NPASS Compound

Structure

CID63751 OpenBabel06191715402D 25 28 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7988 -3.0657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4679 -2.3226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8206 -2.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1589 -1.3715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -0.2976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 11 1 1 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 22 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	333.15
Volume:	347.093
LogP:	2.769
LogD:	3.174
LogS:	-3.731
# Rotatable Bonds:	4
TPSA:	73.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	2.87
Fsp3:	0.2
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:	-4.69
MDCK Permeability:	2.731009226408787e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.226
Plasma Protein Binding (PPB):	94.1964340209961%
Volume Distribution (VD):	0.623
Pgp-substrate:	8.079401016235352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.33
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.678
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.477
CYP2D6-substrate:	0.796
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	4.001
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.268
Human Hepatotoxicity (H-HT):	0.394
Drug-inuced Liver Injury (DILI):	0.415
AMES Toxicity:	0.697
Rat Oral Acute Toxicity:	0.779
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.204
Carcinogencity:	0.118
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.121

Download Data

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

Natural Product: NPC63751

Natural Product ID:	NPC63751
*Common Name:**	(3S,6S)-3-Benzyl-6-(1H-Indol-3-Ylmethyl)Piperazine-2,5-Dione
IUPAC Name:	(3S,6S)-3-benzyl-6-(1H-indol-3-ylmethyl)piperazine-2,5-dione
Synonyms:
Standard InCHIKey:	CUVKAUWOMPJEMI-ROUUACIJSA-N
Standard InCHI:	InChI=1S/C20H19N3O2/c24-19-17(10-13-6-2-1-3-7-13)22-20(25)18(23-19)11-14-12-21-16-9-5-4-8-15(14)16/h1-9,12,17-18,21H,10-11H2,(H,22,25)(H,23,24)/t17-,18-/m0/s1
SMILES:	OC1=N[C@@H](Cc2ccccc2)C(=N[C@H]1Cc1c[nH]c2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL190059
PubChem CID:	7408486
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
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]

☑ 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	1
Potency	2

Activity Type	# Activity
Cell Line	3
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3579	Individual Protein	Calpain 1	Homo sapiens	Inhibition	=	0.0	%	PMID[501451]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[501453]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[501454]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	100000.0	nM	PMID[501454]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[501453]

☑ 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 NPC63751 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	441
0.1-0.2	4326
0.2-0.3	18090
0.3-0.4	12615
0.4-0.5	2985
0.5-0.6	2036
0.6-0.7	1332
0.7-0.8	665
0.8-0.85	140
0.85-0.9	57
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC474561
0.9675	High Similarity	NPC49954
0.9671	High Similarity	NPC279918
0.962	High Similarity	NPC59269
0.9608	High Similarity	NPC282231
0.9423	High Similarity	NPC54988
0.9419	High Similarity	NPC194640
0.9299	High Similarity	NPC160105
0.9136	High Similarity	NPC248454
0.9091	High Similarity	NPC469763
0.9091	High Similarity	NPC73952
0.9091	High Similarity	NPC469765
0.9091	High Similarity	NPC259644
0.9091	High Similarity	NPC25008
0.9091	High Similarity	NPC469760
0.9091	High Similarity	NPC469786
0.9068	High Similarity	NPC314603
0.9038	High Similarity	NPC469762
0.9036	High Similarity	NPC15102
0.9032	High Similarity	NPC80597
0.9032	High Similarity	NPC70922
0.9032	High Similarity	NPC75540
0.9032	High Similarity	NPC212376
0.9032	High Similarity	NPC211572
0.8974	High Similarity	NPC285469
0.8974	High Similarity	NPC469785
0.8916	High Similarity	NPC163055
0.8824	High Similarity	NPC314372
0.8812	High Similarity	NPC311276
0.878	High Similarity	NPC110500
0.878	High Similarity	NPC149155
0.878	High Similarity	NPC203468
0.8765	High Similarity	NPC321708
0.8765	High Similarity	NPC201700
0.875	High Similarity	NPC16667
0.8743	High Similarity	NPC233936
0.8742	High Similarity	NPC230869
0.8727	High Similarity	NPC267885
0.8712	High Similarity	NPC194411
0.8693	High Similarity	NPC190296
0.8675	High Similarity	NPC68354
0.8671	High Similarity	NPC207726
0.865	High Similarity	NPC78020
0.8639	High Similarity	NPC165495
0.8625	High Similarity	NPC135141
0.8625	High Similarity	NPC92796
0.8623	High Similarity	NPC283219
0.8623	High Similarity	NPC126709
0.8623	High Similarity	NPC248041
0.8613	High Similarity	NPC477167
0.8613	High Similarity	NPC473342
0.8599	High Similarity	NPC24678
0.8599	High Similarity	NPC105818
0.8581	High Similarity	NPC159856
0.858	High Similarity	NPC40779
0.8571	High Similarity	NPC131718
0.8563	High Similarity	NPC151939
0.8554	High Similarity	NPC37423
0.8554	High Similarity	NPC275305
0.8538	High Similarity	NPC94752
0.8538	High Similarity	NPC235684
0.8512	High Similarity	NPC213468
0.8509	High Similarity	NPC67056
0.8497	Intermediate Similarity	NPC95783
0.8488	Intermediate Similarity	NPC17059
0.8488	Intermediate Similarity	NPC317030
0.8485	Intermediate Similarity	NPC280548
0.8462	Intermediate Similarity	NPC300688
0.8452	Intermediate Similarity	NPC145885
0.8452	Intermediate Similarity	NPC84827
0.8452	Intermediate Similarity	NPC14113
0.8442	Intermediate Similarity	NPC469779
0.8442	Intermediate Similarity	NPC469767
0.8442	Intermediate Similarity	NPC469783
0.8442	Intermediate Similarity	NPC469780
0.8442	Intermediate Similarity	NPC469761
0.8442	Intermediate Similarity	NPC469768
0.8442	Intermediate Similarity	NPC469784
0.8439	Intermediate Similarity	NPC213629
0.843	Intermediate Similarity	NPC474707
0.8421	Intermediate Similarity	NPC96102
0.8421	Intermediate Similarity	NPC228835
0.8418	Intermediate Similarity	NPC37548
0.8408	Intermediate Similarity	NPC288838
0.8402	Intermediate Similarity	NPC215795
0.8402	Intermediate Similarity	NPC176199
0.84	Intermediate Similarity	NPC99666
0.8395	Intermediate Similarity	NPC318065
0.8395	Intermediate Similarity	NPC206819
0.8387	Intermediate Similarity	NPC469766
0.8382	Intermediate Similarity	NPC204565
0.838	Intermediate Similarity	NPC205254
0.838	Intermediate Similarity	NPC106771
0.838	Intermediate Similarity	NPC23420
0.838	Intermediate Similarity	NPC303820
0.8377	Intermediate Similarity	NPC73767
0.8366	Intermediate Similarity	NPC84911
0.8366	Intermediate Similarity	NPC105127
0.8365	Intermediate Similarity	NPC53947
0.8354	Intermediate Similarity	NPC471957
0.8354	Intermediate Similarity	NPC102423
0.8333	Intermediate Similarity	NPC52909
0.8333	Intermediate Similarity	NPC94211
0.8333	Intermediate Similarity	NPC173028
0.8333	Intermediate Similarity	NPC65215
0.8333	Intermediate Similarity	NPC475935
0.8323	Intermediate Similarity	NPC470498
0.8315	Intermediate Similarity	NPC227582
0.8303	Intermediate Similarity	NPC470508
0.8301	Intermediate Similarity	NPC29886
0.8301	Intermediate Similarity	NPC261195
0.8295	Intermediate Similarity	NPC477166
0.8295	Intermediate Similarity	NPC304187
0.8294	Intermediate Similarity	NPC11126
0.8294	Intermediate Similarity	NPC55772
0.8291	Intermediate Similarity	NPC143872
0.8287	Intermediate Similarity	NPC193761
0.8272	Intermediate Similarity	NPC141353
0.8268	Intermediate Similarity	NPC470499
0.8261	Intermediate Similarity	NPC325903
0.8258	Intermediate Similarity	NPC110126
0.8235	Intermediate Similarity	NPC111275
0.8221	Intermediate Similarity	NPC129721
0.8221	Intermediate Similarity	NPC216643
0.821	Intermediate Similarity	NPC470507
0.821	Intermediate Similarity	NPC38736
0.8205	Intermediate Similarity	NPC279081
0.8204	Intermediate Similarity	NPC317430
0.8199	Intermediate Similarity	NPC216713
0.8198	Intermediate Similarity	NPC71037
0.8187	Intermediate Similarity	NPC187951
0.8187	Intermediate Similarity	NPC476874
0.8177	Intermediate Similarity	NPC470497
0.8177	Intermediate Similarity	NPC252338
0.8171	Intermediate Similarity	NPC41257
0.8171	Intermediate Similarity	NPC56765
0.8166	Intermediate Similarity	NPC34508
0.8166	Intermediate Similarity	NPC472123
0.8166	Intermediate Similarity	NPC313791
0.8165	Intermediate Similarity	NPC242556
0.8161	Intermediate Similarity	NPC314002
0.8161	Intermediate Similarity	NPC163421
0.8161	Intermediate Similarity	NPC188387
0.8158	Intermediate Similarity	NPC82295
0.815	Intermediate Similarity	NPC48938
0.815	Intermediate Similarity	NPC220765
0.8146	Intermediate Similarity	NPC474177
0.8128	Intermediate Similarity	NPC72956
0.8125	Intermediate Similarity	NPC469811
0.8118	Intermediate Similarity	NPC329688
0.8118	Intermediate Similarity	NPC189812
0.8114	Intermediate Similarity	NPC62749
0.8114	Intermediate Similarity	NPC171171
0.8111	Intermediate Similarity	NPC77555
0.8111	Intermediate Similarity	NPC229332
0.811	Intermediate Similarity	NPC286427
0.8108	Intermediate Similarity	NPC323927
0.8103	Intermediate Similarity	NPC204717
0.8101	Intermediate Similarity	NPC133366
0.8089	Intermediate Similarity	NPC230002
0.8085	Intermediate Similarity	NPC153980
0.8085	Intermediate Similarity	NPC6865
0.8075	Intermediate Similarity	NPC321911
0.8068	Intermediate Similarity	NPC46580
0.8066	Intermediate Similarity	NPC171317
0.8066	Intermediate Similarity	NPC473640
0.8063	Intermediate Similarity	NPC63545
0.8037	Intermediate Similarity	NPC200214
0.8023	Intermediate Similarity	NPC15573
0.8023	Intermediate Similarity	NPC183662
0.8023	Intermediate Similarity	NPC217372
0.8022	Intermediate Similarity	NPC293917
0.8022	Intermediate Similarity	NPC100321
0.8012	Intermediate Similarity	NPC201380
0.8012	Intermediate Similarity	NPC179787
0.8012	Intermediate Similarity	NPC122141
0.8012	Intermediate Similarity	NPC472586
0.8011	Intermediate Similarity	NPC262898
0.8011	Intermediate Similarity	NPC315555
0.7989	Intermediate Similarity	NPC324149
0.7989	Intermediate Similarity	NPC471193
0.7989	Intermediate Similarity	NPC471194
0.7977	Intermediate Similarity	NPC472443
0.7977	Intermediate Similarity	NPC270009
0.7977	Intermediate Similarity	NPC219336
0.7975	Intermediate Similarity	NPC470233
0.7974	Intermediate Similarity	NPC22079
0.7968	Intermediate Similarity	NPC314957
0.7967	Intermediate Similarity	NPC265576
0.7967	Intermediate Similarity	NPC131887
0.7965	Intermediate Similarity	NPC288785
0.7963	Intermediate Similarity	NPC124005
0.7958	Intermediate Similarity	NPC471192
0.7956	Intermediate Similarity	NPC11445
0.7956	Intermediate Similarity	NPC179701
0.7955	Intermediate Similarity	NPC308931
0.7955	Intermediate Similarity	NPC99939
0.7955	Intermediate Similarity	NPC280290
0.7943	Intermediate Similarity	NPC139291
0.7943	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 NPC63751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	578
0.2-0.3	1014
0.3-0.4	1461
0.4-0.5	2600
0.5-0.6	2011
0.6-0.7	1011
0.7-0.8	225
0.8-0.85	25
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9182	High Similarity	NPD4184	Clinical (unspecified phase)
0.9141	High Similarity	NPD6595	Phase 3
0.8929	High Similarity	NPD8431	Approved
0.8922	High Similarity	NPD6610	Clinical (unspecified phase)
0.8902	High Similarity	NPD6203	Clinical (unspecified phase)
0.8896	High Similarity	NPD5065	Approved
0.878	High Similarity	NPD482	Approved
0.8774	High Similarity	NPD4374	Clinical (unspecified phase)
0.8765	High Similarity	NPD8110	Clinical (unspecified phase)
0.8735	High Similarity	NPD4079	Approved
0.8735	High Similarity	NPD4076	Approved
0.869	High Similarity	NPD2094	Phase 2
0.869	High Similarity	NPD2095	Phase 2
0.869	High Similarity	NPD2092	Phase 2
0.8675	High Similarity	NPD3506	Approved
0.8675	High Similarity	NPD3505	Approved
0.8639	High Similarity	NPD2096	Phase 2
0.8639	High Similarity	NPD2091	Phase 2
0.8614	High Similarity	NPD749	Clinical (unspecified phase)
0.858	High Similarity	NPD5728	Clinical (unspecified phase)
0.8563	High Similarity	NPD5575	Clinical (unspecified phase)
0.8537	High Similarity	NPD5069	Clinical (unspecified phase)
0.8523	High Similarity	NPD7948	Phase 1
0.8497	Intermediate Similarity	NPD786	Approved
0.8452	Intermediate Similarity	NPD2144	Approved
0.8421	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD3100	Discontinued
0.8387	Intermediate Similarity	NPD1722	Approved
0.8383	Intermediate Similarity	NPD750	Phase 2
0.8353	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4128	Approved
0.8304	Intermediate Similarity	NPD3038	Discontinued
0.8263	Intermediate Similarity	NPD1325	Approved
0.8263	Intermediate Similarity	NPD1326	Approved
0.825	Intermediate Similarity	NPD4462	Approved
0.825	Intermediate Similarity	NPD4463	Approved
0.8214	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD4639	Approved
0.8204	Intermediate Similarity	NPD4638	Approved
0.8204	Intermediate Similarity	NPD4640	Approved
0.8197	Intermediate Similarity	NPD5901	Discontinued
0.8187	Intermediate Similarity	NPD8073	Approved
0.8187	Intermediate Similarity	NPD8386	Phase 2
0.8176	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4075	Phase 2
0.8171	Intermediate Similarity	NPD3961	Discontinued
0.8152	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD7957	Phase 1
0.8148	Intermediate Similarity	NPD2837	Discontinued
0.8142	Intermediate Similarity	NPD8072	Approved
0.8133	Intermediate Similarity	NPD3323	Discontinued
0.8108	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2172	Phase 1
0.8023	Intermediate Similarity	NPD4181	Approved
0.8022	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5426	Phase 3
0.7989	Intermediate Similarity	NPD3404	Approved
0.7979	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD8026	Phase 1
0.7957	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6217	Discontinued
0.7901	Intermediate Similarity	NPD4702	Approved
0.7901	Intermediate Similarity	NPD7618	Phase 3
0.7901	Intermediate Similarity	NPD4703	Approved
0.7901	Intermediate Similarity	NPD7619	Phase 3
0.7895	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD1038	Approved
0.7845	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD7470	Discontinued
0.7812	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD8272	Phase 2
0.7802	Intermediate Similarity	NPD7944	Discontinued
0.7798	Intermediate Similarity	NPD1403	Approved
0.7798	Intermediate Similarity	NPD1404	Approved
0.7791	Intermediate Similarity	NPD3609	Approved
0.7791	Intermediate Similarity	NPD3610	Approved
0.7789	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD484	Approved
0.7778	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2640	Approved
0.7778	Intermediate Similarity	NPD5021	Discontinued
0.7778	Intermediate Similarity	NPD2641	Approved
0.7751	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2639	Approved
0.7719	Intermediate Similarity	NPD2642	Approved
0.7716	Intermediate Similarity	NPD3813	Approved
0.7716	Intermediate Similarity	NPD5254	Discontinued
0.7701	Intermediate Similarity	NPD2928	Phase 2
0.7692	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5612	Discontinued
0.7674	Intermediate Similarity	NPD5862	Discovery
0.7674	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6158	Phase 2
0.7651	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD802	Phase 2
0.7647	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5106	Approved
0.764	Intermediate Similarity	NPD5105	Approved
0.7622	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD8093	Discontinued
0.7611	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6178	Phase 3
0.7598	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3385	Approved
0.7593	Intermediate Similarity	NPD1592	Phase 3
0.759	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4499	Approved
0.7576	Intermediate Similarity	NPD1661	Suspended
0.7576	Intermediate Similarity	NPD4547	Phase 3
0.7568	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5100	Phase 3
0.7552	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD991	Phase 2
0.7543	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5255	Approved
0.7527	Intermediate Similarity	NPD6664	Approved
0.7515	Intermediate Similarity	NPD1683	Approved
0.7514	Intermediate Similarity	NPD706	Phase 1
0.7514	Intermediate Similarity	NPD8122	Approved
0.7514	Intermediate Similarity	NPD8123	Approved
0.75	Intermediate Similarity	NPD5140	Approved
0.75	Intermediate Similarity	NPD5138	Approved
0.7487	Intermediate Similarity	NPD8094	Discontinued
0.7486	Intermediate Similarity	NPD5117	Phase 2
0.7486	Intermediate Similarity	NPD6281	Approved
0.7471	Intermediate Similarity	NPD4326	Phase 2
0.746	Intermediate Similarity	NPD4511	Phase 1
0.7458	Intermediate Similarity	NPD2382	Approved
0.7458	Intermediate Similarity	NPD2381	Approved
0.7458	Intermediate Similarity	NPD2380	Approved
0.7453	Intermediate Similarity	NPD1262	Discovery
0.7448	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3814	Phase 1
0.7447	Intermediate Similarity	NPD3825	Phase 3
0.744	Intermediate Similarity	NPD3262	Approved
0.744	Intermediate Similarity	NPD2882	Phase 1
0.7439	Intermediate Similarity	NPD3717	Discontinued
0.7439	Intermediate Similarity	NPD2006	Phase 2
0.7436	Intermediate Similarity	NPD3330	Phase 1
0.743	Intermediate Similarity	NPD6452	Discontinued
0.7425	Intermediate Similarity	NPD2430	Phase 2
0.7412	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7469	Discontinued
0.7407	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4601	Approved
0.7407	Intermediate Similarity	NPD4600	Approved
0.7405	Intermediate Similarity	NPD3475	Approved
0.7405	Intermediate Similarity	NPD4615	Phase 2
0.7405	Intermediate Similarity	NPD3476	Approved
0.7396	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3117	Approved
0.7386	Intermediate Similarity	NPD3116	Approved
0.7385	Intermediate Similarity	NPD5066	Phase 2
0.7385	Intermediate Similarity	NPD5067	Phase 2
0.738	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7271	Approved
0.7374	Intermediate Similarity	NPD5818	Discontinued
0.7374	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2844	Phase 3
0.7363	Intermediate Similarity	NPD5555	Phase 1
0.7356	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2720	Phase 1
0.7356	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6999	Discontinued
0.7354	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5913	Phase 3
0.7351	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6242	Discontinued
0.7348	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3654	Approved
0.7341	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5436	Phase 1
0.733	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2119	Approved
0.7325	Intermediate Similarity	NPD2118	Approved
0.731	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2580	Discontinued
0.7304	Intermediate Similarity	NPD7731	Approved
0.7304	Intermediate Similarity	NPD7730	Approved
0.7303	Intermediate Similarity	NPD6492	Phase 2
0.7301	Intermediate Similarity	NPD2896	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