NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	330.0
Volume:	298.278
LogP:	5.392
LogD:	3.865
LogS:	-6.267
# Rotatable Bonds:	4
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.84
Synthetic Accessibility Score:	2.096
Fsp3:	0.2
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:	-4.911
MDCK Permeability:	1.308503942709649e-05
Pgp-inhibitor:	0.911
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272
Plasma Protein Binding (PPB):	100.18309783935547%
Volume Distribution (VD):	2.456
Pgp-substrate:	1.2393181324005127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.18
CYP2C9-inhibitor:	0.929
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.74
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.453
CYP3A4-substrate:	0.716

ADMET: Excretion

Clearance (CL):	8.73
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.84
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.768
Skin Sensitization:	0.671
Carcinogencity:	0.244
Eye Corrosion:	0.012
Eye Irritation:	0.818
Respiratory Toxicity:	0.424

Download Data

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

Natural Product: NPC246991

Natural Product ID:	NPC246991
*Common Name:**	2,6,3-Trichloro-3-Hydroxy-4-Methoxybibenzyl
IUPAC Name:	2,4-dichloro-3-[2-(3-chloro-4-methoxyphenyl)ethyl]phenol
Synonyms:
Standard InCHIKey:	PBAYBNJYAVRJHR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13Cl3O2/c1-20-14-7-3-9(8-12(14)17)2-4-10-11(16)5-6-13(19)15(10)18/h3,5-8,19H,2,4H2,1H3
SMILES:	COc1ccc(cc1Cl)CCc1c(Cl)ccc(c1Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249637
PubChem CID:	24762920
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO33135	riccardia polyclada	Species	Aneuraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18020419]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.42	ppm	PMID[538264]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	FR50	=	0.63	n.a.	PMID[538264]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	IZ	=	12.0	mm	PMID[538264]

☑ 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 NPC246991 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	547
0.1-0.2	2834
0.2-0.3	11446
0.3-0.4	8298
0.4-0.5	6055
0.5-0.6	10354
0.6-0.7	2991
0.7-0.8	164
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC139335
0.9754	High Similarity	NPC8058
0.888	High Similarity	NPC42644
0.8468	Intermediate Similarity	NPC244403
0.8306	Intermediate Similarity	NPC91452
0.8197	Intermediate Similarity	NPC146096
0.8049	Intermediate Similarity	NPC75440
0.7956	Intermediate Similarity	NPC193334
0.7869	Intermediate Similarity	NPC12987
0.7869	Intermediate Similarity	NPC474603
0.7867	Intermediate Similarity	NPC56379
0.7836	Intermediate Similarity	NPC33402
0.7778	Intermediate Similarity	NPC182475
0.7742	Intermediate Similarity	NPC113457
0.7727	Intermediate Similarity	NPC67791
0.7643	Intermediate Similarity	NPC76453
0.7619	Intermediate Similarity	NPC201959
0.7586	Intermediate Similarity	NPC131379
0.7569	Intermediate Similarity	NPC86087
0.7557	Intermediate Similarity	NPC141090
0.7536	Intermediate Similarity	NPC26576
0.75	Intermediate Similarity	NPC474933
0.75	Intermediate Similarity	NPC293619
0.75	Intermediate Similarity	NPC195466
0.75	Intermediate Similarity	NPC30390
0.7481	Intermediate Similarity	NPC14287
0.7462	Intermediate Similarity	NPC35344
0.7462	Intermediate Similarity	NPC141003
0.7444	Intermediate Similarity	NPC470626
0.7442	Intermediate Similarity	NPC90520
0.7442	Intermediate Similarity	NPC296920
0.7419	Intermediate Similarity	NPC300166
0.7407	Intermediate Similarity	NPC205213
0.7405	Intermediate Similarity	NPC276737
0.7405	Intermediate Similarity	NPC22610
0.7397	Intermediate Similarity	NPC252901
0.7388	Intermediate Similarity	NPC281298
0.7388	Intermediate Similarity	NPC310338
0.7385	Intermediate Similarity	NPC280606
0.7364	Intermediate Similarity	NPC43411
0.7348	Intermediate Similarity	NPC53906
0.7348	Intermediate Similarity	NPC808
0.7348	Intermediate Similarity	NPC167934
0.7333	Intermediate Similarity	NPC103916
0.7333	Intermediate Similarity	NPC242885
0.7333	Intermediate Similarity	NPC117780
0.7333	Intermediate Similarity	NPC227217
0.7333	Intermediate Similarity	NPC56214
0.7333	Intermediate Similarity	NPC95614
0.7333	Intermediate Similarity	NPC165133
0.7333	Intermediate Similarity	NPC232316
0.7319	Intermediate Similarity	NPC235370
0.7308	Intermediate Similarity	NPC8547
0.7308	Intermediate Similarity	NPC156840
0.7308	Intermediate Similarity	NPC173746
0.7308	Intermediate Similarity	NPC257124
0.7305	Intermediate Similarity	NPC185313
0.7302	Intermediate Similarity	NPC241224
0.7299	Intermediate Similarity	NPC90577
0.7299	Intermediate Similarity	NPC151237
0.7295	Intermediate Similarity	NPC274678
0.7293	Intermediate Similarity	NPC203113
0.7293	Intermediate Similarity	NPC150624
0.7287	Intermediate Similarity	NPC474272
0.7279	Intermediate Similarity	NPC129176
0.7279	Intermediate Similarity	NPC207613
0.7273	Intermediate Similarity	NPC45072
0.7273	Intermediate Similarity	NPC180508
0.7273	Intermediate Similarity	NPC228287
0.7266	Intermediate Similarity	NPC233320
0.7258	Intermediate Similarity	NPC100870
0.7256	Intermediate Similarity	NPC470422
0.7239	Intermediate Similarity	NPC244816
0.7239	Intermediate Similarity	NPC127894
0.7239	Intermediate Similarity	NPC15860
0.7239	Intermediate Similarity	NPC50521
0.7239	Intermediate Similarity	NPC470759
0.7239	Intermediate Similarity	NPC219070
0.7239	Intermediate Similarity	NPC69261
0.7239	Intermediate Similarity	NPC33270
0.7239	Intermediate Similarity	NPC221549
0.7231	Intermediate Similarity	NPC475852
0.7231	Intermediate Similarity	NPC94045
0.7229	Intermediate Similarity	NPC474498
0.7226	Intermediate Similarity	NPC312675
0.7226	Intermediate Similarity	NPC113865
0.7226	Intermediate Similarity	NPC476633
0.7226	Intermediate Similarity	NPC160380
0.7226	Intermediate Similarity	NPC184651
0.7226	Intermediate Similarity	NPC38996
0.7226	Intermediate Similarity	NPC54872
0.7226	Intermediate Similarity	NPC343720
0.7226	Intermediate Similarity	NPC470212
0.7226	Intermediate Similarity	NPC262156
0.7226	Intermediate Similarity	NPC473853
0.7226	Intermediate Similarity	NPC324571
0.7185	Intermediate Similarity	NPC15350
0.7185	Intermediate Similarity	NPC63010
0.7185	Intermediate Similarity	NPC474040
0.7185	Intermediate Similarity	NPC190514
0.7185	Intermediate Similarity	NPC474214
0.7176	Intermediate Similarity	NPC275627
0.7174	Intermediate Similarity	NPC30462
0.7174	Intermediate Similarity	NPC41562
0.7174	Intermediate Similarity	NPC85488
0.7164	Intermediate Similarity	NPC85292
0.7164	Intermediate Similarity	NPC229147
0.7164	Intermediate Similarity	NPC114064
0.7164	Intermediate Similarity	NPC54507
0.7154	Intermediate Similarity	NPC246358
0.7154	Intermediate Similarity	NPC7097
0.7154	Intermediate Similarity	NPC233731
0.7154	Intermediate Similarity	NPC36108
0.7153	Intermediate Similarity	NPC102639
0.7143	Intermediate Similarity	NPC475423
0.7132	Intermediate Similarity	NPC474320
0.7132	Intermediate Similarity	NPC184302
0.7122	Intermediate Similarity	NPC471693
0.7122	Intermediate Similarity	NPC136319
0.7122	Intermediate Similarity	NPC282496
0.7122	Intermediate Similarity	NPC84086
0.7122	Intermediate Similarity	NPC249788
0.7122	Intermediate Similarity	NPC197757
0.7122	Intermediate Similarity	NPC228922
0.7122	Intermediate Similarity	NPC233526
0.7122	Intermediate Similarity	NPC317769
0.7122	Intermediate Similarity	NPC31344
0.7122	Intermediate Similarity	NPC280704
0.7111	Intermediate Similarity	NPC86947
0.7111	Intermediate Similarity	NPC164386
0.7109	Intermediate Similarity	NPC233396
0.7109	Intermediate Similarity	NPC154899
0.7101	Intermediate Similarity	NPC127389
0.7101	Intermediate Similarity	NPC290451
0.7099	Intermediate Similarity	NPC168657
0.7099	Intermediate Similarity	NPC137685
0.709	Intermediate Similarity	NPC185541
0.709	Intermediate Similarity	NPC296526
0.709	Intermediate Similarity	NPC464
0.7087	Intermediate Similarity	NPC305205
0.7071	Intermediate Similarity	NPC228503
0.7071	Intermediate Similarity	NPC5796
0.7071	Intermediate Similarity	NPC138248
0.7071	Intermediate Similarity	NPC206487
0.7068	Intermediate Similarity	NPC165106
0.7059	Intermediate Similarity	NPC131118
0.7054	Intermediate Similarity	NPC92623
0.7054	Intermediate Similarity	NPC135464
0.7049	Intermediate Similarity	NPC322888
0.7049	Intermediate Similarity	NPC45040
0.7049	Intermediate Similarity	NPC321956
0.7045	Intermediate Similarity	NPC139617
0.7045	Intermediate Similarity	NPC78918
0.7045	Intermediate Similarity	NPC195873
0.704	Intermediate Similarity	NPC470161
0.7037	Intermediate Similarity	NPC221049
0.7037	Intermediate Similarity	NPC19290
0.7034	Intermediate Similarity	NPC66643
0.7031	Intermediate Similarity	NPC38079
0.7031	Intermediate Similarity	NPC292792
0.7031	Intermediate Similarity	NPC108875
0.703	Intermediate Similarity	NPC277865
0.7029	Intermediate Similarity	NPC277798
0.7029	Intermediate Similarity	NPC131868
0.7029	Intermediate Similarity	NPC100108
0.7021	Intermediate Similarity	NPC9067
0.7021	Intermediate Similarity	NPC193544
0.7021	Intermediate Similarity	NPC203133
0.7021	Intermediate Similarity	NPC148627
0.7021	Intermediate Similarity	NPC17943
0.7021	Intermediate Similarity	NPC475169
0.7021	Intermediate Similarity	NPC208950
0.7021	Intermediate Similarity	NPC105925
0.7021	Intermediate Similarity	NPC298757
0.7021	Intermediate Similarity	NPC472093
0.7021	Intermediate Similarity	NPC117214
0.7021	Intermediate Similarity	NPC266705
0.7021	Intermediate Similarity	NPC116907
0.7021	Intermediate Similarity	NPC105031
0.7021	Intermediate Similarity	NPC113495
0.7021	Intermediate Similarity	NPC221077
0.7021	Intermediate Similarity	NPC257589
0.7021	Intermediate Similarity	NPC53305
0.7021	Intermediate Similarity	NPC29008
0.7021	Intermediate Similarity	NPC233410
0.7021	Intermediate Similarity	NPC57490
0.7021	Intermediate Similarity	NPC251855
0.7021	Intermediate Similarity	NPC105718
0.7021	Intermediate Similarity	NPC278955
0.7021	Intermediate Similarity	NPC228771
0.7016	Intermediate Similarity	NPC26244
0.7015	Intermediate Similarity	NPC470837
0.7007	Intermediate Similarity	NPC226629
0.7007	Intermediate Similarity	NPC311595
0.7007	Intermediate Similarity	NPC24474
0.7	Intermediate Similarity	NPC227894
0.7	Intermediate Similarity	NPC251306
0.6992	Remote Similarity	NPC98372
0.6988	Remote Similarity	NPC474857
0.6985	Remote Similarity	NPC161768

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 NPC246991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	480
0.1-0.2	1103
0.2-0.3	1832
0.3-0.4	2715
0.4-0.5	1756
0.5-0.6	1003
0.6-0.7	241
0.7-0.8	19
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8014	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1184	Approved
0.7664	Intermediate Similarity	NPD454	Approved
0.7594	Intermediate Similarity	NPD4589	Approved
0.7559	Intermediate Similarity	NPD5451	Approved
0.7556	Intermediate Similarity	NPD1157	Approved
0.7538	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9500	Approved
0.7407	Intermediate Similarity	NPD915	Approved
0.7383	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7041	Phase 2
0.7361	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4538	Approved
0.7361	Intermediate Similarity	NPD4536	Approved
0.7308	Intermediate Similarity	NPD228	Approved
0.7192	Intermediate Similarity	NPD5960	Phase 3
0.7192	Intermediate Similarity	NPD5588	Approved
0.717	Intermediate Similarity	NPD3365	Discontinued
0.7152	Intermediate Similarity	NPD3303	Discontinued
0.7122	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1578	Phase 2
0.708	Intermediate Similarity	NPD5846	Approved
0.708	Intermediate Similarity	NPD6516	Phase 2
0.7068	Intermediate Similarity	NPD5283	Phase 1
0.7067	Intermediate Similarity	NPD4535	Phase 3
0.7054	Intermediate Similarity	NPD968	Approved
0.7047	Intermediate Similarity	NPD2808	Discontinued
0.7016	Intermediate Similarity	NPD2859	Approved
0.7016	Intermediate Similarity	NPD2860	Approved
0.6984	Remote Similarity	NPD3020	Approved
0.6974	Remote Similarity	NPD5058	Phase 3
0.6972	Remote Similarity	NPD6584	Phase 3
0.6963	Remote Similarity	NPD6671	Approved
0.6935	Remote Similarity	NPD2933	Approved
0.6935	Remote Similarity	NPD2934	Approved
0.6933	Remote Similarity	NPD4534	Discontinued
0.6929	Remote Similarity	NPD1616	Discontinued
0.6863	Remote Similarity	NPD6815	Approved
0.6857	Remote Similarity	NPD1610	Phase 2
0.6831	Remote Similarity	NPD1283	Approved
0.6828	Remote Similarity	NPD3027	Phase 3
0.6824	Remote Similarity	NPD2986	Phase 2
0.6824	Remote Similarity	NPD2989	Phase 2
0.6821	Remote Similarity	NPD5958	Discontinued
0.6818	Remote Similarity	NPD2684	Approved
0.6812	Remote Similarity	NPD1548	Phase 1
0.6806	Remote Similarity	NPD2861	Phase 2
0.68	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD987	Approved
0.6772	Remote Similarity	NPD1715	Phase 1
0.6772	Remote Similarity	NPD1714	Approved
0.6769	Remote Similarity	NPD9501	Approved
0.6767	Remote Similarity	NPD3022	Approved
0.6767	Remote Similarity	NPD3021	Approved
0.6763	Remote Similarity	NPD1651	Approved
0.6761	Remote Similarity	NPD6583	Phase 3
0.6761	Remote Similarity	NPD1669	Approved
0.6761	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6582	Phase 2
0.6742	Remote Similarity	NPD9552	Approved
0.673	Remote Similarity	NPD958	Approved
0.6715	Remote Similarity	NPD709	Approved
0.6714	Remote Similarity	NPD2667	Approved
0.6714	Remote Similarity	NPD2668	Approved
0.6714	Remote Similarity	NPD4626	Approved
0.6714	Remote Similarity	NPD1010	Approved
0.6711	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2230	Approved
0.669	Remote Similarity	NPD2233	Approved
0.669	Remote Similarity	NPD2232	Approved
0.6689	Remote Similarity	NPD4060	Phase 1
0.6689	Remote Similarity	NPD1555	Discontinued
0.6667	Remote Similarity	NPD1242	Phase 1
0.6667	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1416	Approved
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1973	Approved
0.6646	Remote Similarity	NPD1972	Approved
0.6646	Remote Similarity	NPD957	Approved
0.6646	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2378	Approved
0.6645	Remote Similarity	NPD2376	Approved
0.6645	Remote Similarity	NPD2377	Approved
0.6644	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4908	Phase 1
0.6643	Remote Similarity	NPD6539	Approved
0.6643	Remote Similarity	NPD6543	Approved
0.6643	Remote Similarity	NPD6540	Phase 3
0.6643	Remote Similarity	NPD6542	Approved
0.6624	Remote Similarity	NPD3364	Phase 3
0.6621	Remote Similarity	NPD4624	Approved
0.662	Remote Similarity	NPD1281	Approved
0.6618	Remote Similarity	NPD5535	Approved
0.6618	Remote Similarity	NPD821	Approved
0.6618	Remote Similarity	NPD7843	Approved
0.6614	Remote Similarity	NPD844	Approved
0.6605	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6056	Approved
0.6604	Remote Similarity	NPD6057	Approved
0.6597	Remote Similarity	NPD6538	Approved
0.6597	Remote Similarity	NPD6541	Approved
0.6594	Remote Similarity	NPD7157	Approved
0.6588	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2354	Approved
0.6577	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1613	Approved
0.6575	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1608	Approved
0.6571	Remote Similarity	NPD1182	Approved
0.657	Remote Similarity	NPD3337	Discontinued
0.6562	Remote Similarity	NPD288	Approved
0.6554	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4359	Approved
0.6525	Remote Similarity	NPD1357	Approved
0.6519	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD9251	Approved
0.6503	Remote Similarity	NPD1535	Discovery
0.65	Remote Similarity	NPD5536	Phase 2
0.6493	Remote Similarity	NPD290	Approved
0.6486	Remote Similarity	NPD7095	Approved
0.6486	Remote Similarity	NPD1024	Discontinued
0.6486	Remote Similarity	NPD4625	Phase 3
0.6481	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD9073	Approved
0.6475	Remote Similarity	NPD111	Approved
0.6475	Remote Similarity	NPD9685	Approved
0.6471	Remote Similarity	NPD2935	Discontinued
0.6471	Remote Similarity	NPD4873	Discontinued
0.6467	Remote Similarity	NPD3620	Phase 2
0.6467	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1558	Phase 1
0.646	Remote Similarity	NPD4972	Discontinued
0.6458	Remote Similarity	NPD2231	Phase 2
0.6458	Remote Similarity	NPD1840	Phase 2
0.6458	Remote Similarity	NPD2235	Phase 2
0.6458	Remote Similarity	NPD1481	Phase 2
0.6454	Remote Similarity	NPD1894	Discontinued
0.6442	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3596	Phase 2
0.6429	Remote Similarity	NPD2353	Approved
0.6425	Remote Similarity	NPD6312	Discontinued
0.6414	Remote Similarity	NPD4749	Approved
0.6414	Remote Similarity	NPD5327	Phase 3
0.641	Remote Similarity	NPD1718	Discontinued
0.6408	Remote Similarity	NPD5691	Approved
0.6403	Remote Similarity	NPD911	Approved
0.64	Remote Similarity	NPD9295	Approved
0.6398	Remote Similarity	NPD5894	Phase 2
0.6398	Remote Similarity	NPD4017	Approved
0.6389	Remote Similarity	NPD422	Phase 1
0.6382	Remote Similarity	NPD4097	Suspended
0.6377	Remote Similarity	NPD769	Approved
0.6369	Remote Similarity	NPD3887	Approved
0.6364	Remote Similarity	NPD940	Approved
0.6364	Remote Similarity	NPD17	Approved
0.6364	Remote Similarity	NPD846	Approved
0.6358	Remote Similarity	NPD2238	Phase 2
0.6358	Remote Similarity	NPD1240	Approved
0.6358	Remote Similarity	NPD4140	Approved
0.6338	Remote Similarity	NPD6580	Approved
0.6338	Remote Similarity	NPD6581	Approved
0.6338	Remote Similarity	NPD3091	Approved
0.6331	Remote Similarity	NPD1241	Discontinued
0.6328	Remote Similarity	NPD5800	Discontinued
0.6319	Remote Similarity	NPD3496	Discontinued
0.6316	Remote Similarity	NPD5735	Approved
0.6304	Remote Similarity	NPD2500	Approved
0.6304	Remote Similarity	NPD2499	Approved
0.6301	Remote Similarity	NPD2982	Phase 2
0.6301	Remote Similarity	NPD2983	Phase 2
0.6296	Remote Similarity	NPD3134	Approved
0.6294	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5585	Approved
0.6294	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2674	Phase 3
0.6291	Remote Similarity	NPD829	Discontinued
0.6284	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7037	Approved
0.6279	Remote Similarity	NPD5096	Phase 3
0.6279	Remote Similarity	NPD5095	Phase 3
0.6277	Remote Similarity	NPD1792	Phase 2
0.6276	Remote Similarity	NPD1611	Approved
0.6275	Remote Similarity	NPD1607	Approved
0.6275	Remote Similarity	NPD6353	Approved
0.6275	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD7635	Approved
0.6259	Remote Similarity	NPD1876	Approved
0.6258	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9532	Phase 3
0.625	Remote Similarity	NPD1778	Approved
0.625	Remote Similarity	NPD1358	Approved
0.625	Remote Similarity	NPD1850	Phase 3
0.625	Remote Similarity	NPD2342	Discontinued
0.625	Remote Similarity	NPD5837	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