NPASS Compound

Structure

NPC247987 OpenBabel07101719242D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.1646 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7524 0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9334 2.3225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.5267 3.2361 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9280 2.2180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.8271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3457 1.5135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 6 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 20 1 0 0 0 0 7 19 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 13 2 0 0 0 0 11 14 2 0 0 0 0 12 2 1 6 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	349.09
Volume:	303.412
LogP:	0.571
LogD:	1.133
LogS:	-2.827
# Rotatable Bonds:	5
TPSA:	89.72
# H-Bond Aceptor:	5
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	3.215
Fsp3:	0.4
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:	-5.682
MDCK Permeability:	9.000003956316505e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.307

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.138
Plasma Protein Binding (PPB):	66.28170776367188%
Volume Distribution (VD):	2.069
Pgp-substrate:	55.097843170166016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.646
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.61
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	4.11
Half-life (T1/2):	0.553

ADMET: Toxicity

hERG Blockers:	0.7
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.288
AMES Toxicity:	0.174
Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.342
Carcinogencity:	0.118
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC247987

Natural Product ID:	NPC247987
*Common Name:**	(+)-7-Bromotrypargine
IUPAC Name:	2-[3-[(1R)-7-bromo-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]propyl]guanidine
Synonyms:	(+)-7-Bromotrypargine
Standard InCHIKey:	FDYSADFFUCUKDQ-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C15H20BrN5/c16-9-3-4-10-11-5-7-19-12(2-1-6-20-15(17)18)14(11)21-13(10)8-9/h3-4,8,12,19,21H,1-2,5-7H2,(H4,17,18,20)/t12-/m1/s1
SMILES:	NC(=N)NCCC[C@H]1NCCc2c1[nH]c1c2ccc(c1)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822000
PubChem CID:	45140078
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
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26670413]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	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	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5400.0	nM	PMID[535875]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3500.0	nM	PMID[535875]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3500.0	nM	PMID[535876]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5400.0	nM	PMID[535876]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5400.0	nM	PMID[535877]

☑ 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 NPC247987 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	1626
0.1-0.2	15171
0.2-0.3	17354
0.3-0.4	3729
0.4-0.5	2347
0.5-0.6	1544
0.6-0.7	684
0.7-0.8	213
0.8-0.85	24
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9136	High Similarity	NPC307191
0.9128	High Similarity	NPC204141
0.8924	High Similarity	NPC17751
0.8824	High Similarity	NPC2272
0.8683	High Similarity	NPC108011
0.8654	High Similarity	NPC232798
0.8571	High Similarity	NPC274229
0.8545	High Similarity	NPC474958
0.8535	High Similarity	NPC141926
0.8485	Intermediate Similarity	NPC280297
0.8476	Intermediate Similarity	NPC82331
0.8467	Intermediate Similarity	NPC325252
0.8457	Intermediate Similarity	NPC280864
0.8385	Intermediate Similarity	NPC470204
0.8344	Intermediate Similarity	NPC2165
0.8333	Intermediate Similarity	NPC477166
0.8333	Intermediate Similarity	NPC470203
0.8333	Intermediate Similarity	NPC473342
0.8333	Intermediate Similarity	NPC304187
0.8333	Intermediate Similarity	NPC477167
0.8301	Intermediate Similarity	NPC88097
0.8289	Intermediate Similarity	NPC125746
0.8278	Intermediate Similarity	NPC198988
0.8224	Intermediate Similarity	NPC218268
0.8204	Intermediate Similarity	NPC477611
0.8182	Intermediate Similarity	NPC188821
0.8182	Intermediate Similarity	NPC474180
0.8101	Intermediate Similarity	NPC143872
0.8101	Intermediate Similarity	NPC474389
0.8061	Intermediate Similarity	NPC149265
0.8049	Intermediate Similarity	NPC122141
0.8025	Intermediate Similarity	NPC34844
0.8013	Intermediate Similarity	NPC115611
0.7976	Intermediate Similarity	NPC97343
0.7962	Intermediate Similarity	NPC473868
0.7962	Intermediate Similarity	NPC63157
0.791	Intermediate Similarity	NPC231536
0.7904	Intermediate Similarity	NPC195507
0.7898	Intermediate Similarity	NPC59084
0.7898	Intermediate Similarity	NPC2949
0.7895	Intermediate Similarity	NPC22079
0.7882	Intermediate Similarity	NPC64055
0.7875	Intermediate Similarity	NPC316069
0.7857	Intermediate Similarity	NPC109447
0.7826	Intermediate Similarity	NPC469811
0.7812	Intermediate Similarity	NPC470440
0.7778	Intermediate Similarity	NPC321911
0.7771	Intermediate Similarity	NPC475990
0.7771	Intermediate Similarity	NPC474880
0.7771	Intermediate Similarity	NPC221786
0.7764	Intermediate Similarity	NPC63545
0.7756	Intermediate Similarity	NPC96102
0.7748	Intermediate Similarity	NPC250361
0.7722	Intermediate Similarity	NPC73767
0.7716	Intermediate Similarity	NPC21605
0.7716	Intermediate Similarity	NPC201380
0.7716	Intermediate Similarity	NPC179787
0.7707	Intermediate Similarity	NPC84911
0.7707	Intermediate Similarity	NPC105127
0.7697	Intermediate Similarity	NPC476297
0.7697	Intermediate Similarity	NPC476219
0.7688	Intermediate Similarity	NPC121903
0.7673	Intermediate Similarity	NPC469768
0.7673	Intermediate Similarity	NPC469783
0.7673	Intermediate Similarity	NPC469784
0.7673	Intermediate Similarity	NPC469761
0.7673	Intermediate Similarity	NPC469779
0.7673	Intermediate Similarity	NPC469767
0.7673	Intermediate Similarity	NPC469780
0.7647	Intermediate Similarity	NPC473762
0.7643	Intermediate Similarity	NPC29886
0.7643	Intermediate Similarity	NPC261195
0.7636	Intermediate Similarity	NPC325903
0.7625	Intermediate Similarity	NPC469766
0.7622	Intermediate Similarity	NPC33421
0.7619	Intermediate Similarity	NPC229173
0.7613	Intermediate Similarity	NPC475450
0.761	Intermediate Similarity	NPC110126
0.76	Intermediate Similarity	NPC276540
0.76	Intermediate Similarity	NPC233050
0.76	Intermediate Similarity	NPC41174
0.7597	Intermediate Similarity	NPC473587
0.7574	Intermediate Similarity	NPC225018
0.7572	Intermediate Similarity	NPC288074
0.7562	Intermediate Similarity	NPC279081
0.7562	Intermediate Similarity	NPC284635
0.7548	Intermediate Similarity	NPC475428
0.7527	Intermediate Similarity	NPC23420
0.7527	Intermediate Similarity	NPC205254
0.7527	Intermediate Similarity	NPC106771
0.7527	Intermediate Similarity	NPC303820
0.7514	Intermediate Similarity	NPC275292
0.7514	Intermediate Similarity	NPC243381
0.75	Intermediate Similarity	NPC179365
0.75	Intermediate Similarity	NPC316811
0.75	Intermediate Similarity	NPC82295
0.7487	Intermediate Similarity	NPC52909
0.7487	Intermediate Similarity	NPC475935
0.7487	Intermediate Similarity	NPC94211
0.7485	Intermediate Similarity	NPC314372
0.7473	Intermediate Similarity	NPC220797
0.7473	Intermediate Similarity	NPC268744
0.7473	Intermediate Similarity	NPC474318
0.7473	Intermediate Similarity	NPC153123
0.7473	Intermediate Similarity	NPC475914
0.7473	Intermediate Similarity	NPC201266
0.7471	Intermediate Similarity	NPC253687
0.7469	Intermediate Similarity	NPC190296
0.7456	Intermediate Similarity	NPC56765
0.7456	Intermediate Similarity	NPC6436
0.7453	Intermediate Similarity	NPC230002
0.7452	Intermediate Similarity	NPC473930
0.7443	Intermediate Similarity	NPC240088
0.7443	Intermediate Similarity	NPC473380
0.7442	Intermediate Similarity	NPC49217
0.7439	Intermediate Similarity	NPC288838
0.7433	Intermediate Similarity	NPC166209
0.7433	Intermediate Similarity	NPC269203
0.7433	Intermediate Similarity	NPC13456
0.7433	Intermediate Similarity	NPC77241
0.7427	Intermediate Similarity	NPC21174
0.7427	Intermediate Similarity	NPC271797
0.741	Intermediate Similarity	NPC53947
0.7401	Intermediate Similarity	NPC265710
0.7396	Intermediate Similarity	NPC236711
0.738	Intermediate Similarity	NPC237414
0.7378	Intermediate Similarity	NPC159856
0.7371	Intermediate Similarity	NPC470702
0.7371	Intermediate Similarity	NPC473218
0.7362	Intermediate Similarity	NPC20144
0.736	Intermediate Similarity	NPC16659
0.7356	Intermediate Similarity	NPC474897
0.7349	Intermediate Similarity	NPC37548
0.7333	Intermediate Similarity	NPC470703
0.7333	Intermediate Similarity	NPC110158
0.7326	Intermediate Similarity	NPC317105
0.731	Intermediate Similarity	NPC477114
0.7305	Intermediate Similarity	NPC105818
0.7305	Intermediate Similarity	NPC24678
0.7299	Intermediate Similarity	NPC317430
0.7289	Intermediate Similarity	NPC471957
0.7289	Intermediate Similarity	NPC114209
0.7286	Intermediate Similarity	NPC474195
0.7273	Intermediate Similarity	NPC475736
0.7267	Intermediate Similarity	NPC81561
0.7263	Intermediate Similarity	NPC473761
0.7262	Intermediate Similarity	NPC470233
0.7251	Intermediate Similarity	NPC41257
0.7251	Intermediate Similarity	NPC206819
0.7251	Intermediate Similarity	NPC318065
0.7225	Intermediate Similarity	NPC90723
0.7219	Intermediate Similarity	NPC469765
0.7219	Intermediate Similarity	NPC200214
0.7219	Intermediate Similarity	NPC73952
0.7219	Intermediate Similarity	NPC25008
0.7219	Intermediate Similarity	NPC469760
0.7219	Intermediate Similarity	NPC259644
0.7219	Intermediate Similarity	NPC469763
0.7219	Intermediate Similarity	NPC469786
0.7212	Intermediate Similarity	NPC242556
0.72	Intermediate Similarity	NPC148140
0.7196	Intermediate Similarity	NPC477004
0.7194	Intermediate Similarity	NPC128084
0.7193	Intermediate Similarity	NPC286427
0.7193	Intermediate Similarity	NPC216643
0.7191	Intermediate Similarity	NPC280852
0.7189	Intermediate Similarity	NPC243716
0.7178	Intermediate Similarity	NPC312092
0.7178	Intermediate Similarity	NPC104483
0.7176	Intermediate Similarity	NPC70922
0.7176	Intermediate Similarity	NPC80597
0.7176	Intermediate Similarity	NPC211572
0.7176	Intermediate Similarity	NPC75540
0.7176	Intermediate Similarity	NPC38736
0.7176	Intermediate Similarity	NPC470507
0.7176	Intermediate Similarity	NPC212376
0.7175	Intermediate Similarity	NPC161861
0.7175	Intermediate Similarity	NPC472123
0.716	Intermediate Similarity	NPC470823
0.716	Intermediate Similarity	NPC216713
0.7151	Intermediate Similarity	NPC135141
0.7151	Intermediate Similarity	NPC92796
0.7143	Intermediate Similarity	NPC474196
0.7143	Intermediate Similarity	NPC187951
0.7135	Intermediate Similarity	NPC469785
0.7135	Intermediate Similarity	NPC285469
0.7112	Intermediate Similarity	NPC88315
0.711	Intermediate Similarity	NPC44773
0.711	Intermediate Similarity	NPC279918
0.711	Intermediate Similarity	NPC215584
0.7105	Intermediate Similarity	NPC54102
0.7105	Intermediate Similarity	NPC162689
0.7101	Intermediate Similarity	NPC40070
0.7101	Intermediate Similarity	NPC148592
0.7093	Intermediate Similarity	NPC469762
0.7083	Intermediate Similarity	NPC477134
0.7083	Intermediate Similarity	NPC470111
0.7072	Intermediate Similarity	NPC469896
0.7069	Intermediate Similarity	NPC282231
0.7062	Intermediate Similarity	NPC474168

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 NPC247987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	456
0.1-0.2	987
0.2-0.3	1125
0.3-0.4	2205
0.4-0.5	2399
0.5-0.6	1528
0.6-0.7	413
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7962	Intermediate Similarity	NPD1722	Approved
0.7911	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2150	Discontinued
0.7834	Intermediate Similarity	NPD786	Approved
0.7824	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6828	Phase 2
0.7821	Intermediate Similarity	NPD1262	Discovery
0.7764	Intermediate Similarity	NPD1683	Approved
0.7756	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4181	Approved
0.7561	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5254	Discontinued
0.7529	Intermediate Similarity	NPD4128	Approved
0.75	Intermediate Similarity	NPD2071	Approved
0.75	Intermediate Similarity	NPD2069	Approved
0.75	Intermediate Similarity	NPD2070	Approved
0.75	Intermediate Similarity	NPD2068	Approved
0.7469	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4047	Discontinued
0.7455	Intermediate Similarity	NPD3100	Discontinued
0.7425	Intermediate Similarity	NPD2837	Discontinued
0.7416	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4462	Approved
0.741	Intermediate Similarity	NPD4463	Approved
0.7405	Intermediate Similarity	NPD3385	Approved
0.7384	Intermediate Similarity	NPD1313	Approved
0.7384	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5962	Phase 2
0.7337	Intermediate Similarity	NPD2927	Phase 3
0.7326	Intermediate Similarity	NPD3323	Discontinued
0.7318	Intermediate Similarity	NPD1895	Discontinued
0.7305	Intermediate Similarity	NPD2172	Phase 1
0.7303	Intermediate Similarity	NPD8386	Phase 2
0.7288	Intermediate Similarity	NPD2367	Phase 2
0.7283	Intermediate Similarity	NPD509	Phase 3
0.7261	Intermediate Similarity	NPD3654	Approved
0.7257	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1994	Approved
0.7233	Intermediate Similarity	NPD1993	Approved
0.7233	Intermediate Similarity	NPD1995	Approved
0.7207	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5730	Phase 2
0.7207	Intermediate Similarity	NPD40	Phase 2
0.7184	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1248	Discontinued
0.7143	Intermediate Similarity	NPD439	Approved
0.7143	Intermediate Similarity	NPD438	Approved
0.7134	Intermediate Similarity	NPD991	Phase 2
0.7134	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1708	Approved
0.7127	Intermediate Similarity	NPD1707	Approved
0.7119	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3609	Approved
0.7119	Intermediate Similarity	NPD3610	Approved
0.7102	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD2640	Approved
0.7102	Intermediate Similarity	NPD2641	Approved
0.7088	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD680	Discontinued
0.7072	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD947	Approved
0.7043	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1183	Approved
0.7039	Intermediate Similarity	NPD5065	Approved
0.7037	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5787	Discontinued
0.7027	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4811	Discontinued
0.7011	Intermediate Similarity	NPD1404	Approved
0.7011	Intermediate Similarity	NPD1403	Approved
0.7006	Intermediate Similarity	NPD5671	Approved
0.7	Intermediate Similarity	NPD2880	Discontinued
0.6995	Remote Similarity	NPD4441	Phase 2
0.6994	Remote Similarity	NPD1253	Approved
0.6994	Remote Similarity	NPD1254	Approved
0.6994	Remote Similarity	NPD1255	Approved
0.6994	Remote Similarity	NPD1256	Approved
0.6977	Remote Similarity	NPD6285	Phase 2
0.6966	Remote Similarity	NPD1326	Approved
0.6966	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1325	Approved
0.6961	Remote Similarity	NPD7111	Discontinued
0.6951	Remote Similarity	NPD6554	Approved
0.6951	Remote Similarity	NPD45	Approved
0.6944	Remote Similarity	NPD3799	Suspended
0.6915	Remote Similarity	NPD7709	Discontinued
0.691	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3475	Approved
0.6894	Remote Similarity	NPD3476	Approved
0.6893	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6595	Phase 3
0.6882	Remote Similarity	NPD2793	Discontinued
0.6882	Remote Similarity	NPD2591	Phase 2
0.6882	Remote Similarity	NPD4547	Phase 3
0.6882	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6794	Approved
0.6854	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2639	Approved
0.6854	Remote Similarity	NPD2642	Approved
0.6852	Remote Similarity	NPD1251	Discontinued
0.6845	Remote Similarity	NPD2006	Phase 2
0.6842	Remote Similarity	NPD2430	Phase 2
0.6839	Remote Similarity	NPD2580	Discontinued
0.6829	Remote Similarity	NPD4880	Discontinued
0.6828	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD6664	Approved
0.6818	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2442	Approved
0.6818	Remote Similarity	NPD2443	Approved
0.6813	Remote Similarity	NPD1598	Discontinued
0.6813	Remote Similarity	NPD2119	Approved
0.6813	Remote Similarity	NPD4075	Phase 2
0.6813	Remote Similarity	NPD2118	Approved
0.6811	Remote Similarity	NPD3512	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5473	Discontinued
0.6792	Remote Similarity	NPD1949	Approved
0.6792	Remote Similarity	NPD1950	Approved
0.6791	Remote Similarity	NPD706	Phase 1
0.6789	Remote Similarity	NPD4615	Phase 2
0.6782	Remote Similarity	NPD976	Approved
0.6782	Remote Similarity	NPD975	Approved
0.6782	Remote Similarity	NPD977	Approved
0.678	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5436	Phase 1
0.6776	Remote Similarity	NPD3505	Approved
0.6776	Remote Similarity	NPD3506	Approved
0.6776	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4142	Discontinued
0.6768	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.676	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.676	Remote Similarity	NPD1215	Discontinued
0.6755	Remote Similarity	NPD3961	Discontinued
0.6744	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3114	Approved
0.6743	Remote Similarity	NPD3115	Approved
0.6743	Remote Similarity	NPD3112	Approved
0.6743	Remote Similarity	NPD3113	Approved
0.6742	Remote Similarity	NPD5140	Approved
0.6742	Remote Similarity	NPD5138	Approved
0.6739	Remote Similarity	NPD1327	Discontinued
0.6739	Remote Similarity	NPD4076	Approved
0.6739	Remote Similarity	NPD4079	Approved
0.6738	Remote Similarity	NPD2868	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3830	Phase 1
0.6735	Remote Similarity	NPD3015	Discontinued
0.6724	Remote Similarity	NPD1917	Discontinued
0.6722	Remote Similarity	NPD2333	Discontinued
0.6722	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7618	Phase 3
0.6719	Remote Similarity	NPD7619	Phase 3
0.6709	Remote Similarity	NPD1561	Phase 2
0.6706	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1030	Approved
0.6705	Remote Similarity	NPD1027	Approved
0.6705	Remote Similarity	NPD3835	Phase 3
0.6705	Remote Similarity	NPD3833	Phase 3
0.6705	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD1333	Phase 3
0.6704	Remote Similarity	NPD2915	Discontinued
0.6703	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6469	Phase 3
0.6701	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD715	Phase 3
0.6686	Remote Similarity	NPD2165	Phase 1
0.6686	Remote Similarity	NPD1592	Phase 3
0.6685	Remote Similarity	NPD1016	Phase 2
0.6685	Remote Similarity	NPD1015	Phase 2
0.6685	Remote Similarity	NPD2144	Approved
0.6684	Remote Similarity	NPD1043	Phase 3
0.6667	Remote Similarity	NPD4028	Approved
0.6667	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4030	Approved
0.6667	Remote Similarity	NPD482	Approved
0.6667	Remote Similarity	NPD4029	Approved
0.6667	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7006	Approved
0.6649	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD404	Discontinued
0.6646	Remote Similarity	NPD809	Discontinued
0.6646	Remote Similarity	NPD803	Phase 1
0.6632	Remote Similarity	NPD8110	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