NPASS Compound

Structure

NPC194640 OpenBabel07101719512D 24 26 0 0 1 0 0 0 0 0999 V2000 -6.7816 4.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7816 3.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0495 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1835 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9756 3.1270 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 -1.9563 0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 -1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 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 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 12 3 1 1 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 16 9 1 1 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.18
Volume:	343.626
LogP:	3.443
LogD:	3.122
LogS:	-3.496
# Rotatable Bonds:	4
TPSA:	73.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	3.478
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.928
MDCK Permeability:	4.411657755554188e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.557
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.736
Plasma Protein Binding (PPB):	83.5717544555664%
Volume Distribution (VD):	0.931
Pgp-substrate:	11.373943328857422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.364
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.406
CYP2C9-substrate:	0.704
CYP2D6-inhibitor:	0.319
CYP2D6-substrate:	0.675
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	7.16
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.892
Drug-inuced Liver Injury (DILI):	0.711
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.107
Carcinogencity:	0.072
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.234

Download Data

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

Natural Product: NPC194640

Natural Product ID:	NPC194640
*Common Name:**	Terezine D
IUPAC Name:	(3S,6S)-3-methyl-6-[[7-(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]piperazine-2,5-dione
Synonyms:	Terezine D
Standard InCHIKey:	IHJVJWQYVQWURS-LRDDRELGSA-N
Standard InCHI:	InChI=1S/C19H23N3O2/c1-11(2)7-8-13-5-4-6-15-14(10-20-17(13)15)9-16-19(24)21-12(3)18(23)22-16/h4-7,10,12,16,20H,8-9H2,1-3H3,(H,21,24)(H,22,23)/t12-,16-/m0/s1
SMILES:	CC(=CCc1cccc2c1[nH]cc2C[C@@H]1N=C(O)[C@@H](N=C1O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513584
PubChem CID:	10245773
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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO41356	Aspergillus fumigatus MR2012 + Streptomyces leeuwenhoekii strain C34	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28744271]
NPO41357	Aspergillus fumigatus MR2012 + Streptomyces leeuwenhoekii strain C34/strain C58	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28744271]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO19344	Sporormiella teretispora	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760082]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19344	Sporormiella teretispora	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3095	Organism	Sordaria fimicola	Sordaria fimicola	Activity	=	50.0	%	PMID[484963]
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	100.0	ug.mL-1	PMID[484964]

☑ 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 NPC194640 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	394
0.1-0.2	3266
0.2-0.3	17689
0.3-0.4	13957
0.4-0.5	3243
0.5-0.6	2119
0.6-0.7	1379
0.7-0.8	499
0.8-0.85	96
0.85-0.9	40
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9608	High Similarity	NPC49954
0.9608	High Similarity	NPC474561
0.9539	High Similarity	NPC282231
0.9474	High Similarity	NPC279918
0.9419	High Similarity	NPC63751
0.9231	High Similarity	NPC160105
0.9231	High Similarity	NPC54988
0.9211	High Similarity	NPC207726
0.9141	High Similarity	NPC165495
0.9068	High Similarity	NPC248454
0.9068	High Similarity	NPC59269
0.9032	High Similarity	NPC67056
0.902	High Similarity	NPC25008
0.902	High Similarity	NPC469765
0.902	High Similarity	NPC73952
0.902	High Similarity	NPC469763
0.902	High Similarity	NPC469760
0.902	High Similarity	NPC259644
0.902	High Similarity	NPC469786
0.9	High Similarity	NPC314603
0.8961	High Similarity	NPC70922
0.8961	High Similarity	NPC211572
0.8961	High Similarity	NPC212376
0.8961	High Similarity	NPC75540
0.8961	High Similarity	NPC80597
0.8917	High Similarity	NPC16667
0.8903	High Similarity	NPC285469
0.8848	High Similarity	NPC163055
0.8846	High Similarity	NPC469762
0.8805	High Similarity	NPC470508
0.8782	High Similarity	NPC469785
0.875	High Similarity	NPC314372
0.8742	High Similarity	NPC311276
0.8696	High Similarity	NPC201700
0.869	High Similarity	NPC474707
0.8675	High Similarity	NPC233936
0.8659	High Similarity	NPC267885
0.8642	High Similarity	NPC280548
0.8639	High Similarity	NPC204565
0.8639	High Similarity	NPC317030
0.8618	High Similarity	NPC190296
0.8598	High Similarity	NPC110500
0.8598	High Similarity	NPC203468
0.8598	High Similarity	NPC149155
0.8588	High Similarity	NPC65215
0.8588	High Similarity	NPC173028
0.8581	High Similarity	NPC187951
0.8554	High Similarity	NPC248041
0.8554	High Similarity	NPC126709
0.8553	High Similarity	NPC230869
0.8528	High Similarity	NPC194411
0.8526	High Similarity	NPC105818
0.8526	High Similarity	NPC24678
0.8521	High Similarity	NPC15102
0.8509	High Similarity	NPC40779
0.8494	Intermediate Similarity	NPC68354
0.8485	Intermediate Similarity	NPC472586
0.8471	Intermediate Similarity	NPC235684
0.8466	Intermediate Similarity	NPC78020
0.8443	Intermediate Similarity	NPC213468
0.8443	Intermediate Similarity	NPC283219
0.8439	Intermediate Similarity	NPC477167
0.8439	Intermediate Similarity	NPC473342
0.8391	Intermediate Similarity	NPC474177
0.8387	Intermediate Similarity	NPC159856
0.8385	Intermediate Similarity	NPC131718
0.8383	Intermediate Similarity	NPC151939
0.8383	Intermediate Similarity	NPC14113
0.8383	Intermediate Similarity	NPC84827
0.8383	Intermediate Similarity	NPC145885
0.8373	Intermediate Similarity	NPC275305
0.8373	Intermediate Similarity	NPC37423
0.8372	Intermediate Similarity	NPC321708
0.8372	Intermediate Similarity	NPC213629
0.8366	Intermediate Similarity	NPC469767
0.8366	Intermediate Similarity	NPC469783
0.8366	Intermediate Similarity	NPC469761
0.8366	Intermediate Similarity	NPC469784
0.8366	Intermediate Similarity	NPC469779
0.8366	Intermediate Similarity	NPC469768
0.8366	Intermediate Similarity	NPC469780
0.8365	Intermediate Similarity	NPC38736
0.8353	Intermediate Similarity	NPC228835
0.8344	Intermediate Similarity	NPC37548
0.8343	Intermediate Similarity	NPC133366
0.8333	Intermediate Similarity	NPC472443
0.8324	Intermediate Similarity	NPC95783
0.8314	Intermediate Similarity	NPC17059
0.8313	Intermediate Similarity	NPC34508
0.8312	Intermediate Similarity	NPC469766
0.8301	Intermediate Similarity	NPC73767
0.8289	Intermediate Similarity	NPC84911
0.8284	Intermediate Similarity	NPC300688
0.828	Intermediate Similarity	NPC471957
0.8261	Intermediate Similarity	NPC129721
0.8256	Intermediate Similarity	NPC94752
0.8253	Intermediate Similarity	NPC470498
0.8249	Intermediate Similarity	NPC229332
0.8225	Intermediate Similarity	NPC176199
0.8225	Intermediate Similarity	NPC11126
0.8225	Intermediate Similarity	NPC215795
0.8224	Intermediate Similarity	NPC96102
0.8224	Intermediate Similarity	NPC29886
0.8224	Intermediate Similarity	NPC261195
0.821	Intermediate Similarity	NPC206819
0.821	Intermediate Similarity	NPC318065
0.821	Intermediate Similarity	NPC92796
0.821	Intermediate Similarity	NPC135141
0.8202	Intermediate Similarity	NPC470499
0.8187	Intermediate Similarity	NPC472444
0.8182	Intermediate Similarity	NPC110126
0.8171	Intermediate Similarity	NPC102423
0.817	Intermediate Similarity	NPC105127
0.8166	Intermediate Similarity	NPC293472
0.8137	Intermediate Similarity	NPC470507
0.8125	Intermediate Similarity	NPC304187
0.8125	Intermediate Similarity	NPC477166
0.8118	Intermediate Similarity	NPC270009
0.8118	Intermediate Similarity	NPC55772
0.8113	Intermediate Similarity	NPC124005
0.8111	Intermediate Similarity	NPC470497
0.8107	Intermediate Similarity	NPC288785
0.8101	Intermediate Similarity	NPC143872
0.8101	Intermediate Similarity	NPC129042
0.8095	Intermediate Similarity	NPC313791
0.8092	Intermediate Similarity	NPC314002
0.8092	Intermediate Similarity	NPC163421
0.8092	Intermediate Similarity	NPC188387
0.8089	Intermediate Similarity	NPC242556
0.8086	Intermediate Similarity	NPC141353
0.8063	Intermediate Similarity	NPC53947
0.8061	Intermediate Similarity	NPC472587
0.8059	Intermediate Similarity	NPC111275
0.8046	Intermediate Similarity	NPC171171
0.8035	Intermediate Similarity	NPC204717
0.8023	Intermediate Similarity	NPC71037
0.8023	Intermediate Similarity	NPC99666
0.8023	Intermediate Similarity	NPC192270
0.8013	Intermediate Similarity	NPC279081
0.8012	Intermediate Similarity	NPC216713
0.8	Intermediate Similarity	NPC171317
0.8	Intermediate Similarity	NPC473640
0.7989	Intermediate Similarity	NPC11445
0.7988	Intermediate Similarity	NPC472123
0.7988	Intermediate Similarity	NPC56765
0.7988	Intermediate Similarity	NPC41257
0.7987	Intermediate Similarity	NPC288838
0.7977	Intermediate Similarity	NPC220765
0.7963	Intermediate Similarity	NPC200214
0.7961	Intermediate Similarity	NPC82295
0.7956	Intermediate Similarity	NPC100321
0.7956	Intermediate Similarity	NPC293917
0.7944	Intermediate Similarity	NPC227582
0.7944	Intermediate Similarity	NPC262898
0.7941	Intermediate Similarity	NPC189812
0.7941	Intermediate Similarity	NPC329688
0.7933	Intermediate Similarity	NPC195239
0.7933	Intermediate Similarity	NPC157828
0.7927	Intermediate Similarity	NPC286427
0.7923	Intermediate Similarity	NPC193761
0.7923	Intermediate Similarity	NPC476874
0.7917	Intermediate Similarity	NPC317430
0.7912	Intermediate Similarity	NPC106771
0.7912	Intermediate Similarity	NPC303820
0.7912	Intermediate Similarity	NPC23420
0.7912	Intermediate Similarity	NPC205254
0.7907	Intermediate Similarity	NPC219336
0.7903	Intermediate Similarity	NPC314957
0.7898	Intermediate Similarity	NPC46580
0.7898	Intermediate Similarity	NPC230002
0.7895	Intermediate Similarity	NPC22079
0.7889	Intermediate Similarity	NPC179701
0.7888	Intermediate Similarity	NPC321911
0.7886	Intermediate Similarity	NPC280290
0.7874	Intermediate Similarity	NPC469358
0.7874	Intermediate Similarity	NPC48938
0.7869	Intermediate Similarity	NPC52909
0.7869	Intermediate Similarity	NPC94211
0.7869	Intermediate Similarity	NPC475506
0.7869	Intermediate Similarity	NPC475935
0.7866	Intermediate Similarity	NPC184476
0.7861	Intermediate Similarity	NPC91179
0.7857	Intermediate Similarity	NPC49217
0.7849	Intermediate Similarity	NPC15573
0.7849	Intermediate Similarity	NPC217372
0.7849	Intermediate Similarity	NPC183662
0.7844	Intermediate Similarity	NPC90723
0.7841	Intermediate Similarity	NPC315555
0.7841	Intermediate Similarity	NPC62749
0.7831	Intermediate Similarity	NPC473320
0.7826	Intermediate Similarity	NPC179787
0.7826	Intermediate Similarity	NPC155143
0.7826	Intermediate Similarity	NPC469811
0.7826	Intermediate Similarity	NPC201380
0.7824	Intermediate Similarity	NPC6982
0.7814	Intermediate Similarity	NPC252338
0.7805	Intermediate Similarity	NPC471458
0.7778	Intermediate Similarity	NPC307963
0.7771	Intermediate Similarity	NPC472108
0.7771	Intermediate Similarity	NPC139291

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 NPC194640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	552
0.2-0.3	1035
0.3-0.4	1460
0.4-0.5	2776
0.5-0.6	2097
0.6-0.7	847
0.7-0.8	158
0.8-0.85	22
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9114	High Similarity	NPD4184	Clinical (unspecified phase)
0.8841	High Similarity	NPD6595	Phase 3
0.875	High Similarity	NPD8431	Approved
0.8743	High Similarity	NPD6610	Clinical (unspecified phase)
0.8606	High Similarity	NPD6203	Clinical (unspecified phase)
0.8606	High Similarity	NPD2144	Approved
0.8598	High Similarity	NPD482	Approved
0.8581	High Similarity	NPD3100	Discontinued
0.8554	High Similarity	NPD4079	Approved
0.8554	High Similarity	NPD4076	Approved
0.8545	High Similarity	NPD749	Clinical (unspecified phase)
0.8512	High Similarity	NPD2092	Phase 2
0.8512	High Similarity	NPD2094	Phase 2
0.8512	High Similarity	NPD2095	Phase 2
0.8494	Intermediate Similarity	NPD3505	Approved
0.8494	Intermediate Similarity	NPD3506	Approved
0.848	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD2091	Phase 2
0.8462	Intermediate Similarity	NPD2096	Phase 2
0.8452	Intermediate Similarity	NPD3038	Discontinued
0.8421	Intermediate Similarity	NPD786	Approved
0.8402	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD5065	Approved
0.8333	Intermediate Similarity	NPD8386	Phase 2
0.8313	Intermediate Similarity	NPD750	Phase 2
0.8303	Intermediate Similarity	NPD1325	Approved
0.8303	Intermediate Similarity	NPD1326	Approved
0.8228	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1722	Approved
0.8176	Intermediate Similarity	NPD2172	Phase 1
0.8155	Intermediate Similarity	NPD4128	Approved
0.8133	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4640	Approved
0.8133	Intermediate Similarity	NPD4638	Approved
0.8133	Intermediate Similarity	NPD4639	Approved
0.8107	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7948	Phase 1
0.8	Intermediate Similarity	NPD4075	Phase 2
0.8	Intermediate Similarity	NPD3961	Discontinued
0.7965	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD4463	Approved
0.795	Intermediate Similarity	NPD4462	Approved
0.7939	Intermediate Similarity	NPD1403	Approved
0.7939	Intermediate Similarity	NPD1404	Approved
0.7937	Intermediate Similarity	NPD4702	Approved
0.7937	Intermediate Similarity	NPD4703	Approved
0.7935	Intermediate Similarity	NPD5901	Discontinued
0.7929	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD8073	Approved
0.7917	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2640	Approved
0.7917	Intermediate Similarity	NPD2641	Approved
0.7892	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7957	Phase 1
0.788	Intermediate Similarity	NPD8072	Approved
0.7857	Intermediate Similarity	NPD2642	Approved
0.7857	Intermediate Similarity	NPD2639	Approved
0.7849	Intermediate Similarity	NPD4181	Approved
0.7844	Intermediate Similarity	NPD3323	Discontinued
0.7819	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5100	Phase 3
0.7778	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1038	Approved
0.7754	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2837	Discontinued
0.7742	Intermediate Similarity	NPD5426	Phase 3
0.7742	Intermediate Similarity	NPD8272	Phase 2
0.7722	Intermediate Similarity	NPD3404	Approved
0.7692	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5254	Discontinued
0.7632	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD484	Approved
0.7616	Intermediate Similarity	NPD3610	Approved
0.7616	Intermediate Similarity	NPD3609	Approved
0.7607	Intermediate Similarity	NPD4547	Phase 3
0.7602	Intermediate Similarity	NPD5021	Discontinued
0.7592	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7470	Discontinued
0.7582	Intermediate Similarity	NPD802	Phase 2
0.7574	Intermediate Similarity	NPD8026	Phase 1
0.7571	Intermediate Similarity	NPD5105	Approved
0.7571	Intermediate Similarity	NPD5106	Approved
0.7565	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6217	Discontinued
0.7541	Intermediate Similarity	NPD7618	Phase 3
0.7541	Intermediate Similarity	NPD7944	Discontinued
0.7541	Intermediate Similarity	NPD7619	Phase 3
0.7516	Intermediate Similarity	NPD1592	Phase 3
0.7514	Intermediate Similarity	NPD5117	Phase 2
0.7514	Intermediate Similarity	NPD4499	Approved
0.7513	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1661	Suspended
0.75	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3717	Discontinued
0.7469	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD8093	Discontinued
0.7456	Intermediate Similarity	NPD5255	Approved
0.7448	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD706	Phase 1
0.744	Intermediate Similarity	NPD2580	Discontinued
0.7439	Intermediate Similarity	NPD1683	Approved
0.7436	Intermediate Similarity	NPD3475	Approved
0.7436	Intermediate Similarity	NPD3476	Approved
0.7427	Intermediate Similarity	NPD5140	Approved
0.7427	Intermediate Similarity	NPD5138	Approved
0.7425	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2381	Approved
0.7386	Intermediate Similarity	NPD2382	Approved
0.7386	Intermediate Similarity	NPD2380	Approved
0.7382	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3654	Approved
0.7371	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6664	Approved
0.7365	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6158	Phase 2
0.7365	Intermediate Similarity	NPD2882	Phase 1
0.7362	Intermediate Similarity	NPD2006	Phase 2
0.736	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD991	Phase 2
0.7355	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2119	Approved
0.7355	Intermediate Similarity	NPD2118	Approved
0.7349	Intermediate Similarity	NPD2430	Phase 2
0.7347	Intermediate Similarity	NPD5612	Discontinued
0.7337	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8094	Discontinued
0.733	Intermediate Similarity	NPD2928	Phase 2
0.7322	Intermediate Similarity	NPD6281	Approved
0.7317	Intermediate Similarity	NPD3813	Approved
0.7316	Intermediate Similarity	NPD4886	Phase 2
0.7314	Intermediate Similarity	NPD3117	Approved
0.7314	Intermediate Similarity	NPD3116	Approved
0.7308	Intermediate Similarity	NPD4948	Discontinued
0.7308	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4511	Phase 1
0.7299	Intermediate Similarity	NPD5862	Discovery
0.7299	Intermediate Similarity	NPD2844	Phase 3
0.7296	Intermediate Similarity	NPD3385	Approved
0.7283	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2720	Phase 1
0.7283	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD3330	Phase 1
0.7273	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4601	Approved
0.7249	Intermediate Similarity	NPD4600	Approved
0.7247	Intermediate Similarity	NPD8122	Approved
0.7247	Intermediate Similarity	NPD8123	Approved
0.7247	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4957	Phase 2
0.7228	Intermediate Similarity	NPD7271	Approved
0.7228	Intermediate Similarity	NPD2565	Phase 2
0.7228	Intermediate Similarity	NPD2564	Approved
0.7222	Intermediate Similarity	NPD2896	Discontinued
0.7212	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1392	Approved
0.7193	Intermediate Similarity	NPD4326	Phase 2
0.7188	Intermediate Similarity	NPD4030	Approved
0.7188	Intermediate Similarity	NPD4028	Approved
0.7188	Intermediate Similarity	NPD4029	Approved
0.7182	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5315	Discontinued
0.7159	Intermediate Similarity	NPD5436	Phase 1
0.7157	Intermediate Similarity	NPD7730	Approved
0.7157	Intermediate Similarity	NPD7731	Approved
0.7152	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4615	Phase 2
0.7143	Intermediate Similarity	NPD5067	Phase 2
0.7143	Intermediate Similarity	NPD6178	Phase 3
0.7143	Intermediate Similarity	NPD5066	Phase 2
0.7136	Intermediate Similarity	NPD5818	Discontinued
0.7135	Intermediate Similarity	NPD3113	Approved
0.7135	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3112	Approved

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