NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	225.13
Volume:	242.202
LogP:	1.901
LogD:	2.093
LogS:	-1.681
# Rotatable Bonds:	2
TPSA:	54.7
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	2.372
Fsp3:	0.214
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:	-5.151
MDCK Permeability:	3.689681989271776e-06
Pgp-inhibitor:	0.015
Pgp-substrate:	0.901
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.124
30% Bioavailability (F30%):	0.078

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.665
Plasma Protein Binding (PPB):	63.7190055847168%
Volume Distribution (VD):	1.351
Pgp-substrate:	25.34354019165039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.345
CYP2D6-inhibitor:	0.723
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	5.555
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.643
Human Hepatotoxicity (H-HT):	0.819
Drug-inuced Liver Injury (DILI):	0.129
AMES Toxicity:	0.909
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.797
Carcinogencity:	0.122
Eye Corrosion:	0.01
Eye Irritation:	0.035
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC115611

Natural Product ID:	NPC115611
*Common Name:**	Tebernine C
IUPAC Name:	2-(3-methyl-9H-pyrido[3,4-b]indol-1-yl)ethanamine
Synonyms:	Tebernine C
Standard InCHIKey:	XQZALXCDRFCRTM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H15N3/c1-9-8-11-10-4-2-3-5-12(10)17-14(11)13(16-9)6-7-15/h2-5,8,17H,6-7,15H2,1H3
SMILES:	NCCc1nc(C)cc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550999
PubChem CID:	44179505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO32684	tabernaemontana elegans	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19473031]
NPO32684	tabernaemontana elegans	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27704811]

☑ 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	6

Activity Type	# Activity
Cell Line	2
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	ID50	=	70.6	uM	PMID[568959]
NPT1864	Cell Line	L5178Y	Mus musculus	ID50	=	51.5	uM	PMID[568959]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	15.3	n.a.	PMID[568959]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	1.43	n.a.	PMID[568959]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	8.4	n.a.	PMID[568959]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.79	n.a.	PMID[568959]

☑ 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 NPC115611 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	1087
0.1-0.2	13211
0.2-0.3	18296
0.3-0.4	4683
0.4-0.5	2256
0.5-0.6	1656
0.6-0.7	1002
0.7-0.8	388
0.8-0.85	65
0.85-0.9	44
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC325252
0.9357	High Similarity	NPC321911
0.9328	High Similarity	NPC198988
0.9286	High Similarity	NPC179787
0.9286	High Similarity	NPC469811
0.9286	High Similarity	NPC201380
0.927	High Similarity	NPC284635
0.9214	High Similarity	NPC63545
0.903	High Similarity	NPC22079
0.9028	High Similarity	NPC325903
0.8921	High Similarity	NPC88097
0.8872	High Similarity	NPC250361
0.8857	High Similarity	NPC59084
0.8844	High Similarity	NPC236711
0.8841	High Similarity	NPC218268
0.8836	High Similarity	NPC476219
0.8836	High Similarity	NPC476297
0.8815	High Similarity	NPC473587
0.8794	High Similarity	NPC473868
0.8794	High Similarity	NPC63157
0.875	High Similarity	NPC475428
0.8741	High Similarity	NPC473762
0.8741	High Similarity	NPC204141
0.8741	High Similarity	NPC470440
0.8733	High Similarity	NPC317105
0.8725	High Similarity	NPC470204
0.8725	High Similarity	NPC122141
0.8723	High Similarity	NPC2949
0.8712	High Similarity	NPC41174
0.8686	High Similarity	NPC475450
0.8686	High Similarity	NPC179365
0.8667	High Similarity	NPC470203
0.8652	High Similarity	NPC110126
0.8643	High Similarity	NPC105127
0.8643	High Similarity	NPC84911
0.8571	High Similarity	NPC96102
0.8571	High Similarity	NPC261195
0.8571	High Similarity	NPC29886
0.8521	High Similarity	NPC73767
0.8493	Intermediate Similarity	NPC21605
0.8489	Intermediate Similarity	NPC473930
0.8462	Intermediate Similarity	NPC469784
0.8462	Intermediate Similarity	NPC469783
0.8462	Intermediate Similarity	NPC469779
0.8462	Intermediate Similarity	NPC469767
0.8462	Intermediate Similarity	NPC469768
0.8462	Intermediate Similarity	NPC469780
0.8462	Intermediate Similarity	NPC469761
0.8452	Intermediate Similarity	NPC82331
0.8431	Intermediate Similarity	NPC274229
0.8425	Intermediate Similarity	NPC288838
0.8411	Intermediate Similarity	NPC474880
0.8411	Intermediate Similarity	NPC475990
0.8411	Intermediate Similarity	NPC221786
0.8408	Intermediate Similarity	NPC474958
0.8403	Intermediate Similarity	NPC469766
0.838	Intermediate Similarity	NPC125746
0.8378	Intermediate Similarity	NPC53947
0.8367	Intermediate Similarity	NPC470111
0.8355	Intermediate Similarity	NPC229173
0.8345	Intermediate Similarity	NPC190296
0.8333	Intermediate Similarity	NPC279081
0.8286	Intermediate Similarity	NPC82295
0.8269	Intermediate Similarity	NPC97343
0.8258	Intermediate Similarity	NPC148140
0.8255	Intermediate Similarity	NPC33421
0.8231	Intermediate Similarity	NPC314372
0.8207	Intermediate Similarity	NPC230002
0.82	Intermediate Similarity	NPC470233
0.8195	Intermediate Similarity	NPC81561
0.8182	Intermediate Similarity	NPC225018
0.8176	Intermediate Similarity	NPC280852
0.8176	Intermediate Similarity	NPC478186
0.8176	Intermediate Similarity	NPC143872
0.8138	Intermediate Similarity	NPC312092
0.8134	Intermediate Similarity	NPC162689
0.8134	Intermediate Similarity	NPC54102
0.8133	Intermediate Similarity	NPC148592
0.8121	Intermediate Similarity	NPC471957
0.8117	Intermediate Similarity	NPC215584
0.8117	Intermediate Similarity	NPC44773
0.8108	Intermediate Similarity	NPC159856
0.8067	Intermediate Similarity	NPC2272
0.8067	Intermediate Similarity	NPC37548
0.8052	Intermediate Similarity	NPC56765
0.8041	Intermediate Similarity	NPC242556
0.8038	Intermediate Similarity	NPC474897
0.8015	Intermediate Similarity	NPC215519
0.8013	Intermediate Similarity	NPC247987
0.8013	Intermediate Similarity	NPC271797
0.8013	Intermediate Similarity	NPC40070
0.8013	Intermediate Similarity	NPC21174
0.8013	Intermediate Similarity	NPC478184
0.8013	Intermediate Similarity	NPC24678
0.8013	Intermediate Similarity	NPC105818
0.8	Intermediate Similarity	NPC471579
0.7987	Intermediate Similarity	NPC216643
0.7975	Intermediate Similarity	NPC191415
0.7975	Intermediate Similarity	NPC307191
0.7973	Intermediate Similarity	NPC20144
0.7961	Intermediate Similarity	NPC470823
0.795	Intermediate Similarity	NPC151635
0.7935	Intermediate Similarity	NPC135141
0.7935	Intermediate Similarity	NPC477591
0.7935	Intermediate Similarity	NPC92796
0.7914	Intermediate Similarity	NPC122718
0.7908	Intermediate Similarity	NPC141926
0.7908	Intermediate Similarity	NPC469760
0.7908	Intermediate Similarity	NPC73952
0.7908	Intermediate Similarity	NPC469763
0.7908	Intermediate Similarity	NPC200214
0.7908	Intermediate Similarity	NPC469786
0.7908	Intermediate Similarity	NPC259644
0.7908	Intermediate Similarity	NPC469765
0.7908	Intermediate Similarity	NPC25008
0.7898	Intermediate Similarity	NPC90723
0.7891	Intermediate Similarity	NPC104483
0.7881	Intermediate Similarity	NPC477134
0.7879	Intermediate Similarity	NPC284678
0.7871	Intermediate Similarity	NPC286427
0.7857	Intermediate Similarity	NPC212376
0.7857	Intermediate Similarity	NPC34844
0.7857	Intermediate Similarity	NPC75540
0.7857	Intermediate Similarity	NPC470507
0.7857	Intermediate Similarity	NPC80597
0.7857	Intermediate Similarity	NPC38736
0.7857	Intermediate Similarity	NPC70922
0.7857	Intermediate Similarity	NPC211572
0.7843	Intermediate Similarity	NPC216713
0.7829	Intermediate Similarity	NPC187951
0.7829	Intermediate Similarity	NPC124005
0.7821	Intermediate Similarity	NPC206819
0.7821	Intermediate Similarity	NPC41257
0.7821	Intermediate Similarity	NPC318065
0.7821	Intermediate Similarity	NPC293487
0.7818	Intermediate Similarity	NPC102755
0.7818	Intermediate Similarity	NPC48938
0.7806	Intermediate Similarity	NPC285469
0.7785	Intermediate Similarity	NPC478182
0.7763	Intermediate Similarity	NPC114209
0.7756	Intermediate Similarity	NPC299594
0.7755	Intermediate Similarity	NPC251722
0.7755	Intermediate Similarity	NPC314102
0.7751	Intermediate Similarity	NPC324091
0.7751	Intermediate Similarity	NPC231536
0.775	Intermediate Similarity	NPC317430
0.7722	Intermediate Similarity	NPC282231
0.7716	Intermediate Similarity	NPC472123
0.7716	Intermediate Similarity	NPC252572
0.7716	Intermediate Similarity	NPC161861
0.7714	Intermediate Similarity	NPC46358
0.7692	Intermediate Similarity	NPC141353
0.7692	Intermediate Similarity	NPC469785
0.7679	Intermediate Similarity	NPC62749
0.7677	Intermediate Similarity	NPC232798
0.766	Intermediate Similarity	NPC27740
0.7658	Intermediate Similarity	NPC279918
0.7651	Intermediate Similarity	NPC314394
0.7643	Intermediate Similarity	NPC469762
0.7636	Intermediate Similarity	NPC219336
0.7635	Intermediate Similarity	NPC150259
0.7628	Intermediate Similarity	NPC471458
0.7619	Intermediate Similarity	NPC133003
0.761	Intermediate Similarity	NPC16667
0.761	Intermediate Similarity	NPC478185
0.7607	Intermediate Similarity	NPC477611
0.7593	Intermediate Similarity	NPC91895
0.759	Intermediate Similarity	NPC469896
0.7582	Intermediate Similarity	NPC316069
0.7582	Intermediate Similarity	NPC129042
0.758	Intermediate Similarity	NPC184476
0.7578	Intermediate Similarity	NPC474561
0.7578	Intermediate Similarity	NPC478183
0.7578	Intermediate Similarity	NPC56233
0.7578	Intermediate Similarity	NPC49954
0.7576	Intermediate Similarity	NPC183662
0.7576	Intermediate Similarity	NPC15573
0.7576	Intermediate Similarity	NPC217372
0.7574	Intermediate Similarity	NPC143156
0.7562	Intermediate Similarity	NPC311276
0.7562	Intermediate Similarity	NPC271734
0.7561	Intermediate Similarity	NPC329688
0.7561	Intermediate Similarity	NPC189812
0.756	Intermediate Similarity	NPC472294
0.756	Intermediate Similarity	NPC108011
0.7558	Intermediate Similarity	NPC324149
0.7552	Intermediate Similarity	NPC476140
0.7547	Intermediate Similarity	NPC131718
0.7531	Intermediate Similarity	NPC63751
0.7529	Intermediate Similarity	NPC79356
0.7529	Intermediate Similarity	NPC102592
0.7516	Intermediate Similarity	NPC280864
0.7516	Intermediate Similarity	NPC17751
0.7516	Intermediate Similarity	NPC207726
0.7514	Intermediate Similarity	NPC326422
0.75	Intermediate Similarity	NPC470205
0.7485	Intermediate Similarity	NPC194411
0.7485	Intermediate Similarity	NPC32534
0.7484	Intermediate Similarity	NPC474791
0.7484	Intermediate Similarity	NPC230869

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 NPC115611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	433
0.1-0.2	867
0.2-0.3	995
0.3-0.4	2017
0.4-0.5	2261
0.5-0.6	1740
0.6-0.7	669
0.7-0.8	152
0.8-0.85	10
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8865	High Similarity	NPD4637	Clinical (unspecified phase)
0.8662	High Similarity	NPD1722	Approved
0.8592	High Similarity	NPD3943	Clinical (unspecified phase)
0.8571	High Similarity	NPD198	Clinical (unspecified phase)
0.8521	High Similarity	NPD786	Approved
0.8429	Intermediate Similarity	NPD3385	Approved
0.8425	Intermediate Similarity	NPD1683	Approved
0.8414	Intermediate Similarity	NPD5254	Discontinued
0.8389	Intermediate Similarity	NPD2837	Discontinued
0.838	Intermediate Similarity	NPD1262	Discovery
0.8255	Intermediate Similarity	NPD4462	Approved
0.8255	Intermediate Similarity	NPD4463	Approved
0.8188	Intermediate Similarity	NPD3100	Discontinued
0.8188	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD3654	Approved
0.8143	Intermediate Similarity	NPD947	Approved
0.8065	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1254	Approved
0.8056	Intermediate Similarity	NPD1253	Approved
0.8056	Intermediate Similarity	NPD1256	Approved
0.8056	Intermediate Similarity	NPD1255	Approved
0.8013	Intermediate Similarity	NPD3323	Discontinued
0.8013	Intermediate Similarity	NPD2172	Phase 1
0.7962	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD715	Phase 3
0.7933	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1561	Phase 2
0.7881	Intermediate Similarity	NPD4547	Phase 3
0.7877	Intermediate Similarity	NPD45	Approved
0.7877	Intermediate Similarity	NPD6554	Approved
0.7872	Intermediate Similarity	NPD991	Phase 2
0.7872	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD2006	Phase 2
0.7829	Intermediate Similarity	NPD2430	Phase 2
0.7805	Intermediate Similarity	NPD5962	Phase 2
0.7778	Intermediate Similarity	NPD1251	Discontinued
0.7764	Intermediate Similarity	NPD6828	Phase 2
0.7764	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1895	Discontinued
0.7756	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2641	Approved
0.775	Intermediate Similarity	NPD2640	Approved
0.7742	Intermediate Similarity	NPD977	Approved
0.7742	Intermediate Similarity	NPD976	Approved
0.7742	Intermediate Similarity	NPD975	Approved
0.7716	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2150	Discontinued
0.7683	Intermediate Similarity	NPD4181	Approved
0.7682	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5065	Approved
0.7662	Intermediate Similarity	NPD3835	Phase 3
0.7662	Intermediate Similarity	NPD3833	Phase 3
0.7658	Intermediate Similarity	NPD1403	Approved
0.7658	Intermediate Similarity	NPD1404	Approved
0.7654	Intermediate Similarity	NPD3610	Approved
0.7654	Intermediate Similarity	NPD3609	Approved
0.7625	Intermediate Similarity	NPD1313	Approved
0.7625	Intermediate Similarity	NPD509	Phase 3
0.7619	Intermediate Similarity	NPD4880	Discontinued
0.7616	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3476	Approved
0.7586	Intermediate Similarity	NPD3475	Approved
0.758	Intermediate Similarity	NPD2927	Phase 3
0.7561	Intermediate Similarity	NPD4128	Approved
0.755	Intermediate Similarity	NPD1592	Phase 3
0.7545	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD803	Phase 1
0.7531	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5787	Discontinued
0.7515	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4047	Discontinued
0.75	Intermediate Similarity	NPD2118	Approved
0.75	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2119	Approved
0.7485	Intermediate Similarity	NPD1326	Approved
0.7485	Intermediate Similarity	NPD1325	Approved
0.7469	Intermediate Similarity	NPD2642	Approved
0.7469	Intermediate Similarity	NPD2639	Approved
0.7451	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4326	Phase 2
0.7421	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD680	Discontinued
0.741	Intermediate Similarity	NPD4075	Phase 2
0.7405	Intermediate Similarity	NPD2165	Phase 1
0.7386	Intermediate Similarity	NPD2880	Discontinued
0.7381	Intermediate Similarity	NPD6595	Phase 3
0.7381	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5473	Discontinued
0.7378	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5436	Phase 1
0.7376	Intermediate Similarity	NPD4811	Discontinued
0.7365	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1248	Discontinued
0.7358	Intermediate Similarity	NPD3112	Approved
0.7358	Intermediate Similarity	NPD3115	Approved
0.7358	Intermediate Similarity	NPD2580	Discontinued
0.7358	Intermediate Similarity	NPD3113	Approved
0.7358	Intermediate Similarity	NPD3114	Approved
0.7358	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4509	Discontinued
0.7326	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD268	Approved
0.7324	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD9598	Discontinued
0.7324	Intermediate Similarity	NPD271	Approved
0.7321	Intermediate Similarity	NPD40	Phase 2
0.7321	Intermediate Similarity	NPD5730	Phase 2
0.7321	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5021	Discontinued
0.7315	Intermediate Similarity	NPD4029	Approved
0.7315	Intermediate Similarity	NPD4030	Approved
0.7315	Intermediate Similarity	NPD4028	Approved
0.731	Intermediate Similarity	NPD9583	Approved
0.7308	Intermediate Similarity	NPD1661	Suspended
0.7296	Intermediate Similarity	NPD6285	Phase 2
0.7286	Intermediate Similarity	NPD9392	Approved
0.7286	Intermediate Similarity	NPD9396	Approved
0.7284	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2882	Phase 1
0.7273	Intermediate Similarity	NPD7618	Phase 3
0.7273	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7619	Phase 3
0.7267	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3505	Approved
0.7262	Intermediate Similarity	NPD3506	Approved
0.7256	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1215	Discontinued
0.7241	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5138	Approved
0.7239	Intermediate Similarity	NPD5140	Approved
0.7235	Intermediate Similarity	NPD1707	Approved
0.7235	Intermediate Similarity	NPD1708	Approved
0.7225	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3961	Discontinued
0.7225	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4079	Approved
0.7219	Intermediate Similarity	NPD4076	Approved
0.7212	Intermediate Similarity	NPD2333	Discontinued
0.7202	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3944	Approved
0.72	Intermediate Similarity	NPD3942	Approved
0.7195	Intermediate Similarity	NPD2915	Discontinued
0.7193	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3320	Approved
0.7193	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5105	Approved
0.7193	Intermediate Similarity	NPD3319	Phase 1
0.7193	Intermediate Similarity	NPD4441	Phase 2
0.7193	Intermediate Similarity	NPD5106	Approved
0.7193	Intermediate Similarity	NPD3318	Approved
0.719	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2443	Approved
0.7174	Intermediate Similarity	NPD2442	Approved
0.7172	Intermediate Similarity	NPD9357	Approved
0.717	Intermediate Similarity	NPD6158	Phase 2
0.717	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5418	Discontinued
0.716	Intermediate Similarity	NPD2144	Approved
0.7151	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1598	Discontinued
0.7143	Intermediate Similarity	NPD6492	Phase 2
0.7143	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD482	Approved
0.7135	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD8386	Phase 2
0.711	Intermediate Similarity	NPD1227	Phase 2
0.7105	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5020	Approved
0.7097	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3512	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1597	Phase 1
0.7073	Intermediate Similarity	NPD1016	Phase 2
0.7073	Intermediate Similarity	NPD5315	Discontinued
0.7073	Intermediate Similarity	NPD1015	Phase 2
0.7073	Intermediate Similarity	NPD2480	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2591	Phase 2
0.7069	Intermediate Similarity	NPD2793	Discontinued
0.7069	Intermediate Similarity	NPD6217	Discontinued
0.7059	Intermediate Similarity	NPD7111	Discontinued
0.7056	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6469	Phase 3
0.7052	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6794	Approved
0.7045	Intermediate Similarity	NPD4499	Approved
0.7041	Intermediate Similarity	NPD3799	Suspended
0.7035	Intermediate Similarity	NPD7867	Phase 1

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