NPASS Compound

Structure

NPC311658 OpenBabel07101719152D 39 40 0 0 1 0 0 0 0 0999 V2000 0.9016 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6922 5.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0020 4.9885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5772 -0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4894 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -4.3301 -1.5000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1569 3.7013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0510 4.6794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 -0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 1 0 0 0 0 0 0 0 0 0 0.5862 3.0322 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 1 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 1.1215 1.3849 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 1.5373 3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3783 2.0540 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0725 1.6939 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 1.7452 4.3193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2804 2.6720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 19 2 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 16 34 1 0 0 0 0 18 4 1 6 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 20 24 1 0 0 0 0 21 13 1 6 0 0 0 21 26 1 0 0 0 0 21 32 1 0 0 0 0 22 15 1 1 0 0 0 22 27 1 0 0 0 0 22 33 1 0 0 0 0 23 25 1 6 0 0 0 23 34 1 0 0 0 0 24 32 2 3 0 0 0 24 35 1 0 0 0 0 25 33 2 3 0 0 0 25 36 1 0 0 0 0 26 34 1 0 0 0 0 26 37 2 0 0 0 0 27 38 2 0 0 0 0 27 39 1 0 0 0 0 28 29 2 0 0 0 0 28 30 1 0 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.32
Volume:	561.935
LogP:	1.937
LogD:	1.043
LogS:	-3.389
# Rotatable Bonds:	16
TPSA:	180.21
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	3.983
Fsp3:	0.536
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.032
MDCK Permeability:	0.00020186004985589534
Pgp-inhibitor:	0.006
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.244
Plasma Protein Binding (PPB):	62.03699493408203%
Volume Distribution (VD):	0.255
Pgp-substrate:	39.98429870605469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.314
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	4.33
Half-life (T1/2):	0.511

ADMET: Toxicity

hERG Blockers:	0.132
Human Hepatotoxicity (H-HT):	0.839
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.71
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.061
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC311658

Natural Product ID:	NPC311658
*Common Name:**	Lucentamycin A
IUPAC Name:	(2S)-2-[[(2S,3R,4Z)-1-[(2S)-2-benzamido-6-(diaminomethylideneamino)hexanoyl]-4-ethylidene-3-methylpyrrolidine-2-carbonyl]amino]-4-methylpentanoic acid
Synonyms:
Standard InCHIKey:	BJWAMDSUOTWAAR-UQFBLIRTSA-N
Standard InCHI:	InChI=1S/C28H42N6O5/c1-5-19-16-34(23(18(19)4)25(36)33-22(27(38)39)15-17(2)3)26(37)21(13-9-10-14-31-28(29)30)32-24(35)20-11-7-6-8-12-20/h5-8,11-12,17-18,21-23H,9-10,13-16H2,1-4H3,(H,32,35)(H,33,36)(H,38,39)(H4,29,30,31)/b19-5+/t18-,21+,22+,23+/m1/s1
SMILES:	C/C=C/1CN([C@@H]([C@@H]1C)C(=N[C@@H](CC(C)C)C(=O)O)O)C(=O)[C@H](CCCCNC(=N)N)N=C(c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399974
PubChem CID:	23625391
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:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO26039	0cardiopsis lucentensis	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17630797]
NPO26039	0cardiopsis lucentensis	Species	0cardiopsaceae	Bacteria	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	200.0	nM	PMID[575593]

☑ 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 NPC311658 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	181
0.1-0.2	1294
0.2-0.3	7480
0.3-0.4	18084
0.4-0.5	12359
0.5-0.6	2477
0.6-0.7	543
0.7-0.8	265
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8397	Intermediate Similarity	NPC129486
0.8302	Intermediate Similarity	NPC165285
0.8239	Intermediate Similarity	NPC475532
0.8165	Intermediate Similarity	NPC280022
0.8129	Intermediate Similarity	NPC114806
0.8113	Intermediate Similarity	NPC276506
0.8113	Intermediate Similarity	NPC274198
0.8113	Intermediate Similarity	NPC198254
0.8105	Intermediate Similarity	NPC473580
0.8065	Intermediate Similarity	NPC24617
0.8014	Intermediate Similarity	NPC132636
0.7963	Intermediate Similarity	NPC17698
0.7914	Intermediate Similarity	NPC196243
0.7908	Intermediate Similarity	NPC300443
0.7898	Intermediate Similarity	NPC475544
0.7898	Intermediate Similarity	NPC469243
0.7811	Intermediate Similarity	NPC94862
0.7771	Intermediate Similarity	NPC324850
0.777	Intermediate Similarity	NPC200964
0.7755	Intermediate Similarity	NPC314835
0.775	Intermediate Similarity	NPC223207
0.773	Intermediate Similarity	NPC6975
0.7727	Intermediate Similarity	NPC475168
0.7727	Intermediate Similarity	NPC7817
0.7718	Intermediate Similarity	NPC48202
0.7711	Intermediate Similarity	NPC97526
0.7711	Intermediate Similarity	NPC119652
0.7708	Intermediate Similarity	NPC311753
0.7702	Intermediate Similarity	NPC304074
0.7702	Intermediate Similarity	NPC471771
0.7702	Intermediate Similarity	NPC290755
0.7665	Intermediate Similarity	NPC153554
0.7647	Intermediate Similarity	NPC16188
0.7632	Intermediate Similarity	NPC316008
0.7632	Intermediate Similarity	NPC313867
0.7632	Intermediate Similarity	NPC315266
0.7619	Intermediate Similarity	NPC473404
0.761	Intermediate Similarity	NPC1390
0.761	Intermediate Similarity	NPC62104
0.7589	Intermediate Similarity	NPC202521
0.7589	Intermediate Similarity	NPC71684
0.7582	Intermediate Similarity	NPC314114
0.7582	Intermediate Similarity	NPC314358
0.758	Intermediate Similarity	NPC470902
0.7569	Intermediate Similarity	NPC477937
0.7566	Intermediate Similarity	NPC315283
0.7566	Intermediate Similarity	NPC314388
0.7532	Intermediate Similarity	NPC469903
0.7531	Intermediate Similarity	NPC63931
0.7518	Intermediate Similarity	NPC476990
0.7516	Intermediate Similarity	NPC56685
0.75	Intermediate Similarity	NPC66490
0.7485	Intermediate Similarity	NPC61004
0.7483	Intermediate Similarity	NPC255447
0.7467	Intermediate Similarity	NPC471264
0.7467	Intermediate Similarity	NPC471265
0.7443	Intermediate Similarity	NPC477632
0.7443	Intermediate Similarity	NPC477638
0.7434	Intermediate Similarity	NPC476989
0.7429	Intermediate Similarity	NPC470545
0.7423	Intermediate Similarity	NPC217804
0.7423	Intermediate Similarity	NPC210377
0.7423	Intermediate Similarity	NPC22883
0.7423	Intermediate Similarity	NPC5719
0.7414	Intermediate Similarity	NPC477636
0.7414	Intermediate Similarity	NPC61332
0.7414	Intermediate Similarity	NPC240130
0.7413	Intermediate Similarity	NPC252878
0.7405	Intermediate Similarity	NPC202198
0.7399	Intermediate Similarity	NPC96275
0.7386	Intermediate Similarity	NPC77905
0.7379	Intermediate Similarity	NPC101719
0.7378	Intermediate Similarity	NPC15068
0.7376	Intermediate Similarity	NPC470546
0.7365	Intermediate Similarity	NPC130309
0.7361	Intermediate Similarity	NPC46427
0.7357	Intermediate Similarity	NPC470544
0.7357	Intermediate Similarity	NPC239357
0.7356	Intermediate Similarity	NPC102959
0.7353	Intermediate Similarity	NPC170302
0.7353	Intermediate Similarity	NPC475409
0.7353	Intermediate Similarity	NPC475564
0.7347	Intermediate Similarity	NPC473322
0.7347	Intermediate Similarity	NPC111428
0.7346	Intermediate Similarity	NPC469902
0.7338	Intermediate Similarity	NPC476978
0.7338	Intermediate Similarity	NPC52748
0.7333	Intermediate Similarity	NPC63040
0.7333	Intermediate Similarity	NPC141050
0.7333	Intermediate Similarity	NPC328649
0.733	Intermediate Similarity	NPC477631
0.7329	Intermediate Similarity	NPC326349
0.7329	Intermediate Similarity	NPC323336
0.7325	Intermediate Similarity	NPC2501
0.7319	Intermediate Similarity	NPC474584
0.7317	Intermediate Similarity	NPC189116
0.7314	Intermediate Similarity	NPC51047
0.7314	Intermediate Similarity	NPC60516
0.7312	Intermediate Similarity	NPC476268
0.731	Intermediate Similarity	NPC222466
0.7303	Intermediate Similarity	NPC477639
0.7303	Intermediate Similarity	NPC313694
0.7303	Intermediate Similarity	NPC242159
0.7303	Intermediate Similarity	NPC470884
0.7303	Intermediate Similarity	NPC476133
0.7303	Intermediate Similarity	NPC98424
0.7303	Intermediate Similarity	NPC178662
0.7303	Intermediate Similarity	NPC92784
0.7301	Intermediate Similarity	NPC241794
0.7297	Intermediate Similarity	NPC300315
0.7297	Intermediate Similarity	NPC200589
0.7296	Intermediate Similarity	NPC262166
0.7296	Intermediate Similarity	NPC5194
0.7296	Intermediate Similarity	NPC473341
0.7296	Intermediate Similarity	NPC261934
0.729	Intermediate Similarity	NPC209509
0.729	Intermediate Similarity	NPC5620
0.7288	Intermediate Similarity	NPC302715
0.7273	Intermediate Similarity	NPC468984
0.7257	Intermediate Similarity	NPC246591
0.7246	Intermediate Similarity	NPC475123
0.7246	Intermediate Similarity	NPC475204
0.7235	Intermediate Similarity	NPC473546
0.7234	Intermediate Similarity	NPC315276
0.7234	Intermediate Similarity	NPC14672
0.7234	Intermediate Similarity	NPC285926
0.7233	Intermediate Similarity	NPC233702
0.7233	Intermediate Similarity	NPC162104
0.7219	Intermediate Similarity	NPC248283
0.7215	Intermediate Similarity	NPC254798
0.7208	Intermediate Similarity	NPC269398
0.7208	Intermediate Similarity	NPC263493
0.7205	Intermediate Similarity	NPC244509
0.7202	Intermediate Similarity	NPC89831
0.7197	Intermediate Similarity	NPC329761
0.7197	Intermediate Similarity	NPC225648
0.7192	Intermediate Similarity	NPC22746
0.7188	Intermediate Similarity	NPC122590
0.7179	Intermediate Similarity	NPC322878
0.7175	Intermediate Similarity	NPC470728
0.717	Intermediate Similarity	NPC473491
0.7161	Intermediate Similarity	NPC161069
0.7152	Intermediate Similarity	NPC287401
0.7152	Intermediate Similarity	NPC471821
0.7152	Intermediate Similarity	NPC471820
0.7143	Intermediate Similarity	NPC46009
0.7134	Intermediate Similarity	NPC81026
0.7134	Intermediate Similarity	NPC469901
0.7127	Intermediate Similarity	NPC477552
0.7127	Intermediate Similarity	NPC477550
0.7126	Intermediate Similarity	NPC209463
0.7124	Intermediate Similarity	NPC127741
0.7118	Intermediate Similarity	NPC471165
0.7114	Intermediate Similarity	NPC469666
0.7107	Intermediate Similarity	NPC129666
0.7105	Intermediate Similarity	NPC267237
0.7092	Intermediate Similarity	NPC33742
0.7091	Intermediate Similarity	NPC73655
0.7089	Intermediate Similarity	NPC145113
0.7086	Intermediate Similarity	NPC246079
0.7086	Intermediate Similarity	NPC326966
0.7083	Intermediate Similarity	NPC469904
0.7073	Intermediate Similarity	NPC244336
0.707	Intermediate Similarity	NPC266741
0.7059	Intermediate Similarity	NPC137627
0.7056	Intermediate Similarity	NPC80514
0.7049	Intermediate Similarity	NPC477551
0.7037	Intermediate Similarity	NPC473002
0.7032	Intermediate Similarity	NPC163392
0.7032	Intermediate Similarity	NPC239762
0.703	Intermediate Similarity	NPC473003
0.7025	Intermediate Similarity	NPC262077
0.7021	Intermediate Similarity	NPC35850
0.7021	Intermediate Similarity	NPC276949
0.7018	Intermediate Similarity	NPC26108
0.7012	Intermediate Similarity	NPC197743
0.7012	Intermediate Similarity	NPC297145
0.7007	Intermediate Similarity	NPC327481
0.6982	Remote Similarity	NPC473000
0.6981	Remote Similarity	NPC138775
0.697	Remote Similarity	NPC469898
0.6962	Remote Similarity	NPC471680
0.6959	Remote Similarity	NPC306804
0.6957	Remote Similarity	NPC469443
0.6954	Remote Similarity	NPC472999
0.6937	Remote Similarity	NPC240848
0.6933	Remote Similarity	NPC39431
0.6923	Remote Similarity	NPC329295
0.6923	Remote Similarity	NPC141957
0.6923	Remote Similarity	NPC214988
0.6919	Remote Similarity	NPC477462
0.6914	Remote Similarity	NPC477637
0.6913	Remote Similarity	NPC4974
0.6905	Remote Similarity	NPC472923
0.6903	Remote Similarity	NPC68865
0.6901	Remote Similarity	NPC328494
0.6897	Remote Similarity	NPC269750
0.6897	Remote Similarity	NPC194671
0.6894	Remote Similarity	NPC13470
0.6893	Remote Similarity	NPC299806

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 NPC311658 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	115
0.1-0.2	340
0.2-0.3	679
0.3-0.4	1557
0.4-0.5	4109
0.5-0.6	1990
0.6-0.7	290
0.7-0.8	60
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD6670	Clinical (unspecified phase)
0.8897	High Similarity	NPD6078	Clinical (unspecified phase)
0.8506	High Similarity	NPD8303	Discontinued
0.844	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD1330	Phase 2
0.8429	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD6901	Phase 3
0.8345	Intermediate Similarity	NPD8076	Discontinued
0.8194	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3125	Approved
0.7917	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3073	Approved
0.7857	Intermediate Similarity	NPD3071	Approved
0.7857	Intermediate Similarity	NPD3072	Approved
0.7847	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4762	Approved
0.7786	Intermediate Similarity	NPD4761	Approved
0.7744	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7523	Phase 3
0.7708	Intermediate Similarity	NPD3040	Approved
0.7655	Intermediate Similarity	NPD5263	Approved
0.7655	Intermediate Similarity	NPD4676	Approved
0.761	Intermediate Similarity	NPD7495	Discontinued
0.76	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4175	Approved
0.7586	Intermediate Similarity	NPD4177	Approved
0.7569	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5323	Approved
0.7548	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6073	Approved
0.7467	Intermediate Similarity	NPD5725	Approved
0.7451	Intermediate Similarity	NPD6681	Discovery
0.745	Intermediate Similarity	NPD4153	Approved
0.7434	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5299	Approved
0.7417	Intermediate Similarity	NPD4214	Discontinued
0.7415	Intermediate Similarity	NPD4125	Approved
0.7413	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8019	Approved
0.7361	Intermediate Similarity	NPD2584	Suspended
0.7329	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6088	Approved
0.7314	Intermediate Similarity	NPD7617	Discontinued
0.731	Intermediate Similarity	NPD4677	Discontinued
0.7285	Intermediate Similarity	NPD3908	Approved
0.7278	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2088	Approved
0.7273	Intermediate Similarity	NPD2087	Approved
0.7267	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4158	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1968	Approved
0.7244	Intermediate Similarity	NPD1967	Approved
0.7237	Intermediate Similarity	NPD8173	Phase 2
0.7237	Intermediate Similarity	NPD8172	Phase 2
0.7234	Intermediate Similarity	NPD3123	Discovery
0.7233	Intermediate Similarity	NPD7613	Discontinued
0.7215	Intermediate Similarity	NPD5613	Approved
0.7215	Intermediate Similarity	NPD3988	Approved
0.7215	Intermediate Similarity	NPD3987	Approved
0.7215	Intermediate Similarity	NPD5614	Approved
0.719	Intermediate Similarity	NPD4126	Approved
0.7178	Intermediate Similarity	NPD3589	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5747	Discontinued
0.7152	Intermediate Similarity	NPD5308	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5367	Discontinued
0.7143	Intermediate Similarity	NPD4652	Approved
0.7133	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2098	Approved
0.7105	Intermediate Similarity	NPD8416	Discontinued
0.7091	Intermediate Similarity	NPD2097	Approved
0.7089	Intermediate Similarity	NPD5309	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8643	Discontinued
0.7051	Intermediate Similarity	NPD2022	Approved
0.7047	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4151	Approved
0.703	Intermediate Similarity	NPD4566	Approved
0.703	Intermediate Similarity	NPD4567	Approved
0.7025	Intermediate Similarity	NPD6676	Phase 2
0.702	Intermediate Similarity	NPD2051	Approved
0.702	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2048	Approved
0.702	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2046	Approved
0.702	Intermediate Similarity	NPD21	Approved
0.702	Intermediate Similarity	NPD2047	Approved
0.702	Intermediate Similarity	NPD2043	Approved
0.702	Intermediate Similarity	NPD2045	Approved
0.702	Intermediate Similarity	NPD2044	Approved
0.7	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5581	Approved
0.6962	Remote Similarity	NPD5264	Approved
0.6962	Remote Similarity	NPD5265	Approved
0.6957	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5230	Approved
0.6914	Remote Similarity	NPD4731	Phase 3
0.6914	Remote Similarity	NPD5229	Approved
0.6908	Remote Similarity	NPD4794	Discontinued
0.6908	Remote Similarity	NPD3136	Phase 2
0.6899	Remote Similarity	NPD2436	Approved
0.6899	Remote Similarity	NPD2437	Approved
0.6894	Remote Similarity	NPD2013	Approved
0.6894	Remote Similarity	NPD2016	Approved
0.6894	Remote Similarity	NPD2014	Approved
0.6892	Remote Similarity	NPD6624	Discontinued
0.6883	Remote Similarity	NPD5296	Approved
0.6883	Remote Similarity	NPD6623	Phase 3
0.6867	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD747	Discontinued
0.6851	Remote Similarity	NPD6665	Discontinued
0.6848	Remote Similarity	NPD5856	Discontinued
0.6835	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3519	Discontinued
0.6829	Remote Similarity	NPD4648	Approved
0.6829	Remote Similarity	NPD4647	Approved
0.6829	Remote Similarity	NPD4646	Approved
0.681	Remote Similarity	NPD7303	Discontinued
0.6803	Remote Similarity	NPD7342	Discontinued
0.6798	Remote Similarity	NPD6557	Phase 2
0.6796	Remote Similarity	NPD6058	Phase 2
0.6788	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7485	Phase 3
0.6784	Remote Similarity	NPD7484	Phase 3
0.6776	Remote Similarity	NPD5759	Approved
0.6772	Remote Similarity	NPD7450	Phase 2
0.677	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6294	Approved
0.6752	Remote Similarity	NPD6852	Discontinued
0.6752	Remote Similarity	NPD6295	Approved
0.6732	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7720	Phase 2
0.6728	Remote Similarity	NPD3509	Approved
0.6728	Remote Similarity	NPD3510	Approved
0.6723	Remote Similarity	NPD4087	Phase 2
0.6723	Remote Similarity	NPD3990	Phase 3
0.6722	Remote Similarity	NPD3919	Approved
0.6711	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3588	Discontinued
0.671	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3480	Approved
0.6703	Remote Similarity	NPD5042	Phase 1
0.6691	Remote Similarity	NPD1040	Phase 2
0.669	Remote Similarity	NPD1348	Approved
0.6689	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6646	Discontinued
0.6667	Remote Similarity	NPD2217	Approved
0.6667	Remote Similarity	NPD7011	Discontinued
0.6667	Remote Similarity	NPD2218	Phase 2
0.6667	Remote Similarity	NPD7131	Phase 3
0.6667	Remote Similarity	NPD3518	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3989	Phase 3
0.6648	Remote Similarity	NPD4092	Approved
0.6647	Remote Similarity	NPD2891	Approved
0.6645	Remote Similarity	NPD4619	Approved
0.6645	Remote Similarity	NPD4621	Approved
0.6629	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8315	Phase 1
0.6627	Remote Similarity	NPD4557	Approved
0.6625	Remote Similarity	NPD3625	Discontinued
0.6612	Remote Similarity	NPD5077	Approved
0.6612	Remote Similarity	NPD5076	Approved
0.6611	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD480	Approved
0.6591	Remote Similarity	NPD4091	Approved
0.659	Remote Similarity	NPD2017	Approved
0.659	Remote Similarity	NPD2889	Approved
0.659	Remote Similarity	NPD2888	Approved
0.659	Remote Similarity	NPD2890	Approved
0.6585	Remote Similarity	NPD1582	Approved
0.6585	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1581	Approved
0.6584	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6325	Discontinued
0.6579	Remote Similarity	NPD3098	Discontinued
0.6566	Remote Similarity	NPD4090	Discontinued
0.6564	Remote Similarity	NPD8323	Discontinued
0.6564	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5272	Discontinued
0.6556	Remote Similarity	NPD5108	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