NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	317.05
Volume:	278.782
LogP:	3.492
LogD:	3.174
LogS:	-3.347
# Rotatable Bonds:	3
TPSA:	31.92
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	2.493
Fsp3:	0.267
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:	-4.62
MDCK Permeability:	1.3557994861912448e-05
Pgp-inhibitor:	0.118
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	82.27483367919922%
Volume Distribution (VD):	2.664
Pgp-substrate:	27.135116577148438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.432
CYP2D6-inhibitor:	0.858
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	4.096
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.914
Human Hepatotoxicity (H-HT):	0.658
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.848
Carcinogencity:	0.176
Eye Corrosion:	0.009
Eye Irritation:	0.039
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC82331

Natural Product ID:	NPC82331
*Common Name:**	Plakortamine A
IUPAC Name:	2-(7-bromo-9H-pyrido[3,4-b]indol-1-yl)-N,N-dimethylethanamine
Synonyms:
Standard InCHIKey:	IDDFVLLJLZRGBJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16BrN3/c1-19(2)8-6-13-15-12(5-7-17-13)11-4-3-10(16)9-14(11)18-15/h3-5,7,9,18H,6,8H2,1-2H3
SMILES:	CN(CCc1nccc2c1[nH]c1c2ccc(c1)Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483824
PubChem CID:	5324375
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	=	3200.0	nM	PMID[549144]

☑ 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 NPC82331 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	1197
0.1-0.2	14998
0.2-0.3	17884
0.3-0.4	3899
0.4-0.5	1889
0.5-0.6	1534
0.6-0.7	900
0.7-0.8	325
0.8-0.85	48
0.85-0.9	16
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC274229
0.9684	High Similarity	NPC474958
0.9207	High Similarity	NPC307191
0.9167	High Similarity	NPC231536
0.9097	High Similarity	NPC141926
0.9068	High Similarity	NPC97343
0.8961	High Similarity	NPC201380
0.8961	High Similarity	NPC179787
0.8903	High Similarity	NPC321911
0.8896	High Similarity	NPC63545
0.8841	High Similarity	NPC477611
0.8839	High Similarity	NPC469811
0.8757	High Similarity	NPC108011
0.8704	High Similarity	NPC149265
0.8679	High Similarity	NPC34844
0.865	High Similarity	NPC17751
0.8616	High Similarity	NPC325903
0.8571	High Similarity	NPC236711
0.8544	High Similarity	NPC2272
0.8476	Intermediate Similarity	NPC247987
0.8466	Intermediate Similarity	NPC470204
0.8452	Intermediate Similarity	NPC115611
0.8436	Intermediate Similarity	NPC237414
0.8415	Intermediate Similarity	NPC470203
0.8387	Intermediate Similarity	NPC110126
0.8387	Intermediate Similarity	NPC73767
0.8364	Intermediate Similarity	NPC317105
0.8354	Intermediate Similarity	NPC122141
0.8302	Intermediate Similarity	NPC316069
0.8297	Intermediate Similarity	NPC473761
0.8269	Intermediate Similarity	NPC316811
0.8258	Intermediate Similarity	NPC84911
0.8258	Intermediate Similarity	NPC105127
0.825	Intermediate Similarity	NPC470111
0.8247	Intermediate Similarity	NPC198988
0.8235	Intermediate Similarity	NPC280297
0.8217	Intermediate Similarity	NPC469768
0.8217	Intermediate Similarity	NPC469779
0.8217	Intermediate Similarity	NPC469783
0.8217	Intermediate Similarity	NPC469784
0.8217	Intermediate Similarity	NPC469761
0.8217	Intermediate Similarity	NPC469767
0.8217	Intermediate Similarity	NPC469780
0.821	Intermediate Similarity	NPC470233
0.8204	Intermediate Similarity	NPC280864
0.8204	Intermediate Similarity	NPC2165
0.8194	Intermediate Similarity	NPC261195
0.8194	Intermediate Similarity	NPC96102
0.8194	Intermediate Similarity	NPC29886
0.8187	Intermediate Similarity	NPC280852
0.8165	Intermediate Similarity	NPC469766
0.8148	Intermediate Similarity	NPC53947
0.8092	Intermediate Similarity	NPC276540
0.8092	Intermediate Similarity	NPC233050
0.8077	Intermediate Similarity	NPC325252
0.8075	Intermediate Similarity	NPC288838
0.8038	Intermediate Similarity	NPC88097
0.8037	Intermediate Similarity	NPC40070
0.8012	Intermediate Similarity	NPC314372
0.8	Intermediate Similarity	NPC243381
0.8	Intermediate Similarity	NPC190296
0.8	Intermediate Similarity	NPC476219
0.8	Intermediate Similarity	NPC476297
0.8	Intermediate Similarity	NPC275292
0.7989	Intermediate Similarity	NPC205254
0.7989	Intermediate Similarity	NPC23420
0.7989	Intermediate Similarity	NPC106771
0.7989	Intermediate Similarity	NPC303820
0.7987	Intermediate Similarity	NPC284635
0.7987	Intermediate Similarity	NPC279081
0.7987	Intermediate Similarity	NPC59084
0.7964	Intermediate Similarity	NPC56765
0.7956	Intermediate Similarity	NPC474180
0.7956	Intermediate Similarity	NPC188821
0.7946	Intermediate Similarity	NPC52909
0.7946	Intermediate Similarity	NPC475935
0.7946	Intermediate Similarity	NPC94211
0.7937	Intermediate Similarity	NPC473868
0.7937	Intermediate Similarity	NPC63157
0.7935	Intermediate Similarity	NPC474318
0.7935	Intermediate Similarity	NPC153123
0.7935	Intermediate Similarity	NPC82295
0.7935	Intermediate Similarity	NPC268744
0.7935	Intermediate Similarity	NPC201266
0.7935	Intermediate Similarity	NPC220797
0.7935	Intermediate Similarity	NPC475914
0.7929	Intermediate Similarity	NPC478184
0.7917	Intermediate Similarity	NPC215584
0.7917	Intermediate Similarity	NPC44773
0.7892	Intermediate Similarity	NPC166209
0.7892	Intermediate Similarity	NPC269203
0.7892	Intermediate Similarity	NPC13456
0.7892	Intermediate Similarity	NPC77241
0.7875	Intermediate Similarity	NPC2949
0.7875	Intermediate Similarity	NPC230002
0.787	Intermediate Similarity	NPC225018
0.7857	Intermediate Similarity	NPC477591
0.7853	Intermediate Similarity	NPC143872
0.7836	Intermediate Similarity	NPC478183
0.7831	Intermediate Similarity	NPC200214
0.7824	Intermediate Similarity	NPC478182
0.7824	Intermediate Similarity	NPC90723
0.7818	Intermediate Similarity	NPC105818
0.7818	Intermediate Similarity	NPC24678
0.7805	Intermediate Similarity	NPC471957
0.7802	Intermediate Similarity	NPC473342
0.7802	Intermediate Similarity	NPC304187
0.7802	Intermediate Similarity	NPC477167
0.7802	Intermediate Similarity	NPC477166
0.7799	Intermediate Similarity	NPC314102
0.7799	Intermediate Similarity	NPC251722
0.7798	Intermediate Similarity	NPC216643
0.7797	Intermediate Similarity	NPC191415
0.7791	Intermediate Similarity	NPC470440
0.7791	Intermediate Similarity	NPC159856
0.7784	Intermediate Similarity	NPC474389
0.7778	Intermediate Similarity	NPC195507
0.7756	Intermediate Similarity	NPC22079
0.7751	Intermediate Similarity	NPC206819
0.7751	Intermediate Similarity	NPC293487
0.7751	Intermediate Similarity	NPC135141
0.7751	Intermediate Similarity	NPC92796
0.7751	Intermediate Similarity	NPC318065
0.7736	Intermediate Similarity	NPC218268
0.7725	Intermediate Similarity	NPC259644
0.7725	Intermediate Similarity	NPC469760
0.7725	Intermediate Similarity	NPC232798
0.7725	Intermediate Similarity	NPC469765
0.7725	Intermediate Similarity	NPC73952
0.7725	Intermediate Similarity	NPC470505
0.7725	Intermediate Similarity	NPC25008
0.7725	Intermediate Similarity	NPC469786
0.7725	Intermediate Similarity	NPC469763
0.7714	Intermediate Similarity	NPC471579
0.7709	Intermediate Similarity	NPC284678
0.7709	Intermediate Similarity	NPC110158
0.7697	Intermediate Similarity	NPC21605
0.7692	Intermediate Similarity	NPC286427
0.7688	Intermediate Similarity	NPC150259
0.7683	Intermediate Similarity	NPC204141
0.7679	Intermediate Similarity	NPC70922
0.7679	Intermediate Similarity	NPC80597
0.7679	Intermediate Similarity	NPC212376
0.7679	Intermediate Similarity	NPC211572
0.7679	Intermediate Similarity	NPC75540
0.767	Intermediate Similarity	NPC121903
0.7665	Intermediate Similarity	NPC470823
0.7661	Intermediate Similarity	NPC253687
0.7654	Intermediate Similarity	NPC48938
0.7654	Intermediate Similarity	NPC102755
0.7647	Intermediate Similarity	NPC41257
0.7613	Intermediate Similarity	NPC250361
0.7602	Intermediate Similarity	NPC229173
0.7595	Intermediate Similarity	NPC475450
0.758	Intermediate Similarity	NPC473587
0.7568	Intermediate Similarity	NPC88315
0.756	Intermediate Similarity	NPC216713
0.7558	Intermediate Similarity	NPC478185
0.7557	Intermediate Similarity	NPC64055
0.7553	Intermediate Similarity	NPC477004
0.7544	Intermediate Similarity	NPC474880
0.7544	Intermediate Similarity	NPC475990
0.7544	Intermediate Similarity	NPC221786
0.7543	Intermediate Similarity	NPC91895
0.7532	Intermediate Similarity	NPC475428
0.7532	Intermediate Similarity	NPC46358
0.7529	Intermediate Similarity	NPC56233
0.7529	Intermediate Similarity	NPC469785
0.7529	Intermediate Similarity	NPC109447
0.7527	Intermediate Similarity	NPC62749
0.7516	Intermediate Similarity	NPC473762
0.75	Intermediate Similarity	NPC33421
0.75	Intermediate Similarity	NPC476121
0.7485	Intermediate Similarity	NPC469762
0.7484	Intermediate Similarity	NPC179365
0.7468	Intermediate Similarity	NPC41174
0.7458	Intermediate Similarity	NPC288074
0.7457	Intermediate Similarity	NPC282231
0.7455	Intermediate Similarity	NPC20144
0.7449	Intermediate Similarity	NPC470702
0.7449	Intermediate Similarity	NPC473218
0.7443	Intermediate Similarity	NPC32534
0.7443	Intermediate Similarity	NPC194411
0.7438	Intermediate Similarity	NPC60006
0.7429	Intermediate Similarity	NPC474561
0.7429	Intermediate Similarity	NPC49954
0.7416	Intermediate Similarity	NPC317054
0.7414	Intermediate Similarity	NPC311276
0.7411	Intermediate Similarity	NPC470703
0.7407	Intermediate Similarity	NPC265576
0.7399	Intermediate Similarity	NPC279918
0.7389	Intermediate Similarity	NPC245348
0.7389	Intermediate Similarity	NPC11126
0.7386	Intermediate Similarity	NPC63751
0.7372	Intermediate Similarity	NPC27740
0.7362	Intermediate Similarity	NPC125746
0.7354	Intermediate Similarity	NPC262898
0.7348	Intermediate Similarity	NPC314919
0.7345	Intermediate Similarity	NPC474897
0.7341	Intermediate Similarity	NPC6436

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 NPC82331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	970
0.2-0.3	1100
0.3-0.4	2340
0.4-0.5	2063
0.5-0.6	1529
0.6-0.7	554
0.7-0.8	111
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8397	Intermediate Similarity	NPD1722	Approved
0.8385	Intermediate Similarity	NPD2837	Discontinued
0.8269	Intermediate Similarity	NPD2070	Approved
0.8269	Intermediate Similarity	NPD2069	Approved
0.8269	Intermediate Similarity	NPD786	Approved
0.8269	Intermediate Similarity	NPD2068	Approved
0.8269	Intermediate Similarity	NPD2071	Approved
0.8194	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD3100	Discontinued
0.8	Intermediate Similarity	NPD1993	Approved
0.8	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1994	Approved
0.8	Intermediate Similarity	NPD1995	Approved
0.7975	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3323	Discontinued
0.7914	Intermediate Similarity	NPD4547	Phase 3
0.787	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2172	Phase 1
0.7778	Intermediate Similarity	NPD2006	Phase 2
0.7764	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2430	Phase 2
0.7756	Intermediate Similarity	NPD715	Phase 3
0.7722	Intermediate Similarity	NPD3385	Approved
0.7688	Intermediate Similarity	NPD2641	Approved
0.7688	Intermediate Similarity	NPD2640	Approved
0.7643	Intermediate Similarity	NPD3475	Approved
0.7643	Intermediate Similarity	NPD3476	Approved
0.764	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1683	Approved
0.7627	Intermediate Similarity	NPD4181	Approved
0.7622	Intermediate Similarity	NPD5254	Discontinued
0.7614	Intermediate Similarity	NPD5065	Approved
0.7602	Intermediate Similarity	NPD1404	Approved
0.7602	Intermediate Similarity	NPD1403	Approved
0.76	Intermediate Similarity	NPD3609	Approved
0.76	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3610	Approved
0.7564	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2119	Approved
0.7564	Intermediate Similarity	NPD2118	Approved
0.7564	Intermediate Similarity	NPD991	Phase 2
0.7545	Intermediate Similarity	NPD1183	Approved
0.7515	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4128	Approved
0.75	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1895	Discontinued
0.7486	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD803	Phase 1
0.7473	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD976	Approved
0.7471	Intermediate Similarity	NPD975	Approved
0.7471	Intermediate Similarity	NPD977	Approved
0.7468	Intermediate Similarity	NPD3654	Approved
0.7455	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2642	Approved
0.7429	Intermediate Similarity	NPD2639	Approved
0.7391	Intermediate Similarity	NPD4030	Approved
0.7391	Intermediate Similarity	NPD4028	Approved
0.7391	Intermediate Similarity	NPD4029	Approved
0.7389	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4075	Phase 2
0.7371	Intermediate Similarity	NPD1313	Approved
0.7368	Intermediate Similarity	NPD2165	Phase 1
0.7356	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3115	Approved
0.7326	Intermediate Similarity	NPD3114	Approved
0.7326	Intermediate Similarity	NPD3112	Approved
0.7326	Intermediate Similarity	NPD3113	Approved
0.7326	Intermediate Similarity	NPD2580	Discontinued
0.7301	Intermediate Similarity	NPD1256	Approved
0.7301	Intermediate Similarity	NPD1254	Approved
0.7301	Intermediate Similarity	NPD1255	Approved
0.7301	Intermediate Similarity	NPD1253	Approved
0.7294	Intermediate Similarity	NPD4462	Approved
0.7294	Intermediate Similarity	NPD4463	Approved
0.729	Intermediate Similarity	NPD268	Approved
0.729	Intermediate Similarity	NPD271	Approved
0.729	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3942	Approved
0.7284	Intermediate Similarity	NPD3944	Approved
0.7278	Intermediate Similarity	NPD1661	Suspended
0.7273	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1262	Discovery
0.7256	Intermediate Similarity	NPD6554	Approved
0.7256	Intermediate Similarity	NPD45	Approved
0.7253	Intermediate Similarity	NPD6595	Phase 3
0.7249	Intermediate Similarity	NPD7618	Phase 3
0.7249	Intermediate Similarity	NPD7619	Phase 3
0.7247	Intermediate Similarity	NPD5436	Phase 1
0.7247	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD3505	Approved
0.7238	Intermediate Similarity	NPD3506	Approved
0.7232	Intermediate Similarity	NPD438	Approved
0.7232	Intermediate Similarity	NPD439	Approved
0.7225	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1707	Approved
0.7213	Intermediate Similarity	NPD1708	Approved
0.7204	Intermediate Similarity	NPD3961	Discontinued
0.7204	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4076	Approved
0.7198	Intermediate Similarity	NPD4079	Approved
0.7191	Intermediate Similarity	NPD2333	Discontinued
0.7182	Intermediate Similarity	NPD2367	Phase 2
0.7179	Intermediate Similarity	NPD9598	Discontinued
0.7174	Intermediate Similarity	NPD5106	Approved
0.7174	Intermediate Similarity	NPD5105	Approved
0.7174	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD9583	Approved
0.7159	Intermediate Similarity	NPD5315	Discontinued
0.7158	Intermediate Similarity	NPD5962	Phase 2
0.7151	Intermediate Similarity	NPD2793	Discontinued
0.7143	Intermediate Similarity	NPD5418	Discontinued
0.7143	Intermediate Similarity	NPD7111	Discontinued
0.7143	Intermediate Similarity	NPD2144	Approved
0.7135	Intermediate Similarity	NPD1248	Discontinued
0.7126	Intermediate Similarity	NPD2150	Discontinued
0.712	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7394	Phase 2
0.7112	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6828	Phase 2
0.7111	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2880	Discontinued
0.7081	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1333	Phase 3
0.7072	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2075	Approved
0.7066	Intermediate Similarity	NPD2073	Approved
0.7066	Intermediate Similarity	NPD2072	Approved
0.7066	Intermediate Similarity	NPD2074	Approved
0.7062	Intermediate Similarity	NPD1015	Phase 2
0.7062	Intermediate Similarity	NPD1016	Phase 2
0.7059	Intermediate Similarity	NPD6217	Discontinued
0.7056	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD9357	Approved
0.7043	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4957	Phase 2
0.7039	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD947	Approved
0.7032	Intermediate Similarity	NPD9392	Approved
0.7032	Intermediate Similarity	NPD9396	Approved
0.7027	Intermediate Similarity	NPD3038	Discontinued
0.7019	Intermediate Similarity	NPD1598	Discontinued
0.7018	Intermediate Similarity	NPD7469	Discontinued
0.7017	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5462	Discontinued
0.6995	Remote Similarity	NPD3348	Phase 2
0.6995	Remote Similarity	NPD749	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3015	Discontinued
0.6988	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4702	Approved
0.6977	Remote Similarity	NPD4703	Approved
0.697	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4902	Discontinued
0.6966	Remote Similarity	NPD6771	Discontinued
0.6964	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4615	Phase 2
0.6941	Remote Similarity	NPD4047	Discontinued
0.694	Remote Similarity	NPD482	Approved
0.6936	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2927	Phase 3
0.6931	Remote Similarity	NPD8431	Approved
0.6923	Remote Similarity	NPD3116	Approved
0.6923	Remote Similarity	NPD3117	Approved
0.6919	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD1227	Phase 2
0.691	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6664	Approved
0.6903	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.69	Remote Similarity	NPD2443	Approved
0.69	Remote Similarity	NPD2442	Approved
0.6897	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4326	Phase 2
0.6889	Remote Similarity	NPD509	Phase 3
0.6884	Remote Similarity	NPD2008	Discontinued
0.6882	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4922	Phase 2
0.6862	Remote Similarity	NPD6178	Phase 3
0.6862	Remote Similarity	NPD7564	Discontinued
0.6853	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD2748	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