NPASS Compound

Structure

CID225319 OpenBabel06191716022D 29 34 0 0 1 0 0 0 0 0999 V2000 0.5873 3.7756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3373 -0.5162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0189 -1.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3460 -1.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8824 -0.1508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0189 -0.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6730 -1.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2306 -0.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6949 -0.8386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0359 -0.5117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 1.6678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6651 0.7274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4007 1.7921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3093 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3460 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5689 0.6649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6730 -0.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4548 2.4707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1440 0.3510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8986 0.1048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3614 -0.5272 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3460 0.7771 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8806 0.2074 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.7959 0.9783 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2082 2.9715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2571 0.9354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6443 2.8727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4387 -0.6210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 29 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 12 1 0 0 0 0 6 15 2 0 0 0 0 7 17 2 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 6 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 21 1 1 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 22 23 1 1 0 0 0 23 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.2
Volume:	398.997
LogP:	2.518
LogD:	2.79
LogS:	-4.846
# Rotatable Bonds:	4
TPSA:	59.08
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.683
Synthetic Accessibility Score:	5.915
Fsp3:	0.652
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:	-4.88
MDCK Permeability:	2.734546797000803e-05
Pgp-inhibitor:	0.941
Pgp-substrate:	0.189
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	32.39931869506836%
Volume Distribution (VD):	0.958
Pgp-substrate:	70.63352966308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.953
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.3
CYP2D6-substrate:	0.834
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.925

ADMET: Excretion

Clearance (CL):	4.679
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.058
Carcinogencity:	0.764
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.681

Download Data

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

Natural Product: NPC225319

Natural Product ID:	NPC225319
*Common Name:**	Pleiocarpine
IUPAC Name:	n.a.
Synonyms:	Pleiocarpine
Standard InCHIKey:	SQVLFJQJOPEBAA-AUEHJUDRSA-N
Standard InCHI:	InChI=1S/C23H28N2O4/c1-28-18(26)16-14-21-8-5-12-24-13-11-22(19(21)24)15-6-3-4-7-17(15)25(20(27)29-2)23(16,22)10-9-21/h3-4,6-7,16,19H,5,8-14H2,1-2H3/t16-,19-,21?,22+,23?/m0/s1
SMILES:	COC(=O)[C@@H]1CC23CCCN4CC[C@@]5(c6ccccc6N(C(=O)OC)C15CC2)[C@H]34
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL328281
PubChem CID:	44326078
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003755] Aspidofractine 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
NPO6664	Kopsia officinalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28218521]
NPO6664	Kopsia officinalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6664	Kopsia officinalis	Species	Apocynaceae	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
NPT4777	Cell Line	Epidermoid carcinoma cell line		IC50	=	3.1	ug.mL-1	PMID[538440]

☑ 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 NPC225319 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	283
0.1-0.2	1364
0.2-0.3	4522
0.3-0.4	22203
0.4-0.5	10575
0.5-0.6	3031
0.6-0.7	523
0.7-0.8	158
0.8-0.85	24
0.85-0.9	5
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9536	High Similarity	NPC282339
0.9536	High Similarity	NPC99632
0.8528	High Similarity	NPC139085
0.8528	High Similarity	NPC251212
0.8528	High Similarity	NPC214626
0.8491	Intermediate Similarity	NPC248117
0.8439	Intermediate Similarity	NPC221687
0.8428	Intermediate Similarity	NPC193410
0.8408	Intermediate Similarity	NPC478076
0.8402	Intermediate Similarity	NPC52262
0.8375	Intermediate Similarity	NPC201424
0.8365	Intermediate Similarity	NPC61013
0.8365	Intermediate Similarity	NPC113946
0.8232	Intermediate Similarity	NPC167724
0.8232	Intermediate Similarity	NPC223595
0.8232	Intermediate Similarity	NPC224970
0.8204	Intermediate Similarity	NPC264482
0.8204	Intermediate Similarity	NPC203202
0.8199	Intermediate Similarity	NPC36495
0.8182	Intermediate Similarity	NPC473375
0.8182	Intermediate Similarity	NPC97100
0.8156	Intermediate Similarity	NPC471512
0.8155	Intermediate Similarity	NPC260075
0.8137	Intermediate Similarity	NPC123241
0.8098	Intermediate Similarity	NPC293458
0.8061	Intermediate Similarity	NPC279527
0.8061	Intermediate Similarity	NPC214960
0.8025	Intermediate Similarity	NPC264589
0.8	Intermediate Similarity	NPC6974
0.8	Intermediate Similarity	NPC472106
0.7988	Intermediate Similarity	NPC472101
0.7988	Intermediate Similarity	NPC472120
0.7976	Intermediate Similarity	NPC473743
0.7933	Intermediate Similarity	NPC162440
0.7929	Intermediate Similarity	NPC469726
0.7929	Intermediate Similarity	NPC329338
0.7901	Intermediate Similarity	NPC473297
0.7898	Intermediate Similarity	NPC22689
0.7898	Intermediate Similarity	NPC105055
0.7895	Intermediate Similarity	NPC99043
0.7895	Intermediate Similarity	NPC218594
0.7879	Intermediate Similarity	NPC472117
0.787	Intermediate Similarity	NPC476425
0.787	Intermediate Similarity	NPC96901
0.7836	Intermediate Similarity	NPC186669
0.7826	Intermediate Similarity	NPC243756
0.7818	Intermediate Similarity	NPC309531
0.7818	Intermediate Similarity	NPC472102
0.7797	Intermediate Similarity	NPC473298
0.7791	Intermediate Similarity	NPC321211
0.7784	Intermediate Similarity	NPC14994
0.7759	Intermediate Similarity	NPC159963
0.7716	Intermediate Similarity	NPC66936
0.7716	Intermediate Similarity	NPC475763
0.7714	Intermediate Similarity	NPC97584
0.7684	Intermediate Similarity	NPC181928
0.7683	Intermediate Similarity	NPC161827
0.7679	Intermediate Similarity	NPC475420
0.7674	Intermediate Similarity	NPC476441
0.7665	Intermediate Similarity	NPC469741
0.7654	Intermediate Similarity	NPC25401
0.7643	Intermediate Similarity	NPC130251
0.7636	Intermediate Similarity	NPC29285
0.7634	Intermediate Similarity	NPC329833
0.7609	Intermediate Similarity	NPC138830
0.7609	Intermediate Similarity	NPC67904
0.7607	Intermediate Similarity	NPC154602
0.7595	Intermediate Similarity	NPC22082
0.7595	Intermediate Similarity	NPC186284
0.759	Intermediate Similarity	NPC211525
0.759	Intermediate Similarity	NPC153694
0.7588	Intermediate Similarity	NPC475248
0.7588	Intermediate Similarity	NPC63047
0.7571	Intermediate Similarity	NPC322621
0.7564	Intermediate Similarity	NPC471123
0.7561	Intermediate Similarity	NPC122106
0.7558	Intermediate Similarity	NPC473880
0.7558	Intermediate Similarity	NPC285622
0.7545	Intermediate Similarity	NPC243673
0.7545	Intermediate Similarity	NPC263709
0.7545	Intermediate Similarity	NPC63210
0.7545	Intermediate Similarity	NPC310403
0.7545	Intermediate Similarity	NPC97380
0.7545	Intermediate Similarity	NPC148468
0.7543	Intermediate Similarity	NPC11149
0.753	Intermediate Similarity	NPC469536
0.7529	Intermediate Similarity	NPC472115
0.7529	Intermediate Similarity	NPC472114
0.7529	Intermediate Similarity	NPC476326
0.7527	Intermediate Similarity	NPC34717
0.7487	Intermediate Similarity	NPC288110
0.7486	Intermediate Similarity	NPC21425
0.7471	Intermediate Similarity	NPC470069
0.7471	Intermediate Similarity	NPC52059
0.7456	Intermediate Similarity	NPC286871
0.7446	Intermediate Similarity	NPC90967
0.7419	Intermediate Similarity	NPC475489
0.7414	Intermediate Similarity	NPC475097
0.7401	Intermediate Similarity	NPC476428
0.7396	Intermediate Similarity	NPC474058
0.7381	Intermediate Similarity	NPC222029
0.7375	Intermediate Similarity	NPC301760
0.7371	Intermediate Similarity	NPC320147
0.7353	Intermediate Similarity	NPC176983
0.7349	Intermediate Similarity	NPC285381
0.7345	Intermediate Similarity	NPC286994
0.7341	Intermediate Similarity	NPC469915
0.7341	Intermediate Similarity	NPC472118
0.734	Intermediate Similarity	NPC162730
0.7312	Intermediate Similarity	NPC243162
0.7284	Intermediate Similarity	NPC469537
0.7278	Intermediate Similarity	NPC104345
0.7268	Intermediate Similarity	NPC22476
0.7268	Intermediate Similarity	NPC203628
0.7257	Intermediate Similarity	NPC276993
0.7257	Intermediate Similarity	NPC21752
0.7257	Intermediate Similarity	NPC210415
0.7257	Intermediate Similarity	NPC293255
0.7257	Intermediate Similarity	NPC298851
0.7257	Intermediate Similarity	NPC181138
0.7249	Intermediate Similarity	NPC474116
0.7235	Intermediate Similarity	NPC471122
0.7228	Intermediate Similarity	NPC473458
0.7225	Intermediate Similarity	NPC278887
0.7219	Intermediate Similarity	NPC218733
0.7219	Intermediate Similarity	NPC132874
0.7219	Intermediate Similarity	NPC265642
0.7219	Intermediate Similarity	NPC138615
0.7216	Intermediate Similarity	NPC13367
0.7213	Intermediate Similarity	NPC329858
0.7213	Intermediate Similarity	NPC5630
0.7212	Intermediate Similarity	NPC212799
0.7195	Intermediate Similarity	NPC116519
0.7182	Intermediate Similarity	NPC476095
0.7179	Intermediate Similarity	NPC159815
0.7158	Intermediate Similarity	NPC137589
0.7143	Intermediate Similarity	NPC469560
0.7136	Intermediate Similarity	NPC222046
0.7128	Intermediate Similarity	NPC100863
0.7127	Intermediate Similarity	NPC472119
0.7126	Intermediate Similarity	NPC473329
0.7112	Intermediate Similarity	NPC303214
0.7104	Intermediate Similarity	NPC285841
0.7098	Intermediate Similarity	NPC477065
0.7093	Intermediate Similarity	NPC315368
0.7093	Intermediate Similarity	NPC143457
0.7088	Intermediate Similarity	NPC259626
0.7088	Intermediate Similarity	NPC472209
0.7069	Intermediate Similarity	NPC471124
0.7068	Intermediate Similarity	NPC1464
0.7062	Intermediate Similarity	NPC177261
0.7059	Intermediate Similarity	NPC471513
0.7052	Intermediate Similarity	NPC472121
0.7033	Intermediate Similarity	NPC2933
0.7027	Intermediate Similarity	NPC314333
0.7016	Intermediate Similarity	NPC232600
0.7006	Intermediate Similarity	NPC355
0.6989	Remote Similarity	NPC33507
0.6978	Remote Similarity	NPC256288
0.6959	Remote Similarity	NPC195787
0.6959	Remote Similarity	NPC246140
0.6931	Remote Similarity	NPC10653
0.6931	Remote Similarity	NPC318525
0.6919	Remote Similarity	NPC477157
0.6919	Remote Similarity	NPC477156
0.6907	Remote Similarity	NPC185742
0.6907	Remote Similarity	NPC475147
0.6907	Remote Similarity	NPC87714
0.6907	Remote Similarity	NPC475847
0.689	Remote Similarity	NPC315051
0.6885	Remote Similarity	NPC477159
0.6885	Remote Similarity	NPC143533
0.6865	Remote Similarity	NPC282092
0.6865	Remote Similarity	NPC473615
0.6859	Remote Similarity	NPC52557
0.6845	Remote Similarity	NPC474059
0.6845	Remote Similarity	NPC469735
0.6839	Remote Similarity	NPC276085
0.6834	Remote Similarity	NPC127996
0.6832	Remote Similarity	NPC77777
0.6831	Remote Similarity	NPC475962
0.6828	Remote Similarity	NPC472323
0.6828	Remote Similarity	NPC229484
0.6825	Remote Similarity	NPC470485
0.6824	Remote Similarity	NPC318086
0.6818	Remote Similarity	NPC313757
0.6816	Remote Similarity	NPC234772
0.6816	Remote Similarity	NPC126492
0.6816	Remote Similarity	NPC318183
0.6809	Remote Similarity	NPC472097
0.6807	Remote Similarity	NPC471516
0.6805	Remote Similarity	NPC469740
0.68	Remote Similarity	NPC68650
0.6796	Remote Similarity	NPC477394
0.6791	Remote Similarity	NPC284706
0.6791	Remote Similarity	NPC292675
0.6788	Remote Similarity	NPC127178
0.6778	Remote Similarity	NPC307640
0.6778	Remote Similarity	NPC242269
0.6768	Remote Similarity	NPC475133

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 NPC225319 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	558
0.2-0.3	780
0.3-0.4	1884
0.4-0.5	3739
0.5-0.6	1820
0.6-0.7	191
0.7-0.8	13
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
0.7273	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7487	Discontinued
0.7212	Intermediate Similarity	NPD7478	Approved
0.7186	Intermediate Similarity	NPD7606	Phase 3
0.7171	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2994	Approved
0.7108	Intermediate Similarity	NPD7794	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5182	Approved
0.7107	Intermediate Similarity	NPD5184	Approved
0.7107	Intermediate Similarity	NPD5185	Approved
0.7073	Intermediate Similarity	NPD2820	Phase 3
0.7067	Intermediate Similarity	NPD2116	Approved
0.7067	Intermediate Similarity	NPD2117	Pre-registration
0.7067	Intermediate Similarity	NPD2115	Approved
0.7051	Intermediate Similarity	NPD5993	Phase 1
0.7045	Intermediate Similarity	NPD7795	Phase 2
0.7044	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7599	Phase 2
0.7027	Intermediate Similarity	NPD4499	Approved
0.7025	Intermediate Similarity	NPD6489	Phase 3
0.7012	Intermediate Similarity	NPD2365	Approved
0.6994	Remote Similarity	NPD7600	Phase 2
0.6993	Remote Similarity	NPD2946	Phase 2
0.6979	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8630	Approved
0.6974	Remote Similarity	NPD3032	Approved
0.6974	Remote Similarity	NPD3031	Approved
0.6974	Remote Similarity	NPD3030	Approved
0.6951	Remote Similarity	NPD3625	Discontinued
0.6919	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6566	Discontinued
0.6901	Remote Similarity	NPD4121	Phase 3
0.6901	Remote Similarity	NPD2790	Discontinued
0.6901	Remote Similarity	NPD4120	Approved
0.6886	Remote Similarity	NPD7295	Approved
0.6879	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7854	Phase 2
0.6867	Remote Similarity	NPD7082	Approved
0.6864	Remote Similarity	NPD4682	Phase 2
0.6864	Remote Similarity	NPD5942	Approved
0.6864	Remote Similarity	NPD5941	Approved
0.686	Remote Similarity	NPD5742	Approved
0.686	Remote Similarity	NPD5741	Approved
0.686	Remote Similarity	NPD5743	Approved
0.6854	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6416	Phase 2
0.6839	Remote Similarity	NPD4178	Approved
0.6839	Remote Similarity	NPD4176	Approved
0.6833	Remote Similarity	NPD3423	Phase 2
0.6833	Remote Similarity	NPD3422	Phase 3
0.6826	Remote Similarity	NPD7259	Approved
0.6809	Remote Similarity	NPD5504	Discontinued
0.6807	Remote Similarity	NPD6768	Approved
0.68	Remote Similarity	NPD5179	Approved
0.68	Remote Similarity	NPD5180	Approved
0.68	Remote Similarity	NPD5181	Approved
0.6795	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5932	Phase 3
0.6786	Remote Similarity	NPD5931	Phase 3
0.6786	Remote Similarity	NPD5933	Phase 3
0.6766	Remote Similarity	NPD5024	Approved
0.6744	Remote Similarity	NPD8401	Approved
0.6744	Remote Similarity	NPD8402	Approved
0.6744	Remote Similarity	NPD8400	Approved
0.674	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1663	Discontinued
0.6722	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2506	Approved
0.6705	Remote Similarity	NPD5086	Approved
0.6703	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4600	Approved
0.6701	Remote Similarity	NPD4601	Approved
0.6685	Remote Similarity	NPD5997	Discontinued
0.6685	Remote Similarity	NPD4329	Approved
0.6685	Remote Similarity	NPD5430	Discontinued
0.6685	Remote Similarity	NPD4330	Approved
0.6685	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3377	Discontinued
0.6667	Remote Similarity	NPD5600	Discontinued
0.6667	Remote Similarity	NPD2670	Approved
0.6649	Remote Similarity	NPD3471	Approved
0.6649	Remote Similarity	NPD3470	Approved
0.6644	Remote Similarity	NPD4116	Approved
0.6629	Remote Similarity	NPD3790	Phase 2
0.6627	Remote Similarity	NPD5918	Discontinued
0.6616	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6805	Discontinued
0.6615	Remote Similarity	NPD4602	Approved
0.6614	Remote Similarity	NPD7234	Approved
0.6614	Remote Similarity	NPD7233	Approved
0.6613	Remote Similarity	NPD7962	Phase 2
0.6612	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7581	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6457	Approved
0.6611	Remote Similarity	NPD7580	Phase 3
0.6588	Remote Similarity	NPD6622	Phase 1
0.6588	Remote Similarity	NPD6017	Discontinued
0.6582	Remote Similarity	NPD1360	Approved
0.6576	Remote Similarity	NPD3792	Approved
0.6576	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4430	Phase 2
0.6566	Remote Similarity	NPD6358	Phase 2
0.6556	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2427	Approved
0.6548	Remote Similarity	NPD2093	Discontinued
0.6545	Remote Similarity	NPD8240	Discontinued
0.6543	Remote Similarity	NPD5131	Approved
0.6533	Remote Similarity	NPD7633	Discontinued
0.6527	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2037	Approved
0.6506	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4549	Discontinued
0.6474	Remote Similarity	NPD4432	Discontinued
0.6474	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5466	Approved
0.6452	Remote Similarity	NPD3782	Discontinued
0.645	Remote Similarity	NPD2010	Phase 3
0.6448	Remote Similarity	NPD2431	Approved
0.6448	Remote Similarity	NPD2432	Approved
0.6447	Remote Similarity	NPD4500	Approved
0.6447	Remote Similarity	NPD4501	Approved
0.6444	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5263	Approved
0.6441	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5748	Phase 2
0.6436	Remote Similarity	NPD8281	Discontinued
0.6432	Remote Similarity	NPD7205	Discontinued
0.6429	Remote Similarity	NPD2455	Approved
0.6429	Remote Similarity	NPD3170	Approved
0.6429	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2454	Approved
0.6425	Remote Similarity	NPD7569	Approved
0.6425	Remote Similarity	NPD7570	Approved
0.6424	Remote Similarity	NPD1527	Phase 2
0.6417	Remote Similarity	NPD6879	Phase 2
0.6417	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6878	Phase 2
0.6416	Remote Similarity	NPD1801	Approved
0.6416	Remote Similarity	NPD1802	Approved
0.6414	Remote Similarity	NPD6238	Discontinued
0.6407	Remote Similarity	NPD6073	Approved
0.6405	Remote Similarity	NPD2607	Approved
0.6402	Remote Similarity	NPD1070	Approved
0.6402	Remote Similarity	NPD1069	Approved
0.6398	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5578	Approved
0.6386	Remote Similarity	NPD2916	Discontinued
0.6379	Remote Similarity	NPD4888	Discontinued
0.6379	Remote Similarity	NPD7528	Approved
0.6378	Remote Similarity	NPD3828	Approved
0.6378	Remote Similarity	NPD7572	Phase 2
0.6374	Remote Similarity	NPD5526	Phase 2
0.6374	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6342	Discontinued
0.6369	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6294	Approved
0.6369	Remote Similarity	NPD6295	Approved
0.6364	Remote Similarity	NPD2913	Approved
0.6364	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7881	Approved
0.6364	Remote Similarity	NPD2914	Approved
0.6364	Remote Similarity	NPD5581	Approved
0.6364	Remote Similarity	NPD3387	Approved
0.6354	Remote Similarity	NPD7734	Approved
0.6354	Remote Similarity	NPD8270	Approved
0.6348	Remote Similarity	NPD7105	Phase 1
0.6347	Remote Similarity	NPD2791	Discontinued
0.6347	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6070	Approved
0.6346	Remote Similarity	NPD6069	Approved
0.6344	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4365	Phase 2
0.6341	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2039	Approved
0.634	Remote Similarity	NPD2038	Approved
0.6339	Remote Similarity	NPD2404	Discontinued
0.6337	Remote Similarity	NPD2435	Approved
0.6335	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7244	Discontinued
0.6333	Remote Similarity	NPD7275	Approved
0.6331	Remote Similarity	NPD1626	Approved
0.6331	Remote Similarity	NPD7254	Discontinued
0.6326	Remote Similarity	NPD7688	Phase 1
0.6325	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7035	Approved
0.6319	Remote Similarity	NPD7036	Phase 3
0.6316	Remote Similarity	NPD4412	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