NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.06
Volume:	158.84
LogP:	0.311
LogD:	0.748
LogS:	-2.371
# Rotatable Bonds:	0
TPSA:	61.96
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	3.017
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.873
MDCK Permeability:	5.16757017976488e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.343
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.691

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	18.249109268188477%
Volume Distribution (VD):	1.173
Pgp-substrate:	82.64408111572266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.491
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.185
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.847
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.424
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	7.131
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.68
AMES Toxicity:	0.631
Rat Oral Acute Toxicity:	0.171
Maximum Recommended Daily Dose:	0.403
Skin Sensitization:	0.225
Carcinogencity:	0.121
Eye Corrosion:	0.004
Eye Irritation:	0.157
Respiratory Toxicity:	0.135

Download Data

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

Natural Product: NPC233380

Natural Product ID:	NPC233380
*Common Name:**	Aldisin
IUPAC Name:	1,5,6,7-tetrahydropyrrolo[2,3-c]azepine-4,8-dione
Synonyms:	Aldisin
Standard InCHIKey:	AAPGLCCSVSGLFH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8N2O2/c11-6-2-4-10-8(12)7-5(6)1-3-9-7/h1,3,9H,2,4H2,(H,10,12)
SMILES:	c1c[nH]c2c1C(=O)CCNC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL357047
PubChem CID:	3085877
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001990] Pyrroloazepines

*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
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	Philippine	n.a.	PMID[11784156]
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12816422]
NPO32816	Axinella carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043426]
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23684893]
NPO32816	Axinella carteri	Species	Axinellidae	Eukaryota	n.a.	Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[9548881]
NPO6961	Vernonia arctioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3926	Ptilometra australis	Species	Ptilometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8562	Echinocystis fabacea	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7079	Stylissa massa	Species	Axinellidae	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
GI50	4
IC50	5

Activity Type	# Activity
Cell Line	6
Individual Protein	2
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT491	Individual Protein	Dual specificity mitogen-activated protein kinase kinase 1	Homo sapiens	IC50	=	2500.0	nM	PMID[497174]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	IC50	>	2500.0	nM	PMID[497174]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	>	10000.0	nM	PMID[497174]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	10000.0	nM	PMID[497174]
NPT81	Cell Line	A549	Homo sapiens	GI50	>	100000.0	nM	PMID[497177]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	>	100000.0	nM	PMID[497177]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	100000.0	nM	PMID[497177]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	>	100000.0	nM	PMID[497177]
NPT490	Protein Family	Serine/threonine-protein kinase RAF and Dual specificity mitogen-activated protein kinase kinase 1 (Raf/MEK)	Homo sapiens	IC50	>	2500.0	nM	PMID[497174]

☑ 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 NPC233380 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	940
0.1-0.2	11887
0.2-0.3	19332
0.3-0.4	5246
0.4-0.5	2258
0.5-0.6	1969
0.6-0.7	860
0.7-0.8	185
0.8-0.85	18
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8868	High Similarity	NPC2414
0.8412	Intermediate Similarity	NPC477003
0.8228	Intermediate Similarity	NPC105811
0.8224	Intermediate Similarity	NPC291517
0.816	Intermediate Similarity	NPC474492
0.8137	Intermediate Similarity	NPC251391
0.8125	Intermediate Similarity	NPC476460
0.8125	Intermediate Similarity	NPC471655
0.8101	Intermediate Similarity	NPC467188
0.8075	Intermediate Similarity	NPC70406
0.8063	Intermediate Similarity	NPC123906
0.8	Intermediate Similarity	NPC470680
0.8	Intermediate Similarity	NPC100104
0.7988	Intermediate Similarity	NPC213914
0.7963	Intermediate Similarity	NPC472260
0.7907	Intermediate Similarity	NPC284775
0.7874	Intermediate Similarity	NPC191415
0.7871	Intermediate Similarity	NPC23215
0.7866	Intermediate Similarity	NPC209362
0.7866	Intermediate Similarity	NPC229055
0.7838	Intermediate Similarity	NPC317701
0.7818	Intermediate Similarity	NPC74357
0.7814	Intermediate Similarity	NPC477004
0.7791	Intermediate Similarity	NPC469529
0.7791	Intermediate Similarity	NPC313889
0.7791	Intermediate Similarity	NPC37268
0.7751	Intermediate Similarity	NPC42372
0.7735	Intermediate Similarity	NPC326422
0.7697	Intermediate Similarity	NPC476527
0.7692	Intermediate Similarity	NPC274981
0.7669	Intermediate Similarity	NPC100726
0.7667	Intermediate Similarity	NPC324091
0.764	Intermediate Similarity	NPC133003
0.7627	Intermediate Similarity	NPC102755
0.7614	Intermediate Similarity	NPC477042
0.7609	Intermediate Similarity	NPC167710
0.7586	Intermediate Similarity	NPC293216
0.7576	Intermediate Similarity	NPC473878
0.7572	Intermediate Similarity	NPC54214
0.7572	Intermediate Similarity	NPC262338
0.7571	Intermediate Similarity	NPC472861
0.7571	Intermediate Similarity	NPC184932
0.7544	Intermediate Similarity	NPC115232
0.7543	Intermediate Similarity	NPC151635
0.7541	Intermediate Similarity	NPC304203
0.753	Intermediate Similarity	NPC217021
0.753	Intermediate Similarity	NPC470679
0.75	Intermediate Similarity	NPC202812
0.75	Intermediate Similarity	NPC114637
0.75	Intermediate Similarity	NPC83774
0.7459	Intermediate Similarity	NPC79356
0.7459	Intermediate Similarity	NPC102592
0.7458	Intermediate Similarity	NPC11126
0.7444	Intermediate Similarity	NPC311282
0.7416	Intermediate Similarity	NPC73994
0.7416	Intermediate Similarity	NPC61011
0.7414	Intermediate Similarity	NPC471943
0.7377	Intermediate Similarity	NPC154339
0.7374	Intermediate Similarity	NPC470677
0.7368	Intermediate Similarity	NPC473706
0.7356	Intermediate Similarity	NPC70949
0.7333	Intermediate Similarity	NPC260041
0.733	Intermediate Similarity	NPC252572
0.7329	Intermediate Similarity	NPC472288
0.7318	Intermediate Similarity	NPC79777
0.7296	Intermediate Similarity	NPC20021
0.7293	Intermediate Similarity	NPC46895
0.7293	Intermediate Similarity	NPC228835
0.7273	Intermediate Similarity	NPC476526
0.7273	Intermediate Similarity	NPC329765
0.7273	Intermediate Similarity	NPC48117
0.7273	Intermediate Similarity	NPC469976
0.7258	Intermediate Similarity	NPC267343
0.7253	Intermediate Similarity	NPC99939
0.7253	Intermediate Similarity	NPC308931
0.7249	Intermediate Similarity	NPC237414
0.7238	Intermediate Similarity	NPC470205
0.7235	Intermediate Similarity	NPC33229
0.7234	Intermediate Similarity	NPC475286
0.7234	Intermediate Similarity	NPC174281
0.7228	Intermediate Similarity	NPC209917
0.7225	Intermediate Similarity	NPC242116
0.7222	Intermediate Similarity	NPC65408
0.7222	Intermediate Similarity	NPC234403
0.7215	Intermediate Similarity	NPC71236
0.7209	Intermediate Similarity	NPC80681
0.7207	Intermediate Similarity	NPC240088
0.7207	Intermediate Similarity	NPC473380
0.7202	Intermediate Similarity	NPC102664
0.72	Intermediate Similarity	NPC474696
0.7198	Intermediate Similarity	NPC110158
0.7184	Intermediate Similarity	NPC265100
0.7184	Intermediate Similarity	NPC206148
0.7174	Intermediate Similarity	NPC278434
0.7174	Intermediate Similarity	NPC17059
0.7167	Intermediate Similarity	NPC265710
0.7158	Intermediate Similarity	NPC136957
0.7158	Intermediate Similarity	NPC19696
0.7158	Intermediate Similarity	NPC476423
0.7157	Intermediate Similarity	NPC471193
0.7157	Intermediate Similarity	NPC471194
0.7152	Intermediate Similarity	NPC129412
0.7152	Intermediate Similarity	NPC114033
0.7152	Intermediate Similarity	NPC58268
0.7152	Intermediate Similarity	NPC101130
0.7151	Intermediate Similarity	NPC138370
0.7151	Intermediate Similarity	NPC27296
0.7143	Intermediate Similarity	NPC150592
0.7128	Intermediate Similarity	NPC116555
0.7127	Intermediate Similarity	NPC314281
0.7127	Intermediate Similarity	NPC16659
0.7127	Intermediate Similarity	NPC40530
0.7126	Intermediate Similarity	NPC214106
0.712	Intermediate Similarity	NPC94752
0.7112	Intermediate Similarity	NPC216550
0.7104	Intermediate Similarity	NPC21429
0.7086	Intermediate Similarity	NPC73687
0.7083	Intermediate Similarity	NPC471944
0.7081	Intermediate Similarity	NPC23476
0.7081	Intermediate Similarity	NPC477415
0.7081	Intermediate Similarity	NPC474259
0.7074	Intermediate Similarity	NPC473821
0.7072	Intermediate Similarity	NPC55772
0.7059	Intermediate Similarity	NPC210123
0.7055	Intermediate Similarity	NPC195704
0.7055	Intermediate Similarity	NPC98156
0.7055	Intermediate Similarity	NPC292434
0.7055	Intermediate Similarity	NPC138596
0.7055	Intermediate Similarity	NPC14448
0.7055	Intermediate Similarity	NPC167200
0.7055	Intermediate Similarity	NPC64661
0.7055	Intermediate Similarity	NPC200397
0.7053	Intermediate Similarity	NPC74153
0.7049	Intermediate Similarity	NPC270834
0.7045	Intermediate Similarity	NPC474383
0.7044	Intermediate Similarity	NPC471589
0.7044	Intermediate Similarity	NPC313823
0.7041	Intermediate Similarity	NPC476524
0.7041	Intermediate Similarity	NPC476525
0.7039	Intermediate Similarity	NPC271927
0.7027	Intermediate Similarity	NPC17273
0.7027	Intermediate Similarity	NPC135601
0.7027	Intermediate Similarity	NPC141612
0.7021	Intermediate Similarity	NPC47190
0.702	Intermediate Similarity	NPC72956
0.7017	Intermediate Similarity	NPC84827
0.7017	Intermediate Similarity	NPC14113
0.7017	Intermediate Similarity	NPC145885
0.7016	Intermediate Similarity	NPC477044
0.7016	Intermediate Similarity	NPC477041
0.7006	Intermediate Similarity	NPC190296
0.7	Intermediate Similarity	NPC110500
0.7	Intermediate Similarity	NPC203468
0.7	Intermediate Similarity	NPC149155
0.6988	Remote Similarity	NPC3698
0.6988	Remote Similarity	NPC244087
0.6988	Remote Similarity	NPC129753
0.6988	Remote Similarity	NPC205604
0.6988	Remote Similarity	NPC286529
0.6988	Remote Similarity	NPC74928
0.6988	Remote Similarity	NPC59839
0.6988	Remote Similarity	NPC48171
0.6988	Remote Similarity	NPC302717
0.6988	Remote Similarity	NPC77582
0.6988	Remote Similarity	NPC169308
0.6988	Remote Similarity	NPC97230
0.6988	Remote Similarity	NPC209281
0.6988	Remote Similarity	NPC12831
0.6985	Remote Similarity	NPC153980
0.6985	Remote Similarity	NPC470702
0.6985	Remote Similarity	NPC6865
0.6985	Remote Similarity	NPC473218
0.6983	Remote Similarity	NPC302647
0.6978	Remote Similarity	NPC248041
0.6978	Remote Similarity	NPC126709
0.6978	Remote Similarity	NPC283219
0.6977	Remote Similarity	NPC200214
0.6975	Remote Similarity	NPC330326
0.6966	Remote Similarity	NPC78020
0.6961	Remote Similarity	NPC476419
0.6961	Remote Similarity	NPC267885
0.6951	Remote Similarity	NPC96102
0.695	Remote Similarity	NPC470703
0.6947	Remote Similarity	NPC294693
0.6944	Remote Similarity	NPC161861
0.6944	Remote Similarity	NPC80528
0.694	Remote Similarity	NPC88110
0.694	Remote Similarity	NPC182940
0.6936	Remote Similarity	NPC474236
0.6931	Remote Similarity	NPC267811
0.6923	Remote Similarity	NPC159856
0.6923	Remote Similarity	NPC470440
0.6923	Remote Similarity	NPC111275
0.6923	Remote Similarity	NPC314372
0.6915	Remote Similarity	NPC469489
0.6915	Remote Similarity	NPC475874
0.6914	Remote Similarity	NPC82295
0.6909	Remote Similarity	NPC105127
0.6909	Remote Similarity	NPC84911
0.6893	Remote Similarity	NPC476418

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 NPC233380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	858
0.2-0.3	1253
0.3-0.4	2346
0.4-0.5	2340
0.5-0.6	1599
0.6-0.7	429
0.7-0.8	39
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
0.7636	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD460	Discontinued
0.7532	Intermediate Similarity	NPD272	Approved
0.7472	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD2479	Phase 3
0.7416	Intermediate Similarity	NPD2481	Approved
0.7416	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1096	Discontinued
0.7374	Intermediate Similarity	NPD3178	Discontinued
0.7333	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1952	Discontinued
0.7308	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4848	Phase 1
0.7246	Intermediate Similarity	NPD1270	Approved
0.7238	Intermediate Similarity	NPD3319	Phase 1
0.7238	Intermediate Similarity	NPD3320	Approved
0.7238	Intermediate Similarity	NPD3318	Approved
0.7222	Intermediate Similarity	NPD1618	Phase 2
0.7222	Intermediate Similarity	NPD201	Phase 2
0.7222	Intermediate Similarity	NPD200	Phase 2
0.7213	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4922	Phase 2
0.7195	Intermediate Similarity	NPD9599	Approved
0.7193	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1506	Discontinued
0.7159	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2008	Discontinued
0.7092	Intermediate Similarity	NPD1600	Suspended
0.7081	Intermediate Similarity	NPD4988	Discontinued
0.7062	Intermediate Similarity	NPD1343	Approved
0.7045	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7619	Phase 3
0.7037	Intermediate Similarity	NPD7618	Phase 3
0.7033	Intermediate Similarity	NPD3927	Phase 2
0.7005	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD482	Approved
0.7	Intermediate Similarity	NPD4883	Approved
0.6975	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9100	Approved
0.6974	Remote Similarity	NPD3947	Discontinued
0.6961	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1031	Discontinued
0.6936	Remote Similarity	NPD2061	Approved
0.6919	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5685	Approved
0.6915	Remote Similarity	NPD5686	Approved
0.6914	Remote Similarity	NPD1630	Approved
0.6911	Remote Similarity	NPD2290	Phase 3
0.6911	Remote Similarity	NPD2289	Phase 3
0.69	Remote Similarity	NPD2411	Approved
0.6897	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3583	Phase 2
0.6878	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD2443	Approved
0.6869	Remote Similarity	NPD2442	Approved
0.6868	Remote Similarity	NPD4075	Phase 2
0.6865	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5199	Approved
0.6863	Remote Similarity	NPD5198	Approved
0.6856	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1575	Approved
0.6833	Remote Similarity	NPD1573	Approved
0.6828	Remote Similarity	NPD7564	Discontinued
0.6828	Remote Similarity	NPD2096	Phase 2
0.6828	Remote Similarity	NPD2091	Phase 2
0.6826	Remote Similarity	NPD786	Approved
0.6825	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5017	Discontinued
0.6818	Remote Similarity	NPD2214	Approved
0.6818	Remote Similarity	NPD2213	Approved
0.6813	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6173	Approved
0.6804	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4299	Phase 1
0.68	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD1631	Approved
0.6798	Remote Similarity	NPD3389	Approved
0.6798	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3394	Approved
0.6798	Remote Similarity	NPD3393	Approved
0.6796	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2509	Approved
0.6784	Remote Similarity	NPD2510	Approved
0.6784	Remote Similarity	NPD6459	Phase 2
0.6782	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6787	Phase 2
0.6774	Remote Similarity	NPD2092	Phase 2
0.6774	Remote Similarity	NPD2095	Phase 2
0.6774	Remote Similarity	NPD2094	Phase 2
0.6758	Remote Similarity	NPD4524	Discontinued
0.6746	Remote Similarity	NPD1722	Approved
0.6742	Remote Similarity	NPD6771	Discontinued
0.6742	Remote Similarity	NPD5400	Approved
0.6736	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2405	Phase 3
0.6716	Remote Similarity	NPD4051	Discontinued
0.6702	Remote Similarity	NPD1658	Discontinued
0.6701	Remote Similarity	NPD6664	Approved
0.6686	Remote Similarity	NPD107	Approved
0.6684	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5473	Discontinued
0.6667	Remote Similarity	NPD2408	Discontinued
0.6667	Remote Similarity	NPD1982	Phase 1
0.6667	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD750	Phase 2
0.6667	Remote Similarity	NPD7026	Phase 2
0.6633	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3961	Discontinued
0.6613	Remote Similarity	NPD3078	Approved
0.6613	Remote Similarity	NPD3079	Approved
0.6613	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3076	Approved
0.6613	Remote Similarity	NPD3077	Approved
0.6606	Remote Similarity	NPD803	Phase 1
0.6601	Remote Similarity	NPD6152	Phase 1
0.66	Remote Similarity	NPD3967	Approved
0.6598	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5853	Phase 3
0.6598	Remote Similarity	NPD5855	Phase 3
0.6595	Remote Similarity	NPD6044	Discontinued
0.6592	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6176	Phase 1
0.6582	Remote Similarity	NPD7459	Phase 2
0.6578	Remote Similarity	NPD1643	Phase 3
0.6567	Remote Similarity	NPD3411	Phase 2
0.6567	Remote Similarity	NPD3410	Approved
0.6567	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD991	Phase 2
0.6564	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD2753	Discontinued
0.655	Remote Similarity	NPD5901	Discontinued
0.6548	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5854	Approved
0.6545	Remote Similarity	NPD3246	Discontinued
0.6541	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1586	Approved
0.6538	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD9075	Approved
0.6532	Remote Similarity	NPD9074	Approved
0.6531	Remote Similarity	NPD5446	Phase 2
0.6524	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1591	Approved
0.6514	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3100	Discontinued
0.6507	Remote Similarity	NPD6210	Phase 3
0.6505	Remote Similarity	NPD3238	Discontinued
0.6502	Remote Similarity	NPD3968	Approved
0.6495	Remote Similarity	NPD4376	Phase 3
0.6489	Remote Similarity	NPD5146	Suspended
0.6488	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD9357	Approved
0.6477	Remote Similarity	NPD2172	Phase 1
0.6474	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD9271	Approved
0.6456	Remote Similarity	NPD9396	Approved
0.6456	Remote Similarity	NPD9392	Approved
0.6456	Remote Similarity	NPD5888	Phase 2
0.6453	Remote Similarity	NPD5421	Clinical (unspecified phase)
0.645	Remote Similarity	NPD2881	Approved
0.645	Remote Similarity	NPD2879	Approved
0.645	Remote Similarity	NPD7187	Phase 2
0.6442	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD510	Phase 1
0.6439	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1587	Approved
0.6436	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD923	Approved
0.6425	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7970	Approved
0.6419	Remote Similarity	NPD1659	Phase 1
0.6417	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6665	Discontinued
0.6409	Remote Similarity	NPD1403	Approved
0.6409	Remote Similarity	NPD1404	Approved
0.6406	Remote Similarity	NPD6217	Discontinued
0.6402	Remote Similarity	NPD9583	Approved
0.64	Remote Similarity	NPD3890	Phase 2
0.64	Remote Similarity	NPD3891	Phase 2
0.6398	Remote Similarity	NPD9598	Discontinued
0.6398	Remote Similarity	NPD268	Approved
0.6398	Remote Similarity	NPD270	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