NPASS Compound

Structure

NPC299594 OpenBabel07101718332D 24 26 0 0 0 0 0 0 0 0999 V2000 3.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6150 4.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6150 3.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 4.9635 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 5.0495 1.6488 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 3.3175 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 4.1835 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 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 0.3090 0.9511 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 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4811 4.0975 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 1.9563 0.4158 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 -0.3601 1.6942 0.0000 O 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 4 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 2 0 0 0 0 8 12 2 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 14 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.13
Volume:	329.848
LogP:	2.088
LogD:	2.101
LogS:	-3.636
# Rotatable Bonds:	4
TPSA:	91.39
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.51
Synthetic Accessibility Score:	3.303
Fsp3:	0.222
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:	-4.909
MDCK Permeability:	2.1021480279159732e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.425
Plasma Protein Binding (PPB):	88.50623321533203%
Volume Distribution (VD):	0.416
Pgp-substrate:	3.87985897064209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.76
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.364
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.386
CYP3A4-inhibitor:	0.39
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	1.268
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.781
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.393
Carcinogencity:	0.184
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC299594

Natural Product ID:	NPC299594
*Common Name:**	NMYIPKXDNJVHNS-LCYFTJDESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NMYIPKXDNJVHNS-LCYFTJDESA-N
Standard InCHI:	InChI=1S/C18H17N3O3/c1-4-18(2,3)14-11(10-7-5-6-8-12(10)19-14)9-13-15(22)21-17(24)16(23)20-13/h4-9,19H,1H2,2-3H3,(H,20,23)(H,21,22,24)/b13-9-
SMILES:	C=CC(c1[nH]c2c(c1/C=C/1NC(=O)C(=O)N=C1O)cccc2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3417738
PubChem CID:	n.a.
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
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
LD50	1
Others	2

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	200000.0	nM	PMID[452540]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	6.69	%	PMID[452540]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	3.9	uM	PMID[452541]

☑ 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 NPC299594 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	443
0.1-0.2	3850
0.2-0.3	18179
0.3-0.4	13481
0.4-0.5	2868
0.5-0.6	2154
0.6-0.7	1370
0.7-0.8	325
0.8-0.85	16
0.85-0.9	7
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC271734
0.931	High Similarity	NPC242556
0.906	High Similarity	NPC37548
0.906	High Similarity	NPC124005
0.8854	High Similarity	NPC470509
0.8824	High Similarity	NPC38736
0.8824	High Similarity	NPC471458
0.8824	High Similarity	NPC470507
0.8808	High Similarity	NPC187951
0.88	High Similarity	NPC129042
0.8766	High Similarity	NPC184476
0.8599	High Similarity	NPC473320
0.8487	Intermediate Similarity	NPC470440
0.8457	Intermediate Similarity	NPC6982
0.8408	Intermediate Similarity	NPC285469
0.8373	Intermediate Similarity	NPC91179
0.8313	Intermediate Similarity	NPC11126
0.8261	Intermediate Similarity	NPC472587
0.8231	Intermediate Similarity	NPC22079
0.8225	Intermediate Similarity	NPC228835
0.8199	Intermediate Similarity	NPC16667
0.8182	Intermediate Similarity	NPC34508
0.8176	Intermediate Similarity	NPC141353
0.8153	Intermediate Similarity	NPC24678
0.8153	Intermediate Similarity	NPC105818
0.8113	Intermediate Similarity	NPC207726
0.8084	Intermediate Similarity	NPC288785
0.8072	Intermediate Similarity	NPC161861
0.8054	Intermediate Similarity	NPC475450
0.8023	Intermediate Similarity	NPC94752
0.8013	Intermediate Similarity	NPC198988
0.8013	Intermediate Similarity	NPC159856
0.7988	Intermediate Similarity	NPC270009
0.7987	Intermediate Similarity	NPC2949
0.7977	Intermediate Similarity	NPC17059
0.7963	Intermediate Similarity	NPC67056
0.7961	Intermediate Similarity	NPC325252
0.7959	Intermediate Similarity	NPC250361
0.7952	Intermediate Similarity	NPC280548
0.7937	Intermediate Similarity	NPC281094
0.7931	Intermediate Similarity	NPC41174
0.7919	Intermediate Similarity	NPC473587
0.7907	Intermediate Similarity	NPC165495
0.7898	Intermediate Similarity	NPC314372
0.7895	Intermediate Similarity	NPC192270
0.7885	Intermediate Similarity	NPC190296
0.7867	Intermediate Similarity	NPC475428
0.7853	Intermediate Similarity	NPC135141
0.7853	Intermediate Similarity	NPC92796
0.7852	Intermediate Similarity	NPC473762
0.7848	Intermediate Similarity	NPC478186
0.7843	Intermediate Similarity	NPC218268
0.7831	Intermediate Similarity	NPC49954
0.7831	Intermediate Similarity	NPC474561
0.7824	Intermediate Similarity	NPC293472
0.7815	Intermediate Similarity	NPC179365
0.7809	Intermediate Similarity	NPC294693
0.7806	Intermediate Similarity	NPC88097
0.7798	Intermediate Similarity	NPC470498
0.7778	Intermediate Similarity	NPC219336
0.7778	Intermediate Similarity	NPC472443
0.7771	Intermediate Similarity	NPC470508
0.7763	Intermediate Similarity	NPC473930
0.7758	Intermediate Similarity	NPC282231
0.7756	Intermediate Similarity	NPC238499
0.7756	Intermediate Similarity	NPC59084
0.7756	Intermediate Similarity	NPC115611
0.7738	Intermediate Similarity	NPC471943
0.7727	Intermediate Similarity	NPC213629
0.7719	Intermediate Similarity	NPC15573
0.7719	Intermediate Similarity	NPC183662
0.7719	Intermediate Similarity	NPC217372
0.7716	Intermediate Similarity	NPC73952
0.7716	Intermediate Similarity	NPC469760
0.7716	Intermediate Similarity	NPC469765
0.7716	Intermediate Similarity	NPC259644
0.7716	Intermediate Similarity	NPC469786
0.7716	Intermediate Similarity	NPC25008
0.7716	Intermediate Similarity	NPC469763
0.7711	Intermediate Similarity	NPC21174
0.7711	Intermediate Similarity	NPC271797
0.7707	Intermediate Similarity	NPC473868
0.7707	Intermediate Similarity	NPC63157
0.7707	Intermediate Similarity	NPC277157
0.7697	Intermediate Similarity	NPC279918
0.7688	Intermediate Similarity	NPC477134
0.768	Intermediate Similarity	NPC470499
0.7679	Intermediate Similarity	NPC63751
0.7669	Intermediate Similarity	NPC212376
0.7669	Intermediate Similarity	NPC75540
0.7669	Intermediate Similarity	NPC211572
0.7669	Intermediate Similarity	NPC70922
0.7669	Intermediate Similarity	NPC80597
0.7661	Intermediate Similarity	NPC151635
0.7657	Intermediate Similarity	NPC133003
0.7644	Intermediate Similarity	NPC472444
0.7643	Intermediate Similarity	NPC469783
0.7643	Intermediate Similarity	NPC469761
0.7643	Intermediate Similarity	NPC469767
0.7643	Intermediate Similarity	NPC469779
0.7643	Intermediate Similarity	NPC469784
0.7643	Intermediate Similarity	NPC469768
0.7643	Intermediate Similarity	NPC469780
0.764	Intermediate Similarity	NPC243716
0.763	Intermediate Similarity	NPC469896
0.7627	Intermediate Similarity	NPC46413
0.7627	Intermediate Similarity	NPC221873
0.7619	Intermediate Similarity	NPC49217
0.7607	Intermediate Similarity	NPC200214
0.7605	Intermediate Similarity	NPC194640
0.7605	Intermediate Similarity	NPC476118
0.7605	Intermediate Similarity	NPC8104
0.7595	Intermediate Similarity	NPC469766
0.7593	Intermediate Similarity	NPC33421
0.758	Intermediate Similarity	NPC73767
0.7578	Intermediate Similarity	NPC471957
0.7576	Intermediate Similarity	NPC469762
0.7572	Intermediate Similarity	NPC176199
0.7572	Intermediate Similarity	NPC215795
0.7564	Intermediate Similarity	NPC84911
0.7564	Intermediate Similarity	NPC125746
0.7562	Intermediate Similarity	NPC204141
0.7554	Intermediate Similarity	NPC471944
0.7547	Intermediate Similarity	NPC20144
0.7545	Intermediate Similarity	NPC194881
0.7532	Intermediate Similarity	NPC284635
0.7531	Intermediate Similarity	NPC2272
0.753	Intermediate Similarity	NPC475990
0.7529	Intermediate Similarity	NPC16659
0.7529	Intermediate Similarity	NPC198339
0.7529	Intermediate Similarity	NPC65080
0.7529	Intermediate Similarity	NPC194411
0.7529	Intermediate Similarity	NPC88110
0.7515	Intermediate Similarity	NPC54988
0.7515	Intermediate Similarity	NPC469785
0.7515	Intermediate Similarity	NPC160105
0.7515	Intermediate Similarity	NPC109447
0.7514	Intermediate Similarity	NPC248454
0.7514	Intermediate Similarity	NPC68354
0.75	Intermediate Similarity	NPC472586
0.75	Intermediate Similarity	NPC478182
0.75	Intermediate Similarity	NPC311276
0.75	Intermediate Similarity	NPC96102
0.75	Intermediate Similarity	NPC29886
0.75	Intermediate Similarity	NPC261195
0.75	Intermediate Similarity	NPC470497
0.7486	Intermediate Similarity	NPC314394
0.7486	Intermediate Similarity	NPC324091
0.7486	Intermediate Similarity	NPC171317
0.7485	Intermediate Similarity	NPC131718
0.7471	Intermediate Similarity	NPC317430
0.7471	Intermediate Similarity	NPC154293
0.7471	Intermediate Similarity	NPC213468
0.7471	Intermediate Similarity	NPC248041
0.7471	Intermediate Similarity	NPC265710
0.7471	Intermediate Similarity	NPC126709
0.7471	Intermediate Similarity	NPC201700
0.7469	Intermediate Similarity	NPC21605
0.7469	Intermediate Similarity	NPC179787
0.7469	Intermediate Similarity	NPC201380
0.7468	Intermediate Similarity	NPC312092
0.7468	Intermediate Similarity	NPC110126
0.7468	Intermediate Similarity	NPC104483
0.7458	Intermediate Similarity	NPC476319
0.7458	Intermediate Similarity	NPC99939
0.7458	Intermediate Similarity	NPC308931
0.7456	Intermediate Similarity	NPC115232
0.7452	Intermediate Similarity	NPC105127
0.7443	Intermediate Similarity	NPC470205
0.7442	Intermediate Similarity	NPC472123
0.744	Intermediate Similarity	NPC214106
0.7432	Intermediate Similarity	NPC141454
0.7423	Intermediate Similarity	NPC321911
0.7414	Intermediate Similarity	NPC473380
0.7414	Intermediate Similarity	NPC240088
0.7414	Intermediate Similarity	NPC145885
0.7414	Intermediate Similarity	NPC59269
0.7414	Intermediate Similarity	NPC84827
0.7414	Intermediate Similarity	NPC14113
0.7407	Intermediate Similarity	NPC143872
0.7407	Intermediate Similarity	NPC63545
0.7401	Intermediate Similarity	NPC470003
0.7401	Intermediate Similarity	NPC21429
0.7399	Intermediate Similarity	NPC275305
0.7399	Intermediate Similarity	NPC37423
0.7396	Intermediate Similarity	NPC40779
0.7396	Intermediate Similarity	NPC478184
0.7391	Intermediate Similarity	NPC473640
0.7389	Intermediate Similarity	NPC206967
0.7378	Intermediate Similarity	NPC148592
0.7378	Intermediate Similarity	NPC53947
0.7371	Intermediate Similarity	NPC72980
0.7371	Intermediate Similarity	NPC283219
0.7366	Intermediate Similarity	NPC300183
0.7365	Intermediate Similarity	NPC286427
0.7362	Intermediate Similarity	NPC469811
0.736	Intermediate Similarity	NPC280290
0.736	Intermediate Similarity	NPC15102
0.7356	Intermediate Similarity	NPC267885
0.7351	Intermediate Similarity	NPC293917

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 NPC299594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	635
0.2-0.3	949
0.3-0.4	1687
0.4-0.5	2570
0.5-0.6	2353
0.6-0.7	618
0.7-0.8	79
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8387	Intermediate Similarity	NPD4463	Approved
0.8387	Intermediate Similarity	NPD4462	Approved
0.8081	Intermediate Similarity	NPD3961	Discontinued
0.8081	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD2915	Discontinued
0.7879	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1592	Phase 3
0.7765	Intermediate Similarity	NPD5104	Approved
0.7756	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7619	Phase 3
0.7709	Intermediate Similarity	NPD7618	Phase 3
0.7702	Intermediate Similarity	NPD3835	Phase 3
0.7702	Intermediate Similarity	NPD3833	Phase 3
0.7683	Intermediate Similarity	NPD4326	Phase 2
0.7667	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4075	Phase 2
0.764	Intermediate Similarity	NPD3100	Discontinued
0.761	Intermediate Similarity	NPD5254	Discontinued
0.7605	Intermediate Similarity	NPD5138	Approved
0.7605	Intermediate Similarity	NPD5140	Approved
0.758	Intermediate Similarity	NPD786	Approved
0.7564	Intermediate Similarity	NPD1262	Discovery
0.7547	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1325	Approved
0.7529	Intermediate Similarity	NPD1326	Approved
0.7514	Intermediate Similarity	NPD3505	Approved
0.7514	Intermediate Similarity	NPD3506	Approved
0.75	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4128	Approved
0.7485	Intermediate Similarity	NPD2172	Phase 1
0.7484	Intermediate Similarity	NPD5020	Approved
0.7484	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1722	Approved
0.7471	Intermediate Similarity	NPD4079	Approved
0.7471	Intermediate Similarity	NPD4076	Approved
0.7471	Intermediate Similarity	NPD2844	Phase 3
0.7458	Intermediate Similarity	NPD5075	Discontinued
0.7427	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5065	Approved
0.7374	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5021	Discontinued
0.7356	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6248	Phase 2
0.7351	Intermediate Similarity	NPD6249	Phase 2
0.7348	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3654	Approved
0.7333	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6217	Discontinued
0.7301	Intermediate Similarity	NPD1683	Approved
0.7299	Intermediate Similarity	NPD482	Approved
0.7273	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8386	Phase 2
0.7261	Intermediate Similarity	NPD3385	Approved
0.7247	Intermediate Similarity	NPD3319	Phase 1
0.7247	Intermediate Similarity	NPD2094	Phase 2
0.7247	Intermediate Similarity	NPD3318	Approved
0.7247	Intermediate Similarity	NPD3320	Approved
0.7247	Intermediate Similarity	NPD2095	Phase 2
0.7247	Intermediate Similarity	NPD2092	Phase 2
0.7238	Intermediate Similarity	NPD4334	Discontinued
0.7235	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6595	Phase 3
0.7229	Intermediate Similarity	NPD2882	Phase 1
0.7219	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4181	Approved
0.7216	Intermediate Similarity	NPD2144	Approved
0.7209	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2091	Phase 2
0.7207	Intermediate Similarity	NPD2096	Phase 2
0.7198	Intermediate Similarity	NPD4499	Approved
0.7196	Intermediate Similarity	NPD5487	Phase 1
0.7186	Intermediate Similarity	NPD2837	Discontinued
0.7173	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD8322	Phase 2
0.7173	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8272	Phase 2
0.7158	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5596	Phase 2
0.7135	Intermediate Similarity	NPD6452	Discontinued
0.7127	Intermediate Similarity	NPD7026	Phase 2
0.7127	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6158	Phase 2
0.7126	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4047	Discontinued
0.7107	Intermediate Similarity	NPD4880	Discontinued
0.7095	Intermediate Similarity	NPD3038	Discontinued
0.7091	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6448	Phase 1
0.7077	Intermediate Similarity	NPD8093	Discontinued
0.7076	Intermediate Similarity	NPD1404	Approved
0.7076	Intermediate Similarity	NPD1403	Approved
0.7071	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2641	Approved
0.7069	Intermediate Similarity	NPD4638	Approved
0.7069	Intermediate Similarity	NPD4640	Approved
0.7069	Intermediate Similarity	NPD2640	Approved
0.7069	Intermediate Similarity	NPD4639	Approved
0.7059	Intermediate Similarity	NPD6206	Phase 1
0.7059	Intermediate Similarity	NPD5003	Discontinued
0.7059	Intermediate Similarity	NPD6664	Approved
0.7052	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD750	Phase 2
0.7043	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5809	Phase 3
0.7033	Intermediate Similarity	NPD5444	Phase 1
0.7027	Intermediate Similarity	NPD4315	Phase 2
0.7021	Intermediate Similarity	NPD6261	Phase 3
0.7011	Intermediate Similarity	NPD2642	Approved
0.7011	Intermediate Similarity	NPD2639	Approved
0.7006	Intermediate Similarity	NPD6492	Phase 2
0.7006	Intermediate Similarity	NPD947	Approved
0.6995	Remote Similarity	NPD8431	Approved
0.6994	Remote Similarity	NPD3583	Phase 2
0.6994	Remote Similarity	NPD3323	Discontinued
0.6989	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2880	Discontinued
0.6966	Remote Similarity	NPD2382	Approved
0.6966	Remote Similarity	NPD6044	Discontinued
0.6966	Remote Similarity	NPD2381	Approved
0.6966	Remote Similarity	NPD2380	Approved
0.6959	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2720	Phase 1
0.6954	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4602	Approved
0.6944	Remote Similarity	NPD5473	Discontinued
0.6939	Remote Similarity	NPD7470	Discontinued
0.6936	Remote Similarity	NPD6771	Discontinued
0.6935	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6176	Phase 1
0.6923	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7482	Phase 2
0.6923	Remote Similarity	NPD7483	Phase 2
0.6919	Remote Similarity	NPD2565	Phase 2
0.6919	Remote Similarity	NPD2564	Approved
0.6914	Remote Similarity	NPD6554	Approved
0.6914	Remote Similarity	NPD45	Approved
0.6901	Remote Similarity	NPD2580	Discontinued
0.6898	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7716	Approved
0.6897	Remote Similarity	NPD7717	Approved
0.6893	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6828	Phase 2
0.6891	Remote Similarity	NPD5901	Discontinued
0.6891	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7469	Discontinued
0.6882	Remote Similarity	NPD5913	Phase 3
0.6882	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7948	Phase 1
0.6875	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6376	Discontinued
0.6862	Remote Similarity	NPD7944	Discontinued
0.6859	Remote Similarity	NPD4501	Approved
0.6859	Remote Similarity	NPD4500	Approved
0.6859	Remote Similarity	NPD4601	Approved
0.6859	Remote Similarity	NPD4600	Approved
0.6856	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1253	Approved
0.6852	Remote Similarity	NPD1254	Approved
0.6852	Remote Similarity	NPD1256	Approved
0.6852	Remote Similarity	NPD1255	Approved
0.6851	Remote Similarity	NPD5897	Approved
0.6851	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5898	Approved
0.6851	Remote Similarity	NPD5899	Approved
0.6851	Remote Similarity	NPD702	Clinical (unspecified phase)
0.685	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4702	Approved
0.6845	Remote Similarity	NPD1661	Suspended
0.6845	Remote Similarity	NPD4703	Approved
0.6842	Remote Similarity	NPD3405	Phase 3
0.6839	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7603	Discontinued
0.6829	Remote Similarity	NPD680	Discontinued
0.6823	Remote Similarity	NPD4511	Phase 1
0.6818	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1251	Discontinued
0.6813	Remote Similarity	NPD4399	Phase 2
0.6802	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2150	Discontinued
0.6798	Remote Similarity	NPD3609	Approved
0.6798	Remote Similarity	NPD3610	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