NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	186.08
Volume:	196.664
LogP:	1.717
LogD:	1.498
LogS:	-2.245
# Rotatable Bonds:	2
TPSA:	58.88
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	2.193
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.718
MDCK Permeability:	1.7470862076152116e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.523

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	88.47700500488281%
Volume Distribution (VD):	0.823
Pgp-substrate:	14.410829544067383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.351
CYP2C19-substrate:	0.212
CYP2C9-inhibitor:	0.154
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	8.319
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.518
Drug-inuced Liver Injury (DILI):	0.615
AMES Toxicity:	0.467
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.78
Skin Sensitization:	0.935
Carcinogencity:	0.15
Eye Corrosion:	0.052
Eye Irritation:	0.97
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC159856

Natural Product ID:	NPC159856
*Common Name:**	3-(1H-Indole-3-Yl)Acrylamide
IUPAC Name:	(E)-3-(1H-indol-3-yl)prop-2-enamide
Synonyms:	3-Indoleacrylamide
Standard InCHIKey:	ICPFDJZSCBDFMQ-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C11H10N2O/c12-11(14)6-5-8-7-13-10-4-2-1-3-9(8)10/h1-7,13H,(H2,12,14)/b6-5+
SMILES:	c1ccc2c(c1)c(/C=C/C(=N)O)c[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456734
PubChem CID:	21775218
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO11385	Chondria atropurpurea	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868166]
NPO11385	Chondria atropurpurea	Species	Rhodomelaceae	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3503	Organism	Nippostrongylus brasiliensis	Nippostrongylus brasiliensis	EC50	=	2370000.0	nM	PMID[510039]

☑ 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 NPC159856 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	880
0.1-0.2	10503
0.2-0.3	17444
0.3-0.4	7686
0.4-0.5	2512
0.5-0.6	1746
0.6-0.7	1204
0.7-0.8	548
0.8-0.85	106
0.85-0.9	28
0.9-0.95	35
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC105818
0.9714	High Similarity	NPC24678
0.9708	High Similarity	NPC190296
0.9568	High Similarity	NPC314372
0.9412	High Similarity	NPC96102
0.9343	High Similarity	NPC84911
0.9343	High Similarity	NPC105127
0.9315	High Similarity	NPC92796
0.9315	High Similarity	NPC135141
0.9296	High Similarity	NPC471957
0.927	High Similarity	NPC261195
0.927	High Similarity	NPC29886
0.9252	High Similarity	NPC131718
0.9209	High Similarity	NPC110126
0.9209	High Similarity	NPC73767
0.9172	High Similarity	NPC469760
0.9172	High Similarity	NPC25008
0.9172	High Similarity	NPC469763
0.9172	High Similarity	NPC259644
0.9172	High Similarity	NPC469786
0.9172	High Similarity	NPC469765
0.9172	High Similarity	NPC73952
0.9143	High Similarity	NPC279081
0.9143	High Similarity	NPC469761
0.9143	High Similarity	NPC469783
0.9143	High Similarity	NPC469767
0.9143	High Similarity	NPC469784
0.9143	High Similarity	NPC469780
0.9143	High Similarity	NPC469768
0.9143	High Similarity	NPC469779
0.9118	High Similarity	NPC82295
0.911	High Similarity	NPC70922
0.911	High Similarity	NPC80597
0.911	High Similarity	NPC75540
0.911	High Similarity	NPC212376
0.911	High Similarity	NPC211572
0.9103	High Similarity	NPC216713
0.9078	High Similarity	NPC469766
0.9048	High Similarity	NPC469785
0.9007	High Similarity	NPC230002
0.9007	High Similarity	NPC49217
0.9	High Similarity	NPC102423
0.8986	High Similarity	NPC469762
0.8867	High Similarity	NPC279918
0.8831	High Similarity	NPC470498
0.8828	High Similarity	NPC288838
0.8828	High Similarity	NPC143872
0.8808	High Similarity	NPC282231
0.88	High Similarity	NPC230869
0.8784	High Similarity	NPC200214
0.8767	High Similarity	NPC469811
0.875	High Similarity	NPC311276
0.8707	High Similarity	NPC321911
0.8699	High Similarity	NPC63545
0.8654	High Similarity	NPC313791
0.8649	High Similarity	NPC53947
0.8639	High Similarity	NPC201380
0.8639	High Similarity	NPC179787
0.8636	High Similarity	NPC160105
0.8636	High Similarity	NPC474561
0.8636	High Similarity	NPC49954
0.8636	High Similarity	NPC54988
0.8627	High Similarity	NPC40779
0.8591	High Similarity	NPC470823
0.8581	High Similarity	NPC63751
0.8581	High Similarity	NPC37548
0.8562	High Similarity	NPC242556
0.8553	High Similarity	NPC215795
0.8553	High Similarity	NPC176199
0.8533	High Similarity	NPC325903
0.8533	High Similarity	NPC141926
0.8526	High Similarity	NPC194411
0.85	High Similarity	NPC22079
0.8477	Intermediate Similarity	NPC34844
0.8462	Intermediate Similarity	NPC201700
0.8462	Intermediate Similarity	NPC78020
0.8462	Intermediate Similarity	NPC325252
0.8462	Intermediate Similarity	NPC218268
0.8418	Intermediate Similarity	NPC314603
0.8395	Intermediate Similarity	NPC220765
0.8392	Intermediate Similarity	NPC198988
0.8387	Intermediate Similarity	NPC194640
0.8366	Intermediate Similarity	NPC286427
0.8366	Intermediate Similarity	NPC216643
0.8366	Intermediate Similarity	NPC236711
0.8365	Intermediate Similarity	NPC275305
0.8365	Intermediate Similarity	NPC110500
0.8365	Intermediate Similarity	NPC37423
0.8365	Intermediate Similarity	NPC149155
0.8365	Intermediate Similarity	NPC203468
0.8355	Intermediate Similarity	NPC470507
0.8355	Intermediate Similarity	NPC38736
0.8345	Intermediate Similarity	NPC250361
0.8344	Intermediate Similarity	NPC204717
0.8333	Intermediate Similarity	NPC124005
0.8333	Intermediate Similarity	NPC187951
0.8322	Intermediate Similarity	NPC316069
0.8321	Intermediate Similarity	NPC41174
0.8313	Intermediate Similarity	NPC267885
0.8312	Intermediate Similarity	NPC206819
0.8312	Intermediate Similarity	NPC318065
0.8312	Intermediate Similarity	NPC41257
0.8312	Intermediate Similarity	NPC56765
0.831	Intermediate Similarity	NPC256893
0.8301	Intermediate Similarity	NPC141353
0.8293	Intermediate Similarity	NPC314002
0.8282	Intermediate Similarity	NPC48938
0.8276	Intermediate Similarity	NPC125746
0.8276	Intermediate Similarity	NPC150259
0.8261	Intermediate Similarity	NPC59269
0.8261	Intermediate Similarity	NPC248454
0.8261	Intermediate Similarity	NPC68354
0.8258	Intermediate Similarity	NPC122141
0.8258	Intermediate Similarity	NPC470204
0.8255	Intermediate Similarity	NPC470440
0.8242	Intermediate Similarity	NPC171171
0.8227	Intermediate Similarity	NPC473762
0.8224	Intermediate Similarity	NPC470233
0.8217	Intermediate Similarity	NPC42372
0.821	Intermediate Similarity	NPC11126
0.821	Intermediate Similarity	NPC248041
0.821	Intermediate Similarity	NPC283219
0.821	Intermediate Similarity	NPC126709
0.8205	Intermediate Similarity	NPC470203
0.8193	Intermediate Similarity	NPC46580
0.8182	Intermediate Similarity	NPC280290
0.8169	Intermediate Similarity	NPC473587
0.8163	Intermediate Similarity	NPC88097
0.8153	Intermediate Similarity	NPC90723
0.8153	Intermediate Similarity	NPC317105
0.8148	Intermediate Similarity	NPC96890
0.8148	Intermediate Similarity	NPC111275
0.8148	Intermediate Similarity	NPC151939
0.8148	Intermediate Similarity	NPC184964
0.8141	Intermediate Similarity	NPC215584
0.8141	Intermediate Similarity	NPC44773
0.8133	Intermediate Similarity	NPC285731
0.8129	Intermediate Similarity	NPC46358
0.8117	Intermediate Similarity	NPC471458
0.8112	Intermediate Similarity	NPC475428
0.811	Intermediate Similarity	NPC233936
0.8108	Intermediate Similarity	NPC59084
0.8108	Intermediate Similarity	NPC2949
0.8108	Intermediate Similarity	NPC115611
0.8101	Intermediate Similarity	NPC280864
0.8101	Intermediate Similarity	NPC17751
0.8098	Intermediate Similarity	NPC213468
0.8098	Intermediate Similarity	NPC233050
0.8098	Intermediate Similarity	NPC276540
0.8098	Intermediate Similarity	NPC55772
0.8079	Intermediate Similarity	NPC129042
0.8071	Intermediate Similarity	NPC27740
0.8065	Intermediate Similarity	NPC184476
0.8061	Intermediate Similarity	NPC163055
0.8056	Intermediate Similarity	NPC475450
0.8056	Intermediate Similarity	NPC179365
0.8054	Intermediate Similarity	NPC473868
0.8054	Intermediate Similarity	NPC63157
0.8049	Intermediate Similarity	NPC300688
0.8038	Intermediate Similarity	NPC149265
0.8037	Intermediate Similarity	NPC240088
0.8037	Intermediate Similarity	NPC284775
0.8037	Intermediate Similarity	NPC473380
0.8037	Intermediate Similarity	NPC145885
0.8037	Intermediate Similarity	NPC84827
0.8037	Intermediate Similarity	NPC14113
0.8026	Intermediate Similarity	NPC470111
0.8025	Intermediate Similarity	NPC293216
0.8013	Intermediate Similarity	NPC299594
0.8013	Intermediate Similarity	NPC204141
0.8012	Intermediate Similarity	NPC228835
0.8	Intermediate Similarity	NPC324149
0.8	Intermediate Similarity	NPC477166
0.8	Intermediate Similarity	NPC304187
0.8	Intermediate Similarity	NPC71037
0.8	Intermediate Similarity	NPC477815
0.8	Intermediate Similarity	NPC243381
0.8	Intermediate Similarity	NPC99666
0.8	Intermediate Similarity	NPC473930
0.8	Intermediate Similarity	NPC275292
0.7988	Intermediate Similarity	NPC265710
0.7987	Intermediate Similarity	NPC274229
0.7976	Intermediate Similarity	NPC278434
0.7975	Intermediate Similarity	NPC225018
0.7964	Intermediate Similarity	NPC163421
0.7964	Intermediate Similarity	NPC188387
0.7964	Intermediate Similarity	NPC15102
0.7952	Intermediate Similarity	NPC469358
0.7949	Intermediate Similarity	NPC285469
0.7939	Intermediate Similarity	NPC16659
0.7917	Intermediate Similarity	NPC235684
0.7917	Intermediate Similarity	NPC94752
0.7911	Intermediate Similarity	NPC473320
0.7905	Intermediate Similarity	NPC314102
0.7905	Intermediate Similarity	NPC251722
0.7904	Intermediate Similarity	NPC284678
0.7898	Intermediate Similarity	NPC129721
0.7879	Intermediate Similarity	NPC42979
0.787	Intermediate Similarity	NPC17059
0.787	Intermediate Similarity	NPC317030

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 NPC159856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	871
0.2-0.3	810
0.3-0.4	1800
0.4-0.5	2491
0.5-0.6	1786
0.6-0.7	814
0.7-0.8	220
0.8-0.85	19
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9412	High Similarity	NPD198	Clinical (unspecified phase)
0.9209	High Similarity	NPD786	Approved
0.9078	High Similarity	NPD1722	Approved
0.8947	High Similarity	NPD5069	Clinical (unspecified phase)
0.8776	High Similarity	NPD4462	Approved
0.8776	High Similarity	NPD4463	Approved
0.8718	High Similarity	NPD5065	Approved
0.8707	High Similarity	NPD4374	Clinical (unspecified phase)
0.8707	High Similarity	NPD3100	Discontinued
0.8649	High Similarity	NPD2172	Phase 1
0.8526	High Similarity	NPD4184	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD2837	Discontinued
0.8377	Intermediate Similarity	NPD1403	Approved
0.8377	Intermediate Similarity	NPD1404	Approved
0.8365	Intermediate Similarity	NPD482	Approved
0.8313	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2144	Approved
0.8261	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD3506	Approved
0.8261	Intermediate Similarity	NPD3505	Approved
0.825	Intermediate Similarity	NPD4128	Approved
0.821	Intermediate Similarity	NPD4079	Approved
0.821	Intermediate Similarity	NPD4076	Approved
0.8176	Intermediate Similarity	NPD1592	Phase 3
0.8165	Intermediate Similarity	NPD2639	Approved
0.8165	Intermediate Similarity	NPD2642	Approved
0.816	Intermediate Similarity	NPD6595	Phase 3
0.8156	Intermediate Similarity	NPD991	Phase 2
0.8156	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD3323	Discontinued
0.8148	Intermediate Similarity	NPD4181	Approved
0.8113	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2640	Approved
0.8113	Intermediate Similarity	NPD2641	Approved
0.811	Intermediate Similarity	NPD3038	Discontinued
0.8108	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD4075	Phase 2
0.8063	Intermediate Similarity	NPD1326	Approved
0.8063	Intermediate Similarity	NPD1325	Approved
0.8061	Intermediate Similarity	NPD2094	Phase 2
0.8061	Intermediate Similarity	NPD2095	Phase 2
0.8061	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD2092	Phase 2
0.8012	Intermediate Similarity	NPD2096	Phase 2
0.8012	Intermediate Similarity	NPD2091	Phase 2
0.7964	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD750	Phase 2
0.7953	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD5254	Discontinued
0.7917	Intermediate Similarity	NPD3654	Approved
0.7905	Intermediate Similarity	NPD1262	Discovery
0.7901	Intermediate Similarity	NPD3609	Approved
0.7901	Intermediate Similarity	NPD3610	Approved
0.7881	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2720	Phase 1
0.787	Intermediate Similarity	NPD3961	Discontinued
0.787	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD8431	Approved
0.7862	Intermediate Similarity	NPD3476	Approved
0.7862	Intermediate Similarity	NPD3475	Approved
0.7849	Intermediate Similarity	NPD1038	Approved
0.7824	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7948	Phase 1
0.7798	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1661	Suspended
0.7792	Intermediate Similarity	NPD4547	Phase 3
0.7785	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2119	Approved
0.7778	Intermediate Similarity	NPD2118	Approved
0.7764	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2006	Phase 2
0.7746	Intermediate Similarity	NPD802	Phase 2
0.7742	Intermediate Similarity	NPD2430	Phase 2
0.7727	Intermediate Similarity	NPD7469	Discontinued
0.7727	Intermediate Similarity	NPD1683	Approved
0.7725	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2580	Discontinued
0.7722	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1248	Discontinued
0.7708	Intermediate Similarity	NPD9583	Approved
0.7706	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6217	Discontinued
0.7703	Intermediate Similarity	NPD3385	Approved
0.7702	Intermediate Similarity	NPD5138	Approved
0.7702	Intermediate Similarity	NPD5140	Approved
0.7692	Intermediate Similarity	NPD3833	Phase 3
0.7692	Intermediate Similarity	NPD3835	Phase 3
0.7688	Intermediate Similarity	NPD3404	Approved
0.7684	Intermediate Similarity	NPD484	Approved
0.7677	Intermediate Similarity	NPD4702	Approved
0.7677	Intermediate Similarity	NPD4703	Approved
0.7669	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4638	Approved
0.7669	Intermediate Similarity	NPD4640	Approved
0.7669	Intermediate Similarity	NPD4639	Approved
0.7661	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5105	Approved
0.7633	Intermediate Similarity	NPD5106	Approved
0.7628	Intermediate Similarity	NPD1183	Approved
0.761	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD271	Approved
0.7606	Intermediate Similarity	NPD268	Approved
0.76	Intermediate Similarity	NPD7618	Phase 3
0.76	Intermediate Similarity	NPD7619	Phase 3
0.7586	Intermediate Similarity	NPD4615	Phase 2
0.7584	Intermediate Similarity	NPD4029	Approved
0.7584	Intermediate Similarity	NPD4030	Approved
0.7584	Intermediate Similarity	NPD4028	Approved
0.7576	Intermediate Similarity	NPD3117	Approved
0.7576	Intermediate Similarity	NPD3116	Approved
0.7574	Intermediate Similarity	NPD1895	Discontinued
0.7574	Intermediate Similarity	NPD1707	Approved
0.7574	Intermediate Similarity	NPD1708	Approved
0.7571	Intermediate Similarity	NPD9392	Approved
0.7571	Intermediate Similarity	NPD9396	Approved
0.7569	Intermediate Similarity	NPD9357	Approved
0.7566	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5021	Discontinued
0.7554	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD976	Approved
0.7547	Intermediate Similarity	NPD975	Approved
0.7547	Intermediate Similarity	NPD2165	Phase 1
0.7547	Intermediate Similarity	NPD977	Approved
0.7531	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5901	Discontinued
0.7514	Intermediate Similarity	NPD6664	Approved
0.75	Intermediate Similarity	NPD3113	Approved
0.75	Intermediate Similarity	NPD3115	Approved
0.75	Intermediate Similarity	NPD715	Phase 3
0.75	Intermediate Similarity	NPD706	Phase 1
0.75	Intermediate Similarity	NPD3112	Approved
0.75	Intermediate Similarity	NPD3114	Approved
0.7484	Intermediate Similarity	NPD3813	Approved
0.7484	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5020	Approved
0.7467	Intermediate Similarity	NPD3942	Approved
0.7467	Intermediate Similarity	NPD3944	Approved
0.7455	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD803	Phase 1
0.744	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD3825	Phase 3
0.7415	Intermediate Similarity	NPD1598	Discontinued
0.741	Intermediate Similarity	NPD5436	Phase 1
0.7407	Intermediate Similarity	NPD5255	Approved
0.7391	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1255	Approved
0.7368	Intermediate Similarity	NPD1254	Approved
0.7368	Intermediate Similarity	NPD1253	Approved
0.7368	Intermediate Similarity	NPD1256	Approved
0.7356	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4326	Phase 2
0.7342	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5315	Discontinued
0.7315	Intermediate Similarity	NPD947	Approved
0.7312	Intermediate Similarity	NPD6158	Phase 2
0.7312	Intermediate Similarity	NPD2882	Phase 1
0.7312	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8073	Approved
0.7308	Intermediate Similarity	NPD3717	Discontinued
0.7301	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD9080	Approved
0.7273	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8072	Approved
0.7268	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3339	Approved
0.7261	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD8386	Phase 2
0.7246	Intermediate Similarity	NPD2844	Phase 3
0.7244	Intermediate Similarity	NPD416	Approved
0.7241	Intermediate Similarity	NPD1227	Phase 2
0.7241	Intermediate Similarity	NPD9598	Discontinued
0.7235	Intermediate Similarity	NPD5100	Phase 3
0.7235	Intermediate Similarity	NPD2382	Approved
0.7235	Intermediate Similarity	NPD2381	Approved
0.7235	Intermediate Similarity	NPD2380	Approved
0.7234	Intermediate Similarity	NPD8093	Discontinued
0.7228	Intermediate Similarity	NPD8272	Phase 2

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