NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.05
Volume:	211.825
LogP:	3.927
LogD:	3.747
LogS:	-5.529
# Rotatable Bonds:	0
TPSA:	17.82
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	2.252
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.484
MDCK Permeability:	2.43E-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.64
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.894
Plasma Protein Binding (PPB):	86.74%
Volume Distribution (VD):	1.872
Pgp-substrate:	12.32%

ADMET: Metabolism

CYP1A2-inhibitor:	0.995
CYP1A2-substrate:	0.734
CYP2C19-inhibitor:	0.611
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.648
CYP2D6-inhibitor:	0.798
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	9.37
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.764
AMES Toxicity:	0.79
Rat Oral Acute Toxicity:	0.636
Maximum Recommended Daily Dose:	0.708
Skin Sensitization:	0.081
Carcinogencity:	0.804
Eye Corrosion:	0.005
Eye Irritation:	0.399
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC477591

Natural Product ID:	NPC477591
*Common Name:**	Nostocarboline hydroiodide
IUPAC Name:	6-chloro-2-methyl-9H-pyrido[3,4-b]indol-2-ium;iodide
Synonyms:	Nostacarboline Iodide; Nostocarboline; Nostocarboline Hydroiodide
Standard InCHIKey:	YSZAXPOWTBYIJG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H9ClN2.HI/c1-15-5-4-9-10-6-8(13)2-3-11(10)14-12(9)7-15;/h2-7H,1H3;1H
SMILES:	C[N+]1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl.[I-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11515734
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO33643	0stoc 78-12A	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16378379]

☑ 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	12
Others	7

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Organism	13
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	120900	nM	PMID[18606541]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	120900	nM	PMID[20133138]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	19400	nM	PMID[16378379]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	13200	nM	PMID[16378379]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	87100	nM	PMID[18606541]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	34300	nM	PMID[18606541]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	70500	nM	PMID[18606541]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	194	nM	PMID[18606541]
NPT2	Others	Unspecified		Ratio IC50	=	622	n.a.	PMID[18606541]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	194	nM	PMID[20133138]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	34300	nM	PMID[20133138]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	70500	nM	PMID[20133138]
NPT2	Others	Unspecified		Ratio IC50	=	622	n.a.	PMID[20133138]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	87100	nM	PMID[20133138]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC99	>	29	nM	PMID[20133138]
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC99	=	290	nM	PMID[20133138]
NPT1382	Organism	Corynebacterium glutamicum	Corynebacterium glutamicum	MIC99	>	29	nM	PMID[20133138]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	49.6	%	PMID[20133138]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Survival	=	7.3	day	PMID[20133138]

☑ 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 NPC477591 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	2482
0.1-0.2	14854
0.2-0.3	17039
0.3-0.4	3926
0.4-0.5	2175
0.5-0.6	1495
0.6-0.7	552
0.7-0.8	162
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8562	High Similarity	NPC470111
0.8562	High Similarity	NPC179787
0.8562	High Similarity	NPC201380
0.8506	High Similarity	NPC321911
0.8497	Intermediate Similarity	NPC63545
0.8442	Intermediate Similarity	NPC469811
0.8344	Intermediate Similarity	NPC315348
0.8344	Intermediate Similarity	NPC32002
0.8333	Intermediate Similarity	NPC40070
0.8323	Intermediate Similarity	NPC314919
0.825	Intermediate Similarity	NPC293487
0.8228	Intermediate Similarity	NPC325903
0.821	Intermediate Similarity	NPC478182
0.8187	Intermediate Similarity	NPC236711
0.8098	Intermediate Similarity	NPC478184
0.8092	Intermediate Similarity	NPC251722
0.8092	Intermediate Similarity	NPC314102
0.8092	Intermediate Similarity	NPC150259
0.8057	Intermediate Similarity	NPC314058
0.8057	Intermediate Similarity	NPC316018
0.8037	Intermediate Similarity	NPC478185
0.8012	Intermediate Similarity	NPC476464
0.8012	Intermediate Similarity	NPC91895
0.8	Intermediate Similarity	NPC478183
0.8	Intermediate Similarity	NPC56233
0.7975	Intermediate Similarity	NPC122141
0.7975	Intermediate Similarity	NPC470204
0.7955	Intermediate Similarity	NPC315617
0.7955	Intermediate Similarity	NPC316359
0.7945	Intermediate Similarity	NPC46358
0.7935	Intermediate Similarity	NPC115611
0.7927	Intermediate Similarity	NPC470203
0.7927	Intermediate Similarity	NPC225018
0.7904	Intermediate Similarity	NPC32534
0.7879	Intermediate Similarity	NPC317105
0.7871	Intermediate Similarity	NPC73767
0.7871	Intermediate Similarity	NPC110126
0.7857	Intermediate Similarity	NPC82331
0.7857	Intermediate Similarity	NPC84911
0.7843	Intermediate Similarity	NPC198988
0.784	Intermediate Similarity	NPC476219
0.784	Intermediate Similarity	NPC476297
0.7834	Intermediate Similarity	NPC20144
0.7831	Intermediate Similarity	NPC274229
0.7792	Intermediate Similarity	NPC96102
0.7792	Intermediate Similarity	NPC29886
0.7792	Intermediate Similarity	NPC261195
0.7771	Intermediate Similarity	NPC476454
0.7742	Intermediate Similarity	NPC105127
0.7733	Intermediate Similarity	NPC12649
0.7719	Intermediate Similarity	NPC280852
0.7716	Intermediate Similarity	NPC470233
0.7707	Intermediate Similarity	NPC469779
0.7707	Intermediate Similarity	NPC469768
0.7707	Intermediate Similarity	NPC469783
0.7707	Intermediate Similarity	NPC469784
0.7707	Intermediate Similarity	NPC469780
0.7707	Intermediate Similarity	NPC469761
0.7707	Intermediate Similarity	NPC469767
0.7701	Intermediate Similarity	NPC83381
0.7692	Intermediate Similarity	NPC169433
0.7692	Intermediate Similarity	NPC97343
0.7688	Intermediate Similarity	NPC288838
0.7688	Intermediate Similarity	NPC478186
0.7677	Intermediate Similarity	NPC325252
0.7661	Intermediate Similarity	NPC317054
0.7658	Intermediate Similarity	NPC469766
0.7654	Intermediate Similarity	NPC53947
0.7643	Intermediate Similarity	NPC104483
0.7616	Intermediate Similarity	NPC474958
0.761	Intermediate Similarity	NPC190296
0.7603	Intermediate Similarity	NPC91958
0.7595	Intermediate Similarity	NPC279081
0.7586	Intermediate Similarity	NPC24864
0.7568	Intermediate Similarity	NPC48564
0.7568	Intermediate Similarity	NPC265605
0.7568	Intermediate Similarity	NPC182570
0.7558	Intermediate Similarity	NPC471579
0.7545	Intermediate Similarity	NPC44773
0.7545	Intermediate Similarity	NPC215584
0.7532	Intermediate Similarity	NPC88097
0.7532	Intermediate Similarity	NPC82295
0.753	Intermediate Similarity	NPC129721
0.7516	Intermediate Similarity	NPC285731
0.7516	Intermediate Similarity	NPC314372
0.7516	Intermediate Similarity	NPC86288
0.7485	Intermediate Similarity	NPC56765
0.7485	Intermediate Similarity	NPC116961
0.7484	Intermediate Similarity	NPC230002
0.7484	Intermediate Similarity	NPC284635
0.7469	Intermediate Similarity	NPC143872
0.7466	Intermediate Similarity	NPC148140
0.7443	Intermediate Similarity	NPC191415
0.7423	Intermediate Similarity	NPC471957
0.7415	Intermediate Similarity	NPC81561
0.7407	Intermediate Similarity	NPC470440
0.7407	Intermediate Similarity	NPC159856
0.7375	Intermediate Similarity	NPC2949
0.7375	Intermediate Similarity	NPC59084
0.7365	Intermediate Similarity	NPC54102
0.7365	Intermediate Similarity	NPC162689
0.7365	Intermediate Similarity	NPC143603
0.7365	Intermediate Similarity	NPC51054
0.7365	Intermediate Similarity	NPC115049
0.736	Intermediate Similarity	NPC284678
0.7355	Intermediate Similarity	NPC282398
0.7355	Intermediate Similarity	NPC22079
0.7353	Intermediate Similarity	NPC90723
0.7349	Intermediate Similarity	NPC200214
0.7345	Intermediate Similarity	NPC307191
0.7333	Intermediate Similarity	NPC24678
0.7333	Intermediate Similarity	NPC105818
0.7329	Intermediate Similarity	NPC63157
0.7329	Intermediate Similarity	NPC473868
0.7321	Intermediate Similarity	NPC216643
0.7312	Intermediate Similarity	NPC316811
0.7305	Intermediate Similarity	NPC34844
0.7303	Intermediate Similarity	NPC476322
0.7303	Intermediate Similarity	NPC102755
0.7303	Intermediate Similarity	NPC48938
0.7297	Intermediate Similarity	NPC297486
0.7297	Intermediate Similarity	NPC240136
0.7297	Intermediate Similarity	NPC471402
0.7289	Intermediate Similarity	NPC470823
0.7278	Intermediate Similarity	NPC92796
0.7278	Intermediate Similarity	NPC135141
0.7278	Intermediate Similarity	NPC206819
0.7278	Intermediate Similarity	NPC318065
0.7267	Intermediate Similarity	NPC215519
0.7263	Intermediate Similarity	NPC108011
0.7257	Intermediate Similarity	NPC297034
0.7253	Intermediate Similarity	NPC231536
0.7246	Intermediate Similarity	NPC73952
0.7246	Intermediate Similarity	NPC469760
0.7246	Intermediate Similarity	NPC469786
0.7246	Intermediate Similarity	NPC469765
0.7246	Intermediate Similarity	NPC259644
0.7246	Intermediate Similarity	NPC141926
0.7246	Intermediate Similarity	NPC25008
0.7246	Intermediate Similarity	NPC469763
0.7246	Intermediate Similarity	NPC138842
0.7244	Intermediate Similarity	NPC69914
0.7233	Intermediate Similarity	NPC218268
0.7228	Intermediate Similarity	NPC198673
0.7219	Intermediate Similarity	NPC286427
0.7208	Intermediate Similarity	NPC250361
0.7207	Intermediate Similarity	NPC471609
0.7202	Intermediate Similarity	NPC80597
0.7202	Intermediate Similarity	NPC75540
0.7202	Intermediate Similarity	NPC211572
0.7202	Intermediate Similarity	NPC70922
0.7202	Intermediate Similarity	NPC212376
0.7197	Intermediate Similarity	NPC256893
0.7195	Intermediate Similarity	NPC204141
0.719	Intermediate Similarity	NPC122718
0.719	Intermediate Similarity	NPC27740
0.7188	Intermediate Similarity	NPC471312
0.7186	Intermediate Similarity	NPC216713
0.7182	Intermediate Similarity	NPC62749
0.7179	Intermediate Similarity	NPC476131
0.7179	Intermediate Similarity	NPC473587
0.7176	Intermediate Similarity	NPC41257
0.7143	Intermediate Similarity	NPC281094
0.7135	Intermediate Similarity	NPC81229
0.7135	Intermediate Similarity	NPC255229
0.7135	Intermediate Similarity	NPC229173
0.7134	Intermediate Similarity	NPC475428
0.7115	Intermediate Similarity	NPC473762
0.7114	Intermediate Similarity	NPC476566
0.711	Intermediate Similarity	NPC195507
0.711	Intermediate Similarity	NPC2165
0.7108	Intermediate Similarity	NPC21605
0.7093	Intermediate Similarity	NPC282231
0.7091	Intermediate Similarity	NPC469525
0.7089	Intermediate Similarity	NPC475450
0.7089	Intermediate Similarity	NPC179365
0.7076	Intermediate Similarity	NPC221786
0.7076	Intermediate Similarity	NPC475990
0.7076	Intermediate Similarity	NPC474880
0.7074	Intermediate Similarity	NPC168911
0.7074	Intermediate Similarity	NPC239954
0.7074	Intermediate Similarity	NPC212213
0.7062	Intermediate Similarity	NPC469938
0.7059	Intermediate Similarity	NPC469785
0.7059	Intermediate Similarity	NPC41174
0.7059	Intermediate Similarity	NPC329825
0.7055	Intermediate Similarity	NPC27802
0.7037	Intermediate Similarity	NPC81535
0.7035	Intermediate Similarity	NPC279918
0.7032	Intermediate Similarity	NPC146373
0.7032	Intermediate Similarity	NPC245244
0.7032	Intermediate Similarity	NPC166424
0.7024	Intermediate Similarity	NPC33421
0.7018	Intermediate Similarity	NPC469762
0.7013	Intermediate Similarity	NPC290094
0.6994	Remote Similarity	NPC194881
0.6989	Remote Similarity	NPC194411
0.6989	Remote Similarity	NPC324149
0.6984	Remote Similarity	NPC474916
0.6981	Remote Similarity	NPC101165

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 NPC477591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	632
0.1-0.2	1002
0.2-0.3	1118
0.3-0.4	2348
0.4-0.5	2138
0.5-0.6	1435
0.6-0.7	403
0.7-0.8	71
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8393	Intermediate Similarity	NPD5892	Approved
0.8387	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2075	Approved
0.8344	Intermediate Similarity	NPD2072	Approved
0.8344	Intermediate Similarity	NPD2074	Approved
0.8344	Intermediate Similarity	NPD2073	Approved
0.8205	Intermediate Similarity	NPD4547	Phase 3
0.8198	Intermediate Similarity	NPD2729	Approved
0.8198	Intermediate Similarity	NPD2728	Approved
0.8198	Intermediate Similarity	NPD2730	Approved
0.8176	Intermediate Similarity	NPD715	Phase 3
0.811	Intermediate Similarity	NPD1248	Discontinued
0.8075	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6497	Approved
0.8063	Intermediate Similarity	NPD2165	Phase 1
0.8013	Intermediate Similarity	NPD3385	Approved
0.8012	Intermediate Similarity	NPD3113	Approved
0.8012	Intermediate Similarity	NPD3115	Approved
0.8012	Intermediate Similarity	NPD3114	Approved
0.8012	Intermediate Similarity	NPD3112	Approved
0.7987	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2006	Phase 2
0.7933	Intermediate Similarity	NPD3476	Approved
0.7933	Intermediate Similarity	NPD3475	Approved
0.7925	Intermediate Similarity	NPD2430	Phase 2
0.7898	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1722	Approved
0.7882	Intermediate Similarity	NPD2731	Phase 2
0.7871	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD2119	Approved
0.7852	Intermediate Similarity	NPD2118	Approved
0.7844	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7216	Approved
0.7811	Intermediate Similarity	NPD7217	Approved
0.7792	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3339	Approved
0.7778	Intermediate Similarity	NPD2837	Discontinued
0.7756	Intermediate Similarity	NPD786	Approved
0.7748	Intermediate Similarity	NPD3654	Approved
0.7711	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4028	Approved
0.7662	Intermediate Similarity	NPD4030	Approved
0.7662	Intermediate Similarity	NPD4029	Approved
0.7633	Intermediate Similarity	NPD2333	Discontinued
0.7628	Intermediate Similarity	NPD6554	Approved
0.7628	Intermediate Similarity	NPD45	Approved
0.7624	Intermediate Similarity	NPD3362	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD409	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3100	Discontinued
0.7578	Intermediate Similarity	NPD1683	Approved
0.7568	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD271	Approved
0.7568	Intermediate Similarity	NPD268	Approved
0.7557	Intermediate Similarity	NPD1860	Approved
0.7548	Intermediate Similarity	NPD3942	Approved
0.7548	Intermediate Similarity	NPD3944	Approved
0.7544	Intermediate Similarity	NPD3117	Approved
0.7544	Intermediate Similarity	NPD3116	Approved
0.7531	Intermediate Similarity	NPD1661	Suspended
0.7529	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2771	Approved
0.75	Intermediate Similarity	NPD5315	Discontinued
0.75	Intermediate Similarity	NPD991	Phase 2
0.75	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4973	Approved
0.7485	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6217	Discontinued
0.7471	Intermediate Similarity	NPD7111	Discontinued
0.7456	Intermediate Similarity	NPD3323	Discontinued
0.7443	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2110	Approved
0.7417	Intermediate Similarity	NPD1937	Approved
0.7416	Intermediate Similarity	NPD1227	Phase 2
0.7414	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD976	Approved
0.741	Intermediate Similarity	NPD975	Approved
0.741	Intermediate Similarity	NPD977	Approved
0.7399	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7164	Discontinued
0.7394	Intermediate Similarity	NPD5012	Phase 2
0.7386	Intermediate Similarity	NPD3310	Approved
0.7381	Intermediate Similarity	NPD5418	Discontinued
0.7371	Intermediate Similarity	NPD2315	Approved
0.7365	Intermediate Similarity	NPD2580	Discontinued
0.736	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD6133	Discontinued
0.7342	Intermediate Similarity	NPD1255	Approved
0.7342	Intermediate Similarity	NPD1254	Approved
0.7342	Intermediate Similarity	NPD1253	Approved
0.7342	Intermediate Similarity	NPD1256	Approved
0.7333	Intermediate Similarity	NPD2172	Phase 1
0.733	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD9583	Approved
0.7318	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2069	Approved
0.7312	Intermediate Similarity	NPD2071	Approved
0.7312	Intermediate Similarity	NPD2070	Approved
0.7312	Intermediate Similarity	NPD2068	Approved
0.7302	Intermediate Similarity	NPD4446	Approved
0.7294	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4047	Discontinued
0.7278	Intermediate Similarity	NPD4902	Discontinued
0.7267	Intermediate Similarity	NPD3361	Phase 1
0.7267	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD165	Phase 2
0.7263	Intermediate Similarity	NPD4957	Phase 2
0.7256	Intermediate Similarity	NPD7469	Discontinued
0.7247	Intermediate Similarity	NPD2301	Approved
0.7243	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7394	Phase 2
0.7225	Intermediate Similarity	NPD2641	Approved
0.7225	Intermediate Similarity	NPD2640	Approved
0.7222	Intermediate Similarity	NPD3771	Phase 3
0.7219	Intermediate Similarity	NPD4326	Phase 2
0.7216	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2774	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1313	Approved
0.7207	Intermediate Similarity	NPD2111	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD803	Phase 1
0.7196	Intermediate Similarity	NPD2807	Discontinued
0.7193	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9357	Approved
0.7175	Intermediate Similarity	NPD4181	Approved
0.7171	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4848	Phase 1
0.7151	Intermediate Similarity	NPD1895	Discontinued
0.7143	Intermediate Similarity	NPD3609	Approved
0.7143	Intermediate Similarity	NPD3610	Approved
0.7135	Intermediate Similarity	NPD1403	Approved
0.7135	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1404	Approved
0.7134	Intermediate Similarity	NPD5254	Discontinued
0.7126	Intermediate Similarity	NPD4639	Approved
0.7126	Intermediate Similarity	NPD4638	Approved
0.7126	Intermediate Similarity	NPD4640	Approved
0.7119	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2720	Phase 1
0.711	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9598	Discontinued
0.7102	Intermediate Similarity	NPD2076	Approved
0.7102	Intermediate Similarity	NPD2077	Approved
0.7099	Intermediate Similarity	NPD174	Discontinued
0.7095	Intermediate Similarity	NPD3927	Phase 2
0.7088	Intermediate Similarity	NPD6721	Phase 1
0.7088	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1257	Approved
0.7074	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD2818	Discontinued
0.7062	Intermediate Similarity	NPD5065	Approved
0.7062	Intermediate Similarity	NPD4128	Approved
0.7056	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1993	Approved
0.7044	Intermediate Similarity	NPD1994	Approved
0.7044	Intermediate Similarity	NPD1995	Approved
0.7041	Intermediate Similarity	NPD4853	Approved
0.7039	Intermediate Similarity	NPD1893	Phase 2
0.7039	Intermediate Similarity	NPD1892	Phase 2
0.7031	Intermediate Similarity	NPD6714	Phase 3
0.703	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2373	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4703	Approved
0.7006	Intermediate Similarity	NPD4702	Approved
0.7005	Intermediate Similarity	NPD6787	Phase 2
0.6994	Remote Similarity	NPD1016	Phase 2
0.6994	Remote Similarity	NPD1015	Phase 2
0.6989	Remote Similarity	NPD3431	Approved
0.6989	Remote Similarity	NPD3430	Approved
0.6989	Remote Similarity	NPD5436	Phase 1
0.6983	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2639	Approved
0.6971	Remote Similarity	NPD2642	Approved
0.697	Remote Similarity	NPD2318	Discontinued
0.6966	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1183	Approved
0.6962	Remote Similarity	NPD947	Approved
0.6959	Remote Similarity	NPD2150	Discontinued
0.6957	Remote Similarity	NPD2142	Approved
0.6957	Remote Similarity	NPD2141	Approved
0.6957	Remote Similarity	NPD1883	Approved
0.6957	Remote Similarity	NPD2140	Approved
0.6954	Remote Similarity	NPD2738	Approved
0.6952	Remote Similarity	NPD3485	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