NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	341.14
Volume:	343.188
LogP:	0.922
LogD:	1.984
LogS:	-1.472
# Rotatable Bonds:	2
TPSA:	29.43
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	6.313
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.453
MDCK Permeability:	1.8931394151877612e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.445
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.595
Plasma Protein Binding (PPB):	60.986114501953125%
Volume Distribution (VD):	2.014
Pgp-substrate:	47.85507583618164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.284
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.204
CYP2D6-inhibitor:	0.329
CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.138
CYP3A4-substrate:	0.793

ADMET: Excretion

Clearance (CL):	5.779
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.724
Rat Oral Acute Toxicity:	0.875
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.867
Carcinogencity:	0.903
Eye Corrosion:	0.046
Eye Irritation:	0.103
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC478079

Natural Product ID:	NPC478079
*Common Name:**	(1R,11S,12E,17S)-14-(chloromethyl)-12-ethylidene-8-aza-14-azoniapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carbaldehyde;chloride
IUPAC Name:	(1R,11S,12E,17S)-14-(chloromethyl)-12-ethylidene-8-aza-14-azoniapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carbaldehyde;chloride
Synonyms:
Standard InCHIKey:	GNFFSTYKCXKGEB-JSUSHCSPSA-N
Standard InCHI:	InChI=1S/C20H21ClN2O.ClH/c1-2-13-10-23(12-21)8-7-20-16-5-3-4-6-17(16)22-19(20)15(11-24)14(13)9-18(20)23;/h2-6,11,14,18H,7-10,12H2,1H3;1H/b13-2-;/t14-,18-,20+,23?;/m0./s1
SMILES:	C/C=C\1/C[N+]2(CC[C@@]34[C@@H]2C[C@@H]1C(=C3NC5=CC=CC=C45)C=O)CCl.[Cl-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122179183
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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	>	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 NPC478079 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	328
0.1-0.2	1813
0.2-0.3	12610
0.3-0.4	19019
0.4-0.5	6434
0.5-0.6	2132
0.6-0.7	341
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9244	High Similarity	NPC264580
0.8444	Intermediate Similarity	NPC243162
0.7762	Intermediate Similarity	NPC116519
0.7586	Intermediate Similarity	NPC472100
0.7538	Intermediate Similarity	NPC192209
0.75	Intermediate Similarity	NPC187036
0.7466	Intermediate Similarity	NPC469735
0.7448	Intermediate Similarity	NPC472103
0.7415	Intermediate Similarity	NPC469740
0.7361	Intermediate Similarity	NPC186284
0.7361	Intermediate Similarity	NPC22082
0.7305	Intermediate Similarity	NPC313352
0.7303	Intermediate Similarity	NPC477156
0.7303	Intermediate Similarity	NPC477157
0.7267	Intermediate Similarity	NPC206592
0.7246	Intermediate Similarity	NPC476950
0.7237	Intermediate Similarity	NPC161827
0.7231	Intermediate Similarity	NPC296163
0.723	Intermediate Similarity	NPC264589
0.7192	Intermediate Similarity	NPC477155
0.7143	Intermediate Similarity	NPC211525
0.7143	Intermediate Similarity	NPC153694
0.7124	Intermediate Similarity	NPC473297
0.7123	Intermediate Similarity	NPC104483
0.7121	Intermediate Similarity	NPC288232
0.7097	Intermediate Similarity	NPC63210
0.7097	Intermediate Similarity	NPC310403
0.7097	Intermediate Similarity	NPC263709
0.7097	Intermediate Similarity	NPC243673
0.7097	Intermediate Similarity	NPC148468
0.7097	Intermediate Similarity	NPC97380
0.7059	Intermediate Similarity	NPC475915
0.704	Intermediate Similarity	NPC291610
0.7039	Intermediate Similarity	NPC33421
0.7006	Intermediate Similarity	NPC472121
0.6966	Remote Similarity	NPC471123
0.6943	Remote Similarity	NPC477158
0.6939	Remote Similarity	NPC130251
0.6923	Remote Similarity	NPC53044
0.6918	Remote Similarity	NPC52059
0.6918	Remote Similarity	NPC470069
0.6901	Remote Similarity	NPC9856
0.6889	Remote Similarity	NPC313449
0.6879	Remote Similarity	NPC6436
0.6871	Remote Similarity	NPC469560
0.6867	Remote Similarity	NPC20144
0.6846	Remote Similarity	NPC164802
0.6846	Remote Similarity	NPC302790
0.6835	Remote Similarity	NPC81229
0.6835	Remote Similarity	NPC255229
0.6818	Remote Similarity	NPC475763
0.681	Remote Similarity	NPC298851
0.681	Remote Similarity	NPC210415
0.681	Remote Similarity	NPC293255
0.681	Remote Similarity	NPC181138
0.681	Remote Similarity	NPC21752
0.681	Remote Similarity	NPC276993
0.6779	Remote Similarity	NPC471574
0.6772	Remote Similarity	NPC469461
0.6755	Remote Similarity	NPC311330
0.6752	Remote Similarity	NPC51054
0.6733	Remote Similarity	NPC2949
0.6732	Remote Similarity	NPC212799
0.673	Remote Similarity	NPC143457
0.6728	Remote Similarity	NPC469462
0.6714	Remote Similarity	NPC283130
0.6714	Remote Similarity	NPC328683
0.6712	Remote Similarity	NPC184437
0.671	Remote Similarity	NPC66936
0.6709	Remote Similarity	NPC104345
0.6691	Remote Similarity	NPC147957
0.6689	Remote Similarity	NPC473868
0.6689	Remote Similarity	NPC63157
0.6688	Remote Similarity	NPC109787
0.6667	Remote Similarity	NPC301760
0.6667	Remote Similarity	NPC469525
0.6667	Remote Similarity	NPC278887
0.6645	Remote Similarity	NPC136002
0.6643	Remote Similarity	NPC145754
0.6639	Remote Similarity	NPC78154
0.6627	Remote Similarity	NPC19679
0.6625	Remote Similarity	NPC225319
0.6624	Remote Similarity	NPC200743
0.6623	Remote Similarity	NPC59084
0.6622	Remote Similarity	NPC325599
0.6619	Remote Similarity	NPC317564
0.6615	Remote Similarity	NPC474695
0.6605	Remote Similarity	NPC475420
0.6603	Remote Similarity	NPC243756
0.6585	Remote Similarity	NPC470926
0.6584	Remote Similarity	NPC194881
0.6584	Remote Similarity	NPC282339
0.6584	Remote Similarity	NPC99632
0.6581	Remote Similarity	NPC21605
0.6579	Remote Similarity	NPC469537
0.6573	Remote Similarity	NPC252794
0.6562	Remote Similarity	NPC56765
0.6556	Remote Similarity	NPC88097
0.6544	Remote Similarity	NPC470550
0.6543	Remote Similarity	NPC469541
0.6533	Remote Similarity	NPC314102
0.6533	Remote Similarity	NPC251722
0.6519	Remote Similarity	NPC478076
0.6512	Remote Similarity	NPC239854
0.651	Remote Similarity	NPC198988
0.6506	Remote Similarity	NPC473743
0.6506	Remote Similarity	NPC473880
0.65	Remote Similarity	NPC129721
0.65	Remote Similarity	NPC316582
0.65	Remote Similarity	NPC113946
0.6497	Remote Similarity	NPC154602
0.6491	Remote Similarity	NPC472294
0.6481	Remote Similarity	NPC469741
0.6481	Remote Similarity	NPC476231
0.6478	Remote Similarity	NPC470507
0.6475	Remote Similarity	NPC228515
0.6467	Remote Similarity	NPC325252
0.6467	Remote Similarity	NPC189812
0.6467	Remote Similarity	NPC329688
0.6462	Remote Similarity	NPC178681
0.646	Remote Similarity	NPC475990
0.646	Remote Similarity	NPC474880
0.646	Remote Similarity	NPC41257
0.646	Remote Similarity	NPC221786
0.6452	Remote Similarity	NPC470440
0.6449	Remote Similarity	NPC313673
0.6442	Remote Similarity	NPC21174
0.6442	Remote Similarity	NPC271797
0.6438	Remote Similarity	NPC29285
0.6438	Remote Similarity	NPC226662
0.6433	Remote Similarity	NPC37548
0.6433	Remote Similarity	NPC318086
0.6424	Remote Similarity	NPC317430
0.642	Remote Similarity	NPC229173
0.6407	Remote Similarity	NPC472123
0.6403	Remote Similarity	NPC476566
0.64	Remote Similarity	NPC267508
0.6398	Remote Similarity	NPC222029
0.6398	Remote Similarity	NPC286427
0.6392	Remote Similarity	NPC40070
0.638	Remote Similarity	NPC472101
0.638	Remote Similarity	NPC472117
0.638	Remote Similarity	NPC472120
0.6374	Remote Similarity	NPC52801
0.6369	Remote Similarity	NPC13367
0.6369	Remote Similarity	NPC475097
0.6369	Remote Similarity	NPC37423
0.6369	Remote Similarity	NPC275305
0.6369	Remote Similarity	NPC477134
0.6364	Remote Similarity	NPC214960
0.6364	Remote Similarity	NPC279527
0.6358	Remote Similarity	NPC206819
0.6358	Remote Similarity	NPC193410
0.6358	Remote Similarity	NPC318065
0.6357	Remote Similarity	NPC81561
0.6353	Remote Similarity	NPC176199
0.6353	Remote Similarity	NPC215795
0.6353	Remote Similarity	NPC133261
0.6352	Remote Similarity	NPC117032
0.6352	Remote Similarity	NPC122106
0.6347	Remote Similarity	NPC158129
0.6347	Remote Similarity	NPC126492
0.6331	Remote Similarity	NPC472122
0.6331	Remote Similarity	NPC24594
0.6329	Remote Similarity	NPC187951
0.6325	Remote Similarity	NPC475248
0.6325	Remote Similarity	NPC63047
0.6319	Remote Similarity	NPC248117
0.6319	Remote Similarity	NPC309531
0.6319	Remote Similarity	NPC472102
0.6319	Remote Similarity	NPC68650
0.6316	Remote Similarity	NPC150259
0.6312	Remote Similarity	NPC162689
0.6312	Remote Similarity	NPC54102
0.631	Remote Similarity	NPC139085
0.631	Remote Similarity	NPC214626
0.631	Remote Similarity	NPC251212
0.631	Remote Similarity	NPC96901
0.6308	Remote Similarity	NPC474582
0.6304	Remote Similarity	NPC205652
0.6303	Remote Similarity	NPC472106
0.6296	Remote Similarity	NPC61013
0.6294	Remote Similarity	NPC326575
0.6294	Remote Similarity	NPC68354
0.6287	Remote Similarity	NPC194411
0.6286	Remote Similarity	NPC148140
0.6282	Remote Similarity	NPC242556
0.6279	Remote Similarity	NPC475962
0.6276	Remote Similarity	NPC122718
0.6276	Remote Similarity	NPC325013
0.6275	Remote Similarity	NPC315051
0.6273	Remote Similarity	NPC38736
0.6266	Remote Similarity	NPC470111
0.6258	Remote Similarity	NPC36495
0.6258	Remote Similarity	NPC276085
0.625	Remote Similarity	NPC285381
0.6243	Remote Similarity	NPC98197
0.6242	Remote Similarity	NPC22079
0.6242	Remote Similarity	NPC162799
0.6242	Remote Similarity	NPC478182

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 NPC478079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	526
0.2-0.3	930
0.3-0.4	1574
0.4-0.5	3576
0.5-0.6	2047
0.6-0.7	258
0.7-0.8	16
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
0.7857	Intermediate Similarity	NPD5631	Phase 3
0.7594	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4116	Approved
0.7344	Intermediate Similarity	NPD2038	Approved
0.7344	Intermediate Similarity	NPD2039	Approved
0.7299	Intermediate Similarity	NPD2840	Approved
0.7293	Intermediate Similarity	NPD2210	Approved
0.7293	Intermediate Similarity	NPD2212	Approved
0.7244	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3150	Approved
0.7231	Intermediate Similarity	NPD2659	Approved
0.7231	Intermediate Similarity	NPD3149	Approved
0.7231	Intermediate Similarity	NPD3147	Approved
0.7231	Intermediate Similarity	NPD3148	Approved
0.7231	Intermediate Similarity	NPD2658	Approved
0.7188	Intermediate Similarity	NPD7633	Discontinued
0.7154	Intermediate Similarity	NPD1764	Approved
0.7154	Intermediate Similarity	NPD1762	Approved
0.7121	Intermediate Similarity	NPD2622	Approved
0.7109	Intermediate Similarity	NPD2678	Approved
0.7109	Intermediate Similarity	NPD2679	Approved
0.7099	Intermediate Similarity	NPD2914	Approved
0.7099	Intermediate Similarity	NPD2913	Approved
0.708	Intermediate Similarity	NPD7461	Approved
0.7068	Intermediate Similarity	NPD6069	Approved
0.7068	Intermediate Similarity	NPD6070	Approved
0.7055	Intermediate Similarity	NPD6606	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6300	Approved
0.7031	Intermediate Similarity	NPD6299	Approved
0.7014	Intermediate Similarity	NPD3385	Approved
0.6984	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5180	Approved
0.697	Remote Similarity	NPD5179	Approved
0.697	Remote Similarity	NPD5181	Approved
0.6944	Remote Similarity	NPD7200	Approved
0.694	Remote Similarity	NPD6660	Discontinued
0.6933	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8353	Approved
0.6928	Remote Similarity	NPD8355	Approved
0.6923	Remote Similarity	NPD1107	Approved
0.6923	Remote Similarity	NPD1108	Approved
0.6918	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1419	Approved
0.6905	Remote Similarity	NPD1417	Approved
0.6899	Remote Similarity	NPD4114	Approved
0.6899	Remote Similarity	NPD4115	Approved
0.6899	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7480	Approved
0.6889	Remote Similarity	NPD7481	Approved
0.6883	Remote Similarity	NPD8402	Approved
0.6883	Remote Similarity	NPD8401	Approved
0.6883	Remote Similarity	NPD8400	Approved
0.6861	Remote Similarity	NPD2340	Discontinued
0.6857	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD477	Phase 1
0.6839	Remote Similarity	NPD8354	Approved
0.6838	Remote Similarity	NPD5657	Phase 3
0.6822	Remote Similarity	NPD3546	Approved
0.6822	Remote Similarity	NPD3545	Approved
0.681	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6900	Discontinued
0.6803	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4411	Phase 1
0.6791	Remote Similarity	NPD5629	Discontinued
0.6786	Remote Similarity	NPD2940	Approved
0.6786	Remote Similarity	NPD2938	Approved
0.6783	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6789	Approved
0.6774	Remote Similarity	NPD5963	Phase 2
0.6774	Remote Similarity	NPD5964	Phase 2
0.6772	Remote Similarity	NPD4734	Approved
0.6772	Remote Similarity	NPD4735	Approved
0.6769	Remote Similarity	NPD5253	Approved
0.6755	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1937	Approved
0.6736	Remote Similarity	NPD6489	Phase 3
0.6726	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD478	Approved
0.671	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1344	Phase 2
0.6644	Remote Similarity	NPD6554	Approved
0.6644	Remote Similarity	NPD45	Approved
0.6643	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4121	Phase 3
0.6624	Remote Similarity	NPD4120	Approved
0.6623	Remote Similarity	NPD1683	Approved
0.6622	Remote Similarity	NPD1998	Approved
0.6622	Remote Similarity	NPD1883	Approved
0.6621	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3654	Approved
0.662	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2143	Discontinued
0.6615	Remote Similarity	NPD563	Approved
0.6615	Remote Similarity	NPD564	Approved
0.6604	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6017	Discontinued
0.6601	Remote Similarity	NPD5933	Phase 3
0.6601	Remote Similarity	NPD5932	Phase 3
0.6601	Remote Similarity	NPD5931	Phase 3
0.66	Remote Similarity	NPD3276	Approved
0.6599	Remote Similarity	NPD5182	Approved
0.6599	Remote Similarity	NPD5185	Approved
0.6599	Remote Similarity	NPD5184	Approved
0.6597	Remote Similarity	NPD7582	Discontinued
0.6594	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD23	Approved
0.6589	Remote Similarity	NPD5103	Approved
0.6585	Remote Similarity	NPD2997	Approved
0.6585	Remote Similarity	NPD2998	Approved
0.6585	Remote Similarity	NPD3000	Approved
0.6582	Remote Similarity	NPD5741	Approved
0.6582	Remote Similarity	NPD5742	Approved
0.6582	Remote Similarity	NPD5743	Approved
0.6581	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6301	Phase 2
0.6579	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5526	Phase 2
0.6575	Remote Similarity	NPD3475	Approved
0.6575	Remote Similarity	NPD3476	Approved
0.6567	Remote Similarity	NPD3001	Approved
0.6567	Remote Similarity	NPD2999	Approved
0.6565	Remote Similarity	NPD990	Approved
0.6565	Remote Similarity	NPD993	Approved
0.6556	Remote Similarity	NPD1953	Discontinued
0.6556	Remote Similarity	NPD4451	Approved
0.6556	Remote Similarity	NPD4450	Approved
0.6528	Remote Similarity	NPD1516	Approved
0.6524	Remote Similarity	NPD4640	Approved
0.6524	Remote Similarity	NPD4638	Approved
0.6524	Remote Similarity	NPD4639	Approved
0.6515	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1525	Approved
0.65	Remote Similarity	NPD4326	Phase 2
0.65	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5254	Discontinued
0.649	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1864	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1866	Approved
0.6483	Remote Similarity	NPD2118	Approved
0.6483	Remote Similarity	NPD2119	Approved
0.6483	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5315	Discontinued
0.6479	Remote Similarity	NPD1498	Approved
0.6471	Remote Similarity	NPD5020	Approved
0.6467	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD2467	Approved
0.6449	Remote Similarity	NPD2464	Approved
0.6449	Remote Similarity	NPD2463	Approved
0.6447	Remote Similarity	NPD2093	Discontinued
0.6446	Remote Similarity	NPD4636	Approved
0.6443	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3323	Discontinued
0.6439	Remote Similarity	NPD1065	Approved
0.6439	Remote Similarity	NPD1064	Approved
0.6438	Remote Similarity	NPD5131	Approved
0.6429	Remote Similarity	NPD3499	Approved
0.6429	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5104	Approved
0.6429	Remote Similarity	NPD3498	Approved
0.6424	Remote Similarity	NPD2733	Approved
0.6424	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD3548	Approved
0.6418	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5178	Approved
0.641	Remote Similarity	NPD1886	Approved
0.6406	Remote Similarity	NPD4813	Approved
0.6406	Remote Similarity	NPD4263	Approved
0.6405	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD7522	Discontinued
0.6402	Remote Similarity	NPD2915	Discontinued
0.6397	Remote Similarity	NPD4165	Phase 2
0.6397	Remote Similarity	NPD3066	Phase 2
0.6395	Remote Similarity	NPD1001	Discontinued
0.6395	Remote Similarity	NPD4857	Phase 1
0.6395	Remote Similarity	NPD1500	Approved
0.6392	Remote Similarity	NPD4462	Approved
0.6392	Remote Similarity	NPD4463	Approved
0.6387	Remote Similarity	NPD5060	Phase 1
0.6385	Remote Similarity	NPD5716	Approved
0.6383	Remote Similarity	NPD6892	Discontinued
0.6383	Remote Similarity	NPD5961	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2304	Approved
0.6382	Remote Similarity	NPD1870	Approved
0.6379	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD1723	Phase 2
0.6377	Remote Similarity	NPD1720	Phase 2
0.6375	Remote Similarity	NPD6285	Phase 2
0.6369	Remote Similarity	NPD4547	Phase 3
0.6364	Remote Similarity	NPD959	Discontinued
0.6364	Remote Similarity	NPD5053	Discontinued
0.6358	Remote Similarity	NPD7599	Phase 2

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