NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	322.17
Volume:	329.529
LogP:	1.573
LogD:	1.68
LogS:	-3.513
# Rotatable Bonds:	1
TPSA:	45.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.807
Synthetic Accessibility Score:	6.848
Fsp3:	0.55
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:	-5.001
MDCK Permeability:	1.9901654013665393e-05
Pgp-inhibitor:	0.098
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	60.782081604003906%
Volume Distribution (VD):	2.334
Pgp-substrate:	43.475704193115234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.617
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.316
CYP2D6-inhibitor:	0.473
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.435
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	5.726
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.686
Human Hepatotoxicity (H-HT):	0.559
Drug-inuced Liver Injury (DILI):	0.165
AMES Toxicity:	0.202
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.228
Carcinogencity:	0.563
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC477156

Natural Product ID:	NPC477156
*Common Name:**	(10R,14S,16R,17S)-15-ethenyl-13-methyl-19-oxa-3,13-diazahexacyclo[14.3.1.02,10.04,9.010,15.012,17]icosa-2,4,6,8-tetraen-14-ol
IUPAC Name:	(10R,14S,16R,17S)-15-ethenyl-13-methyl-19-oxa-3,13-diazahexacyclo[14.3.1.02,10.04,9.010,15.012,17]icosa-2,4,6,8-tetraen-14-ol
Synonyms:
Standard InCHIKey:	SFYMRFPMSFVBLE-QAKIGQEHSA-N
Standard InCHI:	InChI=1S/C20H22N2O2/c1-3-19-13-8-16-17-20(19,12-6-4-5-7-14(12)21-17)9-15(11(13)10-24-16)22(2)18(19)23/h3-7,11,13,15-16,18,23H,1,8-10H2,2H3/t11-,13+,15?,16?,18-,19?,20-/m0/s1
SMILES:	CN1[C@H](C2([C@@H]3CC4C5=NC6=CC=CC=C6[C@@]52CC1[C@H]3CO4)C=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	163092148
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000	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 NPC477156 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	253
0.1-0.2	1304
0.2-0.3	4773
0.3-0.4	17209
0.4-0.5	14429
0.5-0.6	4155
0.6-0.7	522
0.7-0.8	43
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477157
0.9375	High Similarity	NPC116519
0.9272	High Similarity	NPC477158
0.8639	High Similarity	NPC243162
0.8543	High Similarity	NPC472100
0.84	Intermediate Similarity	NPC477155
0.816	Intermediate Similarity	NPC469462
0.8052	Intermediate Similarity	NPC472103
0.7716	Intermediate Similarity	NPC473297
0.763	Intermediate Similarity	NPC475962
0.75	Intermediate Similarity	NPC264589
0.747	Intermediate Similarity	NPC469461
0.7456	Intermediate Similarity	NPC278887
0.7384	Intermediate Similarity	NPC276993
0.7384	Intermediate Similarity	NPC181138
0.7384	Intermediate Similarity	NPC21752
0.7384	Intermediate Similarity	NPC298851
0.7384	Intermediate Similarity	NPC293255
0.7384	Intermediate Similarity	NPC210415
0.7303	Intermediate Similarity	NPC469460
0.7303	Intermediate Similarity	NPC478079
0.7299	Intermediate Similarity	NPC472122
0.7299	Intermediate Similarity	NPC24594
0.7288	Intermediate Similarity	NPC19679
0.7283	Intermediate Similarity	NPC473880
0.7273	Intermediate Similarity	NPC472105
0.7273	Intermediate Similarity	NPC187827
0.7238	Intermediate Similarity	NPC105055
0.7238	Intermediate Similarity	NPC22689
0.7212	Intermediate Similarity	NPC475763
0.7202	Intermediate Similarity	NPC211525
0.7202	Intermediate Similarity	NPC153694
0.7193	Intermediate Similarity	NPC472106
0.7176	Intermediate Similarity	NPC472121
0.7176	Intermediate Similarity	NPC472101
0.7176	Intermediate Similarity	NPC472120
0.7162	Intermediate Similarity	NPC264580
0.716	Intermediate Similarity	NPC310403
0.716	Intermediate Similarity	NPC63210
0.716	Intermediate Similarity	NPC97380
0.716	Intermediate Similarity	NPC263709
0.716	Intermediate Similarity	NPC243673
0.716	Intermediate Similarity	NPC148468
0.7134	Intermediate Similarity	NPC212799
0.7111	Intermediate Similarity	NPC52262
0.7095	Intermediate Similarity	NPC472110
0.7095	Intermediate Similarity	NPC139291
0.7095	Intermediate Similarity	NPC472108
0.7095	Intermediate Similarity	NPC472109
0.7093	Intermediate Similarity	NPC475420
0.7093	Intermediate Similarity	NPC470069
0.7093	Intermediate Similarity	NPC52059
0.7062	Intermediate Similarity	NPC326575
0.7055	Intermediate Similarity	NPC311330
0.7045	Intermediate Similarity	NPC475097
0.7017	Intermediate Similarity	NPC472209
0.7	Intermediate Similarity	NPC474077
0.7	Intermediate Similarity	NPC52801
0.6982	Remote Similarity	NPC161827
0.6978	Remote Similarity	NPC291759
0.6927	Remote Similarity	NPC133261
0.6923	Remote Similarity	NPC133591
0.6923	Remote Similarity	NPC295478
0.6923	Remote Similarity	NPC476095
0.6919	Remote Similarity	NPC225319
0.6919	Remote Similarity	NPC143457
0.6918	Remote Similarity	NPC132847
0.6893	Remote Similarity	NPC139085
0.6893	Remote Similarity	NPC214626
0.6893	Remote Similarity	NPC251212
0.6893	Remote Similarity	NPC473743
0.6885	Remote Similarity	NPC207033
0.6885	Remote Similarity	NPC38823
0.6879	Remote Similarity	NPC99632
0.6879	Remote Similarity	NPC282339
0.6879	Remote Similarity	NPC472117
0.6875	Remote Similarity	NPC257354
0.6875	Remote Similarity	NPC469915
0.6868	Remote Similarity	NPC245741
0.6867	Remote Similarity	NPC470579
0.6865	Remote Similarity	NPC95783
0.6854	Remote Similarity	NPC329688
0.6854	Remote Similarity	NPC189812
0.6848	Remote Similarity	NPC285841
0.6842	Remote Similarity	NPC29285
0.6839	Remote Similarity	NPC325013
0.6825	Remote Similarity	NPC475559
0.6821	Remote Similarity	NPC472102
0.6821	Remote Similarity	NPC309531
0.6816	Remote Similarity	NPC320147
0.6813	Remote Similarity	NPC472104
0.6811	Remote Similarity	NPC217294
0.6798	Remote Similarity	NPC106593
0.6782	Remote Similarity	NPC140311
0.6779	Remote Similarity	NPC470550
0.6774	Remote Similarity	NPC469470
0.6774	Remote Similarity	NPC469501
0.6771	Remote Similarity	NPC471512
0.6766	Remote Similarity	NPC469735
0.6765	Remote Similarity	NPC473667
0.6765	Remote Similarity	NPC275839
0.6755	Remote Similarity	NPC203972
0.6751	Remote Similarity	NPC475422
0.674	Remote Similarity	NPC218594
0.674	Remote Similarity	NPC99043
0.6735	Remote Similarity	NPC87755
0.6734	Remote Similarity	NPC475602
0.6723	Remote Similarity	NPC154293
0.6722	Remote Similarity	NPC476441
0.6721	Remote Similarity	NPC98197
0.672	Remote Similarity	NPC221687
0.6709	Remote Similarity	NPC197680
0.6709	Remote Similarity	NPC259098
0.6708	Remote Similarity	NPC64897
0.6708	Remote Similarity	NPC90693
0.6706	Remote Similarity	NPC206592
0.6704	Remote Similarity	NPC472123
0.6703	Remote Similarity	NPC282092
0.6688	Remote Similarity	NPC278097
0.6686	Remote Similarity	NPC114808
0.6684	Remote Similarity	NPC231342
0.6667	Remote Similarity	NPC13367
0.6649	Remote Similarity	NPC28510
0.6649	Remote Similarity	NPC90967
0.6649	Remote Similarity	NPC302548
0.6648	Remote Similarity	NPC126492
0.6648	Remote Similarity	NPC469541
0.6648	Remote Similarity	NPC158129
0.6647	Remote Similarity	NPC217801
0.6632	Remote Similarity	NPC475489
0.6632	Remote Similarity	NPC79129
0.6632	Remote Similarity	NPC249150
0.6632	Remote Similarity	NPC81654
0.6632	Remote Similarity	NPC195461
0.6632	Remote Similarity	NPC49196
0.6632	Remote Similarity	NPC313985
0.663	Remote Similarity	NPC264482
0.663	Remote Similarity	NPC203202
0.6629	Remote Similarity	NPC81229
0.6629	Remote Similarity	NPC255229
0.6627	Remote Similarity	NPC469740
0.6626	Remote Similarity	NPC175870
0.6615	Remote Similarity	NPC477135
0.6612	Remote Similarity	NPC15840
0.6611	Remote Similarity	NPC96901
0.6609	Remote Similarity	NPC113946
0.6609	Remote Similarity	NPC104345
0.6607	Remote Similarity	NPC237240
0.6607	Remote Similarity	NPC31171
0.6605	Remote Similarity	NPC184437
0.6597	Remote Similarity	NPC473375
0.6597	Remote Similarity	NPC97100
0.6593	Remote Similarity	NPC260075
0.6593	Remote Similarity	NPC211997
0.6591	Remote Similarity	NPC176983
0.6591	Remote Similarity	NPC85651
0.6587	Remote Similarity	NPC473922
0.6584	Remote Similarity	NPC42423
0.6578	Remote Similarity	NPC181928
0.6573	Remote Similarity	NPC98187
0.6561	Remote Similarity	NPC470483
0.6556	Remote Similarity	NPC205652
0.6552	Remote Similarity	NPC473837
0.6552	Remote Similarity	NPC10730
0.6552	Remote Similarity	NPC10875
0.655	Remote Similarity	NPC318086
0.6548	Remote Similarity	NPC262216
0.6548	Remote Similarity	NPC472111
0.6538	Remote Similarity	NPC134586
0.6536	Remote Similarity	NPC317430
0.6534	Remote Similarity	NPC315368
0.6534	Remote Similarity	NPC474058
0.6532	Remote Similarity	NPC478076
0.6528	Remote Similarity	NPC50503
0.6522	Remote Similarity	NPC300688
0.6519	Remote Similarity	NPC476425
0.6513	Remote Similarity	NPC472329
0.6513	Remote Similarity	NPC472330
0.6508	Remote Similarity	NPC473298
0.6506	Remote Similarity	NPC239770
0.6505	Remote Similarity	NPC97584
0.6505	Remote Similarity	NPC165201
0.6503	Remote Similarity	NPC313352
0.6503	Remote Similarity	NPC151939
0.65	Remote Similarity	NPC126066
0.65	Remote Similarity	NPC40488
0.6492	Remote Similarity	NPC470485
0.6491	Remote Similarity	NPC201692
0.6489	Remote Similarity	NPC119700
0.6488	Remote Similarity	NPC223590
0.6486	Remote Similarity	NPC302191
0.648	Remote Similarity	NPC472115
0.648	Remote Similarity	NPC19555
0.648	Remote Similarity	NPC472114
0.6477	Remote Similarity	NPC235460
0.6477	Remote Similarity	NPC162440
0.6477	Remote Similarity	NPC291359
0.6474	Remote Similarity	NPC472097
0.6474	Remote Similarity	NPC25401
0.6471	Remote Similarity	NPC173934

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 NPC477156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	562
0.2-0.3	727
0.3-0.4	1655
0.4-0.5	3967
0.5-0.6	1926
0.6-0.7	151
0.7-0.8	4
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
0.7439	Intermediate Similarity	NPD4120	Approved
0.7439	Intermediate Similarity	NPD4121	Phase 3
0.7394	Intermediate Similarity	NPD5743	Approved
0.7394	Intermediate Similarity	NPD5741	Approved
0.7394	Intermediate Similarity	NPD5742	Approved
0.723	Intermediate Similarity	NPD2212	Approved
0.723	Intermediate Similarity	NPD2210	Approved
0.7222	Intermediate Similarity	NPD5595	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6789	Approved
0.7091	Intermediate Similarity	NPD5881	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6606	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3149	Approved
0.6939	Remote Similarity	NPD2659	Approved
0.6939	Remote Similarity	NPD3150	Approved
0.6939	Remote Similarity	NPD3147	Approved
0.6939	Remote Similarity	NPD2658	Approved
0.6939	Remote Similarity	NPD3148	Approved
0.691	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1764	Approved
0.6871	Remote Similarity	NPD1762	Approved
0.6867	Remote Similarity	NPD7522	Discontinued
0.6848	Remote Similarity	NPD4951	Discontinued
0.6813	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6301	Phase 2
0.6779	Remote Similarity	NPD5631	Phase 3
0.676	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6026	Approved
0.6709	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7474	Suspended
0.6667	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4600	Approved
0.6632	Remote Similarity	NPD4601	Approved
0.663	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2622	Approved
0.6611	Remote Similarity	NPD7418	Discontinued
0.6607	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7461	Approved
0.6599	Remote Similarity	NPD2679	Approved
0.6599	Remote Similarity	NPD2678	Approved
0.6592	Remote Similarity	NPD3051	Approved
0.658	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6025	Phase 1
0.6543	Remote Similarity	NPD8118	Discontinued
0.6536	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7600	Phase 2
0.6528	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1001	Discontinued
0.6519	Remote Similarity	NPD6320	Approved
0.6509	Remote Similarity	NPD7295	Approved
0.6503	Remote Similarity	NPD5185	Approved
0.6503	Remote Similarity	NPD5182	Approved
0.6503	Remote Similarity	NPD5184	Approved
0.6503	Remote Similarity	NPD7200	Approved
0.65	Remote Similarity	NPD7795	Phase 2
0.6474	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD2970	Approved
0.6464	Remote Similarity	NPD2969	Approved
0.6461	Remote Similarity	NPD6635	Approved
0.646	Remote Similarity	NPD2606	Approved
0.646	Remote Similarity	NPD3595	Approved
0.646	Remote Similarity	NPD3594	Approved
0.646	Remote Similarity	NPD2605	Approved
0.6457	Remote Similarity	NPD2789	Approved
0.6453	Remote Similarity	NPD6222	Approved
0.6453	Remote Similarity	NPD6221	Approved
0.6444	Remote Similarity	NPD4639	Approved
0.6444	Remote Similarity	NPD4640	Approved
0.6444	Remote Similarity	NPD4638	Approved
0.6441	Remote Similarity	NPD5599	Discontinued
0.6441	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6281	Approved
0.642	Remote Similarity	NPD5155	Approved
0.642	Remote Similarity	NPD5156	Approved
0.6419	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3637	Approved
0.6398	Remote Similarity	NPD3635	Approved
0.6398	Remote Similarity	NPD3636	Approved
0.6392	Remote Similarity	NPD478	Approved
0.6384	Remote Similarity	NPD7599	Phase 2
0.6379	Remote Similarity	NPD8401	Approved
0.6379	Remote Similarity	NPD6158	Phase 2
0.6379	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8400	Approved
0.6379	Remote Similarity	NPD8402	Approved
0.6379	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7479	Phase 2
0.6368	Remote Similarity	NPD7234	Approved
0.6368	Remote Similarity	NPD7233	Approved
0.6358	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5862	Discovery
0.6353	Remote Similarity	NPD7487	Discontinued
0.6339	Remote Similarity	NPD2489	Approved
0.6339	Remote Similarity	NPD27	Approved
0.6337	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2843	Phase 2
0.6335	Remote Similarity	NPD2845	Phase 2
0.6329	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4274	Approved
0.6319	Remote Similarity	NPD3720	Discontinued
0.6319	Remote Similarity	NPD4275	Approved
0.6316	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8021	Approved
0.6316	Remote Similarity	NPD8020	Approved
0.6316	Remote Similarity	NPD8131	Suspended
0.6312	Remote Similarity	NPD5578	Approved
0.6312	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD5617	Suspended
0.6306	Remote Similarity	NPD7725	Approved
0.6305	Remote Similarity	NPD5936	Approved
0.6305	Remote Similarity	NPD5939	Approved
0.6296	Remote Similarity	NPD6227	Discontinued
0.6294	Remote Similarity	NPD7082	Approved
0.6292	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2882	Phase 1
0.6284	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2216	Approved
0.6284	Remote Similarity	NPD2215	Approved
0.628	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5596	Phase 2
0.6277	Remote Similarity	NPD7962	Phase 2
0.6272	Remote Similarity	NPD4726	Approved
0.6272	Remote Similarity	NPD4721	Approved
0.6272	Remote Similarity	NPD4725	Approved
0.6271	Remote Similarity	NPD2527	Approved
0.6259	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7259	Approved
0.6257	Remote Similarity	NPD6879	Phase 2
0.6257	Remote Similarity	NPD6878	Phase 2
0.625	Remote Similarity	NPD2038	Approved
0.625	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5811	Approved
0.625	Remote Similarity	NPD8354	Approved
0.625	Remote Similarity	NPD2039	Approved
0.625	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8063	Discontinued
0.6244	Remote Similarity	NPD2177	Approved
0.6244	Remote Similarity	NPD2176	Approved
0.6244	Remote Similarity	NPD2175	Phase 3
0.6243	Remote Similarity	NPD2421	Approved
0.6243	Remote Similarity	NPD2420	Approved
0.6237	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.623	Remote Similarity	NPD2383	Phase 1
0.6229	Remote Similarity	NPD8355	Approved
0.6229	Remote Similarity	NPD8353	Approved
0.6228	Remote Similarity	NPD6544	Discontinued
0.6225	Remote Similarity	NPD1108	Approved
0.6225	Remote Similarity	NPD4116	Approved
0.6225	Remote Similarity	NPD1107	Approved
0.6221	Remote Similarity	NPD8323	Discontinued
0.6218	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5913	Phase 3
0.6211	Remote Similarity	NPD1036	Approved
0.6207	Remote Similarity	NPD4702	Approved
0.6207	Remote Similarity	NPD4703	Approved
0.6207	Remote Similarity	NPD4682	Phase 2
0.6205	Remote Similarity	NPD3109	Approved
0.6205	Remote Similarity	NPD3110	Approved
0.6203	Remote Similarity	NPD4076	Approved
0.6203	Remote Similarity	NPD4079	Approved
0.62	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD6978	Phase 2
0.6197	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3975	Discontinued
0.6196	Remote Similarity	NPD7582	Discontinued
0.6193	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD2188	Approved
0.619	Remote Similarity	NPD1419	Approved
0.619	Remote Similarity	NPD4719	Phase 2
0.619	Remote Similarity	NPD7883	Discontinued
0.619	Remote Similarity	NPD1417	Approved
0.6183	Remote Similarity	NPD2382	Approved
0.6183	Remote Similarity	NPD2380	Approved
0.6183	Remote Similarity	NPD2381	Approved
0.6183	Remote Similarity	NPD5100	Phase 3
0.6182	Remote Similarity	NPD864	Approved
0.6182	Remote Similarity	NPD865	Approved
0.6179	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6900	Discontinued
0.6171	Remote Similarity	NPD1405	Approved
0.617	Remote Similarity	NPD6833	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data