NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	474.01
Volume:	381.713
LogP:	4.455
LogD:	2.843
LogS:	-3.888
# Rotatable Bonds:	5
TPSA:	83.62
# H-Bond Aceptor:	4
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	3.29
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.644
MDCK Permeability:	3.81E-06
Pgp-inhibitor:	0.907
Pgp-substrate:	0.118
Human Intestinal Absorption (HIA):	0.054
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	93.05%
Volume Distribution (VD):	1.99
Pgp-substrate:	8.11%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.538
CYP2C9-substrate:	0.802
CYP2D6-inhibitor:	0.979
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	3.049
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.962
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.473
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.661
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.35
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC477611

Natural Product ID:	NPC477611
*Common Name:**	Gelliusine E
IUPAC Name:	2-[3-(2-aminoethyl)-6-bromo-1H-indol-2-yl]-2-(6-bromo-1H-indol-3-yl)ethanamine
Synonyms:	(+/-)-Gelliusine F
Standard InCHIKey:	OIMJVUYYZQBQMK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20Br2N4/c21-11-2-4-14-17(10-25-18(14)7-11)16(9-24)20-15(5-6-23)13-3-1-12(22)8-19(13)26-20/h1-4,7-8,10,16,25-26H,5-6,9,23-24H2
SMILES:	C1=CC2=C(C=C1Br)NC=C2C(CN)C3=C(C4=C(N3)C=C(C=C4)Br)CCN
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10254385
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines and derivatives

*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
NPO33565	Orina sp.	Species	n.a.	n.a.	n.a.	New Caledonian, stations DW 114-115, at a depth of 255-285 m	n.a.	PMID[7595591]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	3

Activity Type	# Activity
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT230	Individual Protein	Bradykinin B2 receptor	Homo sapiens	Inhibition	=	89	%	PMID[7595591]
NPT7211	Individual Protein	Somatostatin receptor	Rattus norvegicus	Activity	=	91	%	PMID[7595591]
NPT2	Others	Unspecified		Inhibition	=	67	%	PMID[7595591]
NPT2	Others	Unspecified		IC50	=	10000	nM	PMID[7595591]

☑ 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 NPC477611 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	1267
0.1-0.2	15319
0.2-0.3	17586
0.3-0.4	3862
0.4-0.5	1988
0.5-0.6	1480
0.6-0.7	839
0.7-0.8	281
0.8-0.85	52
0.85-0.9	20
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9038	High Similarity	NPC141926
0.9024	High Similarity	NPC474958
0.9	High Similarity	NPC231536
0.891	High Similarity	NPC53947
0.8841	High Similarity	NPC82331
0.8839	High Similarity	NPC288838
0.8827	High Similarity	NPC274229
0.8827	High Similarity	NPC17751
0.8698	High Similarity	NPC307191
0.865	High Similarity	NPC149265
0.8634	High Similarity	NPC216643
0.8608	High Similarity	NPC2272
0.8603	High Similarity	NPC94211
0.8603	High Similarity	NPC52909
0.8603	High Similarity	NPC475935
0.8547	High Similarity	NPC23420
0.8547	High Similarity	NPC205254
0.8547	High Similarity	NPC77241
0.8547	High Similarity	NPC303820
0.8547	High Similarity	NPC166209
0.8547	High Similarity	NPC106771
0.8547	High Similarity	NPC269203
0.8547	High Similarity	NPC13456
0.8512	High Similarity	NPC280297
0.8509	High Similarity	NPC34844
0.8492	Intermediate Similarity	NPC220797
0.8492	Intermediate Similarity	NPC153123
0.8492	Intermediate Similarity	NPC201266
0.8492	Intermediate Similarity	NPC474318
0.8492	Intermediate Similarity	NPC475914
0.8492	Intermediate Similarity	NPC268744
0.8466	Intermediate Similarity	NPC135141
0.8466	Intermediate Similarity	NPC92796
0.8373	Intermediate Similarity	NPC280864
0.8365	Intermediate Similarity	NPC316069
0.8333	Intermediate Similarity	NPC97343
0.8323	Intermediate Similarity	NPC105127
0.8313	Intermediate Similarity	NPC317105
0.828	Intermediate Similarity	NPC469767
0.828	Intermediate Similarity	NPC469783
0.828	Intermediate Similarity	NPC469779
0.828	Intermediate Similarity	NPC469784
0.828	Intermediate Similarity	NPC469761
0.828	Intermediate Similarity	NPC469768
0.828	Intermediate Similarity	NPC469780
0.8276	Intermediate Similarity	NPC108011
0.8258	Intermediate Similarity	NPC96102
0.8228	Intermediate Similarity	NPC469766
0.8221	Intermediate Similarity	NPC325903
0.8217	Intermediate Similarity	NPC110126
0.8217	Intermediate Similarity	NPC73767
0.8205	Intermediate Similarity	NPC84911
0.8204	Intermediate Similarity	NPC247987
0.8141	Intermediate Similarity	NPC261195
0.8141	Intermediate Similarity	NPC29886
0.8105	Intermediate Similarity	NPC477610
0.8086	Intermediate Similarity	NPC469811
0.8056	Intermediate Similarity	NPC304187
0.8056	Intermediate Similarity	NPC477166
0.8056	Intermediate Similarity	NPC473342
0.8056	Intermediate Similarity	NPC477167
0.805	Intermediate Similarity	NPC279081
0.8046	Intermediate Similarity	NPC276540
0.8046	Intermediate Similarity	NPC233050
0.8037	Intermediate Similarity	NPC321911
0.8035	Intermediate Similarity	NPC280852
0.8025	Intermediate Similarity	NPC143872
0.8025	Intermediate Similarity	NPC63545
0.8011	Intermediate Similarity	NPC188821
0.8011	Intermediate Similarity	NPC474180
0.801	Intermediate Similarity	NPC470703
0.8	Intermediate Similarity	NPC82295
0.7989	Intermediate Similarity	NPC59269
0.7987	Intermediate Similarity	NPC316811
0.7979	Intermediate Similarity	NPC477114
0.7975	Intermediate Similarity	NPC201380
0.7975	Intermediate Similarity	NPC179787
0.7964	Intermediate Similarity	NPC286427
0.7963	Intermediate Similarity	NPC314372
0.7958	Intermediate Similarity	NPC473218
0.7958	Intermediate Similarity	NPC470702
0.7955	Intermediate Similarity	NPC243381
0.7955	Intermediate Similarity	NPC275292
0.795	Intermediate Similarity	NPC190296
0.7939	Intermediate Similarity	NPC470233
0.7937	Intermediate Similarity	NPC230002
0.7929	Intermediate Similarity	NPC470203
0.7917	Intermediate Similarity	NPC206819
0.7917	Intermediate Similarity	NPC318065
0.7917	Intermediate Similarity	NPC56765
0.7917	Intermediate Similarity	NPC41257
0.7892	Intermediate Similarity	NPC232798
0.7879	Intermediate Similarity	NPC105818
0.7879	Intermediate Similarity	NPC24678
0.787	Intermediate Similarity	NPC44773
0.787	Intermediate Similarity	NPC215584
0.787	Intermediate Similarity	NPC470204
0.7853	Intermediate Similarity	NPC159856
0.7846	Intermediate Similarity	NPC477609
0.7838	Intermediate Similarity	NPC474389
0.7821	Intermediate Similarity	NPC308931
0.7821	Intermediate Similarity	NPC99939
0.7821	Intermediate Similarity	NPC15102
0.7816	Intermediate Similarity	NPC64055
0.7797	Intermediate Similarity	NPC314919
0.7796	Intermediate Similarity	NPC237414
0.7796	Intermediate Similarity	NPC477004
0.7791	Intermediate Similarity	NPC109447
0.7784	Intermediate Similarity	NPC469765
0.7784	Intermediate Similarity	NPC259644
0.7784	Intermediate Similarity	NPC469786
0.7784	Intermediate Similarity	NPC469760
0.7784	Intermediate Similarity	NPC73952
0.7784	Intermediate Similarity	NPC25008
0.7784	Intermediate Similarity	NPC469763
0.7766	Intermediate Similarity	NPC473761
0.7765	Intermediate Similarity	NPC122141
0.7765	Intermediate Similarity	NPC229173
0.7765	Intermediate Similarity	NPC110158
0.7758	Intermediate Similarity	NPC471957
0.7738	Intermediate Similarity	NPC75540
0.7738	Intermediate Similarity	NPC70922
0.7738	Intermediate Similarity	NPC80597
0.7738	Intermediate Similarity	NPC211572
0.7738	Intermediate Similarity	NPC212376
0.7733	Intermediate Similarity	NPC2165
0.7716	Intermediate Similarity	NPC59084
0.7706	Intermediate Similarity	NPC474880
0.7706	Intermediate Similarity	NPC475990
0.7706	Intermediate Similarity	NPC221786
0.7692	Intermediate Similarity	NPC469785
0.7679	Intermediate Similarity	NPC200214
0.7677	Intermediate Similarity	NPC250361
0.7674	Intermediate Similarity	NPC90723
0.7673	Intermediate Similarity	NPC477608
0.7673	Intermediate Similarity	NPC477607
0.7669	Intermediate Similarity	NPC63157
0.7669	Intermediate Similarity	NPC473868
0.7658	Intermediate Similarity	NPC475450
0.7647	Intermediate Similarity	NPC469762
0.7647	Intermediate Similarity	NPC236711
0.7644	Intermediate Similarity	NPC63751
0.7619	Intermediate Similarity	NPC470823
0.7619	Intermediate Similarity	NPC216713
0.7614	Intermediate Similarity	NPC288074
0.761	Intermediate Similarity	NPC473930
0.7607	Intermediate Similarity	NPC115611
0.76	Intermediate Similarity	NPC194411
0.7596	Intermediate Similarity	NPC321708
0.7595	Intermediate Similarity	NPC475428
0.7595	Intermediate Similarity	NPC22079
0.7586	Intermediate Similarity	NPC160105
0.7586	Intermediate Similarity	NPC474561
0.7586	Intermediate Similarity	NPC49954
0.7584	Intermediate Similarity	NPC284775
0.758	Intermediate Similarity	NPC473762
0.7578	Intermediate Similarity	NPC325252
0.7578	Intermediate Similarity	NPC218268
0.7543	Intermediate Similarity	NPC201700
0.7532	Intermediate Similarity	NPC473587
0.7531	Intermediate Similarity	NPC125746
0.7531	Intermediate Similarity	NPC150259
0.7531	Intermediate Similarity	NPC251722
0.7531	Intermediate Similarity	NPC314102
0.7527	Intermediate Similarity	NPC88315
0.7516	Intermediate Similarity	NPC198988
0.75	Intermediate Similarity	NPC2949
0.75	Intermediate Similarity	NPC474897
0.7476	Intermediate Similarity	NPC63031
0.7472	Intermediate Similarity	NPC37423
0.7472	Intermediate Similarity	NPC275305
0.7471	Intermediate Similarity	NPC311276
0.7457	Intermediate Similarity	NPC279918
0.7456	Intermediate Similarity	NPC40070
0.744	Intermediate Similarity	NPC21605
0.744	Intermediate Similarity	NPC470111
0.7439	Intermediate Similarity	NPC88097
0.7438	Intermediate Similarity	NPC179365
0.7433	Intermediate Similarity	NPC304203
0.7425	Intermediate Similarity	NPC204141
0.7419	Intermediate Similarity	NPC476460
0.7418	Intermediate Similarity	NPC83381
0.7416	Intermediate Similarity	NPC314603
0.7414	Intermediate Similarity	NPC253687
0.7414	Intermediate Similarity	NPC282231
0.7411	Intermediate Similarity	NPC207020
0.7403	Intermediate Similarity	NPC16659
0.7403	Intermediate Similarity	NPC164228
0.7394	Intermediate Similarity	NPC284635
0.7389	Intermediate Similarity	NPC68354
0.7386	Intermediate Similarity	NPC49217
0.738	Intermediate Similarity	NPC316359
0.738	Intermediate Similarity	NPC315617
0.7374	Intermediate Similarity	NPC471579
0.7371	Intermediate Similarity	NPC40779
0.7356	Intermediate Similarity	NPC474357
0.7356	Intermediate Similarity	NPC131718
0.7353	Intermediate Similarity	NPC33421
0.7348	Intermediate Similarity	NPC215795
0.7348	Intermediate Similarity	NPC265710

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 NPC477611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	485
0.1-0.2	987
0.2-0.3	1174
0.3-0.4	2361
0.4-0.5	2221
0.5-0.6	1407
0.6-0.7	431
0.7-0.8	80
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1722	Approved
0.8258	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD786	Approved
0.821	Intermediate Similarity	NPD2172	Phase 1
0.811	Intermediate Similarity	NPD2837	Discontinued
0.8037	Intermediate Similarity	NPD3100	Discontinued
0.7987	Intermediate Similarity	NPD2070	Approved
0.7987	Intermediate Similarity	NPD2068	Approved
0.7987	Intermediate Similarity	NPD2071	Approved
0.7987	Intermediate Similarity	NPD2069	Approved
0.7898	Intermediate Similarity	NPD6595	Phase 3
0.7886	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3323	Discontinued
0.7824	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2639	Approved
0.7688	Intermediate Similarity	NPD2642	Approved
0.7654	Intermediate Similarity	NPD1895	Discontinued
0.7644	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1995	Approved
0.761	Intermediate Similarity	NPD1994	Approved
0.761	Intermediate Similarity	NPD1993	Approved
0.7576	Intermediate Similarity	NPD5254	Discontinued
0.7571	Intermediate Similarity	NPD5065	Approved
0.7557	Intermediate Similarity	NPD3610	Approved
0.7557	Intermediate Similarity	NPD3609	Approved
0.7545	Intermediate Similarity	NPD4547	Phase 3
0.7543	Intermediate Similarity	NPD2641	Approved
0.7543	Intermediate Similarity	NPD2640	Approved
0.7528	Intermediate Similarity	NPD4075	Phase 2
0.7515	Intermediate Similarity	NPD2006	Phase 2
0.7514	Intermediate Similarity	NPD5105	Approved
0.7514	Intermediate Similarity	NPD5106	Approved
0.75	Intermediate Similarity	NPD2430	Phase 2
0.75	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4181	Approved
0.7486	Intermediate Similarity	NPD6217	Discontinued
0.7472	Intermediate Similarity	NPD4128	Approved
0.7459	Intermediate Similarity	NPD1708	Approved
0.7459	Intermediate Similarity	NPD1707	Approved
0.7457	Intermediate Similarity	NPD1404	Approved
0.7457	Intermediate Similarity	NPD1403	Approved
0.7456	Intermediate Similarity	NPD4462	Approved
0.7456	Intermediate Similarity	NPD4463	Approved
0.7453	Intermediate Similarity	NPD3385	Approved
0.7447	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1262	Discovery
0.7418	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD991	Phase 2
0.7405	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5436	Phase 1
0.7389	Intermediate Similarity	NPD3506	Approved
0.7389	Intermediate Similarity	NPD3505	Approved
0.7354	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4076	Approved
0.7348	Intermediate Similarity	NPD4079	Approved
0.7345	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3654	Approved
0.7305	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2118	Approved
0.7296	Intermediate Similarity	NPD2119	Approved
0.7294	Intermediate Similarity	NPD1183	Approved
0.7267	Intermediate Similarity	NPD3475	Approved
0.7267	Intermediate Similarity	NPD3476	Approved
0.7258	Intermediate Similarity	NPD8431	Approved
0.7258	Intermediate Similarity	NPD3961	Discontinued
0.7247	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD2144	Approved
0.7184	Intermediate Similarity	NPD2580	Discontinued
0.7181	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1683	Approved
0.7174	Intermediate Similarity	NPD3038	Discontinued
0.7151	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4030	Approved
0.7134	Intermediate Similarity	NPD4029	Approved
0.7134	Intermediate Similarity	NPD4028	Approved
0.7126	Intermediate Similarity	NPD2165	Phase 1
0.712	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD803	Phase 1
0.7112	Intermediate Similarity	NPD2793	Discontinued
0.7108	Intermediate Similarity	NPD6554	Approved
0.7108	Intermediate Similarity	NPD45	Approved
0.7097	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3115	Approved
0.7086	Intermediate Similarity	NPD3113	Approved
0.7086	Intermediate Similarity	NPD3112	Approved
0.7086	Intermediate Similarity	NPD3114	Approved
0.7081	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5426	Phase 3
0.7052	Intermediate Similarity	NPD3833	Phase 3
0.7052	Intermediate Similarity	NPD3835	Phase 3
0.7041	Intermediate Similarity	NPD3015	Discontinued
0.7031	Intermediate Similarity	NPD7619	Phase 3
0.7031	Intermediate Similarity	NPD7618	Phase 3
0.7022	Intermediate Similarity	NPD5315	Discontinued
0.7	Intermediate Similarity	NPD6133	Discontinued
0.7	Intermediate Similarity	NPD1248	Discontinued
0.6995	Remote Similarity	NPD482	Approved
0.6988	Remote Similarity	NPD4880	Discontinued
0.6984	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7948	Phase 1
0.6959	Remote Similarity	NPD6664	Approved
0.6957	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD2094	Phase 2
0.6952	Remote Similarity	NPD2092	Phase 2
0.6952	Remote Similarity	NPD2095	Phase 2
0.6946	Remote Similarity	NPD1256	Approved
0.6946	Remote Similarity	NPD1253	Approved
0.6946	Remote Similarity	NPD1255	Approved
0.6946	Remote Similarity	NPD1254	Approved
0.6944	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD975	Approved
0.6932	Remote Similarity	NPD977	Approved
0.6932	Remote Similarity	NPD976	Approved
0.6931	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3942	Approved
0.6928	Remote Similarity	NPD3944	Approved
0.6927	Remote Similarity	NPD4615	Phase 2
0.6927	Remote Similarity	NPD3404	Approved
0.6923	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2096	Phase 2
0.6915	Remote Similarity	NPD2091	Phase 2
0.69	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2150	Discontinued
0.6891	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.689	Remote Similarity	NPD947	Approved
0.6888	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6828	Phase 2
0.6881	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1598	Discontinued
0.6868	Remote Similarity	NPD4639	Approved
0.6868	Remote Similarity	NPD5021	Discontinued
0.6868	Remote Similarity	NPD4638	Approved
0.6868	Remote Similarity	NPD4640	Approved
0.6865	Remote Similarity	NPD2367	Phase 2
0.6863	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD715	Phase 3
0.6842	Remote Similarity	NPD5642	Approved
0.6828	Remote Similarity	NPD7111	Discontinued
0.6825	Remote Similarity	NPD7564	Discontinued
0.6824	Remote Similarity	NPD2075	Approved
0.6824	Remote Similarity	NPD2074	Approved
0.6824	Remote Similarity	NPD2072	Approved
0.6824	Remote Similarity	NPD2073	Approved
0.6821	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7445	Phase 1
0.6813	Remote Similarity	NPD271	Approved
0.6813	Remote Similarity	NPD268	Approved
0.6813	Remote Similarity	NPD270	Clinical (unspecified phase)
0.681	Remote Similarity	NPD9583	Approved
0.6804	Remote Similarity	NPD2445	Approved
0.6804	Remote Similarity	NPD2446	Approved
0.6798	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2880	Discontinued
0.678	Remote Similarity	NPD3339	Approved
0.6776	Remote Similarity	NPD2333	Discontinued
0.6772	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD9396	Approved
0.6772	Remote Similarity	NPD9392	Approved
0.6765	Remote Similarity	NPD7470	Discontinued
0.6761	Remote Similarity	NPD971	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4326	Phase 2
0.6757	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5962	Phase 2
0.6755	Remote Similarity	NPD5473	Discontinued
0.6753	Remote Similarity	NPD4922	Phase 2
0.675	Remote Similarity	NPD8072	Approved
0.674	Remote Similarity	NPD6771	Discontinued
0.6739	Remote Similarity	NPD1325	Approved
0.6739	Remote Similarity	NPD1326	Approved
0.6737	Remote Similarity	NPD4957	Phase 2
0.6737	Remote Similarity	NPD5892	Approved
0.6732	Remote Similarity	NPD2411	Approved
0.6724	Remote Similarity	NPD5995	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