NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.08
Volume:	234.723
LogP:	2.294
LogD:	2.382
LogS:	-3.012
# Rotatable Bonds:	1
TPSA:	45.75
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	2.069
Fsp3:	0.0
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:	-4.661
MDCK Permeability:	2.3229622456710786e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.181
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.364
Plasma Protein Binding (PPB):	73.62828826904297%
Volume Distribution (VD):	1.135
Pgp-substrate:	15.135930061340332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.893
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.45
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.671
CYP2D6-substrate:	0.54
CYP3A4-inhibitor:	0.914
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	8.654
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.231
Human Hepatotoxicity (H-HT):	0.392
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.48
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.491
Skin Sensitization:	0.582
Carcinogencity:	0.065
Eye Corrosion:	0.004
Eye Irritation:	0.372
Respiratory Toxicity:	0.509

Download Data

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

Natural Product: NPC97367

Natural Product ID:	NPC97367
*Common Name:**	Lophocladine A
IUPAC Name:	4-phenyl-2H-2,7-naphthyridin-1-one
Synonyms:
Standard InCHIKey:	JIWHQPVTDQXELV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10N2O/c17-14-13-8-15-7-6-11(13)12(9-16-14)10-4-2-1-3-5-10/h1-9H,(H,16,17)
SMILES:	Oc1ncc(c2c1cncc2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472895
PubChem CID:	11708368
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002317] Phenylpyridines

*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
NPO32709	lophocladia sp.	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643042]

☑ 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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Inhibition	=	50.0	%	PMID[538625]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[538625]

☑ 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 NPC97367 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	734
0.1-0.2	5175
0.2-0.3	12025
0.3-0.4	13808
0.4-0.5	6869
0.5-0.6	2701
0.6-0.7	1201
0.7-0.8	177
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8805	High Similarity	NPC471178
0.8679	High Similarity	NPC471177
0.8679	High Similarity	NPC59779
0.8679	High Similarity	NPC124542
0.8395	Intermediate Similarity	NPC473057
0.8391	Intermediate Similarity	NPC329541
0.8182	Intermediate Similarity	NPC108469
0.8161	Intermediate Similarity	NPC472289
0.7933	Intermediate Similarity	NPC212125
0.7879	Intermediate Similarity	NPC84508
0.7831	Intermediate Similarity	NPC25899
0.7815	Intermediate Similarity	NPC306397
0.78	Intermediate Similarity	NPC151489
0.7784	Intermediate Similarity	NPC48192
0.7765	Intermediate Similarity	NPC473764
0.7765	Intermediate Similarity	NPC314940
0.7749	Intermediate Similarity	NPC237740
0.7736	Intermediate Similarity	NPC60553
0.7701	Intermediate Similarity	NPC477113
0.7701	Intermediate Similarity	NPC232340
0.7701	Intermediate Similarity	NPC164340
0.7697	Intermediate Similarity	NPC165370
0.7697	Intermediate Similarity	NPC46580
0.7688	Intermediate Similarity	NPC203754
0.7688	Intermediate Similarity	NPC150048
0.7688	Intermediate Similarity	NPC53144
0.7674	Intermediate Similarity	NPC471294
0.767	Intermediate Similarity	NPC220765
0.7663	Intermediate Similarity	NPC287437
0.7661	Intermediate Similarity	NPC164664
0.7643	Intermediate Similarity	NPC29702
0.7627	Intermediate Similarity	NPC204717
0.7624	Intermediate Similarity	NPC324149
0.7619	Intermediate Similarity	NPC477111
0.7613	Intermediate Similarity	NPC324611
0.7594	Intermediate Similarity	NPC200836
0.7584	Intermediate Similarity	NPC314002
0.7582	Intermediate Similarity	NPC471313
0.7582	Intermediate Similarity	NPC289786
0.7582	Intermediate Similarity	NPC471311
0.7574	Intermediate Similarity	NPC315214
0.7574	Intermediate Similarity	NPC47298
0.7572	Intermediate Similarity	NPC259545
0.7571	Intermediate Similarity	NPC133306
0.7553	Intermediate Similarity	NPC475070
0.7544	Intermediate Similarity	NPC98187
0.7542	Intermediate Similarity	NPC171171
0.754	Intermediate Similarity	NPC211813
0.7529	Intermediate Similarity	NPC32028
0.7529	Intermediate Similarity	NPC159319
0.7528	Intermediate Similarity	NPC284559
0.7527	Intermediate Similarity	NPC99666
0.7526	Intermediate Similarity	NPC477110
0.7526	Intermediate Similarity	NPC18348
0.7515	Intermediate Similarity	NPC131718
0.7514	Intermediate Similarity	NPC192315
0.75	Intermediate Similarity	NPC256893
0.75	Intermediate Similarity	NPC254762
0.75	Intermediate Similarity	NPC473053
0.7473	Intermediate Similarity	NPC476167
0.7472	Intermediate Similarity	NPC48938
0.7471	Intermediate Similarity	NPC208060
0.7459	Intermediate Similarity	NPC77555
0.7459	Intermediate Similarity	NPC44354
0.745	Intermediate Similarity	NPC91958
0.7448	Intermediate Similarity	NPC85273
0.7446	Intermediate Similarity	NPC146724
0.7443	Intermediate Similarity	NPC184964
0.7443	Intermediate Similarity	NPC96890
0.7439	Intermediate Similarity	NPC161292
0.7423	Intermediate Similarity	NPC471323
0.7421	Intermediate Similarity	NPC470164
0.7421	Intermediate Similarity	NPC323345
0.7416	Intermediate Similarity	NPC470474
0.7414	Intermediate Similarity	NPC252590
0.7411	Intermediate Similarity	NPC193267
0.7411	Intermediate Similarity	NPC213530
0.7405	Intermediate Similarity	NPC242209
0.7371	Intermediate Similarity	NPC202605
0.7371	Intermediate Similarity	NPC112206
0.7368	Intermediate Similarity	NPC470500
0.7368	Intermediate Similarity	NPC177404
0.7366	Intermediate Similarity	NPC224928
0.736	Intermediate Similarity	NPC271792
0.7358	Intermediate Similarity	NPC5145
0.7356	Intermediate Similarity	NPC126481
0.7354	Intermediate Similarity	NPC328596
0.7354	Intermediate Similarity	NPC328318
0.7337	Intermediate Similarity	NPC56170
0.7326	Intermediate Similarity	NPC102423
0.731	Intermediate Similarity	NPC469727
0.7303	Intermediate Similarity	NPC72980
0.7299	Intermediate Similarity	NPC278874
0.7294	Intermediate Similarity	NPC129721
0.7278	Intermediate Similarity	NPC63562
0.7273	Intermediate Similarity	NPC86288
0.7267	Intermediate Similarity	NPC224632
0.7262	Intermediate Similarity	NPC153769
0.7251	Intermediate Similarity	NPC113812
0.7243	Intermediate Similarity	NPC133140
0.7243	Intermediate Similarity	NPC195268
0.724	Intermediate Similarity	NPC476124
0.724	Intermediate Similarity	NPC476121
0.724	Intermediate Similarity	NPC317373
0.7222	Intermediate Similarity	NPC477891
0.7222	Intermediate Similarity	NPC304926
0.7222	Intermediate Similarity	NPC476041
0.7222	Intermediate Similarity	NPC144114
0.7219	Intermediate Similarity	NPC143603
0.7216	Intermediate Similarity	NPC476686
0.7216	Intermediate Similarity	NPC105758
0.7216	Intermediate Similarity	NPC476688
0.7215	Intermediate Similarity	NPC69914
0.7211	Intermediate Similarity	NPC232727
0.7209	Intermediate Similarity	NPC322976
0.7209	Intermediate Similarity	NPC324203
0.7209	Intermediate Similarity	NPC63338
0.7193	Intermediate Similarity	NPC132680
0.7193	Intermediate Similarity	NPC269919
0.7192	Intermediate Similarity	NPC132631
0.7192	Intermediate Similarity	NPC103687
0.7192	Intermediate Similarity	NPC214980
0.7191	Intermediate Similarity	NPC288943
0.7188	Intermediate Similarity	NPC118832
0.7188	Intermediate Similarity	NPC36229
0.7188	Intermediate Similarity	NPC329708
0.7188	Intermediate Similarity	NPC165349
0.7188	Intermediate Similarity	NPC47059
0.7188	Intermediate Similarity	NPC285558
0.7188	Intermediate Similarity	NPC476581
0.7188	Intermediate Similarity	NPC327592
0.7188	Intermediate Similarity	NPC16452
0.7188	Intermediate Similarity	NPC264166
0.7188	Intermediate Similarity	NPC274291
0.7186	Intermediate Similarity	NPC173080
0.7181	Intermediate Similarity	NPC156704
0.7179	Intermediate Similarity	NPC309845
0.7179	Intermediate Similarity	NPC167860
0.7179	Intermediate Similarity	NPC123976
0.7178	Intermediate Similarity	NPC280853
0.7175	Intermediate Similarity	NPC474409
0.717	Intermediate Similarity	NPC174421
0.7161	Intermediate Similarity	NPC476322
0.716	Intermediate Similarity	NPC471312
0.7152	Intermediate Similarity	NPC476131
0.7143	Intermediate Similarity	NPC207851
0.7143	Intermediate Similarity	NPC212213
0.7134	Intermediate Similarity	NPC285016
0.7134	Intermediate Similarity	NPC245657
0.7134	Intermediate Similarity	NPC318935
0.7127	Intermediate Similarity	NPC219963
0.7127	Intermediate Similarity	NPC266551
0.7127	Intermediate Similarity	NPC161887
0.7119	Intermediate Similarity	NPC14651
0.7119	Intermediate Similarity	NPC158129
0.7119	Intermediate Similarity	NPC121658
0.7118	Intermediate Similarity	NPC138842
0.7117	Intermediate Similarity	NPC471596
0.7115	Intermediate Similarity	NPC245244
0.7115	Intermediate Similarity	NPC166424
0.7115	Intermediate Similarity	NPC146373
0.711	Intermediate Similarity	NPC279918
0.7107	Intermediate Similarity	NPC315320
0.7105	Intermediate Similarity	NPC476578
0.7105	Intermediate Similarity	NPC476582
0.7105	Intermediate Similarity	NPC4071
0.7102	Intermediate Similarity	NPC63751
0.7094	Intermediate Similarity	NPC130570
0.7093	Intermediate Similarity	NPC26850
0.709	Intermediate Similarity	NPC90229
0.709	Intermediate Similarity	NPC267928
0.7083	Intermediate Similarity	NPC470678
0.7081	Intermediate Similarity	NPC183805
0.7081	Intermediate Similarity	NPC32771
0.7079	Intermediate Similarity	NPC313791
0.7074	Intermediate Similarity	NPC326634
0.7072	Intermediate Similarity	NPC478032
0.7069	Intermediate Similarity	NPC282231
0.7068	Intermediate Similarity	NPC315491
0.7068	Intermediate Similarity	NPC45459
0.7068	Intermediate Similarity	NPC249040
0.7068	Intermediate Similarity	NPC176538
0.7065	Intermediate Similarity	NPC118084
0.7063	Intermediate Similarity	NPC101165
0.7062	Intermediate Similarity	NPC476518
0.7056	Intermediate Similarity	NPC283152
0.7052	Intermediate Similarity	NPC230869
0.7049	Intermediate Similarity	NPC284678
0.7047	Intermediate Similarity	NPC475774
0.7043	Intermediate Similarity	NPC3715
0.7041	Intermediate Similarity	NPC174758
0.7037	Intermediate Similarity	NPC472193
0.7031	Intermediate Similarity	NPC31930
0.7029	Intermediate Similarity	NPC263439
0.7029	Intermediate Similarity	NPC211187
0.7021	Intermediate Similarity	NPC307963
0.7021	Intermediate Similarity	NPC106937
0.7018	Intermediate Similarity	NPC26872
0.7015	Intermediate Similarity	NPC473822
0.701	Intermediate Similarity	NPC322482

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 NPC97367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	661
0.2-0.3	803
0.3-0.4	1353
0.4-0.5	3118
0.5-0.6	2005
0.6-0.7	710
0.7-0.8	85
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8688	High Similarity	NPD926	Approved
0.8688	High Similarity	NPD925	Approved
0.8519	High Similarity	NPD424	Approved
0.8519	High Similarity	NPD425	Approved
0.8442	Intermediate Similarity	NPD3813	Approved
0.8013	Intermediate Similarity	NPD1649	Discontinued
0.8012	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5255	Approved
0.7953	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD9284	Approved
0.7919	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD9080	Approved
0.7811	Intermediate Similarity	NPD2781	Approved
0.7798	Intermediate Similarity	NPD2780	Approved
0.7798	Intermediate Similarity	NPD2782	Approved
0.774	Intermediate Similarity	NPD4375	Approved
0.7737	Intermediate Similarity	NPD3330	Phase 1
0.7722	Intermediate Similarity	NPD6569	Phase 2
0.7706	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5100	Phase 3
0.7683	Intermediate Similarity	NPD3262	Approved
0.7654	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD1032	Phase 2
0.763	Intermediate Similarity	NPD9690	Approved
0.763	Intermediate Similarity	NPD5065	Approved
0.7607	Intermediate Similarity	NPD4702	Approved
0.7607	Intermediate Similarity	NPD4703	Approved
0.7595	Intermediate Similarity	NPD9506	Approved
0.7582	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1685	Approved
0.7574	Intermediate Similarity	NPD1684	Approved
0.7547	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD3404	Approved
0.7515	Intermediate Similarity	NPD9705	Discontinued
0.7515	Intermediate Similarity	NPD112	Approved
0.7513	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5862	Discovery
0.75	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2882	Phase 1
0.747	Intermediate Similarity	NPD6158	Phase 2
0.7459	Intermediate Similarity	NPD7948	Phase 1
0.7439	Intermediate Similarity	NPD7469	Discontinued
0.7418	Intermediate Similarity	NPD8063	Discontinued
0.7414	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4886	Phase 2
0.7407	Intermediate Similarity	NPD4044	Discontinued
0.7391	Intermediate Similarity	NPD4551	Phase 2
0.7391	Intermediate Similarity	NPD9695	Approved
0.7389	Intermediate Similarity	NPD3082	Discontinued
0.7382	Intermediate Similarity	NPD1197	Approved
0.7363	Intermediate Similarity	NPD4021	Phase 2
0.7354	Intermediate Similarity	NPD3931	Approved
0.7354	Intermediate Similarity	NPD3928	Approved
0.7351	Intermediate Similarity	NPD4998	Phase 3
0.7351	Intermediate Similarity	NPD4999	Phase 3
0.7345	Intermediate Similarity	NPD6159	Phase 2
0.734	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2896	Discontinued
0.7326	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1352	Discontinued
0.7314	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6361	Phase 2
0.7294	Intermediate Similarity	NPD2581	Approved
0.7294	Intermediate Similarity	NPD2582	Approved
0.7259	Intermediate Similarity	NPD7112	Discontinued
0.7253	Intermediate Similarity	NPD706	Phase 1
0.7251	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3921	Approved
0.7243	Intermediate Similarity	NPD3924	Approved
0.7243	Intermediate Similarity	NPD3922	Approved
0.7243	Intermediate Similarity	NPD3923	Approved
0.7228	Intermediate Similarity	NPD1213	Phase 3
0.7213	Intermediate Similarity	NPD8020	Approved
0.7213	Intermediate Similarity	NPD8021	Approved
0.7212	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2511	Approved
0.7204	Intermediate Similarity	NPD5428	Discontinued
0.7198	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4889	Approved
0.7193	Intermediate Similarity	NPD9383	Approved
0.7193	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9382	Approved
0.7188	Intermediate Similarity	NPD4122	Approved
0.7188	Intermediate Similarity	NPD32	Approved
0.7188	Intermediate Similarity	NPD4038	Approved
0.7188	Intermediate Similarity	NPD31	Approved
0.7188	Intermediate Similarity	NPD4034	Approved
0.7188	Intermediate Similarity	NPD4039	Approved
0.7188	Intermediate Similarity	NPD4036	Approved
0.7188	Intermediate Similarity	NPD4033	Approved
0.7188	Intermediate Similarity	NPD4035	Approved
0.7188	Intermediate Similarity	NPD4037	Approved
0.7184	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2720	Phase 1
0.7182	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4919	Phase 3
0.7158	Intermediate Similarity	NPD4921	Phase 3
0.7152	Intermediate Similarity	NPD3717	Discontinued
0.7135	Intermediate Similarity	NPD6026	Approved
0.7127	Intermediate Similarity	NPD3386	Phase 2
0.7126	Intermediate Similarity	NPD444	Approved
0.7126	Intermediate Similarity	NPD5925	Phase 1
0.712	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2383	Phase 1
0.7115	Intermediate Similarity	NPD2757	Phase 2
0.7107	Intermediate Similarity	NPD9207	Approved
0.7107	Intermediate Similarity	NPD9206	Approved
0.7104	Intermediate Similarity	NPD5555	Phase 1
0.7095	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1229	Phase 2
0.7081	Intermediate Similarity	NPD3944	Approved
0.7081	Intermediate Similarity	NPD3942	Approved
0.7079	Intermediate Similarity	NPD1599	Approved
0.7069	Intermediate Similarity	NPD8026	Phase 1
0.7068	Intermediate Similarity	NPD484	Approved
0.7068	Intermediate Similarity	NPD6389	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9689	Approved
0.7044	Intermediate Similarity	NPD4945	Discontinued
0.7041	Intermediate Similarity	NPD4437	Phase 3
0.7039	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3477	Phase 2
0.7035	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4204	Approved
0.7033	Intermediate Similarity	NPD4203	Approved
0.7027	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1034	Phase 3
0.7025	Intermediate Similarity	NPD991	Phase 2
0.7025	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2119	Approved
0.7025	Intermediate Similarity	NPD2118	Approved
0.7022	Intermediate Similarity	NPD2123	Phase 3
0.7021	Intermediate Similarity	NPD802	Phase 2
0.7021	Intermediate Similarity	NPD1038	Approved
0.7011	Intermediate Similarity	NPD6227	Discontinued
0.7011	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2952	Discontinued
0.7	Intermediate Similarity	NPD7021	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2380	Approved
0.7	Intermediate Similarity	NPD2381	Approved
0.7	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2382	Approved
0.6995	Remote Similarity	NPD6132	Phase 1
0.6995	Remote Similarity	NPD6975	Discontinued
0.699	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1912	Approved
0.6984	Remote Similarity	NPD3396	Approved
0.6984	Remote Similarity	NPD3395	Approved
0.6982	Remote Similarity	NPD4547	Phase 3
0.6978	Remote Similarity	NPD2599	Approved
0.6978	Remote Similarity	NPD2600	Approved
0.6978	Remote Similarity	NPD2601	Approved
0.6964	Remote Similarity	NPD9074	Approved
0.6964	Remote Similarity	NPD9075	Approved
0.6959	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3321	Discontinued
0.6952	Remote Similarity	NPD6281	Approved
0.6947	Remote Similarity	NPD2482	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6492	Phase 2
0.694	Remote Similarity	NPD8408	Discontinued
0.694	Remote Similarity	NPD1570	Approved
0.6935	Remote Similarity	NPD3816	Phase 1
0.6935	Remote Similarity	NPD3815	Phase 1
0.6932	Remote Similarity	NPD5088	Discontinued
0.6931	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4795	Phase 2
0.6919	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1598	Discontinued
0.6909	Remote Similarity	NPD852	Discontinued
0.6907	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2751	Phase 1
0.6905	Remote Similarity	NPD8823	Approved
0.6897	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD715	Phase 3
0.6891	Remote Similarity	NPD1740	Approved
0.6891	Remote Similarity	NPD1739	Approved
0.6891	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7758	Approved
0.6882	Remote Similarity	NPD7757	Approved
0.6882	Remote Similarity	NPD1661	Suspended
0.6878	Remote Similarity	NPD2127	Suspended
0.6878	Remote Similarity	NPD4615	Phase 2
0.6878	Remote Similarity	NPD4372	Phase 1
0.6878	Remote Similarity	NPD5505	Discontinued
0.6875	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1326	Approved
0.6872	Remote Similarity	NPD1325	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