NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	257.12
Volume:	259.783
LogP:	1.192
LogD:	1.405
LogS:	-2.315
# 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:	0.741
Synthetic Accessibility Score:	2.992
Fsp3:	0.286
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:	-4.829
MDCK Permeability:	4.985170107829617e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	50.367637634277344%
Volume Distribution (VD):	0.698
Pgp-substrate:	40.85437774658203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.564
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.523
CYP3A4-inhibitor:	0.144
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	4.24
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.285
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.685
Skin Sensitization:	0.102
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC282231

Natural Product ID:	NPC282231
*Common Name:**	L-Alanyl-L-Tryptophan Anhydride
IUPAC Name:	(3S,6S)-3-(1H-indol-3-ylmethyl)-6-methylpiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	VDMMFAOUINDEGC-UFBFGSQYSA-N
Standard InCHI:	InChI=1S/C14H15N3O2/c1-8-13(18)17-12(14(19)16-8)6-9-7-15-11-5-3-2-4-10(9)11/h2-5,7-8,12,15H,6H2,1H3,(H,16,19)(H,17,18)/t8-,12-/m0/s1
SMILES:	OC1=N[C@@H](Cc2c[nH]c3c2cccc3)C(=N[C@H]1C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2031511
PubChem CID:	15563754
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
NPO32990	acrostalagmus luteoalbus scsio f457	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23079524]
NPO33384	0cardiopsis gilva YIM 90087	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23441911]
NPO32640	eurotium rubrum ma-150	Species	Aspergillaceae	Eukaryota	Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.	n.a.	n.a.	PMID[25730346]

☑ 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	7
LD50	1
Others	3

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	2
Organism	1

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[486668]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	100000.0	nM	PMID[486668]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[486669]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	100000.0	nM	PMID[486669]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[486669]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	100000.0	nM	PMID[486669]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	200000.0	nM	PMID[486671]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	54.6	%	PMID[486670]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	2.31	%	PMID[486671]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	25.5	uM	PMID[486672]

☑ 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 NPC282231 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	396
0.1-0.2	4198
0.2-0.3	19129
0.3-0.4	11752
0.4-0.5	2991
0.5-0.6	2084
0.6-0.7	1326
0.7-0.8	598
0.8-0.85	131
0.85-0.9	66
0.9-0.95	19
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC279918
0.9801	High Similarity	NPC49954
0.9801	High Similarity	NPC474561
0.9671	High Similarity	NPC54988
0.9608	High Similarity	NPC63751
0.9539	High Similarity	NPC194640
0.9416	High Similarity	NPC160105
0.9245	High Similarity	NPC59269
0.9245	High Similarity	NPC248454
0.9205	High Similarity	NPC469760
0.9205	High Similarity	NPC25008
0.9205	High Similarity	NPC469786
0.9205	High Similarity	NPC73952
0.9205	High Similarity	NPC259644
0.9205	High Similarity	NPC469763
0.9205	High Similarity	NPC469765
0.9177	High Similarity	NPC314603
0.9145	High Similarity	NPC70922
0.9145	High Similarity	NPC75540
0.9145	High Similarity	NPC212376
0.9145	High Similarity	NPC211572
0.9145	High Similarity	NPC80597
0.9085	High Similarity	NPC285469
0.9062	High Similarity	NPC267885
0.906	High Similarity	NPC314372
0.9054	High Similarity	NPC190296
0.9026	High Similarity	NPC469762
0.9018	High Similarity	NPC163055
0.9	High Similarity	NPC110500
0.9	High Similarity	NPC149155
0.9	High Similarity	NPC203468
0.8968	High Similarity	NPC230869
0.8961	High Similarity	NPC469785
0.8951	High Similarity	NPC248041
0.8951	High Similarity	NPC126709
0.8917	High Similarity	NPC311276
0.8868	High Similarity	NPC78020
0.8854	High Similarity	NPC16667
0.8841	High Similarity	NPC233936
0.8834	High Similarity	NPC283219
0.8808	High Similarity	NPC159856
0.879	High Similarity	NPC131718
0.8774	High Similarity	NPC207726
0.875	High Similarity	NPC201700
0.8735	High Similarity	NPC165495
0.8716	High Similarity	NPC84911
0.8701	High Similarity	NPC24678
0.8701	High Similarity	NPC105818
0.8693	High Similarity	NPC471957
0.8683	High Similarity	NPC15102
0.8679	High Similarity	NPC40779
0.8659	High Similarity	NPC84827
0.8659	High Similarity	NPC14113
0.8659	High Similarity	NPC145885
0.8649	High Similarity	NPC29886
0.8649	High Similarity	NPC96102
0.8649	High Similarity	NPC261195
0.8642	High Similarity	NPC470498
0.8631	High Similarity	NPC235684
0.8608	High Similarity	NPC67056
0.86	High Similarity	NPC73767
0.86	High Similarity	NPC110126
0.8596	High Similarity	NPC473342
0.8596	High Similarity	NPC477167
0.8591	High Similarity	NPC105127
0.858	High Similarity	NPC317030
0.858	High Similarity	NPC280548
0.858	High Similarity	NPC194411
0.8562	High Similarity	NPC102423
0.8545	High Similarity	NPC68354
0.8543	High Similarity	NPC469783
0.8543	High Similarity	NPC469767
0.8543	High Similarity	NPC469761
0.8543	High Similarity	NPC469784
0.8543	High Similarity	NPC469768
0.8543	High Similarity	NPC469779
0.8543	High Similarity	NPC469780
0.8529	High Similarity	NPC213629
0.8529	High Similarity	NPC321708
0.8521	High Similarity	NPC474707
0.8516	High Similarity	NPC37548
0.8512	High Similarity	NPC228835
0.8506	High Similarity	NPC143872
0.8494	Intermediate Similarity	NPC11126
0.8494	Intermediate Similarity	NPC55772
0.8494	Intermediate Similarity	NPC213468
0.8487	Intermediate Similarity	NPC469766
0.8481	Intermediate Similarity	NPC141353
0.8471	Intermediate Similarity	NPC204565
0.8471	Intermediate Similarity	NPC17059
0.8462	Intermediate Similarity	NPC188387
0.8462	Intermediate Similarity	NPC314002
0.8462	Intermediate Similarity	NPC163421
0.8434	Intermediate Similarity	NPC151939
0.8434	Intermediate Similarity	NPC111275
0.8424	Intermediate Similarity	NPC275305
0.8424	Intermediate Similarity	NPC37423
0.8421	Intermediate Similarity	NPC279081
0.8421	Intermediate Similarity	NPC65215
0.8421	Intermediate Similarity	NPC173028
0.8412	Intermediate Similarity	NPC94752
0.8408	Intermediate Similarity	NPC216713
0.8402	Intermediate Similarity	NPC204717
0.8395	Intermediate Similarity	NPC470508
0.8378	Intermediate Similarity	NPC82295
0.8375	Intermediate Similarity	NPC92796
0.8375	Intermediate Similarity	NPC135141
0.8372	Intermediate Similarity	NPC95783
0.8364	Intermediate Similarity	NPC313791
0.8362	Intermediate Similarity	NPC470497
0.8352	Intermediate Similarity	NPC470499
0.8343	Intermediate Similarity	NPC220765
0.8333	Intermediate Similarity	NPC300688
0.8313	Intermediate Similarity	NPC129721
0.8311	Intermediate Similarity	NPC22079
0.8304	Intermediate Similarity	NPC171171
0.8302	Intermediate Similarity	NPC38736
0.8302	Intermediate Similarity	NPC470507
0.8301	Intermediate Similarity	NPC230002
0.8284	Intermediate Similarity	NPC71037
0.828	Intermediate Similarity	NPC321911
0.828	Intermediate Similarity	NPC187951
0.8276	Intermediate Similarity	NPC304187
0.8276	Intermediate Similarity	NPC477166
0.8274	Intermediate Similarity	NPC215795
0.8274	Intermediate Similarity	NPC176199
0.8274	Intermediate Similarity	NPC219336
0.8269	Intermediate Similarity	NPC288838
0.8261	Intermediate Similarity	NPC206819
0.8261	Intermediate Similarity	NPC318065
0.8258	Intermediate Similarity	NPC242556
0.8256	Intermediate Similarity	NPC46580
0.8253	Intermediate Similarity	NPC34508
0.8239	Intermediate Similarity	NPC179701
0.8239	Intermediate Similarity	NPC200214
0.8235	Intermediate Similarity	NPC469358
0.8235	Intermediate Similarity	NPC48938
0.8232	Intermediate Similarity	NPC49217
0.8229	Intermediate Similarity	NPC474177
0.8228	Intermediate Similarity	NPC53947
0.8217	Intermediate Similarity	NPC201380
0.8217	Intermediate Similarity	NPC179787
0.8217	Intermediate Similarity	NPC469811
0.8214	Intermediate Similarity	NPC217372
0.8214	Intermediate Similarity	NPC183662
0.8214	Intermediate Similarity	NPC15573
0.8198	Intermediate Similarity	NPC315555
0.8198	Intermediate Similarity	NPC62749
0.8192	Intermediate Similarity	NPC262898
0.8182	Intermediate Similarity	NPC133366
0.8171	Intermediate Similarity	NPC99666
0.8158	Intermediate Similarity	NPC325252
0.8153	Intermediate Similarity	NPC63545
0.8146	Intermediate Similarity	NPC473640
0.8146	Intermediate Similarity	NPC171317
0.8144	Intermediate Similarity	NPC472123
0.8107	Intermediate Similarity	NPC184964
0.8101	Intermediate Similarity	NPC100321
0.8101	Intermediate Similarity	NPC293917
0.8095	Intermediate Similarity	NPC472586
0.809	Intermediate Similarity	NPC229332
0.809	Intermediate Similarity	NPC227582
0.8072	Intermediate Similarity	NPC317430
0.8066	Intermediate Similarity	NPC193761
0.8066	Intermediate Similarity	NPC476874
0.8063	Intermediate Similarity	NPC470823
0.8059	Intermediate Similarity	NPC270009
0.8059	Intermediate Similarity	NPC472443
0.8056	Intermediate Similarity	NPC23420
0.8056	Intermediate Similarity	NPC106771
0.8056	Intermediate Similarity	NPC205254
0.8056	Intermediate Similarity	NPC303820
0.805	Intermediate Similarity	NPC124005
0.8047	Intermediate Similarity	NPC288785
0.8037	Intermediate Similarity	NPC56765
0.8037	Intermediate Similarity	NPC41257
0.8035	Intermediate Similarity	NPC280290
0.8034	Intermediate Similarity	NPC242209
0.8034	Intermediate Similarity	NPC11445
0.8023	Intermediate Similarity	NPC307963
0.8012	Intermediate Similarity	NPC325903
0.8012	Intermediate Similarity	NPC141926
0.8012	Intermediate Similarity	NPC91179
0.8011	Intermediate Similarity	NPC52909
0.8011	Intermediate Similarity	NPC475506
0.8011	Intermediate Similarity	NPC94211
0.8011	Intermediate Similarity	NPC475935
0.7989	Intermediate Similarity	NPC272483
0.7989	Intermediate Similarity	NPC77555
0.7988	Intermediate Similarity	NPC329688
0.7988	Intermediate Similarity	NPC189812
0.7988	Intermediate Similarity	NPC122141
0.7987	Intermediate Similarity	NPC125746
0.7978	Intermediate Similarity	NPC195239
0.7978	Intermediate Similarity	NPC157828
0.7977	Intermediate Similarity	NPC284678
0.7975	Intermediate Similarity	NPC286427
0.7975	Intermediate Similarity	NPC236711
0.7974	Intermediate Similarity	NPC198988
0.7967	Intermediate Similarity	NPC155143

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 NPC282231 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	590
0.2-0.3	1035
0.3-0.4	1443
0.4-0.5	2621
0.5-0.6	2072
0.6-0.7	939
0.7-0.8	210
0.8-0.85	24
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9295	High Similarity	NPD4184	Clinical (unspecified phase)
0.9012	High Similarity	NPD6595	Phase 3
0.9	High Similarity	NPD482	Approved
0.8944	High Similarity	NPD749	Clinical (unspecified phase)
0.8725	High Similarity	NPD786	Approved
0.8704	High Similarity	NPD750	Phase 2
0.869	High Similarity	NPD8431	Approved
0.8683	High Similarity	NPD6610	Clinical (unspecified phase)
0.8675	High Similarity	NPD2095	Phase 2
0.8675	High Similarity	NPD2094	Phase 2
0.8675	High Similarity	NPD2092	Phase 2
0.8649	High Similarity	NPD198	Clinical (unspecified phase)
0.8639	High Similarity	NPD8110	Clinical (unspecified phase)
0.8623	High Similarity	NPD2096	Phase 2
0.8623	High Similarity	NPD2091	Phase 2
0.8606	High Similarity	NPD4076	Approved
0.8606	High Similarity	NPD4079	Approved
0.8563	High Similarity	NPD5728	Clinical (unspecified phase)
0.8545	High Similarity	NPD3505	Approved
0.8545	High Similarity	NPD6203	Clinical (unspecified phase)
0.8545	High Similarity	NPD3506	Approved
0.8545	High Similarity	NPD2144	Approved
0.8537	High Similarity	NPD5065	Approved
0.8516	High Similarity	NPD3100	Discontinued
0.8487	Intermediate Similarity	NPD1722	Approved
0.8397	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD3038	Discontinued
0.8354	Intermediate Similarity	NPD1325	Approved
0.8354	Intermediate Similarity	NPD1326	Approved
0.8293	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD4128	Approved
0.8192	Intermediate Similarity	NPD7948	Phase 1
0.8118	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2172	Phase 1
0.8113	Intermediate Similarity	NPD4463	Approved
0.8113	Intermediate Similarity	NPD4462	Approved
0.8101	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4640	Approved
0.8072	Intermediate Similarity	NPD4639	Approved
0.8072	Intermediate Similarity	NPD4638	Approved
0.8066	Intermediate Similarity	NPD8073	Approved
0.8059	Intermediate Similarity	NPD8386	Phase 2
0.8047	Intermediate Similarity	NPD4075	Phase 2
0.8047	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD3961	Discontinued
0.8023	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD1038	Approved
0.8022	Intermediate Similarity	NPD8072	Approved
0.7988	Intermediate Similarity	NPD1404	Approved
0.7988	Intermediate Similarity	NPD1403	Approved
0.7987	Intermediate Similarity	NPD4703	Approved
0.7987	Intermediate Similarity	NPD4702	Approved
0.7976	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD484	Approved
0.7935	Intermediate Similarity	NPD7957	Phase 1
0.7935	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2837	Discontinued
0.7898	Intermediate Similarity	NPD1592	Phase 3
0.7895	Intermediate Similarity	NPD4181	Approved
0.7892	Intermediate Similarity	NPD3323	Discontinued
0.7892	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD8272	Phase 2
0.788	Intermediate Similarity	NPD5901	Discontinued
0.7857	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2640	Approved
0.7857	Intermediate Similarity	NPD2641	Approved
0.7849	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD802	Phase 2
0.7798	Intermediate Similarity	NPD2639	Approved
0.7798	Intermediate Similarity	NPD2642	Approved
0.7766	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD991	Phase 2
0.7738	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8026	Phase 1
0.7725	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7470	Discontinued
0.7725	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5426	Phase 3
0.7684	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6217	Discontinued
0.7684	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD706	Phase 1
0.768	Intermediate Similarity	NPD7618	Phase 3
0.768	Intermediate Similarity	NPD7619	Phase 3
0.7667	Intermediate Similarity	NPD3404	Approved
0.7661	Intermediate Similarity	NPD3610	Approved
0.7661	Intermediate Similarity	NPD3609	Approved
0.7654	Intermediate Similarity	NPD1661	Suspended
0.7644	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5100	Phase 3
0.7625	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7944	Discontinued
0.7579	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5254	Discontinued
0.7574	Intermediate Similarity	NPD5138	Approved
0.7574	Intermediate Similarity	NPD5140	Approved
0.7571	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5117	Phase 2
0.7556	Intermediate Similarity	NPD4499	Approved
0.7544	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5021	Discontinued
0.7541	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3717	Discontinued
0.7514	Intermediate Similarity	NPD5105	Approved
0.7514	Intermediate Similarity	NPD5106	Approved
0.7513	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5255	Approved
0.7487	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1683	Approved
0.7484	Intermediate Similarity	NPD3476	Approved
0.7484	Intermediate Similarity	NPD3475	Approved
0.7474	Intermediate Similarity	NPD5612	Discontinued
0.7471	Intermediate Similarity	NPD2928	Phase 2
0.747	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3116	Approved
0.7457	Intermediate Similarity	NPD3117	Approved
0.7444	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2844	Phase 3
0.7439	Intermediate Similarity	NPD4547	Phase 3
0.7435	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1262	Discovery
0.7421	Intermediate Similarity	NPD1392	Approved
0.7419	Intermediate Similarity	NPD3654	Approved
0.7418	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6158	Phase 2
0.7409	Intermediate Similarity	NPD8093	Discontinued
0.7407	Intermediate Similarity	NPD2006	Phase 2
0.7405	Intermediate Similarity	NPD6664	Approved
0.7403	Intermediate Similarity	NPD2119	Approved
0.7403	Intermediate Similarity	NPD2118	Approved
0.7401	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2430	Phase 2
0.7389	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2580	Discontinued
0.7381	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3813	Approved
0.7342	Intermediate Similarity	NPD3385	Approved
0.7341	Intermediate Similarity	NPD5862	Discovery
0.734	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2381	Approved
0.733	Intermediate Similarity	NPD2380	Approved
0.733	Intermediate Similarity	NPD2382	Approved
0.731	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1183	Approved
0.7288	Intermediate Similarity	NPD8122	Approved
0.7288	Intermediate Similarity	NPD8123	Approved
0.7287	Intermediate Similarity	NPD4601	Approved
0.7287	Intermediate Similarity	NPD4600	Approved
0.7283	Intermediate Similarity	NPD425	Approved
0.7283	Intermediate Similarity	NPD4615	Phase 2
0.7283	Intermediate Similarity	NPD424	Approved
0.7283	Intermediate Similarity	NPD1248	Discontinued
0.7282	Intermediate Similarity	NPD8094	Discontinued
0.7278	Intermediate Similarity	NPD3114	Approved
0.7278	Intermediate Similarity	NPD3115	Approved
0.7278	Intermediate Similarity	NPD3113	Approved
0.7278	Intermediate Similarity	NPD6178	Phase 3
0.7278	Intermediate Similarity	NPD3112	Approved
0.7273	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6281	Approved
0.7268	Intermediate Similarity	NPD5066	Phase 2
0.7268	Intermediate Similarity	NPD5067	Phase 2
0.7267	Intermediate Similarity	NPD2896	Discontinued
0.7264	Intermediate Similarity	NPD7271	Approved
0.7263	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3178	Discontinued
0.7259	Intermediate Similarity	NPD5818	Discontinued
0.7249	Intermediate Similarity	NPD4511	Phase 1
0.7247	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7970	Approved
0.724	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD268	Approved
0.7237	Intermediate Similarity	NPD271	Approved
0.7237	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4326	Phase 2
0.7235	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3825	Phase 3

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