NPASS Compound

Structure

NPC469666 OpenBabel07101718222D 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 1 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 1 1 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:	290.13
Volume:	292.219
LogP:	0.254
LogD:	0.121
LogS:	-2.924
# Rotatable Bonds:	5
TPSA:	94.72
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	3.226
Fsp3:	0.267
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:	-5.241
MDCK Permeability:	6.16065744907246e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.073
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	61.45802307128906%
Volume Distribution (VD):	0.829
Pgp-substrate:	37.18934631347656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.212
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.556
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	5.769
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.559
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.119
Carcinogencity:	0.342
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.258

Download Data

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

Natural Product: NPC469666

Natural Product ID:	NPC469666
*Common Name:**	Cordiarimide B
IUPAC Name:	N-[(3S)-1-[(2R)-2-hydroxy-2-phenylethyl]-2,6-dioxopiperidin-3-yl]acetamide
Synonyms:
Standard InCHIKey:	YQYLRDKSRBISRH-STQMWFEESA-N
Standard InCHI:	InChI=1S/C15H18N2O4/c1-10(18)16-12-7-8-14(20)17(15(12)21)9-13(19)11-5-3-2-4-6-11/h2-6,12-13,19H,7-9H2,1H3,(H,16,18)/t12-,13-/m0/s1
SMILES:	CC(=O)NC1CCC(=O)N(C1=O)CC(C2=CC=CC=C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097555
PubChem CID:	46887933
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
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	=	44500.0	nM	PMID[456407]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	21700.0	nM	PMID[456407]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	54.0	%	PMID[456407]

☑ 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 NPC469666 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	689
0.2-0.3	4076
0.3-0.4	13277
0.4-0.5	18461
0.5-0.6	4940
0.6-0.7	816
0.7-0.8	301
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8031	Intermediate Similarity	NPC470545
0.7969	Intermediate Similarity	NPC470546
0.7953	Intermediate Similarity	NPC470544
0.7939	Intermediate Similarity	NPC6975
0.7914	Intermediate Similarity	NPC163392
0.7914	Intermediate Similarity	NPC239762
0.7863	Intermediate Similarity	NPC252878
0.7846	Intermediate Similarity	NPC27833
0.7836	Intermediate Similarity	NPC319766
0.7808	Intermediate Similarity	NPC473341
0.7803	Intermediate Similarity	NPC474082
0.7803	Intermediate Similarity	NPC46427
0.7803	Intermediate Similarity	NPC175726
0.7786	Intermediate Similarity	NPC202521
0.7762	Intermediate Similarity	NPC81026
0.775	Intermediate Similarity	NPC228400
0.775	Intermediate Similarity	NPC214200
0.7737	Intermediate Similarity	NPC257390
0.7714	Intermediate Similarity	NPC242159
0.7714	Intermediate Similarity	NPC313694
0.7712	Intermediate Similarity	NPC294516
0.7712	Intermediate Similarity	NPC107938
0.771	Intermediate Similarity	NPC476990
0.7692	Intermediate Similarity	NPC266741
0.7687	Intermediate Similarity	NPC262166
0.7687	Intermediate Similarity	NPC474479
0.7664	Intermediate Similarity	NPC130309
0.7656	Intermediate Similarity	NPC33742
0.7652	Intermediate Similarity	NPC71684
0.7643	Intermediate Similarity	NPC127741
0.7613	Intermediate Similarity	NPC46009
0.7609	Intermediate Similarity	NPC246079
0.7586	Intermediate Similarity	NPC16188
0.7584	Intermediate Similarity	NPC476268
0.7578	Intermediate Similarity	NPC35850
0.7578	Intermediate Similarity	NPC276949
0.7571	Intermediate Similarity	NPC476102
0.7571	Intermediate Similarity	NPC293377
0.7571	Intermediate Similarity	NPC79465
0.7571	Intermediate Similarity	NPC76785
0.7571	Intermediate Similarity	NPC9687
0.7571	Intermediate Similarity	NPC273907
0.7571	Intermediate Similarity	NPC118099
0.7571	Intermediate Similarity	NPC474811
0.7571	Intermediate Similarity	NPC151706
0.7571	Intermediate Similarity	NPC475318
0.7571	Intermediate Similarity	NPC49577
0.7571	Intermediate Similarity	NPC475598
0.7571	Intermediate Similarity	NPC90194
0.7571	Intermediate Similarity	NPC474855
0.7571	Intermediate Similarity	NPC474787
0.7571	Intermediate Similarity	NPC260045
0.7569	Intermediate Similarity	NPC471680
0.7554	Intermediate Similarity	NPC287401
0.7551	Intermediate Similarity	NPC473491
0.754	Intermediate Similarity	NPC65855
0.754	Intermediate Similarity	NPC292758
0.7538	Intermediate Similarity	NPC315276
0.7538	Intermediate Similarity	NPC285926
0.7538	Intermediate Similarity	NPC14672
0.7518	Intermediate Similarity	NPC473322
0.7517	Intermediate Similarity	NPC39431
0.75	Intermediate Similarity	NPC40234
0.75	Intermediate Similarity	NPC233702
0.75	Intermediate Similarity	NPC475204
0.75	Intermediate Similarity	NPC475123
0.75	Intermediate Similarity	NPC248283
0.7483	Intermediate Similarity	NPC476989
0.7468	Intermediate Similarity	NPC159767
0.7468	Intermediate Similarity	NPC473402
0.7468	Intermediate Similarity	NPC155506
0.7452	Intermediate Similarity	NPC230611
0.7444	Intermediate Similarity	NPC200964
0.7431	Intermediate Similarity	NPC161069
0.7426	Intermediate Similarity	NPC101719
0.7424	Intermediate Similarity	NPC220698
0.7413	Intermediate Similarity	NPC476259
0.7405	Intermediate Similarity	NPC273755
0.7405	Intermediate Similarity	NPC306804
0.7405	Intermediate Similarity	NPC239357
0.7405	Intermediate Similarity	NPC137627
0.7397	Intermediate Similarity	NPC314358
0.7394	Intermediate Similarity	NPC471264
0.7394	Intermediate Similarity	NPC68865
0.7394	Intermediate Similarity	NPC471265
0.7391	Intermediate Similarity	NPC111428
0.7379	Intermediate Similarity	NPC314388
0.7379	Intermediate Similarity	NPC315283
0.7376	Intermediate Similarity	NPC474473
0.7372	Intermediate Similarity	NPC302597
0.7365	Intermediate Similarity	NPC254798
0.7361	Intermediate Similarity	NPC263493
0.7361	Intermediate Similarity	NPC168113
0.7361	Intermediate Similarity	NPC269398
0.7358	Intermediate Similarity	NPC476227
0.7358	Intermediate Similarity	NPC473354
0.7358	Intermediate Similarity	NPC279871
0.7355	Intermediate Similarity	NPC63931
0.7353	Intermediate Similarity	NPC285394
0.7353	Intermediate Similarity	NPC222466
0.7347	Intermediate Similarity	NPC135121
0.7333	Intermediate Similarity	NPC261934
0.7333	Intermediate Similarity	NPC5194
0.7333	Intermediate Similarity	NPC202198
0.7329	Intermediate Similarity	NPC316008
0.7329	Intermediate Similarity	NPC477217
0.7329	Intermediate Similarity	NPC313867
0.7329	Intermediate Similarity	NPC315266
0.7329	Intermediate Similarity	NPC201244
0.7312	Intermediate Similarity	NPC50016
0.731	Intermediate Similarity	NPC197682
0.731	Intermediate Similarity	NPC251439
0.7302	Intermediate Similarity	NPC45033
0.7299	Intermediate Similarity	NPC4974
0.7286	Intermediate Similarity	NPC255447
0.728	Intermediate Similarity	NPC226778
0.728	Intermediate Similarity	NPC304761
0.728	Intermediate Similarity	NPC147000
0.728	Intermediate Similarity	NPC150254
0.726	Intermediate Similarity	NPC476978
0.7246	Intermediate Similarity	NPC65310
0.7239	Intermediate Similarity	NPC473404
0.7237	Intermediate Similarity	NPC244509
0.723	Intermediate Similarity	NPC145113
0.723	Intermediate Similarity	NPC225648
0.723	Intermediate Similarity	NPC329761
0.723	Intermediate Similarity	NPC138775
0.7226	Intermediate Similarity	NPC22746
0.7222	Intermediate Similarity	NPC194671
0.7222	Intermediate Similarity	NPC269750
0.7222	Intermediate Similarity	NPC211551
0.7222	Intermediate Similarity	NPC45037
0.7219	Intermediate Similarity	NPC56685
0.7211	Intermediate Similarity	NPC209509
0.7208	Intermediate Similarity	NPC244336
0.7206	Intermediate Similarity	NPC474862
0.72	Intermediate Similarity	NPC324081
0.72	Intermediate Similarity	NPC7817
0.72	Intermediate Similarity	NPC475168
0.7192	Intermediate Similarity	NPC176226
0.7192	Intermediate Similarity	NPC139326
0.7185	Intermediate Similarity	NPC190663
0.7181	Intermediate Similarity	NPC9373
0.7179	Intermediate Similarity	NPC471053
0.7179	Intermediate Similarity	NPC471051
0.7179	Intermediate Similarity	NPC471052
0.7172	Intermediate Similarity	NPC268841
0.7172	Intermediate Similarity	NPC46098
0.7172	Intermediate Similarity	NPC307357
0.7143	Intermediate Similarity	NPC52748
0.7143	Intermediate Similarity	NPC26108
0.7134	Intermediate Similarity	NPC476321
0.7134	Intermediate Similarity	NPC472923
0.7133	Intermediate Similarity	NPC2501
0.7125	Intermediate Similarity	NPC89831
0.7123	Intermediate Similarity	NPC469427
0.7123	Intermediate Similarity	NPC469426
0.712	Intermediate Similarity	NPC327226
0.7114	Intermediate Similarity	NPC311658
0.7111	Intermediate Similarity	NPC319950
0.7107	Intermediate Similarity	NPC280022
0.7105	Intermediate Similarity	NPC122590
0.7103	Intermediate Similarity	NPC178662
0.7103	Intermediate Similarity	NPC470884
0.7103	Intermediate Similarity	NPC92784
0.7103	Intermediate Similarity	NPC476133
0.7103	Intermediate Similarity	NPC98424
0.7101	Intermediate Similarity	NPC307020
0.7097	Intermediate Similarity	NPC62104
0.7097	Intermediate Similarity	NPC319320
0.7097	Intermediate Similarity	NPC1390
0.7097	Intermediate Similarity	NPC287757
0.7095	Intermediate Similarity	NPC5620
0.7092	Intermediate Similarity	NPC200589
0.7092	Intermediate Similarity	NPC300315
0.7091	Intermediate Similarity	NPC471526
0.7087	Intermediate Similarity	NPC473418
0.7081	Intermediate Similarity	NPC248670
0.708	Intermediate Similarity	NPC160493
0.7067	Intermediate Similarity	NPC105717
0.7059	Intermediate Similarity	NPC470902
0.7059	Intermediate Similarity	NPC80150
0.7059	Intermediate Similarity	NPC302169
0.7051	Intermediate Similarity	NPC469243
0.7051	Intermediate Similarity	NPC114806
0.7051	Intermediate Similarity	NPC471527
0.705	Intermediate Similarity	NPC474847
0.705	Intermediate Similarity	NPC47667
0.7048	Intermediate Similarity	NPC471049
0.7048	Intermediate Similarity	NPC471050
0.7048	Intermediate Similarity	NPC471048
0.7048	Intermediate Similarity	NPC294951
0.7047	Intermediate Similarity	NPC262077
0.7045	Intermediate Similarity	NPC474544
0.7045	Intermediate Similarity	NPC1986
0.7044	Intermediate Similarity	NPC209463
0.7039	Intermediate Similarity	NPC162104
0.7037	Intermediate Similarity	NPC136797
0.7037	Intermediate Similarity	NPC314992
0.7037	Intermediate Similarity	NPC471165

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 NPC469666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	99
0.1-0.2	331
0.2-0.3	771
0.3-0.4	1659
0.4-0.5	3369
0.5-0.6	2217
0.6-0.7	639
0.7-0.8	65
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
0.8092	Intermediate Similarity	NPD3125	Approved
0.7953	Intermediate Similarity	NPD3123	Discovery
0.7833	Intermediate Similarity	NPD854	Approved
0.7833	Intermediate Similarity	NPD855	Approved
0.7737	Intermediate Similarity	NPD1330	Phase 2
0.7737	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6681	Discovery
0.76	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD8173	Phase 2
0.7518	Intermediate Similarity	NPD8172	Phase 2
0.7517	Intermediate Similarity	NPD6676	Phase 2
0.7466	Intermediate Similarity	NPD8323	Discontinued
0.7447	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3626	Phase 3
0.7383	Intermediate Similarity	NPD7613	Discontinued
0.7372	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5157	Phase 1
0.7353	Intermediate Similarity	NPD5159	Phase 2
0.7353	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4253	Approved
0.7344	Intermediate Similarity	NPD4254	Approved
0.7333	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7131	Phase 3
0.7313	Intermediate Similarity	NPD5723	Approved
0.7302	Intermediate Similarity	NPD811	Approved
0.7302	Intermediate Similarity	NPD810	Approved
0.7302	Intermediate Similarity	NPD812	Approved
0.728	Intermediate Similarity	NPD314	Approved
0.728	Intermediate Similarity	NPD310	Approved
0.728	Intermediate Similarity	NPD315	Approved
0.728	Intermediate Similarity	NPD311	Approved
0.728	Intermediate Similarity	NPD309	Approved
0.728	Intermediate Similarity	NPD10	Approved
0.7279	Intermediate Similarity	NPD2584	Suspended
0.7279	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2160	Approved
0.7246	Intermediate Similarity	NPD2627	Approved
0.7246	Intermediate Similarity	NPD2626	Approved
0.7246	Intermediate Similarity	NPD2628	Approved
0.7246	Intermediate Similarity	NPD2625	Approved
0.7246	Intermediate Similarity	NPD2159	Approved
0.7244	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4677	Discontinued
0.7222	Intermediate Similarity	NPD999	Phase 2
0.7208	Intermediate Similarity	NPD7011	Discontinued
0.7194	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7086	Phase 2
0.7183	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4588	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7130	Phase 3
0.7163	Intermediate Similarity	NPD3136	Phase 2
0.7162	Intermediate Similarity	NPD1968	Approved
0.7162	Intermediate Similarity	NPD1967	Approved
0.7152	Intermediate Similarity	NPD4731	Phase 3
0.7143	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7080	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5309	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4659	Approved
0.7092	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7522	Discontinued
0.7077	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3588	Discontinued
0.7071	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5308	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7303	Discontinued
0.7037	Intermediate Similarity	NPD2218	Phase 2
0.7037	Intermediate Similarity	NPD2217	Approved
0.7029	Intermediate Similarity	NPD3071	Approved
0.7029	Intermediate Similarity	NPD3073	Approved
0.7029	Intermediate Similarity	NPD3072	Approved
0.7021	Intermediate Similarity	NPD4177	Approved
0.7021	Intermediate Similarity	NPD4175	Approved
0.7016	Intermediate Similarity	NPD9612	Approved
0.7016	Intermediate Similarity	NPD9611	Approved
0.7016	Intermediate Similarity	NPD9609	Approved
0.7014	Intermediate Similarity	NPD5296	Approved
0.7	Intermediate Similarity	NPD7484	Phase 3
0.7	Intermediate Similarity	NPD4103	Phase 2
0.7	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7485	Phase 3
0.6993	Remote Similarity	NPD5581	Approved
0.6986	Remote Similarity	NPD6294	Approved
0.6986	Remote Similarity	NPD6295	Approved
0.6972	Remote Similarity	NPD4125	Approved
0.6972	Remote Similarity	NPD4617	Approved
0.6972	Remote Similarity	NPD4620	Approved
0.6972	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5203	Approved
0.6972	Remote Similarity	NPD5201	Approved
0.6959	Remote Similarity	NPD4152	Approved
0.6957	Remote Similarity	NPD4761	Approved
0.6957	Remote Similarity	NPD4762	Approved
0.6954	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4151	Approved
0.695	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8315	Phase 1
0.6929	Remote Similarity	NPD2079	Discontinued
0.6929	Remote Similarity	NPD6792	Phase 3
0.6928	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2047	Approved
0.6923	Remote Similarity	NPD2051	Approved
0.6923	Remote Similarity	NPD2046	Approved
0.6923	Remote Similarity	NPD21	Approved
0.6923	Remote Similarity	NPD2043	Approved
0.6923	Remote Similarity	NPD2048	Approved
0.6923	Remote Similarity	NPD2045	Approved
0.6923	Remote Similarity	NPD2044	Approved
0.6923	Remote Similarity	NPD6039	Approved
0.6923	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2014	Approved
0.6908	Remote Similarity	NPD5613	Approved
0.6908	Remote Similarity	NPD2016	Approved
0.6908	Remote Similarity	NPD5614	Approved
0.6908	Remote Similarity	NPD2013	Approved
0.6897	Remote Similarity	NPD8265	Approved
0.6897	Remote Similarity	NPD8416	Discontinued
0.6892	Remote Similarity	NPD7450	Phase 2
0.6889	Remote Similarity	NPD5292	Approved
0.6889	Remote Similarity	NPD5291	Approved
0.6887	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8303	Discontinued
0.687	Remote Similarity	NPD551	Approved
0.687	Remote Similarity	NPD550	Approved
0.6861	Remote Similarity	NPD1710	Approved
0.6861	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8417	Discontinued
0.6859	Remote Similarity	NPD2891	Approved
0.6853	Remote Similarity	NPD2613	Approved
0.6853	Remote Similarity	NPD5263	Approved
0.6846	Remote Similarity	NPD2088	Approved
0.6846	Remote Similarity	NPD2022	Approved
0.6846	Remote Similarity	NPD2087	Approved
0.6846	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8076	Discontinued
0.6842	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2611	Approved
0.6835	Remote Similarity	NPD4215	Approved
0.6835	Remote Similarity	NPD2608	Approved
0.6835	Remote Similarity	NPD2609	Approved
0.6835	Remote Similarity	NPD2610	Approved
0.6835	Remote Similarity	NPD4217	Approved
0.6835	Remote Similarity	NPD3132	Approved
0.6835	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4218	Approved
0.6835	Remote Similarity	NPD3131	Approved
0.6835	Remote Similarity	NPD4216	Approved
0.6835	Remote Similarity	NPD2612	Approved
0.6828	Remote Similarity	NPD7715	Approved
0.6828	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7714	Approved
0.6824	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1040	Phase 2
0.6821	Remote Similarity	NPD2575	Approved
0.6815	Remote Similarity	NPD7508	Discontinued
0.6812	Remote Similarity	NPD7342	Discontinued
0.6809	Remote Similarity	NPD6325	Discontinued
0.6803	Remote Similarity	NPD6073	Approved
0.6803	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4231	Approved
0.6797	Remote Similarity	NPD4658	Approved
0.6797	Remote Similarity	NPD4656	Approved
0.6797	Remote Similarity	NPD4229	Approved
0.6797	Remote Similarity	NPD3681	Approved
0.6797	Remote Similarity	NPD3683	Approved
0.6788	Remote Similarity	NPD998	Approved
0.6786	Remote Similarity	NPD2562	Approved
0.6786	Remote Similarity	NPD2561	Approved
0.6783	Remote Similarity	NPD3040	Approved
0.6781	Remote Similarity	NPD6346	Approved
0.6781	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4153	Approved
0.6781	Remote Similarity	NPD5120	Approved
0.6781	Remote Similarity	NPD5121	Approved
0.6781	Remote Similarity	NPD5119	Approved
0.6781	Remote Similarity	NPD6623	Phase 3
0.6779	Remote Similarity	NPD7939	Discontinued
0.6776	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4619	Approved
0.6759	Remote Similarity	NPD4621	Approved
0.6759	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7230	Approved
0.6757	Remote Similarity	NPD7231	Approved
0.6739	Remote Similarity	NPD770	Discontinued
0.6738	Remote Similarity	NPD1755	Approved
0.6736	Remote Similarity	NPD4676	Approved
0.6735	Remote Similarity	NPD3577	Discontinued
0.6733	Remote Similarity	NPD7978	Discontinued
0.6733	Remote Similarity	NPD7720	Phase 2
0.6732	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4818	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