NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	290.14
Volume:	300.806
LogP:	2.211
LogD:	2.541
LogS:	-4.854
# Rotatable Bonds:	1
TPSA:	33.95
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	6.872
Fsp3:	0.474
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:	-4.898
MDCK Permeability:	3.061103416257538e-05
Pgp-inhibitor:	0.1
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.771
Plasma Protein Binding (PPB):	85.50306701660156%
Volume Distribution (VD):	1.839
Pgp-substrate:	11.673356056213379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.143
CYP1A2-substrate:	0.744
CYP2C19-inhibitor:	0.405
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.403
CYP2C9-substrate:	0.618
CYP2D6-inhibitor:	0.398
CYP2D6-substrate:	0.578
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.866

ADMET: Excretion

Clearance (CL):	1.78
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.846
Human Hepatotoxicity (H-HT):	0.461
Drug-inuced Liver Injury (DILI):	0.387
AMES Toxicity:	0.292
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.352
Carcinogencity:	0.482
Eye Corrosion:	0.004
Eye Irritation:	0.313
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC477155

Natural Product ID:	NPC477155
*Common Name:**	(10R,16R,17S)-15-ethenyl-19-oxa-3,13-diazahexacyclo[14.3.1.02,10.04,9.010,15.012,17]icosa-2,4,6,8,13-pentaene
IUPAC Name:	(10R,16R,17S)-15-ethenyl-19-oxa-3,13-diazahexacyclo[14.3.1.02,10.04,9.010,15.012,17]icosa-2,4,6,8,13-pentaene
Synonyms:
Standard InCHIKey:	URHXGSWFPKWUHZ-LAPVKLKXSA-N
Standard InCHI:	InChI=1S/C19H18N2O/c1-2-18-10-20-15-8-19(18)12-5-3-4-6-14(12)21-17(19)16-7-13(18)11(15)9-22-16/h2-6,10-11,13,15-16H,1,7-9H2/t11-,13+,15?,16?,18?,19-/m0/s1
SMILES:	C=CC12C=NC3C[C@@]14C5=CC=CC=C5N=C4C6C[C@@H]2[C@@H]3CO6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	162818890
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643063]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989532]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256496]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	leaves and vine stems	Xishuangbanna Tropical Botanical Garden (XTBG), Chinese Academy of Science (CAS), Mengla County, Yunnan Province, China	2009-OCT	PMID[26103517]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222693]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	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	7

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4600	nM	PMID[26103517]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	5300	nM	PMID[26103517]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4900	nM	PMID[26103517]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9300	nM	PMID[26103517]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	7300	nM	PMID[26103517]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000	nM	PMID[26103517]
NPT2	Others	Unspecified		IC50	=	8600	nM	PMID[26103517]

☑ 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 NPC477155 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	376
0.1-0.2	1593
0.2-0.3	6664
0.3-0.4	22335
0.4-0.5	9276
0.5-0.6	2224
0.6-0.7	216
0.7-0.8	8
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8936	High Similarity	NPC116519
0.84	Intermediate Similarity	NPC477157
0.84	Intermediate Similarity	NPC477156
0.8	Intermediate Similarity	NPC477158
0.7945	Intermediate Similarity	NPC243162
0.7296	Intermediate Similarity	NPC473297
0.7192	Intermediate Similarity	NPC478079
0.7179	Intermediate Similarity	NPC472100
0.7051	Intermediate Similarity	NPC472103
0.7042	Intermediate Similarity	NPC264580
0.6951	Remote Similarity	NPC469461
0.6939	Remote Similarity	NPC325013
0.6909	Remote Similarity	NPC143457
0.6905	Remote Similarity	NPC469462
0.6902	Remote Similarity	NPC52801
0.6855	Remote Similarity	NPC264589
0.6813	Remote Similarity	NPC469740
0.68	Remote Similarity	NPC259098
0.68	Remote Similarity	NPC197680
0.6761	Remote Similarity	NPC470550
0.6761	Remote Similarity	NPC205652
0.6746	Remote Similarity	NPC278887
0.6686	Remote Similarity	NPC475420
0.6667	Remote Similarity	NPC472121
0.6646	Remote Similarity	NPC470579
0.6646	Remote Similarity	NPC469735
0.6625	Remote Similarity	NPC311330
0.661	Remote Similarity	NPC19679
0.659	Remote Similarity	NPC139085
0.659	Remote Similarity	NPC473743
0.659	Remote Similarity	NPC214626
0.659	Remote Similarity	NPC251212
0.657	Remote Similarity	NPC257354
0.6566	Remote Similarity	NPC114808
0.6566	Remote Similarity	NPC161827
0.6552	Remote Similarity	NPC13367
0.6536	Remote Similarity	NPC52262
0.6532	Remote Similarity	NPC126492
0.6509	Remote Similarity	NPC225319
0.6507	Remote Similarity	NPC192209
0.6503	Remote Similarity	NPC212799
0.6494	Remote Similarity	NPC21752
0.6494	Remote Similarity	NPC473880
0.6494	Remote Similarity	NPC181138
0.6494	Remote Similarity	NPC298851
0.6494	Remote Similarity	NPC210415
0.6494	Remote Similarity	NPC293255
0.6494	Remote Similarity	NPC276993
0.6488	Remote Similarity	NPC211525
0.6488	Remote Similarity	NPC153694
0.6485	Remote Similarity	NPC475763
0.6474	Remote Similarity	NPC90693
0.6474	Remote Similarity	NPC64897
0.6471	Remote Similarity	NPC282339
0.6471	Remote Similarity	NPC99632
0.6471	Remote Similarity	NPC295478
0.6461	Remote Similarity	NPC475962
0.6458	Remote Similarity	NPC187036
0.6457	Remote Similarity	NPC475097
0.645	Remote Similarity	NPC148468
0.645	Remote Similarity	NPC310403
0.645	Remote Similarity	NPC63210
0.645	Remote Similarity	NPC263709
0.645	Remote Similarity	NPC97380
0.645	Remote Similarity	NPC243673
0.6449	Remote Similarity	NPC178681
0.6447	Remote Similarity	NPC278097
0.6433	Remote Similarity	NPC469541
0.642	Remote Similarity	NPC320147
0.6416	Remote Similarity	NPC154293
0.6395	Remote Similarity	NPC470069
0.6395	Remote Similarity	NPC52059
0.6393	Remote Similarity	NPC95783
0.6389	Remote Similarity	NPC245741
0.6386	Remote Similarity	NPC206592
0.6382	Remote Similarity	NPC474926
0.6369	Remote Similarity	NPC184437
0.6358	Remote Similarity	NPC19555
0.6354	Remote Similarity	NPC476095
0.6353	Remote Similarity	NPC291359
0.6346	Remote Similarity	NPC42423
0.6331	Remote Similarity	NPC29285
0.6328	Remote Similarity	NPC472122
0.6328	Remote Similarity	NPC24594
0.6327	Remote Similarity	NPC147957
0.6323	Remote Similarity	NPC9856
0.6319	Remote Similarity	NPC282092
0.6316	Remote Similarity	NPC255229
0.6316	Remote Similarity	NPC81229
0.6313	Remote Similarity	NPC472105
0.6313	Remote Similarity	NPC300688
0.6313	Remote Similarity	NPC187827
0.6308	Remote Similarity	NPC126066
0.6307	Remote Similarity	NPC96901
0.6304	Remote Similarity	NPC105055
0.6304	Remote Similarity	NPC22689
0.6294	Remote Similarity	NPC104345
0.6294	Remote Similarity	NPC475602
0.6292	Remote Similarity	NPC326575
0.6292	Remote Similarity	NPC151939
0.6292	Remote Similarity	NPC260075
0.6284	Remote Similarity	NPC285841
0.6284	Remote Similarity	NPC313449
0.6282	Remote Similarity	NPC316746
0.6273	Remote Similarity	NPC239770
0.6271	Remote Similarity	NPC189812
0.6271	Remote Similarity	NPC329688
0.6266	Remote Similarity	NPC132847
0.6264	Remote Similarity	NPC469460
0.6264	Remote Similarity	NPC472209
0.6257	Remote Similarity	NPC472331
0.6257	Remote Similarity	NPC274002
0.6257	Remote Similarity	NPC126515
0.625	Remote Similarity	NPC328683
0.625	Remote Similarity	NPC283130
0.6243	Remote Similarity	NPC472104
0.6242	Remote Similarity	NPC53044
0.6235	Remote Similarity	NPC22082
0.6235	Remote Similarity	NPC186284
0.6235	Remote Similarity	NPC51054
0.6235	Remote Similarity	NPC10875
0.6235	Remote Similarity	NPC10730
0.6233	Remote Similarity	NPC296163
0.6231	Remote Similarity	NPC251936
0.6209	Remote Similarity	NPC165201
0.6209	Remote Similarity	NPC317758
0.6207	Remote Similarity	NPC472106
0.6205	Remote Similarity	NPC87755
0.6199	Remote Similarity	NPC113946
0.6193	Remote Similarity	NPC280548
0.6193	Remote Similarity	NPC469915
0.619	Remote Similarity	NPC162440
0.619	Remote Similarity	NPC472761
0.6188	Remote Similarity	NPC175870
0.6185	Remote Similarity	NPC16667
0.6185	Remote Similarity	NPC176983
0.6185	Remote Similarity	NPC472117
0.6169	Remote Similarity	NPC472414
0.6167	Remote Similarity	NPC133261
0.6167	Remote Similarity	NPC6093
0.6164	Remote Similarity	NPC228511
0.6154	Remote Similarity	NPC184161
0.6154	Remote Similarity	NPC472109
0.6154	Remote Similarity	NPC101372
0.6154	Remote Similarity	NPC139291
0.6154	Remote Similarity	NPC472108
0.6154	Remote Similarity	NPC472110
0.6146	Remote Similarity	NPC472329
0.6146	Remote Similarity	NPC472330
0.6142	Remote Similarity	NPC475422
0.614	Remote Similarity	NPC285469
0.6135	Remote Similarity	NPC108852
0.6135	Remote Similarity	NPC111586
0.6135	Remote Similarity	NPC261709
0.6125	Remote Similarity	NPC279045
0.6125	Remote Similarity	NPC113325
0.6124	Remote Similarity	NPC97525
0.6124	Remote Similarity	NPC307640
0.6124	Remote Similarity	NPC34508
0.6121	Remote Similarity	NPC262216
0.6118	Remote Similarity	NPC478076
0.6115	Remote Similarity	NPC226662
0.6114	Remote Similarity	NPC470508
0.6108	Remote Similarity	NPC119700
0.6092	Remote Similarity	NPC472101
0.6092	Remote Similarity	NPC472120
0.6092	Remote Similarity	NPC286871
0.6087	Remote Similarity	NPC472107
0.6087	Remote Similarity	NPC79062
0.6087	Remote Similarity	NPC311242
0.6084	Remote Similarity	NPC31171
0.6084	Remote Similarity	NPC237240
0.6082	Remote Similarity	NPC207726
0.608	Remote Similarity	NPC98187
0.6075	Remote Similarity	NPC34271
0.6069	Remote Similarity	NPC67056
0.6062	Remote Similarity	NPC313352
0.6061	Remote Similarity	NPC473922
0.6056	Remote Similarity	NPC203202
0.6056	Remote Similarity	NPC168153
0.6056	Remote Similarity	NPC264482
0.6054	Remote Similarity	NPC66210
0.6053	Remote Similarity	NPC97100
0.6053	Remote Similarity	NPC231342
0.6053	Remote Similarity	NPC473375
0.6051	Remote Similarity	NPC71271
0.6049	Remote Similarity	NPC166667
0.6048	Remote Similarity	NPC173934
0.6048	Remote Similarity	NPC469525
0.6047	Remote Similarity	NPC94167
0.6047	Remote Similarity	NPC172937
0.6045	Remote Similarity	NPC201700
0.6042	Remote Similarity	NPC32200
0.604	Remote Similarity	NPC288232
0.6039	Remote Similarity	NPC472415
0.6037	Remote Similarity	NPC301760
0.6034	Remote Similarity	NPC472123
0.6034	Remote Similarity	NPC476425
0.6033	Remote Similarity	NPC258480
0.6032	Remote Similarity	NPC203972

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 NPC477155 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	623
0.2-0.3	806
0.3-0.4	1964
0.4-0.5	4203
0.5-0.6	1275
0.6-0.7	47
0.7-0.8	1
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
0.7303	Intermediate Similarity	NPD6789	Approved
0.6774	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2212	Approved
0.6759	Remote Similarity	NPD2210	Approved
0.6601	Remote Similarity	NPD1001	Discontinued
0.6582	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD4951	Discontinued
0.6463	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3149	Approved
0.6458	Remote Similarity	NPD3150	Approved
0.6458	Remote Similarity	NPD3148	Approved
0.6458	Remote Similarity	NPD2658	Approved
0.6458	Remote Similarity	NPD2659	Approved
0.6458	Remote Similarity	NPD3147	Approved
0.6433	Remote Similarity	NPD6635	Approved
0.6429	Remote Similarity	NPD2789	Approved
0.6429	Remote Similarity	NPD6026	Approved
0.6414	Remote Similarity	NPD5631	Phase 3
0.6389	Remote Similarity	NPD1762	Approved
0.6389	Remote Similarity	NPD1764	Approved
0.6383	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1036	Approved
0.6375	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6301	Phase 2
0.6319	Remote Similarity	NPD7487	Discontinued
0.6316	Remote Similarity	NPD5599	Discontinued
0.631	Remote Similarity	NPD4120	Approved
0.631	Remote Similarity	NPD4121	Phase 3
0.6284	Remote Similarity	NPD7480	Approved
0.6284	Remote Similarity	NPD7481	Approved
0.6272	Remote Similarity	NPD5742	Approved
0.6272	Remote Similarity	NPD5743	Approved
0.6272	Remote Similarity	NPD5741	Approved
0.6259	Remote Similarity	NPD2622	Approved
0.625	Remote Similarity	NPD478	Approved
0.625	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD2840	Approved
0.6229	Remote Similarity	NPD4639	Approved
0.6229	Remote Similarity	NPD4638	Approved
0.6229	Remote Similarity	NPD4640	Approved
0.6224	Remote Similarity	NPD2678	Approved
0.6224	Remote Similarity	NPD2679	Approved
0.6209	Remote Similarity	NPD6025	Phase 1
0.6198	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5617	Suspended
0.6174	Remote Similarity	NPD7522	Discontinued
0.6169	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD5185	Approved
0.6164	Remote Similarity	NPD5182	Approved
0.6164	Remote Similarity	NPD5184	Approved
0.6162	Remote Similarity	NPD7234	Approved
0.6162	Remote Similarity	NPD7233	Approved
0.6154	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD7461	Approved
0.6127	Remote Similarity	NPD563	Approved
0.6127	Remote Similarity	NPD564	Approved
0.6121	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7474	Suspended
0.6099	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD2038	Approved
0.6096	Remote Similarity	NPD2039	Approved
0.6095	Remote Similarity	NPD7606	Phase 3
0.6084	Remote Similarity	NPD7295	Approved
0.6084	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD4116	Approved
0.6065	Remote Similarity	NPD5578	Approved
0.6065	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD7200	Approved
0.6059	Remote Similarity	NPD2188	Approved
0.6051	Remote Similarity	NPD9701	Discontinued
0.6047	Remote Similarity	NPD2527	Approved
0.6047	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD6281	Approved
0.6042	Remote Similarity	NPD6300	Approved
0.6042	Remote Similarity	NPD6299	Approved
0.6042	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7418	Discontinued
0.6028	Remote Similarity	NPD1417	Approved
0.6028	Remote Similarity	NPD1419	Approved
0.6026	Remote Similarity	NPD6900	Discontinued
0.6025	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5811	Approved
0.6023	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD2895	Discontinued
0.6013	Remote Similarity	NPD1236	Phase 3
0.6013	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD7478	Approved
0.6	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1316	Discontinued
0.6	Remote Similarity	NPD6070	Approved
0.6	Remote Similarity	NPD8355	Approved
0.6	Remote Similarity	NPD8118	Discontinued
0.6	Remote Similarity	NPD6069	Approved
0.6	Remote Similarity	NPD8353	Approved
0.5989	Remote Similarity	NPD4079	Approved
0.5989	Remote Similarity	NPD4076	Approved
0.5977	Remote Similarity	NPD7599	Phase 2
0.5976	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6158	Phase 2
0.5964	Remote Similarity	NPD7082	Approved
0.5962	Remote Similarity	NPD6320	Approved
0.5959	Remote Similarity	NPD7633	Discontinued
0.5959	Remote Similarity	NPD1107	Approved
0.5959	Remote Similarity	NPD1108	Approved
0.5955	Remote Similarity	NPD5862	Discovery
0.5948	Remote Similarity	NPD2340	Discontinued
0.5948	Remote Similarity	NPD1525	Approved
0.5943	Remote Similarity	NPD7600	Phase 2
0.5938	Remote Similarity	NPD2322	Discovery
0.5935	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD3506	Approved
0.5934	Remote Similarity	NPD3505	Approved
0.5932	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.593	Remote Similarity	NPD8354	Approved
0.5928	Remote Similarity	NPD7259	Approved
0.5928	Remote Similarity	NPD4601	Approved
0.5928	Remote Similarity	NPD4600	Approved
0.5926	Remote Similarity	NPD5913	Phase 3
0.5926	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD3595	Approved
0.5912	Remote Similarity	NPD6690	Approved
0.5912	Remote Similarity	NPD3594	Approved
0.5907	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD2914	Approved
0.5906	Remote Similarity	NPD2913	Approved
0.589	Remote Similarity	NPD477	Phase 1
0.589	Remote Similarity	NPD7156	Discontinued
0.5889	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD1516	Approved
0.5886	Remote Similarity	NPD7904	Phase 2
0.5882	Remote Similarity	NPD4702	Approved
0.5882	Remote Similarity	NPD4703	Approved
0.5875	Remote Similarity	NPD6489	Phase 3
0.5873	Remote Similarity	NPD4499	Approved
0.5872	Remote Similarity	NPD950	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.587	Remote Similarity	NPD1394	Approved
0.5867	Remote Similarity	NPD5629	Discontinued
0.5864	Remote Similarity	NPD3110	Approved
0.5864	Remote Similarity	NPD3109	Approved
0.5862	Remote Similarity	NPD990	Approved
0.5862	Remote Similarity	NPD993	Approved
0.586	Remote Similarity	NPD6325	Discontinued
0.5852	Remote Similarity	NPD5989	Phase 1
0.5852	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.585	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7582	Discontinued
0.5849	Remote Similarity	NPD3637	Approved
0.5849	Remote Similarity	NPD3636	Approved
0.5849	Remote Similarity	NPD3635	Approved
0.5848	Remote Similarity	NPD6222	Approved
0.5848	Remote Similarity	NPD6221	Approved
0.5847	Remote Similarity	NPD8122	Approved
0.5847	Remote Similarity	NPD8123	Approved
0.5846	Remote Similarity	NPD6479	Discontinued
0.5845	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD6357	Discontinued
0.5833	Remote Similarity	NPD7795	Phase 2
0.5829	Remote Similarity	NPD2582	Approved
0.5829	Remote Similarity	NPD2581	Approved
0.5829	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.5813	Remote Similarity	NPD2605	Approved
0.5813	Remote Similarity	NPD2606	Approved
0.581	Remote Similarity	NPD2546	Approved
0.581	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.581	Remote Similarity	NPD2545	Approved
0.581	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6037	Discontinued
0.5806	Remote Similarity	NPD5770	Phase 3
0.5806	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4735	Approved
0.5804	Remote Similarity	NPD4734	Approved
0.5804	Remote Similarity	NPD1540	Approved
0.5803	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.58	Remote Similarity	NPD23	Approved
0.5799	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD6737	Phase 2
0.5795	Remote Similarity	NPD6738	Phase 2
0.5793	Remote Similarity	NPD471	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