NPASS Compound

Structure

CID117115 OpenBabel06191715472D 21 22 0 0 1 0 0 0 0 0999 V2000 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 -1.7321 3.0000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 0.8660 -0.5000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 2 0 0 0 0 15 4 1 1 0 0 0 16 5 1 6 0 0 0 16 20 1 0 0 0 0 17 15 1 1 0 0 0 17 18 1 0 0 0 0 18 20 2 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	335.608
LogP:	6.858
LogD:	4.931
LogS:	-6.289
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	3.733
Fsp3:	0.6
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:	-4.757
MDCK Permeability:	1.2979654457012657e-05
Pgp-inhibitor:	0.901
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.445
Plasma Protein Binding (PPB):	99.29076385498047%
Volume Distribution (VD):	7.706
Pgp-substrate:	3.659907817840576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.824
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.827
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.665
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.646
CYP3A4-substrate:	0.551

ADMET: Excretion

Clearance (CL):	10.315
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.752
Drug-inuced Liver Injury (DILI):	0.451
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.822
Carcinogencity:	0.139
Eye Corrosion:	0.195
Eye Irritation:	0.953
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC117115

Natural Product ID:	NPC117115
*Common Name:**	Leubethanol
IUPAC Name:	(5S,8R)-3,8-dimethyl-5-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalen-1-ol
Synonyms:	Leubethanol
Standard InCHIKey:	WQVJUBFKFCDYDQ-BBWFWOEESA-N
Standard InCHI:	InChI=1S/C20H30O/c1-13(2)7-6-8-15(4)17-10-9-16(5)20-18(17)11-14(3)12-19(20)21/h7,11-12,15-17,21H,6,8-10H2,1-5H3/t15-,16+,17-/m0/s1
SMILES:	CC(=CCC[C@@H]([C@@H]1CC[C@H](c2c1cc(C)cc2O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822510
PubChem CID:	54669845
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000351] Biflorane and serrulatane diterpenoids

*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
NPO13855	Leucophyllum frutescens	Species	Scrophulariaceae	Eukaryota	n.a.	root	n.a.	PMID[21859082]
NPO13855	Leucophyllum frutescens	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21859082]
NPO13855	Leucophyllum frutescens	Species	Scrophulariaceae	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

Activity Type	# Activity
MIC	3
Others	4

Activity Type	# Activity
Cell Line	1
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	123000.0	nM	PMID[485211]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	12.5	ug.mL-1	PMID[485210]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	6.3	ug.mL-1	PMID[485210]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Ratio	=	16.0	n.a.	PMID[485210]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	25100.0	nM	PMID[485211]
NPT2	Others	Unspecified		Selectivity Index	=	4.9	n.a.	PMID[485211]

☑ 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 NPC117115 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	336
0.1-0.2	1837
0.2-0.3	4658
0.3-0.4	12997
0.4-0.5	7405
0.5-0.6	9728
0.6-0.7	4341
0.7-0.8	1065
0.8-0.85	212
0.85-0.9	93
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9798	High Similarity	NPC151477
0.951	High Similarity	NPC132720
0.95	High Similarity	NPC21594
0.9417	High Similarity	NPC260323
0.9417	High Similarity	NPC176279
0.9412	High Similarity	NPC58865
0.9327	High Similarity	NPC250323
0.93	High Similarity	NPC238696
0.9238	High Similarity	NPC715
0.9231	High Similarity	NPC151537
0.9184	High Similarity	NPC79241
0.9184	High Similarity	NPC6597
0.9151	High Similarity	NPC195922
0.9143	High Similarity	NPC46940
0.9135	High Similarity	NPC141782
0.9135	High Similarity	NPC13482
0.9109	High Similarity	NPC272029
0.9082	High Similarity	NPC259512
0.9082	High Similarity	NPC312132
0.9065	High Similarity	NPC192948
0.9065	High Similarity	NPC35797
0.9048	High Similarity	NPC95716
0.9048	High Similarity	NPC469912
0.9	High Similarity	NPC72729
0.8981	High Similarity	NPC308311
0.8981	High Similarity	NPC471668
0.8981	High Similarity	NPC477137
0.8981	High Similarity	NPC38893
0.8962	High Similarity	NPC471179
0.8942	High Similarity	NPC11554
0.8911	High Similarity	NPC252105
0.89	High Similarity	NPC33675
0.89	High Similarity	NPC299762
0.8899	High Similarity	NPC477136
0.8899	High Similarity	NPC304510
0.8899	High Similarity	NPC172219
0.8889	High Similarity	NPC469719
0.8878	High Similarity	NPC245187
0.8868	High Similarity	NPC266937
0.8868	High Similarity	NPC470770
0.8868	High Similarity	NPC77772
0.8857	High Similarity	NPC314187
0.8846	High Similarity	NPC320439
0.8818	High Similarity	NPC471671
0.8812	High Similarity	NPC211885
0.8807	High Similarity	NPC92
0.8807	High Similarity	NPC469663
0.8807	High Similarity	NPC219112
0.88	High Similarity	NPC156313
0.88	High Similarity	NPC77492
0.8796	High Similarity	NPC268160
0.8788	High Similarity	NPC222146
0.8785	High Similarity	NPC302371
0.8785	High Similarity	NPC177962
0.8785	High Similarity	NPC62867
0.875	High Similarity	NPC271274
0.8739	High Similarity	NPC151197
0.8739	High Similarity	NPC126002
0.8739	High Similarity	NPC469644
0.8739	High Similarity	NPC93071
0.8738	High Similarity	NPC475225
0.8725	High Similarity	NPC477685
0.8725	High Similarity	NPC51015
0.8716	High Similarity	NPC246760
0.8716	High Similarity	NPC147179
0.8716	High Similarity	NPC84999
0.8704	High Similarity	NPC263753
0.8704	High Similarity	NPC322239
0.8704	High Similarity	NPC317869
0.8692	High Similarity	NPC322753
0.8692	High Similarity	NPC224527
0.8687	High Similarity	NPC76938
0.8679	High Similarity	NPC299568
0.8679	High Similarity	NPC186385
0.8673	High Similarity	NPC231150
0.8661	High Similarity	NPC478121
0.8654	High Similarity	NPC138942
0.8654	High Similarity	NPC47284
0.8649	High Similarity	NPC154030
0.8641	High Similarity	NPC269212
0.8641	High Similarity	NPC108497
0.8641	High Similarity	NPC471228
0.8641	High Similarity	NPC235762
0.8641	High Similarity	NPC168829
0.8636	High Similarity	NPC308828
0.8627	High Similarity	NPC225506
0.8624	High Similarity	NPC107240
0.8624	High Similarity	NPC471534
0.8624	High Similarity	NPC249270
0.8611	High Similarity	NPC228425
0.86	High Similarity	NPC32714
0.86	High Similarity	NPC8392
0.8598	High Similarity	NPC224870
0.8598	High Similarity	NPC296683
0.8586	High Similarity	NPC147284
0.8586	High Similarity	NPC306884
0.8586	High Similarity	NPC3358
0.8586	High Similarity	NPC210497
0.8586	High Similarity	NPC162314
0.8586	High Similarity	NPC94139
0.8585	High Similarity	NPC64586
0.8584	High Similarity	NPC259703
0.8584	High Similarity	NPC32322
0.8584	High Similarity	NPC241001
0.8571	High Similarity	NPC53740
0.8571	High Similarity	NPC192
0.8571	High Similarity	NPC469913
0.8559	High Similarity	NPC16030
0.8559	High Similarity	NPC299180
0.8558	High Similarity	NPC288411
0.8558	High Similarity	NPC475580
0.8557	High Similarity	NPC19680
0.8544	High Similarity	NPC12221
0.8532	High Similarity	NPC117846
0.8532	High Similarity	NPC23804
0.8529	High Similarity	NPC122005
0.8529	High Similarity	NPC252821
0.8509	High Similarity	NPC249340
0.8509	High Similarity	NPC162935
0.8509	High Similarity	NPC154696
0.8505	High Similarity	NPC33728
0.8505	High Similarity	NPC19808
0.85	High Similarity	NPC289769
0.85	High Similarity	NPC152415
0.8491	Intermediate Similarity	NPC66834
0.8482	Intermediate Similarity	NPC469609
0.8482	Intermediate Similarity	NPC206
0.8476	Intermediate Similarity	NPC37802
0.8468	Intermediate Similarity	NPC141001
0.8462	Intermediate Similarity	NPC233827
0.8462	Intermediate Similarity	NPC168393
0.8447	Intermediate Similarity	NPC248396
0.8447	Intermediate Similarity	NPC48730
0.8447	Intermediate Similarity	NPC129373
0.8447	Intermediate Similarity	NPC174911
0.8435	Intermediate Similarity	NPC297057
0.8435	Intermediate Similarity	NPC121168
0.8435	Intermediate Similarity	NPC11250
0.8435	Intermediate Similarity	NPC71094
0.8431	Intermediate Similarity	NPC152097
0.8431	Intermediate Similarity	NPC32674
0.8421	Intermediate Similarity	NPC129176
0.8416	Intermediate Similarity	NPC144682
0.8411	Intermediate Similarity	NPC174981
0.84	Intermediate Similarity	NPC55903
0.84	Intermediate Similarity	NPC271440
0.8396	Intermediate Similarity	NPC99836
0.8396	Intermediate Similarity	NPC12640
0.8396	Intermediate Similarity	NPC54765
0.8396	Intermediate Similarity	NPC201662
0.8396	Intermediate Similarity	NPC155072
0.8396	Intermediate Similarity	NPC310456
0.8381	Intermediate Similarity	NPC227458
0.8381	Intermediate Similarity	NPC323810
0.8381	Intermediate Similarity	NPC218879
0.8381	Intermediate Similarity	NPC244513
0.8367	Intermediate Similarity	NPC27974
0.8365	Intermediate Similarity	NPC80800
0.8364	Intermediate Similarity	NPC321589
0.8364	Intermediate Similarity	NPC319803
0.8362	Intermediate Similarity	NPC471187
0.8362	Intermediate Similarity	NPC275145
0.835	Intermediate Similarity	NPC260775
0.8349	Intermediate Similarity	NPC4493
0.8349	Intermediate Similarity	NPC476632
0.8349	Intermediate Similarity	NPC225679
0.8349	Intermediate Similarity	NPC54373
0.8349	Intermediate Similarity	NPC165770
0.8349	Intermediate Similarity	NPC470723
0.8348	Intermediate Similarity	NPC48623
0.8348	Intermediate Similarity	NPC168707
0.8333	Intermediate Similarity	NPC473388
0.8333	Intermediate Similarity	NPC135467
0.8333	Intermediate Similarity	NPC260832
0.8333	Intermediate Similarity	NPC82664
0.8333	Intermediate Similarity	NPC216520
0.8333	Intermediate Similarity	NPC132271
0.8333	Intermediate Similarity	NPC292730
0.8319	Intermediate Similarity	NPC63010
0.8318	Intermediate Similarity	NPC232523
0.8318	Intermediate Similarity	NPC204901
0.8318	Intermediate Similarity	NPC158253
0.8304	Intermediate Similarity	NPC247858
0.8304	Intermediate Similarity	NPC137496
0.8304	Intermediate Similarity	NPC474387
0.8304	Intermediate Similarity	NPC115808
0.8304	Intermediate Similarity	NPC154511
0.8304	Intermediate Similarity	NPC257540
0.8304	Intermediate Similarity	NPC474358
0.8302	Intermediate Similarity	NPC99557
0.8302	Intermediate Similarity	NPC219286
0.83	Intermediate Similarity	NPC306074
0.83	Intermediate Similarity	NPC304541
0.83	Intermediate Similarity	NPC204210
0.8291	Intermediate Similarity	NPC199273
0.8291	Intermediate Similarity	NPC181334
0.8283	Intermediate Similarity	NPC70436
0.8276	Intermediate Similarity	NPC176208
0.8273	Intermediate Similarity	NPC166995
0.8273	Intermediate Similarity	NPC43525

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 NPC117115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	1023
0.2-0.3	1353
0.3-0.4	2980
0.4-0.5	1879
0.5-0.6	1135
0.6-0.7	343
0.7-0.8	77
0.8-0.85	3
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9143	High Similarity	NPD7635	Approved
0.9082	High Similarity	NPD288	Approved
0.9029	High Similarity	NPD2342	Discontinued
0.898	High Similarity	NPD844	Approved
0.8776	High Similarity	NPD845	Approved
0.8679	High Similarity	NPD4750	Phase 3
0.8529	High Similarity	NPD3020	Approved
0.8416	Intermediate Similarity	NPD1809	Phase 2
0.8269	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2859	Approved
0.8235	Intermediate Similarity	NPD2860	Approved
0.8165	Intermediate Similarity	NPD1792	Phase 2
0.8165	Intermediate Similarity	NPD3021	Approved
0.8165	Intermediate Similarity	NPD3022	Approved
0.8158	Intermediate Similarity	NPD3091	Approved
0.8142	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD2933	Approved
0.8137	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD2934	Approved
0.8051	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD4059	Approved
0.8017	Intermediate Similarity	NPD3019	Approved
0.8017	Intermediate Similarity	NPD2932	Approved
0.7965	Intermediate Similarity	NPD497	Approved
0.7944	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4093	Discontinued
0.789	Intermediate Similarity	NPD1445	Approved
0.789	Intermediate Similarity	NPD1444	Approved
0.7881	Intermediate Similarity	NPD3092	Approved
0.7876	Intermediate Similarity	NPD496	Approved
0.7876	Intermediate Similarity	NPD495	Approved
0.7876	Intermediate Similarity	NPD498	Approved
0.7863	Intermediate Similarity	NPD4626	Approved
0.7863	Intermediate Similarity	NPD2286	Discontinued
0.7863	Intermediate Similarity	NPD1751	Approved
0.7845	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7340	Approved
0.7805	Intermediate Similarity	NPD4625	Phase 3
0.7719	Intermediate Similarity	NPD1398	Phase 1
0.7712	Intermediate Similarity	NPD3095	Discontinued
0.7692	Intermediate Similarity	NPD5303	Approved
0.7692	Intermediate Similarity	NPD5304	Approved
0.7686	Intermediate Similarity	NPD6696	Suspended
0.7685	Intermediate Similarity	NPD846	Approved
0.7685	Intermediate Similarity	NPD940	Approved
0.7623	Intermediate Similarity	NPD3094	Phase 2
0.7615	Intermediate Similarity	NPD9500	Approved
0.7603	Intermediate Similarity	NPD4749	Approved
0.76	Intermediate Similarity	NPD111	Approved
0.7586	Intermediate Similarity	NPD6671	Approved
0.7583	Intermediate Similarity	NPD1201	Approved
0.7565	Intermediate Similarity	NPD2234	Approved
0.7565	Intermediate Similarity	NPD2229	Approved
0.7565	Intermediate Similarity	NPD2228	Approved
0.7563	Intermediate Similarity	NPD4589	Approved
0.7561	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2194	Approved
0.7561	Intermediate Similarity	NPD2195	Approved
0.7544	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5736	Approved
0.75	Intermediate Similarity	NPD3635	Approved
0.75	Intermediate Similarity	NPD3636	Approved
0.75	Intermediate Similarity	NPD4097	Suspended
0.75	Intermediate Similarity	NPD3637	Approved
0.748	Intermediate Similarity	NPD4060	Phase 1
0.7479	Intermediate Similarity	NPD5691	Approved
0.744	Intermediate Similarity	NPD2605	Approved
0.744	Intermediate Similarity	NPD2606	Approved
0.7431	Intermediate Similarity	NPD1242	Phase 1
0.7414	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD1283	Approved
0.7395	Intermediate Similarity	NPD7330	Discontinued
0.7381	Intermediate Similarity	NPD5155	Approved
0.7381	Intermediate Similarity	NPD5156	Approved
0.7377	Intermediate Similarity	NPD2230	Approved
0.7377	Intermediate Similarity	NPD2233	Approved
0.7377	Intermediate Similarity	NPD2232	Approved
0.7355	Intermediate Similarity	NPD3023	Approved
0.7355	Intermediate Similarity	NPD3026	Approved
0.7339	Intermediate Similarity	NPD1470	Approved
0.7333	Intermediate Similarity	NPD3024	Approved
0.7333	Intermediate Similarity	NPD3025	Approved
0.7333	Intermediate Similarity	NPD1651	Approved
0.7323	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3595	Approved
0.7302	Intermediate Similarity	NPD3594	Approved
0.7295	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1611	Approved
0.7295	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD709	Approved
0.728	Intermediate Similarity	NPD4624	Approved
0.7266	Intermediate Similarity	NPD6663	Approved
0.7265	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1983	Approved
0.7213	Intermediate Similarity	NPD1980	Approved
0.7213	Intermediate Similarity	NPD1981	Approved
0.7209	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3620	Phase 2
0.7203	Intermediate Similarity	NPD1791	Approved
0.7203	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1793	Approved
0.72	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1281	Approved
0.7121	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD3028	Approved
0.709	Intermediate Similarity	NPD4257	Approved
0.709	Intermediate Similarity	NPD4256	Phase 2
0.7087	Intermediate Similarity	NPD2861	Phase 2
0.7083	Intermediate Similarity	NPD7636	Approved
0.7068	Intermediate Similarity	NPD5406	Approved
0.7068	Intermediate Similarity	NPD6100	Approved
0.7068	Intermediate Similarity	NPD5404	Approved
0.7068	Intermediate Similarity	NPD5405	Approved
0.7068	Intermediate Similarity	NPD5408	Approved
0.7068	Intermediate Similarity	NPD6099	Approved
0.7054	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5327	Phase 3
0.704	Intermediate Similarity	NPD1669	Approved
0.7025	Intermediate Similarity	NPD7644	Approved
0.7	Intermediate Similarity	NPD6387	Discontinued
0.6992	Remote Similarity	NPD7743	Approved
0.6992	Remote Similarity	NPD7742	Approved
0.6978	Remote Similarity	NPD6090	Discontinued
0.6964	Remote Similarity	NPD1616	Discontinued
0.6957	Remote Similarity	NPD7390	Discontinued
0.6949	Remote Similarity	NPD228	Approved
0.6947	Remote Similarity	NPD4140	Approved
0.6937	Remote Similarity	NPD9273	Approved
0.6935	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3143	Discontinued
0.693	Remote Similarity	NPD9608	Approved
0.693	Remote Similarity	NPD9610	Approved
0.6923	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5951	Approved
0.6912	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3444	Approved
0.6911	Remote Similarity	NPD3445	Approved
0.6911	Remote Similarity	NPD3443	Approved
0.6906	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4818	Approved
0.6903	Remote Similarity	NPD4817	Approved
0.6899	Remote Similarity	NPD4908	Phase 1
0.6894	Remote Similarity	NPD5735	Approved
0.6891	Remote Similarity	NPD1138	Approved
0.6889	Remote Similarity	NPD5762	Approved
0.6889	Remote Similarity	NPD4725	Approved
0.6889	Remote Similarity	NPD5763	Approved
0.6889	Remote Similarity	NPD4721	Approved
0.6889	Remote Similarity	NPD4726	Approved
0.688	Remote Similarity	NPD1610	Phase 2
0.6861	Remote Similarity	NPD7003	Approved
0.6855	Remote Similarity	NPD2668	Approved
0.6855	Remote Similarity	NPD2667	Approved
0.6855	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2157	Approved
0.6842	Remote Similarity	NPD6353	Approved
0.6837	Remote Similarity	NPD9087	Approved
0.6835	Remote Similarity	NPD2421	Approved
0.6835	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7041	Phase 2
0.6835	Remote Similarity	NPD2420	Approved
0.6829	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3070	Discontinued
0.6822	Remote Similarity	NPD1712	Approved
0.6818	Remote Similarity	NPD2979	Phase 3
0.6818	Remote Similarity	NPD2238	Phase 2
0.681	Remote Similarity	NPD968	Approved
0.6807	Remote Similarity	NPD1139	Approved
0.6807	Remote Similarity	NPD1137	Approved
0.6797	Remote Similarity	NPD2797	Approved
0.6797	Remote Similarity	NPD1164	Approved
0.6794	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2209	Approved
0.6788	Remote Similarity	NPD3638	Discontinued
0.6788	Remote Similarity	NPD2211	Approved
0.6777	Remote Similarity	NPD9618	Approved
0.6777	Remote Similarity	NPD9614	Approved
0.6772	Remote Similarity	NPD1755	Approved
0.6765	Remote Similarity	NPD2346	Discontinued
0.6763	Remote Similarity	NPD3300	Phase 2
0.675	Remote Similarity	NPD9379	Approved
0.675	Remote Similarity	NPD9377	Approved
0.6744	Remote Similarity	NPD6584	Phase 3
0.6739	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1778	Approved
0.6716	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7037	Approved
0.6696	Remote Similarity	NPD3682	Approved
0.6696	Remote Similarity	NPD4231	Approved
0.6696	Remote Similarity	NPD3680	Approved
0.6696	Remote Similarity	NPD4229	Approved
0.6695	Remote Similarity	NPD2684	Approved
0.6693	Remote Similarity	NPD1608	Approved
0.6693	Remote Similarity	NPD2235	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