NPASS Compound

Structure

NPC473418 OpenBabel07101718222D 24 26 0 0 1 0 0 0 0 0999 V2000 0.0000 3.0000 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 4.3301 0.5000 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 3.4641 -0.0000 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 0.5000 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 -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 2.0000 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 2.5981 1.5000 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 17 13 1 1 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 14 1 1 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.17
Volume:	347.289
LogP:	2.776
LogD:	3.056
LogS:	-3.189
# Rotatable Bonds:	4
TPSA:	40.62
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.865
Synthetic Accessibility Score:	2.778
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.728
MDCK Permeability:	0.00011239146260777488
Pgp-inhibitor:	0.131
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.605
Plasma Protein Binding (PPB):	84.86670684814453%
Volume Distribution (VD):	0.489
Pgp-substrate:	15.229116439819336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.306
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.141
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.538
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	12.01
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.754
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.072
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC473418

Natural Product ID:	NPC473418
*Common Name:**	(3S,6S)-3,6-Dibenzyl-1,4-Dimethylpiperazine-2,5-Dione
IUPAC Name:	(3S,6S)-3,6-dibenzyl-1,4-dimethylpiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	KNKXKVUFAHAVOL-ROUUACIJSA-N
Standard InCHI:	InChI=1S/C20H22N2O2/c1-21-17(13-15-9-5-3-6-10-15)20(24)22(2)18(19(21)23)14-16-11-7-4-8-12-16/h3-12,17-18H,13-14H2,1-2H3/t17-,18-/m0/s1
SMILES:	CN1C(=O)[C@H](Cc2ccccc2)N(C(=O)[C@@H]1Cc1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL422955
PubChem CID:	6454124
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11551769]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1593278]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18232659]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21693706]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21939253]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22101040]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25730866]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5447649]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[809439]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[TCMID]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3579	Individual Protein	Calpain 1	Homo sapiens	Inhibition	=	0.0	%	PMID[458427]

☑ 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 NPC473418 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	157
0.1-0.2	1570
0.2-0.3	9823
0.3-0.4	18777
0.4-0.5	10120
0.5-0.6	1726
0.6-0.7	461
0.7-0.8	59
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8319	Intermediate Similarity	NPC220698
0.8131	Intermediate Similarity	NPC167336
0.8056	Intermediate Similarity	NPC45033
0.8017	Intermediate Similarity	NPC27833
0.7913	Intermediate Similarity	NPC470545
0.7886	Intermediate Similarity	NPC257390
0.7863	Intermediate Similarity	NPC302169
0.7845	Intermediate Similarity	NPC470546
0.7826	Intermediate Similarity	NPC470544
0.7797	Intermediate Similarity	NPC71684
0.7788	Intermediate Similarity	NPC256452
0.7787	Intermediate Similarity	NPC473322
0.7736	Intermediate Similarity	NPC322598
0.7692	Intermediate Similarity	NPC71140
0.7672	Intermediate Similarity	NPC315276
0.7672	Intermediate Similarity	NPC285926
0.7672	Intermediate Similarity	NPC14672
0.7652	Intermediate Similarity	NPC33742
0.7642	Intermediate Similarity	NPC111428
0.7624	Intermediate Similarity	NPC17497
0.7624	Intermediate Similarity	NPC305602
0.7623	Intermediate Similarity	NPC136453
0.7586	Intermediate Similarity	NPC473573
0.7568	Intermediate Similarity	NPC473498
0.7565	Intermediate Similarity	NPC276949
0.7565	Intermediate Similarity	NPC35850
0.7563	Intermediate Similarity	NPC200964
0.7561	Intermediate Similarity	NPC152850
0.7561	Intermediate Similarity	NPC71933
0.7561	Intermediate Similarity	NPC239990
0.7561	Intermediate Similarity	NPC89923
0.7561	Intermediate Similarity	NPC105114
0.752	Intermediate Similarity	NPC255447
0.7459	Intermediate Similarity	NPC222466
0.744	Intermediate Similarity	NPC200589
0.7398	Intermediate Similarity	NPC101719
0.7381	Intermediate Similarity	NPC157311
0.7373	Intermediate Similarity	NPC239357
0.7344	Intermediate Similarity	NPC474473
0.7333	Intermediate Similarity	NPC470926
0.7323	Intermediate Similarity	NPC8761
0.7323	Intermediate Similarity	NPC44805
0.7264	Intermediate Similarity	NPC473661
0.7236	Intermediate Similarity	NPC175726
0.7236	Intermediate Similarity	NPC474082
0.7176	Intermediate Similarity	NPC132636
0.7168	Intermediate Similarity	NPC476198
0.7156	Intermediate Similarity	NPC472258
0.712	Intermediate Similarity	NPC79698
0.7097	Intermediate Similarity	NPC6975
0.7087	Intermediate Similarity	NPC469666
0.7059	Intermediate Similarity	NPC474088
0.704	Intermediate Similarity	NPC22746
0.7018	Intermediate Similarity	NPC67043
0.7015	Intermediate Similarity	NPC161069
0.7009	Intermediate Similarity	NPC319579
0.6935	Remote Similarity	NPC202521
0.693	Remote Similarity	NPC275467
0.6923	Remote Similarity	NPC158854
0.6917	Remote Similarity	NPC246904
0.6912	Remote Similarity	NPC209509
0.6905	Remote Similarity	NPC285394
0.6897	Remote Similarity	NPC55529
0.6881	Remote Similarity	NPC474974
0.6881	Remote Similarity	NPC291070
0.6881	Remote Similarity	NPC246757
0.6875	Remote Similarity	NPC12730
0.6875	Remote Similarity	NPC319766
0.6866	Remote Similarity	NPC239762
0.6866	Remote Similarity	NPC163392
0.6863	Remote Similarity	NPC231986
0.6861	Remote Similarity	NPC262077
0.6855	Remote Similarity	NPC476990
0.6846	Remote Similarity	NPC126458
0.6846	Remote Similarity	NPC130309
0.6842	Remote Similarity	NPC127741
0.6832	Remote Similarity	NPC272260
0.6818	Remote Similarity	NPC248283
0.6818	Remote Similarity	NPC329430
0.6812	Remote Similarity	NPC138775
0.6809	Remote Similarity	NPC66936
0.68	Remote Similarity	NPC314192
0.68	Remote Similarity	NPC9796
0.6794	Remote Similarity	NPC473962
0.6791	Remote Similarity	NPC98424
0.6791	Remote Similarity	NPC92784
0.6791	Remote Similarity	NPC178662
0.6791	Remote Similarity	NPC476133
0.6791	Remote Similarity	NPC470884
0.678	Remote Similarity	NPC292758
0.678	Remote Similarity	NPC65855
0.6763	Remote Similarity	NPC9373
0.6754	Remote Similarity	NPC329375
0.6754	Remote Similarity	NPC291610
0.6754	Remote Similarity	NPC239854
0.6746	Remote Similarity	NPC252878
0.6738	Remote Similarity	NPC233702
0.6731	Remote Similarity	NPC104070
0.6696	Remote Similarity	NPC293628
0.6696	Remote Similarity	NPC122493
0.6696	Remote Similarity	NPC10781
0.6696	Remote Similarity	NPC164859
0.6696	Remote Similarity	NPC311242
0.6693	Remote Similarity	NPC46427
0.6691	Remote Similarity	NPC269398
0.6691	Remote Similarity	NPC16188
0.6691	Remote Similarity	NPC263493
0.6667	Remote Similarity	NPC151405
0.6667	Remote Similarity	NPC316906
0.6667	Remote Similarity	NPC477937
0.6667	Remote Similarity	NPC471680
0.6667	Remote Similarity	NPC139901
0.6667	Remote Similarity	NPC471447
0.6644	Remote Similarity	NPC276085
0.6643	Remote Similarity	NPC105717
0.6643	Remote Similarity	NPC189908
0.6642	Remote Similarity	NPC118099
0.6642	Remote Similarity	NPC475598
0.6642	Remote Similarity	NPC273907
0.6642	Remote Similarity	NPC293377
0.6642	Remote Similarity	NPC474855
0.6642	Remote Similarity	NPC79465
0.6642	Remote Similarity	NPC90194
0.6642	Remote Similarity	NPC76785
0.6642	Remote Similarity	NPC260045
0.6642	Remote Similarity	NPC470301
0.6642	Remote Similarity	NPC151706
0.6642	Remote Similarity	NPC9687
0.6642	Remote Similarity	NPC475318
0.6642	Remote Similarity	NPC49577
0.6642	Remote Similarity	NPC139326
0.6642	Remote Similarity	NPC474787
0.6642	Remote Similarity	NPC474811
0.6642	Remote Similarity	NPC476102
0.6641	Remote Similarity	NPC179224
0.6641	Remote Similarity	NPC300315
0.6639	Remote Similarity	NPC113099
0.6618	Remote Similarity	NPC46098
0.6618	Remote Similarity	NPC469560
0.6618	Remote Similarity	NPC307357
0.6618	Remote Similarity	NPC268841
0.6614	Remote Similarity	NPC291027
0.6614	Remote Similarity	NPC84281
0.6614	Remote Similarity	NPC213126
0.6614	Remote Similarity	NPC317474
0.6614	Remote Similarity	NPC169485
0.6612	Remote Similarity	NPC474584
0.6594	Remote Similarity	NPC52748
0.6593	Remote Similarity	NPC68865
0.6591	Remote Similarity	NPC120251
0.6581	Remote Similarity	NPC143516
0.6575	Remote Similarity	NPC222029
0.6573	Remote Similarity	NPC122590
0.6571	Remote Similarity	NPC119677
0.6554	Remote Similarity	NPC471051
0.6554	Remote Similarity	NPC471053
0.6554	Remote Similarity	NPC471052
0.6552	Remote Similarity	NPC471317
0.6549	Remote Similarity	NPC324569
0.6547	Remote Similarity	NPC5620
0.6547	Remote Similarity	NPC201244
0.6547	Remote Similarity	NPC477217
0.6544	Remote Similarity	NPC242159
0.6544	Remote Similarity	NPC89489
0.6544	Remote Similarity	NPC313694
0.6542	Remote Similarity	NPC203076
0.6541	Remote Similarity	NPC325479
0.6538	Remote Similarity	NPC119326
0.6535	Remote Similarity	NPC271642
0.6528	Remote Similarity	NPC473002
0.6525	Remote Similarity	NPC474973
0.6525	Remote Similarity	NPC130898
0.6525	Remote Similarity	NPC327481
0.6525	Remote Similarity	NPC474804
0.6522	Remote Similarity	NPC197682
0.6509	Remote Similarity	NPC169016
0.6508	Remote Similarity	NPC226143
0.6496	Remote Similarity	NPC476259
0.6493	Remote Similarity	NPC287401
0.6483	Remote Similarity	NPC469903
0.6481	Remote Similarity	NPC69057
0.648	Remote Similarity	NPC476440
0.6479	Remote Similarity	NPC254798
0.6475	Remote Similarity	NPC476978
0.6471	Remote Similarity	NPC471264
0.6471	Remote Similarity	NPC471265
0.6471	Remote Similarity	NPC471123
0.6465	Remote Similarity	NPC74458
0.6462	Remote Similarity	NPC4974
0.6462	Remote Similarity	NPC474847
0.6458	Remote Similarity	NPC473341
0.6458	Remote Similarity	NPC286551
0.6458	Remote Similarity	NPC202198
0.6454	Remote Similarity	NPC135121
0.6449	Remote Similarity	NPC168113
0.6449	Remote Similarity	NPC123476
0.6444	Remote Similarity	NPC266425
0.6442	Remote Similarity	NPC477703
0.6436	Remote Similarity	NPC98976
0.6434	Remote Similarity	NPC35996

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 NPC473418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	119
0.1-0.2	542
0.2-0.3	925
0.3-0.4	2473
0.4-0.5	3141
0.5-0.6	1354
0.6-0.7	493
0.7-0.8	94
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8796	High Similarity	NPD3551	Approved
0.8496	Intermediate Similarity	NPD6806	Phase 1
0.8365	Intermediate Similarity	NPD4803	Discontinued
0.8333	Intermediate Similarity	NPD3581	Discontinued
0.8304	Intermediate Similarity	NPD7679	Phase 2
0.8247	Intermediate Similarity	NPD5252	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7130	Phase 3
0.819	Intermediate Similarity	NPD6024	Approved
0.819	Intermediate Similarity	NPD6027	Approved
0.8158	Intermediate Similarity	NPD6343	Approved
0.8158	Intermediate Similarity	NPD6345	Approved
0.8051	Intermediate Similarity	NPD4677	Discontinued
0.8019	Intermediate Similarity	NPD6588	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD2508	Discontinued
0.7913	Intermediate Similarity	NPD5991	Approved
0.7913	Intermediate Similarity	NPD5990	Approved
0.7913	Intermediate Similarity	NPD3806	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD5581	Approved
0.7843	Intermediate Similarity	NPD2998	Approved
0.7843	Intermediate Similarity	NPD2997	Approved
0.7843	Intermediate Similarity	NPD3000	Approved
0.7815	Intermediate Similarity	NPD6408	Phase 1
0.781	Intermediate Similarity	NPD1099	Approved
0.781	Intermediate Similarity	NPD1100	Approved
0.781	Intermediate Similarity	NPD4655	Approved
0.781	Intermediate Similarity	NPD4657	Approved
0.7807	Intermediate Similarity	NPD3867	Phase 2
0.7788	Intermediate Similarity	NPD480	Approved
0.7731	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5180	Approved
0.7719	Intermediate Similarity	NPD5181	Approved
0.7719	Intermediate Similarity	NPD5179	Approved
0.7686	Intermediate Similarity	NPD6792	Phase 3
0.7647	Intermediate Similarity	NPD5187	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4094	Approved
0.7603	Intermediate Similarity	NPD3549	Approved
0.7603	Intermediate Similarity	NPD3550	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3547	Approved
0.7593	Intermediate Similarity	NPD5630	Phase 1
0.7586	Intermediate Similarity	NPD1323	Discontinued
0.7583	Intermediate Similarity	NPD3624	Phase 2
0.7578	Intermediate Similarity	NPD6294	Approved
0.7578	Intermediate Similarity	NPD6295	Approved
0.757	Intermediate Similarity	NPD466	Approved
0.7563	Intermediate Similarity	NPD3064	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4026	Approved
0.7551	Intermediate Similarity	NPD4027	Approved
0.7544	Intermediate Similarity	NPD2124	Approved
0.7524	Intermediate Similarity	NPD6549	Approved
0.7524	Intermediate Similarity	NPD6548	Approved
0.75	Intermediate Similarity	NPD742	Approved
0.7477	Intermediate Similarity	NPD1761	Approved
0.7477	Intermediate Similarity	NPD1763	Approved
0.7477	Intermediate Similarity	NPD1767	Approved
0.7477	Intermediate Similarity	NPD2197	Approved
0.7477	Intermediate Similarity	NPD1766	Approved
0.7477	Intermediate Similarity	NPD2192	Approved
0.7477	Intermediate Similarity	NPD1765	Approved
0.7436	Intermediate Similarity	NPD1025	Discontinued
0.7419	Intermediate Similarity	NPD3578	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD3072	Approved
0.7377	Intermediate Similarity	NPD3071	Approved
0.7377	Intermediate Similarity	NPD3073	Approved
0.7364	Intermediate Similarity	NPD2648	Phase 3
0.7364	Intermediate Similarity	NPD2193	Phase 2
0.7364	Intermediate Similarity	NPD813	Approved
0.7364	Intermediate Similarity	NPD2171	Approved
0.7355	Intermediate Similarity	NPD1302	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4636	Approved
0.7344	Intermediate Similarity	NPD6623	Phase 3
0.7327	Intermediate Similarity	NPD2539	Approved
0.7327	Intermediate Similarity	NPD2538	Approved
0.732	Intermediate Similarity	NPD4144	Approved
0.732	Intermediate Similarity	NPD4147	Approved
0.7317	Intermediate Similarity	NPD7464	Phase 3
0.7308	Intermediate Similarity	NPD4705	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5131	Approved
0.7302	Intermediate Similarity	NPD5263	Approved
0.73	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4169	Approved
0.73	Intermediate Similarity	NPD4170	Approved
0.7297	Intermediate Similarity	NPD3357	Discontinued
0.7295	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD4762	Approved
0.7295	Intermediate Similarity	NPD4761	Approved
0.728	Intermediate Similarity	NPD4151	Approved
0.7266	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7578	Phase 2
0.725	Intermediate Similarity	NPD5859	Discontinued
0.7248	Intermediate Similarity	NPD6498	Approved
0.7248	Intermediate Similarity	NPD6499	Approved
0.7241	Intermediate Similarity	NPD753	Approved
0.7217	Intermediate Similarity	NPD4063	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5653	Discontinued
0.72	Intermediate Similarity	NPD3035	Approved
0.7185	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4409	Approved
0.7184	Intermediate Similarity	NPD4406	Approved
0.7176	Intermediate Similarity	NPD6358	Phase 2
0.7157	Intermediate Similarity	NPD5178	Approved
0.7154	Intermediate Similarity	NPD7733	Phase 2
0.7154	Intermediate Similarity	NPD7622	Phase 2
0.7143	Intermediate Similarity	NPD5993	Phase 1
0.7143	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7720	Phase 2
0.7132	Intermediate Similarity	NPD7086	Phase 2
0.7131	Intermediate Similarity	NPD4164	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5836	Discontinued
0.7121	Intermediate Similarity	NPD7254	Discontinued
0.712	Intermediate Similarity	NPD1482	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2031	Discontinued
0.7119	Intermediate Similarity	NPD3598	Phase 3
0.7097	Intermediate Similarity	NPD2584	Suspended
0.7087	Intermediate Similarity	NPD3626	Phase 3
0.7087	Intermediate Similarity	NPD4177	Approved
0.7087	Intermediate Similarity	NPD3040	Approved
0.7087	Intermediate Similarity	NPD4175	Approved
0.7083	Intermediate Similarity	NPD4574	Approved
0.7083	Intermediate Similarity	NPD4576	Approved
0.708	Intermediate Similarity	NPD2937	Phase 1
0.708	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2939	Approved
0.7077	Intermediate Similarity	NPD5296	Approved
0.7073	Intermediate Similarity	NPD1947	Approved
0.7064	Intermediate Similarity	NPD5963	Phase 2
0.7064	Intermediate Similarity	NPD5964	Phase 2
0.7063	Intermediate Similarity	NPD1321	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8323	Discontinued
0.7049	Intermediate Similarity	NPD5517	Phase 2
0.7049	Intermediate Similarity	NPD5516	Phase 2
0.7049	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4676	Approved
0.7027	Intermediate Similarity	NPD787	Suspended
0.7023	Intermediate Similarity	NPD3908	Approved
0.7023	Intermediate Similarity	NPD3577	Discontinued
0.7016	Intermediate Similarity	NPD1948	Approved
0.7016	Intermediate Similarity	NPD4478	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2010	Phase 3
0.7009	Intermediate Similarity	NPD5927	Discontinued
0.7008	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1052	Approved
0.7	Intermediate Similarity	NPD4680	Discontinued
0.7	Intermediate Similarity	NPD1053	Approved
0.7	Intermediate Similarity	NPD1051	Approved
0.6992	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7142	Discontinued
0.6991	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5578	Approved
0.6984	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2962	Approved
0.6984	Remote Similarity	NPD2961	Approved
0.6984	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1370	Approved
0.6975	Remote Similarity	NPD1373	Approved
0.6975	Remote Similarity	NPD1371	Approved
0.6975	Remote Similarity	NPD1374	Approved
0.697	Remote Similarity	NPD7106	Discontinued
0.697	Remote Similarity	NPD6073	Approved
0.6953	Remote Similarity	NPD4549	Discontinued
0.6934	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6564	Approved
0.6929	Remote Similarity	NPD6565	Approved
0.6929	Remote Similarity	NPD6563	Approved
0.6923	Remote Similarity	NPD1756	Approved
0.6923	Remote Similarity	NPD1752	Approved
0.6923	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD851	Approved
0.6917	Remote Similarity	NPD853	Approved
0.6917	Remote Similarity	NPD7541	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5915	Approved
0.6911	Remote Similarity	NPD6994	Approved
0.6911	Remote Similarity	NPD6993	Approved
0.6905	Remote Similarity	NPD5157	Phase 1
0.6905	Remote Similarity	NPD5159	Phase 2
0.6905	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2196	Discontinued
0.6899	Remote Similarity	NPD3063	Discontinued
0.6897	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2607	Approved
0.6887	Remote Similarity	NPD5675	Discontinued
0.6887	Remote Similarity	NPD3345	Approved
0.6885	Remote Similarity	NPD2115	Approved
0.6885	Remote Similarity	NPD2117	Pre-registration
0.6885	Remote Similarity	NPD2116	Approved
0.6884	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7437	Approved
0.688	Remote Similarity	NPD7436	Approved
0.687	Remote Similarity	NPD5747	Discontinued
0.687	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3642	Approved
0.6864	Remote Similarity	NPD3643	Approved
0.6864	Remote Similarity	NPD3644	Approved
0.6855	Remote Similarity	NPD4488	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6039	Approved
0.6842	Remote Similarity	NPD5103	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