NPASS Compound

Structure

NPC220698 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -3.0000 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 -0.5000 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 -2.0000 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 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 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 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 1 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 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 -1.7321 1.0000 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 -0.8660 2.5000 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 21 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 16 12 1 6 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 20 2 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 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.14
Volume:	327.357
LogP:	2.732
LogD:	2.563
LogS:	-3.195
# Rotatable Bonds:	4
TPSA:	55.12
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.806
Synthetic Accessibility Score:	2.232
Fsp3:	0.158
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:	-4.76
MDCK Permeability:	3.748539529624395e-05
Pgp-inhibitor:	0.39
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	97.23385620117188%
Volume Distribution (VD):	0.492
Pgp-substrate:	1.4183493852615356%

ADMET: Metabolism

CYP1A2-inhibitor:	0.173
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.546
CYP2C19-substrate:	0.643
CYP2C9-inhibitor:	0.695
CYP2C9-substrate:	0.248
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.84

ADMET: Excretion

Clearance (CL):	8.479
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.58
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.054
Carcinogencity:	0.179
Eye Corrosion:	0.003
Eye Irritation:	0.119
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC220698

Natural Product ID:	NPC220698
*Common Name:**	Diphenylalazine A
IUPAC Name:	(3S,6Z)-3-benzyl-6-benzylidene-1-methylpiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	UQQIPIPADMCILH-MUBYSKIDSA-N
Standard InCHI:	InChI=1S/C19H18N2O2/c1-21-17(13-15-10-6-3-7-11-15)18(22)20-16(19(21)23)12-14-8-4-2-5-9-14/h2-11,13,16H,12H2,1H3,(H,20,22)/b17-13-/t16-/m0/s1
SMILES:	OC1=N[C@@H](Cc2ccccc2)C(=O)N(/C/1=Cc1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079995
PubChem CID:	44614255
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
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711348]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919067]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China	2007-JUN	PMID[20550196]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24328302]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	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
EC50	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	27900.0	nM	PMID[469084]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[469084]

☑ 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 NPC220698 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	141
0.1-0.2	2157
0.2-0.3	11226
0.3-0.4	15604
0.4-0.5	10906
0.5-0.6	2070
0.6-0.7	533
0.7-0.8	54
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC45033
0.8319	Intermediate Similarity	NPC473418
0.8167	Intermediate Similarity	NPC315276
0.8167	Intermediate Similarity	NPC285926
0.8167	Intermediate Similarity	NPC14672
0.8151	Intermediate Similarity	NPC33742
0.8099	Intermediate Similarity	NPC470545
0.8088	Intermediate Similarity	NPC9373
0.8033	Intermediate Similarity	NPC470546
0.8017	Intermediate Similarity	NPC470544
0.784	Intermediate Similarity	NPC71684
0.7829	Intermediate Similarity	NPC111428
0.7829	Intermediate Similarity	NPC473322
0.7778	Intermediate Similarity	NPC473498
0.7769	Intermediate Similarity	NPC276949
0.7769	Intermediate Similarity	NPC35850
0.776	Intermediate Similarity	NPC200964
0.7717	Intermediate Similarity	NPC474082
0.7717	Intermediate Similarity	NPC175726
0.771	Intermediate Similarity	NPC255447
0.7634	Intermediate Similarity	NPC200589
0.7518	Intermediate Similarity	NPC254798
0.7482	Intermediate Similarity	NPC471680
0.748	Intermediate Similarity	NPC27833
0.7462	Intermediate Similarity	NPC101719
0.7455	Intermediate Similarity	NPC262393
0.744	Intermediate Similarity	NPC239357
0.7424	Intermediate Similarity	NPC469666
0.7391	Intermediate Similarity	NPC472258
0.7388	Intermediate Similarity	NPC257390
0.7385	Intermediate Similarity	NPC222466
0.7372	Intermediate Similarity	NPC313694
0.7372	Intermediate Similarity	NPC242159
0.7311	Intermediate Similarity	NPC275467
0.7308	Intermediate Similarity	NPC6975
0.7254	Intermediate Similarity	NPC16188
0.7246	Intermediate Similarity	NPC132636
0.7217	Intermediate Similarity	NPC256452
0.7209	Intermediate Similarity	NPC302169
0.719	Intermediate Similarity	NPC471447
0.7172	Intermediate Similarity	NPC233702
0.7154	Intermediate Similarity	NPC202521
0.7153	Intermediate Similarity	NPC474473
0.7132	Intermediate Similarity	NPC325479
0.7122	Intermediate Similarity	NPC77992
0.7117	Intermediate Similarity	NPC203076
0.7097	Intermediate Similarity	NPC319579
0.7094	Intermediate Similarity	NPC311242
0.7092	Intermediate Similarity	NPC161069
0.7086	Intermediate Similarity	NPC471052
0.7086	Intermediate Similarity	NPC471051
0.7086	Intermediate Similarity	NPC471053
0.7077	Intermediate Similarity	NPC476990
0.7068	Intermediate Similarity	NPC4974
0.7034	Intermediate Similarity	NPC322598
0.7029	Intermediate Similarity	NPC248283
0.7015	Intermediate Similarity	NPC136453
0.7007	Intermediate Similarity	NPC202198
0.7	Intermediate Similarity	NPC104345
0.7	Intermediate Similarity	NPC329375
0.6993	Remote Similarity	NPC209509
0.6992	Remote Similarity	NPC22746
0.6975	Remote Similarity	NPC12730
0.6974	Remote Similarity	NPC191863
0.6974	Remote Similarity	NPC289776
0.6974	Remote Similarity	NPC133470
0.697	Remote Similarity	NPC252878
0.6967	Remote Similarity	NPC167336
0.6963	Remote Similarity	NPC105114
0.6963	Remote Similarity	NPC239990
0.6963	Remote Similarity	NPC319766
0.6963	Remote Similarity	NPC152850
0.6963	Remote Similarity	NPC89923
0.6963	Remote Similarity	NPC71933
0.6959	Remote Similarity	NPC473002
0.6944	Remote Similarity	NPC262077
0.6934	Remote Similarity	NPC130309
0.6929	Remote Similarity	NPC127741
0.6928	Remote Similarity	NPC189116
0.6923	Remote Similarity	NPC314388
0.6923	Remote Similarity	NPC315283
0.6918	Remote Similarity	NPC13470
0.6917	Remote Similarity	NPC46427
0.6913	Remote Similarity	NPC469903
0.6901	Remote Similarity	NPC476989
0.6897	Remote Similarity	NPC138775
0.6879	Remote Similarity	NPC476133
0.6879	Remote Similarity	NPC470884
0.6879	Remote Similarity	NPC92784
0.6879	Remote Similarity	NPC98424
0.6879	Remote Similarity	NPC178662
0.6875	Remote Similarity	NPC316008
0.6875	Remote Similarity	NPC477217
0.6875	Remote Similarity	NPC313867
0.6875	Remote Similarity	NPC201244
0.6871	Remote Similarity	NPC7817
0.6871	Remote Similarity	NPC475168
0.6861	Remote Similarity	NPC300315
0.6857	Remote Similarity	NPC260045
0.6857	Remote Similarity	NPC79465
0.6857	Remote Similarity	NPC476102
0.6857	Remote Similarity	NPC474787
0.6857	Remote Similarity	NPC475318
0.6857	Remote Similarity	NPC118099
0.6857	Remote Similarity	NPC90194
0.6857	Remote Similarity	NPC474811
0.6857	Remote Similarity	NPC474855
0.6857	Remote Similarity	NPC475598
0.6857	Remote Similarity	NPC293377
0.6857	Remote Similarity	NPC151706
0.6857	Remote Similarity	NPC273907
0.6857	Remote Similarity	NPC76785
0.6857	Remote Similarity	NPC9687
0.6857	Remote Similarity	NPC49577
0.6849	Remote Similarity	NPC105717
0.6842	Remote Similarity	NPC473003
0.6838	Remote Similarity	NPC199738
0.6838	Remote Similarity	NPC71140
0.6838	Remote Similarity	NPC210950
0.6835	Remote Similarity	NPC279871
0.6831	Remote Similarity	NPC46098
0.6831	Remote Similarity	NPC153007
0.6831	Remote Similarity	NPC268841
0.6831	Remote Similarity	NPC307357
0.6828	Remote Similarity	NPC314358
0.6822	Remote Similarity	NPC473573
0.6821	Remote Similarity	NPC84317
0.6815	Remote Similarity	NPC474479
0.6812	Remote Similarity	NPC157311
0.6803	Remote Similarity	NPC164859
0.6783	Remote Similarity	NPC263493
0.6783	Remote Similarity	NPC269398
0.6781	Remote Similarity	NPC135121
0.678	Remote Similarity	NPC303045
0.678	Remote Similarity	NPC161972
0.6772	Remote Similarity	NPC275410
0.6765	Remote Similarity	NPC477937
0.6763	Remote Similarity	NPC44805
0.6763	Remote Similarity	NPC8761
0.6763	Remote Similarity	NPC246079
0.6754	Remote Similarity	NPC473031
0.6738	Remote Similarity	NPC29650
0.6736	Remote Similarity	NPC139326
0.6733	Remote Similarity	NPC470902
0.6732	Remote Similarity	NPC469243
0.6732	Remote Similarity	NPC469902
0.673	Remote Similarity	NPC477462
0.6726	Remote Similarity	NPC3210
0.6719	Remote Similarity	NPC474584
0.6714	Remote Similarity	NPC287401
0.6713	Remote Similarity	NPC163392
0.6713	Remote Similarity	NPC239762
0.6712	Remote Similarity	NPC473804
0.671	Remote Similarity	NPC223207
0.6708	Remote Similarity	NPC269750
0.6708	Remote Similarity	NPC194671
0.6694	Remote Similarity	NPC211551
0.6694	Remote Similarity	NPC67043
0.6692	Remote Similarity	NPC190663
0.6692	Remote Similarity	NPC80150
0.669	Remote Similarity	NPC476978
0.669	Remote Similarity	NPC138365
0.669	Remote Similarity	NPC52748
0.669	Remote Similarity	NPC471265
0.669	Remote Similarity	NPC471264
0.669	Remote Similarity	NPC68865
0.6688	Remote Similarity	NPC241794
0.6667	Remote Similarity	NPC150863
0.6667	Remote Similarity	NPC311658
0.6667	Remote Similarity	NPC119569
0.6667	Remote Similarity	NPC248670
0.6667	Remote Similarity	NPC287757
0.6667	Remote Similarity	NPC122590
0.6667	Remote Similarity	NPC319320
0.6667	Remote Similarity	NPC290755
0.6667	Remote Similarity	NPC226438
0.6667	Remote Similarity	NPC286551
0.6667	Remote Similarity	NPC471771
0.6667	Remote Similarity	NPC473341
0.6667	Remote Similarity	NPC304074
0.6644	Remote Similarity	NPC5620
0.6644	Remote Similarity	NPC473491
0.6643	Remote Similarity	NPC89489
0.6641	Remote Similarity	NPC475013
0.664	Remote Similarity	NPC274089
0.664	Remote Similarity	NPC191215
0.664	Remote Similarity	NPC327481
0.6624	Remote Similarity	NPC141957
0.6624	Remote Similarity	NPC328649
0.6623	Remote Similarity	NPC154478
0.6623	Remote Similarity	NPC475544
0.6621	Remote Similarity	NPC197682
0.6619	Remote Similarity	NPC179224
0.6618	Remote Similarity	NPC285394
0.6607	Remote Similarity	NPC14326
0.6599	Remote Similarity	NPC81026
0.6597	Remote Similarity	NPC476259
0.6596	Remote Similarity	NPC244866
0.6594	Remote Similarity	NPC476950
0.6593	Remote Similarity	NPC160493

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 NPC220698 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	118
0.1-0.2	444
0.2-0.3	1065
0.3-0.4	1558
0.4-0.5	3619
0.5-0.6	1902
0.6-0.7	422
0.7-0.8	22
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
0.7778	Intermediate Similarity	NPD7130	Phase 3
0.7615	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD480	Approved
0.7521	Intermediate Similarity	NPD2583	Phase 2
0.7481	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2031	Discontinued
0.7462	Intermediate Similarity	NPD6792	Phase 3
0.7419	Intermediate Similarity	NPD3551	Approved
0.7385	Intermediate Similarity	NPD4677	Discontinued
0.7323	Intermediate Similarity	NPD6343	Approved
0.7323	Intermediate Similarity	NPD6345	Approved
0.7308	Intermediate Similarity	NPD2584	Suspended
0.7305	Intermediate Similarity	NPD1968	Approved
0.7305	Intermediate Similarity	NPD1967	Approved
0.728	Intermediate Similarity	NPD5631	Phase 3
0.7273	Intermediate Similarity	NPD3029	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5581	Approved
0.7234	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7720	Phase 2
0.7209	Intermediate Similarity	NPD6806	Phase 1
0.7197	Intermediate Similarity	NPD3125	Approved
0.7185	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3123	Discovery
0.7165	Intermediate Similarity	NPD7679	Phase 2
0.7164	Intermediate Similarity	NPD3626	Phase 3
0.7154	Intermediate Similarity	NPD3581	Discontinued
0.7143	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4803	Discontinued
0.7133	Intermediate Similarity	NPD6017	Discontinued
0.7132	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7131	Phase 3
0.7109	Intermediate Similarity	NPD5991	Approved
0.7109	Intermediate Similarity	NPD3806	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5990	Approved
0.7099	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5103	Approved
0.7071	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5181	Approved
0.7063	Intermediate Similarity	NPD5180	Approved
0.7063	Intermediate Similarity	NPD5179	Approved
0.7063	Intermediate Similarity	NPD5481	Discontinued
0.7045	Intermediate Similarity	NPD3071	Approved
0.7045	Intermediate Similarity	NPD3073	Approved
0.7045	Intermediate Similarity	NPD3072	Approved
0.704	Intermediate Similarity	NPD4991	Discontinued
0.704	Intermediate Similarity	NPD753	Approved
0.7031	Intermediate Similarity	NPD1344	Phase 2
0.7031	Intermediate Similarity	NPD4431	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6623	Phase 3
0.7015	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8323	Discontinued
0.7014	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6024	Approved
0.7	Intermediate Similarity	NPD6294	Approved
0.7	Intermediate Similarity	NPD6027	Approved
0.7	Intermediate Similarity	NPD6295	Approved
0.6986	Remote Similarity	NPD4432	Discontinued
0.6985	Remote Similarity	NPD4125	Approved
0.6985	Remote Similarity	NPD5263	Approved
0.6978	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3908	Approved
0.6972	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4761	Approved
0.697	Remote Similarity	NPD4762	Approved
0.6967	Remote Similarity	NPD999	Phase 2
0.6964	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.696	Remote Similarity	NPD3642	Approved
0.696	Remote Similarity	NPD3644	Approved
0.696	Remote Similarity	NPD3643	Approved
0.695	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4655	Approved
0.6949	Remote Similarity	NPD4657	Approved
0.694	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5578	Approved
0.6934	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8172	Phase 2
0.6929	Remote Similarity	NPD8173	Phase 2
0.6929	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2014	Approved
0.6918	Remote Similarity	NPD2016	Approved
0.6918	Remote Similarity	NPD2013	Approved
0.6912	Remote Similarity	NPD1781	Discontinued
0.6906	Remote Similarity	NPD5272	Discontinued
0.6884	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1330	Phase 2
0.688	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6901	Phase 3
0.6875	Remote Similarity	NPD2508	Discontinued
0.6875	Remote Similarity	NPD5024	Approved
0.6861	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8643	Discontinued
0.6842	Remote Similarity	NPD1948	Approved
0.6842	Remote Similarity	NPD3624	Phase 2
0.6835	Remote Similarity	NPD7086	Phase 2
0.6835	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD941	Approved
0.6831	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3822	Approved
0.6824	Remote Similarity	NPD3820	Approved
0.6824	Remote Similarity	NPD3821	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1099	Approved
0.6807	Remote Similarity	NPD1100	Approved
0.6806	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6088	Approved
0.6803	Remote Similarity	NPD3282	Phase 1
0.6803	Remote Similarity	NPD3283	Phase 3
0.6794	Remote Similarity	NPD998	Approved
0.6791	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4177	Approved
0.6788	Remote Similarity	NPD3040	Approved
0.6788	Remote Similarity	NPD4175	Approved
0.678	Remote Similarity	NPD4094	Approved
0.6777	Remote Similarity	NPD5630	Phase 1
0.6767	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1947	Approved
0.6763	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4942	Approved
0.6757	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5941	Approved
0.6757	Remote Similarity	NPD5942	Approved
0.675	Remote Similarity	NPD466	Approved
0.6744	Remote Similarity	NPD2543	Discontinued
0.6744	Remote Similarity	NPD3867	Phase 2
0.6739	Remote Similarity	NPD5131	Approved
0.6739	Remote Similarity	NPD4676	Approved
0.6735	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7599	Phase 2
0.6716	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4151	Approved
0.6715	Remote Similarity	NPD5993	Phase 1
0.6714	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1767	Approved
0.6694	Remote Similarity	NPD1761	Approved
0.6694	Remote Similarity	NPD1766	Approved
0.6694	Remote Similarity	NPD1765	Approved
0.6694	Remote Similarity	NPD742	Approved
0.6694	Remote Similarity	NPD1763	Approved
0.6693	Remote Similarity	NPD4254	Approved
0.6693	Remote Similarity	NPD4253	Approved
0.6691	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.669	Remote Similarity	NPD8125	Discontinued
0.669	Remote Similarity	NPD6073	Approved
0.6688	Remote Similarity	NPD7600	Phase 2
0.6667	Remote Similarity	NPD2997	Approved
0.6667	Remote Similarity	NPD23	Approved
0.6667	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7450	Phase 2
0.6667	Remote Similarity	NPD3598	Phase 3
0.6667	Remote Similarity	NPD3000	Approved
0.6667	Remote Similarity	NPD2998	Approved
0.6667	Remote Similarity	NPD6408	Phase 1
0.6645	Remote Similarity	NPD2891	Approved
0.6643	Remote Similarity	NPD6358	Phase 2
0.6642	Remote Similarity	NPD2840	Approved
0.6622	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3577	Discontinued
0.662	Remote Similarity	NPD2791	Discontinued
0.6619	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5157	Phase 1
0.6618	Remote Similarity	NPD3549	Approved
0.6618	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5159	Phase 2
0.6618	Remote Similarity	NPD3547	Approved
0.66	Remote Similarity	NPD6144	Discontinued
0.66	Remote Similarity	NPD5748	Phase 2
0.66	Remote Similarity	NPD7613	Discontinued
0.6597	Remote Similarity	NPD7142	Discontinued
0.6597	Remote Similarity	NPD7254	Discontinued
0.6593	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD813	Approved
0.6583	Remote Similarity	NPD2895	Discontinued
0.6583	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1582	Approved
0.6577	Remote Similarity	NPD1581	Approved
0.6573	Remote Similarity	NPD7192	Discontinued
0.6571	Remote Similarity	NPD2754	Discontinued
0.6569	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6325	Discontinued
0.6569	Remote Similarity	NPD2962	Approved
0.6569	Remote Similarity	NPD2961	Approved
0.6567	Remote Similarity	NPD4733	Approved
0.6567	Remote Similarity	NPD3064	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD1323	Discontinued
0.656	Remote Similarity	NPD2197	Approved
0.656	Remote Similarity	NPD2192	Approved
0.656	Remote Similarity	NPD1018	Approved
0.6558	Remote Similarity	NPD7011	Discontinued
0.6556	Remote Similarity	NPD6575	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