NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	331.07
Volume:	296.078
LogP:	4.146
LogD:	3.663
LogS:	-4.562
# Rotatable Bonds:	3
TPSA:	54.7
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	3.069
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.78
MDCK Permeability:	1.5733039617771283e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.076
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.628
Plasma Protein Binding (PPB):	91.96731567382812%
Volume Distribution (VD):	3.158
Pgp-substrate:	10.823479652404785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.852
CYP2C19-inhibitor:	0.635
CYP2C19-substrate:	0.379
CYP2C9-inhibitor:	0.452
CYP2C9-substrate:	0.21
CYP2D6-inhibitor:	0.914
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.689
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	2.26
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.822
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.801
AMES Toxicity:	0.215
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.246
Carcinogencity:	0.241
Eye Corrosion:	0.009
Eye Irritation:	0.034
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC474958

Natural Product ID:	NPC474958
*Common Name:**	Eudistalbin A
IUPAC Name:	1-(7-bromo-9H-pyrido[3,4-b]indol-1-yl)-3-methylbutan-1-amine
Synonyms:
Standard InCHIKey:	PWUUECLZOMPMHQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18BrN3/c1-9(2)7-13(18)16-15-12(5-6-19-16)11-4-3-10(17)8-14(11)20-15/h3-6,8-9,13,20H,7,18H2,1-2H3
SMILES:	CC(C)CC(C1=NC=CC2=C1NC3=C2C=CC(=C3)Br)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490167
PubChem CID:	5487489
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
NPO6291	Eudistoma album	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512602]
NPO6291	Eudistoma album	Species	Polycitoridae	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
ED50	2
Others	3

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.2	ug ml-1	PMID[464861]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	100.0	%	PMID[464861]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	92.0	%	PMID[464861]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	0.0	%	PMID[464861]

☑ 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 NPC474958 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	1149
0.1-0.2	14711
0.2-0.3	18170
0.3-0.4	3918
0.4-0.5	1957
0.5-0.6	1490
0.6-0.7	914
0.7-0.8	298
0.8-0.85	70
0.85-0.9	14
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC82331
0.9554	High Similarity	NPC274229
0.9273	High Similarity	NPC307191
0.9045	High Similarity	NPC141926
0.9024	High Similarity	NPC477611
0.9006	High Similarity	NPC231536
0.8902	High Similarity	NPC97343
0.8854	High Similarity	NPC321911
0.8824	High Similarity	NPC108011
0.879	High Similarity	NPC201380
0.879	High Similarity	NPC179787
0.879	High Similarity	NPC469811
0.8726	High Similarity	NPC63545
0.8688	High Similarity	NPC325903
0.8616	High Similarity	NPC2272
0.8606	High Similarity	NPC17751
0.8545	High Similarity	NPC149265
0.8545	High Similarity	NPC247987
0.8519	High Similarity	NPC34844
0.85	High Similarity	NPC237414
0.8485	Intermediate Similarity	NPC470203
0.8434	Intermediate Similarity	NPC317105
0.8424	Intermediate Similarity	NPC470204
0.8415	Intermediate Similarity	NPC236711
0.8408	Intermediate Similarity	NPC115611
0.8333	Intermediate Similarity	NPC53947
0.8313	Intermediate Similarity	NPC122141
0.8291	Intermediate Similarity	NPC469779
0.8291	Intermediate Similarity	NPC469783
0.8291	Intermediate Similarity	NPC469767
0.8291	Intermediate Similarity	NPC469761
0.8291	Intermediate Similarity	NPC469780
0.8291	Intermediate Similarity	NPC469768
0.8291	Intermediate Similarity	NPC469784
0.8261	Intermediate Similarity	NPC316069
0.8256	Intermediate Similarity	NPC280852
0.8239	Intermediate Similarity	NPC469766
0.8228	Intermediate Similarity	NPC110126
0.8228	Intermediate Similarity	NPC316811
0.8228	Intermediate Similarity	NPC73767
0.8217	Intermediate Similarity	NPC84911
0.8217	Intermediate Similarity	NPC105127
0.821	Intermediate Similarity	NPC470111
0.8198	Intermediate Similarity	NPC280297
0.8171	Intermediate Similarity	NPC470233
0.8166	Intermediate Similarity	NPC2165
0.8166	Intermediate Similarity	NPC280864
0.8162	Intermediate Similarity	NPC473761
0.8153	Intermediate Similarity	NPC261195
0.8153	Intermediate Similarity	NPC29886
0.8153	Intermediate Similarity	NPC325252
0.8153	Intermediate Similarity	NPC96102
0.8152	Intermediate Similarity	NPC106771
0.8152	Intermediate Similarity	NPC23420
0.8152	Intermediate Similarity	NPC303820
0.8152	Intermediate Similarity	NPC205254
0.8148	Intermediate Similarity	NPC288838
0.8144	Intermediate Similarity	NPC56765
0.8108	Intermediate Similarity	NPC475935
0.8108	Intermediate Similarity	NPC52909
0.8108	Intermediate Similarity	NPC94211
0.8098	Intermediate Similarity	NPC474318
0.8098	Intermediate Similarity	NPC220797
0.8098	Intermediate Similarity	NPC153123
0.8098	Intermediate Similarity	NPC268744
0.8098	Intermediate Similarity	NPC475914
0.8098	Intermediate Similarity	NPC201266
0.8057	Intermediate Similarity	NPC233050
0.8057	Intermediate Similarity	NPC276540
0.8054	Intermediate Similarity	NPC77241
0.8054	Intermediate Similarity	NPC269203
0.8054	Intermediate Similarity	NPC13456
0.8054	Intermediate Similarity	NPC166209
0.8012	Intermediate Similarity	NPC63157
0.8012	Intermediate Similarity	NPC473868
0.8	Intermediate Similarity	NPC40070
0.7976	Intermediate Similarity	NPC216643
0.7975	Intermediate Similarity	NPC198988
0.7975	Intermediate Similarity	NPC314372
0.7967	Intermediate Similarity	NPC477167
0.7967	Intermediate Similarity	NPC304187
0.7967	Intermediate Similarity	NPC473342
0.7967	Intermediate Similarity	NPC477166
0.7966	Intermediate Similarity	NPC275292
0.7966	Intermediate Similarity	NPC243381
0.7964	Intermediate Similarity	NPC476297
0.7964	Intermediate Similarity	NPC476219
0.7963	Intermediate Similarity	NPC190296
0.795	Intermediate Similarity	NPC59084
0.795	Intermediate Similarity	NPC279081
0.7929	Intermediate Similarity	NPC41257
0.7929	Intermediate Similarity	NPC318065
0.7929	Intermediate Similarity	NPC206819
0.7898	Intermediate Similarity	NPC82295
0.7895	Intermediate Similarity	NPC90723
0.7892	Intermediate Similarity	NPC105818
0.7892	Intermediate Similarity	NPC24678
0.7888	Intermediate Similarity	NPC88097
0.7882	Intermediate Similarity	NPC44773
0.7882	Intermediate Similarity	NPC215584
0.787	Intermediate Similarity	NPC286427
0.784	Intermediate Similarity	NPC284635
0.784	Intermediate Similarity	NPC230002
0.7836	Intermediate Similarity	NPC225018
0.7829	Intermediate Similarity	NPC64055
0.7826	Intermediate Similarity	NPC188821
0.7826	Intermediate Similarity	NPC474180
0.7824	Intermediate Similarity	NPC92796
0.7824	Intermediate Similarity	NPC135141
0.7818	Intermediate Similarity	NPC143872
0.7812	Intermediate Similarity	NPC218268
0.7803	Intermediate Similarity	NPC109447
0.7798	Intermediate Similarity	NPC469786
0.7798	Intermediate Similarity	NPC25008
0.7798	Intermediate Similarity	NPC469760
0.7798	Intermediate Similarity	NPC469763
0.7798	Intermediate Similarity	NPC469765
0.7798	Intermediate Similarity	NPC73952
0.7798	Intermediate Similarity	NPC259644
0.7784	Intermediate Similarity	NPC471579
0.7771	Intermediate Similarity	NPC21605
0.7771	Intermediate Similarity	NPC471957
0.7758	Intermediate Similarity	NPC204141
0.7758	Intermediate Similarity	NPC159856
0.7754	Intermediate Similarity	NPC474389
0.7751	Intermediate Similarity	NPC211572
0.7751	Intermediate Similarity	NPC75540
0.7751	Intermediate Similarity	NPC212376
0.7751	Intermediate Similarity	NPC70922
0.7751	Intermediate Similarity	NPC80597
0.7746	Intermediate Similarity	NPC195507
0.773	Intermediate Similarity	NPC2949
0.7719	Intermediate Similarity	NPC474880
0.7719	Intermediate Similarity	NPC221786
0.7719	Intermediate Similarity	NPC475990
0.7701	Intermediate Similarity	NPC49954
0.7701	Intermediate Similarity	NPC474561
0.7701	Intermediate Similarity	NPC478183
0.7696	Intermediate Similarity	NPC470505
0.7692	Intermediate Similarity	NPC200214
0.7692	Intermediate Similarity	NPC232798
0.7688	Intermediate Similarity	NPC478182
0.7688	Intermediate Similarity	NPC478184
0.768	Intermediate Similarity	NPC110158
0.7674	Intermediate Similarity	NPC229173
0.7667	Intermediate Similarity	NPC191415
0.7654	Intermediate Similarity	NPC251722
0.7654	Intermediate Similarity	NPC314102
0.764	Intermediate Similarity	NPC121903
0.7633	Intermediate Similarity	NPC470823
0.7627	Intermediate Similarity	NPC288074
0.7619	Intermediate Similarity	NPC477004
0.7616	Intermediate Similarity	NPC477591
0.7614	Intermediate Similarity	NPC194411
0.761	Intermediate Similarity	NPC22079
0.7602	Intermediate Similarity	NPC473218
0.7602	Intermediate Similarity	NPC470702
0.7602	Intermediate Similarity	NPC469785
0.76	Intermediate Similarity	NPC160105
0.7582	Intermediate Similarity	NPC284678
0.7574	Intermediate Similarity	NPC33421
0.7566	Intermediate Similarity	NPC265576
0.7563	Intermediate Similarity	NPC470703
0.7562	Intermediate Similarity	NPC475450
0.7558	Intermediate Similarity	NPC469762
0.7557	Intermediate Similarity	NPC63751
0.7546	Intermediate Similarity	NPC150259
0.7545	Intermediate Similarity	NPC470440
0.754	Intermediate Similarity	NPC88315
0.7529	Intermediate Similarity	NPC253687
0.7529	Intermediate Similarity	NPC216713
0.7529	Intermediate Similarity	NPC282231
0.7527	Intermediate Similarity	NPC48938
0.7527	Intermediate Similarity	NPC102755
0.7514	Intermediate Similarity	NPC293487
0.75	Intermediate Similarity	NPC475428
0.7486	Intermediate Similarity	NPC311276
0.7486	Intermediate Similarity	NPC37423
0.7486	Intermediate Similarity	NPC275305
0.7475	Intermediate Similarity	NPC477610
0.7471	Intermediate Similarity	NPC279918
0.7468	Intermediate Similarity	NPC250361
0.7458	Intermediate Similarity	NPC201700
0.7452	Intermediate Similarity	NPC27740
0.7451	Intermediate Similarity	NPC245348
0.7446	Intermediate Similarity	NPC15102
0.7446	Intermediate Similarity	NPC308931
0.7446	Intermediate Similarity	NPC99939
0.7438	Intermediate Similarity	NPC473587
0.743	Intermediate Similarity	NPC314603
0.7425	Intermediate Similarity	NPC20144
0.7424	Intermediate Similarity	NPC207020
0.7416	Intermediate Similarity	NPC474897
0.7415	Intermediate Similarity	NPC60006
0.7414	Intermediate Similarity	NPC6436
0.7405	Intermediate Similarity	NPC94752
0.7405	Intermediate Similarity	NPC62749
0.7403	Intermediate Similarity	NPC68354
0.7403	Intermediate Similarity	NPC59269
0.7399	Intermediate Similarity	NPC476464

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 NPC474958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	459
0.1-0.2	949
0.2-0.3	1118
0.3-0.4	2393
0.4-0.5	2101
0.5-0.6	1494
0.6-0.7	524
0.7-0.8	104
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8471	Intermediate Similarity	NPD1722	Approved
0.8344	Intermediate Similarity	NPD786	Approved
0.8232	Intermediate Similarity	NPD2837	Discontinued
0.8228	Intermediate Similarity	NPD2070	Approved
0.8228	Intermediate Similarity	NPD2069	Approved
0.8228	Intermediate Similarity	NPD2068	Approved
0.8228	Intermediate Similarity	NPD2071	Approved
0.8153	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD3323	Discontinued
0.8075	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3100	Discontinued
0.7892	Intermediate Similarity	NPD2172	Phase 1
0.7848	Intermediate Similarity	NPD1993	Approved
0.7848	Intermediate Similarity	NPD1995	Approved
0.7848	Intermediate Similarity	NPD1994	Approved
0.7836	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD4181	Approved
0.7771	Intermediate Similarity	NPD3610	Approved
0.7771	Intermediate Similarity	NPD4547	Phase 3
0.7771	Intermediate Similarity	NPD3609	Approved
0.7759	Intermediate Similarity	NPD2641	Approved
0.7759	Intermediate Similarity	NPD2640	Approved
0.7744	Intermediate Similarity	NPD2006	Phase 2
0.7725	Intermediate Similarity	NPD2430	Phase 2
0.7709	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5065	Approved
0.7657	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD991	Phase 2
0.7643	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD715	Phase 3
0.7605	Intermediate Similarity	NPD1683	Approved
0.7584	Intermediate Similarity	NPD4128	Approved
0.7578	Intermediate Similarity	NPD3385	Approved
0.7569	Intermediate Similarity	NPD1895	Discontinued
0.7569	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD976	Approved
0.7544	Intermediate Similarity	NPD975	Approved
0.7544	Intermediate Similarity	NPD977	Approved
0.7542	Intermediate Similarity	NPD4075	Phase 2
0.7541	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2119	Approved
0.7532	Intermediate Similarity	NPD2118	Approved
0.7514	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3476	Approved
0.75	Intermediate Similarity	NPD3475	Approved
0.7485	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5254	Discontinued
0.7472	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1404	Approved
0.7471	Intermediate Similarity	NPD1403	Approved
0.7458	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6595	Phase 3
0.7412	Intermediate Similarity	NPD1183	Approved
0.7403	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3506	Approved
0.7403	Intermediate Similarity	NPD3505	Approved
0.7401	Intermediate Similarity	NPD2642	Approved
0.7401	Intermediate Similarity	NPD2639	Approved
0.7399	Intermediate Similarity	NPD3115	Approved
0.7399	Intermediate Similarity	NPD3113	Approved
0.7399	Intermediate Similarity	NPD2580	Discontinued
0.7399	Intermediate Similarity	NPD3114	Approved
0.7399	Intermediate Similarity	NPD3112	Approved
0.7368	Intermediate Similarity	NPD4463	Approved
0.7368	Intermediate Similarity	NPD4462	Approved
0.7366	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3961	Discontinued
0.7363	Intermediate Similarity	NPD4079	Approved
0.7363	Intermediate Similarity	NPD4076	Approved
0.7362	Intermediate Similarity	NPD4028	Approved
0.7362	Intermediate Similarity	NPD4029	Approved
0.7362	Intermediate Similarity	NPD4030	Approved
0.736	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD803	Phase 1
0.7345	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2165	Phase 1
0.7337	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3654	Approved
0.7318	Intermediate Similarity	NPD5436	Phase 1
0.7316	Intermediate Similarity	NPD7619	Phase 3
0.7316	Intermediate Similarity	NPD7618	Phase 3
0.7312	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD1313	Approved
0.7243	Intermediate Similarity	NPD5106	Approved
0.7243	Intermediate Similarity	NPD5105	Approved
0.7234	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5315	Discontinued
0.7219	Intermediate Similarity	NPD6217	Discontinued
0.7213	Intermediate Similarity	NPD2144	Approved
0.7207	Intermediate Similarity	NPD439	Approved
0.7207	Intermediate Similarity	NPD438	Approved
0.72	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD3038	Discontinued
0.7182	Intermediate Similarity	NPD6828	Phase 2
0.7182	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2367	Phase 2
0.7152	Intermediate Similarity	NPD3944	Approved
0.7152	Intermediate Similarity	NPD268	Approved
0.7152	Intermediate Similarity	NPD9598	Discontinued
0.7152	Intermediate Similarity	NPD3942	Approved
0.7152	Intermediate Similarity	NPD271	Approved
0.7152	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1661	Suspended
0.715	Intermediate Similarity	NPD2880	Discontinued
0.7143	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2793	Discontinued
0.7127	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD45	Approved
0.7126	Intermediate Similarity	NPD6554	Approved
0.7126	Intermediate Similarity	NPD1262	Discovery
0.712	Intermediate Similarity	NPD7111	Discontinued
0.7119	Intermediate Similarity	NPD5418	Discontinued
0.7112	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1248	Discontinued
0.7102	Intermediate Similarity	NPD2150	Discontinued
0.7098	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1708	Approved
0.7097	Intermediate Similarity	NPD1707	Approved
0.709	Intermediate Similarity	NPD8431	Approved
0.7083	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2333	Discontinued
0.7066	Intermediate Similarity	NPD1255	Approved
0.7066	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1254	Approved
0.7066	Intermediate Similarity	NPD1253	Approved
0.7066	Intermediate Similarity	NPD1256	Approved
0.7062	Intermediate Similarity	NPD6664	Approved
0.7059	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3015	Discontinued
0.7043	Intermediate Similarity	NPD5962	Phase 2
0.7041	Intermediate Similarity	NPD2075	Approved
0.7041	Intermediate Similarity	NPD2074	Approved
0.7041	Intermediate Similarity	NPD2072	Approved
0.7041	Intermediate Similarity	NPD2073	Approved
0.7039	Intermediate Similarity	NPD6771	Discontinued
0.7037	Intermediate Similarity	NPD9583	Approved
0.7031	Intermediate Similarity	NPD4615	Phase 2
0.7021	Intermediate Similarity	NPD4957	Phase 2
0.7011	Intermediate Similarity	NPD482	Approved
0.7006	Intermediate Similarity	NPD9392	Approved
0.7006	Intermediate Similarity	NPD9396	Approved
0.7	Intermediate Similarity	NPD3583	Phase 2
0.7	Intermediate Similarity	NPD7394	Phase 2
0.6995	Remote Similarity	NPD3116	Approved
0.6995	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3117	Approved
0.6994	Remote Similarity	NPD7469	Discontinued
0.6979	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD3348	Phase 2
0.6968	Remote Similarity	NPD2094	Phase 2
0.6968	Remote Similarity	NPD2095	Phase 2
0.6968	Remote Similarity	NPD2092	Phase 2
0.6961	Remote Similarity	NPD1333	Phase 3
0.6954	Remote Similarity	NPD4703	Approved
0.6954	Remote Similarity	NPD4702	Approved
0.695	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1015	Phase 2
0.6944	Remote Similarity	NPD1016	Phase 2
0.6942	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6178	Phase 3
0.6931	Remote Similarity	NPD2096	Phase 2
0.6931	Remote Similarity	NPD2091	Phase 2
0.6931	Remote Similarity	NPD7564	Discontinued
0.6923	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4047	Discontinued
0.6914	Remote Similarity	NPD9357	Approved
0.6912	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2927	Phase 3
0.6909	Remote Similarity	NPD947	Approved
0.69	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD1327	Discontinued
0.6895	Remote Similarity	NPD1227	Phase 2
0.6893	Remote Similarity	NPD3339	Approved
0.689	Remote Similarity	NPD1598	Discontinued
0.6888	Remote Similarity	NPD5462	Discontinued
0.6888	Remote Similarity	NPD3830	Phase 1
0.6885	Remote Similarity	NPD4639	Approved
0.6885	Remote Similarity	NPD4640	Approved
0.6885	Remote Similarity	NPD4638	Approved
0.6882	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD2442	Approved
0.6881	Remote Similarity	NPD2443	Approved
0.6879	Remote Similarity	NPD269	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