NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	347.681
LogP:	5.477
LogD:	4.511
LogS:	-4.255
# Rotatable Bonds:	7
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	3.539
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.785
MDCK Permeability:	2.1675325115211308e-05
Pgp-inhibitor:	0.768
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.781
30% Bioavailability (F30%):	0.254

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	99.83898162841797%
Volume Distribution (VD):	2.117
Pgp-substrate:	2.0957794189453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.859
CYP1A2-substrate:	0.252
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.295
CYP2C9-inhibitor:	0.753
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.595
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	7.213
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.443
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.258
Skin Sensitization:	0.939
Carcinogencity:	0.062
Eye Corrosion:	0.18
Eye Irritation:	0.952
Respiratory Toxicity:	0.292

Download Data

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

Natural Product: NPC477814

Natural Product ID:	NPC477814
*Common Name:**	4-[(5E)-3,6,10-trimethylundeca-1,5,9-trien-3-yl]benzene-1,2-diol
IUPAC Name:	4-[(5E)-3,6,10-trimethylundeca-1,5,9-trien-3-yl]benzene-1,2-diol
Synonyms:	4-Nerolidylcatechol
Standard InCHIKey:	YAHXRAWYSGJCNV-FOWTUZBSSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-6-20(5,17-10-11-18(21)19(22)14-17)13-12-16(4)9-7-8-15(2)3/h6,8,10-12,14,21-22H,1,7,9,13H2,2-5H3/b16-12+
SMILES:	CC(=CCC/C(=C/CC(C)(C=C)C1=CC(=C(C=C1)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45271245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO33630	Pothomorphe peltata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19299148]

☑ 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
IC50	7
LD50	1
Others	10

Activity Type	# Activity
Cell Line	3
Organism	3
Others	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	12.17	ug/ml	PMID[19084293]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6.17	ug/ml	PMID[19084293]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	507000	nM	PMID[23376996]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	670	nM	PMID[19084293]
NPT2	Others	Unspecified		Activity	=	0.5	n.a.	PMID[19084293]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	670	nM	PMID[19299148]
NPT32	Organism	Mus musculus	Mus musculus	LD50	>	2000	mg/kg	PMID[23376996]
NPT2	Others	Unspecified		Activity	=	26	%	PMID[23376996]
NPT2	Others	Unspecified		Activity	=	24	%	PMID[23376996]
NPT2	Others	Unspecified		Activity	=	14	%	PMID[23376996]
NPT2	Others	Unspecified		Activity	=	74	%	PMID[23376996]
NPT2	Others	Unspecified		Activity	=	76	%	PMID[23376996]
NPT2	Others	Unspecified		Activity	=	86	%	PMID[23376996]
NPT2	Others	Unspecified		IC50	=	293000	nM	PMID[23376996]
NPT2	Others	Unspecified		Activity	>	5	%	PMID[23376996]
NPT2	Others	Unspecified		Activity	=	75	%	PMID[23376996]
NPT2	Others	Unspecified		IC50	=	3.76	ug/ml	PMID[23376996]
NPT1	Others	Radical scavenging activity		Activity	=	75	%	PMID[23376996]

☑ 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 NPC477814 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	277
0.1-0.2	1692
0.2-0.3	4458
0.3-0.4	13704
0.4-0.5	6113
0.5-0.6	9767
0.6-0.7	4759
0.7-0.8	1632
0.8-0.85	225
0.85-0.9	61
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC120719
0.9495	High Similarity	NPC196479
0.932	High Similarity	NPC228343
0.932	High Similarity	NPC254833
0.9286	High Similarity	NPC109955
0.9118	High Similarity	NPC239291
0.9082	High Similarity	NPC107522
0.902	High Similarity	NPC471511
0.901	High Similarity	NPC110764
0.898	High Similarity	NPC316301
0.898	High Similarity	NPC27323
0.8952	High Similarity	NPC55617
0.8952	High Similarity	NPC62258
0.8878	High Similarity	NPC55903
0.8868	High Similarity	NPC174096
0.8868	High Similarity	NPC79793
0.8868	High Similarity	NPC147634
0.8868	High Similarity	NPC120982
0.8868	High Similarity	NPC226401
0.8835	High Similarity	NPC12278
0.8818	High Similarity	NPC16030
0.8812	High Similarity	NPC131587
0.8812	High Similarity	NPC92730
0.8785	High Similarity	NPC179002
0.8785	High Similarity	NPC187583
0.8785	High Similarity	NPC257430
0.8776	High Similarity	NPC155908
0.875	High Similarity	NPC475245
0.8725	High Similarity	NPC223393
0.8725	High Similarity	NPC211885
0.8725	High Similarity	NPC225506
0.8716	High Similarity	NPC120280
0.8713	High Similarity	NPC225464
0.87	High Similarity	NPC222146
0.8687	High Similarity	NPC94139
0.8687	High Similarity	NPC306884
0.8687	High Similarity	NPC162314
0.8687	High Similarity	NPC147284
0.8687	High Similarity	NPC210497
0.8687	High Similarity	NPC3358
0.8679	High Similarity	NPC233835
0.8673	High Similarity	NPC192
0.8654	High Similarity	NPC79672
0.8654	High Similarity	NPC52087
0.8641	High Similarity	NPC252105
0.8641	High Similarity	NPC471578
0.8641	High Similarity	NPC101025
0.8627	High Similarity	NPC33675
0.8627	High Similarity	NPC252821
0.8627	High Similarity	NPC122005
0.8627	High Similarity	NPC299762
0.8611	High Similarity	NPC297657
0.86	High Similarity	NPC152415
0.8586	High Similarity	NPC304541
0.8586	High Similarity	NPC270547
0.8571	High Similarity	NPC318325
0.8571	High Similarity	NPC280347
0.8571	High Similarity	NPC123273
0.8571	High Similarity	NPC242240
0.8571	High Similarity	NPC47284
0.8571	High Similarity	NPC98772
0.8571	High Similarity	NPC177420
0.8532	High Similarity	NPC471179
0.8515	High Similarity	NPC274678
0.8515	High Similarity	NPC26244
0.8496	Intermediate Similarity	NPC281298
0.8496	Intermediate Similarity	NPC310338
0.8491	Intermediate Similarity	NPC53740
0.8485	Intermediate Similarity	NPC55561
0.8482	Intermediate Similarity	NPC164386
0.8482	Intermediate Similarity	NPC145023
0.8482	Intermediate Similarity	NPC175799
0.8482	Intermediate Similarity	NPC200988
0.8482	Intermediate Similarity	NPC610
0.8469	Intermediate Similarity	NPC25493
0.8469	Intermediate Similarity	NPC113460
0.8469	Intermediate Similarity	NPC27974
0.8455	Intermediate Similarity	NPC471485
0.8448	Intermediate Similarity	NPC53567
0.844	Intermediate Similarity	NPC156840
0.844	Intermediate Similarity	NPC8547
0.844	Intermediate Similarity	NPC257124
0.844	Intermediate Similarity	NPC173746
0.844	Intermediate Similarity	NPC268032
0.8431	Intermediate Similarity	NPC473388
0.8431	Intermediate Similarity	NPC216520
0.8431	Intermediate Similarity	NPC82664
0.8431	Intermediate Similarity	NPC292730
0.8431	Intermediate Similarity	NPC132271
0.8421	Intermediate Similarity	NPC232316
0.8421	Intermediate Similarity	NPC56214
0.8421	Intermediate Similarity	NPC227217
0.8421	Intermediate Similarity	NPC117780
0.8421	Intermediate Similarity	NPC165133
0.8421	Intermediate Similarity	NPC95614
0.8421	Intermediate Similarity	NPC242885
0.8416	Intermediate Similarity	NPC151715
0.8416	Intermediate Similarity	NPC76938
0.8411	Intermediate Similarity	NPC320439
0.8407	Intermediate Similarity	NPC86198
0.8407	Intermediate Similarity	NPC144343
0.8407	Intermediate Similarity	NPC470626
0.84	Intermediate Similarity	NPC306074
0.8384	Intermediate Similarity	NPC258219
0.8381	Intermediate Similarity	NPC269212
0.8381	Intermediate Similarity	NPC477801
0.8381	Intermediate Similarity	NPC477802
0.8367	Intermediate Similarity	NPC23167
0.8367	Intermediate Similarity	NPC184169
0.8365	Intermediate Similarity	NPC48730
0.8365	Intermediate Similarity	NPC129373
0.8365	Intermediate Similarity	NPC72729
0.8365	Intermediate Similarity	NPC248396
0.8362	Intermediate Similarity	NPC321402
0.8362	Intermediate Similarity	NPC471794
0.835	Intermediate Similarity	NPC152097
0.835	Intermediate Similarity	NPC474073
0.835	Intermediate Similarity	NPC77492
0.835	Intermediate Similarity	NPC6597
0.835	Intermediate Similarity	NPC79241
0.8349	Intermediate Similarity	NPC222084
0.8349	Intermediate Similarity	NPC13482
0.8333	Intermediate Similarity	NPC109371
0.8333	Intermediate Similarity	NPC144682
0.8333	Intermediate Similarity	NPC24474
0.8333	Intermediate Similarity	NPC11554
0.8333	Intermediate Similarity	NPC32714
0.8333	Intermediate Similarity	NPC70084
0.8333	Intermediate Similarity	NPC470215
0.8333	Intermediate Similarity	NPC217174
0.8333	Intermediate Similarity	NPC470214
0.8333	Intermediate Similarity	NPC311595
0.8319	Intermediate Similarity	NPC293619
0.8319	Intermediate Similarity	NPC277588
0.8318	Intermediate Similarity	NPC1786
0.8318	Intermediate Similarity	NPC310456
0.8318	Intermediate Similarity	NPC19149
0.8318	Intermediate Similarity	NPC294902
0.8318	Intermediate Similarity	NPC155072
0.8318	Intermediate Similarity	NPC1075
0.8304	Intermediate Similarity	NPC472893
0.8288	Intermediate Similarity	NPC317869
0.8288	Intermediate Similarity	NPC148969
0.8288	Intermediate Similarity	NPC264558
0.8276	Intermediate Similarity	NPC237667
0.8276	Intermediate Similarity	NPC38996
0.8276	Intermediate Similarity	NPC160380
0.8273	Intermediate Similarity	NPC322753
0.8269	Intermediate Similarity	NPC260775
0.8265	Intermediate Similarity	NPC197783
0.8257	Intermediate Similarity	NPC246358
0.8257	Intermediate Similarity	NPC233731
0.8257	Intermediate Similarity	NPC36108
0.8257	Intermediate Similarity	NPC7097
0.8252	Intermediate Similarity	NPC202986
0.8252	Intermediate Similarity	NPC312132
0.8252	Intermediate Similarity	NPC259512
0.8246	Intermediate Similarity	NPC203124
0.8246	Intermediate Similarity	NPC309434
0.8241	Intermediate Similarity	NPC176527
0.8235	Intermediate Similarity	NPC289769
0.8235	Intermediate Similarity	NPC245187
0.823	Intermediate Similarity	NPC299252
0.823	Intermediate Similarity	NPC61062
0.823	Intermediate Similarity	NPC277394
0.8224	Intermediate Similarity	NPC138942
0.822	Intermediate Similarity	NPC15127
0.8218	Intermediate Similarity	NPC45040
0.8214	Intermediate Similarity	NPC142599
0.8208	Intermediate Similarity	NPC302219
0.8208	Intermediate Similarity	NPC242342
0.8208	Intermediate Similarity	NPC71002
0.8208	Intermediate Similarity	NPC313030
0.8208	Intermediate Similarity	NPC94351
0.8208	Intermediate Similarity	NPC249828
0.8208	Intermediate Similarity	NPC146798
0.8208	Intermediate Similarity	NPC62351
0.8208	Intermediate Similarity	NPC108497
0.8208	Intermediate Similarity	NPC168829
0.8208	Intermediate Similarity	NPC53051
0.8208	Intermediate Similarity	NPC85479
0.8208	Intermediate Similarity	NPC24404
0.8208	Intermediate Similarity	NPC106396
0.8208	Intermediate Similarity	NPC222522
0.8208	Intermediate Similarity	NPC168303
0.8205	Intermediate Similarity	NPC85488
0.8198	Intermediate Similarity	NPC250323
0.8198	Intermediate Similarity	NPC51698
0.8198	Intermediate Similarity	NPC228425
0.8198	Intermediate Similarity	NPC146422
0.819	Intermediate Similarity	NPC12931
0.819	Intermediate Similarity	NPC24125
0.819	Intermediate Similarity	NPC207613
0.819	Intermediate Similarity	NPC98305
0.819	Intermediate Similarity	NPC70677
0.819	Intermediate Similarity	NPC130756
0.819	Intermediate Similarity	NPC294741
0.819	Intermediate Similarity	NPC166761
0.819	Intermediate Similarity	NPC10588
0.8182	Intermediate Similarity	NPC141782

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 NPC477814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	1056
0.2-0.3	1481
0.3-0.4	2958
0.4-0.5	1806
0.5-0.6	1110
0.6-0.7	377
0.7-0.8	78
0.8-0.85	11
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.932	High Similarity	NPD3022	Approved
0.932	High Similarity	NPD3021	Approved
0.898	High Similarity	NPD1432	Clinical (unspecified phase)
0.8627	High Similarity	NPD3020	Approved
0.8544	High Similarity	NPD289	Clinical (unspecified phase)
0.8515	High Similarity	NPD2859	Approved
0.8515	High Similarity	NPD2860	Approved
0.844	Intermediate Similarity	NPD228	Approved
0.8416	Intermediate Similarity	NPD2934	Approved
0.8416	Intermediate Similarity	NPD2933	Approved
0.8333	Intermediate Similarity	NPD844	Approved
0.8333	Intermediate Similarity	NPD1809	Phase 2
0.8252	Intermediate Similarity	NPD288	Approved
0.8198	Intermediate Similarity	NPD9379	Approved
0.8198	Intermediate Similarity	NPD9377	Approved
0.8061	Intermediate Similarity	NPD111	Approved
0.7966	Intermediate Similarity	NPD3092	Approved
0.7961	Intermediate Similarity	NPD845	Approved
0.7944	Intermediate Similarity	NPD846	Approved
0.7944	Intermediate Similarity	NPD940	Approved
0.7931	Intermediate Similarity	NPD3091	Approved
0.7857	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD1444	Approved
0.7818	Intermediate Similarity	NPD1445	Approved
0.7807	Intermediate Similarity	NPD5283	Phase 1
0.7797	Intermediate Similarity	NPD4059	Approved
0.7797	Intermediate Similarity	NPD3019	Approved
0.7797	Intermediate Similarity	NPD2932	Approved
0.7768	Intermediate Similarity	NPD4750	Phase 3
0.7705	Intermediate Similarity	NPD3055	Approved
0.7705	Intermediate Similarity	NPD3053	Approved
0.7705	Intermediate Similarity	NPD3094	Phase 2
0.7698	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3620	Phase 2
0.7685	Intermediate Similarity	NPD1242	Phase 1
0.7672	Intermediate Similarity	NPD7157	Approved
0.7652	Intermediate Similarity	NPD2229	Approved
0.7652	Intermediate Similarity	NPD2228	Approved
0.7652	Intermediate Similarity	NPD2234	Approved
0.7647	Intermediate Similarity	NPD9384	Approved
0.7647	Intermediate Similarity	NPD9381	Approved
0.7632	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD5310	Approved
0.7623	Intermediate Similarity	NPD5311	Approved
0.7611	Intermediate Similarity	NPD1792	Phase 2
0.76	Intermediate Similarity	NPD3027	Phase 3
0.7586	Intermediate Similarity	NPD1791	Approved
0.7586	Intermediate Similarity	NPD1793	Approved
0.7565	Intermediate Similarity	NPD7635	Approved
0.7563	Intermediate Similarity	NPD1357	Approved
0.7541	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD9622	Approved
0.754	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD3095	Discontinued
0.75	Intermediate Similarity	NPD257	Approved
0.75	Intermediate Similarity	NPD258	Approved
0.75	Intermediate Similarity	NPD1751	Approved
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2342	Discontinued
0.7417	Intermediate Similarity	NPD4093	Discontinued
0.7377	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6671	Approved
0.7364	Intermediate Similarity	NPD3028	Approved
0.736	Intermediate Similarity	NPD9620	Approved
0.736	Intermediate Similarity	NPD9619	Approved
0.736	Intermediate Similarity	NPD9621	Approved
0.7355	Intermediate Similarity	NPD4589	Approved
0.7344	Intermediate Similarity	NPD2674	Phase 3
0.7321	Intermediate Similarity	NPD9608	Approved
0.7321	Intermediate Similarity	NPD9610	Approved
0.7317	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD8166	Discontinued
0.7302	Intermediate Similarity	NPD5736	Approved
0.7287	Intermediate Similarity	NPD825	Approved
0.7287	Intermediate Similarity	NPD826	Approved
0.7266	Intermediate Similarity	NPD598	Approved
0.7266	Intermediate Similarity	NPD601	Approved
0.7266	Intermediate Similarity	NPD597	Approved
0.7265	Intermediate Similarity	NPD7843	Approved
0.7258	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD9500	Approved
0.7222	Intermediate Similarity	NPD2194	Approved
0.7222	Intermediate Similarity	NPD2195	Approved
0.7213	Intermediate Similarity	NPD2286	Discontinued
0.7213	Intermediate Similarity	NPD4626	Approved
0.7209	Intermediate Similarity	NPD1136	Approved
0.7209	Intermediate Similarity	NPD1130	Approved
0.7209	Intermediate Similarity	NPD1132	Approved
0.7188	Intermediate Similarity	NPD7095	Approved
0.7165	Intermediate Similarity	NPD3637	Approved
0.7165	Intermediate Similarity	NPD3635	Approved
0.7165	Intermediate Similarity	NPD9569	Approved
0.7165	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3636	Approved
0.7154	Intermediate Similarity	NPD3061	Approved
0.7154	Intermediate Similarity	NPD3059	Approved
0.7154	Intermediate Similarity	NPD3062	Approved
0.7154	Intermediate Similarity	NPD3026	Approved
0.7154	Intermediate Similarity	NPD3023	Approved
0.7143	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9094	Approved
0.7132	Intermediate Similarity	NPD3145	Approved
0.7132	Intermediate Similarity	NPD3144	Approved
0.7131	Intermediate Similarity	NPD3025	Approved
0.7131	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD3024	Approved
0.712	Intermediate Similarity	NPD1755	Approved
0.7109	Intermediate Similarity	NPD2605	Approved
0.7109	Intermediate Similarity	NPD2606	Approved
0.7099	Intermediate Similarity	NPD275	Approved
0.7099	Intermediate Similarity	NPD274	Approved
0.709	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4624	Approved
0.7077	Intermediate Similarity	NPD259	Phase 1
0.7077	Intermediate Similarity	NPD6663	Approved
0.7064	Intermediate Similarity	NPD9296	Approved
0.7054	Intermediate Similarity	NPD5156	Approved
0.7054	Intermediate Similarity	NPD5155	Approved
0.7049	Intermediate Similarity	NPD5304	Approved
0.7049	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5303	Approved
0.7045	Intermediate Similarity	NPD817	Approved
0.7045	Intermediate Similarity	NPD823	Approved
0.7045	Intermediate Similarity	NPD5314	Approved
0.7031	Intermediate Similarity	NPD9494	Approved
0.7023	Intermediate Similarity	NPD4060	Phase 1
0.7023	Intermediate Similarity	NPD1558	Phase 1
0.7023	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1613	Approved
0.7023	Intermediate Similarity	NPD943	Approved
0.7016	Intermediate Similarity	NPD3143	Discontinued
0.7009	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9618	Approved
0.7	Intermediate Similarity	NPD9614	Approved
0.7	Intermediate Similarity	NPD475	Phase 2
0.6978	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3645	Discontinued
0.6977	Remote Similarity	NPD3595	Approved
0.6977	Remote Similarity	NPD3594	Approved
0.697	Remote Similarity	NPD5735	Approved
0.697	Remote Similarity	NPD555	Phase 2
0.6967	Remote Similarity	NPD5536	Phase 2
0.6963	Remote Similarity	NPD7266	Discontinued
0.696	Remote Similarity	NPD3705	Approved
0.6953	Remote Similarity	NPD6584	Phase 3
0.6942	Remote Similarity	NPD255	Approved
0.6942	Remote Similarity	NPD256	Approved
0.6939	Remote Similarity	NPD9087	Approved
0.6935	Remote Similarity	NPD2667	Approved
0.6935	Remote Similarity	NPD2668	Approved
0.6935	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6696	Suspended
0.6923	Remote Similarity	NPD9537	Phase 1
0.6923	Remote Similarity	NPD9536	Phase 1
0.6911	Remote Similarity	NPD7330	Discontinued
0.6906	Remote Similarity	NPD2420	Approved
0.6906	Remote Similarity	NPD2421	Approved
0.6905	Remote Similarity	NPD9269	Phase 2
0.6905	Remote Similarity	NPD2232	Approved
0.6905	Remote Similarity	NPD2233	Approved
0.6905	Remote Similarity	NPD2230	Approved
0.6905	Remote Similarity	NPD3070	Discontinued
0.6899	Remote Similarity	NPD2861	Phase 2
0.6889	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9273	Approved
0.6864	Remote Similarity	NPD5451	Approved
0.6855	Remote Similarity	NPD5691	Approved
0.685	Remote Similarity	NPD4749	Approved
0.685	Remote Similarity	NPD5327	Phase 3
0.6838	Remote Similarity	NPD290	Approved
0.6835	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3845	Phase 1
0.6833	Remote Similarity	NPD821	Approved
0.6832	Remote Similarity	NPD9088	Approved
0.6829	Remote Similarity	NPD9615	Approved
0.6829	Remote Similarity	NPD856	Approved
0.6829	Remote Similarity	NPD9613	Approved
0.6829	Remote Similarity	NPD9616	Approved
0.6829	Remote Similarity	NPD16	Approved
0.6822	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7743	Approved
0.6815	Remote Similarity	NPD7742	Approved
0.6815	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4110	Phase 3
0.6812	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8651	Approved
0.6791	Remote Similarity	NPD4097	Suspended
0.6777	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD316	Approved
0.6767	Remote Similarity	NPD6346	Approved
0.6767	Remote Similarity	NPD4140	Approved
0.6765	Remote Similarity	NPD2161	Phase 2
0.6752	Remote Similarity	NPD968	Approved
0.6748	Remote Similarity	NPD7325	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