NPASS Compound

Structure

NPC139335 OpenBabel07101719402D 21 22 0 0 0 0 0 0 0 0999 V2000 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 8 1 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.2
Volume:	391.118
LogP:	1.992
LogD:	2.016
LogS:	-3.86
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	6.842
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.045
MDCK Permeability:	2.5068697141250595e-05
Pgp-inhibitor:	0.066
Pgp-substrate:	0.75
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.79

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.719
Plasma Protein Binding (PPB):	50.19132995605469%
Volume Distribution (VD):	0.759
Pgp-substrate:	59.20258331298828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.739
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	4.922
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.52
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.673
Carcinogencity:	0.768
Eye Corrosion:	0.015
Eye Irritation:	0.072
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC139335

Natural Product ID:	NPC139335
*Common Name:**	2,4,6,3-Tetrachloro-3-Hydroxy-4-Methoxybibenzyl
IUPAC Name:	2,4,6-trichloro-3-[2-(3-chloro-4-methoxyphenyl)ethyl]phenol
Synonyms:
Standard InCHIKey:	IHJHSSFAWQOOTH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12Cl4O2/c1-21-13-5-3-8(6-11(13)17)2-4-9-10(16)7-12(18)15(20)14(9)19/h3,5-7,20H,2,4H2,1H3
SMILES:	COc1ccc(CCc2c(cc(c(c2Cl)O)Cl)Cl)cc1Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399741
PubChem CID:	24762918
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	=	1.71	ppm	PMID[542559]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	IZ	=	0.0	mm	PMID[542559]

☑ 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 NPC139335 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	582
0.1-0.2	3098
0.2-0.3	12098
0.3-0.4	7609
0.4-0.5	6646
0.5-0.6	10076
0.6-0.7	2490
0.7-0.8	91
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC246991
0.952	High Similarity	NPC8058
0.912	High Similarity	NPC42644
0.856	High Similarity	NPC244403
0.84	Intermediate Similarity	NPC91452
0.8067	Intermediate Similarity	NPC56379
0.8	Intermediate Similarity	NPC146096
0.7857	Intermediate Similarity	NPC75440
0.7793	Intermediate Similarity	NPC131379
0.7786	Intermediate Similarity	NPC193334
0.768	Intermediate Similarity	NPC474603
0.768	Intermediate Similarity	NPC12987
0.7664	Intermediate Similarity	NPC33402
0.7619	Intermediate Similarity	NPC182475
0.7559	Intermediate Similarity	NPC113457
0.7556	Intermediate Similarity	NPC67791
0.7483	Intermediate Similarity	NPC76453
0.7442	Intermediate Similarity	NPC201959
0.7415	Intermediate Similarity	NPC86087
0.7394	Intermediate Similarity	NPC185313
0.7391	Intermediate Similarity	NPC90577
0.7388	Intermediate Similarity	NPC141090
0.7376	Intermediate Similarity	NPC26576
0.7343	Intermediate Similarity	NPC30390
0.7333	Intermediate Similarity	NPC195466
0.7333	Intermediate Similarity	NPC293619
0.7333	Intermediate Similarity	NPC474933
0.7319	Intermediate Similarity	NPC14287
0.7293	Intermediate Similarity	NPC35344
0.7293	Intermediate Similarity	NPC141003
0.7286	Intermediate Similarity	NPC235370
0.7279	Intermediate Similarity	NPC470626
0.7273	Intermediate Similarity	NPC90520
0.7273	Intermediate Similarity	NPC296920
0.7248	Intermediate Similarity	NPC252901
0.7246	Intermediate Similarity	NPC205213
0.7244	Intermediate Similarity	NPC300166
0.7239	Intermediate Similarity	NPC22610
0.7239	Intermediate Similarity	NPC276737
0.723	Intermediate Similarity	NPC475423
0.7226	Intermediate Similarity	NPC310338
0.7226	Intermediate Similarity	NPC281298
0.7218	Intermediate Similarity	NPC280606
0.7197	Intermediate Similarity	NPC43411
0.7185	Intermediate Similarity	NPC167934
0.7185	Intermediate Similarity	NPC808
0.7185	Intermediate Similarity	NPC53906
0.7174	Intermediate Similarity	NPC103916
0.7174	Intermediate Similarity	NPC227217
0.7174	Intermediate Similarity	NPC165133
0.7174	Intermediate Similarity	NPC232316
0.7174	Intermediate Similarity	NPC242885
0.7174	Intermediate Similarity	NPC56214
0.7174	Intermediate Similarity	NPC117780
0.7174	Intermediate Similarity	NPC95614
0.7143	Intermediate Similarity	NPC8547
0.7143	Intermediate Similarity	NPC257124
0.7143	Intermediate Similarity	NPC151237
0.7143	Intermediate Similarity	NPC156840
0.7143	Intermediate Similarity	NPC45072
0.7143	Intermediate Similarity	NPC173746
0.7132	Intermediate Similarity	NPC203113
0.7132	Intermediate Similarity	NPC150624
0.7132	Intermediate Similarity	NPC241224
0.7126	Intermediate Similarity	NPC470422
0.7122	Intermediate Similarity	NPC207613
0.7122	Intermediate Similarity	NPC129176
0.7121	Intermediate Similarity	NPC474272
0.712	Intermediate Similarity	NPC274678
0.7111	Intermediate Similarity	NPC228287
0.7111	Intermediate Similarity	NPC180508
0.7101	Intermediate Similarity	NPC474498
0.7099	Intermediate Similarity	NPC233320
0.7087	Intermediate Similarity	NPC100870
0.708	Intermediate Similarity	NPC221549
0.708	Intermediate Similarity	NPC127894
0.708	Intermediate Similarity	NPC244816
0.708	Intermediate Similarity	NPC470759
0.708	Intermediate Similarity	NPC33270
0.708	Intermediate Similarity	NPC219070
0.708	Intermediate Similarity	NPC50521
0.708	Intermediate Similarity	NPC69261
0.708	Intermediate Similarity	NPC15860
0.7071	Intermediate Similarity	NPC476633
0.7071	Intermediate Similarity	NPC343720
0.7071	Intermediate Similarity	NPC312675
0.7071	Intermediate Similarity	NPC113865
0.7071	Intermediate Similarity	NPC324571
0.7071	Intermediate Similarity	NPC54872
0.7071	Intermediate Similarity	NPC38996
0.7071	Intermediate Similarity	NPC262156
0.7071	Intermediate Similarity	NPC473853
0.7071	Intermediate Similarity	NPC184651
0.7071	Intermediate Similarity	NPC160380
0.7071	Intermediate Similarity	NPC470212
0.7068	Intermediate Similarity	NPC94045
0.7068	Intermediate Similarity	NPC475852
0.7045	Intermediate Similarity	NPC187958
0.7029	Intermediate Similarity	NPC474214
0.7029	Intermediate Similarity	NPC474040
0.7029	Intermediate Similarity	NPC63010
0.7029	Intermediate Similarity	NPC190514
0.7029	Intermediate Similarity	NPC15350
0.7021	Intermediate Similarity	NPC30462
0.7021	Intermediate Similarity	NPC85488
0.7021	Intermediate Similarity	NPC41562
0.7015	Intermediate Similarity	NPC275627
0.7007	Intermediate Similarity	NPC54507
0.7007	Intermediate Similarity	NPC114064
0.7007	Intermediate Similarity	NPC229147
0.7007	Intermediate Similarity	NPC85292
0.7	Intermediate Similarity	NPC102639
0.6992	Remote Similarity	NPC7097
0.6992	Remote Similarity	NPC233731
0.6992	Remote Similarity	NPC36108
0.6992	Remote Similarity	NPC246358
0.6978	Remote Similarity	NPC184302
0.6978	Remote Similarity	NPC474320
0.6972	Remote Similarity	NPC249788
0.6972	Remote Similarity	NPC136319
0.6972	Remote Similarity	NPC197757
0.6972	Remote Similarity	NPC317769
0.6972	Remote Similarity	NPC31344
0.6972	Remote Similarity	NPC84086
0.6972	Remote Similarity	NPC228922
0.6972	Remote Similarity	NPC233526
0.6972	Remote Similarity	NPC282496
0.6972	Remote Similarity	NPC471693
0.6972	Remote Similarity	NPC280704
0.6957	Remote Similarity	NPC86947
0.6957	Remote Similarity	NPC164386
0.695	Remote Similarity	NPC290451
0.695	Remote Similarity	NPC127389
0.6947	Remote Similarity	NPC233396
0.6947	Remote Similarity	NPC154899
0.694	Remote Similarity	NPC137685
0.694	Remote Similarity	NPC168657
0.6934	Remote Similarity	NPC296526
0.6934	Remote Similarity	NPC464
0.6934	Remote Similarity	NPC185541
0.6923	Remote Similarity	NPC138248
0.6923	Remote Similarity	NPC228503
0.6923	Remote Similarity	NPC206487
0.6923	Remote Similarity	NPC5796
0.6923	Remote Similarity	NPC305205
0.6912	Remote Similarity	NPC165106
0.6906	Remote Similarity	NPC131118
0.6905	Remote Similarity	NPC277865
0.6905	Remote Similarity	NPC470565
0.6901	Remote Similarity	NPC27198
0.6894	Remote Similarity	NPC92623
0.6894	Remote Similarity	NPC135464
0.6892	Remote Similarity	NPC66643
0.6889	Remote Similarity	NPC78918
0.6889	Remote Similarity	NPC139617
0.6889	Remote Similarity	NPC195873
0.6884	Remote Similarity	NPC19290
0.6884	Remote Similarity	NPC221049
0.688	Remote Similarity	NPC321956
0.688	Remote Similarity	NPC45040
0.688	Remote Similarity	NPC322888
0.6879	Remote Similarity	NPC131868
0.6879	Remote Similarity	NPC100108
0.6879	Remote Similarity	NPC277798
0.6875	Remote Similarity	NPC228771
0.6875	Remote Similarity	NPC257589
0.6875	Remote Similarity	NPC278955
0.6875	Remote Similarity	NPC105031
0.6875	Remote Similarity	NPC472093
0.6875	Remote Similarity	NPC116907
0.6875	Remote Similarity	NPC53305
0.6875	Remote Similarity	NPC29008
0.6875	Remote Similarity	NPC233410
0.6875	Remote Similarity	NPC148627
0.6875	Remote Similarity	NPC251855
0.6875	Remote Similarity	NPC17943
0.6875	Remote Similarity	NPC105718
0.6875	Remote Similarity	NPC221077
0.6875	Remote Similarity	NPC117214
0.6875	Remote Similarity	NPC475169
0.6875	Remote Similarity	NPC193544
0.6875	Remote Similarity	NPC9067
0.6875	Remote Similarity	NPC298757
0.6875	Remote Similarity	NPC203133
0.6875	Remote Similarity	NPC470161
0.6875	Remote Similarity	NPC208950
0.6875	Remote Similarity	NPC105925
0.6875	Remote Similarity	NPC266705
0.6875	Remote Similarity	NPC113495
0.6875	Remote Similarity	NPC57490
0.687	Remote Similarity	NPC292792
0.687	Remote Similarity	NPC38079
0.687	Remote Similarity	NPC108875
0.6864	Remote Similarity	NPC474857
0.6861	Remote Similarity	NPC470837
0.6857	Remote Similarity	NPC24474
0.6857	Remote Similarity	NPC311595
0.6857	Remote Similarity	NPC226629
0.685	Remote Similarity	NPC26244
0.6842	Remote Similarity	NPC251306

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 NPC139335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	502
0.1-0.2	1106
0.2-0.3	1939
0.3-0.4	2685
0.4-0.5	1758
0.5-0.6	956
0.6-0.7	186
0.7-0.8	18
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
0.7852	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4589	Approved
0.7552	Intermediate Similarity	NPD1184	Approved
0.7518	Intermediate Similarity	NPD1157	Approved
0.75	Intermediate Similarity	NPD454	Approved
0.75	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4538	Approved
0.7448	Intermediate Similarity	NPD4536	Approved
0.7448	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5451	Approved
0.7323	Intermediate Similarity	NPD9500	Approved
0.7279	Intermediate Similarity	NPD5960	Phase 3
0.7279	Intermediate Similarity	NPD5588	Approved
0.725	Intermediate Similarity	NPD3365	Discontinued
0.7246	Intermediate Similarity	NPD915	Approved
0.7237	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7041	Phase 2
0.7229	Intermediate Similarity	NPD3303	Discontinued
0.7152	Intermediate Similarity	NPD4535	Phase 3
0.7143	Intermediate Similarity	NPD228	Approved
0.7059	Intermediate Similarity	NPD5058	Phase 3
0.702	Intermediate Similarity	NPD4534	Discontinued
0.6972	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1578	Phase 2
0.6948	Remote Similarity	NPD6815	Approved
0.6929	Remote Similarity	NPD5846	Approved
0.6929	Remote Similarity	NPD6516	Phase 2
0.6912	Remote Similarity	NPD5283	Phase 1
0.6908	Remote Similarity	NPD5958	Discontinued
0.6908	Remote Similarity	NPD2808	Discontinued
0.6894	Remote Similarity	NPD968	Approved
0.6887	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2859	Approved
0.685	Remote Similarity	NPD2860	Approved
0.6828	Remote Similarity	NPD6584	Phase 3
0.6822	Remote Similarity	NPD3020	Approved
0.6812	Remote Similarity	NPD6671	Approved
0.6772	Remote Similarity	NPD2933	Approved
0.6772	Remote Similarity	NPD2934	Approved
0.6769	Remote Similarity	NPD1616	Discontinued
0.6753	Remote Similarity	NPD1416	Approved
0.6713	Remote Similarity	NPD1610	Phase 2
0.6709	Remote Similarity	NPD3364	Phase 3
0.669	Remote Similarity	NPD1283	Approved
0.6689	Remote Similarity	NPD3027	Phase 3
0.6689	Remote Similarity	NPD2989	Phase 2
0.6689	Remote Similarity	NPD2986	Phase 2
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD2354	Approved
0.6647	Remote Similarity	NPD3337	Discontinued
0.6646	Remote Similarity	NPD1714	Approved
0.6646	Remote Similarity	NPD1715	Phase 1
0.6644	Remote Similarity	NPD987	Approved
0.6621	Remote Similarity	NPD6582	Phase 2
0.6621	Remote Similarity	NPD6583	Phase 3
0.6621	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1669	Approved
0.662	Remote Similarity	NPD1651	Approved
0.6618	Remote Similarity	NPD3022	Approved
0.6618	Remote Similarity	NPD3021	Approved
0.6617	Remote Similarity	NPD9501	Approved
0.6614	Remote Similarity	NPD9251	Approved
0.6605	Remote Similarity	NPD958	Approved
0.6604	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD9552	Approved
0.6581	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1010	Approved
0.6573	Remote Similarity	NPD2667	Approved
0.6573	Remote Similarity	NPD2668	Approved
0.6573	Remote Similarity	NPD4626	Approved
0.6571	Remote Similarity	NPD709	Approved
0.6556	Remote Similarity	NPD4060	Phase 1
0.6556	Remote Similarity	NPD1555	Discontinued
0.6552	Remote Similarity	NPD2230	Approved
0.6552	Remote Similarity	NPD2233	Approved
0.6552	Remote Similarity	NPD2232	Approved
0.6536	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3847	Discontinued
0.6522	Remote Similarity	NPD1973	Approved
0.6522	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD957	Approved
0.6522	Remote Similarity	NPD1972	Approved
0.6516	Remote Similarity	NPD2377	Approved
0.6516	Remote Similarity	NPD2376	Approved
0.6516	Remote Similarity	NPD2353	Approved
0.6516	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD2378	Approved
0.6515	Remote Similarity	NPD1242	Phase 1
0.6512	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4908	Phase 1
0.6507	Remote Similarity	NPD6540	Phase 3
0.6507	Remote Similarity	NPD6543	Approved
0.6507	Remote Similarity	NPD6542	Approved
0.6507	Remote Similarity	NPD6539	Approved
0.6497	Remote Similarity	NPD1718	Discontinued
0.6486	Remote Similarity	NPD4624	Approved
0.6485	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1281	Approved
0.6481	Remote Similarity	NPD6057	Approved
0.6481	Remote Similarity	NPD6056	Approved
0.6481	Remote Similarity	NPD4017	Approved
0.6475	Remote Similarity	NPD7843	Approved
0.6475	Remote Similarity	NPD5535	Approved
0.6475	Remote Similarity	NPD821	Approved
0.6474	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6538	Approved
0.6463	Remote Similarity	NPD6541	Approved
0.6462	Remote Similarity	NPD844	Approved
0.6456	Remote Similarity	NPD3887	Approved
0.6454	Remote Similarity	NPD7157	Approved
0.6447	Remote Similarity	NPD1613	Approved
0.6447	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1608	Approved
0.6437	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1182	Approved
0.6424	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD288	Approved
0.6395	Remote Similarity	NPD4359	Approved
0.6391	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1357	Approved
0.6383	Remote Similarity	NPD911	Approved
0.637	Remote Similarity	NPD1535	Discovery
0.6364	Remote Similarity	NPD5536	Phase 2
0.6364	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4625	Phase 3
0.6358	Remote Similarity	NPD7095	Approved
0.6358	Remote Similarity	NPD1024	Discontinued
0.6358	Remote Similarity	NPD4873	Discontinued
0.635	Remote Similarity	NPD290	Approved
0.6346	Remote Similarity	NPD2935	Discontinued
0.6341	Remote Similarity	NPD4972	Discontinued
0.634	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.634	Remote Similarity	NPD1558	Phase 1
0.634	Remote Similarity	NPD3620	Phase 2
0.6338	Remote Similarity	NPD9685	Approved
0.6327	Remote Similarity	NPD2231	Phase 2
0.6327	Remote Similarity	NPD1481	Phase 2
0.6327	Remote Similarity	NPD1840	Phase 2
0.6327	Remote Similarity	NPD2235	Phase 2
0.6325	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.632	Remote Similarity	NPD9073	Approved
0.632	Remote Similarity	NPD111	Approved
0.6319	Remote Similarity	NPD6312	Discontinued
0.6319	Remote Similarity	NPD1894	Discontinued
0.6303	Remote Similarity	NPD3274	Phase 2
0.6294	Remote Similarity	NPD3596	Phase 2
0.6294	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4749	Approved
0.6284	Remote Similarity	NPD5327	Phase 3
0.628	Remote Similarity	NPD5894	Phase 2
0.6276	Remote Similarity	NPD5691	Approved
0.6259	Remote Similarity	NPD422	Phase 1
0.6258	Remote Similarity	NPD4097	Suspended
0.625	Remote Similarity	NPD2372	Approved
0.625	Remote Similarity	NPD9295	Approved
0.6241	Remote Similarity	NPD769	Approved
0.6234	Remote Similarity	NPD4140	Approved
0.6234	Remote Similarity	NPD2238	Phase 2
0.6234	Remote Similarity	NPD1240	Approved
0.6233	Remote Similarity	NPD17	Approved
0.6222	Remote Similarity	NPD846	Approved
0.6222	Remote Similarity	NPD5800	Discontinued
0.6222	Remote Similarity	NPD940	Approved
0.6207	Remote Similarity	NPD3091	Approved
0.6207	Remote Similarity	NPD6580	Approved
0.6207	Remote Similarity	NPD6581	Approved
0.6197	Remote Similarity	NPD1241	Discontinued
0.6197	Remote Similarity	NPD2991	Approved
0.6197	Remote Similarity	NPD2988	Approved
0.6196	Remote Similarity	NPD1159	Approved
0.6194	Remote Similarity	NPD5735	Approved
0.619	Remote Similarity	NPD3496	Discontinued
0.6185	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD2982	Phase 2
0.6174	Remote Similarity	NPD2983	Phase 2
0.6171	Remote Similarity	NPD5096	Phase 3
0.6171	Remote Similarity	NPD5095	Phase 3
0.617	Remote Similarity	NPD2500	Approved
0.617	Remote Similarity	NPD2499	Approved
0.6169	Remote Similarity	NPD2674	Phase 3
0.6169	Remote Similarity	NPD829	Discontinued
0.6164	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD7037	Approved
0.6164	Remote Similarity	NPD5585	Approved
0.6159	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3134	Approved
0.6154	Remote Similarity	NPD1607	Approved
0.6154	Remote Similarity	NPD6353	Approved
0.6154	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1611	Approved
0.6145	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD1792	Phase 2
0.614	Remote Similarity	NPD1850	Phase 3
0.6133	Remote Similarity	NPD1876	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