NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	239.09
Volume:	252.449
LogP:	3.94
LogD:	2.71
LogS:	-3.624
# Rotatable Bonds:	0
TPSA:	53.35
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	3.035
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.997
MDCK Permeability:	6.038785159034887e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.44
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	95.96920013427734%
Volume Distribution (VD):	0.676
Pgp-substrate:	4.343654632568359%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.243
CYP2C19-substrate:	0.131
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.651
CYP2D6-inhibitor:	0.417
CYP2D6-substrate:	0.652
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	4.764
Half-life (T1/2):	0.449

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.788
Rat Oral Acute Toxicity:	0.751
Maximum Recommended Daily Dose:	0.644
Skin Sensitization:	0.903
Carcinogencity:	0.812
Eye Corrosion:	0.023
Eye Irritation:	0.925
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC139763

Natural Product ID:	NPC139763
*Common Name:**	GSWNGVOZZZCECM-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GSWNGVOZZZCECM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13NO2/c1-7-4-5-10-8(2)6-16-13-9(3)14(17)15(18)11(7)12(10)13/h4-6,17H,1-3H3
SMILES:	Cc1ccc2c(C)cnc3C(=C(C(=O)c1c23)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386323
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines 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
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23734721]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15986	Alangium chinense	Species	Cornaceae	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
IC50	2

Activity Type	# Activity
Organism	1
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	3900.0	nM	PMID[461235]
NPT3494	Organism	Coxsackievirus	Coxsackievirus	IC50	>	20000.0	nM	PMID[461235]

☑ 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 NPC139763 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	302
0.1-0.2	2054
0.2-0.3	9787
0.3-0.4	13185
0.4-0.5	12627
0.5-0.6	2815
0.6-0.7	1753
0.7-0.8	172
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8161	Intermediate Similarity	NPC471997
0.7933	Intermediate Similarity	NPC118084
0.7914	Intermediate Similarity	NPC328318
0.7914	Intermediate Similarity	NPC328596
0.7803	Intermediate Similarity	NPC70949
0.7802	Intermediate Similarity	NPC154339
0.7789	Intermediate Similarity	NPC317373
0.7772	Intermediate Similarity	NPC267343
0.7742	Intermediate Similarity	NPC227582
0.774	Intermediate Similarity	NPC157583
0.7737	Intermediate Similarity	NPC327592
0.7722	Intermediate Similarity	NPC207851
0.772	Intermediate Similarity	NPC470020
0.7661	Intermediate Similarity	NPC80681
0.763	Intermediate Similarity	NPC265100
0.7619	Intermediate Similarity	NPC252338
0.7598	Intermediate Similarity	NPC55772
0.7598	Intermediate Similarity	NPC164340
0.7553	Intermediate Similarity	NPC106824
0.7543	Intermediate Similarity	NPC41717
0.7542	Intermediate Similarity	NPC237188
0.7513	Intermediate Similarity	NPC472065
0.7513	Intermediate Similarity	NPC317752
0.7474	Intermediate Similarity	NPC284338
0.7473	Intermediate Similarity	NPC114974
0.7471	Intermediate Similarity	NPC70406
0.7462	Intermediate Similarity	NPC318299
0.7459	Intermediate Similarity	NPC44354
0.7447	Intermediate Similarity	NPC146724
0.7444	Intermediate Similarity	NPC111275
0.7423	Intermediate Similarity	NPC472064
0.7405	Intermediate Similarity	NPC206186
0.7403	Intermediate Similarity	NPC248462
0.7389	Intermediate Similarity	NPC84347
0.7387	Intermediate Similarity	NPC237740
0.7382	Intermediate Similarity	NPC74413
0.7382	Intermediate Similarity	NPC81535
0.7374	Intermediate Similarity	NPC477976
0.7368	Intermediate Similarity	NPC217021
0.7368	Intermediate Similarity	NPC90229
0.7368	Intermediate Similarity	NPC470679
0.7366	Intermediate Similarity	NPC255909
0.7358	Intermediate Similarity	NPC472063
0.7358	Intermediate Similarity	NPC260900
0.7358	Intermediate Similarity	NPC472062
0.7358	Intermediate Similarity	NPC57398
0.7358	Intermediate Similarity	NPC472069
0.7351	Intermediate Similarity	NPC315555
0.734	Intermediate Similarity	NPC47190
0.734	Intermediate Similarity	NPC56170
0.7326	Intermediate Similarity	NPC83111
0.7316	Intermediate Similarity	NPC11445
0.7316	Intermediate Similarity	NPC109922
0.7303	Intermediate Similarity	NPC78020
0.7273	Intermediate Similarity	NPC183805
0.7268	Intermediate Similarity	NPC73994
0.7263	Intermediate Similarity	NPC157828
0.7263	Intermediate Similarity	NPC195239
0.7253	Intermediate Similarity	NPC64436
0.724	Intermediate Similarity	NPC149708
0.7225	Intermediate Similarity	NPC251391
0.722	Intermediate Similarity	NPC210434
0.7213	Intermediate Similarity	NPC213468
0.7209	Intermediate Similarity	NPC473878
0.7209	Intermediate Similarity	NPC313889
0.7208	Intermediate Similarity	NPC193238
0.72	Intermediate Similarity	NPC219087
0.72	Intermediate Similarity	NPC129721
0.7198	Intermediate Similarity	NPC470018
0.7198	Intermediate Similarity	NPC267885
0.7196	Intermediate Similarity	NPC473763
0.7196	Intermediate Similarity	NPC117244
0.7194	Intermediate Similarity	NPC477043
0.7189	Intermediate Similarity	NPC159125
0.7186	Intermediate Similarity	NPC309845
0.7184	Intermediate Similarity	NPC322482
0.7175	Intermediate Similarity	NPC242116
0.7174	Intermediate Similarity	NPC15840
0.7172	Intermediate Similarity	NPC258062
0.7166	Intermediate Similarity	NPC62749
0.7164	Intermediate Similarity	NPC236668
0.7163	Intermediate Similarity	NPC74575
0.7157	Intermediate Similarity	NPC175602
0.7151	Intermediate Similarity	NPC123906
0.7151	Intermediate Similarity	NPC46895
0.715	Intermediate Similarity	NPC476818
0.715	Intermediate Similarity	NPC474916
0.7143	Intermediate Similarity	NPC95783
0.7143	Intermediate Similarity	NPC149155
0.7143	Intermediate Similarity	NPC303225
0.7143	Intermediate Similarity	NPC203468
0.7143	Intermediate Similarity	NPC110500
0.7136	Intermediate Similarity	NPC472070
0.7136	Intermediate Similarity	NPC61038
0.7135	Intermediate Similarity	NPC194640
0.7134	Intermediate Similarity	NPC322488
0.7129	Intermediate Similarity	NPC146976
0.7128	Intermediate Similarity	NPC278434
0.7121	Intermediate Similarity	NPC225821
0.712	Intermediate Similarity	NPC103230
0.712	Intermediate Similarity	NPC248041
0.712	Intermediate Similarity	NPC126709
0.712	Intermediate Similarity	NPC45850
0.7119	Intermediate Similarity	NPC100104
0.7119	Intermediate Similarity	NPC470680
0.7114	Intermediate Similarity	NPC87856
0.7113	Intermediate Similarity	NPC123395
0.7112	Intermediate Similarity	NPC282103
0.7095	Intermediate Similarity	NPC71132
0.7094	Intermediate Similarity	NPC132211
0.709	Intermediate Similarity	NPC103119
0.7081	Intermediate Similarity	NPC61011
0.7062	Intermediate Similarity	NPC477044
0.7062	Intermediate Similarity	NPC131887
0.7062	Intermediate Similarity	NPC474492
0.7062	Intermediate Similarity	NPC477041
0.7056	Intermediate Similarity	NPC114637
0.7056	Intermediate Similarity	NPC98715
0.705	Intermediate Similarity	NPC271862
0.7033	Intermediate Similarity	NPC249614
0.703	Intermediate Similarity	NPC110182
0.7028	Intermediate Similarity	NPC49547
0.7027	Intermediate Similarity	NPC283219
0.7022	Intermediate Similarity	NPC322644
0.7021	Intermediate Similarity	NPC295158
0.7014	Intermediate Similarity	NPC24019
0.701	Intermediate Similarity	NPC473814
0.701	Intermediate Similarity	NPC203614
0.701	Intermediate Similarity	NPC78767
0.7005	Intermediate Similarity	NPC476073
0.7005	Intermediate Similarity	NPC469358
0.7	Intermediate Similarity	NPC127677
0.6995	Remote Similarity	NPC202812
0.6995	Remote Similarity	NPC93390
0.6995	Remote Similarity	NPC207866
0.6995	Remote Similarity	NPC135950
0.6994	Remote Similarity	NPC105811
0.699	Remote Similarity	NPC213308
0.6989	Remote Similarity	NPC271792
0.6989	Remote Similarity	NPC325705
0.6989	Remote Similarity	NPC52831
0.6989	Remote Similarity	NPC209362
0.6984	Remote Similarity	NPC194040
0.6984	Remote Similarity	NPC235684
0.6983	Remote Similarity	NPC282231
0.6979	Remote Similarity	NPC67551
0.6979	Remote Similarity	NPC216550
0.6977	Remote Similarity	NPC467188
0.6974	Remote Similarity	NPC212213
0.6973	Remote Similarity	NPC83774
0.6973	Remote Similarity	NPC151939
0.6971	Remote Similarity	NPC216612
0.6968	Remote Similarity	NPC258480
0.6966	Remote Similarity	NPC230869
0.6957	Remote Similarity	NPC293216
0.6954	Remote Similarity	NPC300183
0.6952	Remote Similarity	NPC113626
0.6952	Remote Similarity	NPC191415
0.6952	Remote Similarity	NPC71037
0.695	Remote Similarity	NPC183777
0.695	Remote Similarity	NPC46225
0.6948	Remote Similarity	NPC233334
0.6947	Remote Similarity	NPC472323
0.6946	Remote Similarity	NPC151976
0.6944	Remote Similarity	NPC473057
0.6943	Remote Similarity	NPC473821
0.6941	Remote Similarity	NPC208522
0.6939	Remote Similarity	NPC477045
0.6939	Remote Similarity	NPC103361
0.6938	Remote Similarity	NPC229893
0.6934	Remote Similarity	NPC278525
0.693	Remote Similarity	NPC470017
0.6927	Remote Similarity	NPC138370
0.6927	Remote Similarity	NPC279918
0.6923	Remote Similarity	NPC477912
0.6923	Remote Similarity	NPC74153
0.6923	Remote Similarity	NPC169433
0.6919	Remote Similarity	NPC146824
0.6916	Remote Similarity	NPC22481
0.6915	Remote Similarity	NPC171787
0.6912	Remote Similarity	NPC267965
0.6902	Remote Similarity	NPC191310
0.6901	Remote Similarity	NPC473689
0.6901	Remote Similarity	NPC292416
0.6898	Remote Similarity	NPC470022
0.6898	Remote Similarity	NPC477042
0.6895	Remote Similarity	NPC66210
0.6895	Remote Similarity	NPC15406
0.6893	Remote Similarity	NPC469727
0.6888	Remote Similarity	NPC34837
0.6888	Remote Similarity	NPC239954
0.6887	Remote Similarity	NPC475362
0.6882	Remote Similarity	NPC145885
0.6882	Remote Similarity	NPC14113
0.6882	Remote Similarity	NPC84827
0.6881	Remote Similarity	NPC210296
0.6878	Remote Similarity	NPC165495
0.6878	Remote Similarity	NPC474412
0.6878	Remote Similarity	NPC228331
0.6878	Remote Similarity	NPC467063

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 NPC139763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	620
0.2-0.3	726
0.3-0.4	1311
0.4-0.5	3204
0.5-0.6	2243
0.6-0.7	792
0.7-0.8	49
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8022	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD6987	Phase 1
0.7784	Intermediate Similarity	NPD3238	Discontinued
0.776	Intermediate Similarity	NPD2336	Approved
0.774	Intermediate Similarity	NPD2753	Discontinued
0.7594	Intermediate Similarity	NPD2307	Discontinued
0.7588	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5100	Phase 3
0.7529	Intermediate Similarity	NPD5088	Discontinued
0.7453	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7187	Phase 2
0.7411	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6999	Discontinued
0.7333	Intermediate Similarity	NPD2896	Discontinued
0.733	Intermediate Similarity	NPD1631	Approved
0.7314	Intermediate Similarity	NPD2511	Approved
0.7308	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5901	Discontinued
0.7278	Intermediate Similarity	NPD750	Phase 2
0.7268	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5426	Phase 3
0.7193	Intermediate Similarity	NPD4703	Approved
0.7193	Intermediate Similarity	NPD1270	Approved
0.7193	Intermediate Similarity	NPD4702	Approved
0.7186	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7234	Approved
0.7181	Intermediate Similarity	NPD7233	Approved
0.7174	Intermediate Similarity	NPD2481	Approved
0.7174	Intermediate Similarity	NPD2479	Phase 3
0.7159	Intermediate Similarity	NPD1630	Approved
0.7157	Intermediate Similarity	NPD7010	Phase 3
0.7156	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6446	Discontinued
0.7143	Intermediate Similarity	NPD482	Approved
0.7143	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4948	Discontinued
0.7113	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7666	Phase 3
0.7085	Intermediate Similarity	NPD7191	Phase 2
0.7085	Intermediate Similarity	NPD7665	Phase 2
0.7072	Intermediate Similarity	NPD1573	Approved
0.7072	Intermediate Similarity	NPD1575	Approved
0.7071	Intermediate Similarity	NPD2317	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5255	Approved
0.7059	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6178	Phase 3
0.7045	Intermediate Similarity	NPD6026	Approved
0.7035	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD925	Approved
0.7	Intermediate Similarity	NPD926	Approved
0.7	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4427	Phase 2
0.6995	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2809	Approved
0.6989	Remote Similarity	NPD9510	Approved
0.6985	Remote Similarity	NPD7001	Phase 3
0.6983	Remote Similarity	NPD5400	Approved
0.6976	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3262	Approved
0.6971	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7564	Discontinued
0.6968	Remote Similarity	NPD2096	Phase 2
0.6968	Remote Similarity	NPD2091	Phase 2
0.6959	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8431	Approved
0.6931	Remote Similarity	NPD6241	Phase 1
0.6919	Remote Similarity	NPD3813	Approved
0.6915	Remote Similarity	NPD2095	Phase 2
0.6915	Remote Similarity	NPD2094	Phase 2
0.6915	Remote Similarity	NPD2092	Phase 2
0.6907	Remote Similarity	NPD7944	Discontinued
0.69	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3315	Phase 3
0.6875	Remote Similarity	NPD3321	Discontinued
0.6875	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6226	Phase 3
0.6863	Remote Similarity	NPD7069	Discontinued
0.6859	Remote Similarity	NPD6791	Phase 2
0.6853	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6635	Approved
0.6848	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1587	Approved
0.6831	Remote Similarity	NPD5862	Discovery
0.6831	Remote Similarity	NPD2781	Approved
0.6831	Remote Similarity	NPD1343	Approved
0.6829	Remote Similarity	NPD3794	Approved
0.6829	Remote Similarity	NPD3795	Approved
0.6827	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7568	Phase 1
0.6813	Remote Similarity	NPD2780	Approved
0.6813	Remote Similarity	NPD2782	Approved
0.681	Remote Similarity	NPD6995	Phase 1
0.6804	Remote Similarity	NPD4376	Phase 3
0.6794	Remote Similarity	NPD5827	Discontinued
0.6786	Remote Similarity	NPD3942	Approved
0.6786	Remote Similarity	NPD3944	Approved
0.6782	Remote Similarity	NPD9074	Approved
0.6782	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD9075	Approved
0.678	Remote Similarity	NPD2882	Phase 1
0.678	Remote Similarity	NPD8093	Discontinued
0.6774	Remote Similarity	NPD4883	Approved
0.6772	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD9362	Approved
0.6772	Remote Similarity	NPD3178	Discontinued
0.6771	Remote Similarity	NPD4988	Discontinued
0.6771	Remote Similarity	NPD9363	Approved
0.6771	Remote Similarity	NPD9364	Phase 2
0.6766	Remote Similarity	NPD3947	Discontinued
0.6766	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4051	Discontinued
0.6763	Remote Similarity	NPD3717	Discontinued
0.6755	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD2509	Approved
0.6749	Remote Similarity	NPD2510	Approved
0.6749	Remote Similarity	NPD6376	Discontinued
0.6748	Remote Similarity	NPD8094	Discontinued
0.6745	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD3925	Approved
0.6745	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4638	Approved
0.6739	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4640	Approved
0.6739	Remote Similarity	NPD4639	Approved
0.6738	Remote Similarity	NPD5471	Phase 3
0.6736	Remote Similarity	NPD7175	Phase 1
0.6734	Remote Similarity	NPD484	Approved
0.6734	Remote Similarity	NPD6479	Discontinued
0.6732	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD2119	Approved
0.6727	Remote Similarity	NPD2118	Approved
0.6725	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2582	Approved
0.6722	Remote Similarity	NPD2581	Approved
0.6719	Remote Similarity	NPD5809	Phase 3
0.6719	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5505	Discontinued
0.6718	Remote Similarity	NPD3922	Approved
0.6718	Remote Similarity	NPD3924	Approved
0.6718	Remote Similarity	NPD3923	Approved
0.6718	Remote Similarity	NPD3921	Approved
0.6717	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD4397	Phase 1
0.6716	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6242	Discontinued
0.6707	Remote Similarity	NPD3476	Approved
0.6707	Remote Similarity	NPD3475	Approved
0.6705	Remote Similarity	NPD1661	Suspended
0.6704	Remote Similarity	NPD2061	Approved
0.6703	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1684	Approved
0.6703	Remote Similarity	NPD1685	Approved
0.6702	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD721	Approved
0.6702	Remote Similarity	NPD8123	Approved
0.6702	Remote Similarity	NPD8122	Approved
0.6702	Remote Similarity	NPD1096	Discontinued
0.6701	Remote Similarity	NPD2564	Approved
0.6701	Remote Similarity	NPD6281	Approved
0.6701	Remote Similarity	NPD2565	Phase 2
0.6699	Remote Similarity	NPD4852	Phase 2
0.6698	Remote Similarity	NPD3222	Phase 2
0.6686	Remote Similarity	NPD4028	Approved
0.6686	Remote Similarity	NPD4030	Approved
0.6686	Remote Similarity	NPD4029	Approved
0.6685	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6158	Phase 2
0.6685	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5065	Approved
0.6684	Remote Similarity	NPD1586	Approved
0.6684	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3393	Approved
0.6683	Remote Similarity	NPD3394	Approved
0.6683	Remote Similarity	NPD3389	Approved
0.6682	Remote Similarity	NPD4845	Discontinued
0.6667	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3583	Phase 2
0.6667	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD200	Phase 2
0.6667	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3525	Discontinued

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