NPASS Compound

Structure

NPC474641 OpenBabel07101719522D 32 34 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0158 -3.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6888 -3.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7570 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4300 -2.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9817 -3.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.2406 -4.8978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2575 -1.3912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 15 2 0 0 0 0 5 15 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 23 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 30 1 0 0 0 0 14 31 1 0 0 0 0 16 24 2 0 0 0 0 17 14 1 1 0 0 0 17 19 1 0 0 0 0 17 32 1 0 0 0 0 18 25 2 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 21 22 1 0 0 0 0 21 28 1 6 0 0 0 22 30 1 1 0 0 0 22 32 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.16
Volume:	438.715
LogP:	0.945
LogD:	0.562
LogS:	-3.254
# Rotatable Bonds:	9
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	4.155
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.139
MDCK Permeability:	1.3312349437910598e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.089
Human Intestinal Absorption (HIA):	0.874
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	82.03392028808594%
Volume Distribution (VD):	0.765
Pgp-substrate:	13.849000930786133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.277
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	2.261
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.139
Rat Oral Acute Toxicity:	0.328
Maximum Recommended Daily Dose:	0.107
Skin Sensitization:	0.953
Carcinogencity:	0.409
Eye Corrosion:	0.004
Eye Irritation:	0.513
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC474641

Natural Product ID:	NPC474641
*Common Name:**	Eutigoside C
IUPAC Name:	[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (E)-3-phenylprop-2-enoate
Synonyms:	Eutigoside C
Standard InCHIKey:	QOMDZDCUSAVCSJ-LPIGZASCSA-N
Standard InCHI:	InChI=1S/C23H26O9/c24-16-8-10-23(29,11-9-16)12-13-30-22-21(28)20(27)19(26)17(32-22)14-31-18(25)7-6-15-4-2-1-3-5-15/h1-11,17,19-22,26-29H,12-14H2/b7-6+/t17-,19-,20+,21-,22-/m1/s1
SMILES:	C1=CC=C(C=C1)C=CC(=O)OCC2C(C(C(C(O2)OCCC3(C=CC(=O)C=C3)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477903
PubChem CID:	9981001
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO33318	eurya tigang	Species	Pentaphylacaceae	Eukaryota	leaves	n.a.	n.a.	PMID[1431944]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT550	Cell Line	T-24	Homo sapiens	IC50	=	29.3	ug.mL-1	PMID[474934]
NPT27	Others	Unspecified		IC50	=	12.6	ug.mL-1	PMID[474934]

☑ 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 NPC474641 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	222
0.1-0.2	1022
0.2-0.3	2589
0.3-0.4	7544
0.4-0.5	12373
0.5-0.6	15182
0.6-0.7	3234
0.7-0.8	461
0.8-0.85	57
0.85-0.9	10
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC184633
0.9439	High Similarity	NPC470825
0.9346	High Similarity	NPC43584
0.8868	High Similarity	NPC469527
0.8824	High Similarity	NPC252114
0.8793	High Similarity	NPC229600
0.8673	High Similarity	NPC29607
0.8655	High Similarity	NPC244454
0.8644	High Similarity	NPC141970
0.8644	High Similarity	NPC140561
0.8512	High Similarity	NPC267733
0.8512	High Similarity	NPC276047
0.85	High Similarity	NPC145287
0.8487	Intermediate Similarity	NPC52097
0.8443	Intermediate Similarity	NPC106677
0.843	Intermediate Similarity	NPC83218
0.843	Intermediate Similarity	NPC126991
0.8403	Intermediate Similarity	NPC11724
0.8393	Intermediate Similarity	NPC474148
0.8393	Intermediate Similarity	NPC276061
0.8361	Intermediate Similarity	NPC471157
0.8347	Intermediate Similarity	NPC162925
0.8347	Intermediate Similarity	NPC87153
0.8319	Intermediate Similarity	NPC476872
0.8319	Intermediate Similarity	NPC30563
0.8319	Intermediate Similarity	NPC264784
0.8306	Intermediate Similarity	NPC253595
0.8306	Intermediate Similarity	NPC11025
0.8293	Intermediate Similarity	NPC175333
0.8293	Intermediate Similarity	NPC231627
0.8293	Intermediate Similarity	NPC288416
0.8279	Intermediate Similarity	NPC28069
0.8279	Intermediate Similarity	NPC77651
0.8226	Intermediate Similarity	NPC237182
0.8226	Intermediate Similarity	NPC225307
0.8226	Intermediate Similarity	NPC226101
0.8211	Intermediate Similarity	NPC10883
0.8211	Intermediate Similarity	NPC198918
0.8211	Intermediate Similarity	NPC63404
0.8211	Intermediate Similarity	NPC204214
0.8211	Intermediate Similarity	NPC10121
0.8211	Intermediate Similarity	NPC92283
0.8211	Intermediate Similarity	NPC124878
0.8211	Intermediate Similarity	NPC290276
0.8211	Intermediate Similarity	NPC231888
0.8211	Intermediate Similarity	NPC114096
0.8211	Intermediate Similarity	NPC35338
0.8198	Intermediate Similarity	NPC37714
0.8198	Intermediate Similarity	NPC152384
0.8175	Intermediate Similarity	NPC478255
0.8151	Intermediate Similarity	NPC476096
0.8145	Intermediate Similarity	NPC471881
0.8145	Intermediate Similarity	NPC471882
0.8145	Intermediate Similarity	NPC156692
0.8145	Intermediate Similarity	NPC35288
0.8145	Intermediate Similarity	NPC148026
0.8145	Intermediate Similarity	NPC471025
0.8145	Intermediate Similarity	NPC173150
0.8145	Intermediate Similarity	NPC45224
0.8108	Intermediate Similarity	NPC47286
0.8095	Intermediate Similarity	NPC289415
0.8095	Intermediate Similarity	NPC319995
0.8095	Intermediate Similarity	NPC17567
0.808	Intermediate Similarity	NPC471024
0.808	Intermediate Similarity	NPC301857
0.8065	Intermediate Similarity	NPC147032
0.8047	Intermediate Similarity	NPC470143
0.8047	Intermediate Similarity	NPC322503
0.8031	Intermediate Similarity	NPC254819
0.8031	Intermediate Similarity	NPC235294
0.8031	Intermediate Similarity	NPC246869
0.8031	Intermediate Similarity	NPC138777
0.8031	Intermediate Similarity	NPC225384
0.8031	Intermediate Similarity	NPC46137
0.8016	Intermediate Similarity	NPC477293
0.8016	Intermediate Similarity	NPC477294
0.8016	Intermediate Similarity	NPC229784
0.7982	Intermediate Similarity	NPC262826
0.7969	Intermediate Similarity	NPC473924
0.7969	Intermediate Similarity	NPC473285
0.7937	Intermediate Similarity	NPC146540
0.7937	Intermediate Similarity	NPC232880
0.7931	Intermediate Similarity	NPC234376
0.792	Intermediate Similarity	NPC61181
0.7907	Intermediate Similarity	NPC254398
0.7907	Intermediate Similarity	NPC28637
0.7903	Intermediate Similarity	NPC57607
0.7891	Intermediate Similarity	NPC281798
0.7891	Intermediate Similarity	NPC219677
0.7874	Intermediate Similarity	NPC295970
0.7863	Intermediate Similarity	NPC472132
0.7863	Intermediate Similarity	NPC265002
0.7857	Intermediate Similarity	NPC140750
0.7857	Intermediate Similarity	NPC230331
0.7857	Intermediate Similarity	NPC476873
0.7857	Intermediate Similarity	NPC103533
0.7846	Intermediate Similarity	NPC886
0.7846	Intermediate Similarity	NPC34293
0.7846	Intermediate Similarity	NPC287597
0.7833	Intermediate Similarity	NPC216605
0.7833	Intermediate Similarity	NPC266389
0.7833	Intermediate Similarity	NPC122245
0.7823	Intermediate Similarity	NPC473881
0.7823	Intermediate Similarity	NPC470815
0.7812	Intermediate Similarity	NPC470079
0.7807	Intermediate Similarity	NPC136962
0.7807	Intermediate Similarity	NPC37115
0.7805	Intermediate Similarity	NPC475328
0.7788	Intermediate Similarity	NPC280616
0.7788	Intermediate Similarity	NPC171831
0.7788	Intermediate Similarity	NPC242913
0.7788	Intermediate Similarity	NPC148060
0.7786	Intermediate Similarity	NPC476870
0.7786	Intermediate Similarity	NPC263829
0.7778	Intermediate Similarity	NPC471026
0.7757	Intermediate Similarity	NPC472319
0.7744	Intermediate Similarity	NPC49597
0.7744	Intermediate Similarity	NPC171134
0.7744	Intermediate Similarity	NPC328273
0.7744	Intermediate Similarity	NPC321638
0.7744	Intermediate Similarity	NPC321184
0.7734	Intermediate Similarity	NPC27712
0.7731	Intermediate Similarity	NPC313193
0.7727	Intermediate Similarity	NPC166180
0.7727	Intermediate Similarity	NPC471345
0.771	Intermediate Similarity	NPC471883
0.771	Intermediate Similarity	NPC169398
0.7669	Intermediate Similarity	NPC78363
0.7669	Intermediate Similarity	NPC476376
0.7669	Intermediate Similarity	NPC260425
0.7652	Intermediate Similarity	NPC320259
0.7652	Intermediate Similarity	NPC185778
0.7652	Intermediate Similarity	NPC475203
0.7652	Intermediate Similarity	NPC474376
0.7652	Intermediate Similarity	NPC472316
0.7652	Intermediate Similarity	NPC472315
0.7647	Intermediate Similarity	NPC120217
0.763	Intermediate Similarity	NPC46644
0.7627	Intermediate Similarity	NPC185840
0.7612	Intermediate Similarity	NPC81515
0.7612	Intermediate Similarity	NPC64141
0.7612	Intermediate Similarity	NPC472350
0.7612	Intermediate Similarity	NPC68092
0.7612	Intermediate Similarity	NPC197316
0.7612	Intermediate Similarity	NPC31745
0.7612	Intermediate Similarity	NPC476383
0.7612	Intermediate Similarity	NPC220936
0.7612	Intermediate Similarity	NPC205195
0.7612	Intermediate Similarity	NPC89105
0.7603	Intermediate Similarity	NPC470820
0.7603	Intermediate Similarity	NPC175771
0.7594	Intermediate Similarity	NPC37468
0.7594	Intermediate Similarity	NPC157554
0.7594	Intermediate Similarity	NPC470572
0.7574	Intermediate Similarity	NPC148080
0.7574	Intermediate Similarity	NPC469623
0.7574	Intermediate Similarity	NPC284957
0.7559	Intermediate Similarity	NPC45821
0.7556	Intermediate Similarity	NPC202700
0.754	Intermediate Similarity	NPC472373
0.7538	Intermediate Similarity	NPC305162
0.7537	Intermediate Similarity	NPC475195
0.7537	Intermediate Similarity	NPC101686
0.7537	Intermediate Similarity	NPC65262
0.7537	Intermediate Similarity	NPC469364
0.7519	Intermediate Similarity	NPC93632
0.7518	Intermediate Similarity	NPC263397
0.7518	Intermediate Similarity	NPC88754
0.7518	Intermediate Similarity	NPC478250
0.7518	Intermediate Similarity	NPC116104
0.7518	Intermediate Similarity	NPC40305
0.7518	Intermediate Similarity	NPC105005
0.7518	Intermediate Similarity	NPC204644
0.7518	Intermediate Similarity	NPC302286
0.7518	Intermediate Similarity	NPC237872
0.75	Intermediate Similarity	NPC476442
0.75	Intermediate Similarity	NPC38420
0.75	Intermediate Similarity	NPC136608
0.75	Intermediate Similarity	NPC476971
0.75	Intermediate Similarity	NPC476385
0.75	Intermediate Similarity	NPC475513
0.75	Intermediate Similarity	NPC476972
0.75	Intermediate Similarity	NPC473755
0.75	Intermediate Similarity	NPC186406
0.75	Intermediate Similarity	NPC134405
0.75	Intermediate Similarity	NPC476377
0.75	Intermediate Similarity	NPC215512
0.75	Intermediate Similarity	NPC114116
0.75	Intermediate Similarity	NPC47471
0.7481	Intermediate Similarity	NPC220942
0.7481	Intermediate Similarity	NPC100389
0.7481	Intermediate Similarity	NPC226005
0.748	Intermediate Similarity	NPC471758
0.7477	Intermediate Similarity	NPC30361
0.7464	Intermediate Similarity	NPC300894
0.7464	Intermediate Similarity	NPC296954
0.7464	Intermediate Similarity	NPC141455
0.7464	Intermediate Similarity	NPC110063
0.7464	Intermediate Similarity	NPC251062
0.7464	Intermediate Similarity	NPC63304

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 NPC474641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	698
0.2-0.3	1581
0.3-0.4	3384
0.4-0.5	2341
0.5-0.6	891
0.6-0.7	57
0.7-0.8	8
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
0.7627	Intermediate Similarity	NPD969	Suspended
0.7612	Intermediate Similarity	NPD7266	Discontinued
0.7557	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD689	Discontinued
0.7244	Intermediate Similarity	NPD1091	Approved
0.7241	Intermediate Similarity	NPD6647	Phase 2
0.7222	Intermediate Similarity	NPD5126	Approved
0.7222	Intermediate Similarity	NPD5125	Phase 3
0.7119	Intermediate Similarity	NPD5048	Discontinued
0.6966	Remote Similarity	NPD1653	Approved
0.6909	Remote Similarity	NPD1282	Approved
0.6875	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6010	Discontinued
0.6783	Remote Similarity	NPD6190	Approved
0.6772	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6685	Approved
0.6613	Remote Similarity	NPD2067	Discontinued
0.6612	Remote Similarity	NPD5909	Discontinued
0.661	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD9716	Approved
0.6569	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7798	Approved
0.6552	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5765	Approved
0.6508	Remote Similarity	NPD6912	Phase 3
0.6484	Remote Similarity	NPD2629	Approved
0.6484	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD9495	Approved
0.6471	Remote Similarity	NPD5926	Approved
0.6452	Remote Similarity	NPD1358	Approved
0.6438	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD1652	Phase 2
0.6412	Remote Similarity	NPD7741	Discontinued
0.6405	Remote Similarity	NPD8455	Phase 2
0.6396	Remote Similarity	NPD3971	Phase 1
0.6383	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5124	Phase 1
0.6375	Remote Similarity	NPD7799	Discontinued
0.6364	Remote Similarity	NPD7503	Approved
0.6333	Remote Similarity	NPD5403	Approved
0.632	Remote Similarity	NPD6686	Approved
0.6319	Remote Similarity	NPD7685	Pre-registration
0.6294	Remote Similarity	NPD7097	Phase 1
0.6288	Remote Similarity	NPD9545	Approved
0.6281	Remote Similarity	NPD1238	Approved
0.627	Remote Similarity	NPD2182	Approved
0.6268	Remote Similarity	NPD4340	Discontinued
0.6259	Remote Similarity	NPD4628	Phase 3
0.6242	Remote Similarity	NPD8312	Approved
0.6242	Remote Similarity	NPD8313	Approved
0.624	Remote Similarity	NPD3134	Approved
0.622	Remote Similarity	NPD6559	Discontinued
0.621	Remote Similarity	NPD1237	Approved
0.6209	Remote Similarity	NPD4380	Phase 2
0.62	Remote Similarity	NPD5401	Approved
0.6182	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5058	Phase 3
0.6173	Remote Similarity	NPD3818	Discontinued
0.6172	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5402	Approved
0.6154	Remote Similarity	NPD7838	Discovery
0.6149	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2575	Approved
0.6148	Remote Similarity	NPD2066	Phase 3
0.6142	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD7033	Discontinued
0.6135	Remote Similarity	NPD7054	Approved
0.6135	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6233	Phase 2
0.6121	Remote Similarity	NPD8368	Discontinued
0.6098	Remote Similarity	NPD7472	Approved
0.6098	Remote Similarity	NPD7074	Phase 3
0.6087	Remote Similarity	NPD3225	Approved
0.6082	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD7075	Discontinued
0.6074	Remote Similarity	NPD5305	Approved
0.6074	Remote Similarity	NPD5306	Approved
0.6074	Remote Similarity	NPD3751	Discontinued
0.6067	Remote Similarity	NPD7236	Approved
0.6063	Remote Similarity	NPD9532	Phase 3
0.6063	Remote Similarity	NPD290	Approved
0.6061	Remote Similarity	NPD6797	Phase 2
0.6058	Remote Similarity	NPD6637	Approved
0.6056	Remote Similarity	NPD3764	Approved
0.6043	Remote Similarity	NPD2159	Approved
0.6043	Remote Similarity	NPD2627	Approved
0.6043	Remote Similarity	NPD2626	Approved
0.6043	Remote Similarity	NPD2628	Approved
0.6043	Remote Similarity	NPD2625	Approved
0.6043	Remote Similarity	NPD2160	Approved
0.6042	Remote Similarity	NPD230	Phase 1
0.6029	Remote Similarity	NPD4136	Approved
0.6029	Remote Similarity	NPD3496	Discontinued
0.6029	Remote Similarity	NPD4106	Approved
0.6029	Remote Similarity	NPD4135	Approved
0.6028	Remote Similarity	NPD4617	Approved
0.6028	Remote Similarity	NPD5203	Approved
0.6028	Remote Similarity	NPD4620	Approved
0.6028	Remote Similarity	NPD5201	Approved
0.6026	Remote Similarity	NPD6801	Discontinued
0.6026	Remote Similarity	NPD37	Approved
0.6024	Remote Similarity	NPD7251	Discontinued
0.6017	Remote Similarity	NPD9256	Approved
0.6017	Remote Similarity	NPD9258	Approved
0.6015	Remote Similarity	NPD5292	Approved
0.6015	Remote Similarity	NPD5291	Approved
0.6014	Remote Similarity	NPD4404	Approved
0.6014	Remote Similarity	NPD2424	Discontinued
0.6014	Remote Similarity	NPD7876	Discontinued
0.6014	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD4965	Approved
0.6013	Remote Similarity	NPD4967	Phase 2
0.6013	Remote Similarity	NPD4966	Approved
0.6013	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD8407	Phase 2
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.6	Remote Similarity	NPD1357	Approved
0.6	Remote Similarity	NPD6653	Approved
0.6	Remote Similarity	NPD9294	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD5647	Approved
0.5988	Remote Similarity	NPD7808	Phase 3
0.5987	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD3027	Phase 3
0.5985	Remote Similarity	NPD4806	Approved
0.5985	Remote Similarity	NPD4807	Approved
0.5985	Remote Similarity	NPD422	Phase 1
0.5976	Remote Similarity	NPD7228	Approved
0.5976	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD7239	Suspended
0.5973	Remote Similarity	NPD6674	Discontinued
0.5973	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD1613	Approved
0.5954	Remote Similarity	NPD7094	Approved
0.5954	Remote Similarity	NPD7843	Approved
0.5954	Remote Similarity	NPD6858	Approved
0.5952	Remote Similarity	NPD164	Approved
0.5944	Remote Similarity	NPD6798	Discontinued
0.5938	Remote Similarity	NPD6234	Discontinued
0.5938	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD8166	Discontinued
0.5931	Remote Similarity	NPD1933	Approved
0.5929	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD226	Approved
0.5921	Remote Similarity	NPD6799	Approved
0.592	Remote Similarity	NPD1932	Approved
0.5915	Remote Similarity	NPD2613	Approved
0.5915	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4793	Discontinued
0.5896	Remote Similarity	NPD7328	Approved
0.5896	Remote Similarity	NPD9493	Approved
0.5896	Remote Similarity	NPD7327	Approved
0.5891	Remote Similarity	NPD2684	Approved
0.5882	Remote Similarity	NPD3672	Approved
0.5882	Remote Similarity	NPD4105	Approved
0.5882	Remote Similarity	NPD3673	Approved
0.5882	Remote Similarity	NPD4102	Approved
0.5882	Remote Similarity	NPD46	Approved
0.5882	Remote Similarity	NPD6698	Approved
0.5874	Remote Similarity	NPD7008	Discontinued
0.5873	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD1930	Approved
0.5873	Remote Similarity	NPD1929	Approved
0.5872	Remote Similarity	NPD8361	Approved
0.5872	Remote Similarity	NPD8360	Approved
0.587	Remote Similarity	NPD3705	Approved
0.5868	Remote Similarity	NPD1202	Approved
0.5862	Remote Similarity	NPD5119	Approved
0.5862	Remote Similarity	NPD5121	Approved
0.5862	Remote Similarity	NPD6309	Approved
0.5862	Remote Similarity	NPD5120	Approved
0.5862	Remote Similarity	NPD6310	Approved
0.5862	Remote Similarity	NPD6311	Approved
0.586	Remote Similarity	NPD7411	Suspended
0.5857	Remote Similarity	NPD5667	Approved
0.5852	Remote Similarity	NPD7516	Approved
0.585	Remote Similarity	NPD4536	Approved
0.585	Remote Similarity	NPD4538	Approved
0.585	Remote Similarity	NPD41	Approved
0.585	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.585	Remote Similarity	NPD5886	Approved
0.5848	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD8150	Discontinued
0.5847	Remote Similarity	NPD531	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data