NPASS Compound

Structure

NPC165495 OpenBabel07101719402D 25 27 0 0 1 0 0 0 0 0999 V2000 5.0131 2.5169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3003 1.3579 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 3.9328 -2.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6019 -1.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9546 -2.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6530 0.8227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9620 -0.1284 0.0000 C 0 0 0 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 1.8366 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3221 1.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2929 -0.8715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3147 -0.6636 0.0000 C 0 0 0 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 2.8147 0.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 19 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 18 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	341.17
Volume:	352.417
LogP:	3.214
LogD:	1.939
LogS:	-3.005
# Rotatable Bonds:	4
TPSA:	85.43
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	3.768
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.933
MDCK Permeability:	2.957594915642403e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.692

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838
Plasma Protein Binding (PPB):	87.54367065429688%
Volume Distribution (VD):	0.699
Pgp-substrate:	8.991218566894531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.264
CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.125
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.186
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.761
CYP3A4-substrate:	0.32

ADMET: Excretion

Clearance (CL):	8.663
Half-life (T1/2):	0.719

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.888
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.496
Maximum Recommended Daily Dose:	0.474
Skin Sensitization:	0.141
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.163

Download Data

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

Natural Product: NPC165495

Natural Product ID:	NPC165495
*Common Name:**	14-Hydroxyterezine D
IUPAC Name:	(3S,6S)-1-hydroxy-3-methyl-6-[[7-(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]piperazine-2,5-dione
Synonyms:	14-Hydroxyterezine D
Standard InCHIKey:	UDQXPGDOXIBTDM-LRDDRELGSA-N
Standard InCHI:	InChI=1S/C19H23N3O3/c1-11(2)7-8-13-5-4-6-15-14(10-20-17(13)15)9-16-18(23)21-12(3)19(24)22(16)25/h4-7,10,12,16,20,25H,8-9H2,1-3H3,(H,21,23)/t12-,16-/m0/s1
SMILES:	CC(=CCc1cccc2c1[nH]cc2C[C@H]1C(=N[C@H](C(=O)N1O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487280
PubChem CID:	24900165
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
NPO32792	aspergillus sydowi	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7310.0	nM	PMID[534775]

☑ 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 NPC165495 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	358
0.1-0.2	3348
0.2-0.3	18157
0.3-0.4	13614
0.4-0.5	2847
0.5-0.6	2448
0.6-0.7	1416
0.7-0.8	418
0.8-0.85	75
0.85-0.9	14
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9141	High Similarity	NPC194640
0.8857	High Similarity	NPC213629
0.8844	High Similarity	NPC228835
0.8802	High Similarity	NPC474561
0.8802	High Similarity	NPC49954
0.88	High Similarity	NPC17059
0.8785	High Similarity	NPC470497
0.8778	High Similarity	NPC470499
0.8743	High Similarity	NPC94752
0.8735	High Similarity	NPC282231
0.8721	High Similarity	NPC11126
0.8675	High Similarity	NPC279918
0.8639	High Similarity	NPC63751
0.8471	Intermediate Similarity	NPC54988
0.8471	Intermediate Similarity	NPC160105
0.847	Intermediate Similarity	NPC171317
0.847	Intermediate Similarity	NPC473640
0.8444	Intermediate Similarity	NPC117244
0.8444	Intermediate Similarity	NPC473763
0.8434	Intermediate Similarity	NPC207726
0.8424	Intermediate Similarity	NPC293917
0.8424	Intermediate Similarity	NPC100321
0.84	Intermediate Similarity	NPC248041
0.84	Intermediate Similarity	NPC126709
0.8391	Intermediate Similarity	NPC267885
0.8352	Intermediate Similarity	NPC91179
0.8343	Intermediate Similarity	NPC59269
0.8343	Intermediate Similarity	NPC248454
0.8333	Intermediate Similarity	NPC475506
0.8333	Intermediate Similarity	NPC203468
0.8333	Intermediate Similarity	NPC110500
0.8333	Intermediate Similarity	NPC149155
0.8295	Intermediate Similarity	NPC283219
0.8289	Intermediate Similarity	NPC155143
0.8284	Intermediate Similarity	NPC67056
0.8276	Intermediate Similarity	NPC314603
0.8263	Intermediate Similarity	NPC469765
0.8263	Intermediate Similarity	NPC469760
0.8263	Intermediate Similarity	NPC259644
0.8263	Intermediate Similarity	NPC73952
0.8263	Intermediate Similarity	NPC469786
0.8263	Intermediate Similarity	NPC25008
0.8263	Intermediate Similarity	NPC469763
0.8239	Intermediate Similarity	NPC145885
0.8239	Intermediate Similarity	NPC84827
0.8239	Intermediate Similarity	NPC14113
0.8222	Intermediate Similarity	NPC235684
0.8214	Intermediate Similarity	NPC70922
0.8214	Intermediate Similarity	NPC80597
0.8214	Intermediate Similarity	NPC212376
0.8214	Intermediate Similarity	NPC75540
0.8214	Intermediate Similarity	NPC211572
0.8201	Intermediate Similarity	NPC473376
0.8187	Intermediate Similarity	NPC16667
0.8167	Intermediate Similarity	NPC15102
0.8166	Intermediate Similarity	NPC285469
0.8163	Intermediate Similarity	NPC477714
0.8156	Intermediate Similarity	NPC163055
0.8132	Intermediate Similarity	NPC321708
0.8125	Intermediate Similarity	NPC478158
0.8122	Intermediate Similarity	NPC474707
0.8118	Intermediate Similarity	NPC469762
0.8115	Intermediate Similarity	NPC54420
0.8112	Intermediate Similarity	NPC477715
0.8108	Intermediate Similarity	NPC294693
0.8103	Intermediate Similarity	NPC78020
0.8101	Intermediate Similarity	NPC233936
0.8093	Intermediate Similarity	NPC153980
0.8093	Intermediate Similarity	NPC6865
0.8092	Intermediate Similarity	NPC470508
0.809	Intermediate Similarity	NPC213468
0.8077	Intermediate Similarity	NPC317030
0.8077	Intermediate Similarity	NPC204565
0.8059	Intermediate Similarity	NPC469785
0.8041	Intermediate Similarity	NPC72956
0.8035	Intermediate Similarity	NPC311276
0.8033	Intermediate Similarity	NPC65215
0.8033	Intermediate Similarity	NPC173028
0.8031	Intermediate Similarity	NPC107077
0.8031	Intermediate Similarity	NPC162860
0.8031	Intermediate Similarity	NPC223791
0.8012	Intermediate Similarity	NPC314372
0.8	Intermediate Similarity	NPC201700
0.8	Intermediate Similarity	NPC110602
0.8	Intermediate Similarity	NPC75726
0.8	Intermediate Similarity	NPC471193
0.8	Intermediate Similarity	NPC31385
0.8	Intermediate Similarity	NPC75634
0.8	Intermediate Similarity	NPC471194
0.7989	Intermediate Similarity	NPC219336
0.7955	Intermediate Similarity	NPC280548
0.7949	Intermediate Similarity	NPC320968
0.7946	Intermediate Similarity	NPC243716
0.7933	Intermediate Similarity	NPC15573
0.7933	Intermediate Similarity	NPC183662
0.7933	Intermediate Similarity	NPC217372
0.7931	Intermediate Similarity	NPC271734
0.7919	Intermediate Similarity	NPC478157
0.7907	Intermediate Similarity	NPC299594
0.7892	Intermediate Similarity	NPC190296
0.7879	Intermediate Similarity	NPC471192
0.787	Intermediate Similarity	NPC187951
0.7868	Intermediate Similarity	NPC54744
0.7861	Intermediate Similarity	NPC230869
0.7861	Intermediate Similarity	NPC474177
0.7853	Intermediate Similarity	NPC194411
0.7833	Intermediate Similarity	NPC68354
0.7831	Intermediate Similarity	NPC262898
0.7829	Intermediate Similarity	NPC40779
0.7824	Intermediate Similarity	NPC24678
0.7824	Intermediate Similarity	NPC105818
0.7821	Intermediate Similarity	NPC469938
0.7821	Intermediate Similarity	NPC472586
0.7819	Intermediate Similarity	NPC133366
0.7807	Intermediate Similarity	NPC473342
0.7807	Intermediate Similarity	NPC477167
0.78	Intermediate Similarity	NPC281049
0.779	Intermediate Similarity	NPC248462
0.779	Intermediate Similarity	NPC55772
0.7778	Intermediate Similarity	NPC179701
0.7772	Intermediate Similarity	NPC99939
0.7772	Intermediate Similarity	NPC308931
0.776	Intermediate Similarity	NPC300183
0.7747	Intermediate Similarity	NPC469896
0.7737	Intermediate Similarity	NPC229332
0.7735	Intermediate Similarity	NPC151939
0.7735	Intermediate Similarity	NPC111275
0.7735	Intermediate Similarity	NPC64436
0.7733	Intermediate Similarity	NPC200214
0.773	Intermediate Similarity	NPC62749
0.7722	Intermediate Similarity	NPC275305
0.7722	Intermediate Similarity	NPC37423
0.772	Intermediate Similarity	NPC476874
0.7714	Intermediate Similarity	NPC131718
0.7705	Intermediate Similarity	NPC71037
0.7701	Intermediate Similarity	NPC95783
0.7692	Intermediate Similarity	NPC472443
0.7692	Intermediate Similarity	NPC470440
0.7692	Intermediate Similarity	NPC159856
0.7688	Intermediate Similarity	NPC38736
0.7684	Intermediate Similarity	NPC11445
0.7677	Intermediate Similarity	NPC54981
0.7667	Intermediate Similarity	NPC34508
0.7665	Intermediate Similarity	NPC469767
0.7665	Intermediate Similarity	NPC469784
0.7665	Intermediate Similarity	NPC469761
0.7665	Intermediate Similarity	NPC469768
0.7665	Intermediate Similarity	NPC469779
0.7665	Intermediate Similarity	NPC469783
0.7665	Intermediate Similarity	NPC469780
0.7661	Intermediate Similarity	NPC37548
0.765	Intermediate Similarity	NPC300688
0.7647	Intermediate Similarity	NPC155444
0.7644	Intermediate Similarity	NPC227582
0.7632	Intermediate Similarity	NPC157828
0.7632	Intermediate Similarity	NPC195239
0.7629	Intermediate Similarity	NPC193761
0.7619	Intermediate Similarity	NPC469766
0.7617	Intermediate Similarity	NPC23420
0.7617	Intermediate Similarity	NPC205254
0.7617	Intermediate Similarity	NPC303820
0.7617	Intermediate Similarity	NPC106771
0.7611	Intermediate Similarity	NPC470498
0.761	Intermediate Similarity	NPC64216
0.7605	Intermediate Similarity	NPC73767
0.7602	Intermediate Similarity	NPC471957
0.76	Intermediate Similarity	NPC129721
0.7596	Intermediate Similarity	NPC176199
0.7596	Intermediate Similarity	NPC215795
0.759	Intermediate Similarity	NPC84911
0.7577	Intermediate Similarity	NPC52909
0.7577	Intermediate Similarity	NPC475935
0.7577	Intermediate Similarity	NPC94211
0.7569	Intermediate Similarity	NPC472123
0.7568	Intermediate Similarity	NPC472444
0.7568	Intermediate Similarity	NPC469358
0.7568	Intermediate Similarity	NPC48938
0.7563	Intermediate Similarity	NPC323927
0.7557	Intermediate Similarity	NPC206819
0.7557	Intermediate Similarity	NPC135141
0.7557	Intermediate Similarity	NPC92796
0.7557	Intermediate Similarity	NPC318065
0.7554	Intermediate Similarity	NPC16659
0.7543	Intermediate Similarity	NPC141353
0.7541	Intermediate Similarity	NPC293472
0.754	Intermediate Similarity	NPC315555
0.7536	Intermediate Similarity	NPC24370
0.7536	Intermediate Similarity	NPC319232
0.753	Intermediate Similarity	NPC29886
0.753	Intermediate Similarity	NPC96102
0.753	Intermediate Similarity	NPC261195
0.7528	Intermediate Similarity	NPC102423
0.7528	Intermediate Similarity	NPC478182
0.7526	Intermediate Similarity	NPC304187
0.7526	Intermediate Similarity	NPC252338
0.7526	Intermediate Similarity	NPC477166
0.7525	Intermediate Similarity	NPC71238
0.7524	Intermediate Similarity	NPC89987
0.7514	Intermediate Similarity	NPC6982
0.7513	Intermediate Similarity	NPC131887

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 NPC165495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	526
0.2-0.3	1032
0.3-0.4	1608
0.4-0.5	2583
0.5-0.6	2279
0.6-0.7	786
0.7-0.8	117
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD4184	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD482	Approved
0.8286	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD2092	Phase 2
0.8258	Intermediate Similarity	NPD2094	Phase 2
0.8258	Intermediate Similarity	NPD2095	Phase 2
0.8212	Intermediate Similarity	NPD2091	Phase 2
0.8212	Intermediate Similarity	NPD2096	Phase 2
0.8211	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD8272	Phase 2
0.8177	Intermediate Similarity	NPD3961	Discontinued
0.8156	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD6595	Phase 3
0.8083	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD4075	Phase 2
0.8077	Intermediate Similarity	NPD8431	Approved
0.8068	Intermediate Similarity	NPD750	Phase 2
0.8066	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2144	Approved
0.7914	Intermediate Similarity	NPD7618	Phase 3
0.7914	Intermediate Similarity	NPD7944	Discontinued
0.7914	Intermediate Similarity	NPD7619	Phase 3
0.7889	Intermediate Similarity	NPD4076	Approved
0.7889	Intermediate Similarity	NPD4079	Approved
0.787	Intermediate Similarity	NPD3100	Discontinued
0.7839	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD3505	Approved
0.7833	Intermediate Similarity	NPD3506	Approved
0.7817	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD3038	Discontinued
0.78	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7470	Discontinued
0.7744	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8093	Discontinued
0.7722	Intermediate Similarity	NPD4128	Approved
0.7722	Intermediate Similarity	NPD5065	Approved
0.7711	Intermediate Similarity	NPD786	Approved
0.7692	Intermediate Similarity	NPD7957	Phase 1
0.7692	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8386	Phase 2
0.7692	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD7271	Approved
0.7654	Intermediate Similarity	NPD1326	Approved
0.7654	Intermediate Similarity	NPD1325	Approved
0.7641	Intermediate Similarity	NPD5901	Discontinued
0.7641	Intermediate Similarity	NPD5426	Phase 3
0.7629	Intermediate Similarity	NPD8073	Approved
0.7626	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD8072	Approved
0.7585	Intermediate Similarity	NPD7731	Approved
0.7585	Intermediate Similarity	NPD7730	Approved
0.7562	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7970	Approved
0.7558	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6217	Discontinued
0.753	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1722	Approved
0.7514	Intermediate Similarity	NPD2172	Phase 1
0.7514	Intermediate Similarity	NPD4462	Approved
0.7514	Intermediate Similarity	NPD4463	Approved
0.7512	Intermediate Similarity	NPD7824	Approved
0.75	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4640	Approved
0.75	Intermediate Similarity	NPD4639	Approved
0.75	Intermediate Similarity	NPD4638	Approved
0.7487	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD5017	Discontinued
0.7486	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7780	Approved
0.7464	Intermediate Similarity	NPD7781	Approved
0.7461	Intermediate Similarity	NPD7948	Phase 1
0.7461	Intermediate Similarity	NPD6664	Approved
0.746	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7711	Discontinued
0.745	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD4181	Approved
0.7436	Intermediate Similarity	NPD484	Approved
0.7426	Intermediate Similarity	NPD8094	Discontinued
0.7406	Intermediate Similarity	NPD7952	Approved
0.7406	Intermediate Similarity	NPD7791	Approved
0.7406	Intermediate Similarity	NPD7950	Approved
0.7406	Intermediate Similarity	NPD7953	Approved
0.7406	Intermediate Similarity	NPD7789	Approved
0.7406	Intermediate Similarity	NPD7790	Approved
0.7406	Intermediate Similarity	NPD7951	Approved
0.7387	Intermediate Similarity	NPD8322	Phase 2
0.7382	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7603	Discontinued
0.7366	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4922	Phase 2
0.734	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD1403	Approved
0.7318	Intermediate Similarity	NPD1404	Approved
0.7317	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2641	Approved
0.7308	Intermediate Similarity	NPD2640	Approved
0.7304	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4702	Approved
0.7299	Intermediate Similarity	NPD4703	Approved
0.7293	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD2639	Approved
0.7253	Intermediate Similarity	NPD2642	Approved
0.7247	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4499	Approved
0.7238	Intermediate Similarity	NPD3323	Discontinued
0.7216	Intermediate Similarity	NPD1038	Approved
0.7216	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5100	Phase 3
0.72	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6771	Discontinued
0.7173	Intermediate Similarity	NPD706	Phase 1
0.7172	Intermediate Similarity	NPD4601	Approved
0.7172	Intermediate Similarity	NPD4600	Approved
0.7171	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3404	Approved
0.7158	Intermediate Similarity	NPD7564	Discontinued
0.715	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5117	Phase 2
0.715	Intermediate Similarity	NPD3321	Discontinued
0.7143	Intermediate Similarity	NPD3583	Phase 2
0.7135	Intermediate Similarity	NPD2837	Discontinued
0.7135	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5555	Phase 1
0.712	Intermediate Similarity	NPD5021	Discontinued
0.7102	Intermediate Similarity	NPD1661	Suspended
0.7083	Intermediate Similarity	NPD7026	Phase 2
0.7077	Intermediate Similarity	NPD6665	Discontinued
0.7069	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6178	Phase 3
0.7065	Intermediate Similarity	NPD5487	Phase 1
0.7062	Intermediate Similarity	NPD2565	Phase 2
0.7062	Intermediate Similarity	NPD2564	Approved
0.7056	Intermediate Similarity	NPD2580	Discontinued
0.7053	Intermediate Similarity	NPD3178	Discontinued
0.7049	Intermediate Similarity	NPD5140	Approved
0.7049	Intermediate Similarity	NPD5138	Approved
0.7047	Intermediate Similarity	NPD4948	Discontinued
0.7045	Intermediate Similarity	NPD1683	Approved
0.7043	Intermediate Similarity	NPD3609	Approved
0.7043	Intermediate Similarity	NPD3610	Approved
0.7041	Intermediate Similarity	NPD802	Phase 2
0.7035	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6999	Discontinued
0.7033	Intermediate Similarity	NPD2511	Approved
0.7031	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5254	Discontinued
0.7027	Intermediate Similarity	NPD2844	Phase 3
0.7026	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6044	Discontinued
0.7017	Intermediate Similarity	NPD4326	Phase 2
0.7016	Intermediate Similarity	NPD5105	Approved
0.7016	Intermediate Similarity	NPD5106	Approved
0.7015	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2915	Discontinued
0.701	Intermediate Similarity	NPD7665	Phase 2
0.701	Intermediate Similarity	NPD7666	Phase 3
0.7006	Intermediate Similarity	NPD4547	Phase 3
0.7005	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4427	Phase 2
0.7	Intermediate Similarity	NPD2809	Approved
0.6995	Remote Similarity	NPD7001	Phase 3
0.6995	Remote Similarity	NPD8026	Phase 1
0.699	Remote Similarity	NPD5505	Discontinued
0.6986	Remote Similarity	NPD5818	Discontinued
0.6985	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2882	Phase 1
0.698	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4886	Phase 2
0.6978	Remote Similarity	NPD5255	Approved
0.6976	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6248	Phase 2
0.695	Remote Similarity	NPD6249	Phase 2
0.6948	Remote Similarity	NPD6850	Phase 2
0.6948	Remote Similarity	NPD6849	Phase 2
0.6948	Remote Similarity	NPD6173	Approved
0.6948	Remote Similarity	NPD7716	Approved
0.6948	Remote Similarity	NPD7717	Approved
0.6936	Remote Similarity	NPD2896	Discontinued
0.6935	Remote Similarity	NPD6206	Phase 1

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