NPASS Compound

Structure

NPC470545 OpenBabel07101719512D 39 41 0 0 1 0 0 0 0 0999 V2000 -0.9860 3.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1932 -2.4210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7630 -3.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9210 3.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6375 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9535 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5092 2.4210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5790 -5.2117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5659 -0.5092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2468 -4.7350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4047 -4.7350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5659 0.4443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7402 -0.9860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2468 -3.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4047 -3.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7402 0.9210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9145 -0.5092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5790 -1.3977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2630 1.3977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2397 -2.4210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4443 2.4210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5790 -3.3047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9145 0.4443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2468 -0.9210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4372 0.9210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7630 -1.5952 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9210 1.5952 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9210 -1.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7630 1.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4372 -0.9210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2468 0.9210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8420 -1.8420 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8420 1.8420 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6840 -0.0000 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 0.4443 -2.4210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2397 2.4210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2630 -1.3977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5790 1.3977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 5 34 1 0 0 0 0 6 35 1 0 0 0 0 7 21 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 14 22 2 0 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 21 4 1 6 0 0 0 24 18 1 6 0 0 0 24 28 1 0 0 0 0 24 35 1 0 0 0 0 25 19 1 6 0 0 0 25 29 1 0 0 0 0 25 34 1 0 0 0 0 26 20 1 6 0 0 0 26 30 1 0 0 0 0 26 32 1 0 0 0 0 27 21 1 6 0 0 0 27 31 1 0 0 0 0 27 33 1 0 0 0 0 28 32 2 3 0 0 0 28 36 1 0 0 0 0 29 33 2 3 0 0 0 29 37 1 0 0 0 0 30 34 1 0 0 0 0 30 38 2 0 0 0 0 31 35 1 0 0 0 0 31 39 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.32
Volume:	571.846
LogP:	3.819
LogD:	3.813
LogS:	-4.435
# Rotatable Bonds:	7
TPSA:	98.82
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	4.332
Fsp3:	0.484
Lipinski Rule-of-5:	Accepted
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:	-4.944
MDCK Permeability:	0.00014663820911664516
Pgp-inhibitor:	0.997
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	95.10262298583984%
Volume Distribution (VD):	0.568
Pgp-substrate:	1.8946385383605957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.343
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.76
CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.857

ADMET: Excretion

Clearance (CL):	5.606
Half-life (T1/2):	0.613

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.847
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.015
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC470545

Natural Product ID:	NPC470545
*Common Name:**	(3S,6S,9S,12S)-6,12-Dibenzyl-3-Sec-Butyl-9-Isopropyl-1,7-Dimethyl-1,4,7,10-Tetraazacyclododecane-2,5,8,11-Tetraone
IUPAC Name:	(3S,6S,9S,12S)-6,12-dibenzyl-3-[(2S)-butan-2-yl]-1,7-dimethyl-9-propan-2-yl-1,4,7,10-tetrazacyclododecane-2,5,8,11-tetrone
Synonyms:
Standard InCHIKey:	KZGZTOMXQSOTKE-SJSXQSQASA-N
Standard InCHI:	InChI=1S/C31H42N4O4/c1-7-21(4)27-31(39)35(6)24(18-22-14-10-8-11-15-22)28(36)32-26(20(2)3)30(38)34(5)25(29(37)33-27)19-23-16-12-9-13-17-23/h8-17,20-21,24-27H,7,18-19H2,1-6H3,(H,32,36)(H,33,37)/t21-,24-,25-,26-,27-/m0/s1
SMILES:	CCC(C)C1C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)N1)CC2=CC=CC=C2)C)C(C)C)CC3=CC=CC=C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063168
PubChem CID:	60155057
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
NPO32867	onychocola sclerotica	Species	Arachnomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22694270]

☑ 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	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	7100.0	nM	PMID[515497]
NPT98	Individual Protein	HERG	Homo sapiens	IC50	>	23400.0	nM	PMID[515497]
NPT27	Others	Unspecified		IC50	>	20000.0	nM	PMID[515497]

☑ 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 NPC470545 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	120
0.1-0.2	749
0.2-0.3	6176
0.3-0.4	18173
0.4-0.5	14048
0.5-0.6	2450
0.6-0.7	596
0.7-0.8	300
0.8-0.85	57
0.85-0.9	21
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC470546
0.9908	High Similarity	NPC470544
0.9304	High Similarity	NPC71684
0.9083	High Similarity	NPC473322
0.8983	High Similarity	NPC6975
0.8934	High Similarity	NPC255447
0.8926	High Similarity	NPC111428
0.8889	High Similarity	NPC200964
0.887	High Similarity	NPC239357
0.886	High Similarity	NPC33742
0.8833	High Similarity	NPC101719
0.8814	High Similarity	NPC202521
0.8772	High Similarity	NPC35850
0.8772	High Similarity	NPC276949
0.875	High Similarity	NPC222466
0.8729	High Similarity	NPC476990
0.8699	High Similarity	NPC200589
0.8595	High Similarity	NPC22746
0.8583	High Similarity	NPC252878
0.8537	High Similarity	NPC319766
0.8516	High Similarity	NPC132636
0.8512	High Similarity	NPC46427
0.848	Intermediate Similarity	NPC130309
0.8438	Intermediate Similarity	NPC127741
0.84	Intermediate Similarity	NPC300315
0.839	Intermediate Similarity	NPC14672
0.839	Intermediate Similarity	NPC315276
0.839	Intermediate Similarity	NPC285926
0.8321	Intermediate Similarity	NPC161069
0.8203	Intermediate Similarity	NPC287401
0.8195	Intermediate Similarity	NPC209509
0.8168	Intermediate Similarity	NPC239762
0.8168	Intermediate Similarity	NPC163392
0.8165	Intermediate Similarity	NPC25565
0.8154	Intermediate Similarity	NPC68865
0.8154	Intermediate Similarity	NPC471265
0.8154	Intermediate Similarity	NPC471264
0.814	Intermediate Similarity	NPC248283
0.8099	Intermediate Similarity	NPC220698
0.8091	Intermediate Similarity	NPC473501
0.8091	Intermediate Similarity	NPC475439
0.8074	Intermediate Similarity	NPC16188
0.8074	Intermediate Similarity	NPC138775
0.8051	Intermediate Similarity	NPC474584
0.8031	Intermediate Similarity	NPC469666
0.803	Intermediate Similarity	NPC476259
0.8016	Intermediate Similarity	NPC477937
0.8015	Intermediate Similarity	NPC105717
0.797	Intermediate Similarity	NPC269398
0.797	Intermediate Similarity	NPC263493
0.797	Intermediate Similarity	NPC168113
0.797	Intermediate Similarity	NPC476989
0.7956	Intermediate Similarity	NPC254798
0.792	Intermediate Similarity	NPC474082
0.792	Intermediate Similarity	NPC175726
0.7913	Intermediate Similarity	NPC473418
0.791	Intermediate Similarity	NPC139326
0.791	Intermediate Similarity	NPC197682
0.791	Intermediate Similarity	NPC176226
0.7881	Intermediate Similarity	NPC319579
0.7868	Intermediate Similarity	NPC262077
0.7852	Intermediate Similarity	NPC476978
0.7846	Intermediate Similarity	NPC246079
0.7845	Intermediate Similarity	NPC45033
0.7845	Intermediate Similarity	NPC327481
0.7842	Intermediate Similarity	NPC233702
0.7836	Intermediate Similarity	NPC469426
0.7836	Intermediate Similarity	NPC469427
0.782	Intermediate Similarity	NPC98424
0.782	Intermediate Similarity	NPC178662
0.782	Intermediate Similarity	NPC476133
0.782	Intermediate Similarity	NPC92784
0.782	Intermediate Similarity	NPC470884
0.782	Intermediate Similarity	NPC89489
0.7794	Intermediate Similarity	NPC313867
0.7794	Intermediate Similarity	NPC322878
0.7794	Intermediate Similarity	NPC316008
0.7794	Intermediate Similarity	NPC5620
0.7794	Intermediate Similarity	NPC315266
0.7786	Intermediate Similarity	NPC286551
0.7786	Intermediate Similarity	NPC122590
0.7786	Intermediate Similarity	NPC202198
0.7768	Intermediate Similarity	NPC311242
0.7761	Intermediate Similarity	NPC307357
0.7761	Intermediate Similarity	NPC46098
0.7761	Intermediate Similarity	NPC268841
0.7748	Intermediate Similarity	NPC161972
0.7748	Intermediate Similarity	NPC303045
0.7737	Intermediate Similarity	NPC314358
0.7727	Intermediate Similarity	NPC141050
0.7724	Intermediate Similarity	NPC169328
0.7721	Intermediate Similarity	NPC315283
0.7721	Intermediate Similarity	NPC314388
0.771	Intermediate Similarity	NPC325479
0.768	Intermediate Similarity	NPC477061
0.768	Intermediate Similarity	NPC45777
0.7676	Intermediate Similarity	NPC469903
0.7672	Intermediate Similarity	NPC224610
0.7672	Intermediate Similarity	NPC88267
0.7672	Intermediate Similarity	NPC194390
0.7672	Intermediate Similarity	NPC113326
0.7661	Intermediate Similarity	NPC310467
0.7661	Intermediate Similarity	NPC237420
0.7656	Intermediate Similarity	NPC47667
0.7643	Intermediate Similarity	NPC473491
0.7632	Intermediate Similarity	NPC12730
0.7591	Intermediate Similarity	NPC52748
0.7571	Intermediate Similarity	NPC129666
0.7571	Intermediate Similarity	NPC2501
0.7554	Intermediate Similarity	NPC135121
0.7554	Intermediate Similarity	NPC225648
0.7554	Intermediate Similarity	NPC329761
0.754	Intermediate Similarity	NPC27833
0.7538	Intermediate Similarity	NPC89923
0.7538	Intermediate Similarity	NPC152850
0.7538	Intermediate Similarity	NPC105114
0.7538	Intermediate Similarity	NPC71933
0.7538	Intermediate Similarity	NPC239990
0.7536	Intermediate Similarity	NPC201244
0.7536	Intermediate Similarity	NPC477217
0.7535	Intermediate Similarity	NPC473341
0.7517	Intermediate Similarity	NPC319320
0.7517	Intermediate Similarity	NPC287757
0.75	Intermediate Similarity	NPC35996
0.7483	Intermediate Similarity	NPC473002
0.7482	Intermediate Similarity	NPC81026
0.7481	Intermediate Similarity	NPC43755
0.7477	Intermediate Similarity	NPC226438
0.7466	Intermediate Similarity	NPC473003
0.7466	Intermediate Similarity	NPC469243
0.7466	Intermediate Similarity	NPC469902
0.7466	Intermediate Similarity	NPC471527
0.7462	Intermediate Similarity	NPC136453
0.7444	Intermediate Similarity	NPC257390
0.744	Intermediate Similarity	NPC254088
0.7436	Intermediate Similarity	NPC164859
0.7436	Intermediate Similarity	NPC471317
0.7429	Intermediate Similarity	NPC311658
0.7429	Intermediate Similarity	NPC145113
0.7426	Intermediate Similarity	NPC313694
0.7426	Intermediate Similarity	NPC242159
0.7415	Intermediate Similarity	NPC241794
0.7413	Intermediate Similarity	NPC261934
0.7413	Intermediate Similarity	NPC56685
0.7413	Intermediate Similarity	NPC5194
0.7413	Intermediate Similarity	NPC262166
0.741	Intermediate Similarity	NPC266741
0.7402	Intermediate Similarity	NPC478014
0.7402	Intermediate Similarity	NPC478015
0.7402	Intermediate Similarity	NPC478016
0.7394	Intermediate Similarity	NPC475168
0.7394	Intermediate Similarity	NPC7817
0.7391	Intermediate Similarity	NPC322598
0.7391	Intermediate Similarity	NPC77905
0.7391	Intermediate Similarity	NPC468984
0.7387	Intermediate Similarity	NPC172128
0.7381	Intermediate Similarity	NPC314992
0.7377	Intermediate Similarity	NPC329011
0.7376	Intermediate Similarity	NPC471820
0.7376	Intermediate Similarity	NPC471821
0.7368	Intermediate Similarity	NPC157311
0.7365	Intermediate Similarity	NPC471053
0.7365	Intermediate Similarity	NPC133470
0.7365	Intermediate Similarity	NPC191863
0.7365	Intermediate Similarity	NPC471051
0.7365	Intermediate Similarity	NPC289776
0.7365	Intermediate Similarity	NPC471052
0.7357	Intermediate Similarity	NPC314114
0.7347	Intermediate Similarity	NPC475544
0.7343	Intermediate Similarity	NPC162104
0.7329	Intermediate Similarity	NPC324850
0.7324	Intermediate Similarity	NPC283783
0.7315	Intermediate Similarity	NPC223207
0.7315	Intermediate Similarity	NPC189116
0.7313	Intermediate Similarity	NPC44805
0.7313	Intermediate Similarity	NPC8761
0.7313	Intermediate Similarity	NPC326966
0.731	Intermediate Similarity	NPC476268
0.7288	Intermediate Similarity	NPC202613
0.7286	Intermediate Similarity	NPC471680
0.728	Intermediate Similarity	NPC197470
0.7279	Intermediate Similarity	NPC1390
0.7279	Intermediate Similarity	NPC244336
0.7279	Intermediate Similarity	NPC62104
0.7273	Intermediate Similarity	NPC324081
0.7267	Intermediate Similarity	NPC290755
0.7267	Intermediate Similarity	NPC61004
0.7267	Intermediate Similarity	NPC471771
0.7267	Intermediate Similarity	NPC304074
0.7254	Intermediate Similarity	NPC240848
0.7252	Intermediate Similarity	NPC4974
0.725	Intermediate Similarity	NPC474804
0.725	Intermediate Similarity	NPC474973
0.725	Intermediate Similarity	NPC130898
0.7241	Intermediate Similarity	NPC470902
0.7241	Intermediate Similarity	NPC39431
0.7232	Intermediate Similarity	NPC78041
0.7232	Intermediate Similarity	NPC141139
0.7232	Intermediate Similarity	NPC121872
0.7232	Intermediate Similarity	NPC471307

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 NPC470545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	101
0.1-0.2	337
0.2-0.3	763
0.3-0.4	1877
0.4-0.5	3470
0.5-0.6	1910
0.6-0.7	564
0.7-0.8	122
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD5339	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.8189	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD8172	Phase 2
0.8154	Intermediate Similarity	NPD8173	Phase 2
0.8095	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD8643	Discontinued
0.8077	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD8323	Discontinued
0.8045	Intermediate Similarity	NPD7720	Phase 2
0.8033	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4677	Discontinued
0.8	Intermediate Similarity	NPD7130	Phase 3
0.7969	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD4125	Approved
0.7926	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD2584	Suspended
0.791	Intermediate Similarity	NPD8076	Discontinued
0.7883	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3644	Approved
0.7881	Intermediate Similarity	NPD3643	Approved
0.7881	Intermediate Similarity	NPD3642	Approved
0.7863	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD6901	Phase 3
0.781	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD5367	Discontinued
0.7786	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD999	Phase 2
0.7752	Intermediate Similarity	NPD3626	Phase 3
0.7727	Intermediate Similarity	NPD8265	Approved
0.7727	Intermediate Similarity	NPD8416	Discontinued
0.7721	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD5581	Approved
0.7698	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5263	Approved
0.7681	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3125	Approved
0.7638	Intermediate Similarity	NPD3073	Approved
0.7638	Intermediate Similarity	NPD3071	Approved
0.7638	Intermediate Similarity	NPD3072	Approved
0.763	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6623	Phase 3
0.7574	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD4762	Approved
0.7559	Intermediate Similarity	NPD4761	Approved
0.7557	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2022	Approved
0.75	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2051	Approved
0.75	Intermediate Similarity	NPD2046	Approved
0.75	Intermediate Similarity	NPD21	Approved
0.75	Intermediate Similarity	NPD3123	Discovery
0.75	Intermediate Similarity	NPD2044	Approved
0.75	Intermediate Similarity	NPD2045	Approved
0.75	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2047	Approved
0.75	Intermediate Similarity	NPD2043	Approved
0.75	Intermediate Similarity	NPD2048	Approved
0.7483	Intermediate Similarity	NPD8315	Phase 1
0.7481	Intermediate Similarity	NPD6073	Approved
0.7464	Intermediate Similarity	NPD6681	Discovery
0.7458	Intermediate Similarity	NPD5717	Approved
0.7447	Intermediate Similarity	NPD6088	Approved
0.744	Intermediate Similarity	NPD7522	Discontinued
0.7426	Intermediate Similarity	NPD6295	Approved
0.7426	Intermediate Similarity	NPD6294	Approved
0.7424	Intermediate Similarity	NPD4676	Approved
0.7411	Intermediate Similarity	NPD6690	Approved
0.7405	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD7342	Discontinued
0.7394	Intermediate Similarity	NPD4432	Discontinued
0.7391	Intermediate Similarity	NPD2087	Approved
0.7391	Intermediate Similarity	NPD2088	Approved
0.7385	Intermediate Similarity	NPD5578	Approved
0.7385	Intermediate Similarity	NPD6792	Phase 3
0.7385	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2217	Approved
0.7381	Intermediate Similarity	NPD2218	Phase 2
0.7357	Intermediate Similarity	NPD1968	Approved
0.7357	Intermediate Similarity	NPD1967	Approved
0.7348	Intermediate Similarity	NPD3040	Approved
0.7348	Intermediate Similarity	NPD4177	Approved
0.7348	Intermediate Similarity	NPD7828	Discontinued
0.7348	Intermediate Similarity	NPD5759	Approved
0.7348	Intermediate Similarity	NPD4175	Approved
0.7344	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7303	Discontinued
0.7343	Intermediate Similarity	NPD7613	Discontinued
0.7333	Intermediate Similarity	NPD5323	Approved
0.7324	Intermediate Similarity	NPD5613	Approved
0.7324	Intermediate Similarity	NPD5614	Approved
0.7324	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5981	Approved
0.7317	Intermediate Similarity	NPD480	Approved
0.7313	Intermediate Similarity	NPD1330	Phase 2
0.7313	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1040	Phase 2
0.7299	Intermediate Similarity	NPD6852	Discontinued
0.7292	Intermediate Similarity	NPD7131	Phase 3
0.728	Intermediate Similarity	NPD7508	Discontinued
0.728	Intermediate Similarity	NPD1348	Approved
0.7279	Intermediate Similarity	NPD3908	Approved
0.7279	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4151	Approved
0.7258	Intermediate Similarity	NPD3598	Phase 3
0.7257	Intermediate Similarity	NPD1812	Approved
0.7257	Intermediate Similarity	NPD1814	Approved
0.7252	Intermediate Similarity	NPD2031	Discontinued
0.723	Intermediate Similarity	NPD7599	Phase 2
0.7226	Intermediate Similarity	NPD5725	Approved
0.7214	Intermediate Similarity	NPD2437	Approved
0.7214	Intermediate Similarity	NPD2436	Approved
0.7203	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5716	Approved
0.7203	Intermediate Similarity	NPD3987	Approved
0.7203	Intermediate Similarity	NPD4119	Approved
0.7203	Intermediate Similarity	NPD3988	Approved
0.72	Intermediate Similarity	NPD3551	Approved
0.7197	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7450	Phase 2
0.7185	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5299	Approved
0.7181	Intermediate Similarity	NPD7600	Phase 2
0.7171	Intermediate Similarity	NPD7484	Phase 3
0.7171	Intermediate Similarity	NPD7485	Phase 3
0.7165	Intermediate Similarity	NPD6360	Discontinued
0.7154	Intermediate Similarity	NPD4253	Approved
0.7154	Intermediate Similarity	NPD4254	Approved
0.7143	Intermediate Similarity	NPD3588	Discontinued
0.7133	Intermediate Similarity	NPD8351	Phase 2
0.7132	Intermediate Similarity	NPD941	Approved
0.7123	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3480	Approved
0.7121	Intermediate Similarity	NPD6325	Discontinued
0.7111	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6345	Approved
0.7109	Intermediate Similarity	NPD6343	Approved
0.7109	Intermediate Similarity	NPD998	Approved
0.7103	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8125	Discontinued
0.7099	Intermediate Similarity	NPD5335	Discontinued
0.7099	Intermediate Similarity	NPD6624	Discontinued
0.7095	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7679	Phase 2
0.7083	Intermediate Similarity	NPD2016	Approved
0.7083	Intermediate Similarity	NPD2013	Approved
0.7083	Intermediate Similarity	NPD2014	Approved
0.708	Intermediate Similarity	NPD5296	Approved
0.708	Intermediate Similarity	NPD4153	Approved
0.7067	Intermediate Similarity	NPD7080	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4803	Discontinued
0.7059	Intermediate Similarity	NPD2846	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4214	Discontinued
0.7042	Intermediate Similarity	NPD5024	Approved
0.7031	Intermediate Similarity	NPD3806	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8417	Discontinued
0.7027	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1018	Approved
0.7016	Intermediate Similarity	NPD2583	Phase 2
0.7007	Intermediate Similarity	NPD7086	Phase 2
0.7007	Intermediate Similarity	NPD8118	Discontinued
0.7007	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6806	Phase 1
0.6993	Remote Similarity	NPD6676	Phase 2
0.6986	Remote Similarity	NPD5230	Approved
0.6986	Remote Similarity	NPD5229	Approved
0.6984	Remote Similarity	NPD3150	Approved
0.6984	Remote Similarity	NPD3149	Approved
0.6984	Remote Similarity	NPD2659	Approved
0.6984	Remote Similarity	NPD3147	Approved
0.6984	Remote Similarity	NPD2658	Approved
0.6984	Remote Similarity	NPD3148	Approved
0.6983	Remote Similarity	NPD4814	Discontinued
0.6977	Remote Similarity	NPD4479	Discontinued
0.6953	Remote Similarity	NPD1344	Phase 2
0.695	Remote Similarity	NPD7511	Approved
0.695	Remote Similarity	NPD7512	Approved
0.6949	Remote Similarity	NPD4117	Approved
0.6943	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3581	Discontinued
0.6934	Remote Similarity	NPD7908	Discontinued
0.6929	Remote Similarity	NPD4126	Approved
0.6929	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8303	Discontinued
0.6905	Remote Similarity	NPD1762	Approved
0.6905	Remote Similarity	NPD1764	Approved
0.6901	Remote Similarity	NPD4152	Approved
0.6899	Remote Similarity	NPD5990	Approved
0.6899	Remote Similarity	NPD5991	Approved
0.6894	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4648	Approved
0.6892	Remote Similarity	NPD4646	Approved
0.6892	Remote Similarity	NPD4647	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