NPASS Compound

Structure

NPC473329 OpenBabel07101718182D 25 28 0 0 1 0 0 0 0 0999 V2000 2.5085 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9769 5.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8526 2.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2453 1.3263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8923 2.3092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6777 0.5451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9275 2.8622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3248 1.5281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6354 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7175 0.6461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6292 3.7805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8362 0.4828 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8362 1.4483 0.0000 N 0 0 0 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 -0.8362 -1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6848 3.9812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2752 4.4980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 25 1 0 0 0 0 3 19 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 14 2 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 17 23 2 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 20 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.18
Volume:	352.796
LogP:	2.662
LogD:	2.927
LogS:	-4.05
# Rotatable Bonds:	3
TPSA:	58.64
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	4.464
Fsp3:	0.5
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:	-4.704
MDCK Permeability:	2.8897435186081566e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.223
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.636

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	50.87172317504883%
Volume Distribution (VD):	1.237
Pgp-substrate:	42.197410583496094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.181
CYP1A2-substrate:	0.736
CYP2C19-inhibitor:	0.712
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.674
CYP2C9-substrate:	0.264
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	7.213
Half-life (T1/2):	0.33

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.357
Drug-inuced Liver Injury (DILI):	0.369
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.429
Carcinogencity:	0.669
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.259

Download Data

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

Natural Product: NPC473329

Natural Product ID:	NPC473329
*Common Name:**	Arboloscine
IUPAC Name:	n.a.
Synonyms:	Arboloscine
Standard InCHIKey:	FLSJNIUAKREQKD-LWRAOMQUSA-N
Standard InCHI:	InChI=1S/C20H24N2O3/c1-3-19-10-6-12-21-20(19)15(13-18(24)25-2)14-7-4-5-8-16(14)22(20)17(23)9-11-19/h4-5,7-8,13,21H,3,6,9-12H2,1-2H3/b15-13-/t19-,20?/m1/s1
SMILES:	CCC12CCCNC13C(=CC(=O)OC)C4=CC=CC=C4N3C(=O)CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400902
PubChem CID:	44445748
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0001879] Delta amino acids and derivatives

*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
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665953]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	Yunnan, China	n.a.	PMID[19133778]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31241923]
NPO2700	Kopsia arborea	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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	15.0	ug.mL-1	PMID[492467]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11.0	ug.mL-1	PMID[492467]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11200.0	nM	PMID[492467]

☑ 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 NPC473329 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	262
0.1-0.2	1693
0.2-0.3	7894
0.3-0.4	21258
0.4-0.5	8353
0.5-0.6	2739
0.6-0.7	449
0.7-0.8	43
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8741	High Similarity	NPC469560
0.8472	Intermediate Similarity	NPC471123
0.8089	Intermediate Similarity	NPC61013
0.8038	Intermediate Similarity	NPC193410
0.7987	Intermediate Similarity	NPC248117
0.7862	Intermediate Similarity	NPC123241
0.7862	Intermediate Similarity	NPC222029
0.7818	Intermediate Similarity	NPC285622
0.7812	Intermediate Similarity	NPC471122
0.7812	Intermediate Similarity	NPC276085
0.7744	Intermediate Similarity	NPC167724
0.7744	Intermediate Similarity	NPC224970
0.7744	Intermediate Similarity	NPC223595
0.7716	Intermediate Similarity	NPC293458
0.7658	Intermediate Similarity	NPC66936
0.7643	Intermediate Similarity	NPC109787
0.7622	Intermediate Similarity	NPC471124
0.7605	Intermediate Similarity	NPC242269
0.7593	Intermediate Similarity	NPC36495
0.7547	Intermediate Similarity	NPC243756
0.7515	Intermediate Similarity	NPC203202
0.7515	Intermediate Similarity	NPC264482
0.7427	Intermediate Similarity	NPC99043
0.7427	Intermediate Similarity	NPC218594
0.7427	Intermediate Similarity	NPC6974
0.7365	Intermediate Similarity	NPC279527
0.7365	Intermediate Similarity	NPC214960
0.7353	Intermediate Similarity	NPC469726
0.7353	Intermediate Similarity	NPC329338
0.7346	Intermediate Similarity	NPC478076
0.7299	Intermediate Similarity	NPC159963
0.7289	Intermediate Similarity	NPC99632
0.7289	Intermediate Similarity	NPC282339
0.7284	Intermediate Similarity	NPC122106
0.7267	Intermediate Similarity	NPC186669
0.7248	Intermediate Similarity	NPC252794
0.7244	Intermediate Similarity	NPC130251
0.7229	Intermediate Similarity	NPC474058
0.7212	Intermediate Similarity	NPC113946
0.7193	Intermediate Similarity	NPC177261
0.7186	Intermediate Similarity	NPC176983
0.7178	Intermediate Similarity	NPC117032
0.7152	Intermediate Similarity	NPC469536
0.7151	Intermediate Similarity	NPC128582
0.7143	Intermediate Similarity	NPC162417
0.7143	Intermediate Similarity	NPC316104
0.7135	Intermediate Similarity	NPC14994
0.7126	Intermediate Similarity	NPC225319
0.7117	Intermediate Similarity	NPC154602
0.7093	Intermediate Similarity	NPC139085
0.7093	Intermediate Similarity	NPC251212
0.7093	Intermediate Similarity	NPC214626
0.7089	Intermediate Similarity	NPC471164
0.7089	Intermediate Similarity	NPC470301
0.7062	Intermediate Similarity	NPC97584
0.7056	Intermediate Similarity	NPC473569
0.7024	Intermediate Similarity	NPC472102
0.7024	Intermediate Similarity	NPC309531
0.7024	Intermediate Similarity	NPC68650
0.7022	Intermediate Similarity	NPC259626
0.7017	Intermediate Similarity	NPC25401
0.6994	Remote Similarity	NPC96901
0.6988	Remote Similarity	NPC161827
0.6987	Remote Similarity	NPC173295
0.6983	Remote Similarity	NPC473615
0.6981	Remote Similarity	NPC186284
0.6981	Remote Similarity	NPC22082
0.6981	Remote Similarity	NPC301760
0.6974	Remote Similarity	NPC145754
0.6966	Remote Similarity	NPC2933
0.6959	Remote Similarity	NPC472115
0.6959	Remote Similarity	NPC472114
0.6957	Remote Similarity	NPC245916
0.6954	Remote Similarity	NPC470343
0.6954	Remote Similarity	NPC470548
0.6954	Remote Similarity	NPC472244
0.6946	Remote Similarity	NPC29285
0.6944	Remote Similarity	NPC229484
0.6943	Remote Similarity	NPC267508
0.6918	Remote Similarity	NPC315051
0.6913	Remote Similarity	NPC475915
0.691	Remote Similarity	NPC256288
0.6909	Remote Similarity	NPC314223
0.6908	Remote Similarity	NPC322433
0.6906	Remote Similarity	NPC292675
0.6906	Remote Similarity	NPC196251
0.6906	Remote Similarity	NPC102338
0.6906	Remote Similarity	NPC111602
0.6906	Remote Similarity	NPC63199
0.6894	Remote Similarity	NPC469537
0.6889	Remote Similarity	NPC141612
0.6889	Remote Similarity	NPC17273
0.6889	Remote Similarity	NPC135601
0.6882	Remote Similarity	NPC286871
0.6882	Remote Similarity	NPC472120
0.6882	Remote Similarity	NPC472101
0.6875	Remote Similarity	NPC260075
0.6868	Remote Similarity	NPC5630
0.6867	Remote Similarity	NPC285381
0.6864	Remote Similarity	NPC310403
0.6864	Remote Similarity	NPC263709
0.6864	Remote Similarity	NPC63210
0.6864	Remote Similarity	NPC97380
0.6864	Remote Similarity	NPC243673
0.6864	Remote Similarity	NPC148468
0.6848	Remote Similarity	NPC318086
0.6831	Remote Similarity	NPC22476
0.6831	Remote Similarity	NPC203628
0.6823	Remote Similarity	NPC285192
0.6821	Remote Similarity	NPC254698
0.6802	Remote Similarity	NPC472106
0.68	Remote Similarity	NPC476425
0.68	Remote Similarity	NPC161861
0.6791	Remote Similarity	NPC100863
0.679	Remote Similarity	NPC308197
0.6784	Remote Similarity	NPC194881
0.6784	Remote Similarity	NPC469741
0.6779	Remote Similarity	NPC226143
0.6774	Remote Similarity	NPC472245
0.6758	Remote Similarity	NPC21425
0.6755	Remote Similarity	NPC268534
0.6748	Remote Similarity	NPC190945
0.6743	Remote Similarity	NPC355
0.6733	Remote Similarity	NPC279385
0.6733	Remote Similarity	NPC179605
0.6724	Remote Similarity	NPC63047
0.6724	Remote Similarity	NPC475248
0.6723	Remote Similarity	NPC476441
0.671	Remote Similarity	NPC209389
0.6706	Remote Similarity	NPC153694
0.6706	Remote Similarity	NPC104345
0.6706	Remote Similarity	NPC211525
0.6705	Remote Similarity	NPC470069
0.6705	Remote Similarity	NPC52059
0.6704	Remote Similarity	NPC286994
0.6702	Remote Similarity	NPC477179
0.6689	Remote Similarity	NPC103292
0.6687	Remote Similarity	NPC242000
0.6686	Remote Similarity	NPC472118
0.6686	Remote Similarity	NPC472121
0.6686	Remote Similarity	NPC473297
0.6686	Remote Similarity	NPC472117
0.6685	Remote Similarity	NPC28848
0.6685	Remote Similarity	NPC14849
0.6685	Remote Similarity	NPC14325
0.6685	Remote Similarity	NPC473298
0.6684	Remote Similarity	NPC303214
0.6667	Remote Similarity	NPC187231
0.6667	Remote Similarity	NPC477178
0.6667	Remote Similarity	NPC477180
0.6667	Remote Similarity	NPC291962
0.6667	Remote Similarity	NPC477181
0.6667	Remote Similarity	NPC177684
0.6667	Remote Similarity	NPC254850
0.6649	Remote Similarity	NPC471436
0.6648	Remote Similarity	NPC131450
0.6648	Remote Similarity	NPC182057
0.6648	Remote Similarity	NPC147298
0.6647	Remote Similarity	NPC36836
0.6647	Remote Similarity	NPC21174
0.6647	Remote Similarity	NPC63370
0.6647	Remote Similarity	NPC271797
0.6646	Remote Similarity	NPC319645
0.6633	Remote Similarity	NPC471197
0.6632	Remote Similarity	NPC477173
0.6632	Remote Similarity	NPC470490
0.6632	Remote Similarity	NPC477174
0.6631	Remote Similarity	NPC230313
0.6631	Remote Similarity	NPC220151
0.6631	Remote Similarity	NPC19692
0.663	Remote Similarity	NPC477159
0.6628	Remote Similarity	NPC201424
0.6623	Remote Similarity	NPC161956
0.6623	Remote Similarity	NPC258531
0.6623	Remote Similarity	NPC112373
0.6613	Remote Similarity	NPC55493
0.661	Remote Similarity	NPC293255
0.661	Remote Similarity	NPC21752
0.661	Remote Similarity	NPC181138
0.661	Remote Similarity	NPC276993
0.661	Remote Similarity	NPC210415
0.661	Remote Similarity	NPC298851
0.6604	Remote Similarity	NPC253476
0.6603	Remote Similarity	NPC150863
0.66	Remote Similarity	NPC471198
0.6598	Remote Similarity	NPC470488
0.6598	Remote Similarity	NPC243850
0.6596	Remote Similarity	NPC79356
0.6596	Remote Similarity	NPC102592
0.6595	Remote Similarity	NPC105055
0.6595	Remote Similarity	NPC22689
0.6591	Remote Similarity	NPC469915
0.6581	Remote Similarity	NPC250476
0.6579	Remote Similarity	NPC257490
0.6576	Remote Similarity	NPC181928
0.6573	Remote Similarity	NPC248862
0.6573	Remote Similarity	NPC328611
0.6571	Remote Similarity	NPC470509
0.6564	Remote Similarity	NPC471950
0.6564	Remote Similarity	NPC475259

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 NPC473329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	527
0.2-0.3	872
0.3-0.4	1331
0.4-0.5	3437
0.5-0.6	2462
0.6-0.7	358
0.7-0.8	23
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
0.7763	Intermediate Similarity	NPD3625	Discontinued
0.7692	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5918	Discontinued
0.7261	Intermediate Similarity	NPD6566	Discontinued
0.7226	Intermediate Similarity	NPD6358	Phase 2
0.7178	Intermediate Similarity	NPD3248	Phase 1
0.7152	Intermediate Similarity	NPD6768	Approved
0.7152	Intermediate Similarity	NPD4549	Discontinued
0.7123	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4464	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5993	Phase 1
0.7078	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3790	Phase 2
0.7037	Intermediate Similarity	NPD1801	Approved
0.7037	Intermediate Similarity	NPD1802	Approved
0.7035	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5184	Approved
0.7032	Intermediate Similarity	NPD5185	Approved
0.7032	Intermediate Similarity	NPD5182	Approved
0.7027	Intermediate Similarity	NPD1124	Approved
0.7027	Intermediate Similarity	NPD1123	Approved
0.7006	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6342	Discontinued
0.7	Intermediate Similarity	NPD9541	Approved
0.7	Intermediate Similarity	NPD9539	Approved
0.6994	Remote Similarity	NPD5942	Approved
0.6994	Remote Similarity	NPD5941	Approved
0.6993	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5186	Approved
0.6977	Remote Similarity	NPD5183	Approved
0.6944	Remote Similarity	NPD5181	Approved
0.6944	Remote Similarity	NPD5180	Approved
0.6944	Remote Similarity	NPD5179	Approved
0.6943	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD9540	Approved
0.6897	Remote Similarity	NPD5997	Discontinued
0.6894	Remote Similarity	NPD5024	Approved
0.6893	Remote Similarity	NPD3989	Phase 3
0.689	Remote Similarity	NPD7528	Approved
0.6886	Remote Similarity	NPD7072	Phase 2
0.6857	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3170	Approved
0.6854	Remote Similarity	NPD3990	Phase 3
0.6818	Remote Similarity	NPD1781	Discontinued
0.681	Remote Similarity	NPD6017	Discontinued
0.681	Remote Similarity	NPD5933	Phase 3
0.681	Remote Similarity	NPD5931	Phase 3
0.681	Remote Similarity	NPD5932	Phase 3
0.6809	Remote Similarity	NPD1065	Approved
0.6809	Remote Similarity	NPD1064	Approved
0.6805	Remote Similarity	NPD8630	Approved
0.6792	Remote Similarity	NPD5318	Discontinued
0.679	Remote Similarity	NPD2820	Phase 3
0.6772	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2010	Phase 3
0.6765	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1527	Phase 2
0.6748	Remote Similarity	NPD2435	Approved
0.6747	Remote Similarity	NPD5748	Phase 2
0.6747	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6489	Phase 3
0.6728	Remote Similarity	NPD2365	Approved
0.6723	Remote Similarity	NPD4091	Approved
0.6713	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6622	Phase 1
0.6703	Remote Similarity	NPD7569	Approved
0.6703	Remote Similarity	NPD7570	Approved
0.6688	Remote Similarity	NPD3240	Phase 2
0.6687	Remote Similarity	NPD2670	Approved
0.6685	Remote Similarity	NPD3995	Approved
0.6685	Remote Similarity	NPD3992	Approved
0.6685	Remote Similarity	NPD3994	Approved
0.6685	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4092	Approved
0.6685	Remote Similarity	NPD3991	Approved
0.6685	Remote Similarity	NPD3993	Approved
0.6685	Remote Similarity	NPD3996	Approved
0.6667	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5131	Approved
0.6667	Remote Similarity	NPD8263	Discontinued
0.6667	Remote Similarity	NPD2948	Discontinued
0.6667	Remote Similarity	NPD4116	Approved
0.6667	Remote Similarity	NPD4041	Approved
0.6667	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5042	Phase 1
0.6648	Remote Similarity	NPD5775	Approved
0.6648	Remote Similarity	NPD3997	Approved
0.6648	Remote Similarity	NPD3999	Approved
0.6648	Remote Similarity	NPD5774	Approved
0.6648	Remote Similarity	NPD3998	Approved
0.6647	Remote Similarity	NPD1663	Discontinued
0.6647	Remote Similarity	NPD6571	Approved
0.6647	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6570	Approved
0.6646	Remote Similarity	NPD1109	Approved
0.6646	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7254	Discontinued
0.6646	Remote Similarity	NPD1110	Approved
0.6645	Remote Similarity	NPD4176	Approved
0.6645	Remote Similarity	NPD4178	Approved
0.6629	Remote Similarity	NPD5104	Approved
0.6629	Remote Similarity	NPD6576	Discontinued
0.6628	Remote Similarity	NPD7244	Discontinued
0.6627	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5086	Approved
0.6627	Remote Similarity	NPD2790	Discontinued
0.6623	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7854	Phase 2
0.6609	Remote Similarity	NPD7036	Phase 3
0.6609	Remote Similarity	NPD7035	Approved
0.6601	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1175	Approved
0.6592	Remote Similarity	NPD5600	Discontinued
0.6587	Remote Similarity	NPD4682	Phase 2
0.6581	Remote Similarity	NPD1949	Approved
0.6581	Remote Similarity	NPD1950	Approved
0.6579	Remote Similarity	NPD1079	Discontinued
0.6575	Remote Similarity	NPD2999	Approved
0.6575	Remote Similarity	NPD1966	Approved
0.6575	Remote Similarity	NPD3001	Approved
0.6573	Remote Similarity	NPD3522	Approved
0.657	Remote Similarity	NPD4393	Approved
0.657	Remote Similarity	NPD7599	Phase 2
0.657	Remote Similarity	NPD33	Approved
0.6562	Remote Similarity	NPD2331	Discontinued
0.6556	Remote Similarity	NPD3077	Approved
0.6556	Remote Similarity	NPD3076	Approved
0.6556	Remote Similarity	NPD3078	Approved
0.6556	Remote Similarity	NPD3079	Approved
0.6556	Remote Similarity	NPD7881	Approved
0.655	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4500	Approved
0.6545	Remote Similarity	NPD4501	Approved
0.6541	Remote Similarity	NPD2949	Approved
0.6541	Remote Similarity	NPD2950	Approved
0.6534	Remote Similarity	NPD6457	Approved
0.6534	Remote Similarity	NPD2037	Approved
0.6532	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7600	Phase 2
0.6529	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6878	Phase 2
0.6519	Remote Similarity	NPD6879	Phase 2
0.6519	Remote Similarity	NPD1069	Approved
0.6519	Remote Similarity	NPD1619	Phase 3
0.6519	Remote Similarity	NPD1070	Approved
0.6516	Remote Similarity	NPD8128	Discontinued
0.6514	Remote Similarity	NPD2915	Discontinued
0.651	Remote Similarity	NPD1323	Discontinued
0.6506	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5060	Phase 1
0.6492	Remote Similarity	NPD6248	Phase 2
0.6492	Remote Similarity	NPD6249	Phase 2
0.6488	Remote Similarity	NPD4161	Discontinued
0.6474	Remote Similarity	NPD7572	Phase 2
0.6474	Remote Similarity	NPD2840	Approved
0.6471	Remote Similarity	NPD8240	Discontinued
0.6471	Remote Similarity	NPD3399	Approved
0.6463	Remote Similarity	NPD4461	Discontinued
0.6463	Remote Similarity	NPD2124	Approved
0.6456	Remote Similarity	NPD3424	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4365	Phase 2
0.6453	Remote Similarity	NPD7105	Phase 1
0.6452	Remote Similarity	NPD4334	Discontinued
0.6448	Remote Similarity	NPD8281	Discontinued
0.6444	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD3867	Phase 2
0.6442	Remote Similarity	NPD1626	Approved
0.644	Remote Similarity	NPD5071	Phase 2
0.6438	Remote Similarity	NPD7633	Discontinued
0.6438	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4311	Approved
0.6436	Remote Similarity	NPD6200	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5444	Phase 1
0.6429	Remote Similarity	NPD7088	Discontinued
0.6429	Remote Similarity	NPD4330	Approved
0.6429	Remote Similarity	NPD4329	Approved
0.6424	Remote Similarity	NPD5990	Approved
0.6424	Remote Similarity	NPD5991	Approved
0.6424	Remote Similarity	NPD2923	Approved
0.6417	Remote Similarity	NPD4499	Approved
0.6417	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4783	Approved
0.6415	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4781	Approved
0.641	Remote Similarity	NPD2962	Approved
0.641	Remote Similarity	NPD2961	Approved
0.6409	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3792	Approved
0.6409	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6185	Discontinued
0.6398	Remote Similarity	NPD8103	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