NPASS Compound

Structure

NPC474559 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 6.9282 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 16 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 19 2 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 17 18 1 0 0 0 0 19 21 1 0 0 0 0 20 22 2 3 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	331.17
Volume:	356.543
LogP:	5.574
LogD:	4.749
LogS:	-5.572
# Rotatable Bonds:	7
TPSA:	29.1
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	3.107
Fsp3:	0.45
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:	-4.732
MDCK Permeability:	2.868872252292931e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.311
Plasma Protein Binding (PPB):	98.64923858642578%
Volume Distribution (VD):	1.853
Pgp-substrate:	1.0822569131851196%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.763
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.677
CYP2C9-inhibitor:	0.764
CYP2C9-substrate:	0.79
CYP2D6-inhibitor:	0.59
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.483
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	3.641
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.879
Human Hepatotoxicity (H-HT):	0.532
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.155
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.963
Carcinogencity:	0.34
Eye Corrosion:	0.006
Eye Irritation:	0.178
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC474559

Natural Product ID:	NPC474559
*Common Name:**	6-(7-Chloro-1,2,3,4-Tetrahydronaphthalen-2-Yl)-N-Isobutylhexa-2,4-Dienamide
IUPAC Name:	(2E,4E)-6-(7-chloro-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(2-methylpropyl)hexa-2,4-dienamide
Synonyms:
Standard InCHIKey:	TWZVEXSALOWIHE-BDWKERMESA-N
Standard InCHI:	InChI=1S/C20H26ClNO/c1-15(2)14-22-20(23)7-5-3-4-6-16-8-9-17-10-11-19(21)13-18(17)12-16/h3-5,7,10-11,13,15-16H,6,8-9,12,14H2,1-2H3,(H,22,23)/b4-3+,7-5+
SMILES:	CC(CN=C(/C=C/C=C/CC1CCc2c(C1)cc(cc2)Cl)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472226
PubChem CID:	44575520
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO32775	dinosperma erythrococca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599259]

☑ 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

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT734	Organism	Musca domestica	Musca domestica	Activity	=	40.0	%	PMID[451359]

☑ 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 NPC474559 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	2554
0.2-0.3	10808
0.3-0.4	19813
0.4-0.5	7976
0.5-0.6	1273
0.6-0.7	76
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7835	Intermediate Similarity	NPC14326
0.7525	Intermediate Similarity	NPC203076
0.7455	Intermediate Similarity	NPC471310
0.7426	Intermediate Similarity	NPC3210
0.7282	Intermediate Similarity	NPC473031
0.7048	Intermediate Similarity	NPC12429
0.6964	Remote Similarity	NPC469457
0.6863	Remote Similarity	NPC242628
0.6777	Remote Similarity	NPC471318
0.6759	Remote Similarity	NPC26224
0.6696	Remote Similarity	NPC33168
0.6694	Remote Similarity	NPC320656
0.6667	Remote Similarity	NPC274089
0.6667	Remote Similarity	NPC191215
0.6606	Remote Similarity	NPC172128
0.6587	Remote Similarity	NPC317564
0.6574	Remote Similarity	NPC262393
0.6566	Remote Similarity	NPC54269
0.6555	Remote Similarity	NPC77294
0.6525	Remote Similarity	NPC45033
0.6514	Remote Similarity	NPC470877
0.6481	Remote Similarity	NPC198747
0.6481	Remote Similarity	NPC60408
0.6466	Remote Similarity	NPC318154
0.6455	Remote Similarity	NPC159178
0.6455	Remote Similarity	NPC74936
0.6455	Remote Similarity	NPC471307
0.6455	Remote Similarity	NPC209764
0.6455	Remote Similarity	NPC78041
0.6455	Remote Similarity	NPC141139
0.6455	Remote Similarity	NPC121872
0.6444	Remote Similarity	NPC313352
0.6372	Remote Similarity	NPC161972
0.6372	Remote Similarity	NPC303045
0.6357	Remote Similarity	NPC109151
0.6355	Remote Similarity	NPC133162
0.633	Remote Similarity	NPC471638
0.6316	Remote Similarity	NPC25565
0.6311	Remote Similarity	NPC249018
0.6311	Remote Similarity	NPC313981
0.6311	Remote Similarity	NPC3190
0.6303	Remote Similarity	NPC211551
0.6283	Remote Similarity	NPC471309
0.6281	Remote Similarity	NPC24101
0.6281	Remote Similarity	NPC96224
0.6261	Remote Similarity	NPC473501
0.6261	Remote Similarity	NPC311242
0.6261	Remote Similarity	NPC475439
0.625	Remote Similarity	NPC245259
0.625	Remote Similarity	NPC220596
0.6228	Remote Similarity	NPC58674
0.6204	Remote Similarity	NPC267704
0.6198	Remote Similarity	NPC142297
0.6195	Remote Similarity	NPC265521
0.6195	Remote Similarity	NPC314690
0.619	Remote Similarity	NPC159661
0.6186	Remote Similarity	NPC155172
0.6179	Remote Similarity	NPC474149
0.6167	Remote Similarity	NPC474910
0.6161	Remote Similarity	NPC316108
0.6139	Remote Similarity	NPC280135
0.6139	Remote Similarity	NPC1008
0.6139	Remote Similarity	NPC158028
0.6139	Remote Similarity	NPC87099
0.6139	Remote Similarity	NPC135433
0.6139	Remote Similarity	NPC226999
0.6139	Remote Similarity	NPC39799
0.6139	Remote Similarity	NPC193578
0.6134	Remote Similarity	NPC19856
0.6129	Remote Similarity	NPC166837
0.6126	Remote Similarity	NPC325441
0.6121	Remote Similarity	NPC251579
0.6121	Remote Similarity	NPC133135
0.6116	Remote Similarity	NPC231705
0.6116	Remote Similarity	NPC471447
0.6106	Remote Similarity	NPC226438
0.61	Remote Similarity	NPC246822
0.61	Remote Similarity	NPC213570
0.61	Remote Similarity	NPC139416
0.6083	Remote Similarity	NPC472221
0.6083	Remote Similarity	NPC472222
0.6071	Remote Similarity	NPC298115
0.6071	Remote Similarity	NPC199567
0.6071	Remote Similarity	NPC316906
0.6061	Remote Similarity	NPC6107
0.6061	Remote Similarity	NPC472415
0.6058	Remote Similarity	NPC110264
0.6053	Remote Similarity	NPC128645
0.604	Remote Similarity	NPC72670
0.6038	Remote Similarity	NPC469894
0.6034	Remote Similarity	NPC3371
0.6033	Remote Similarity	NPC243601
0.602	Remote Similarity	NPC32312
0.602	Remote Similarity	NPC198023
0.6019	Remote Similarity	NPC283012
0.6019	Remote Similarity	NPC475199
0.6018	Remote Similarity	NPC258627
0.6	Remote Similarity	NPC178902
0.6	Remote Similarity	NPC474354
0.6	Remote Similarity	NPC82770
0.6	Remote Similarity	NPC239931
0.6	Remote Similarity	NPC99482
0.6	Remote Similarity	NPC78954
0.5983	Remote Similarity	NPC324602
0.5981	Remote Similarity	NPC315216
0.5981	Remote Similarity	NPC192623
0.5979	Remote Similarity	NPC71009
0.597	Remote Similarity	NPC472414
0.5968	Remote Similarity	NPC258056
0.5965	Remote Similarity	NPC470926
0.5965	Remote Similarity	NPC475059
0.5965	Remote Similarity	NPC475023
0.5965	Remote Similarity	NPC125226
0.5963	Remote Similarity	NPC172984
0.5962	Remote Similarity	NPC307195
0.596	Remote Similarity	NPC113837
0.596	Remote Similarity	NPC289915
0.5954	Remote Similarity	NPC80150
0.595	Remote Similarity	NPC224610
0.595	Remote Similarity	NPC88267
0.595	Remote Similarity	NPC113326
0.595	Remote Similarity	NPC194390
0.5946	Remote Similarity	NPC93843
0.5946	Remote Similarity	NPC474211
0.5938	Remote Similarity	NPC303370
0.5935	Remote Similarity	NPC472980
0.5935	Remote Similarity	NPC27252
0.5935	Remote Similarity	NPC472979
0.5926	Remote Similarity	NPC278097
0.5926	Remote Similarity	NPC133050
0.5922	Remote Similarity	NPC244738
0.5918	Remote Similarity	NPC45756
0.5918	Remote Similarity	NPC88566
0.5913	Remote Similarity	NPC475057
0.5909	Remote Similarity	NPC95429
0.5909	Remote Similarity	NPC273830
0.5909	Remote Similarity	NPC168855
0.5906	Remote Similarity	NPC91452
0.5902	Remote Similarity	NPC117115
0.59	Remote Similarity	NPC267443
0.5899	Remote Similarity	NPC3202
0.5887	Remote Similarity	NPC64642
0.5887	Remote Similarity	NPC11554
0.5887	Remote Similarity	NPC149455
0.5887	Remote Similarity	NPC182549
0.5887	Remote Similarity	NPC153690
0.5887	Remote Similarity	NPC114741
0.5887	Remote Similarity	NPC472982
0.5882	Remote Similarity	NPC251490
0.5876	Remote Similarity	NPC310758
0.5876	Remote Similarity	NPC238023
0.5876	Remote Similarity	NPC135924
0.5876	Remote Similarity	NPC210849
0.587	Remote Similarity	NPC183722
0.5868	Remote Similarity	NPC202613
0.5868	Remote Similarity	NPC471317
0.5865	Remote Similarity	NPC96835
0.5865	Remote Similarity	NPC258492
0.5859	Remote Similarity	NPC291066
0.5859	Remote Similarity	NPC113099
0.5859	Remote Similarity	NPC118202
0.5857	Remote Similarity	NPC132847
0.5856	Remote Similarity	NPC123476
0.5846	Remote Similarity	NPC283468
0.584	Remote Similarity	NPC65855
0.584	Remote Similarity	NPC292758
0.5839	Remote Similarity	NPC472413
0.5839	Remote Similarity	NPC295478
0.5839	Remote Similarity	NPC71271
0.5839	Remote Similarity	NPC116057
0.5833	Remote Similarity	NPC136810
0.5833	Remote Similarity	NPC469481
0.5833	Remote Similarity	NPC184030
0.5833	Remote Similarity	NPC263835
0.5833	Remote Similarity	NPC316797
0.5833	Remote Similarity	NPC474582
0.5833	Remote Similarity	NPC164449
0.5833	Remote Similarity	NPC128248
0.5833	Remote Similarity	NPC133809
0.5833	Remote Similarity	NPC225079
0.5827	Remote Similarity	NPC42423
0.5825	Remote Similarity	NPC125144
0.5825	Remote Similarity	NPC121708
0.5818	Remote Similarity	NPC104070
0.5818	Remote Similarity	NPC146703
0.5818	Remote Similarity	NPC477770
0.5816	Remote Similarity	NPC22786
0.5814	Remote Similarity	NPC244403
0.5814	Remote Similarity	NPC317254
0.5814	Remote Similarity	NPC37302
0.581	Remote Similarity	NPC276699
0.5806	Remote Similarity	NPC151477
0.5804	Remote Similarity	NPC243166
0.5802	Remote Similarity	NPC220698
0.5802	Remote Similarity	NPC122009
0.58	Remote Similarity	NPC178527
0.5794	Remote Similarity	NPC103488
0.5794	Remote Similarity	NPC224544
0.5794	Remote Similarity	NPC475002
0.5794	Remote Similarity	NPC50192

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 NPC474559 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1010
0.2-0.3	1145
0.3-0.4	3465
0.4-0.5	2464
0.5-0.6	794
0.6-0.7	122
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7395	Intermediate Similarity	NPD2617	Discontinued
0.7383	Intermediate Similarity	NPD2895	Discontinued
0.7241	Intermediate Similarity	NPD3651	Discontinued
0.7156	Intermediate Similarity	NPD1076	Approved
0.7156	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1415	Approved
0.7094	Intermediate Similarity	NPD2499	Approved
0.7094	Intermediate Similarity	NPD2500	Approved
0.7059	Intermediate Similarity	NPD5288	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5753	Discontinued
0.7027	Intermediate Similarity	NPD523	Approved
0.7027	Intermediate Similarity	NPD524	Approved
0.7025	Intermediate Similarity	NPD1359	Approved
0.6991	Remote Similarity	NPD5103	Approved
0.6972	Remote Similarity	NPD2655	Approved
0.6972	Remote Similarity	NPD2656	Approved
0.6885	Remote Similarity	NPD2108	Phase 2
0.6885	Remote Similarity	NPD2109	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2991	Approved
0.6833	Remote Similarity	NPD2988	Approved
0.6832	Remote Similarity	NPD1475	Approved
0.6818	Remote Similarity	NPD4814	Discontinued
0.68	Remote Similarity	NPD1302	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7431	Approved
0.6767	Remote Similarity	NPD7430	Approved
0.6757	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1401	Approved
0.6741	Remote Similarity	NPD6586	Approved
0.6741	Remote Similarity	NPD6587	Approved
0.6718	Remote Similarity	NPD2372	Approved
0.6694	Remote Similarity	NPD2396	Approved
0.6694	Remote Similarity	NPD2395	Approved
0.6667	Remote Similarity	NPD4544	Approved
0.6667	Remote Similarity	NPD2657	Approved
0.6667	Remote Similarity	NPD1935	Phase 3
0.6667	Remote Similarity	NPD1616	Discontinued
0.6642	Remote Similarity	NPD6086	Phase 2
0.6637	Remote Similarity	NPD728	Approved
0.6636	Remote Similarity	NPD187	Approved
0.6614	Remote Similarity	NPD3974	Phase 2
0.6613	Remote Similarity	NPD5130	Phase 3
0.6612	Remote Similarity	NPD7121	Approved
0.6602	Remote Similarity	NPD3903	Approved
0.6602	Remote Similarity	NPD3981	Approved
0.6602	Remote Similarity	NPD3979	Approved
0.6602	Remote Similarity	NPD3904	Approved
0.6589	Remote Similarity	NPD3098	Discontinued
0.6589	Remote Similarity	NPD2031	Discontinued
0.6583	Remote Similarity	NPD801	Discontinued
0.6571	Remote Similarity	NPD4635	Approved
0.6571	Remote Similarity	NPD1185	Approved
0.6571	Remote Similarity	NPD263	Approved
0.6571	Remote Similarity	NPD3971	Phase 1
0.6571	Remote Similarity	NPD262	Approved
0.6565	Remote Similarity	NPD6984	Approved
0.6518	Remote Similarity	NPD6049	Phase 2
0.6518	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7120	Approved
0.6496	Remote Similarity	NPD2937	Phase 1
0.6496	Remote Similarity	NPD2939	Approved
0.6484	Remote Similarity	NPD3603	Phase 3
0.6471	Remote Similarity	NPD5212	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD9722	Approved
0.6466	Remote Similarity	NPD4818	Approved
0.6466	Remote Similarity	NPD9721	Approved
0.6466	Remote Similarity	NPD4817	Approved
0.6457	Remote Similarity	NPD2597	Suspended
0.6457	Remote Similarity	NPD2596	Phase 2
0.6457	Remote Similarity	NPD4594	Approved
0.6457	Remote Similarity	NPD4593	Approved
0.6449	Remote Similarity	NPD1884	Approved
0.6442	Remote Similarity	NPD914	Suspended
0.6441	Remote Similarity	NPD2833	Approved
0.6441	Remote Similarity	NPD2834	Approved
0.6434	Remote Similarity	NPD1498	Approved
0.6422	Remote Similarity	NPD1101	Approved
0.6391	Remote Similarity	NPD4698	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD3035	Approved
0.6379	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6236	Approved
0.6364	Remote Similarity	NPD6235	Approved
0.6355	Remote Similarity	NPD3429	Approved
0.6355	Remote Similarity	NPD3427	Approved
0.6343	Remote Similarity	NPD5246	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6690	Approved
0.6336	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6406	Approved
0.6333	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3428	Approved
0.633	Remote Similarity	NPD3426	Approved
0.6328	Remote Similarity	NPD4164	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD2841	Approved
0.6321	Remote Similarity	NPD4170	Approved
0.6321	Remote Similarity	NPD4169	Approved
0.6321	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD188	Approved
0.6311	Remote Similarity	NPD189	Phase 3
0.6311	Remote Similarity	NPD3643	Approved
0.6311	Remote Similarity	NPD3642	Approved
0.6311	Remote Similarity	NPD3644	Approved
0.6308	Remote Similarity	NPD4878	Approved
0.6299	Remote Similarity	NPD4016	Approved
0.629	Remote Similarity	NPD7059	Approved
0.629	Remote Similarity	NPD7060	Approved
0.6283	Remote Similarity	NPD3980	Approved
0.6283	Remote Similarity	NPD2878	Approved
0.6283	Remote Similarity	NPD3982	Approved
0.6276	Remote Similarity	NPD3364	Phase 3
0.6271	Remote Similarity	NPD3680	Approved
0.6271	Remote Similarity	NPD4229	Approved
0.6271	Remote Similarity	NPD4231	Approved
0.6271	Remote Similarity	NPD3682	Approved
0.625	Remote Similarity	NPD449	Clinical (unspecified phase)
0.625	Remote Similarity	NPD530	Approved
0.625	Remote Similarity	NPD448	Clinical (unspecified phase)
0.625	Remote Similarity	NPD517	Discontinued
0.6241	Remote Similarity	NPD1516	Approved
0.624	Remote Similarity	NPD5631	Phase 3
0.6239	Remote Similarity	NPD4409	Approved
0.6239	Remote Similarity	NPD3099	Discontinued
0.6239	Remote Similarity	NPD4406	Approved
0.6231	Remote Similarity	NPD1703	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD472	Approved
0.6224	Remote Similarity	NPD7575	Phase 3
0.6202	Remote Similarity	NPD4631	Approved
0.6202	Remote Similarity	NPD1320	Phase 1
0.6202	Remote Similarity	NPD4630	Approved
0.6202	Remote Similarity	NPD4589	Approved
0.6202	Remote Similarity	NPD5407	Approved
0.6195	Remote Similarity	NPD752	Approved
0.6195	Remote Similarity	NPD1812	Approved
0.6195	Remote Similarity	NPD1814	Approved
0.6186	Remote Similarity	NPD4119	Approved
0.6183	Remote Similarity	NPD5335	Discontinued
0.6165	Remote Similarity	NPD5653	Discontinued
0.6161	Remote Similarity	NPD3346	Approved
0.6161	Remote Similarity	NPD3344	Approved
0.6159	Remote Similarity	NPD3851	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4147	Approved
0.6154	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5057	Phase 3
0.6154	Remote Similarity	NPD4879	Approved
0.6154	Remote Similarity	NPD5056	Approved
0.6154	Remote Similarity	NPD4144	Approved
0.6147	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.614	Remote Similarity	NPD1409	Phase 3
0.6134	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4656	Approved
0.6134	Remote Similarity	NPD4658	Approved
0.6134	Remote Similarity	NPD3681	Approved
0.6134	Remote Similarity	NPD3683	Approved
0.6133	Remote Similarity	NPD6725	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6726	Phase 2
0.6126	Remote Similarity	NPD3345	Approved
0.6111	Remote Similarity	NPD2001	Discontinued
0.6111	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4000	Phase 3
0.6103	Remote Similarity	NPD1500	Approved
0.6098	Remote Similarity	NPD1792	Phase 2
0.6094	Remote Similarity	NPD828	Approved
0.6087	Remote Similarity	NPD4452	Approved
0.6087	Remote Similarity	NPD4453	Approved
0.6087	Remote Similarity	NPD1555	Discontinued
0.6083	Remote Similarity	NPD3048	Approved
0.6083	Remote Similarity	NPD3047	Approved
0.6083	Remote Similarity	NPD3046	Approved
0.6075	Remote Similarity	NPD4026	Approved
0.6075	Remote Similarity	NPD4027	Approved
0.6074	Remote Similarity	NPD2035	Discontinued
0.6071	Remote Similarity	NPD7231	Approved
0.6071	Remote Similarity	NPD7230	Approved
0.6068	Remote Similarity	NPD4117	Approved
0.6063	Remote Similarity	NPD4801	Phase 1
0.6053	Remote Similarity	NPD4407	Approved
0.6053	Remote Similarity	NPD9251	Approved
0.6053	Remote Similarity	NPD4405	Approved
0.6053	Remote Similarity	NPD4408	Approved
0.6053	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD2583	Phase 2
0.6048	Remote Similarity	NPD4253	Approved
0.6048	Remote Similarity	NPD4254	Approved
0.6047	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD1903	Approved
0.6043	Remote Similarity	NPD1859	Approved
0.6036	Remote Similarity	NPD4146	Approved
0.6036	Remote Similarity	NPD4145	Approved
0.6036	Remote Similarity	NPD2002	Discontinued
0.6033	Remote Similarity	NPD5717	Approved
0.6032	Remote Similarity	NPD2665	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD1067	Discontinued
0.6015	Remote Similarity	NPD727	Discontinued
0.6015	Remote Similarity	NPD2371	Approved
0.6014	Remote Similarity	NPD1214	Approved
0.6	Remote Similarity	NPD4545	Approved
0.6	Remote Similarity	NPD1080	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