NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	243.1
Volume:	242.487
LogP:	0.85
LogD:	0.951
LogS:	-2.406
# Rotatable Bonds:	2
TPSA:	73.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	2.754
Fsp3:	0.231
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:	-4.877
MDCK Permeability:	7.98165456217248e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.24
20% Bioavailability (F20%):	0.073
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	35.438167572021484%
Volume Distribution (VD):	0.789
Pgp-substrate:	56.93099594116211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.125
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.223
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.103
CYP2C9-substrate:	0.503
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.412
CYP3A4-inhibitor:	0.165
CYP3A4-substrate:	0.089

ADMET: Excretion

Clearance (CL):	5.712
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.461
Maximum Recommended Daily Dose:	0.702
Skin Sensitization:	0.452
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.152

Download Data

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

Natural Product: NPC279918

Natural Product ID:	NPC279918
*Common Name:**	Cyclo(-Trp-Gly)
IUPAC Name:	(3S)-3-(1H-indol-3-ylmethyl)piperazine-2,5-dione
Synonyms:	Cyclo(-Trp-Gly)
Standard InCHIKey:	IFQZEERDQXQTLJ-NSHDSACASA-N
Standard InCHI:	InChI=1S/C13H13N3O2/c17-12-7-15-13(18)11(16-12)5-8-6-14-10-4-2-1-3-9(8)10/h1-4,6,11,14H,5,7H2,(H,15,18)(H,16,17)/t11-/m0/s1
SMILES:	OC1=N[C@H](C(=NC1)O)Cc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226544
PubChem CID:	6997508
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO30356	Talaromyces thermophilus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21967034]

☑ 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	3
Others	2

Activity Type	# Activity
Cell Line	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[489692]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	100000.0	nM	PMID[489692]
NPT27	Others	Unspecified		LogP app	=	-6.02	n.a.	PMID[489691]
NPT35	Others	n.a.		LogP	=	0.07	n.a.	PMID[489691]

☑ 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 NPC279918 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	433
0.1-0.2	4915
0.2-0.3	19551
0.3-0.4	10689
0.4-0.5	2959
0.5-0.6	2042
0.6-0.7	1321
0.7-0.8	576
0.8-0.85	130
0.85-0.9	66
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC282231
0.9735	High Similarity	NPC474561
0.9735	High Similarity	NPC49954
0.9735	High Similarity	NPC54988
0.9671	High Similarity	NPC63751
0.9474	High Similarity	NPC194640
0.9351	High Similarity	NPC160105
0.9304	High Similarity	NPC59269
0.9182	High Similarity	NPC248454
0.9139	High Similarity	NPC469760
0.9139	High Similarity	NPC259644
0.9139	High Similarity	NPC469786
0.9139	High Similarity	NPC73952
0.9139	High Similarity	NPC469765
0.9139	High Similarity	NPC25008
0.9139	High Similarity	NPC469763
0.9114	High Similarity	NPC314603
0.9085	High Similarity	NPC469762
0.9079	High Similarity	NPC75540
0.9079	High Similarity	NPC212376
0.9079	High Similarity	NPC80597
0.9079	High Similarity	NPC70922
0.9079	High Similarity	NPC211572
0.9057	High Similarity	NPC203468
0.9057	High Similarity	NPC149155
0.9057	High Similarity	NPC110500
0.9026	High Similarity	NPC230869
0.902	High Similarity	NPC469785
0.902	High Similarity	NPC285469
0.9	High Similarity	NPC267885
0.8993	High Similarity	NPC314372
0.8986	High Similarity	NPC190296
0.8957	High Similarity	NPC163055
0.8924	High Similarity	NPC78020
0.8889	High Similarity	NPC126709
0.8889	High Similarity	NPC248041
0.8889	High Similarity	NPC283219
0.8867	High Similarity	NPC159856
0.8854	High Similarity	NPC311276
0.8846	High Similarity	NPC131718
0.879	High Similarity	NPC16667
0.878	High Similarity	NPC233936
0.8735	High Similarity	NPC15102
0.871	High Similarity	NPC207726
0.8707	High Similarity	NPC96102
0.8688	High Similarity	NPC201700
0.8675	High Similarity	NPC165495
0.8649	High Similarity	NPC105127
0.8649	High Similarity	NPC84911
0.8647	High Similarity	NPC473342
0.8647	High Similarity	NPC477167
0.8636	High Similarity	NPC105818
0.8636	High Similarity	NPC24678
0.8627	High Similarity	NPC471957
0.8616	High Similarity	NPC40779
0.8616	High Similarity	NPC102423
0.8598	High Similarity	NPC14113
0.8598	High Similarity	NPC145885
0.8598	High Similarity	NPC84827
0.8581	High Similarity	NPC29886
0.8581	High Similarity	NPC261195
0.858	High Similarity	NPC321708
0.858	High Similarity	NPC470498
0.8571	High Similarity	NPC235684
0.8562	High Similarity	NPC143872
0.8545	High Similarity	NPC55772
0.8544	High Similarity	NPC67056
0.8535	High Similarity	NPC141353
0.8533	High Similarity	NPC110126
0.8533	High Similarity	NPC73767
0.8521	High Similarity	NPC317030
0.8521	High Similarity	NPC17059
0.8519	High Similarity	NPC280548
0.8519	High Similarity	NPC194411
0.8485	Intermediate Similarity	NPC111275
0.8485	Intermediate Similarity	NPC68354
0.8477	Intermediate Similarity	NPC469780
0.8477	Intermediate Similarity	NPC469779
0.8477	Intermediate Similarity	NPC469784
0.8477	Intermediate Similarity	NPC279081
0.8477	Intermediate Similarity	NPC469768
0.8477	Intermediate Similarity	NPC469767
0.8477	Intermediate Similarity	NPC469783
0.8477	Intermediate Similarity	NPC469761
0.8471	Intermediate Similarity	NPC213629
0.8462	Intermediate Similarity	NPC216713
0.8462	Intermediate Similarity	NPC474707
0.8452	Intermediate Similarity	NPC37548
0.8452	Intermediate Similarity	NPC228835
0.8435	Intermediate Similarity	NPC82295
0.8434	Intermediate Similarity	NPC213468
0.8434	Intermediate Similarity	NPC11126
0.8428	Intermediate Similarity	NPC135141
0.8428	Intermediate Similarity	NPC92796
0.8421	Intermediate Similarity	NPC469766
0.8412	Intermediate Similarity	NPC204565
0.8402	Intermediate Similarity	NPC163421
0.8402	Intermediate Similarity	NPC314002
0.8402	Intermediate Similarity	NPC188387
0.8393	Intermediate Similarity	NPC220765
0.8373	Intermediate Similarity	NPC151939
0.8364	Intermediate Similarity	NPC275305
0.8364	Intermediate Similarity	NPC37423
0.8363	Intermediate Similarity	NPC65215
0.8363	Intermediate Similarity	NPC173028
0.8355	Intermediate Similarity	NPC230002
0.8353	Intermediate Similarity	NPC94752
0.8343	Intermediate Similarity	NPC204717
0.8333	Intermediate Similarity	NPC470508
0.8333	Intermediate Similarity	NPC71037
0.8324	Intermediate Similarity	NPC304187
0.8324	Intermediate Similarity	NPC477166
0.8323	Intermediate Similarity	NPC288838
0.8314	Intermediate Similarity	NPC95783
0.8305	Intermediate Similarity	NPC470497
0.8304	Intermediate Similarity	NPC46580
0.8303	Intermediate Similarity	NPC313791
0.8295	Intermediate Similarity	NPC470499
0.8284	Intermediate Similarity	NPC48938
0.8274	Intermediate Similarity	NPC300688
0.8269	Intermediate Similarity	NPC469811
0.8263	Intermediate Similarity	NPC183662
0.8263	Intermediate Similarity	NPC217372
0.8263	Intermediate Similarity	NPC15573
0.825	Intermediate Similarity	NPC129721
0.8246	Intermediate Similarity	NPC62749
0.8246	Intermediate Similarity	NPC315555
0.8246	Intermediate Similarity	NPC171171
0.8243	Intermediate Similarity	NPC22079
0.8239	Intermediate Similarity	NPC38736
0.8239	Intermediate Similarity	NPC470507
0.8218	Intermediate Similarity	NPC99666
0.8217	Intermediate Similarity	NPC321911
0.8217	Intermediate Similarity	NPC187951
0.8214	Intermediate Similarity	NPC219336
0.8214	Intermediate Similarity	NPC176199
0.8214	Intermediate Similarity	NPC215795
0.8205	Intermediate Similarity	NPC63545
0.8199	Intermediate Similarity	NPC206819
0.8199	Intermediate Similarity	NPC318065
0.8194	Intermediate Similarity	NPC242556
0.8193	Intermediate Similarity	NPC34508
0.8182	Intermediate Similarity	NPC179701
0.8176	Intermediate Similarity	NPC200214
0.8176	Intermediate Similarity	NPC469358
0.8171	Intermediate Similarity	NPC474177
0.8171	Intermediate Similarity	NPC49217
0.8165	Intermediate Similarity	NPC53947
0.8155	Intermediate Similarity	NPC184964
0.8153	Intermediate Similarity	NPC201380
0.8153	Intermediate Similarity	NPC179787
0.8136	Intermediate Similarity	NPC262898
0.8125	Intermediate Similarity	NPC133366
0.8121	Intermediate Similarity	NPC317430
0.8101	Intermediate Similarity	NPC106771
0.8101	Intermediate Similarity	NPC205254
0.8101	Intermediate Similarity	NPC23420
0.8101	Intermediate Similarity	NPC303820
0.8092	Intermediate Similarity	NPC325252
0.809	Intermediate Similarity	NPC171317
0.809	Intermediate Similarity	NPC473640
0.8084	Intermediate Similarity	NPC472123
0.8079	Intermediate Similarity	NPC242209
0.8063	Intermediate Similarity	NPC325903
0.8056	Intermediate Similarity	NPC52909
0.8056	Intermediate Similarity	NPC475935
0.8056	Intermediate Similarity	NPC94211
0.8045	Intermediate Similarity	NPC293917
0.8045	Intermediate Similarity	NPC100321
0.8039	Intermediate Similarity	NPC125746
0.8037	Intermediate Similarity	NPC122141
0.8036	Intermediate Similarity	NPC472586
0.8034	Intermediate Similarity	NPC229332
0.8034	Intermediate Similarity	NPC227582
0.8034	Intermediate Similarity	NPC77555
0.8011	Intermediate Similarity	NPC193761
0.8011	Intermediate Similarity	NPC476874
0.8	Intermediate Similarity	NPC315491
0.8	Intermediate Similarity	NPC45459
0.8	Intermediate Similarity	NPC270009
0.8	Intermediate Similarity	NPC472443
0.8	Intermediate Similarity	NPC154339
0.8	Intermediate Similarity	NPC470823
0.7988	Intermediate Similarity	NPC288785
0.7987	Intermediate Similarity	NPC124005
0.7978	Intermediate Similarity	NPC11445
0.7977	Intermediate Similarity	NPC280290
0.7975	Intermediate Similarity	NPC56765
0.7975	Intermediate Similarity	NPC41257
0.7974	Intermediate Similarity	NPC218268
0.7966	Intermediate Similarity	NPC307963
0.7956	Intermediate Similarity	NPC475506
0.7953	Intermediate Similarity	NPC91179
0.795	Intermediate Similarity	NPC141926
0.7941	Intermediate Similarity	NPC96890
0.7933	Intermediate Similarity	NPC156704
0.7933	Intermediate Similarity	NPC272483
0.7929	Intermediate Similarity	NPC329688
0.7929	Intermediate Similarity	NPC189812
0.7921	Intermediate Similarity	NPC157828

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 NPC279918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	606
0.2-0.3	1051
0.3-0.4	1472
0.4-0.5	2625
0.5-0.6	2029
0.6-0.7	923
0.7-0.8	200
0.8-0.85	20
0.85-0.9	15
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD4184	Clinical (unspecified phase)
0.9057	High Similarity	NPD482	Approved
0.8951	High Similarity	NPD6595	Phase 3
0.8882	High Similarity	NPD749	Clinical (unspecified phase)
0.8727	High Similarity	NPD2095	Phase 2
0.8727	High Similarity	NPD2094	Phase 2
0.8727	High Similarity	NPD2092	Phase 2
0.8707	High Similarity	NPD198	Clinical (unspecified phase)
0.8675	High Similarity	NPD2096	Phase 2
0.8675	High Similarity	NPD2091	Phase 2
0.8658	High Similarity	NPD786	Approved
0.8642	High Similarity	NPD750	Phase 2
0.8631	High Similarity	NPD8431	Approved
0.8623	High Similarity	NPD6610	Clinical (unspecified phase)
0.8614	High Similarity	NPD5728	Clinical (unspecified phase)
0.8598	High Similarity	NPD6203	Clinical (unspecified phase)
0.8589	High Similarity	NPD5065	Approved
0.858	High Similarity	NPD8110	Clinical (unspecified phase)
0.8545	High Similarity	NPD4079	Approved
0.8545	High Similarity	NPD4076	Approved
0.8543	High Similarity	NPD1722	Approved
0.8485	Intermediate Similarity	NPD3505	Approved
0.8485	Intermediate Similarity	NPD2144	Approved
0.8485	Intermediate Similarity	NPD3506	Approved
0.8452	Intermediate Similarity	NPD3100	Discontinued
0.8452	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3038	Discontinued
0.8293	Intermediate Similarity	NPD1326	Approved
0.8293	Intermediate Similarity	NPD1325	Approved
0.8276	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7948	Phase 1
0.8144	Intermediate Similarity	NPD4128	Approved
0.8059	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2172	Phase 1
0.805	Intermediate Similarity	NPD4462	Approved
0.805	Intermediate Similarity	NPD4463	Approved
0.8045	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4640	Approved
0.8012	Intermediate Similarity	NPD4639	Approved
0.8012	Intermediate Similarity	NPD4638	Approved
0.8011	Intermediate Similarity	NPD8073	Approved
0.8	Intermediate Similarity	NPD8386	Phase 2
0.8	Intermediate Similarity	NPD484	Approved
0.7989	Intermediate Similarity	NPD3961	Discontinued
0.7988	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4075	Phase 2
0.7967	Intermediate Similarity	NPD8072	Approved
0.7966	Intermediate Similarity	NPD1038	Approved
0.7966	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2837	Discontinued
0.7927	Intermediate Similarity	NPD1403	Approved
0.7927	Intermediate Similarity	NPD1404	Approved
0.7925	Intermediate Similarity	NPD4702	Approved
0.7925	Intermediate Similarity	NPD4703	Approved
0.7923	Intermediate Similarity	NPD5901	Discontinued
0.7917	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7957	Phase 1
0.788	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4181	Approved
0.7834	Intermediate Similarity	NPD1592	Phase 3
0.7831	Intermediate Similarity	NPD3323	Discontinued
0.7826	Intermediate Similarity	NPD8272	Phase 2
0.78	Intermediate Similarity	NPD991	Phase 2
0.78	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2640	Approved
0.7798	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2641	Approved
0.7796	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD802	Phase 2
0.7738	Intermediate Similarity	NPD2639	Approved
0.7738	Intermediate Similarity	NPD2642	Approved
0.773	Intermediate Similarity	NPD5426	Phase 3
0.7727	Intermediate Similarity	NPD706	Phase 1
0.7713	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD3404	Approved
0.7702	Intermediate Similarity	NPD1661	Suspended
0.7679	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7470	Discontinued
0.7672	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8026	Phase 1
0.7665	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6217	Discontinued
0.7624	Intermediate Similarity	NPD7619	Phase 3
0.7624	Intermediate Similarity	NPD7618	Phase 3
0.7619	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3610	Approved
0.7602	Intermediate Similarity	NPD3609	Approved
0.7592	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD5100	Phase 3
0.7562	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7944	Discontinued
0.7516	Intermediate Similarity	NPD5254	Discontinued
0.7515	Intermediate Similarity	NPD5140	Approved
0.7515	Intermediate Similarity	NPD5138	Approved
0.7514	Intermediate Similarity	NPD2928	Phase 2
0.7514	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD5612	Discontinued
0.75	Intermediate Similarity	NPD4499	Approved
0.75	Intermediate Similarity	NPD5117	Phase 2
0.7486	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5021	Discontinued
0.7474	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1262	Discovery
0.746	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5106	Approved
0.7458	Intermediate Similarity	NPD5105	Approved
0.7457	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3717	Discontinued
0.7443	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5255	Approved
0.7436	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1683	Approved
0.7419	Intermediate Similarity	NPD3475	Approved
0.7419	Intermediate Similarity	NPD3476	Approved
0.741	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3813	Approved
0.7399	Intermediate Similarity	NPD3117	Approved
0.7399	Intermediate Similarity	NPD3116	Approved
0.7389	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD2844	Phase 3
0.7384	Intermediate Similarity	NPD5862	Discovery
0.7382	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4547	Phase 3
0.7371	Intermediate Similarity	NPD2380	Approved
0.7371	Intermediate Similarity	NPD2382	Approved
0.7371	Intermediate Similarity	NPD2381	Approved
0.7368	Intermediate Similarity	NPD1392	Approved
0.7358	Intermediate Similarity	NPD8093	Discontinued
0.7356	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3654	Approved
0.7351	Intermediate Similarity	NPD6664	Approved
0.7349	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6158	Phase 2
0.7346	Intermediate Similarity	NPD2006	Phase 2
0.7346	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2119	Approved
0.7338	Intermediate Similarity	NPD2118	Approved
0.7333	Intermediate Similarity	NPD2430	Phase 2
0.7333	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1183	Approved
0.7333	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD425	Approved
0.7326	Intermediate Similarity	NPD424	Approved
0.7321	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2580	Discontinued
0.7318	Intermediate Similarity	NPD6178	Phase 3
0.7317	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2896	Discontinued
0.7302	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7970	Approved
0.7278	Intermediate Similarity	NPD3385	Approved
0.7273	Intermediate Similarity	NPD3825	Phase 3
0.7268	Intermediate Similarity	NPD3330	Phase 1
0.7267	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2720	Phase 1
0.7267	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4601	Approved
0.7234	Intermediate Similarity	NPD4600	Approved
0.7232	Intermediate Similarity	NPD8123	Approved
0.7232	Intermediate Similarity	NPD8122	Approved
0.7231	Intermediate Similarity	NPD8094	Discontinued
0.7228	Intermediate Similarity	NPD4615	Phase 2
0.7225	Intermediate Similarity	NPD1248	Discontinued
0.7219	Intermediate Similarity	NPD3115	Approved
0.7219	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3113	Approved
0.7219	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3112	Approved
0.7219	Intermediate Similarity	NPD3114	Approved
0.7216	Intermediate Similarity	NPD5066	Phase 2
0.7216	Intermediate Similarity	NPD5067	Phase 2
0.7214	Intermediate Similarity	NPD7271	Approved
0.7213	Intermediate Similarity	NPD6281	Approved
0.7208	Intermediate Similarity	NPD5818	Discontinued
0.7207	Intermediate Similarity	NPD1895	Discontinued
0.7207	Intermediate Similarity	NPD3178	Discontinued
0.7196	Intermediate Similarity	NPD4511	Phase 1
0.7193	Intermediate Similarity	NPD9705	Discontinued

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