0.9072 High Similarity NPC477685
0.9032 High Similarity NPC306074
0.9032 High Similarity NPC304541
0.9011 High Similarity NPC407
0.9011 High Similarity NPC307235
0.901 High Similarity NPC58865
0.9 High Similarity NPC151477
0.8969 High Similarity NPC48730
0.8969 High Similarity NPC248396
0.8969 High Similarity NPC129373
0.8958 High Similarity NPC152097
0.8947 High Similarity NPC8392
0.8947 High Similarity NPC222146
0.8911 High Similarity NPC306295
0.8901 High Similarity NPC155393
0.8889 High Similarity NPC238696
0.8889 High Similarity NPC218879
0.8889 High Similarity NPC475580
0.8889 High Similarity NPC244513
0.8889 High Similarity NPC227458
0.8889 High Similarity NPC272029
0.8878 High Similarity NPC80800
0.8878 High Similarity NPC12221
0.8866 High Similarity NPC122005
0.8866 High Similarity NPC260775
0.8866 High Similarity NPC252821
0.8842 High Similarity NPC316301
0.8842 High Similarity NPC27323
0.8842 High Similarity NPC289769
0.8842 High Similarity NPC76938
0.8835 High Similarity NPC224527
0.8824 High Similarity NPC299568
0.8824 High Similarity NPC186385
0.8817 High Similarity NPC318325
0.8817 High Similarity NPC242240
0.8817 High Similarity NPC123273
0.8817 High Similarity NPC258219
0.8812 High Similarity NPC232523
0.8812 High Similarity NPC320439
0.8812 High Similarity NPC204901
0.8812 High Similarity NPC158253
0.88 High Similarity NPC37802
0.8791 High Similarity NPC150837
0.8791 High Similarity NPC286904
0.8788 High Similarity NPC269212
0.8788 High Similarity NPC108497
0.8776 High Similarity NPC70677
0.8776 High Similarity NPC130756
0.8776 High Similarity NPC12931
0.8776 High Similarity NPC225506
0.8763 High Similarity NPC156313
0.8763 High Similarity NPC474073
0.8763 High Similarity NPC475078
0.875 High Similarity NPC250323
0.875 High Similarity NPC228452
0.875 High Similarity NPC32714
0.8738 High Similarity NPC132720
0.8737 High Similarity NPC29373
0.8737 High Similarity NPC271440
0.8725 High Similarity NPC174981
0.8713 High Similarity NPC12640
0.8713 High Similarity NPC99836
0.8713 High Similarity NPC201662
0.871 High Similarity NPC19680
0.871 High Similarity NPC25493
0.871 High Similarity NPC113460
0.8667 High Similarity NPC715
0.8654 High Similarity NPC260323
0.8654 High Similarity NPC266937
0.8654 High Similarity NPC470770
0.8654 High Similarity NPC176279
0.8654 High Similarity NPC77772
0.8654 High Similarity NPC469912
0.8654 High Similarity NPC151537
0.8654 High Similarity NPC54373
0.8641 High Similarity NPC19808
0.8641 High Similarity NPC33728
0.8632 High Similarity NPC204210
0.8632 High Similarity NPC155908
0.8617 High Similarity NPC177420
0.8617 High Similarity NPC280347
0.8602 High Similarity NPC23167
0.86 High Similarity NPC24327
0.86 High Similarity NPC12870
0.8586 High Similarity NPC211885
0.8585 High Similarity NPC195922
0.8571 High Similarity NPC46940
0.8571 High Similarity NPC177962
0.8571 High Similarity NPC225464
0.8571 High Similarity NPC302371
0.8571 High Similarity NPC26615
0.8571 High Similarity NPC62867
0.8558 High Similarity NPC13482
0.8558 High Similarity NPC141782
0.8557 High Similarity NPC144682
0.8557 High Similarity NPC274678
0.8544 High Similarity NPC11554
0.8529 High Similarity NPC469913
0.8529 High Similarity NPC155072
0.8529 High Similarity NPC271274
0.8526 High Similarity NPC55561
0.8515 High Similarity NPC323810
0.8505 High Similarity NPC84999
0.8505 High Similarity NPC246760
0.85 High Similarity NPC51015
0.8495 Intermediate Similarity NPC197783
0.8491 Intermediate Similarity NPC319803
0.8491 Intermediate Similarity NPC190212
0.8491 Intermediate Similarity NPC23804
0.8485 Intermediate Similarity NPC92730
0.8485 Intermediate Similarity NPC128723
0.8478 Intermediate Similarity NPC474354
0.8476 Intermediate Similarity NPC95716
0.8469 Intermediate Similarity NPC132271
0.8469 Intermediate Similarity NPC292730
0.8469 Intermediate Similarity NPC216520
0.8469 Intermediate Similarity NPC473388
0.8469 Intermediate Similarity NPC202986
0.8469 Intermediate Similarity NPC82664
0.8462 Intermediate Similarity NPC314187
0.8454 Intermediate Similarity NPC128062
0.8447 Intermediate Similarity NPC474352
0.8431 Intermediate Similarity NPC471350
0.8431 Intermediate Similarity NPC138942
0.8421 Intermediate Similarity NPC70436
0.8416 Intermediate Similarity NPC24404
0.8416 Intermediate Similarity NPC168829
0.8416 Intermediate Similarity NPC313030
0.8416 Intermediate Similarity NPC106396
0.8416 Intermediate Similarity NPC168393
0.8416 Intermediate Similarity NPC71002
0.8416 Intermediate Similarity NPC242342
0.8416 Intermediate Similarity NPC302219
0.8416 Intermediate Similarity NPC222522
0.8416 Intermediate Similarity NPC249828
0.8416 Intermediate Similarity NPC146798
0.8416 Intermediate Similarity NPC85479
0.8416 Intermediate Similarity NPC53051
0.8416 Intermediate Similarity NPC94351
0.8416 Intermediate Similarity NPC168303
0.8416 Intermediate Similarity NPC233827
0.8404 Intermediate Similarity NPC184169
0.84 Intermediate Similarity NPC10588
0.84 Intermediate Similarity NPC130103
0.84 Intermediate Similarity NPC294741
0.84 Intermediate Similarity NPC166761
0.8396 Intermediate Similarity NPC471179
0.8396 Intermediate Similarity NPC166995
0.8387 Intermediate Similarity NPC248817
0.8387 Intermediate Similarity NPC175313
0.8387 Intermediate Similarity NPC474211
0.8384 Intermediate Similarity NPC32674
0.8381 Intermediate Similarity NPC224870
0.8381 Intermediate Similarity NPC296683
0.837 Intermediate Similarity NPC168855
0.8367 Intermediate Similarity NPC26244
0.835 Intermediate Similarity NPC477814
0.835 Intermediate Similarity NPC54765
0.8349 Intermediate Similarity NPC477136
0.8333 Intermediate Similarity NPC469719
0.8333 Intermediate Similarity NPC192948
0.8333 Intermediate Similarity NPC288411
0.8333 Intermediate Similarity NPC120719
0.8333 Intermediate Similarity NPC102216
0.8333 Intermediate Similarity NPC35797
0.8333 Intermediate Similarity NPC312304
0.8318 Intermediate Similarity NPC117846
0.8318 Intermediate Similarity NPC263753
0.8317 Intermediate Similarity NPC192032

  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 NPC6597 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
0.989 High Similarity NPD288 Approved
0.978 High Similarity NPD844 Approved
0.914 High Similarity NPD845 Approved
0.8969 High Similarity NPD289 Clinical (unspecified phase)
0.8842 High Similarity NPD1432 Clinical (unspecified phase)
0.8824 High Similarity NPD4750 Phase 3
0.8673 High Similarity NPD3020 Approved
0.8571 High Similarity NPD7635 Approved
0.8557 High Similarity NPD1809 Phase 2
0.8529 High Similarity NPD1444 Approved
0.8529 High Similarity NPD1445 Approved
0.8447 Intermediate Similarity NPD2342 Discontinued
0.8367 Intermediate Similarity NPD2859 Approved
0.8367 Intermediate Similarity NPD2860 Approved
0.8317 Intermediate Similarity NPD940 Approved
0.8317 Intermediate Similarity NPD846 Approved
0.8286 Intermediate Similarity NPD3021 Approved
0.8286 Intermediate Similarity NPD1792 Phase 2
0.8286 Intermediate Similarity NPD3022 Approved
0.828 Intermediate Similarity NPD111 Approved
0.8265 Intermediate Similarity NPD2933 Approved
0.8265 Intermediate Similarity NPD2934 Approved
0.7838 Intermediate Similarity NPD6671 Approved
0.7788 Intermediate Similarity NPD3091 Approved
0.7748 Intermediate Similarity NPD1791 Approved
0.7748 Intermediate Similarity NPD1793 Approved
0.7714 Intermediate Similarity NPD9500 Approved
0.7692 Intermediate Similarity NPD4749 Approved
0.7692 Intermediate Similarity NPD1242 Phase 1
0.7658 Intermediate Similarity NPD2228 Approved
0.7658 Intermediate Similarity NPD2229 Approved
0.7658 Intermediate Similarity NPD2234 Approved
0.7652 Intermediate Similarity NPD3019 Approved
0.7652 Intermediate Similarity NPD2932 Approved
0.7652 Intermediate Similarity NPD4626 Approved
0.7652 Intermediate Similarity NPD1751 Approved
0.7652 Intermediate Similarity NPD4059 Approved
0.7632 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD497 Approved
0.7565 Intermediate Similarity NPD4093 Discontinued
0.7542 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7521 Intermediate Similarity NPD3092 Approved
0.75 Intermediate Similarity NPD9273 Approved
0.75 Intermediate Similarity NPD495 Approved
0.75 Intermediate Similarity NPD498 Approved
0.75 Intermediate Similarity NPD496 Approved
0.7478 Intermediate Similarity NPD5304 Approved
0.7478 Intermediate Similarity NPD5303 Approved
0.7477 Intermediate Similarity NPD228 Approved
0.7477 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD9610 Approved
0.7477 Intermediate Similarity NPD9608 Approved
0.7473 Intermediate Similarity NPD9087 Approved
0.7434 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7373 Intermediate Similarity NPD1201 Approved
0.7373 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7373 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.735 Intermediate Similarity NPD2286 Discontinued
0.735 Intermediate Similarity NPD3095 Discontinued
0.735 Intermediate Similarity NPD4589 Approved
0.7345 Intermediate Similarity NPD1398 Phase 1
0.7345 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6696 Suspended
0.7317 Intermediate Similarity NPD4625 Phase 3
0.7311 Intermediate Similarity NPD2233 Approved
0.7311 Intermediate Similarity NPD2230 Approved
0.7311 Intermediate Similarity NPD2232 Approved
0.7304 Intermediate Similarity NPD7340 Approved
0.7304 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD1983 Approved
0.7288 Intermediate Similarity NPD1980 Approved
0.7288 Intermediate Similarity NPD1981 Approved
0.7281 Intermediate Similarity NPD9618 Approved
0.7281 Intermediate Similarity NPD9614 Approved
0.7273 Intermediate Similarity NPD3094 Phase 2
0.7265 Intermediate Similarity NPD5691 Approved
0.7258 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD9379 Approved
0.7257 Intermediate Similarity NPD9377 Approved
0.7234 Intermediate Similarity NPD9294 Approved
0.7217 Intermediate Similarity NPD709 Approved
0.7213 Intermediate Similarity NPD2194 Approved
0.7213 Intermediate Similarity NPD2195 Approved
0.7203 Intermediate Similarity NPD1778 Approved
0.7196 Intermediate Similarity NPD1616 Discontinued
0.7196 Intermediate Similarity NPD3028 Approved
0.7193 Intermediate Similarity NPD5283 Phase 1
0.7158 Intermediate Similarity NPD9088 Approved
0.7154 Intermediate Similarity NPD5736 Approved
0.7154 Intermediate Similarity NPD3636 Approved
0.7154 Intermediate Similarity NPD3637 Approved
0.7154 Intermediate Similarity NPD3635 Approved
0.7154 Intermediate Similarity NPD2861 Phase 2
0.7131 Intermediate Similarity NPD1470 Approved
0.713 Intermediate Similarity NPD475 Phase 2
0.7129 Intermediate Similarity NPD1101 Approved
0.7117 Intermediate Similarity NPD290 Approved
0.7107 Intermediate Similarity NPD1755 Approved
0.7105 Intermediate Similarity NPD1138 Approved
0.7097 Intermediate Similarity NPD2605 Approved
0.7097 Intermediate Similarity NPD2606 Approved
0.7094 Intermediate Similarity NPD9615 Approved
0.7094 Intermediate Similarity NPD9613 Approved
0.7094 Intermediate Similarity NPD9616 Approved
0.7083 Intermediate Similarity NPD1610 Phase 2
0.7054 Intermediate Similarity NPD2684 Approved
0.7049 Intermediate Similarity NPD1283 Approved
0.704 Intermediate Similarity NPD5156 Approved
0.704 Intermediate Similarity NPD5155 Approved
0.7034 Intermediate Similarity NPD7330 Discontinued
0.7034 Intermediate Similarity NPD316 Approved
0.7031 Intermediate Similarity NPD4097 Suspended
0.7027 Intermediate Similarity NPD968 Approved
0.7018 Intermediate Similarity NPD1137 Approved
0.7018 Intermediate Similarity NPD1139 Approved
0.7016 Intermediate Similarity NPD1712 Approved
0.7008 Intermediate Similarity NPD4060 Phase 1
0.7 Intermediate Similarity NPD3023 Approved
0.7 Intermediate Similarity NPD3026 Approved
0.7 Intermediate Similarity NPD3496 Discontinued
0.6992 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6991 Remote Similarity NPD9380 Clinical (unspecified phase)
0.699 Remote Similarity NPD1089 Approved
0.699 Remote Similarity NPD1090 Approved
0.699 Remote Similarity NPD1086 Approved
0.6975 Remote Similarity NPD3025 Approved
0.6975 Remote Similarity NPD1651 Approved
0.6975 Remote Similarity NPD3024 Approved
0.6975 Remote Similarity NPD4235 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6972 Remote Similarity NPD4818 Approved
0.6972 Remote Similarity NPD4817 Approved
0.696 Remote Similarity NPD3595 Approved
0.696 Remote Similarity NPD3594 Approved
0.696 Remote Similarity NPD4908 Phase 1
0.6942 Remote Similarity NPD1611 Approved
0.6935 Remote Similarity NPD4624 Approved
0.693 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6929 Remote Similarity NPD6663 Approved
0.6923 Remote Similarity NPD7157 Approved
0.6923 Remote Similarity NPD256 Approved
0.6923 Remote Similarity NPD255 Approved
0.6917 Remote Similarity NPD2667 Approved
0.6917 Remote Similarity NPD2668 Approved
0.6917 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6903 Remote Similarity NPD9266 Approved
0.6903 Remote Similarity NPD74 Approved
0.6893 Remote Similarity NPD800 Approved
0.6891 Remote Similarity NPD1759 Phase 1
0.6887 Remote Similarity NPD1693 Approved
0.6885 Remote Similarity NPD1608 Approved
0.687 Remote Similarity NPD6099 Approved
0.687 Remote Similarity NPD6100 Approved
0.6869 Remote Similarity NPD9089 Approved
0.6864 Remote Similarity NPD7636 Approved
0.6864 Remote Similarity NPD9493 Approved
0.686 Remote Similarity NPD2688 Clinical (unspecified phase)
0.686 Remote Similarity NPD3143 Discontinued
0.6857 Remote Similarity NPD1088 Approved
0.6855 Remote Similarity NPD2797 Approved
0.685 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6847 Remote Similarity NPD9244 Approved
0.6846 Remote Similarity NPD7718 Clinical (unspecified phase)
0.6814 Remote Similarity NPD9263 Approved
0.6814 Remote Similarity NPD9264 Approved
0.6814 Remote Similarity NPD9267 Approved
0.681 Remote Similarity NPD821 Approved
0.681 Remote Similarity NPD7843 Approved
0.6807 Remote Similarity NPD16 Approved
0.6807 Remote Similarity NPD856 Approved
0.6807 Remote Similarity NPD1758 Phase 1
0.6803 Remote Similarity NPD1281 Approved
0.68 Remote Similarity NPD6584 Phase 3
0.6794 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6792 Remote Similarity NPD1409 Phase 3
0.678 Remote Similarity NPD6387 Discontinued
0.6777 Remote Similarity NPD9381 Approved
0.6777 Remote Similarity NPD9384 Approved
0.6768 Remote Similarity NPD9093 Approved
0.6767 Remote Similarity NPD4257 Approved
0.6767 Remote Similarity NPD4256 Phase 2
0.6757 Remote Similarity NPD4229 Approved
0.6757 Remote Similarity NPD3680 Approved
0.6757 Remote Similarity NPD4231 Approved
0.6757 Remote Similarity NPD3683 Approved
0.6757 Remote Similarity NPD3682 Approved
0.6757 Remote Similarity NPD3681 Approved
0.6752 Remote Similarity NPD4869 Clinical (unspecified phase)
0.675 Remote Similarity NPD1548 Phase 1
0.6748 Remote Similarity NPD3070 Discontinued
0.6748 Remote Similarity NPD2231 Phase 2
0.6748 Remote Similarity NPD2235 Phase 2
0.6746 Remote Similarity NPD2237 Approved
0.6744 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6744 Remote Similarity NPD6346 Approved
0.6744 Remote Similarity NPD3620 Phase 2
0.6744 Remote Similarity NPD2238 Phase 2

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data