NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.07
Volume:	309.295
LogP:	-1.243
LogD:	0.274
LogS:	-3.128
# Rotatable Bonds:	0
TPSA:	66.5
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	7.547
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.45
MDCK Permeability:	1.9169336155755445e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.484
Human Intestinal Absorption (HIA):	0.56
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.661

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219
Plasma Protein Binding (PPB):	96.38636016845703%
Volume Distribution (VD):	0.667
Pgp-substrate:	2.1324689388275146%

ADMET: Metabolism

CYP1A2-inhibitor:	0.8
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.237
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.647

ADMET: Excretion

Clearance (CL):	1.498
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.995
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.905
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.393
Carcinogencity:	0.954
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC469358

Natural Product ID:	NPC469358
*Common Name:**	2-(1H-Indol-3-Yl)Ethyl 2-Hydroxypropanoate
IUPAC Name:	2-(1H-indol-3-yl)ethyl 2-hydroxypropanoate
Synonyms:
Standard InCHIKey:	MUTOFPPDTGUSPX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H15NO3/c1-9(15)13(16)17-7-6-10-8-14-12-5-3-2-4-11(10)12/h2-5,8-9,14-15H,6-7H2,1H3
SMILES:	O=C(C(O)C)OCCc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076766
PubChem CID:	46880982
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO2605	Pichia membranifaciens	Species	Pichiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943625]
NPO2605	Pichia membranifaciens	Species	Pichiaceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	33.0	%	PMID[521558]

☑ 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 NPC469358 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	215
0.1-0.2	1627
0.2-0.3	13283
0.3-0.4	18728
0.4-0.5	4309
0.5-0.6	2083
0.6-0.7	1798
0.7-0.8	576
0.8-0.85	62
0.85-0.9	9
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9349	High Similarity	NPC315555
0.9112	High Similarity	NPC71037
0.8896	High Similarity	NPC230869
0.8736	High Similarity	NPC188387
0.8736	High Similarity	NPC163421
0.8713	High Similarity	NPC111275
0.8623	High Similarity	NPC311276
0.8623	High Similarity	NPC40779
0.8603	High Similarity	NPC267343
0.858	High Similarity	NPC78020
0.8555	High Similarity	NPC55772
0.8539	High Similarity	NPC154339
0.8449	Intermediate Similarity	NPC88008
0.8439	Intermediate Similarity	NPC267885
0.8402	Intermediate Similarity	NPC102423
0.8383	Intermediate Similarity	NPC469762
0.8382	Intermediate Similarity	NPC110500
0.8382	Intermediate Similarity	NPC149155
0.8382	Intermediate Similarity	NPC203468
0.8343	Intermediate Similarity	NPC248041
0.8343	Intermediate Similarity	NPC126709
0.8323	Intermediate Similarity	NPC469785
0.8304	Intermediate Similarity	NPC54988
0.8268	Intermediate Similarity	NPC235684
0.8239	Intermediate Similarity	NPC283219
0.8235	Intermediate Similarity	NPC476874
0.8235	Intermediate Similarity	NPC282231
0.8235	Intermediate Similarity	NPC193761
0.8226	Intermediate Similarity	NPC470497
0.8218	Intermediate Similarity	NPC313791
0.8216	Intermediate Similarity	NPC470499
0.8204	Intermediate Similarity	NPC259644
0.8204	Intermediate Similarity	NPC469763
0.8204	Intermediate Similarity	NPC25008
0.8204	Intermediate Similarity	NPC73952
0.8204	Intermediate Similarity	NPC469765
0.8204	Intermediate Similarity	NPC469786
0.8204	Intermediate Similarity	NPC469760
0.8197	Intermediate Similarity	NPC88315
0.8182	Intermediate Similarity	NPC145885
0.8182	Intermediate Similarity	NPC84827
0.8182	Intermediate Similarity	NPC14113
0.8176	Intermediate Similarity	NPC131718
0.8176	Intermediate Similarity	NPC279918
0.8161	Intermediate Similarity	NPC470498
0.816	Intermediate Similarity	NPC190296
0.8155	Intermediate Similarity	NPC75540
0.8155	Intermediate Similarity	NPC212376
0.8155	Intermediate Similarity	NPC70922
0.8155	Intermediate Similarity	NPC211572
0.8155	Intermediate Similarity	NPC80597
0.8136	Intermediate Similarity	NPC213468
0.8111	Intermediate Similarity	NPC62510
0.8092	Intermediate Similarity	NPC474561
0.8092	Intermediate Similarity	NPC49954
0.8092	Intermediate Similarity	NPC160105
0.8079	Intermediate Similarity	NPC151939
0.8066	Intermediate Similarity	NPC62749
0.8061	Intermediate Similarity	NPC314372
0.8046	Intermediate Similarity	NPC201700
0.8033	Intermediate Similarity	NPC95783
0.8011	Intermediate Similarity	NPC251090
0.7989	Intermediate Similarity	NPC138370
0.7968	Intermediate Similarity	NPC156704
0.7959	Intermediate Similarity	NPC313640
0.7952	Intermediate Similarity	NPC159856
0.7944	Intermediate Similarity	NPC233936
0.7943	Intermediate Similarity	NPC63751
0.7937	Intermediate Similarity	NPC213308
0.7935	Intermediate Similarity	NPC83111
0.7926	Intermediate Similarity	NPC67288
0.7923	Intermediate Similarity	NPC278434
0.7912	Intermediate Similarity	NPC314002
0.791	Intermediate Similarity	NPC314603
0.7901	Intermediate Similarity	NPC163055
0.7901	Intermediate Similarity	NPC261195
0.7901	Intermediate Similarity	NPC29886
0.7889	Intermediate Similarity	NPC300688
0.788	Intermediate Similarity	NPC321708
0.7874	Intermediate Similarity	NPC194640
0.787	Intermediate Similarity	NPC24678
0.787	Intermediate Similarity	NPC105818
0.7857	Intermediate Similarity	NPC471957
0.7857	Intermediate Similarity	NPC204717
0.7853	Intermediate Similarity	NPC84911
0.7842	Intermediate Similarity	NPC315491
0.7842	Intermediate Similarity	NPC45459
0.7833	Intermediate Similarity	NPC141377
0.7831	Intermediate Similarity	NPC149708
0.7826	Intermediate Similarity	NPC46580
0.7817	Intermediate Similarity	NPC229348
0.7814	Intermediate Similarity	NPC280290
0.7811	Intermediate Similarity	NPC2395
0.7807	Intermediate Similarity	NPC307963
0.7802	Intermediate Similarity	NPC472444
0.7802	Intermediate Similarity	NPC220765
0.7795	Intermediate Similarity	NPC478158
0.7791	Intermediate Similarity	NPC96102
0.7784	Intermediate Similarity	NPC323927
0.7778	Intermediate Similarity	NPC478157
0.7778	Intermediate Similarity	NPC227582
0.7778	Intermediate Similarity	NPC248454
0.7772	Intermediate Similarity	NPC171171
0.7765	Intermediate Similarity	NPC472586
0.7758	Intermediate Similarity	NPC110126
0.7758	Intermediate Similarity	NPC73767
0.7747	Intermediate Similarity	NPC275292
0.7747	Intermediate Similarity	NPC243381
0.7744	Intermediate Similarity	NPC314957
0.7744	Intermediate Similarity	NPC105127
0.774	Intermediate Similarity	NPC317430
0.7735	Intermediate Similarity	NPC472443
0.7735	Intermediate Similarity	NPC219336
0.773	Intermediate Similarity	NPC317030
0.7725	Intermediate Similarity	NPC179701
0.7717	Intermediate Similarity	NPC15102
0.7711	Intermediate Similarity	NPC469779
0.7711	Intermediate Similarity	NPC469780
0.7711	Intermediate Similarity	NPC469768
0.7711	Intermediate Similarity	NPC469783
0.7711	Intermediate Similarity	NPC469784
0.7711	Intermediate Similarity	NPC469767
0.7711	Intermediate Similarity	NPC469761
0.7708	Intermediate Similarity	NPC475506
0.7696	Intermediate Similarity	NPC74413
0.7696	Intermediate Similarity	NPC293917
0.7696	Intermediate Similarity	NPC100321
0.7696	Intermediate Similarity	NPC235885
0.7692	Intermediate Similarity	NPC46225
0.7692	Intermediate Similarity	NPC225821
0.7692	Intermediate Similarity	NPC469896
0.7688	Intermediate Similarity	NPC213629
0.7688	Intermediate Similarity	NPC474412
0.7688	Intermediate Similarity	NPC175474
0.7688	Intermediate Similarity	NPC296527
0.7684	Intermediate Similarity	NPC262898
0.7684	Intermediate Similarity	NPC272483
0.768	Intermediate Similarity	NPC217372
0.768	Intermediate Similarity	NPC183662
0.768	Intermediate Similarity	NPC59269
0.768	Intermediate Similarity	NPC15573
0.768	Intermediate Similarity	NPC184964
0.7677	Intermediate Similarity	NPC87856
0.7677	Intermediate Similarity	NPC219087
0.7677	Intermediate Similarity	NPC151976
0.7677	Intermediate Similarity	NPC207020
0.7676	Intermediate Similarity	NPC474707
0.7668	Intermediate Similarity	NPC260900
0.7668	Intermediate Similarity	NPC155143
0.7665	Intermediate Similarity	NPC469766
0.7662	Intermediate Similarity	NPC281049
0.7656	Intermediate Similarity	NPC252338
0.7654	Intermediate Similarity	NPC82295
0.7653	Intermediate Similarity	NPC127677
0.7653	Intermediate Similarity	NPC258062
0.7647	Intermediate Similarity	NPC76748
0.7644	Intermediate Similarity	NPC131887
0.7644	Intermediate Similarity	NPC473640
0.7638	Intermediate Similarity	NPC54744
0.7637	Intermediate Similarity	NPC276540
0.7637	Intermediate Similarity	NPC233050
0.7634	Intermediate Similarity	NPC204565
0.7629	Intermediate Similarity	NPC98715
0.7619	Intermediate Similarity	NPC106937
0.7619	Intermediate Similarity	NPC474177
0.7617	Intermediate Similarity	NPC300183
0.7616	Intermediate Similarity	NPC216713
0.7612	Intermediate Similarity	NPC472285
0.7609	Intermediate Similarity	NPC48938
0.7609	Intermediate Similarity	NPC472108
0.7609	Intermediate Similarity	NPC139291
0.7608	Intermediate Similarity	NPC323752
0.7606	Intermediate Similarity	NPC92111
0.7605	Intermediate Similarity	NPC279081
0.7594	Intermediate Similarity	NPC65215
0.7594	Intermediate Similarity	NPC173028
0.7586	Intermediate Similarity	NPC285469
0.7582	Intermediate Similarity	NPC96890
0.7582	Intermediate Similarity	NPC68354
0.7581	Intermediate Similarity	NPC94752
0.7572	Intermediate Similarity	NPC200214
0.7569	Intermediate Similarity	NPC275305
0.7569	Intermediate Similarity	NPC329688
0.7569	Intermediate Similarity	NPC189812
0.7569	Intermediate Similarity	NPC37423
0.7568	Intermediate Similarity	NPC165495
0.7566	Intermediate Similarity	NPC99666
0.7566	Intermediate Similarity	NPC67551
0.7562	Intermediate Similarity	NPC132211
0.7562	Intermediate Similarity	NPC203614
0.7562	Intermediate Similarity	NPC204491
0.756	Intermediate Similarity	NPC89987
0.7554	Intermediate Similarity	NPC314394
0.7541	Intermediate Similarity	NPC270009
0.7539	Intermediate Similarity	NPC13880
0.7528	Intermediate Similarity	NPC42372
0.7514	Intermediate Similarity	NPC472110
0.7514	Intermediate Similarity	NPC34508
0.7514	Intermediate Similarity	NPC472109
0.7514	Intermediate Similarity	NPC19679

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 NPC469358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	542
0.2-0.3	895
0.3-0.4	1495
0.4-0.5	2899
0.5-0.6	2195
0.6-0.7	830
0.7-0.8	136
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
0.8439	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD482	Approved
0.8202	Intermediate Similarity	NPD2092	Phase 2
0.8202	Intermediate Similarity	NPD2094	Phase 2
0.8202	Intermediate Similarity	NPD2095	Phase 2
0.8156	Intermediate Similarity	NPD2096	Phase 2
0.8156	Intermediate Similarity	NPD2091	Phase 2
0.8114	Intermediate Similarity	NPD750	Phase 2
0.8	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD2144	Approved
0.7917	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD6595	Phase 3
0.7876	Intermediate Similarity	NPD1392	Approved
0.7845	Intermediate Similarity	NPD3038	Discontinued
0.7842	Intermediate Similarity	NPD484	Approved
0.7824	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7957	Phase 1
0.7807	Intermediate Similarity	NPD1038	Approved
0.7791	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD786	Approved
0.7744	Intermediate Similarity	NPD2510	Approved
0.7744	Intermediate Similarity	NPD2509	Approved
0.772	Intermediate Similarity	NPD8072	Approved
0.7696	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD8073	Approved
0.7667	Intermediate Similarity	NPD5065	Approved
0.7653	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4076	Approved
0.7637	Intermediate Similarity	NPD4079	Approved
0.7629	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7470	Discontinued
0.7619	Intermediate Similarity	NPD802	Phase 2
0.759	Intermediate Similarity	NPD5901	Discontinued
0.7582	Intermediate Similarity	NPD3506	Approved
0.7582	Intermediate Similarity	NPD3505	Approved
0.756	Intermediate Similarity	NPD1722	Approved
0.7551	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD2844	Phase 3
0.7538	Intermediate Similarity	NPD5067	Phase 2
0.7538	Intermediate Similarity	NPD5066	Phase 2
0.7526	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD1768	Approved
0.7512	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1325	Approved
0.75	Intermediate Similarity	NPD5003	Discontinued
0.75	Intermediate Similarity	NPD1326	Approved
0.7486	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4601	Approved
0.7474	Intermediate Similarity	NPD4600	Approved
0.7462	Intermediate Similarity	NPD3003	Approved
0.7447	Intermediate Similarity	NPD8431	Approved
0.7435	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5426	Phase 3
0.7411	Intermediate Similarity	NPD8272	Phase 2
0.7407	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3100	Discontinued
0.7391	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3389	Approved
0.7389	Intermediate Similarity	NPD5612	Discontinued
0.7389	Intermediate Similarity	NPD3393	Approved
0.7389	Intermediate Similarity	NPD3394	Approved
0.7368	Intermediate Similarity	NPD2564	Approved
0.7368	Intermediate Similarity	NPD2565	Phase 2
0.7368	Intermediate Similarity	NPD4499	Approved
0.7356	Intermediate Similarity	NPD2172	Phase 1
0.7353	Intermediate Similarity	NPD1592	Phase 3
0.7333	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6987	Phase 1
0.732	Intermediate Similarity	NPD7948	Phase 1
0.7313	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4602	Approved
0.7299	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7001	Phase 3
0.7286	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3178	Discontinued
0.7268	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1404	Approved
0.7263	Intermediate Similarity	NPD1403	Approved
0.7258	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4463	Approved
0.7257	Intermediate Similarity	NPD4462	Approved
0.7245	Intermediate Similarity	NPD6248	Phase 2
0.7245	Intermediate Similarity	NPD6249	Phase 2
0.7243	Intermediate Similarity	NPD4075	Phase 2
0.7241	Intermediate Similarity	NPD4702	Approved
0.7241	Intermediate Similarity	NPD4703	Approved
0.7234	Intermediate Similarity	NPD5596	Phase 2
0.7228	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1534	Approved
0.7216	Intermediate Similarity	NPD4427	Phase 2
0.7216	Intermediate Similarity	NPD7944	Discontinued
0.7209	Intermediate Similarity	NPD4454	Phase 2
0.7208	Intermediate Similarity	NPD4500	Approved
0.7208	Intermediate Similarity	NPD4501	Approved
0.7206	Intermediate Similarity	NPD3794	Approved
0.7206	Intermediate Similarity	NPD3795	Approved
0.7196	Intermediate Similarity	NPD7558	Phase 2
0.7186	Intermediate Similarity	NPD5487	Phase 1
0.7186	Intermediate Similarity	NPD6176	Phase 1
0.7171	Intermediate Similarity	NPD5902	Approved
0.7171	Intermediate Similarity	NPD5903	Approved
0.7158	Intermediate Similarity	NPD4639	Approved
0.7158	Intermediate Similarity	NPD4638	Approved
0.7158	Intermediate Similarity	NPD4640	Approved
0.7157	Intermediate Similarity	NPD3825	Phase 3
0.7157	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3947	Discontinued
0.7143	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7234	Approved
0.7135	Intermediate Similarity	NPD7233	Approved
0.7128	Intermediate Similarity	NPD5899	Approved
0.7128	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5898	Approved
0.7128	Intermediate Similarity	NPD5897	Approved
0.7121	Intermediate Similarity	NPD6479	Discontinued
0.7109	Intermediate Similarity	NPD7271	Approved
0.7105	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2642	Approved
0.7104	Intermediate Similarity	NPD2639	Approved
0.7097	Intermediate Similarity	NPD4128	Approved
0.7092	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5140	Approved
0.7088	Intermediate Similarity	NPD5138	Approved
0.7085	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3390	Phase 2
0.7083	Intermediate Similarity	NPD3961	Discontinued
0.7079	Intermediate Similarity	NPD2837	Discontinued
0.7079	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2896	Discontinued
0.7067	Intermediate Similarity	NPD5632	Approved
0.7065	Intermediate Similarity	NPD2641	Approved
0.7065	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD2640	Approved
0.7062	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5913	Phase 3
0.7059	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6206	Phase 1
0.7044	Intermediate Similarity	NPD2187	Approved
0.7044	Intermediate Similarity	NPD2189	Approved
0.7042	Intermediate Similarity	NPD7730	Approved
0.7042	Intermediate Similarity	NPD7731	Approved
0.7039	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3404	Approved
0.7021	Intermediate Similarity	NPD4181	Approved
0.7016	Intermediate Similarity	NPD6178	Phase 3
0.701	Intermediate Similarity	NPD6281	Approved
0.7	Intermediate Similarity	NPD6242	Discontinued
0.6995	Remote Similarity	NPD6635	Approved
0.6995	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7711	Discontinued
0.6995	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3323	Discontinued
0.699	Remote Similarity	NPD8093	Discontinued
0.6986	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6999	Discontinued
0.6985	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8386	Phase 2
0.6977	Remote Similarity	NPD7824	Approved
0.6974	Remote Similarity	NPD4699	Discontinued
0.6974	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5862	Discovery
0.6968	Remote Similarity	NPD2382	Approved
0.6968	Remote Similarity	NPD2381	Approved
0.6968	Remote Similarity	NPD2380	Approved
0.6961	Remote Similarity	NPD2582	Approved
0.6961	Remote Similarity	NPD2581	Approved
0.6957	Remote Similarity	NPD8094	Discontinued
0.6955	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7618	Phase 3
0.6954	Remote Similarity	NPD7619	Phase 3
0.6947	Remote Similarity	NPD6452	Discontinued
0.6944	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.694	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7777	Approved
0.6935	Remote Similarity	NPD7778	Approved
0.6935	Remote Similarity	NPD53	Approved
0.6931	Remote Similarity	NPD2920	Discontinued
0.6931	Remote Similarity	NPD8123	Approved
0.6931	Remote Similarity	NPD8122	Approved
0.693	Remote Similarity	NPD5559	Phase 2
0.6927	Remote Similarity	NPD4506	Discontinued
0.6923	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7970	Approved
0.6919	Remote Similarity	NPD5611	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