NPASS Compound

Structure

NPC307191 OpenBabel07101718312D 22 24 0 0 0 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 -3.7524 0.6000 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 -4.7469 0.4954 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 0 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 -4.9280 2.2180 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 -3.9334 2.3225 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5158 3.0270 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 -5.3347 1.3044 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 3 1 0 0 0 0 2 7 1 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 21 1 0 0 0 0 8 20 2 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	359.07
Volume:	315.435
LogP:	2.529
LogD:	1.976
LogS:	-3.665
# Rotatable Bonds:	6
TPSA:	90.58
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	2.591
Fsp3:	0.25
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:	-5.253
MDCK Permeability:	1.228612927661743e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.513
Plasma Protein Binding (PPB):	88.59143829345703%
Volume Distribution (VD):	2.439
Pgp-substrate:	15.172161102294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.82
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.903
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.099

ADMET: Excretion

Clearance (CL):	3.502
Half-life (T1/2):	0.443

ADMET: Toxicity

hERG Blockers:	0.724
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.138
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.327
Carcinogencity:	0.448
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC307191

Natural Product ID:	NPC307191
*Common Name:**	Opacaline A
IUPAC Name:	2-[4-(7-bromo-9H-pyrido[3,4-b]indol-1-yl)butyl]guanidine
Synonyms:	Opacaline A
Standard InCHIKey:	RYDDJEFQYPXRAF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18BrN5/c17-10-4-5-11-12-6-8-20-13(15(12)22-14(11)9-10)3-1-2-7-21-16(18)19/h4-6,8-9,22H,1-3,7H2,(H4,18,19,21)
SMILES:	NC(=N)NCCCCc1nccc2c1[nH]c1c2ccc(c1)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821995
PubChem CID:	54669752
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.	New Zealand	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	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
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	79000.0	nM	PMID[527287]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	30000.0	nM	PMID[527287]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	86000.0	nM	PMID[527287]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	130000.0	nM	PMID[527287]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2500.0	nM	PMID[527287]

☑ 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 NPC307191 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	1416
0.1-0.2	15640
0.2-0.3	17586
0.3-0.4	3528
0.4-0.5	1919
0.5-0.6	1522
0.6-0.7	792
0.7-0.8	236
0.8-0.85	40
0.85-0.9	11
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC108011
0.9317	High Similarity	NPC274229
0.9273	High Similarity	NPC474958
0.9207	High Similarity	NPC82331
0.9193	High Similarity	NPC470203
0.9136	High Similarity	NPC247987
0.913	High Similarity	NPC470204
0.908	High Similarity	NPC17751
0.878	High Similarity	NPC122141
0.8704	High Similarity	NPC141926
0.8698	High Similarity	NPC477611
0.8693	High Similarity	NPC231536
0.869	High Similarity	NPC97343
0.8647	High Similarity	NPC280297
0.8623	High Similarity	NPC280864
0.8571	High Similarity	NPC469811
0.8519	High Similarity	NPC321911
0.8509	High Similarity	NPC63545
0.8492	Intermediate Similarity	NPC477166
0.8492	Intermediate Similarity	NPC304187
0.8492	Intermediate Similarity	NPC477167
0.8492	Intermediate Similarity	NPC473342
0.8476	Intermediate Similarity	NPC325903
0.8457	Intermediate Similarity	NPC179787
0.8457	Intermediate Similarity	NPC201380
0.8343	Intermediate Similarity	NPC474180
0.8343	Intermediate Similarity	NPC188821
0.8333	Intermediate Similarity	NPC204141
0.8293	Intermediate Similarity	NPC2272
0.8284	Intermediate Similarity	NPC225018
0.8282	Intermediate Similarity	NPC143872
0.8235	Intermediate Similarity	NPC149265
0.8204	Intermediate Similarity	NPC34844
0.8162	Intermediate Similarity	NPC474389
0.8144	Intermediate Similarity	NPC232798
0.8129	Intermediate Similarity	NPC317105
0.8118	Intermediate Similarity	NPC237414
0.8107	Intermediate Similarity	NPC236711
0.807	Intermediate Similarity	NPC253687
0.8061	Intermediate Similarity	NPC316069
0.7977	Intermediate Similarity	NPC2165
0.7975	Intermediate Similarity	NPC469768
0.7975	Intermediate Similarity	NPC469767
0.7975	Intermediate Similarity	NPC469783
0.7975	Intermediate Similarity	NPC469779
0.7975	Intermediate Similarity	NPC469780
0.7975	Intermediate Similarity	NPC469784
0.7975	Intermediate Similarity	NPC115611
0.7975	Intermediate Similarity	NPC469761
0.7952	Intermediate Similarity	NPC288838
0.795	Intermediate Similarity	NPC96102
0.7927	Intermediate Similarity	NPC469766
0.7917	Intermediate Similarity	NPC53947
0.7914	Intermediate Similarity	NPC73767
0.7901	Intermediate Similarity	NPC84911
0.7901	Intermediate Similarity	NPC105127
0.7895	Intermediate Similarity	NPC473761
0.7884	Intermediate Similarity	NPC106771
0.7884	Intermediate Similarity	NPC303820
0.7884	Intermediate Similarity	NPC205254
0.7884	Intermediate Similarity	NPC23420
0.7882	Intermediate Similarity	NPC476297
0.7882	Intermediate Similarity	NPC476219
0.7865	Intermediate Similarity	NPC280852
0.7842	Intermediate Similarity	NPC475935
0.7842	Intermediate Similarity	NPC94211
0.7842	Intermediate Similarity	NPC52909
0.784	Intermediate Similarity	NPC29886
0.784	Intermediate Similarity	NPC261195
0.7831	Intermediate Similarity	NPC475914
0.7831	Intermediate Similarity	NPC474318
0.7831	Intermediate Similarity	NPC153123
0.7831	Intermediate Similarity	NPC268744
0.7831	Intermediate Similarity	NPC201266
0.7831	Intermediate Similarity	NPC220797
0.7805	Intermediate Similarity	NPC110126
0.7805	Intermediate Similarity	NPC316811
0.7798	Intermediate Similarity	NPC470111
0.7791	Intermediate Similarity	NPC125746
0.7789	Intermediate Similarity	NPC13456
0.7789	Intermediate Similarity	NPC166209
0.7789	Intermediate Similarity	NPC77241
0.7789	Intermediate Similarity	NPC269203
0.7778	Intermediate Similarity	NPC233050
0.7778	Intermediate Similarity	NPC276540
0.7765	Intermediate Similarity	NPC470233
0.7758	Intermediate Similarity	NPC279081
0.7739	Intermediate Similarity	NPC477114
0.773	Intermediate Similarity	NPC325252
0.7716	Intermediate Similarity	NPC473218
0.7716	Intermediate Similarity	NPC470702
0.7702	Intermediate Similarity	NPC82295
0.7692	Intermediate Similarity	NPC275292
0.7692	Intermediate Similarity	NPC243381
0.7688	Intermediate Similarity	NPC216643
0.7679	Intermediate Similarity	NPC314372
0.7677	Intermediate Similarity	NPC470703
0.7669	Intermediate Similarity	NPC198988
0.7665	Intermediate Similarity	NPC190296
0.7651	Intermediate Similarity	NPC230002
0.7644	Intermediate Similarity	NPC56765
0.7644	Intermediate Similarity	NPC92796
0.7644	Intermediate Similarity	NPC135141
0.7637	Intermediate Similarity	NPC16659
0.7633	Intermediate Similarity	NPC470323
0.7627	Intermediate Similarity	NPC49217
0.7624	Intermediate Similarity	NPC240088
0.7624	Intermediate Similarity	NPC473380
0.7611	Intermediate Similarity	NPC317054
0.7611	Intermediate Similarity	NPC471579
0.7602	Intermediate Similarity	NPC24678
0.7602	Intermediate Similarity	NPC105818
0.76	Intermediate Similarity	NPC215584
0.76	Intermediate Similarity	NPC44773
0.7596	Intermediate Similarity	NPC267078
0.7596	Intermediate Similarity	NPC935
0.759	Intermediate Similarity	NPC88097
0.7582	Intermediate Similarity	NPC265710
0.7574	Intermediate Similarity	NPC159856
0.7571	Intermediate Similarity	NPC195507
0.756	Intermediate Similarity	NPC474357
0.7545	Intermediate Similarity	NPC284635
0.7538	Intermediate Similarity	NPC470505
0.7536	Intermediate Similarity	NPC156003
0.7528	Intermediate Similarity	NPC478183
0.7515	Intermediate Similarity	NPC218268
0.7514	Intermediate Similarity	NPC469760
0.7514	Intermediate Similarity	NPC469763
0.7514	Intermediate Similarity	NPC25008
0.7514	Intermediate Similarity	NPC110158
0.7514	Intermediate Similarity	NPC73952
0.7514	Intermediate Similarity	NPC90723
0.7514	Intermediate Similarity	NPC469786
0.7514	Intermediate Similarity	NPC469765
0.7514	Intermediate Similarity	NPC259644
0.75	Intermediate Similarity	NPC40070
0.7486	Intermediate Similarity	NPC286427
0.7485	Intermediate Similarity	NPC471957
0.7471	Intermediate Similarity	NPC80597
0.7471	Intermediate Similarity	NPC70922
0.7471	Intermediate Similarity	NPC212376
0.7471	Intermediate Similarity	NPC75540
0.7471	Intermediate Similarity	NPC211572
0.7461	Intermediate Similarity	NPC477004
0.7451	Intermediate Similarity	NPC474195
0.7443	Intermediate Similarity	NPC41257
0.7443	Intermediate Similarity	NPC318065
0.7443	Intermediate Similarity	NPC206819
0.744	Intermediate Similarity	NPC2949
0.744	Intermediate Similarity	NPC59084
0.7438	Intermediate Similarity	NPC475736
0.7429	Intermediate Similarity	NPC469785
0.7416	Intermediate Similarity	NPC478184
0.7416	Intermediate Similarity	NPC478182
0.7414	Intermediate Similarity	NPC200214
0.7405	Intermediate Similarity	NPC191415
0.7396	Intermediate Similarity	NPC63157
0.7396	Intermediate Similarity	NPC473868
0.7391	Intermediate Similarity	NPC474196
0.7386	Intermediate Similarity	NPC469762
0.7366	Intermediate Similarity	NPC48938
0.7366	Intermediate Similarity	NPC102755
0.7365	Intermediate Similarity	NPC251722
0.7365	Intermediate Similarity	NPC314102
0.7363	Intermediate Similarity	NPC128084
0.7363	Intermediate Similarity	NPC64055
0.7356	Intermediate Similarity	NPC216713
0.7356	Intermediate Similarity	NPC470823
0.7345	Intermediate Similarity	NPC474880
0.7345	Intermediate Similarity	NPC221786
0.7345	Intermediate Similarity	NPC293487
0.7345	Intermediate Similarity	NPC475990
0.7345	Intermediate Similarity	NPC477591
0.7337	Intermediate Similarity	NPC116555
0.7333	Intermediate Similarity	NPC109447
0.7326	Intermediate Similarity	NPC284678
0.7317	Intermediate Similarity	NPC22079
0.7303	Intermediate Similarity	NPC229173
0.7293	Intermediate Similarity	NPC63751
0.7292	Intermediate Similarity	NPC88315
0.7284	Intermediate Similarity	NPC250361
0.7283	Intermediate Similarity	NPC121903
0.7273	Intermediate Similarity	NPC475450
0.7267	Intermediate Similarity	NPC470440
0.7262	Intermediate Similarity	NPC150259
0.7249	Intermediate Similarity	NPC62749
0.7247	Intermediate Similarity	NPC300238
0.7243	Intermediate Similarity	NPC59269
0.7241	Intermediate Similarity	NPC477610
0.724	Intermediate Similarity	NPC324149
0.7238	Intermediate Similarity	NPC49954
0.7238	Intermediate Similarity	NPC160105
0.7238	Intermediate Similarity	NPC474561
0.7231	Intermediate Similarity	NPC265576
0.7222	Intermediate Similarity	NPC311276
0.7208	Intermediate Similarity	NPC469308
0.7207	Intermediate Similarity	NPC279918
0.7205	Intermediate Similarity	NPC46358
0.7202	Intermediate Similarity	NPC326422
0.7196	Intermediate Similarity	NPC15102

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 NPC307191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	488
0.1-0.2	1004
0.2-0.3	1212
0.3-0.4	2301
0.4-0.5	1960
0.5-0.6	1471
0.6-0.7	616
0.7-0.8	95
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
0.8148	Intermediate Similarity	NPD1722	Approved
0.809	Intermediate Similarity	NPD1895	Discontinued
0.809	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2837	Discontinued
0.7914	Intermediate Similarity	NPD786	Approved
0.7877	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4181	Approved
0.7805	Intermediate Similarity	NPD2071	Approved
0.7805	Intermediate Similarity	NPD2070	Approved
0.7805	Intermediate Similarity	NPD2068	Approved
0.7805	Intermediate Similarity	NPD2069	Approved
0.7797	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD3100	Discontinued
0.7709	Intermediate Similarity	NPD4128	Approved
0.7627	Intermediate Similarity	NPD439	Approved
0.7627	Intermediate Similarity	NPD438	Approved
0.7614	Intermediate Similarity	NPD3323	Discontinued
0.7602	Intermediate Similarity	NPD2172	Phase 1
0.7584	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1313	Approved
0.756	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1993	Approved
0.7546	Intermediate Similarity	NPD1994	Approved
0.7546	Intermediate Similarity	NPD1995	Approved
0.7542	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD2793	Discontinued
0.7527	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1707	Approved
0.75	Intermediate Similarity	NPD6828	Phase 2
0.75	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1708	Approved
0.75	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2333	Discontinued
0.7473	Intermediate Similarity	NPD2367	Phase 2
0.7459	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2880	Discontinued
0.7446	Intermediate Similarity	NPD5962	Phase 2
0.7432	Intermediate Similarity	NPD7111	Discontinued
0.7429	Intermediate Similarity	NPD2927	Phase 3
0.7429	Intermediate Similarity	NPD2150	Discontinued
0.7396	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2640	Approved
0.7389	Intermediate Similarity	NPD2641	Approved
0.7384	Intermediate Similarity	NPD4547	Phase 3
0.7382	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1262	Discovery
0.7353	Intermediate Similarity	NPD2006	Phase 2
0.7341	Intermediate Similarity	NPD2430	Phase 2
0.7337	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1248	Discontinued
0.7322	Intermediate Similarity	NPD5065	Approved
0.7317	Intermediate Similarity	NPD715	Phase 3
0.7308	Intermediate Similarity	NPD3610	Approved
0.7308	Intermediate Similarity	NPD3609	Approved
0.7293	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1333	Phase 3
0.7273	Intermediate Similarity	NPD975	Approved
0.7273	Intermediate Similarity	NPD976	Approved
0.7273	Intermediate Similarity	NPD977	Approved
0.7263	Intermediate Similarity	NPD1016	Phase 2
0.7263	Intermediate Similarity	NPD1015	Phase 2
0.7258	Intermediate Similarity	NPD6595	Phase 3
0.725	Intermediate Similarity	NPD2443	Approved
0.725	Intermediate Similarity	NPD2442	Approved
0.7249	Intermediate Similarity	NPD706	Phase 1
0.7249	Intermediate Similarity	NPD4902	Discontinued
0.7241	Intermediate Similarity	NPD1183	Approved
0.724	Intermediate Similarity	NPD4615	Phase 2
0.7239	Intermediate Similarity	NPD991	Phase 2
0.7239	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD2008	Discontinued
0.7236	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1683	Approved
0.7216	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3475	Approved
0.7212	Intermediate Similarity	NPD3476	Approved
0.7211	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5254	Discontinued
0.7209	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1404	Approved
0.7207	Intermediate Similarity	NPD1403	Approved
0.7204	Intermediate Similarity	NPD1327	Discontinued
0.7204	Intermediate Similarity	NPD5730	Phase 2
0.7204	Intermediate Similarity	NPD40	Phase 2
0.72	Intermediate Similarity	NPD1027	Approved
0.72	Intermediate Similarity	NPD971	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1030	Approved
0.72	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3385	Approved
0.7179	Intermediate Similarity	NPD5462	Discontinued
0.7172	Intermediate Similarity	NPD3015	Discontinued
0.7166	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5436	Phase 1
0.7157	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4341	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2639	Approved
0.7143	Intermediate Similarity	NPD2642	Approved
0.7134	Intermediate Similarity	NPD2118	Approved
0.7134	Intermediate Similarity	NPD2119	Approved
0.7128	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2411	Approved
0.7104	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4462	Approved
0.7102	Intermediate Similarity	NPD4463	Approved
0.7092	Intermediate Similarity	NPD3830	Phase 1
0.709	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD509	Phase 3
0.7074	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6721	Phase 1
0.7066	Intermediate Similarity	NPD809	Discontinued
0.7066	Intermediate Similarity	NPD803	Phase 1
0.7059	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5418	Discontinued
0.7052	Intermediate Similarity	NPD4047	Discontinued
0.705	Intermediate Similarity	NPD2364	Suspended
0.7044	Intermediate Similarity	NPD2408	Discontinued
0.7039	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2580	Discontinued
0.7031	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7394	Phase 2
0.703	Intermediate Similarity	NPD1598	Discontinued
0.703	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1303	Phase 1
0.7022	Intermediate Similarity	NPD1917	Discontinued
0.7016	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4075	Phase 2
0.7005	Intermediate Similarity	NPD6664	Approved
0.7	Intermediate Similarity	NPD4872	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7619	Phase 3
0.699	Remote Similarity	NPD7618	Phase 3
0.6989	Remote Similarity	NPD1661	Suspended
0.6985	Remote Similarity	NPD6816	Phase 3
0.6983	Remote Similarity	NPD2165	Phase 1
0.6982	Remote Similarity	NPD4030	Approved
0.6982	Remote Similarity	NPD4029	Approved
0.6982	Remote Similarity	NPD4028	Approved
0.6979	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6469	Phase 3
0.6968	Remote Similarity	NPD3505	Approved
0.6968	Remote Similarity	NPD3506	Approved
0.6963	Remote Similarity	NPD5892	Approved
0.6959	Remote Similarity	NPD2818	Discontinued
0.6957	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3799	Suspended
0.6946	Remote Similarity	NPD3654	Approved
0.6944	Remote Similarity	NPD3114	Approved
0.6944	Remote Similarity	NPD3113	Approved
0.6944	Remote Similarity	NPD3115	Approved
0.6944	Remote Similarity	NPD3112	Approved
0.6943	Remote Similarity	NPD3961	Discontinued
0.6943	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2140	Approved
0.6941	Remote Similarity	NPD2141	Approved
0.6941	Remote Similarity	NPD2142	Approved
0.6939	Remote Similarity	NPD2445	Approved
0.6939	Remote Similarity	NPD2446	Approved
0.6931	Remote Similarity	NPD8386	Phase 2
0.6931	Remote Similarity	NPD4076	Approved
0.6931	Remote Similarity	NPD1893	Phase 2
0.6931	Remote Similarity	NPD4079	Approved
0.6931	Remote Similarity	NPD1892	Phase 2
0.6927	Remote Similarity	NPD695	Discontinued
0.6911	Remote Similarity	NPD5106	Approved
0.6911	Remote Similarity	NPD4441	Phase 2
0.6911	Remote Similarity	NPD5105	Approved
0.6907	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2591	Phase 2
0.6891	Remote Similarity	NPD7026	Phase 2
0.6891	Remote Similarity	NPD5642	Approved
0.6888	Remote Similarity	NPD3431	Approved
0.6888	Remote Similarity	NPD3430	Approved
0.6885	Remote Similarity	NPD8026	Phase 1
0.6884	Remote Similarity	NPD1982	Phase 1
0.6882	Remote Similarity	NPD3944	Approved
0.6882	Remote Similarity	NPD3942	Approved

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