NPASS Compound

Structure

NPC27833 OpenBabel07101719132D 21 22 0 0 1 0 0 0 0 0999 V2000 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -1.7321 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 1 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 -0.8660 0.5000 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 -0.8660 -2.5000 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 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 16 2 3 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 1 0 0 0 13 19 2 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.11
Volume:	289.583
LogP:	0.651
LogD:	0.697
LogS:	-2.412
# Rotatable Bonds:	5
TPSA:	91.56
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	2.851
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.015
MDCK Permeability:	1.003323541226564e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.68
Plasma Protein Binding (PPB):	70.1485824584961%
Volume Distribution (VD):	0.78
Pgp-substrate:	25.00632667541504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.432
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.196
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.49
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	7.732
Half-life (T1/2):	0.69

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.119
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.121

Download Data

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

Natural Product: NPC27833

Natural Product ID:	NPC27833
*Common Name:**	Cordiarimide A
IUPAC Name:	N-[(3S)-2,6-dioxo-1-phenacylpiperidin-3-yl]acetamide
Synonyms:
Standard InCHIKey:	ZOUDJLOPMJRMCU-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C15H16N2O4/c1-10(18)16-12-7-8-14(20)17(15(12)21)9-13(19)11-5-3-2-4-6-11/h2-6,12H,7-9H2,1H3,(H,16,18)/t12-/m0/s1
SMILES:	CC(=N[C@H]1CCC(=O)N(CC(=O)c2ccccc2)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097554
PubChem CID:	46831112
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 [CHEMONTID:0001189] N-acyl-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
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19368377]
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384317]
NPO22854	Cordia globifera	Species	Cordiaceae	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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	=	145300.0	nM	PMID[475244]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	54100.0	nM	PMID[475244]

☑ 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 NPC27833 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	134
0.1-0.2	1651
0.2-0.3	8668
0.3-0.4	15114
0.4-0.5	14372
0.5-0.6	2212
0.6-0.7	491
0.7-0.8	54
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8017	Intermediate Similarity	NPC473418
0.7846	Intermediate Similarity	NPC469666
0.7742	Intermediate Similarity	NPC239357
0.7712	Intermediate Similarity	NPC167336
0.7647	Intermediate Similarity	NPC45033
0.76	Intermediate Similarity	NPC315276
0.76	Intermediate Similarity	NPC14672
0.76	Intermediate Similarity	NPC285926
0.754	Intermediate Similarity	NPC470545
0.75	Intermediate Similarity	NPC200964
0.748	Intermediate Similarity	NPC220698
0.748	Intermediate Similarity	NPC470546
0.746	Intermediate Similarity	NPC470544
0.7444	Intermediate Similarity	NPC473322
0.744	Intermediate Similarity	NPC33742
0.7391	Intermediate Similarity	NPC256452
0.736	Intermediate Similarity	NPC276949
0.736	Intermediate Similarity	NPC35850
0.7348	Intermediate Similarity	NPC101719
0.7328	Intermediate Similarity	NPC474082
0.7328	Intermediate Similarity	NPC175726
0.7308	Intermediate Similarity	NPC71684
0.7273	Intermediate Similarity	NPC22746
0.7273	Intermediate Similarity	NPC222466
0.7185	Intermediate Similarity	NPC111428
0.7155	Intermediate Similarity	NPC246757
0.7155	Intermediate Similarity	NPC291070
0.7154	Intermediate Similarity	NPC55529
0.7132	Intermediate Similarity	NPC200589
0.7099	Intermediate Similarity	NPC302169
0.7092	Intermediate Similarity	NPC239762
0.7092	Intermediate Similarity	NPC163392
0.708	Intermediate Similarity	NPC305602
0.708	Intermediate Similarity	NPC17497
0.708	Intermediate Similarity	NPC255447
0.7068	Intermediate Similarity	NPC6975
0.705	Intermediate Similarity	NPC248283
0.7029	Intermediate Similarity	NPC257390
0.7014	Intermediate Similarity	NPC201244
0.7014	Intermediate Similarity	NPC477217
0.7009	Intermediate Similarity	NPC71140
0.6993	Remote Similarity	NPC161069
0.6985	Remote Similarity	NPC319766
0.6957	Remote Similarity	NPC130309
0.6935	Remote Similarity	NPC471447
0.6929	Remote Similarity	NPC474473
0.6923	Remote Similarity	NPC263493
0.6923	Remote Similarity	NPC269398
0.6918	Remote Similarity	NPC135121
0.6917	Remote Similarity	NPC202521
0.6901	Remote Similarity	NPC92784
0.6901	Remote Similarity	NPC476133
0.6901	Remote Similarity	NPC470884
0.6901	Remote Similarity	NPC98424
0.6901	Remote Similarity	NPC178662
0.6901	Remote Similarity	NPC132636
0.6899	Remote Similarity	NPC113099
0.6889	Remote Similarity	NPC285394
0.6884	Remote Similarity	NPC179224
0.6875	Remote Similarity	NPC197682
0.6866	Remote Similarity	NPC252878
0.686	Remote Similarity	NPC12730
0.6855	Remote Similarity	NPC143516
0.6849	Remote Similarity	NPC262077
0.6842	Remote Similarity	NPC476990
0.6829	Remote Similarity	NPC202613
0.6828	Remote Similarity	NPC52748
0.6815	Remote Similarity	NPC46427
0.6812	Remote Similarity	NPC150863
0.6806	Remote Similarity	NPC168113
0.6803	Remote Similarity	NPC138775
0.68	Remote Similarity	NPC474973
0.68	Remote Similarity	NPC130898
0.68	Remote Similarity	NPC474804
0.6781	Remote Similarity	NPC209509
0.6777	Remote Similarity	NPC322598
0.6759	Remote Similarity	NPC139326
0.6757	Remote Similarity	NPC478039
0.6748	Remote Similarity	NPC329375
0.6739	Remote Similarity	NPC305717
0.6736	Remote Similarity	NPC307357
0.6736	Remote Similarity	NPC46098
0.6736	Remote Similarity	NPC476259
0.6736	Remote Similarity	NPC268841
0.6715	Remote Similarity	NPC79698
0.6713	Remote Similarity	NPC68865
0.6713	Remote Similarity	NPC127741
0.6694	Remote Similarity	NPC472258
0.6694	Remote Similarity	NPC471317
0.6694	Remote Similarity	NPC164859
0.6693	Remote Similarity	NPC473676
0.6689	Remote Similarity	NPC473341
0.6667	Remote Similarity	NPC89489
0.6667	Remote Similarity	NPC322433
0.6667	Remote Similarity	NPC242159
0.6667	Remote Similarity	NPC5620
0.6667	Remote Similarity	NPC313694
0.6667	Remote Similarity	NPC473498
0.6645	Remote Similarity	NPC473002
0.6644	Remote Similarity	NPC471820
0.6644	Remote Similarity	NPC176226
0.6644	Remote Similarity	NPC471821
0.6643	Remote Similarity	NPC300315
0.6643	Remote Similarity	NPC472245
0.6643	Remote Similarity	NPC280807
0.6643	Remote Similarity	NPC314431
0.664	Remote Similarity	NPC275467
0.6639	Remote Similarity	NPC473661
0.6623	Remote Similarity	NPC233702
0.662	Remote Similarity	NPC287401
0.6615	Remote Similarity	NPC474584
0.66	Remote Similarity	NPC2501
0.6599	Remote Similarity	NPC476978
0.6597	Remote Similarity	NPC471265
0.6597	Remote Similarity	NPC43755
0.6597	Remote Similarity	NPC471264
0.6589	Remote Similarity	NPC319579
0.6579	Remote Similarity	NPC122590
0.6577	Remote Similarity	NPC145113
0.6577	Remote Similarity	NPC16188
0.6577	Remote Similarity	NPC225648
0.6577	Remote Similarity	NPC329761
0.6554	Remote Similarity	NPC315266
0.6552	Remote Similarity	NPC122553
0.6549	Remote Similarity	NPC473962
0.6547	Remote Similarity	NPC136453
0.6538	Remote Similarity	NPC329011
0.6538	Remote Similarity	NPC154478
0.6538	Remote Similarity	NPC475013
0.6535	Remote Similarity	NPC327481
0.6533	Remote Similarity	NPC105717
0.6533	Remote Similarity	NPC240848
0.6531	Remote Similarity	NPC471164
0.6519	Remote Similarity	NPC189116
0.6519	Remote Similarity	NPC226143
0.6518	Remote Similarity	NPC300205
0.65	Remote Similarity	NPC71933
0.65	Remote Similarity	NPC105114
0.65	Remote Similarity	NPC152850
0.65	Remote Similarity	NPC89923
0.65	Remote Similarity	NPC239990
0.6496	Remote Similarity	NPC26285
0.6494	Remote Similarity	NPC469903
0.6493	Remote Similarity	NPC169328
0.649	Remote Similarity	NPC129666
0.6486	Remote Similarity	NPC314388
0.6486	Remote Similarity	NPC315283
0.6479	Remote Similarity	NPC126458
0.6466	Remote Similarity	NPC197470
0.6463	Remote Similarity	NPC469426
0.6463	Remote Similarity	NPC469427
0.646	Remote Similarity	NPC164086
0.6457	Remote Similarity	NPC476198
0.6457	Remote Similarity	NPC67043
0.6456	Remote Similarity	NPC471051
0.6456	Remote Similarity	NPC471053
0.6456	Remote Similarity	NPC471052
0.6447	Remote Similarity	NPC324081
0.6446	Remote Similarity	NPC474974
0.6444	Remote Similarity	NPC310467
0.6443	Remote Similarity	NPC316008
0.6443	Remote Similarity	NPC313867
0.6443	Remote Similarity	NPC478040
0.6443	Remote Similarity	NPC471680
0.6439	Remote Similarity	NPC476048
0.6434	Remote Similarity	NPC246079
0.6434	Remote Similarity	NPC40364
0.6434	Remote Similarity	NPC325479
0.6434	Remote Similarity	NPC207428
0.6433	Remote Similarity	NPC469902
0.6433	Remote Similarity	NPC473003
0.6433	Remote Similarity	NPC469901
0.6429	Remote Similarity	NPC2785
0.6429	Remote Similarity	NPC285470
0.6429	Remote Similarity	NPC36342
0.6429	Remote Similarity	NPC477937
0.6424	Remote Similarity	NPC246412
0.6415	Remote Similarity	NPC138293
0.6415	Remote Similarity	NPC113056
0.641	Remote Similarity	NPC84317
0.64	Remote Similarity	NPC314186
0.64	Remote Similarity	NPC314358
0.6397	Remote Similarity	NPC291962
0.6397	Remote Similarity	NPC177684
0.6393	Remote Similarity	NPC303045
0.6393	Remote Similarity	NPC161972
0.6385	Remote Similarity	NPC158854
0.6382	Remote Similarity	NPC283783
0.6369	Remote Similarity	NPC62104
0.6369	Remote Similarity	NPC1390
0.6364	Remote Similarity	NPC202198
0.6364	Remote Similarity	NPC14849
0.6364	Remote Similarity	NPC120251
0.6364	Remote Similarity	NPC286551
0.6364	Remote Similarity	NPC157311
0.6357	Remote Similarity	NPC470343
0.6357	Remote Similarity	NPC472244
0.6356	Remote Similarity	NPC69057
0.635	Remote Similarity	NPC258531
0.635	Remote Similarity	NPC161956

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 NPC27833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	110
0.1-0.2	480
0.2-0.3	903
0.3-0.4	2333
0.4-0.5	3448
0.5-0.6	1475
0.6-0.7	360
0.7-0.8	41
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8036	Intermediate Similarity	NPD1099	Approved
0.8036	Intermediate Similarity	NPD1100	Approved
0.7879	Intermediate Similarity	NPD941	Approved
0.7607	Intermediate Similarity	NPD2171	Approved
0.7563	Intermediate Similarity	NPD2192	Approved
0.7563	Intermediate Similarity	NPD2197	Approved
0.7561	Intermediate Similarity	NPD480	Approved
0.7537	Intermediate Similarity	NPD2846	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD1323	Discontinued
0.7481	Intermediate Similarity	NPD1482	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2648	Phase 3
0.7458	Intermediate Similarity	NPD2193	Phase 2
0.7458	Intermediate Similarity	NPD4803	Discontinued
0.7444	Intermediate Similarity	NPD1781	Discontinued
0.7381	Intermediate Similarity	NPD1025	Discontinued
0.7364	Intermediate Similarity	NPD4733	Approved
0.7353	Intermediate Similarity	NPD4540	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3581	Discontinued
0.7313	Intermediate Similarity	NPD3626	Phase 3
0.7311	Intermediate Similarity	NPD813	Approved
0.7302	Intermediate Similarity	NPD3551	Approved
0.7273	Intermediate Similarity	NPD3547	Approved
0.7273	Intermediate Similarity	NPD3549	Approved
0.7273	Intermediate Similarity	NPD3550	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD3624	Phase 2
0.7252	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3519	Discontinued
0.7218	Intermediate Similarity	NPD2634	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2584	Suspended
0.7197	Intermediate Similarity	NPD6408	Phase 1
0.7172	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6024	Approved
0.7167	Intermediate Similarity	NPD6027	Approved
0.7143	Intermediate Similarity	NPD4677	Discontinued
0.7111	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6806	Phase 1
0.709	Intermediate Similarity	NPD2031	Discontinued
0.7073	Intermediate Similarity	NPD7130	Phase 3
0.7063	Intermediate Similarity	NPD753	Approved
0.7059	Intermediate Similarity	NPD466	Approved
0.7037	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2196	Discontinued
0.7023	Intermediate Similarity	NPD1217	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4185	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD742	Approved
0.7	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7720	Phase 2
0.6993	Remote Similarity	NPD2010	Phase 3
0.6992	Remote Similarity	NPD1767	Approved
0.6992	Remote Similarity	NPD1765	Approved
0.6992	Remote Similarity	NPD1766	Approved
0.6992	Remote Similarity	NPD1763	Approved
0.6992	Remote Similarity	NPD1761	Approved
0.6985	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4655	Approved
0.6975	Remote Similarity	NPD4657	Approved
0.697	Remote Similarity	NPD5836	Discontinued
0.6967	Remote Similarity	NPD3357	Discontinued
0.6963	Remote Similarity	NPD3125	Approved
0.6957	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.695	Remote Similarity	NPD8173	Phase 2
0.695	Remote Similarity	NPD8172	Phase 2
0.6947	Remote Similarity	NPD6343	Approved
0.6947	Remote Similarity	NPD6345	Approved
0.694	Remote Similarity	NPD3071	Approved
0.694	Remote Similarity	NPD3073	Approved
0.694	Remote Similarity	NPD3072	Approved
0.6929	Remote Similarity	NPD2124	Approved
0.6917	Remote Similarity	NPD1123	Approved
0.6917	Remote Similarity	NPD1079	Discontinued
0.6917	Remote Similarity	NPD1124	Approved
0.6912	Remote Similarity	NPD1321	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5581	Approved
0.6901	Remote Similarity	NPD7541	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD853	Approved
0.6899	Remote Similarity	NPD1074	Approved
0.6899	Remote Similarity	NPD1073	Approved
0.6899	Remote Similarity	NPD1075	Approved
0.6899	Remote Similarity	NPD851	Approved
0.6892	Remote Similarity	NPD979	Approved
0.6892	Remote Similarity	NPD4942	Approved
0.6889	Remote Similarity	NPD5159	Phase 2
0.6889	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5157	Phase 1
0.687	Remote Similarity	NPD5991	Approved
0.687	Remote Similarity	NPD5990	Approved
0.6866	Remote Similarity	NPD4762	Approved
0.6866	Remote Similarity	NPD4761	Approved
0.6861	Remote Similarity	NPD4151	Approved
0.6861	Remote Similarity	NPD3588	Discontinued
0.6855	Remote Similarity	NPD1677	Discontinued
0.6853	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7142	Discontinued
0.6842	Remote Similarity	NPD1727	Approved
0.6842	Remote Similarity	NPD951	Approved
0.6838	Remote Similarity	NPD6792	Phase 3
0.6831	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1077	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4094	Approved
0.6803	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8323	Discontinued
0.6803	Remote Similarity	NPD7575	Phase 3
0.6803	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7679	Phase 2
0.6783	Remote Similarity	NPD4214	Discontinued
0.6783	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3867	Phase 2
0.6767	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5263	Approved
0.6763	Remote Similarity	NPD4125	Approved
0.6761	Remote Similarity	NPD3908	Approved
0.6757	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5918	Discontinued
0.672	Remote Similarity	NPD999	Phase 2
0.6716	Remote Similarity	NPD3064	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD2056	Discontinued
0.6715	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD5578	Approved
0.6714	Remote Similarity	NPD1619	Phase 3
0.6714	Remote Similarity	NPD2754	Discontinued
0.6713	Remote Similarity	NPD5004	Approved
0.6692	Remote Similarity	NPD998	Approved
0.6691	Remote Similarity	NPD1050	Approved
0.6691	Remote Similarity	NPD4175	Approved
0.6691	Remote Similarity	NPD4177	Approved
0.6691	Remote Similarity	NPD3040	Approved
0.669	Remote Similarity	NPD5296	Approved
0.6667	Remote Similarity	NPD1344	Phase 2
0.6667	Remote Similarity	NPD9540	Approved
0.6667	Remote Similarity	NPD5653	Discontinued
0.6667	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6294	Approved
0.6667	Remote Similarity	NPD6901	Phase 3
0.6667	Remote Similarity	NPD6295	Approved
0.6644	Remote Similarity	NPD4461	Discontinued
0.6644	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3063	Discontinued
0.6643	Remote Similarity	NPD4676	Approved
0.6643	Remote Similarity	NPD3577	Discontinued
0.6641	Remote Similarity	NPD2508	Discontinued
0.6623	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5748	Phase 2
0.6622	Remote Similarity	NPD1967	Approved
0.6622	Remote Similarity	NPD1968	Approved
0.6621	Remote Similarity	NPD7254	Discontinued
0.6619	Remote Similarity	NPD3578	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1948	Approved
0.6617	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6039	Approved
0.6594	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3644	Approved
0.6589	Remote Similarity	NPD3642	Approved
0.6589	Remote Similarity	NPD3643	Approved
0.6577	Remote Similarity	NPD6017	Discontinued
0.6573	Remote Similarity	NPD6623	Phase 3
0.6573	Remote Similarity	NPD5272	Discontinued
0.6571	Remote Similarity	NPD4549	Discontinued
0.6554	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1330	Phase 2
0.6544	Remote Similarity	NPD1947	Approved
0.6528	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9539	Approved
0.6522	Remote Similarity	NPD9541	Approved
0.6513	Remote Similarity	NPD3822	Approved
0.6513	Remote Similarity	NPD3820	Approved
0.6513	Remote Similarity	NPD3821	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD1724	Approved
0.6503	Remote Similarity	NPD1527	Phase 2
0.65	Remote Similarity	NPD4980	Approved
0.649	Remote Similarity	NPD3282	Phase 1
0.649	Remote Similarity	NPD6088	Approved
0.649	Remote Similarity	NPD7088	Discontinued
0.649	Remote Similarity	NPD3283	Phase 3
0.6486	Remote Similarity	NPD6681	Discovery
0.6486	Remote Similarity	NPD6566	Discontinued
0.6483	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6073	Approved
0.6483	Remote Similarity	NPD7192	Discontinued
0.6475	Remote Similarity	NPD6325	Discontinued
0.6474	Remote Similarity	NPD7011	Discontinued
0.6474	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3221	Clinical (unspecified phase)

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