NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	271.99
Volume:	230.557
LogP:	3.857
LogD:	3.524
LogS:	-5.049
# Rotatable Bonds:	1
TPSA:	28.68
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	2.678
Fsp3:	0.0
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:	-4.92
MDCK Permeability:	1.7587493857718073e-05
Pgp-inhibitor:	0.284
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.893
Plasma Protein Binding (PPB):	94.97147369384766%
Volume Distribution (VD):	1.56
Pgp-substrate:	4.241878509521484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.993
CYP1A2-substrate:	0.461
CYP2C19-inhibitor:	0.769
CYP2C19-substrate:	0.409
CYP2C9-inhibitor:	0.512
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.86
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	1.537
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.446
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.195
Rat Oral Acute Toxicity:	0.917
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.83
Carcinogencity:	0.721
Eye Corrosion:	0.229
Eye Irritation:	0.986
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC274229

Natural Product ID:	NPC274229
*Common Name:**	Plakortamine B
IUPAC Name:	7-bromo-1-ethenyl-9H-pyrido[3,4-b]indole
Synonyms:	Plakortamine B
Standard InCHIKey:	NGUUMPOEQGEUOE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H9BrN2/c1-2-11-13-10(5-6-15-11)9-4-3-8(14)7-12(9)16-13/h2-7,16H,1H2
SMILES:	C=Cc1c2c(ccn1)c1ccc(cc1[nH]2)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483823
PubChem CID:	10084660
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
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[12350142]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[15387674]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	620.0	nM	PMID[485506]

☑ 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 NPC274229 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	1467
0.1-0.2	15468
0.2-0.3	17488
0.3-0.4	3817
0.4-0.5	1780
0.5-0.6	1496
0.6-0.7	811
0.7-0.8	297
0.8-0.85	48
0.85-0.9	16
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC82331
0.9554	High Similarity	NPC474958
0.9317	High Similarity	NPC307191
0.9299	High Similarity	NPC97343
0.9211	High Similarity	NPC141926
0.9133	High Similarity	NPC63545
0.9073	High Similarity	NPC201380
0.9073	High Similarity	NPC469811
0.9073	High Similarity	NPC179787
0.9013	High Similarity	NPC321911
0.8929	High Similarity	NPC231536
0.8868	High Similarity	NPC17751
0.8855	High Similarity	NPC108011
0.8839	High Similarity	NPC325903
0.8827	High Similarity	NPC477611
0.8688	High Similarity	NPC149265
0.8671	High Similarity	NPC236711
0.8662	High Similarity	NPC34844
0.8571	High Similarity	NPC247987
0.8562	High Similarity	NPC122141
0.8562	High Similarity	NPC470204
0.8526	High Similarity	NPC2272
0.8523	High Similarity	NPC237414
0.8516	High Similarity	NPC316069
0.8509	High Similarity	NPC470203
0.8457	Intermediate Similarity	NPC317105
0.8434	Intermediate Similarity	NPC280297
0.8431	Intermediate Similarity	NPC115611
0.8411	Intermediate Similarity	NPC96102
0.8405	Intermediate Similarity	NPC280864
0.838	Intermediate Similarity	NPC473761
0.8355	Intermediate Similarity	NPC84911
0.8355	Intermediate Similarity	NPC105127
0.8289	Intermediate Similarity	NPC29886
0.8289	Intermediate Similarity	NPC261195
0.828	Intermediate Similarity	NPC288838
0.8247	Intermediate Similarity	NPC73767
0.8247	Intermediate Similarity	NPC110126
0.8228	Intermediate Similarity	NPC470111
0.8224	Intermediate Similarity	NPC198988
0.8194	Intermediate Similarity	NPC469784
0.8194	Intermediate Similarity	NPC469761
0.8194	Intermediate Similarity	NPC469780
0.8194	Intermediate Similarity	NPC469779
0.8194	Intermediate Similarity	NPC469767
0.8194	Intermediate Similarity	NPC469768
0.8194	Intermediate Similarity	NPC469783
0.8194	Intermediate Similarity	NPC279081
0.8176	Intermediate Similarity	NPC233050
0.8176	Intermediate Similarity	NPC276540
0.817	Intermediate Similarity	NPC325252
0.8146	Intermediate Similarity	NPC82295
0.8141	Intermediate Similarity	NPC469766
0.8129	Intermediate Similarity	NPC316811
0.8125	Intermediate Similarity	NPC53947
0.8089	Intermediate Similarity	NPC190296
0.8081	Intermediate Similarity	NPC275292
0.8081	Intermediate Similarity	NPC243381
0.8077	Intermediate Similarity	NPC230002
0.8077	Intermediate Similarity	NPC284635
0.8075	Intermediate Similarity	NPC470233
0.8061	Intermediate Similarity	NPC225018
0.8059	Intermediate Similarity	NPC280852
0.805	Intermediate Similarity	NPC143872
0.8013	Intermediate Similarity	NPC88097
0.8011	Intermediate Similarity	NPC220797
0.8011	Intermediate Similarity	NPC268744
0.8011	Intermediate Similarity	NPC153123
0.8011	Intermediate Similarity	NPC201266
0.8011	Intermediate Similarity	NPC474318
0.8011	Intermediate Similarity	NPC475914
0.8	Intermediate Similarity	NPC215584
0.8	Intermediate Similarity	NPC44773
0.7987	Intermediate Similarity	NPC159856
0.7987	Intermediate Similarity	NPC314372
0.7967	Intermediate Similarity	NPC23420
0.7967	Intermediate Similarity	NPC303820
0.7967	Intermediate Similarity	NPC13456
0.7967	Intermediate Similarity	NPC106771
0.7967	Intermediate Similarity	NPC166209
0.7967	Intermediate Similarity	NPC205254
0.7967	Intermediate Similarity	NPC77241
0.7967	Intermediate Similarity	NPC269203
0.7964	Intermediate Similarity	NPC2165
0.7933	Intermediate Similarity	NPC188821
0.7933	Intermediate Similarity	NPC474180
0.7923	Intermediate Similarity	NPC52909
0.7923	Intermediate Similarity	NPC475935
0.7923	Intermediate Similarity	NPC94211
0.7917	Intermediate Similarity	NPC478183
0.7914	Intermediate Similarity	NPC232798
0.7904	Intermediate Similarity	NPC478184
0.7892	Intermediate Similarity	NPC470505
0.7888	Intermediate Similarity	NPC471957
0.7886	Intermediate Similarity	NPC110158
0.7879	Intermediate Similarity	NPC216643
0.7877	Intermediate Similarity	NPC477167
0.7877	Intermediate Similarity	NPC473342
0.7877	Intermediate Similarity	NPC477166
0.7877	Intermediate Similarity	NPC304187
0.7874	Intermediate Similarity	NPC191415
0.7843	Intermediate Similarity	NPC22079
0.7831	Intermediate Similarity	NPC92796
0.7831	Intermediate Similarity	NPC135141
0.7831	Intermediate Similarity	NPC293487
0.7831	Intermediate Similarity	NPC56765
0.7831	Intermediate Similarity	NPC477591
0.7829	Intermediate Similarity	NPC102755
0.7829	Intermediate Similarity	NPC48938
0.7821	Intermediate Similarity	NPC218268
0.7815	Intermediate Similarity	NPC250361
0.7791	Intermediate Similarity	NPC40070
0.7791	Intermediate Similarity	NPC471579
0.7791	Intermediate Similarity	NPC105818
0.7791	Intermediate Similarity	NPC24678
0.7784	Intermediate Similarity	NPC284678
0.7764	Intermediate Similarity	NPC470440
0.7764	Intermediate Similarity	NPC204141
0.776	Intermediate Similarity	NPC474389
0.7758	Intermediate Similarity	NPC476297
0.7758	Intermediate Similarity	NPC476219
0.7744	Intermediate Similarity	NPC216713
0.7744	Intermediate Similarity	NPC470823
0.7738	Intermediate Similarity	NPC253687
0.7736	Intermediate Similarity	NPC59084
0.7736	Intermediate Similarity	NPC2949
0.7733	Intermediate Similarity	NPC46358
0.7712	Intermediate Similarity	NPC473762
0.7697	Intermediate Similarity	NPC469763
0.7697	Intermediate Similarity	NPC73952
0.7697	Intermediate Similarity	NPC259644
0.7697	Intermediate Similarity	NPC25008
0.7697	Intermediate Similarity	NPC469765
0.7697	Intermediate Similarity	NPC62749
0.7697	Intermediate Similarity	NPC200214
0.7697	Intermediate Similarity	NPC469760
0.7697	Intermediate Similarity	NPC469786
0.7692	Intermediate Similarity	NPC90723
0.7692	Intermediate Similarity	NPC478182
0.7688	Intermediate Similarity	NPC63157
0.7688	Intermediate Similarity	NPC473868
0.7665	Intermediate Similarity	NPC286427
0.7662	Intermediate Similarity	NPC473587
0.7658	Intermediate Similarity	NPC251722
0.7658	Intermediate Similarity	NPC314102
0.7651	Intermediate Similarity	NPC211572
0.7651	Intermediate Similarity	NPC212376
0.7651	Intermediate Similarity	NPC75540
0.7651	Intermediate Similarity	NPC80597
0.7651	Intermediate Similarity	NPC70922
0.7637	Intermediate Similarity	NPC88315
0.7633	Intermediate Similarity	NPC478185
0.7619	Intermediate Similarity	NPC41257
0.7619	Intermediate Similarity	NPC206819
0.7619	Intermediate Similarity	NPC318065
0.7613	Intermediate Similarity	NPC475428
0.7605	Intermediate Similarity	NPC469785
0.7602	Intermediate Similarity	NPC56233
0.7574	Intermediate Similarity	NPC279918
0.7564	Intermediate Similarity	NPC475450
0.7564	Intermediate Similarity	NPC179365
0.756	Intermediate Similarity	NPC469762
0.755	Intermediate Similarity	NPC41174
0.7547	Intermediate Similarity	NPC125746
0.7547	Intermediate Similarity	NPC150259
0.7544	Intermediate Similarity	NPC195507
0.7543	Intermediate Similarity	NPC121903
0.7529	Intermediate Similarity	NPC64055
0.7529	Intermediate Similarity	NPC282231
0.7527	Intermediate Similarity	NPC477004
0.7516	Intermediate Similarity	NPC473930
0.7514	Intermediate Similarity	NPC91895
0.7514	Intermediate Similarity	NPC32534
0.7513	Intermediate Similarity	NPC470702
0.7513	Intermediate Similarity	NPC473218
0.75	Intermediate Similarity	NPC109447
0.75	Intermediate Similarity	NPC169433
0.75	Intermediate Similarity	NPC282398
0.7486	Intermediate Similarity	NPC324149
0.7474	Intermediate Similarity	NPC476121
0.7474	Intermediate Similarity	NPC470703
0.7471	Intermediate Similarity	NPC131718
0.7471	Intermediate Similarity	NPC229173
0.7457	Intermediate Similarity	NPC63751
0.7455	Intermediate Similarity	NPC21605
0.7451	Intermediate Similarity	NPC27740
0.7446	Intermediate Similarity	NPC326422
0.7412	Intermediate Similarity	NPC474880
0.7412	Intermediate Similarity	NPC475990
0.7412	Intermediate Similarity	NPC230869
0.7412	Intermediate Similarity	NPC221786
0.74	Intermediate Similarity	NPC91958
0.7399	Intermediate Similarity	NPC54988
0.7399	Intermediate Similarity	NPC474561
0.7399	Intermediate Similarity	NPC49954
0.7386	Intermediate Similarity	NPC317054
0.7384	Intermediate Similarity	NPC311276
0.7374	Intermediate Similarity	NPC292958
0.7365	Intermediate Similarity	NPC33421
0.7333	Intermediate Similarity	NPC86288

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 NPC274229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	548
0.1-0.2	1025
0.2-0.3	1186
0.3-0.4	2414
0.4-0.5	2042
0.5-0.6	1369
0.6-0.7	490
0.7-0.8	69
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8497	Intermediate Similarity	NPD1722	Approved
0.8411	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD2837	Discontinued
0.8247	Intermediate Similarity	NPD786	Approved
0.8129	Intermediate Similarity	NPD2069	Approved
0.8129	Intermediate Similarity	NPD2070	Approved
0.8129	Intermediate Similarity	NPD2071	Approved
0.8129	Intermediate Similarity	NPD2068	Approved
0.8063	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3100	Discontinued
0.7857	Intermediate Similarity	NPD1993	Approved
0.7857	Intermediate Similarity	NPD1994	Approved
0.7857	Intermediate Similarity	NPD1995	Approved
0.7843	Intermediate Similarity	NPD715	Phase 3
0.7798	Intermediate Similarity	NPD3323	Discontinued
0.7791	Intermediate Similarity	NPD2172	Phase 1
0.775	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1183	Approved
0.767	Intermediate Similarity	NPD1895	Discontinued
0.7669	Intermediate Similarity	NPD4547	Phase 3
0.7651	Intermediate Similarity	NPD975	Approved
0.7651	Intermediate Similarity	NPD976	Approved
0.7651	Intermediate Similarity	NPD977	Approved
0.7647	Intermediate Similarity	NPD991	Phase 2
0.7647	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2006	Phase 2
0.7625	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2430	Phase 2
0.7614	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD2641	Approved
0.7558	Intermediate Similarity	NPD2640	Approved
0.7531	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4181	Approved
0.75	Intermediate Similarity	NPD3476	Approved
0.75	Intermediate Similarity	NPD3475	Approved
0.75	Intermediate Similarity	NPD1683	Approved
0.7486	Intermediate Similarity	NPD5065	Approved
0.7485	Intermediate Similarity	NPD5254	Discontinued
0.7472	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1403	Approved
0.7471	Intermediate Similarity	NPD3610	Approved
0.7471	Intermediate Similarity	NPD3609	Approved
0.7471	Intermediate Similarity	NPD1404	Approved
0.7468	Intermediate Similarity	NPD3385	Approved
0.7457	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1262	Discovery
0.7419	Intermediate Similarity	NPD2118	Approved
0.7419	Intermediate Similarity	NPD2119	Approved
0.7386	Intermediate Similarity	NPD4128	Approved
0.736	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1661	Suspended
0.7342	Intermediate Similarity	NPD803	Phase 1
0.7299	Intermediate Similarity	NPD2642	Approved
0.7299	Intermediate Similarity	NPD438	Approved
0.7299	Intermediate Similarity	NPD2639	Approved
0.7299	Intermediate Similarity	NPD439	Approved
0.7263	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4463	Approved
0.7262	Intermediate Similarity	NPD4462	Approved
0.7257	Intermediate Similarity	NPD2333	Discontinued
0.7257	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4029	Approved
0.725	Intermediate Similarity	NPD4030	Approved
0.725	Intermediate Similarity	NPD4028	Approved
0.7244	Intermediate Similarity	NPD9583	Approved
0.7225	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6595	Phase 3
0.7216	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3654	Approved
0.7209	Intermediate Similarity	NPD5418	Discontinued
0.7207	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1248	Discontinued
0.7193	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2580	Discontinued
0.7174	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1255	Approved
0.716	Intermediate Similarity	NPD1256	Approved
0.716	Intermediate Similarity	NPD1254	Approved
0.716	Intermediate Similarity	NPD1253	Approved
0.7159	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4075	Phase 2
0.7151	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD271	Approved
0.7143	Intermediate Similarity	NPD9598	Discontinued
0.7143	Intermediate Similarity	NPD3942	Approved
0.7143	Intermediate Similarity	NPD268	Approved
0.7143	Intermediate Similarity	NPD3944	Approved
0.7143	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1313	Approved
0.7135	Intermediate Similarity	NPD2165	Phase 1
0.7134	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5436	Phase 1
0.7117	Intermediate Similarity	NPD45	Approved
0.7117	Intermediate Similarity	NPD6554	Approved
0.7115	Intermediate Similarity	NPD9357	Approved
0.7111	Intermediate Similarity	NPD3505	Approved
0.7111	Intermediate Similarity	NPD3506	Approved
0.7107	Intermediate Similarity	NPD947	Approved
0.7095	Intermediate Similarity	NPD482	Approved
0.7093	Intermediate Similarity	NPD3115	Approved
0.7093	Intermediate Similarity	NPD3113	Approved
0.7093	Intermediate Similarity	NPD3114	Approved
0.7093	Intermediate Similarity	NPD3112	Approved
0.709	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1598	Discontinued
0.7088	Intermediate Similarity	NPD1707	Approved
0.7088	Intermediate Similarity	NPD1708	Approved
0.7083	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4076	Approved
0.7072	Intermediate Similarity	NPD4079	Approved
0.7065	Intermediate Similarity	NPD1227	Phase 2
0.7056	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2367	Phase 2
0.7049	Intermediate Similarity	NPD5105	Approved
0.7049	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5106	Approved
0.7037	Intermediate Similarity	NPD7619	Phase 3
0.7037	Intermediate Similarity	NPD7618	Phase 3
0.7029	Intermediate Similarity	NPD5315	Discontinued
0.7027	Intermediate Similarity	NPD2793	Discontinued
0.7027	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7111	Discontinued
0.7017	Intermediate Similarity	NPD2144	Approved
0.7006	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9396	Approved
0.6993	Remote Similarity	NPD9392	Approved
0.6989	Remote Similarity	NPD3961	Discontinued
0.6989	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2880	Discontinued
0.6961	Remote Similarity	NPD3348	Phase 2
0.6959	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2720	Phase 1
0.6944	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5962	Phase 2
0.694	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6217	Discontinued
0.6932	Remote Similarity	NPD1015	Phase 2
0.6932	Remote Similarity	NPD1016	Phase 2
0.6928	Remote Similarity	NPD2072	Approved
0.6928	Remote Similarity	NPD2075	Approved
0.6928	Remote Similarity	NPD2074	Approved
0.6928	Remote Similarity	NPD2073	Approved
0.6927	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6178	Phase 3
0.6919	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD3038	Discontinued
0.6898	Remote Similarity	NPD7394	Phase 2
0.6898	Remote Similarity	NPD8431	Approved
0.6897	Remote Similarity	NPD2927	Phase 3
0.6897	Remote Similarity	NPD2150	Discontinued
0.6895	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6828	Phase 2
0.6882	Remote Similarity	NPD7469	Discontinued
0.6879	Remote Similarity	NPD1561	Phase 2
0.6879	Remote Similarity	NPD3339	Approved
0.6878	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3015	Discontinued
0.6865	Remote Similarity	NPD2094	Phase 2
0.6865	Remote Similarity	NPD2092	Phase 2
0.6865	Remote Similarity	NPD2095	Phase 2
0.6854	Remote Similarity	NPD1333	Phase 3
0.6854	Remote Similarity	NPD509	Phase 3
0.6848	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4902	Discontinued
0.6845	Remote Similarity	NPD706	Phase 1
0.6842	Remote Similarity	NPD4702	Approved
0.6842	Remote Similarity	NPD4703	Approved
0.6828	Remote Similarity	NPD2096	Phase 2
0.6828	Remote Similarity	NPD2091	Phase 2
0.6828	Remote Similarity	NPD4957	Phase 2
0.6821	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1251	Discontinued
0.6805	Remote Similarity	NPD4047	Discontinued
0.6796	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD1327	Discontinued
0.6789	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4880	Discontinued
0.6788	Remote Similarity	NPD5462	Discontinued
0.6782	Remote Similarity	NPD4341	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