NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.1
Volume:	250.009
LogP:	3.052
LogD:	3.208
LogS:	-2.76
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	2.726
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.659
MDCK Permeability:	2.2971198632149026e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.405
30% Bioavailability (F30%):	0.402

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	98.1641616821289%
Volume Distribution (VD):	0.565
Pgp-substrate:	1.2255579233169556%

ADMET: Metabolism

CYP1A2-inhibitor:	0.632
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.762
CYP2C19-substrate:	0.201
CYP2C9-inhibitor:	0.657
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.913
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.39
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	15.484
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.606
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.893
Carcinogencity:	0.486
Eye Corrosion:	0.019
Eye Irritation:	0.934
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC239291

Natural Product ID:	NPC239291
*Common Name:**	(S)-4-(1-Phenylallyl)Benzene-1,2-Diol
IUPAC Name:	4-[(1S)-1-phenylprop-2-enyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	OTJLSKLGXRCVFQ-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C15H14O2/c1-2-13(11-6-4-3-5-7-11)12-8-9-14(16)15(17)10-12/h2-10,13,16-17H,1H2/t13-/m0/s1
SMILES:	C=C[C@H](c1ccc(c(c1)O)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443965
PubChem CID:	11333614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO29804	Nepalese propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15974608]

☑ 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	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	8400.0	nM	PMID[458387]

☑ 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 NPC239291 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	403
0.1-0.2	2036
0.2-0.3	5853
0.3-0.4	13126
0.4-0.5	5120
0.5-0.6	9050
0.6-0.7	4999
0.7-0.8	1810
0.8-0.85	222
0.85-0.9	53
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9694	High Similarity	NPC471511
0.9604	High Similarity	NPC228343
0.9604	High Similarity	NPC254833
0.9388	High Similarity	NPC223393
0.9381	High Similarity	NPC109955
0.9314	High Similarity	NPC233835
0.93	High Similarity	NPC120719
0.9223	High Similarity	NPC62258
0.9223	High Similarity	NPC55617
0.9175	High Similarity	NPC274678
0.9151	High Similarity	NPC120280
0.9135	High Similarity	NPC174096
0.9135	High Similarity	NPC226401
0.9135	High Similarity	NPC120982
0.9135	High Similarity	NPC79793
0.9135	High Similarity	NPC147634
0.9118	High Similarity	NPC477814
0.91	High Similarity	NPC110764
0.9057	High Similarity	NPC471485
0.9048	High Similarity	NPC268032
0.9048	High Similarity	NPC187583
0.9048	High Similarity	NPC257430
0.9048	High Similarity	NPC179002
0.901	High Similarity	NPC196479
0.898	High Similarity	NPC107522
0.8922	High Similarity	NPC12278
0.89	High Similarity	NPC131587
0.8889	High Similarity	NPC216520
0.8889	High Similarity	NPC82664
0.8889	High Similarity	NPC132271
0.8889	High Similarity	NPC292730
0.8868	High Similarity	NPC297657
0.8866	High Similarity	NPC45040
0.8846	High Similarity	NPC176527
0.88	High Similarity	NPC32674
0.8785	High Similarity	NPC471179
0.8762	High Similarity	NPC58427
0.8762	High Similarity	NPC105727
0.8762	High Similarity	NPC34864
0.8762	High Similarity	NPC114392
0.8739	High Similarity	NPC281298
0.8739	High Similarity	NPC310338
0.8725	High Similarity	NPC12221
0.8716	High Similarity	NPC472893
0.8713	High Similarity	NPC92730
0.87	High Similarity	NPC473388
0.8687	High Similarity	NPC76938
0.8687	High Similarity	NPC128062
0.8687	High Similarity	NPC151715
0.8673	High Similarity	NPC304541
0.8661	High Similarity	NPC242885
0.8661	High Similarity	NPC95614
0.8661	High Similarity	NPC165133
0.8661	High Similarity	NPC232316
0.8661	High Similarity	NPC56214
0.8661	High Similarity	NPC227217
0.8661	High Similarity	NPC117780
0.8614	High Similarity	NPC225464
0.86	High Similarity	NPC26244
0.86	High Similarity	NPC32714
0.8585	High Similarity	NPC11554
0.8571	High Similarity	NPC176893
0.8571	High Similarity	NPC54765
0.8559	High Similarity	NPC16030
0.8559	High Similarity	NPC175799
0.8559	High Similarity	NPC610
0.8559	High Similarity	NPC278652
0.8559	High Similarity	NPC145023
0.8559	High Similarity	NPC200988
0.8559	High Similarity	NPC293619
0.8558	High Similarity	NPC323810
0.8558	High Similarity	NPC52087
0.8558	High Similarity	NPC254965
0.8558	High Similarity	NPC30506
0.8558	High Similarity	NPC327811
0.8558	High Similarity	NPC79672
0.8509	High Similarity	NPC38996
0.8509	High Similarity	NPC160380
0.8496	Intermediate Similarity	NPC472071
0.8496	Intermediate Similarity	NPC475245
0.8482	Intermediate Similarity	NPC470626
0.8482	Intermediate Similarity	NPC86198
0.8482	Intermediate Similarity	NPC144343
0.8469	Intermediate Similarity	NPC258219
0.8468	Intermediate Similarity	NPC277394
0.8468	Intermediate Similarity	NPC61062
0.8468	Intermediate Similarity	NPC299252
0.8462	Intermediate Similarity	NPC477802
0.8462	Intermediate Similarity	NPC477801
0.8462	Intermediate Similarity	NPC168829
0.8447	Intermediate Similarity	NPC294741
0.844	Intermediate Similarity	NPC51698
0.8435	Intermediate Similarity	NPC85488
0.8431	Intermediate Similarity	NPC156313
0.8426	Intermediate Similarity	NPC222084
0.8421	Intermediate Similarity	NPC470414
0.8411	Intermediate Similarity	NPC95344
0.8407	Intermediate Similarity	NPC217174
0.8407	Intermediate Similarity	NPC470214
0.8407	Intermediate Similarity	NPC70084
0.8407	Intermediate Similarity	NPC470215
0.8407	Intermediate Similarity	NPC109371
0.84	Intermediate Similarity	NPC55903
0.84	Intermediate Similarity	NPC271440
0.8396	Intermediate Similarity	NPC1075
0.8396	Intermediate Similarity	NPC19149
0.8396	Intermediate Similarity	NPC248904
0.8396	Intermediate Similarity	NPC294902
0.8396	Intermediate Similarity	NPC1786
0.8393	Intermediate Similarity	NPC86947
0.8393	Intermediate Similarity	NPC277588
0.8384	Intermediate Similarity	NPC192
0.8381	Intermediate Similarity	NPC288411
0.8367	Intermediate Similarity	NPC27974
0.8365	Intermediate Similarity	NPC143659
0.8365	Intermediate Similarity	NPC100340
0.8364	Intermediate Similarity	NPC317869
0.8362	Intermediate Similarity	NPC31344
0.8362	Intermediate Similarity	NPC473451
0.8362	Intermediate Similarity	NPC317769
0.8362	Intermediate Similarity	NPC280704
0.835	Intermediate Similarity	NPC51333
0.835	Intermediate Similarity	NPC132078
0.835	Intermediate Similarity	NPC78119
0.835	Intermediate Similarity	NPC216468
0.8349	Intermediate Similarity	NPC173746
0.8349	Intermediate Similarity	NPC8547
0.8349	Intermediate Similarity	NPC156840
0.8349	Intermediate Similarity	NPC257124
0.8348	Intermediate Similarity	NPC237667
0.8333	Intermediate Similarity	NPC265454
0.8333	Intermediate Similarity	NPC312132
0.8333	Intermediate Similarity	NPC202986
0.8333	Intermediate Similarity	NPC259512
0.8333	Intermediate Similarity	NPC34634
0.8333	Intermediate Similarity	NPC58865
0.8317	Intermediate Similarity	NPC316301
0.8317	Intermediate Similarity	NPC27323
0.8302	Intermediate Similarity	NPC138942
0.83	Intermediate Similarity	NPC155908
0.8291	Intermediate Similarity	NPC257682
0.8291	Intermediate Similarity	NPC146355
0.8291	Intermediate Similarity	NPC131747
0.8286	Intermediate Similarity	NPC168393
0.8286	Intermediate Similarity	NPC233827
0.8283	Intermediate Similarity	NPC318325
0.8283	Intermediate Similarity	NPC242240
0.8283	Intermediate Similarity	NPC123273
0.8273	Intermediate Similarity	NPC146422
0.8269	Intermediate Similarity	NPC213730
0.8269	Intermediate Similarity	NPC275053
0.8269	Intermediate Similarity	NPC72729
0.8269	Intermediate Similarity	NPC161571
0.8269	Intermediate Similarity	NPC248573
0.8265	Intermediate Similarity	NPC23167
0.8261	Intermediate Similarity	NPC24125
0.8261	Intermediate Similarity	NPC98305
0.8261	Intermediate Similarity	NPC207613
0.8257	Intermediate Similarity	NPC44732
0.8252	Intermediate Similarity	NPC6597
0.8252	Intermediate Similarity	NPC79241
0.8252	Intermediate Similarity	NPC77492
0.8247	Intermediate Similarity	NPC175313
0.8246	Intermediate Similarity	NPC263386
0.8246	Intermediate Similarity	NPC268572
0.8246	Intermediate Similarity	NPC191866
0.8246	Intermediate Similarity	NPC38483
0.8246	Intermediate Similarity	NPC141791
0.8241	Intermediate Similarity	NPC75440
0.8235	Intermediate Similarity	NPC8392
0.823	Intermediate Similarity	NPC283468
0.8224	Intermediate Similarity	NPC271274
0.822	Intermediate Similarity	NPC148627
0.822	Intermediate Similarity	NPC9067
0.822	Intermediate Similarity	NPC228771
0.822	Intermediate Similarity	NPC266705
0.822	Intermediate Similarity	NPC29008
0.8218	Intermediate Similarity	NPC94139
0.8218	Intermediate Similarity	NPC306884
0.8218	Intermediate Similarity	NPC147284
0.8218	Intermediate Similarity	NPC162314
0.8218	Intermediate Similarity	NPC3358
0.8218	Intermediate Similarity	NPC210497
0.8208	Intermediate Similarity	NPC241891
0.8208	Intermediate Similarity	NPC102216
0.8205	Intermediate Similarity	NPC53567
0.8205	Intermediate Similarity	NPC84086
0.82	Intermediate Similarity	NPC300017
0.8198	Intermediate Similarity	NPC264558
0.8198	Intermediate Similarity	NPC148969
0.819	Intermediate Similarity	NPC40258
0.819	Intermediate Similarity	NPC470212
0.819	Intermediate Similarity	NPC324571
0.819	Intermediate Similarity	NPC54872
0.819	Intermediate Similarity	NPC312675
0.819	Intermediate Similarity	NPC127389
0.819	Intermediate Similarity	NPC473853
0.819	Intermediate Similarity	NPC39029
0.819	Intermediate Similarity	NPC113865
0.819	Intermediate Similarity	NPC262156

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 NPC239291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1031
0.2-0.3	1330
0.3-0.4	2963
0.4-0.5	1837
0.5-0.6	1091
0.6-0.7	408
0.7-0.8	74
0.8-0.85	8
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9604	High Similarity	NPD3022	Approved
0.9604	High Similarity	NPD3021	Approved
0.89	High Similarity	NPD3020	Approved
0.86	High Similarity	NPD2859	Approved
0.86	High Similarity	NPD2860	Approved
0.85	High Similarity	NPD2934	Approved
0.85	High Similarity	NPD2933	Approved
0.8349	Intermediate Similarity	NPD228	Approved
0.8333	Intermediate Similarity	NPD288	Approved
0.8317	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD9379	Approved
0.8273	Intermediate Similarity	NPD9377	Approved
0.8269	Intermediate Similarity	NPD1242	Phase 1
0.8095	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD844	Approved
0.8036	Intermediate Similarity	NPD5283	Phase 1
0.7959	Intermediate Similarity	NPD111	Approved
0.7928	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD845	Approved
0.7838	Intermediate Similarity	NPD1792	Phase 2
0.7833	Intermediate Similarity	NPD5310	Approved
0.7833	Intermediate Similarity	NPD5311	Approved
0.7818	Intermediate Similarity	NPD2342	Discontinued
0.7788	Intermediate Similarity	NPD7635	Approved
0.7769	Intermediate Similarity	NPD3055	Approved
0.7769	Intermediate Similarity	NPD3053	Approved
0.7731	Intermediate Similarity	NPD3092	Approved
0.7727	Intermediate Similarity	NPD1444	Approved
0.7727	Intermediate Similarity	NPD1445	Approved
0.7724	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2229	Approved
0.7719	Intermediate Similarity	NPD2228	Approved
0.7719	Intermediate Similarity	NPD2234	Approved
0.7714	Intermediate Similarity	NPD1809	Phase 2
0.7712	Intermediate Similarity	NPD9384	Approved
0.7712	Intermediate Similarity	NPD9381	Approved
0.7692	Intermediate Similarity	NPD3091	Approved
0.7685	Intermediate Similarity	NPD846	Approved
0.7685	Intermediate Similarity	NPD940	Approved
0.7679	Intermediate Similarity	NPD4750	Phase 3
0.7667	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3027	Phase 3
0.7642	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4093	Discontinued
0.7603	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD3019	Approved
0.7563	Intermediate Similarity	NPD4059	Approved
0.7563	Intermediate Similarity	NPD2286	Discontinued
0.7563	Intermediate Similarity	NPD2932	Approved
0.748	Intermediate Similarity	NPD3620	Phase 2
0.748	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD943	Approved
0.748	Intermediate Similarity	NPD3094	Phase 2
0.748	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD1613	Approved
0.7462	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD9622	Approved
0.7459	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3028	Approved
0.7419	Intermediate Similarity	NPD258	Approved
0.7419	Intermediate Similarity	NPD257	Approved
0.7417	Intermediate Similarity	NPD1751	Approved
0.7398	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD3061	Approved
0.7344	Intermediate Similarity	NPD3062	Approved
0.7344	Intermediate Similarity	NPD1558	Phase 1
0.7344	Intermediate Similarity	NPD3059	Approved
0.7295	Intermediate Similarity	NPD1610	Phase 2
0.728	Intermediate Similarity	NPD9621	Approved
0.728	Intermediate Similarity	NPD9620	Approved
0.728	Intermediate Similarity	NPD9619	Approved
0.7273	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3095	Discontinued
0.7257	Intermediate Similarity	NPD968	Approved
0.725	Intermediate Similarity	NPD5304	Approved
0.725	Intermediate Similarity	NPD5303	Approved
0.7232	Intermediate Similarity	NPD9610	Approved
0.7232	Intermediate Similarity	NPD9608	Approved
0.7231	Intermediate Similarity	NPD5314	Approved
0.7222	Intermediate Similarity	NPD2861	Phase 2
0.7222	Intermediate Similarity	NPD9569	Approved
0.7212	Intermediate Similarity	NPD9094	Approved
0.7209	Intermediate Similarity	NPD4060	Phase 1
0.72	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1201	Approved
0.7154	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD9500	Approved
0.7132	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4589	Approved
0.7131	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD2684	Approved
0.712	Intermediate Similarity	NPD1283	Approved
0.7111	Intermediate Similarity	NPD8166	Discontinued
0.7099	Intermediate Similarity	NPD823	Approved
0.7099	Intermediate Similarity	NPD817	Approved
0.7087	Intermediate Similarity	NPD5736	Approved
0.7077	Intermediate Similarity	NPD826	Approved
0.7077	Intermediate Similarity	NPD825	Approved
0.7069	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD475	Phase 2
0.7059	Intermediate Similarity	NPD1793	Approved
0.7059	Intermediate Similarity	NPD497	Approved
0.7059	Intermediate Similarity	NPD1791	Approved
0.7054	Intermediate Similarity	NPD598	Approved
0.7054	Intermediate Similarity	NPD601	Approved
0.7054	Intermediate Similarity	NPD597	Approved
0.7049	Intermediate Similarity	NPD1357	Approved
0.7025	Intermediate Similarity	NPD5536	Phase 2
0.7023	Intermediate Similarity	NPD274	Approved
0.7023	Intermediate Similarity	NPD275	Approved
0.7015	Intermediate Similarity	NPD7266	Discontinued
0.701	Intermediate Similarity	NPD9087	Approved
0.7008	Intermediate Similarity	NPD6584	Phase 3
0.7008	Intermediate Similarity	NPD2195	Approved
0.7008	Intermediate Similarity	NPD2194	Approved
0.7007	Intermediate Similarity	NPD3845	Phase 1
0.7	Intermediate Similarity	NPD259	Phase 1
0.7	Intermediate Similarity	NPD2674	Phase 3
0.7	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD1136	Approved
0.7	Intermediate Similarity	NPD7157	Approved
0.7	Intermediate Similarity	NPD1132	Approved
0.7	Intermediate Similarity	NPD1130	Approved
0.6992	Remote Similarity	NPD2668	Approved
0.6992	Remote Similarity	NPD2667	Approved
0.6977	Remote Similarity	NPD7095	Approved
0.6977	Remote Similarity	NPD9536	Phase 1
0.6977	Remote Similarity	NPD9537	Phase 1
0.6977	Remote Similarity	NPD5155	Approved
0.6977	Remote Similarity	NPD5156	Approved
0.6975	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD495	Approved
0.6975	Remote Similarity	NPD496	Approved
0.6975	Remote Similarity	NPD498	Approved
0.6972	Remote Similarity	NPD9296	Approved
0.6967	Remote Similarity	NPD1548	Phase 1
0.6967	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2232	Approved
0.696	Remote Similarity	NPD9269	Phase 2
0.696	Remote Similarity	NPD2233	Approved
0.696	Remote Similarity	NPD2230	Approved
0.696	Remote Similarity	NPD1608	Approved
0.6957	Remote Similarity	NPD2420	Approved
0.6957	Remote Similarity	NPD2421	Approved
0.6953	Remote Similarity	NPD9494	Approved
0.6953	Remote Similarity	NPD3636	Approved
0.6953	Remote Similarity	NPD3635	Approved
0.6953	Remote Similarity	NPD3637	Approved
0.6949	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD9273	Approved
0.6935	Remote Similarity	NPD3026	Approved
0.6935	Remote Similarity	NPD3023	Approved
0.6929	Remote Similarity	NPD1164	Approved
0.6929	Remote Similarity	NPD1470	Approved
0.6923	Remote Similarity	NPD5451	Approved
0.6923	Remote Similarity	NPD3145	Approved
0.6923	Remote Similarity	NPD5109	Approved
0.6923	Remote Similarity	NPD5111	Phase 2
0.6923	Remote Similarity	NPD5110	Phase 2
0.6923	Remote Similarity	NPD3144	Approved
0.6917	Remote Similarity	NPD9618	Approved
0.6917	Remote Similarity	NPD9614	Approved
0.6911	Remote Similarity	NPD3025	Approved
0.6911	Remote Similarity	NPD1651	Approved
0.6911	Remote Similarity	NPD3024	Approved
0.6906	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4659	Approved
0.6905	Remote Similarity	NPD1669	Approved
0.69	Remote Similarity	NPD9088	Approved
0.6899	Remote Similarity	NPD2606	Approved
0.6899	Remote Similarity	NPD3594	Approved
0.6899	Remote Similarity	NPD4908	Phase 1
0.6899	Remote Similarity	NPD2605	Approved
0.6899	Remote Similarity	NPD3595	Approved
0.6894	Remote Similarity	NPD555	Phase 2
0.6891	Remote Similarity	NPD7843	Approved
0.688	Remote Similarity	NPD1281	Approved
0.6879	Remote Similarity	NPD1972	Approved
0.6879	Remote Similarity	NPD1973	Approved
0.6879	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4624	Approved
0.687	Remote Similarity	NPD6663	Approved
0.6866	Remote Similarity	NPD651	Clinical (unspecified phase)
0.686	Remote Similarity	NPD255	Approved
0.686	Remote Similarity	NPD256	Approved
0.6855	Remote Similarity	NPD4626	Approved
0.6855	Remote Similarity	NPD5846	Approved
0.6855	Remote Similarity	NPD6516	Phase 2
0.6842	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD1616	Discontinued
0.68	Remote Similarity	NPD9294	Approved
0.6797	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4103	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