NPASS Compound

Structure

NPC228835 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 -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 0.0000 -1.0000 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 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 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 2.0000 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 -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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 19 1 0 0 0 0 15 9 1 1 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 8 1 6 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 18 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.18
Volume:	328.967
LogP:	2.724
LogD:	3.206
LogS:	-3.312
# Rotatable Bonds:	4
TPSA:	65.2
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.907
Synthetic Accessibility Score:	3.128
Fsp3:	0.444
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:	-4.49
MDCK Permeability:	4.0960003389045596e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.745
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.784
Plasma Protein Binding (PPB):	61.59114456176758%
Volume Distribution (VD):	0.836
Pgp-substrate:	30.176883697509766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.15
CYP1A2-substrate:	0.446
CYP2C19-inhibitor:	0.779
CYP2C19-substrate:	0.605
CYP2C9-inhibitor:	0.515
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.081
CYP2D6-substrate:	0.678
CYP3A4-inhibitor:	0.859
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	7.15
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.725
Drug-inuced Liver Injury (DILI):	0.635
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.811
Skin Sensitization:	0.171
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.14

Download Data

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

Natural Product: NPC228835

Natural Product ID:	NPC228835
*Common Name:**	3(S)-(1H-Indol-3-Ylmethyl)-6-(R)-Isobutyl-1-Methylpiperazine-2,5-Dione
IUPAC Name:	(3S,6R)-3-(1H-indol-3-ylmethyl)-1-methyl-6-(2-methylpropyl)piperazine-2,5-dione
Synonyms:
Standard InCHIKey:	ZXMLGZPFSBKFTE-JKSUJKDBSA-N
Standard InCHI:	InChI=1S/C18H23N3O2/c1-11(2)8-16-17(22)20-15(18(23)21(16)3)9-12-10-19-14-7-5-4-6-13(12)14/h4-7,10-11,15-16,19H,8-9H2,1-3H3,(H,20,22)/t15-,16+/m0/s1
SMILES:	CC(C[C@@H]1C(=N[C@H](C(=O)N1C)Cc1c[nH]c2c1cccc2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469410
PubChem CID:	11529722
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
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124785]
NPO33480	leptoxyphium sp.	Species	Capnodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19637889]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24738739]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31050424]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4207788]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4629903]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7528269]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	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
IC50	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	31000.0	nM	PMID[469147]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	31000.0	nM	PMID[469147]

☑ 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 NPC228835 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	336
0.1-0.2	3260
0.2-0.3	18878
0.3-0.4	13236
0.4-0.5	2380
0.5-0.6	2358
0.6-0.7	1469
0.7-0.8	650
0.8-0.85	106
0.85-0.9	16
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9755	High Similarity	NPC11126
0.9583	High Similarity	NPC17059
0.9294	High Similarity	NPC94752
0.9112	High Similarity	NPC91179
0.9034	High Similarity	NPC294693
0.8966	High Similarity	NPC213629
0.8844	High Similarity	NPC165495
0.8778	High Similarity	NPC171317
0.8721	High Similarity	NPC248041
0.8721	High Similarity	NPC126709
0.8713	High Similarity	NPC267885
0.8703	High Similarity	NPC54420
0.8696	High Similarity	NPC473376
0.869	High Similarity	NPC49954
0.869	High Similarity	NPC474561
0.8663	High Similarity	NPC145885
0.8663	High Similarity	NPC14113
0.8663	High Similarity	NPC84827
0.8655	High Similarity	NPC203468
0.8655	High Similarity	NPC149155
0.8655	High Similarity	NPC110500
0.8613	High Similarity	NPC283219
0.861	High Similarity	NPC162860
0.858	High Similarity	NPC99939
0.858	High Similarity	NPC308931
0.8531	High Similarity	NPC235684
0.8525	High Similarity	NPC293917
0.8512	High Similarity	NPC282231
0.8511	High Similarity	NPC478158
0.8506	High Similarity	NPC213468
0.847	Intermediate Similarity	NPC473640
0.8452	Intermediate Similarity	NPC279918
0.8444	Intermediate Similarity	NPC117244
0.8444	Intermediate Similarity	NPC473763
0.8436	Intermediate Similarity	NPC321708
0.8432	Intermediate Similarity	NPC475506
0.8424	Intermediate Similarity	NPC100321
0.8421	Intermediate Similarity	NPC63751
0.8421	Intermediate Similarity	NPC78020
0.8387	Intermediate Similarity	NPC155143
0.8382	Intermediate Similarity	NPC161861
0.8377	Intermediate Similarity	NPC6865
0.8377	Intermediate Similarity	NPC153980
0.8373	Intermediate Similarity	NPC25008
0.8373	Intermediate Similarity	NPC469763
0.8373	Intermediate Similarity	NPC259644
0.8373	Intermediate Similarity	NPC73952
0.8373	Intermediate Similarity	NPC469760
0.8373	Intermediate Similarity	NPC469765
0.8373	Intermediate Similarity	NPC469786
0.8363	Intermediate Similarity	NPC160105
0.8353	Intermediate Similarity	NPC194640
0.8351	Intermediate Similarity	NPC477714
0.8344	Intermediate Similarity	NPC314372
0.8333	Intermediate Similarity	NPC54744
0.8333	Intermediate Similarity	NPC300183
0.8325	Intermediate Similarity	NPC72956
0.8323	Intermediate Similarity	NPC211572
0.8323	Intermediate Similarity	NPC80597
0.8323	Intermediate Similarity	NPC212376
0.8323	Intermediate Similarity	NPC75540
0.8323	Intermediate Similarity	NPC70922
0.8295	Intermediate Similarity	NPC219336
0.829	Intermediate Similarity	NPC478157
0.8281	Intermediate Similarity	NPC471194
0.8281	Intermediate Similarity	NPC75634
0.8281	Intermediate Similarity	NPC471193
0.828	Intermediate Similarity	NPC470497
0.827	Intermediate Similarity	NPC470499
0.8266	Intermediate Similarity	NPC194411
0.8256	Intermediate Similarity	NPC281049
0.8256	Intermediate Similarity	NPC54988
0.8239	Intermediate Similarity	NPC217372
0.8239	Intermediate Similarity	NPC183662
0.8239	Intermediate Similarity	NPC68354
0.8239	Intermediate Similarity	NPC15573
0.8229	Intermediate Similarity	NPC469938
0.8225	Intermediate Similarity	NPC469762
0.8225	Intermediate Similarity	NPC299594
0.8221	Intermediate Similarity	NPC190296
0.822	Intermediate Similarity	NPC107077
0.822	Intermediate Similarity	NPC223791
0.8216	Intermediate Similarity	NPC262898
0.8212	Intermediate Similarity	NPC477003
0.8205	Intermediate Similarity	NPC477715
0.8192	Intermediate Similarity	NPC248462
0.8171	Intermediate Similarity	NPC314603
0.8166	Intermediate Similarity	NPC469785
0.8162	Intermediate Similarity	NPC179701
0.8155	Intermediate Similarity	NPC200214
0.8154	Intermediate Similarity	NPC471192
0.8144	Intermediate Similarity	NPC105818
0.8144	Intermediate Similarity	NPC24678
0.814	Intermediate Similarity	NPC21174
0.814	Intermediate Similarity	NPC311276
0.814	Intermediate Similarity	NPC271797
0.8136	Intermediate Similarity	NPC248454
0.8136	Intermediate Similarity	NPC111275
0.8136	Intermediate Similarity	NPC59269
0.8135	Intermediate Similarity	NPC320968
0.8125	Intermediate Similarity	NPC275305
0.8125	Intermediate Similarity	NPC37423
0.8122	Intermediate Similarity	NPC62749
0.8121	Intermediate Similarity	NPC470440
0.8114	Intermediate Similarity	NPC6982
0.8108	Intermediate Similarity	NPC195239
0.8108	Intermediate Similarity	NPC157828
0.8101	Intermediate Similarity	NPC233936
0.8093	Intermediate Similarity	NPC110602
0.8093	Intermediate Similarity	NPC75726
0.8093	Intermediate Similarity	NPC31385
0.809	Intermediate Similarity	NPC55772
0.8066	Intermediate Similarity	NPC15102
0.8065	Intermediate Similarity	NPC11445
0.8045	Intermediate Similarity	NPC469896
0.8043	Intermediate Similarity	NPC476460
0.8037	Intermediate Similarity	NPC73767
0.8035	Intermediate Similarity	NPC271734
0.8035	Intermediate Similarity	NPC40779
0.8034	Intermediate Similarity	NPC64436
0.8012	Intermediate Similarity	NPC159856
0.8	Intermediate Similarity	NPC201700
0.8	Intermediate Similarity	NPC47190
0.8	Intermediate Similarity	NPC155444
0.7989	Intermediate Similarity	NPC176199
0.7989	Intermediate Similarity	NPC215795
0.7988	Intermediate Similarity	NPC469767
0.7988	Intermediate Similarity	NPC469761
0.7988	Intermediate Similarity	NPC469783
0.7988	Intermediate Similarity	NPC469784
0.7988	Intermediate Similarity	NPC469780
0.7988	Intermediate Similarity	NPC469779
0.7988	Intermediate Similarity	NPC469768
0.798	Intermediate Similarity	NPC191382
0.798	Intermediate Similarity	NPC56109
0.7976	Intermediate Similarity	NPC37548
0.797	Intermediate Similarity	NPC470732
0.797	Intermediate Similarity	NPC470731
0.7967	Intermediate Similarity	NPC133003
0.7965	Intermediate Similarity	NPC206819
0.7965	Intermediate Similarity	NPC318065
0.7956	Intermediate Similarity	NPC163055
0.7953	Intermediate Similarity	NPC285469
0.7946	Intermediate Similarity	NPC243716
0.7944	Intermediate Similarity	NPC16659
0.7939	Intermediate Similarity	NPC469766
0.7937	Intermediate Similarity	NPC220797
0.7937	Intermediate Similarity	NPC474318
0.7937	Intermediate Similarity	NPC475914
0.7937	Intermediate Similarity	NPC268744
0.7937	Intermediate Similarity	NPC201266
0.7937	Intermediate Similarity	NPC153123
0.7935	Intermediate Similarity	NPC175474
0.7927	Intermediate Similarity	NPC110126
0.7926	Intermediate Similarity	NPC227582
0.7917	Intermediate Similarity	NPC471957
0.7914	Intermediate Similarity	NPC84911
0.791	Intermediate Similarity	NPC470498
0.7906	Intermediate Similarity	NPC476874
0.7895	Intermediate Similarity	NPC77241
0.7895	Intermediate Similarity	NPC166209
0.7895	Intermediate Similarity	NPC13456
0.7895	Intermediate Similarity	NPC269203
0.7889	Intermediate Similarity	NPC265710
0.7884	Intermediate Similarity	NPC131887
0.7882	Intermediate Similarity	NPC319232
0.7882	Intermediate Similarity	NPC24370
0.7871	Intermediate Similarity	NPC64216
0.7869	Intermediate Similarity	NPC280290
0.7865	Intermediate Similarity	NPC317701
0.7864	Intermediate Similarity	NPC89987
0.7861	Intermediate Similarity	NPC92796
0.7861	Intermediate Similarity	NPC135141
0.7857	Intermediate Similarity	NPC470205
0.7853	Intermediate Similarity	NPC471944
0.7853	Intermediate Similarity	NPC29886
0.7853	Intermediate Similarity	NPC96102
0.7853	Intermediate Similarity	NPC261195
0.7841	Intermediate Similarity	NPC56233
0.7833	Intermediate Similarity	NPC240088
0.7833	Intermediate Similarity	NPC284775
0.7833	Intermediate Similarity	NPC473380
0.7829	Intermediate Similarity	NPC478182
0.7826	Intermediate Similarity	NPC478077
0.7826	Intermediate Similarity	NPC315555
0.7826	Intermediate Similarity	NPC474707
0.7824	Intermediate Similarity	NPC53947
0.7816	Intermediate Similarity	NPC131718
0.7812	Intermediate Similarity	NPC476073
0.7805	Intermediate Similarity	NPC105127
0.7802	Intermediate Similarity	NPC191415
0.7802	Intermediate Similarity	NPC71037
0.7801	Intermediate Similarity	NPC252338
0.7791	Intermediate Similarity	NPC470507
0.7791	Intermediate Similarity	NPC38736
0.7789	Intermediate Similarity	NPC474389
0.7784	Intermediate Similarity	NPC204565
0.7784	Intermediate Similarity	NPC317030
0.7772	Intermediate Similarity	NPC98715
0.7771	Intermediate Similarity	NPC16667

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 NPC228835 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	504
0.2-0.3	1027
0.3-0.4	1622
0.4-0.5	2255
0.5-0.6	2264
0.6-0.7	1053
0.7-0.8	195
0.8-0.85	27
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.882	High Similarity	NPD7619	Phase 3
0.882	High Similarity	NPD7618	Phase 3
0.8678	High Similarity	NPD5728	Clinical (unspecified phase)
0.8655	High Similarity	NPD482	Approved
0.8605	High Similarity	NPD749	Clinical (unspecified phase)
0.8588	High Similarity	NPD3961	Discontinued
0.8571	High Similarity	NPD2095	Phase 2
0.8571	High Similarity	NPD2092	Phase 2
0.8571	High Similarity	NPD2094	Phase 2
0.8525	High Similarity	NPD7621	Clinical (unspecified phase)
0.8523	High Similarity	NPD2091	Phase 2
0.8523	High Similarity	NPD2096	Phase 2
0.8503	High Similarity	NPD8493	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD4075	Phase 2
0.8488	Intermediate Similarity	NPD750	Phase 2
0.8432	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD6664	Approved
0.8298	Intermediate Similarity	NPD8272	Phase 2
0.8295	Intermediate Similarity	NPD4076	Approved
0.8295	Intermediate Similarity	NPD4079	Approved
0.8272	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD3505	Approved
0.8239	Intermediate Similarity	NPD3506	Approved
0.8229	Intermediate Similarity	NPD7470	Discontinued
0.8211	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8142	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.8135	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8122	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7944	Discontinued
0.8103	Intermediate Similarity	NPD7970	Approved
0.8103	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.8093	Intermediate Similarity	NPD8093	Discontinued
0.8093	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3100	Discontinued
0.8077	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD786	Approved
0.8034	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD4128	Approved
0.8022	Intermediate Similarity	NPD6217	Discontinued
0.8011	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD7780	Approved
0.798	Intermediate Similarity	NPD7781	Approved
0.7944	Intermediate Similarity	NPD6595	Phase 3
0.7939	Intermediate Similarity	NPD1722	Approved
0.7933	Intermediate Similarity	NPD2144	Approved
0.7931	Intermediate Similarity	NPD3583	Phase 2
0.7921	Intermediate Similarity	NPD5065	Approved
0.7917	Intermediate Similarity	NPD5426	Phase 3
0.7901	Intermediate Similarity	NPD3038	Discontinued
0.7882	Intermediate Similarity	NPD7603	Discontinued
0.787	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD8094	Discontinued
0.7853	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7839	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD4181	Approved
0.7824	Intermediate Similarity	NPD5901	Discontinued
0.7797	Intermediate Similarity	NPD4640	Approved
0.7797	Intermediate Similarity	NPD4638	Approved
0.7797	Intermediate Similarity	NPD4639	Approved
0.7784	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7564	Discontinued
0.7716	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD484	Approved
0.7688	Intermediate Similarity	NPD8431	Approved
0.7684	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7730	Approved
0.767	Intermediate Similarity	NPD7731	Approved
0.7668	Intermediate Similarity	NPD5017	Discontinued
0.7659	Intermediate Similarity	NPD7271	Approved
0.7656	Intermediate Similarity	NPD7953	Approved
0.7656	Intermediate Similarity	NPD7950	Approved
0.7656	Intermediate Similarity	NPD7789	Approved
0.7656	Intermediate Similarity	NPD7951	Approved
0.7656	Intermediate Similarity	NPD7790	Approved
0.7656	Intermediate Similarity	NPD7952	Approved
0.7656	Intermediate Similarity	NPD7791	Approved
0.7644	Intermediate Similarity	NPD2880	Discontinued
0.7641	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD3323	Discontinued
0.7622	Intermediate Similarity	NPD6178	Phase 3
0.7619	Intermediate Similarity	NPD4922	Phase 2
0.7619	Intermediate Similarity	NPD6665	Discontinued
0.7617	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4462	Approved
0.7616	Intermediate Similarity	NPD2172	Phase 1
0.7616	Intermediate Similarity	NPD4463	Approved
0.7614	Intermediate Similarity	NPD2511	Approved
0.7606	Intermediate Similarity	NPD4499	Approved
0.7602	Intermediate Similarity	NPD7957	Phase 1
0.7602	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD2640	Approved
0.7598	Intermediate Similarity	NPD2641	Approved
0.7596	Intermediate Similarity	NPD7824	Approved
0.7592	Intermediate Similarity	NPD4848	Phase 1
0.7592	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD8072	Approved
0.7568	Intermediate Similarity	NPD3320	Approved
0.7568	Intermediate Similarity	NPD3318	Approved
0.7568	Intermediate Similarity	NPD3319	Phase 1
0.7563	Intermediate Similarity	NPD8322	Phase 2
0.7538	Intermediate Similarity	NPD8073	Approved
0.7536	Intermediate Similarity	NPD7711	Discontinued
0.7529	Intermediate Similarity	NPD2837	Discontinued
0.7527	Intermediate Similarity	NPD7482	Phase 2
0.7527	Intermediate Similarity	NPD7483	Phase 2
0.7526	Intermediate Similarity	NPD4601	Approved
0.7526	Intermediate Similarity	NPD4600	Approved
0.7514	Intermediate Similarity	NPD1403	Approved
0.7514	Intermediate Similarity	NPD3178	Discontinued
0.7514	Intermediate Similarity	NPD1404	Approved
0.7514	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD201	Phase 2
0.7485	Intermediate Similarity	NPD200	Phase 2
0.7475	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6999	Discontinued
0.7474	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6771	Discontinued
0.7471	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7026	Phase 2
0.7444	Intermediate Similarity	NPD2642	Approved
0.7444	Intermediate Similarity	NPD2639	Approved
0.7435	Intermediate Similarity	NPD5505	Discontinued
0.7432	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3610	Approved
0.7418	Intermediate Similarity	NPD3609	Approved
0.7409	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4703	Approved
0.7399	Intermediate Similarity	NPD4702	Approved
0.7398	Intermediate Similarity	NPD7817	Phase 1
0.7396	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6044	Discontinued
0.7385	Intermediate Similarity	NPD6249	Phase 2
0.7385	Intermediate Similarity	NPD6248	Phase 2
0.7377	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8114	Approved
0.7374	Intermediate Similarity	NPD8115	Approved
0.7366	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2442	Approved
0.735	Intermediate Similarity	NPD2509	Approved
0.735	Intermediate Similarity	NPD7666	Phase 3
0.735	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2510	Approved
0.735	Intermediate Similarity	NPD7665	Phase 2
0.735	Intermediate Similarity	NPD2443	Approved
0.7347	Intermediate Similarity	NPD4501	Approved
0.7347	Intermediate Similarity	NPD4500	Approved
0.7345	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7001	Phase 3
0.7337	Intermediate Similarity	NPD2896	Discontinued
0.7333	Intermediate Similarity	NPD6164	Phase 2
0.7333	Intermediate Similarity	NPD6165	Phase 2
0.733	Intermediate Similarity	NPD5198	Approved
0.733	Intermediate Similarity	NPD5199	Approved
0.7323	Intermediate Similarity	NPD5487	Phase 1
0.7316	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3968	Approved
0.7308	Intermediate Similarity	NPD5021	Discontinued
0.7308	Intermediate Similarity	NPD2844	Phase 3
0.7303	Intermediate Similarity	NPD4326	Phase 2
0.7302	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1661	Suspended
0.7297	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7308	Discontinued
0.7293	Intermediate Similarity	NPD2915	Discontinued
0.7287	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7948	Phase 1
0.7282	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5400	Approved
0.7277	Intermediate Similarity	NPD4334	Discontinued
0.7273	Intermediate Similarity	NPD5473	Discontinued
0.7273	Intermediate Similarity	NPD7717	Approved
0.7273	Intermediate Similarity	NPD7716	Approved
0.7273	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD1326	Approved
0.7268	Intermediate Similarity	NPD1325	Approved
0.7268	Intermediate Similarity	NPD4602	Approved
0.7263	Intermediate Similarity	NPD5809	Phase 3
0.726	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5611	Phase 2
0.725	Intermediate Similarity	NPD2008	Discontinued
0.7249	Intermediate Similarity	NPD1096	Discontinued
0.7247	Intermediate Similarity	NPD2580	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