NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	350.2
Volume:	364.121
LogP:	3.037
LogD:	3.063
LogS:	-4.324
# Rotatable Bonds:	2
TPSA:	32.78
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	6.528
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.176
MDCK Permeability:	3.175739766447805e-05
Pgp-inhibitor:	0.891
Pgp-substrate:	0.233
Human Intestinal Absorption (HIA):	0.129
20% Bioavailability (F20%):	0.757
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	73.32134246826172%
Volume Distribution (VD):	2.296
Pgp-substrate:	21.2939395904541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.538
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.318
CYP2C9-substrate:	0.319
CYP2D6-inhibitor:	0.859
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.902

ADMET: Excretion

Clearance (CL):	11.853
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.796
Drug-inuced Liver Injury (DILI):	0.131
AMES Toxicity:	0.244
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.33
Carcinogencity:	0.916
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC478076

Natural Product ID:	NPC478076
*Common Name:**	methyl (1S,9S,10S,12R,13E,16R)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-17-carboxylate
IUPAC Name:	methyl (1S,9S,10S,12R,13E,16R)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-17-carboxylate
Synonyms:
Standard InCHIKey:	PRBYEVQYZLEFMG-DSVRZAJDSA-N
Standard InCHI:	InChI=1S/C22H26N2O2/c1-4-13-11-24-17-9-15(13)22(20(25)26-3)12-21(10-18(22)24)14-7-5-6-8-16(14)23(2)19(17)21/h4-8,15,17-19H,9-12H2,1-3H3/b13-4-/t15-,17+,18-,19-,21-,22?/m1/s1
SMILES:	C/C=C\1/CN2[C@H]3C[C@H]1C4([C@H]2C[C@]5(C4)[C@@H]3N(C6=CC=CC=C56)C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122179180
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002750] Corynanthean-type alkaloids

*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
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2620	nM	PMID[25919190]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25	ug/ml	PMID[25919190]

☑ 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 NPC478076 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	284
0.1-0.2	1233
0.2-0.3	4532
0.3-0.4	23452
0.4-0.5	9587
0.5-0.6	2862
0.6-0.7	567
0.7-0.8	157
0.8-0.85	11
0.85-0.9	7
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9161	High Similarity	NPC476425
0.9045	High Similarity	NPC476441
0.875	High Similarity	NPC476326
0.8589	High Similarity	NPC476428
0.8428	Intermediate Similarity	NPC472115
0.8428	Intermediate Similarity	NPC472114
0.8408	Intermediate Similarity	NPC225319
0.8354	Intermediate Similarity	NPC99632
0.8354	Intermediate Similarity	NPC282339
0.828	Intermediate Similarity	NPC113946
0.8025	Intermediate Similarity	NPC472106
0.8	Intermediate Similarity	NPC193410
0.8	Intermediate Similarity	NPC472209
0.795	Intermediate Similarity	NPC248117
0.7937	Intermediate Similarity	NPC61013
0.7901	Intermediate Similarity	NPC472101
0.7901	Intermediate Similarity	NPC472120
0.784	Intermediate Similarity	NPC474058
0.7818	Intermediate Similarity	NPC167724
0.7818	Intermediate Similarity	NPC223595
0.7818	Intermediate Similarity	NPC224970
0.7812	Intermediate Similarity	NPC161827
0.7778	Intermediate Similarity	NPC36495
0.7764	Intermediate Similarity	NPC29285
0.7758	Intermediate Similarity	NPC214960
0.7758	Intermediate Similarity	NPC279527
0.7716	Intermediate Similarity	NPC211525
0.7716	Intermediate Similarity	NPC123241
0.7716	Intermediate Similarity	NPC153694
0.7702	Intermediate Similarity	NPC473297
0.7692	Intermediate Similarity	NPC264482
0.7692	Intermediate Similarity	NPC203202
0.7683	Intermediate Similarity	NPC293458
0.7679	Intermediate Similarity	NPC139085
0.7679	Intermediate Similarity	NPC251212
0.7679	Intermediate Similarity	NPC214626
0.7674	Intermediate Similarity	NPC143533
0.7669	Intermediate Similarity	NPC243673
0.7669	Intermediate Similarity	NPC310403
0.7669	Intermediate Similarity	NPC63210
0.7669	Intermediate Similarity	NPC148468
0.7669	Intermediate Similarity	NPC97380
0.7669	Intermediate Similarity	NPC263709
0.763	Intermediate Similarity	NPC472119
0.7611	Intermediate Similarity	NPC52557
0.76	Intermediate Similarity	NPC21425
0.759	Intermediate Similarity	NPC470069
0.759	Intermediate Similarity	NPC52059
0.7586	Intermediate Similarity	NPC469460
0.7582	Intermediate Similarity	NPC471123
0.7576	Intermediate Similarity	NPC472117
0.7561	Intermediate Similarity	NPC469461
0.756	Intermediate Similarity	NPC472118
0.7515	Intermediate Similarity	NPC309531
0.7515	Intermediate Similarity	NPC472102
0.75	Intermediate Similarity	NPC6974
0.75	Intermediate Similarity	NPC218594
0.75	Intermediate Similarity	NPC469462
0.75	Intermediate Similarity	NPC99043
0.747	Intermediate Similarity	NPC176983
0.7442	Intermediate Similarity	NPC260075
0.7427	Intermediate Similarity	NPC469726
0.7427	Intermediate Similarity	NPC329338
0.7401	Intermediate Similarity	NPC181928
0.7386	Intermediate Similarity	NPC52262
0.7386	Intermediate Similarity	NPC79062
0.7386	Intermediate Similarity	NPC472107
0.7374	Intermediate Similarity	NPC472097
0.7372	Intermediate Similarity	NPC469560
0.7371	Intermediate Similarity	NPC159963
0.7368	Intermediate Similarity	NPC276993
0.7368	Intermediate Similarity	NPC181138
0.7368	Intermediate Similarity	NPC293255
0.7368	Intermediate Similarity	NPC21752
0.7368	Intermediate Similarity	NPC210415
0.7368	Intermediate Similarity	NPC285622
0.7368	Intermediate Similarity	NPC298851
0.7368	Intermediate Similarity	NPC96901
0.7348	Intermediate Similarity	NPC289299
0.7348	Intermediate Similarity	NPC57994
0.7346	Intermediate Similarity	NPC473329
0.7341	Intermediate Similarity	NPC186669
0.733	Intermediate Similarity	NPC258480
0.7318	Intermediate Similarity	NPC473298
0.7308	Intermediate Similarity	NPC245916
0.7308	Intermediate Similarity	NPC472116
0.7305	Intermediate Similarity	NPC201424
0.7303	Intermediate Similarity	NPC472323
0.7303	Intermediate Similarity	NPC14994
0.7301	Intermediate Similarity	NPC66936
0.7268	Intermediate Similarity	NPC162440
0.7262	Intermediate Similarity	NPC472121
0.7262	Intermediate Similarity	NPC286871
0.7257	Intermediate Similarity	NPC15840
0.7247	Intermediate Similarity	NPC66210
0.7246	Intermediate Similarity	NPC471122
0.7232	Intermediate Similarity	NPC97584
0.7222	Intermediate Similarity	NPC473569
0.7195	Intermediate Similarity	NPC243756
0.7182	Intermediate Similarity	NPC25401
0.7176	Intermediate Similarity	NPC475420
0.7175	Intermediate Similarity	NPC472104
0.7167	Intermediate Similarity	NPC111602
0.7167	Intermediate Similarity	NPC102338
0.7167	Intermediate Similarity	NPC175474
0.7167	Intermediate Similarity	NPC63199
0.7167	Intermediate Similarity	NPC196251
0.716	Intermediate Similarity	NPC264589
0.716	Intermediate Similarity	NPC472100
0.7158	Intermediate Similarity	NPC221687
0.7158	Intermediate Similarity	NPC34717
0.7151	Intermediate Similarity	NPC475489
0.7135	Intermediate Similarity	NPC278887
0.7127	Intermediate Similarity	NPC472112
0.7127	Intermediate Similarity	NPC22689
0.7127	Intermediate Similarity	NPC105055
0.7126	Intermediate Similarity	NPC13367
0.7117	Intermediate Similarity	NPC212799
0.7101	Intermediate Similarity	NPC81229
0.7101	Intermediate Similarity	NPC255229
0.7101	Intermediate Similarity	NPC143457
0.71	Intermediate Similarity	NPC476436
0.7081	Intermediate Similarity	NPC90967
0.7076	Intermediate Similarity	NPC471124
0.7069	Intermediate Similarity	NPC473743
0.7069	Intermediate Similarity	NPC473880
0.7059	Intermediate Similarity	NPC194881
0.7056	Intermediate Similarity	NPC478077
0.7049	Intermediate Similarity	NPC472113
0.7047	Intermediate Similarity	NPC82541
0.7033	Intermediate Similarity	NPC329858
0.7033	Intermediate Similarity	NPC314333
0.7	Intermediate Similarity	NPC130251
0.6988	Remote Similarity	NPC475763
0.6988	Remote Similarity	NPC154602
0.6982	Remote Similarity	NPC222029
0.6982	Remote Similarity	NPC104345
0.6968	Remote Similarity	NPC313985
0.6968	Remote Similarity	NPC128265
0.6968	Remote Similarity	NPC249150
0.6968	Remote Similarity	NPC294909
0.6968	Remote Similarity	NPC49196
0.6968	Remote Similarity	NPC195461
0.6968	Remote Similarity	NPC79129
0.6968	Remote Similarity	NPC81654
0.6968	Remote Similarity	NPC312870
0.6968	Remote Similarity	NPC254240
0.6968	Remote Similarity	NPC199851
0.6966	Remote Similarity	NPC11149
0.6966	Remote Similarity	NPC469896
0.6959	Remote Similarity	NPC85651
0.6959	Remote Similarity	NPC469741
0.6957	Remote Similarity	NPC470301
0.6949	Remote Similarity	NPC234987
0.6946	Remote Similarity	NPC122106
0.6935	Remote Similarity	NPC473375
0.6935	Remote Similarity	NPC97100
0.6931	Remote Similarity	NPC471512
0.6927	Remote Similarity	NPC475962
0.6927	Remote Similarity	NPC476429
0.6919	Remote Similarity	NPC313757
0.6911	Remote Similarity	NPC329833
0.691	Remote Similarity	NPC321211
0.6902	Remote Similarity	NPC203628
0.6902	Remote Similarity	NPC22476
0.6894	Remote Similarity	NPC315051
0.6894	Remote Similarity	NPC243162
0.6889	Remote Similarity	NPC477159
0.6887	Remote Similarity	NPC475915
0.6878	Remote Similarity	NPC67904
0.6878	Remote Similarity	NPC138830
0.6862	Remote Similarity	NPC50503
0.6857	Remote Similarity	NPC469915
0.6852	Remote Similarity	NPC186284
0.6852	Remote Similarity	NPC22082
0.6848	Remote Similarity	NPC5630
0.6829	Remote Similarity	NPC311330
0.6824	Remote Similarity	NPC469536
0.6818	Remote Similarity	NPC318183
0.6816	Remote Similarity	NPC133261
0.6813	Remote Similarity	NPC259626
0.6809	Remote Similarity	NPC475559
0.6806	Remote Similarity	NPC137589
0.6806	Remote Similarity	NPC162730
0.6802	Remote Similarity	NPC68650
0.6802	Remote Similarity	NPC315368
0.6798	Remote Similarity	NPC24594
0.6798	Remote Similarity	NPC472122
0.6791	Remote Similarity	NPC220151
0.6791	Remote Similarity	NPC19692
0.6788	Remote Similarity	NPC116519
0.678	Remote Similarity	NPC472123
0.678	Remote Similarity	NPC177261
0.6778	Remote Similarity	NPC187827
0.6778	Remote Similarity	NPC472105
0.6776	Remote Similarity	NPC282092
0.6774	Remote Similarity	NPC55493
0.6772	Remote Similarity	NPC100863
0.6772	Remote Similarity	NPC218733
0.6772	Remote Similarity	NPC138615

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 NPC478076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	531
0.2-0.3	792
0.3-0.4	1764
0.4-0.5	3795
0.5-0.6	1875
0.6-0.7	213
0.7-0.8	6
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD4121	Phase 3
0.8205	Intermediate Similarity	NPD4120	Approved
0.8153	Intermediate Similarity	NPD5743	Approved
0.8153	Intermediate Similarity	NPD5742	Approved
0.8153	Intermediate Similarity	NPD5741	Approved
0.7379	Intermediate Similarity	NPD2994	Approved
0.7348	Intermediate Similarity	NPD4602	Approved
0.731	Intermediate Similarity	NPD2117	Pre-registration
0.731	Intermediate Similarity	NPD2116	Approved
0.731	Intermediate Similarity	NPD2115	Approved
0.7297	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2946	Phase 2
0.7211	Intermediate Similarity	NPD3030	Approved
0.7211	Intermediate Similarity	NPD3032	Approved
0.7211	Intermediate Similarity	NPD3031	Approved
0.7178	Intermediate Similarity	NPD4682	Phase 2
0.7143	Intermediate Similarity	NPD7487	Discontinued
0.7143	Intermediate Similarity	NPD7599	Phase 2
0.7115	Intermediate Similarity	NPD5185	Approved
0.7115	Intermediate Similarity	NPD5184	Approved
0.7115	Intermediate Similarity	NPD5182	Approved
0.7101	Intermediate Similarity	NPD7600	Phase 2
0.7099	Intermediate Similarity	NPD5932	Phase 3
0.7099	Intermediate Similarity	NPD5931	Phase 3
0.7099	Intermediate Similarity	NPD5933	Phase 3
0.7063	Intermediate Similarity	NPD3625	Discontinued
0.7033	Intermediate Similarity	NPD4499	Approved
0.7012	Intermediate Similarity	NPD7478	Approved
0.6988	Remote Similarity	NPD7606	Phase 3
0.6968	Remote Similarity	NPD4600	Approved
0.6968	Remote Similarity	NPD4601	Approved
0.6968	Remote Similarity	NPD4501	Approved
0.6968	Remote Similarity	NPD4500	Approved
0.6882	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5629	Discontinued
0.6867	Remote Similarity	NPD5942	Approved
0.6867	Remote Similarity	NPD5941	Approved
0.6856	Remote Similarity	NPD4520	Approved
0.6825	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6566	Discontinued
0.6806	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2506	Approved
0.6788	Remote Similarity	NPD7295	Approved
0.678	Remote Similarity	NPD3377	Discontinued
0.677	Remote Similarity	NPD2670	Approved
0.6768	Remote Similarity	NPD5024	Approved
0.6768	Remote Similarity	NPD7082	Approved
0.6768	Remote Similarity	NPD2820	Phase 3
0.6761	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6416	Phase 2
0.6742	Remote Similarity	NPD3422	Phase 3
0.6742	Remote Similarity	NPD3423	Phase 2
0.6731	Remote Similarity	NPD5993	Phase 1
0.673	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5918	Discontinued
0.6727	Remote Similarity	NPD7259	Approved
0.6723	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2365	Approved
0.6688	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1360	Approved
0.6688	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4329	Approved
0.6685	Remote Similarity	NPD4330	Approved
0.6667	Remote Similarity	NPD6070	Approved
0.6667	Remote Similarity	NPD6358	Phase 2
0.6667	Remote Similarity	NPD6069	Approved
0.6649	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2427	Approved
0.6644	Remote Similarity	NPD4116	Approved
0.6632	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7734	Approved
0.6625	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2607	Approved
0.661	Remote Similarity	NPD2037	Approved
0.6609	Remote Similarity	NPD7275	Approved
0.6605	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5997	Discontinued
0.659	Remote Similarity	NPD8630	Approved
0.6587	Remote Similarity	NPD6017	Discontinued
0.6577	Remote Similarity	NPD5181	Approved
0.6577	Remote Similarity	NPD2914	Approved
0.6577	Remote Similarity	NPD2913	Approved
0.6577	Remote Similarity	NPD5179	Approved
0.6577	Remote Similarity	NPD5180	Approved
0.6575	Remote Similarity	NPD3792	Approved
0.6557	Remote Similarity	NPD3470	Approved
0.6557	Remote Similarity	NPD3471	Approved
0.6552	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5504	Discontinued
0.6541	Remote Similarity	NPD4676	Approved
0.6536	Remote Similarity	NPD2431	Approved
0.6536	Remote Similarity	NPD2432	Approved
0.6534	Remote Similarity	NPD3790	Phase 2
0.6524	Remote Similarity	NPD3170	Approved
0.6522	Remote Similarity	NPD1527	Phase 2
0.6519	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD2455	Approved
0.6517	Remote Similarity	NPD2454	Approved
0.6516	Remote Similarity	NPD4178	Approved
0.6516	Remote Similarity	NPD4176	Approved
0.6509	Remote Similarity	NPD1802	Approved
0.6509	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1801	Approved
0.6503	Remote Similarity	NPD5725	Approved
0.65	Remote Similarity	NPD1069	Approved
0.65	Remote Similarity	NPD1070	Approved
0.65	Remote Similarity	NPD6489	Phase 3
0.6497	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7795	Phase 2
0.6471	Remote Similarity	NPD4432	Discontinued
0.6471	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1373	Approved
0.6467	Remote Similarity	NPD1374	Approved
0.6467	Remote Similarity	NPD1371	Approved
0.6467	Remote Similarity	NPD1370	Approved
0.6457	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD3782	Discontinued
0.6443	Remote Similarity	NPD6805	Discontinued
0.6441	Remote Similarity	NPD8270	Approved
0.6438	Remote Similarity	NPD4365	Phase 2
0.6438	Remote Similarity	NPD5263	Approved
0.6436	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5104	Approved
0.6429	Remote Similarity	NPD2435	Approved
0.6425	Remote Similarity	NPD2404	Discontinued
0.6425	Remote Similarity	NPD4397	Phase 1
0.6424	Remote Similarity	NPD4766	Approved
0.6424	Remote Similarity	NPD3551	Approved
0.6419	Remote Similarity	NPD7633	Discontinued
0.641	Remote Similarity	NPD2608	Approved
0.641	Remote Similarity	NPD3131	Approved
0.641	Remote Similarity	NPD2611	Approved
0.641	Remote Similarity	NPD2612	Approved
0.641	Remote Similarity	NPD2610	Approved
0.641	Remote Similarity	NPD4218	Approved
0.641	Remote Similarity	NPD2609	Approved
0.641	Remote Similarity	NPD4217	Approved
0.641	Remote Similarity	NPD4216	Approved
0.641	Remote Similarity	NPD3132	Approved
0.641	Remote Similarity	NPD4215	Approved
0.6409	Remote Similarity	NPD7854	Phase 2
0.6404	Remote Similarity	NPD5430	Discontinued
0.6402	Remote Similarity	NPD6073	Approved
0.6392	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5578	Approved
0.639	Remote Similarity	NPD7168	Phase 3
0.6386	Remote Similarity	NPD989	Approved
0.6375	Remote Similarity	NPD4549	Discontinued
0.6374	Remote Similarity	NPD7528	Approved
0.6369	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2569	Approved
0.6364	Remote Similarity	NPD2567	Approved
0.6358	Remote Similarity	NPD8400	Approved
0.6358	Remote Similarity	NPD8401	Approved
0.6358	Remote Similarity	NPD8402	Approved
0.6358	Remote Similarity	NPD2948	Discontinued
0.6353	Remote Similarity	NPD4041	Approved
0.6344	Remote Similarity	NPD7962	Phase 2
0.6344	Remote Similarity	NPD8281	Discontinued
0.6343	Remote Similarity	NPD1663	Discontinued
0.6339	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5748	Phase 2
0.6335	Remote Similarity	NPD5131	Approved
0.6333	Remote Similarity	NPD7126	Discontinued
0.6333	Remote Similarity	NPD6457	Approved
0.6333	Remote Similarity	NPD2844	Phase 3
0.6329	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3549	Approved
0.6329	Remote Similarity	NPD3547	Approved
0.6328	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5989	Phase 1
0.6324	Remote Similarity	NPD6878	Phase 2
0.6324	Remote Similarity	NPD6879	Phase 2
0.6319	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD750	Phase 2
0.631	Remote Similarity	NPD6768	Approved
0.6309	Remote Similarity	NPD1752	Approved
0.6309	Remote Similarity	NPD1756	Approved
0.6307	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5600	Discontinued
0.6301	Remote Similarity	NPD5982	Phase 2
0.6289	Remote Similarity	NPD3828	Approved
0.6289	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5253	Approved
0.6284	Remote Similarity	NPD7940	Phase 3
0.6283	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD8240	Discontinued
0.6272	Remote Similarity	NPD6301	Phase 2
0.6265	Remote Similarity	NPD6342	Discontinued
0.6265	Remote Similarity	NPD6294	Approved
0.6265	Remote Similarity	NPD6295	Approved
0.6263	Remote Similarity	NPD7205	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