NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	296.04
Volume:	283.067
LogP:	4.979
LogD:	3.888
LogS:	-5.796
# Rotatable Bonds:	4
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.9
Synthetic Accessibility Score:	1.932
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:	-4.778
MDCK Permeability:	1.3905651030654553e-05
Pgp-inhibitor:	0.833
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.821

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.339
Plasma Protein Binding (PPB):	99.42890167236328%
Volume Distribution (VD):	1.768
Pgp-substrate:	1.077531337738037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.174
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.7

ADMET: Excretion

Clearance (CL):	9.021
Half-life (T1/2):	0.189

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.68
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.663
Skin Sensitization:	0.804
Carcinogencity:	0.231
Eye Corrosion:	0.048
Eye Irritation:	0.948
Respiratory Toxicity:	0.659

Download Data

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

Natural Product: NPC8058

Natural Product ID:	NPC8058
*Common Name:**	2,6-Dichloro-3-Hydroxy-4-Methoxybibenzyl
IUPAC Name:	2,4-dichloro-3-[2-(4-methoxyphenyl)ethyl]phenol
Synonyms:
Standard InCHIKey:	QSWIRQVPUSIUGY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14Cl2O2/c1-19-11-5-2-10(3-6-11)4-7-12-13(16)8-9-14(18)15(12)17/h2-3,5-6,8-9,18H,4,7H2,1H3
SMILES:	COc1ccc(cc1)CCc1c(ccc(c1Cl)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL442277
PubChem CID:	24762917
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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.44	ppm	PMID[503714]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	IZ	=	22.0	mm	PMID[503714]

☑ 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 NPC8058 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	514
0.1-0.2	2697
0.2-0.3	10578
0.3-0.4	9123
0.4-0.5	5514
0.5-0.6	10422
0.6-0.7	3553
0.7-0.8	286
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9754	High Similarity	NPC246991
0.952	High Similarity	NPC139335
0.879	High Similarity	NPC42644
0.8678	High Similarity	NPC244403
0.8512	High Similarity	NPC91452
0.8403	Intermediate Similarity	NPC146096
0.825	Intermediate Similarity	NPC75440
0.8067	Intermediate Similarity	NPC12987
0.8067	Intermediate Similarity	NPC474603
0.7934	Intermediate Similarity	NPC113457
0.7868	Intermediate Similarity	NPC193334
0.7805	Intermediate Similarity	NPC201959
0.7744	Intermediate Similarity	NPC33402
0.7734	Intermediate Similarity	NPC141090
0.7674	Intermediate Similarity	NPC195466
0.7674	Intermediate Similarity	NPC474933
0.7674	Intermediate Similarity	NPC293619
0.7667	Intermediate Similarity	NPC56379
0.7638	Intermediate Similarity	NPC35344
0.7638	Intermediate Similarity	NPC141003
0.7634	Intermediate Similarity	NPC67791
0.7619	Intermediate Similarity	NPC90520
0.7619	Intermediate Similarity	NPC296920
0.7615	Intermediate Similarity	NPC470626
0.7603	Intermediate Similarity	NPC300166
0.7578	Intermediate Similarity	NPC276737
0.7578	Intermediate Similarity	NPC22610
0.7569	Intermediate Similarity	NPC182475
0.7559	Intermediate Similarity	NPC280606
0.7557	Intermediate Similarity	NPC310338
0.7557	Intermediate Similarity	NPC281298
0.7554	Intermediate Similarity	NPC76453
0.7552	Intermediate Similarity	NPC252901
0.754	Intermediate Similarity	NPC43411
0.7519	Intermediate Similarity	NPC808
0.7519	Intermediate Similarity	NPC53906
0.7519	Intermediate Similarity	NPC167934
0.75	Intermediate Similarity	NPC242885
0.75	Intermediate Similarity	NPC227217
0.75	Intermediate Similarity	NPC131379
0.75	Intermediate Similarity	NPC117780
0.75	Intermediate Similarity	NPC232316
0.75	Intermediate Similarity	NPC95614
0.75	Intermediate Similarity	NPC56214
0.75	Intermediate Similarity	NPC103916
0.75	Intermediate Similarity	NPC165133
0.748	Intermediate Similarity	NPC8547
0.748	Intermediate Similarity	NPC241224
0.748	Intermediate Similarity	NPC173746
0.748	Intermediate Similarity	NPC156840
0.748	Intermediate Similarity	NPC257124
0.7479	Intermediate Similarity	NPC274678
0.7462	Intermediate Similarity	NPC203113
0.7462	Intermediate Similarity	NPC150624
0.746	Intermediate Similarity	NPC474272
0.7445	Intermediate Similarity	NPC26576
0.7444	Intermediate Similarity	NPC205213
0.7444	Intermediate Similarity	NPC207613
0.7444	Intermediate Similarity	NPC129176
0.7442	Intermediate Similarity	NPC228287
0.7442	Intermediate Similarity	NPC180508
0.744	Intermediate Similarity	NPC233320
0.7438	Intermediate Similarity	NPC100870
0.741	Intermediate Similarity	NPC30390
0.7405	Intermediate Similarity	NPC244816
0.7405	Intermediate Similarity	NPC470759
0.7405	Intermediate Similarity	NPC33270
0.7405	Intermediate Similarity	NPC50521
0.7405	Intermediate Similarity	NPC69261
0.7405	Intermediate Similarity	NPC15860
0.7405	Intermediate Similarity	NPC127894
0.7405	Intermediate Similarity	NPC219070
0.7405	Intermediate Similarity	NPC221549
0.7402	Intermediate Similarity	NPC475852
0.7402	Intermediate Similarity	NPC94045
0.7388	Intermediate Similarity	NPC38996
0.7388	Intermediate Similarity	NPC476633
0.7388	Intermediate Similarity	NPC54872
0.7388	Intermediate Similarity	NPC262156
0.7388	Intermediate Similarity	NPC184651
0.7388	Intermediate Similarity	NPC113865
0.7388	Intermediate Similarity	NPC343720
0.7388	Intermediate Similarity	NPC312675
0.7388	Intermediate Similarity	NPC14287
0.7388	Intermediate Similarity	NPC470212
0.7388	Intermediate Similarity	NPC160380
0.7388	Intermediate Similarity	NPC473853
0.7388	Intermediate Similarity	NPC324571
0.7361	Intermediate Similarity	NPC86087
0.7353	Intermediate Similarity	NPC235370
0.7348	Intermediate Similarity	NPC474040
0.7348	Intermediate Similarity	NPC63010
0.7348	Intermediate Similarity	NPC474214
0.7348	Intermediate Similarity	NPC190514
0.7344	Intermediate Similarity	NPC275627
0.7333	Intermediate Similarity	NPC41562
0.7333	Intermediate Similarity	NPC90577
0.7333	Intermediate Similarity	NPC30462
0.7333	Intermediate Similarity	NPC85488
0.7328	Intermediate Similarity	NPC85292
0.7328	Intermediate Similarity	NPC54507
0.7328	Intermediate Similarity	NPC229147
0.7328	Intermediate Similarity	NPC114064
0.7323	Intermediate Similarity	NPC246358
0.7323	Intermediate Similarity	NPC233731
0.7323	Intermediate Similarity	NPC7097
0.7323	Intermediate Similarity	NPC36108
0.7313	Intermediate Similarity	NPC102639
0.7293	Intermediate Similarity	NPC184302
0.7293	Intermediate Similarity	NPC474320
0.728	Intermediate Similarity	NPC233396
0.728	Intermediate Similarity	NPC154899
0.7279	Intermediate Similarity	NPC197757
0.7279	Intermediate Similarity	NPC228922
0.7279	Intermediate Similarity	NPC31344
0.7279	Intermediate Similarity	NPC233526
0.7279	Intermediate Similarity	NPC282496
0.7279	Intermediate Similarity	NPC317769
0.7279	Intermediate Similarity	NPC84086
0.7279	Intermediate Similarity	NPC249788
0.7279	Intermediate Similarity	NPC280704
0.7279	Intermediate Similarity	NPC136319
0.7279	Intermediate Similarity	NPC471693
0.7273	Intermediate Similarity	NPC86947
0.7273	Intermediate Similarity	NPC164386
0.7266	Intermediate Similarity	NPC168657
0.7266	Intermediate Similarity	NPC137685
0.7259	Intermediate Similarity	NPC127389
0.7259	Intermediate Similarity	NPC290451
0.7258	Intermediate Similarity	NPC305205
0.7252	Intermediate Similarity	NPC296526
0.7252	Intermediate Similarity	NPC464
0.7252	Intermediate Similarity	NPC185541
0.7231	Intermediate Similarity	NPC165106
0.7227	Intermediate Similarity	NPC45040
0.7227	Intermediate Similarity	NPC322888
0.7227	Intermediate Similarity	NPC321956
0.7226	Intermediate Similarity	NPC228503
0.7226	Intermediate Similarity	NPC138248
0.7226	Intermediate Similarity	NPC5796
0.7226	Intermediate Similarity	NPC206487
0.7222	Intermediate Similarity	NPC92623
0.7222	Intermediate Similarity	NPC135464
0.7218	Intermediate Similarity	NPC131118
0.7214	Intermediate Similarity	NPC185313
0.7213	Intermediate Similarity	NPC470161
0.7209	Intermediate Similarity	NPC195873
0.7209	Intermediate Similarity	NPC139617
0.7209	Intermediate Similarity	NPC78918
0.7206	Intermediate Similarity	NPC151237
0.72	Intermediate Similarity	NPC38079
0.72	Intermediate Similarity	NPC292792
0.72	Intermediate Similarity	NPC108875
0.7197	Intermediate Similarity	NPC19290
0.7197	Intermediate Similarity	NPC221049
0.719	Intermediate Similarity	NPC26244
0.7185	Intermediate Similarity	NPC131868
0.7185	Intermediate Similarity	NPC277798
0.7185	Intermediate Similarity	NPC100108
0.7178	Intermediate Similarity	NPC470422
0.7176	Intermediate Similarity	NPC470837
0.7174	Intermediate Similarity	NPC298757
0.7174	Intermediate Similarity	NPC29008
0.7174	Intermediate Similarity	NPC266705
0.7174	Intermediate Similarity	NPC105925
0.7174	Intermediate Similarity	NPC233410
0.7174	Intermediate Similarity	NPC148627
0.7174	Intermediate Similarity	NPC117214
0.7174	Intermediate Similarity	NPC193544
0.7174	Intermediate Similarity	NPC57490
0.7174	Intermediate Similarity	NPC105031
0.7174	Intermediate Similarity	NPC278955
0.7174	Intermediate Similarity	NPC105718
0.7174	Intermediate Similarity	NPC116907
0.7174	Intermediate Similarity	NPC53305
0.7174	Intermediate Similarity	NPC251855
0.7174	Intermediate Similarity	NPC257589
0.7174	Intermediate Similarity	NPC228771
0.7174	Intermediate Similarity	NPC9067
0.7174	Intermediate Similarity	NPC472093
0.7174	Intermediate Similarity	NPC203133
0.7174	Intermediate Similarity	NPC17943
0.7174	Intermediate Similarity	NPC208950
0.7174	Intermediate Similarity	NPC221077
0.7174	Intermediate Similarity	NPC113495
0.7174	Intermediate Similarity	NPC475169
0.7172	Intermediate Similarity	NPC475423
0.7165	Intermediate Similarity	NPC227894
0.7165	Intermediate Similarity	NPC251306
0.7164	Intermediate Similarity	NPC226629
0.7164	Intermediate Similarity	NPC24474
0.7164	Intermediate Similarity	NPC311595
0.7154	Intermediate Similarity	NPC92730
0.7154	Intermediate Similarity	NPC98372
0.7143	Intermediate Similarity	NPC470393
0.7143	Intermediate Similarity	NPC71853
0.7132	Intermediate Similarity	NPC2682
0.7132	Intermediate Similarity	NPC303521
0.7132	Intermediate Similarity	NPC251259
0.7131	Intermediate Similarity	NPC473388

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 NPC8058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1116
0.2-0.3	1737
0.3-0.4	2690
0.4-0.5	1768
0.5-0.6	1078
0.6-0.7	276
0.7-0.8	35
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7808	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD4589	Approved
0.7754	Intermediate Similarity	NPD1184	Approved
0.7742	Intermediate Similarity	NPD5451	Approved
0.7686	Intermediate Similarity	NPD9500	Approved
0.7518	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4538	Approved
0.7518	Intermediate Similarity	NPD4536	Approved
0.748	Intermediate Similarity	NPD228	Approved
0.7463	Intermediate Similarity	NPD1157	Approved
0.7445	Intermediate Similarity	NPD454	Approved
0.7444	Intermediate Similarity	NPD915	Approved
0.7442	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5960	Phase 3
0.7343	Intermediate Similarity	NPD5588	Approved
0.7297	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7041	Phase 2
0.7279	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6516	Phase 2
0.7239	Intermediate Similarity	NPD5846	Approved
0.7231	Intermediate Similarity	NPD5283	Phase 1
0.7222	Intermediate Similarity	NPD968	Approved
0.7211	Intermediate Similarity	NPD4535	Phase 3
0.719	Intermediate Similarity	NPD2859	Approved
0.719	Intermediate Similarity	NPD2860	Approved
0.7154	Intermediate Similarity	NPD3020	Approved
0.7122	Intermediate Similarity	NPD6584	Phase 3
0.7121	Intermediate Similarity	NPD6671	Approved
0.7114	Intermediate Similarity	NPD5058	Phase 3
0.7107	Intermediate Similarity	NPD2934	Approved
0.7107	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD1616	Discontinued
0.7089	Intermediate Similarity	NPD3365	Discontinued
0.7075	Intermediate Similarity	NPD4534	Discontinued
0.7073	Intermediate Similarity	NPD3303	Discontinued
0.702	Intermediate Similarity	NPD1578	Phase 2
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD6815	Approved
0.6978	Remote Similarity	NPD1283	Approved
0.6977	Remote Similarity	NPD2684	Approved
0.6972	Remote Similarity	NPD3027	Phase 3
0.6966	Remote Similarity	NPD2986	Phase 2
0.6966	Remote Similarity	NPD2989	Phase 2
0.6963	Remote Similarity	NPD1548	Phase 1
0.6959	Remote Similarity	NPD5958	Discontinued
0.6959	Remote Similarity	NPD2808	Discontinued
0.695	Remote Similarity	NPD2861	Phase 2
0.6939	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD987	Approved
0.6929	Remote Similarity	NPD9501	Approved
0.6923	Remote Similarity	NPD3021	Approved
0.6923	Remote Similarity	NPD3022	Approved
0.6912	Remote Similarity	NPD1651	Approved
0.6906	Remote Similarity	NPD6582	Phase 2
0.6906	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6583	Phase 3
0.6906	Remote Similarity	NPD1669	Approved
0.6899	Remote Similarity	NPD9552	Approved
0.6866	Remote Similarity	NPD709	Approved
0.6861	Remote Similarity	NPD2668	Approved
0.6861	Remote Similarity	NPD2667	Approved
0.6861	Remote Similarity	NPD4626	Approved
0.6835	Remote Similarity	NPD2232	Approved
0.6835	Remote Similarity	NPD2233	Approved
0.6835	Remote Similarity	NPD2230	Approved
0.6829	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4060	Phase 1
0.6825	Remote Similarity	NPD1242	Phase 1
0.6812	Remote Similarity	NPD3847	Discontinued
0.6803	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6543	Approved
0.6786	Remote Similarity	NPD6539	Approved
0.6786	Remote Similarity	NPD6540	Phase 3
0.6786	Remote Similarity	NPD6542	Approved
0.6783	Remote Similarity	NPD4908	Phase 1
0.6783	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD844	Approved
0.6767	Remote Similarity	NPD821	Approved
0.6767	Remote Similarity	NPD7843	Approved
0.6767	Remote Similarity	NPD5535	Approved
0.6763	Remote Similarity	NPD1281	Approved
0.6761	Remote Similarity	NPD4624	Approved
0.6741	Remote Similarity	NPD7157	Approved
0.6739	Remote Similarity	NPD1010	Approved
0.6738	Remote Similarity	NPD6541	Approved
0.6738	Remote Similarity	NPD6538	Approved
0.6731	Remote Similarity	NPD6057	Approved
0.6731	Remote Similarity	NPD6056	Approved
0.672	Remote Similarity	NPD288	Approved
0.6715	Remote Similarity	NPD1182	Approved
0.6714	Remote Similarity	NPD1608	Approved
0.6713	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1613	Approved
0.6711	Remote Similarity	NPD2354	Approved
0.6693	Remote Similarity	NPD289	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1416	Approved
0.6667	Remote Similarity	NPD1357	Approved
0.6667	Remote Similarity	NPD4359	Approved
0.6667	Remote Similarity	NPD9251	Approved
0.6643	Remote Similarity	NPD1535	Discovery
0.6642	Remote Similarity	NPD5536	Phase 2
0.6641	Remote Similarity	NPD290	Approved
0.6639	Remote Similarity	NPD111	Approved
0.6639	Remote Similarity	NPD9073	Approved
0.6623	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7095	Approved
0.6621	Remote Similarity	NPD1024	Discontinued
0.6621	Remote Similarity	NPD4625	Phase 3
0.66	Remote Similarity	NPD2935	Discontinued
0.6599	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1558	Phase 1
0.6599	Remote Similarity	NPD1555	Discontinued
0.6599	Remote Similarity	NPD3620	Phase 2
0.6596	Remote Similarity	NPD1840	Phase 2
0.6596	Remote Similarity	NPD2231	Phase 2
0.6596	Remote Similarity	NPD1481	Phase 2
0.6596	Remote Similarity	NPD2235	Phase 2
0.6594	Remote Similarity	NPD1894	Discontinued
0.6582	Remote Similarity	NPD1714	Approved
0.6582	Remote Similarity	NPD1715	Phase 1
0.6569	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3596	Phase 2
0.6561	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1972	Approved
0.6561	Remote Similarity	NPD1973	Approved
0.6557	Remote Similarity	NPD9295	Approved
0.6556	Remote Similarity	NPD2377	Approved
0.6556	Remote Similarity	NPD2376	Approved
0.6556	Remote Similarity	NPD2353	Approved
0.6556	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2378	Approved
0.6549	Remote Similarity	NPD5327	Phase 3
0.6549	Remote Similarity	NPD4749	Approved
0.6547	Remote Similarity	NPD5691	Approved
0.6544	Remote Similarity	NPD911	Approved
0.6541	Remote Similarity	NPD958	Approved
0.6538	Remote Similarity	NPD3364	Phase 3
0.6536	Remote Similarity	NPD1718	Discontinued
0.6525	Remote Similarity	NPD422	Phase 1
0.6522	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5894	Phase 2
0.6519	Remote Similarity	NPD769	Approved
0.6519	Remote Similarity	NPD4017	Approved
0.6512	Remote Similarity	NPD940	Approved
0.6512	Remote Similarity	NPD846	Approved
0.651	Remote Similarity	NPD4097	Suspended
0.65	Remote Similarity	NPD17	Approved
0.6496	Remote Similarity	NPD9685	Approved
0.6494	Remote Similarity	NPD3887	Approved
0.6491	Remote Similarity	NPD3337	Discontinued
0.6486	Remote Similarity	NPD2238	Phase 2
0.6486	Remote Similarity	NPD1240	Approved
0.6486	Remote Similarity	NPD4140	Approved
0.6475	Remote Similarity	NPD3091	Approved
0.6475	Remote Similarity	NPD6581	Approved
0.6475	Remote Similarity	NPD6580	Approved
0.6471	Remote Similarity	NPD1241	Discontinued
0.6456	Remote Similarity	NPD957	Approved
0.6454	Remote Similarity	NPD3496	Discontinued
0.6444	Remote Similarity	NPD2500	Approved
0.6444	Remote Similarity	NPD2499	Approved
0.6443	Remote Similarity	NPD5735	Approved
0.6439	Remote Similarity	NPD3134	Approved
0.6434	Remote Similarity	NPD2982	Phase 2
0.6434	Remote Similarity	NPD2983	Phase 2
0.6433	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5585	Approved
0.6429	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD829	Discontinued
0.6419	Remote Similarity	NPD2674	Phase 3
0.6418	Remote Similarity	NPD1792	Phase 2
0.6414	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1611	Approved
0.6407	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7037	Approved
0.64	Remote Similarity	NPD6353	Approved
0.64	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1607	Approved
0.6398	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD7635	Approved
0.6395	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD4873	Discontinued
0.6391	Remote Similarity	NPD2342	Discontinued
0.6391	Remote Similarity	NPD1358	Approved
0.6391	Remote Similarity	NPD9532	Phase 3
0.6389	Remote Similarity	NPD1876	Approved
0.6383	Remote Similarity	NPD1778	Approved
0.6378	Remote Similarity	NPD1809	Phase 2
0.6377	Remote Similarity	NPD191	Approved
0.6377	Remote Similarity	NPD2557	Approved
0.6376	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4972	Discontinued
0.6374	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.637	Remote Similarity	NPD9494	Approved
0.637	Remote Similarity	NPD3018	Phase 2
0.6364	Remote Similarity	NPD3972	Approved
0.6364	Remote Similarity	NPD3060	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data