NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	310.03
Volume:	261.967
LogP:	1.167
LogD:	1.944
LogS:	-2.531
# Rotatable Bonds:	4
TPSA:	56.33
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.912
Synthetic Accessibility Score:	2.752
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.26
MDCK Permeability:	1.1373418601579033e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	69.8642807006836%
Volume Distribution (VD):	1.301
Pgp-substrate:	54.57899475097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.418
CYP1A2-substrate:	0.837
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.335
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.291
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	3.824
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.486
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.836
Maximum Recommended Daily Dose:	0.398
Skin Sensitization:	0.194
Carcinogencity:	0.358
Eye Corrosion:	0.005
Eye Irritation:	0.071
Respiratory Toxicity:	0.419

Download Data

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

Natural Product: NPC179701

Natural Product ID:	NPC179701
*Common Name:**	(-)-5-Bromo-N,N-Dimethyltryptophan
IUPAC Name:	(2S)-3-(5-bromo-1H-indol-3-yl)-2-(dimethylamino)propanoic acid
Synonyms:
Standard InCHIKey:	UBAMMGHQGXPKOD-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C13H15BrN2O2/c1-16(2)12(13(17)18)5-8-7-15-11-4-3-9(14)6-10(8)11/h3-4,6-7,12,15H,5H2,1-2H3,(H,17,18)/t12-/m0/s1
SMILES:	CN(C)[C@@H](Cc1c[nH]c2ccc(cc12)Br)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465717
PubChem CID:	11616565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002404] Alpha amino acids [CHEMONTID:0004146] L-alpha-amino acids

*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
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374971]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975486]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	25.0	ug.mL-1	PMID[516637]

☑ 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 NPC179701 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	334
0.1-0.2	3202
0.2-0.3	19163
0.3-0.4	13129
0.4-0.5	2740
0.5-0.6	2272
0.6-0.7	1321
0.7-0.8	488
0.8-0.85	21
0.85-0.9	17
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9943	High Similarity	NPC262898
0.9191	High Similarity	NPC126709
0.9191	High Similarity	NPC248041
0.908	High Similarity	NPC283219
0.9075	High Similarity	NPC267885
0.9023	High Similarity	NPC145885
0.9023	High Similarity	NPC84827
0.9023	High Similarity	NPC14113
0.9017	High Similarity	NPC149155
0.9017	High Similarity	NPC203468
0.9017	High Similarity	NPC110500
0.8786	High Similarity	NPC78020
0.8674	High Similarity	NPC235684
0.8513	High Similarity	NPC207020
0.8495	Intermediate Similarity	NPC88315
0.8478	Intermediate Similarity	NPC321708
0.8444	Intermediate Similarity	NPC219336
0.8444	Intermediate Similarity	NPC55772
0.8389	Intermediate Similarity	NPC183662
0.8389	Intermediate Similarity	NPC111275
0.8389	Intermediate Similarity	NPC217372
0.8389	Intermediate Similarity	NPC15573
0.8266	Intermediate Similarity	NPC34844
0.8242	Intermediate Similarity	NPC213468
0.8239	Intermediate Similarity	NPC282231
0.8202	Intermediate Similarity	NPC109447
0.8182	Intermediate Similarity	NPC279918
0.8172	Intermediate Similarity	NPC315555
0.8162	Intermediate Similarity	NPC228835
0.8154	Intermediate Similarity	NPC473376
0.8142	Intermediate Similarity	NPC11126
0.8128	Intermediate Similarity	NPC17059
0.8119	Intermediate Similarity	NPC475736
0.8101	Intermediate Similarity	NPC160105
0.8101	Intermediate Similarity	NPC474561
0.8101	Intermediate Similarity	NPC49954
0.8098	Intermediate Similarity	NPC469896
0.8085	Intermediate Similarity	NPC213629
0.8075	Intermediate Similarity	NPC94752
0.8075	Intermediate Similarity	NPC62749
0.8053	Intermediate Similarity	NPC477167
0.8053	Intermediate Similarity	NPC473342
0.8041	Intermediate Similarity	NPC45459
0.8041	Intermediate Similarity	NPC315491
0.8031	Intermediate Similarity	NPC171317
0.8	Intermediate Similarity	NPC54988
0.799	Intermediate Similarity	NPC478158
0.799	Intermediate Similarity	NPC293917
0.7959	Intermediate Similarity	NPC476874
0.7957	Intermediate Similarity	NPC71037
0.7956	Intermediate Similarity	NPC63751
0.7923	Intermediate Similarity	NPC314603
0.7919	Intermediate Similarity	NPC316069
0.7906	Intermediate Similarity	NPC243716
0.7898	Intermediate Similarity	NPC469786
0.7898	Intermediate Similarity	NPC469765
0.7898	Intermediate Similarity	NPC25008
0.7898	Intermediate Similarity	NPC73952
0.7898	Intermediate Similarity	NPC259644
0.7898	Intermediate Similarity	NPC469763
0.7898	Intermediate Similarity	NPC469760
0.7889	Intermediate Similarity	NPC194640
0.7889	Intermediate Similarity	NPC149265
0.7887	Intermediate Similarity	NPC272483
0.7861	Intermediate Similarity	NPC233936
0.7853	Intermediate Similarity	NPC75540
0.7853	Intermediate Similarity	NPC80597
0.7853	Intermediate Similarity	NPC212376
0.7853	Intermediate Similarity	NPC70922
0.7853	Intermediate Similarity	NPC211572
0.7849	Intermediate Similarity	NPC276540
0.7849	Intermediate Similarity	NPC233050
0.7846	Intermediate Similarity	NPC474389
0.7833	Intermediate Similarity	NPC54744
0.7826	Intermediate Similarity	NPC64055
0.7797	Intermediate Similarity	NPC141926
0.7794	Intermediate Similarity	NPC478157
0.7778	Intermediate Similarity	NPC165495
0.7778	Intermediate Similarity	NPC474195
0.7772	Intermediate Similarity	NPC477166
0.7772	Intermediate Similarity	NPC304187
0.7767	Intermediate Similarity	NPC281049
0.7766	Intermediate Similarity	NPC275292
0.7766	Intermediate Similarity	NPC243381
0.7765	Intermediate Similarity	NPC469762
0.776	Intermediate Similarity	NPC83111
0.7759	Intermediate Similarity	NPC314372
0.775	Intermediate Similarity	NPC82053
0.7747	Intermediate Similarity	NPC280864
0.7746	Intermediate Similarity	NPC190296
0.7745	Intermediate Similarity	NPC229348
0.7734	Intermediate Similarity	NPC82370
0.773	Intermediate Similarity	NPC288074
0.7725	Intermediate Similarity	NPC469358
0.7722	Intermediate Similarity	NPC230869
0.7713	Intermediate Similarity	NPC91179
0.7711	Intermediate Similarity	NPC54420
0.7709	Intermediate Similarity	NPC469785
0.7704	Intermediate Similarity	NPC227582
0.7701	Intermediate Similarity	NPC59269
0.7701	Intermediate Similarity	NPC248454
0.7696	Intermediate Similarity	NPC75634
0.7692	Intermediate Similarity	NPC311276
0.7688	Intermediate Similarity	NPC469938
0.7677	Intermediate Similarity	NPC106771
0.7677	Intermediate Similarity	NPC303820
0.7677	Intermediate Similarity	NPC213308
0.7677	Intermediate Similarity	NPC23420
0.7677	Intermediate Similarity	NPC205254
0.7665	Intermediate Similarity	NPC473640
0.7656	Intermediate Similarity	NPC278434
0.7638	Intermediate Similarity	NPC52909
0.7638	Intermediate Similarity	NPC475506
0.7638	Intermediate Similarity	NPC94211
0.7638	Intermediate Similarity	NPC475935
0.7635	Intermediate Similarity	NPC162860
0.763	Intermediate Similarity	NPC474196
0.7626	Intermediate Similarity	NPC477004
0.7626	Intermediate Similarity	NPC100321
0.7621	Intermediate Similarity	NPC313640
0.7617	Intermediate Similarity	NPC175474
0.7612	Intermediate Similarity	NPC470505
0.7604	Intermediate Similarity	NPC474707
0.76	Intermediate Similarity	NPC155143
0.7592	Intermediate Similarity	NPC110158
0.7588	Intermediate Similarity	NPC252338
0.7582	Intermediate Similarity	NPC131718
0.7577	Intermediate Similarity	NPC154339
0.7565	Intermediate Similarity	NPC204565
0.7565	Intermediate Similarity	NPC317030
0.7563	Intermediate Similarity	NPC11445
0.7562	Intermediate Similarity	NPC476098
0.7557	Intermediate Similarity	NPC159856
0.7551	Intermediate Similarity	NPC267343
0.7539	Intermediate Similarity	NPC163055
0.7538	Intermediate Similarity	NPC473763
0.7538	Intermediate Similarity	NPC117244
0.7527	Intermediate Similarity	NPC97343
0.7526	Intermediate Similarity	NPC65215
0.7526	Intermediate Similarity	NPC173028
0.7525	Intermediate Similarity	NPC156704
0.7524	Intermediate Similarity	NPC471194
0.7524	Intermediate Similarity	NPC471193
0.7514	Intermediate Similarity	NPC285469
0.7513	Intermediate Similarity	NPC294693
0.7513	Intermediate Similarity	NPC157828
0.7513	Intermediate Similarity	NPC195239
0.7513	Intermediate Similarity	NPC202812
0.7512	Intermediate Similarity	NPC57398
0.7512	Intermediate Similarity	NPC193761
0.75	Intermediate Similarity	NPC40779
0.75	Intermediate Similarity	NPC63031
0.75	Intermediate Similarity	NPC470497
0.7487	Intermediate Similarity	NPC131887
0.7487	Intermediate Similarity	NPC67288
0.7486	Intermediate Similarity	NPC24678
0.7486	Intermediate Similarity	NPC105818
0.7474	Intermediate Similarity	NPC248462
0.7473	Intermediate Similarity	NPC201700
0.7472	Intermediate Similarity	NPC471957
0.7471	Intermediate Similarity	NPC73767
0.7471	Intermediate Similarity	NPC110126
0.7463	Intermediate Similarity	NPC223791
0.7463	Intermediate Similarity	NPC107077
0.7462	Intermediate Similarity	NPC472210
0.7462	Intermediate Similarity	NPC247735
0.7462	Intermediate Similarity	NPC81802
0.7462	Intermediate Similarity	NPC472295
0.7462	Intermediate Similarity	NPC269886
0.7457	Intermediate Similarity	NPC84911
0.7451	Intermediate Similarity	NPC323927
0.7451	Intermediate Similarity	NPC88008
0.745	Intermediate Similarity	NPC220797
0.745	Intermediate Similarity	NPC268744
0.745	Intermediate Similarity	NPC237414
0.745	Intermediate Similarity	NPC474318
0.745	Intermediate Similarity	NPC153123
0.745	Intermediate Similarity	NPC475914
0.745	Intermediate Similarity	NPC201266
0.7449	Intermediate Similarity	NPC138370
0.744	Intermediate Similarity	NPC153980
0.744	Intermediate Similarity	NPC118940
0.744	Intermediate Similarity	NPC6865
0.7426	Intermediate Similarity	NPC476073
0.7421	Intermediate Similarity	NPC64436
0.7418	Intermediate Similarity	NPC64216
0.7416	Intermediate Similarity	NPC36405
0.7413	Intermediate Similarity	NPC13456
0.7413	Intermediate Similarity	NPC166209
0.7413	Intermediate Similarity	NPC77241
0.7413	Intermediate Similarity	NPC269203
0.7411	Intermediate Similarity	NPC472292
0.7407	Intermediate Similarity	NPC280297
0.7405	Intermediate Similarity	NPC102423
0.74	Intermediate Similarity	NPC470499
0.74	Intermediate Similarity	NPC306376
0.74	Intermediate Similarity	NPC52557
0.7399	Intermediate Similarity	NPC261195
0.7399	Intermediate Similarity	NPC29886
0.7399	Intermediate Similarity	NPC96102

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 NPC179701 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	560
0.2-0.3	1050
0.3-0.4	1987
0.4-0.5	2657
0.5-0.6	2015
0.6-0.7	598
0.7-0.8	82
0.8-0.85	2
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9017	High Similarity	NPD482	Approved
0.8966	High Similarity	NPD749	Clinical (unspecified phase)
0.8851	High Similarity	NPD750	Phase 2
0.8715	High Similarity	NPD2095	Phase 2
0.8715	High Similarity	NPD2092	Phase 2
0.8715	High Similarity	NPD2094	Phase 2
0.8667	High Similarity	NPD2091	Phase 2
0.8667	High Similarity	NPD2096	Phase 2
0.8407	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD484	Approved
0.8011	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7470	Discontinued
0.7839	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD6595	Phase 3
0.77	Intermediate Similarity	NPD5901	Discontinued
0.7638	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2144	Approved
0.76	Intermediate Similarity	NPD8073	Approved
0.7579	Intermediate Similarity	NPD3178	Discontinued
0.7563	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD8072	Approved
0.7552	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7970	Approved
0.7525	Intermediate Similarity	NPD8272	Phase 2
0.7514	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7619	Phase 3
0.7513	Intermediate Similarity	NPD7618	Phase 3
0.7513	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7957	Phase 1
0.7488	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD3038	Discontinued
0.7474	Intermediate Similarity	NPD8431	Approved
0.7473	Intermediate Similarity	NPD2844	Phase 3
0.7471	Intermediate Similarity	NPD786	Approved
0.7463	Intermediate Similarity	NPD4520	Approved
0.7452	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5426	Phase 3
0.7436	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD1183	Approved
0.7427	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5065	Approved
0.7399	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4499	Approved
0.7381	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1996	Discontinued
0.7346	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7944	Discontinued
0.7327	Intermediate Similarity	NPD4601	Approved
0.7327	Intermediate Similarity	NPD4600	Approved
0.732	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5818	Discontinued
0.7296	Intermediate Similarity	NPD3961	Discontinued
0.7292	Intermediate Similarity	NPD4079	Approved
0.7292	Intermediate Similarity	NPD4076	Approved
0.7287	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD3505	Approved
0.724	Intermediate Similarity	NPD3506	Approved
0.7236	Intermediate Similarity	NPD6665	Discontinued
0.7191	Intermediate Similarity	NPD1722	Approved
0.719	Intermediate Similarity	NPD8093	Discontinued
0.7186	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6664	Approved
0.7164	Intermediate Similarity	NPD4602	Approved
0.7163	Intermediate Similarity	NPD2509	Approved
0.7163	Intermediate Similarity	NPD2510	Approved
0.7158	Intermediate Similarity	NPD1325	Approved
0.7158	Intermediate Similarity	NPD1326	Approved
0.7157	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4341	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6178	Phase 3
0.7143	Intermediate Similarity	NPD3100	Discontinued
0.711	Intermediate Similarity	NPD7711	Discontinued
0.7108	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4075	Phase 2
0.7094	Intermediate Similarity	NPD7948	Phase 1
0.7089	Intermediate Similarity	NPD3389	Approved
0.7089	Intermediate Similarity	NPD3394	Approved
0.7089	Intermediate Similarity	NPD3393	Approved
0.7085	Intermediate Similarity	NPD1534	Approved
0.7078	Intermediate Similarity	NPD7731	Approved
0.7078	Intermediate Similarity	NPD7730	Approved
0.7072	Intermediate Similarity	NPD7953	Approved
0.7072	Intermediate Similarity	NPD7790	Approved
0.7072	Intermediate Similarity	NPD7950	Approved
0.7072	Intermediate Similarity	NPD7789	Approved
0.7072	Intermediate Similarity	NPD7951	Approved
0.7072	Intermediate Similarity	NPD7791	Approved
0.7072	Intermediate Similarity	NPD7952	Approved
0.7071	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7271	Approved
0.7047	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7603	Discontinued
0.703	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1038	Approved
0.7022	Intermediate Similarity	NPD2896	Discontinued
0.7021	Intermediate Similarity	NPD1404	Approved
0.7021	Intermediate Similarity	NPD1403	Approved
0.7014	Intermediate Similarity	NPD7824	Approved
0.7011	Intermediate Similarity	NPD2172	Phase 1
0.701	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5003	Discontinued
0.7005	Intermediate Similarity	NPD4326	Phase 2
0.6995	Remote Similarity	NPD8094	Discontinued
0.699	Remote Similarity	NPD4501	Approved
0.699	Remote Similarity	NPD4500	Approved
0.699	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7781	Approved
0.6968	Remote Similarity	NPD7780	Approved
0.6963	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4128	Approved
0.6957	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4948	Discontinued
0.6947	Remote Similarity	NPD1631	Approved
0.6946	Remote Similarity	NPD802	Phase 2
0.6943	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6999	Discontinued
0.6942	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7716	Approved
0.6941	Remote Similarity	NPD7717	Approved
0.6939	Remote Similarity	NPD8386	Phase 2
0.6938	Remote Similarity	NPD6987	Phase 1
0.6931	Remote Similarity	NPD2336	Approved
0.6931	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4462	Approved
0.6919	Remote Similarity	NPD4463	Approved
0.6911	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2305	Discontinued
0.6905	Remote Similarity	NPD7001	Phase 3
0.6904	Remote Similarity	NPD6452	Discontinued
0.6902	Remote Similarity	NPD4703	Approved
0.6902	Remote Similarity	NPD4702	Approved
0.6897	Remote Similarity	NPD5505	Discontinued
0.6888	Remote Similarity	NPD7865	Approved
0.6888	Remote Similarity	NPD4181	Approved
0.6884	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD2564	Approved
0.6881	Remote Similarity	NPD2565	Phase 2
0.6875	Remote Similarity	NPD2639	Approved
0.6875	Remote Similarity	NPD5017	Discontinued
0.6875	Remote Similarity	NPD2642	Approved
0.6875	Remote Similarity	NPD5611	Phase 2
0.6866	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3323	Discontinued
0.6845	Remote Similarity	NPD2837	Discontinued
0.6839	Remote Similarity	NPD4640	Approved
0.6839	Remote Similarity	NPD4639	Approved
0.6839	Remote Similarity	NPD2641	Approved
0.6839	Remote Similarity	NPD2640	Approved
0.6839	Remote Similarity	NPD4638	Approved
0.6834	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7234	Approved
0.6832	Remote Similarity	NPD7233	Approved
0.6829	Remote Similarity	NPD4427	Phase 2
0.6827	Remote Similarity	NPD5043	Discontinued
0.6818	Remote Similarity	NPD5899	Approved
0.6818	Remote Similarity	NPD5897	Approved
0.6818	Remote Similarity	NPD5898	Approved
0.6813	Remote Similarity	NPD1592	Phase 3
0.6812	Remote Similarity	NPD4397	Phase 1
0.6809	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1573	Approved
0.6804	Remote Similarity	NPD1575	Approved
0.6796	Remote Similarity	NPD2070	Approved
0.6796	Remote Similarity	NPD2307	Discontinued
0.6796	Remote Similarity	NPD2071	Approved
0.6796	Remote Similarity	NPD2068	Approved
0.6796	Remote Similarity	NPD2069	Approved
0.6791	Remote Similarity	NPD510	Phase 1
0.6789	Remote Similarity	NPD1630	Approved
0.6784	Remote Similarity	NPD5891	Approved
0.678	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6165	Phase 2
0.6771	Remote Similarity	NPD6164	Phase 2
0.6771	Remote Similarity	NPD3583	Phase 2
0.6761	Remote Similarity	NPD7666	Phase 3
0.6761	Remote Similarity	NPD7665	Phase 2
0.6749	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6479	Discontinued
0.6739	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6217	Discontinued
0.673	Remote Similarity	NPD6176	Phase 1
0.6727	Remote Similarity	NPD6242	Discontinued
0.6716	Remote Similarity	NPD7564	Discontinued

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