NPASS Compound

Structure

NPC252114 OpenBabel07101719252D 33 35 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 6.0622 -3.5000 0.0000 O 0 0 0 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 4 1 0 0 0 0 1 14 2 0 0 0 0 2 5 2 0 0 0 0 2 14 1 0 0 0 0 3 6 2 0 0 0 0 3 14 1 0 0 0 0 4 15 2 0 0 0 0 5 15 1 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 23 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 31 1 0 0 0 0 13 32 1 0 0 0 0 15 24 1 0 0 0 0 16 25 2 0 0 0 0 17 13 1 1 0 0 0 17 19 1 0 0 0 0 17 33 1 0 0 0 0 18 26 2 0 0 0 0 18 32 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 31 1 1 0 0 0 22 33 1 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.15
Volume:	447.505
LogP:	0.912
LogD:	0.253
LogS:	-2.153
# Rotatable Bonds:	9
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	4.246
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:	-5.78
MDCK Permeability:	1.260886710952036e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.091
Human Intestinal Absorption (HIA):	0.912
20% Bioavailability (F20%):	0.533
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	89.79830932617188%
Volume Distribution (VD):	0.917
Pgp-substrate:	5.535598278045654%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	2.159
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.154
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.542
Maximum Recommended Daily Dose:	0.426
Skin Sensitization:	0.961
Carcinogencity:	0.371
Eye Corrosion:	0.003
Eye Irritation:	0.066
Respiratory Toxicity:	0.795

Download Data

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

Natural Product: NPC252114

Natural Product ID:	NPC252114
*Common Name:**	Eutigoside B
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-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	Neocalceolarioside D
Standard InCHIKey:	IWMPEDMJSGFILP-FPULVWICSA-N
Standard InCHI:	InChI=1S/C23H26O10/c24-15-4-1-14(2-5-15)3-6-18(26)32-13-17-19(27)20(28)21(29)22(33-17)31-12-11-23(30)9-7-16(25)8-10-23/h1-10,17,19-22,24,27-30H,11-13H2/b6-3+/t17-,19-,20+,21-,22-/m1/s1
SMILES:	O=C(/C=C/c1ccc(cc1)O)OC[C@H]1O[C@@H](OCCC2(O)C=CC(=O)C=C2)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477535
PubChem CID:	10367075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric 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]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540981]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	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
ED50	1
IC50	2

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT550	Cell Line	T-24	Homo sapiens	IC50	=	31.9	ug.mL-1	PMID[532757]
NPT27	Others	Unspecified		IC50	=	9.4	ug.mL-1	PMID[532757]
NPT1	Others	Radical scavenging activity		ED50	>	100.0	uM	PMID[532758]

☑ 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 NPC252114 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	281
0.1-0.2	1242
0.2-0.3	3228
0.3-0.4	8050
0.4-0.5	10474
0.5-0.6	7891
0.6-0.7	9715
0.7-0.8	1524
0.8-0.85	204
0.85-0.9	56
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC52097
0.959	High Similarity	NPC106677
0.9587	High Similarity	NPC83218
0.9587	High Similarity	NPC126991
0.958	High Similarity	NPC11724
0.9508	High Similarity	NPC471157
0.9496	High Similarity	NPC476872
0.9435	High Similarity	NPC253595
0.9431	High Similarity	NPC288416
0.9355	High Similarity	NPC225307
0.9286	High Similarity	NPC478255
0.9274	High Similarity	NPC156692
0.9274	High Similarity	NPC471882
0.9274	High Similarity	NPC173150
0.9274	High Similarity	NPC35288
0.9274	High Similarity	NPC45224
0.9274	High Similarity	NPC471881
0.9134	High Similarity	NPC138777
0.9134	High Similarity	NPC235294
0.9134	High Similarity	NPC46137
0.9134	High Similarity	NPC225384
0.9134	High Similarity	NPC246869
0.9134	High Similarity	NPC254819
0.9127	High Similarity	NPC477294
0.9127	High Similarity	NPC477293
0.9127	High Similarity	NPC229784
0.9062	High Similarity	NPC473924
0.9062	High Similarity	NPC473285
0.9048	High Similarity	NPC232880
0.904	High Similarity	NPC61181
0.8992	High Similarity	NPC28637
0.8992	High Similarity	NPC254398
0.8984	High Similarity	NPC281798
0.8984	High Similarity	NPC219677
0.8968	High Similarity	NPC476873
0.8968	High Similarity	NPC103533
0.8931	High Similarity	NPC472132
0.8923	High Similarity	NPC287597
0.8923	High Similarity	NPC34293
0.8923	High Similarity	NPC886
0.8908	High Similarity	NPC313193
0.8855	High Similarity	NPC476870
0.8855	High Similarity	NPC263829
0.8828	High Similarity	NPC295970
0.8824	High Similarity	NPC474641
0.8797	High Similarity	NPC321184
0.8797	High Similarity	NPC171134
0.8797	High Similarity	NPC49597
0.8797	High Similarity	NPC321638
0.8797	High Similarity	NPC328273
0.8788	High Similarity	NPC166180
0.8788	High Similarity	NPC471345
0.8779	High Similarity	NPC169398
0.8779	High Similarity	NPC471883
0.876	High Similarity	NPC175771
0.8722	High Similarity	NPC78363
0.8722	High Similarity	NPC476376
0.8722	High Similarity	NPC260425
0.8672	High Similarity	NPC140750
0.8667	High Similarity	NPC46644
0.8657	High Similarity	NPC205195
0.8657	High Similarity	NPC31745
0.8657	High Similarity	NPC81515
0.8657	High Similarity	NPC220936
0.8657	High Similarity	NPC472350
0.8657	High Similarity	NPC476383
0.8657	High Similarity	NPC64141
0.8657	High Similarity	NPC68092
0.8657	High Similarity	NPC197316
0.8657	High Similarity	NPC89105
0.8647	High Similarity	NPC470572
0.8647	High Similarity	NPC157554
0.8615	High Similarity	NPC470079
0.8607	High Similarity	NPC148055
0.8605	High Similarity	NPC146540
0.8603	High Similarity	NPC469623
0.8603	High Similarity	NPC148080
0.8595	High Similarity	NPC157338
0.8593	High Similarity	NPC202700
0.8582	High Similarity	NPC469364
0.8582	High Similarity	NPC65262
0.8582	High Similarity	NPC101686
0.8561	High Similarity	NPC114116
0.856	High Similarity	NPC201402
0.856	High Similarity	NPC476448
0.856	High Similarity	NPC160854
0.856	High Similarity	NPC469703
0.856	High Similarity	NPC476445
0.856	High Similarity	NPC469704
0.856	High Similarity	NPC469548
0.854	High Similarity	NPC105005
0.854	High Similarity	NPC204644
0.854	High Similarity	NPC478250
0.854	High Similarity	NPC40305
0.8538	High Similarity	NPC469549
0.8529	High Similarity	NPC47471
0.8529	High Similarity	NPC186406
0.8529	High Similarity	NPC134405
0.8529	High Similarity	NPC476385
0.8529	High Similarity	NPC476377
0.8519	High Similarity	NPC220942
0.8519	High Similarity	NPC226005
0.8519	High Similarity	NPC100389
0.8507	High Similarity	NPC37468
0.8507	High Similarity	NPC186418
0.8504	High Similarity	NPC232454
0.8504	High Similarity	NPC178449
0.8504	High Similarity	NPC470907
0.8492	Intermediate Similarity	NPC55608
0.8492	Intermediate Similarity	NPC469686
0.848	Intermediate Similarity	NPC282409
0.848	Intermediate Similarity	NPC469702
0.8478	Intermediate Similarity	NPC63304
0.8478	Intermediate Similarity	NPC251062
0.8478	Intermediate Similarity	NPC110063
0.8478	Intermediate Similarity	NPC296954
0.8478	Intermediate Similarity	NPC300894
0.8478	Intermediate Similarity	NPC141455
0.8478	Intermediate Similarity	NPC196063
0.8478	Intermediate Similarity	NPC184464
0.8467	Intermediate Similarity	NPC145319
0.8467	Intermediate Similarity	NPC157816
0.8467	Intermediate Similarity	NPC265648
0.8467	Intermediate Similarity	NPC140502
0.8467	Intermediate Similarity	NPC222433
0.8456	Intermediate Similarity	NPC473799
0.8456	Intermediate Similarity	NPC475530
0.8433	Intermediate Similarity	NPC320259
0.8433	Intermediate Similarity	NPC185778
0.8425	Intermediate Similarity	NPC471067
0.8417	Intermediate Similarity	NPC475528
0.8413	Intermediate Similarity	NPC229600
0.8406	Intermediate Similarity	NPC264632
0.8406	Intermediate Similarity	NPC88754
0.8406	Intermediate Similarity	NPC76406
0.8406	Intermediate Similarity	NPC476380
0.8406	Intermediate Similarity	NPC476375
0.8406	Intermediate Similarity	NPC298257
0.8406	Intermediate Similarity	NPC293154
0.8406	Intermediate Similarity	NPC96795
0.8406	Intermediate Similarity	NPC476378
0.8406	Intermediate Similarity	NPC205864
0.8406	Intermediate Similarity	NPC112
0.8406	Intermediate Similarity	NPC478239
0.8406	Intermediate Similarity	NPC476397
0.8406	Intermediate Similarity	NPC175214
0.8406	Intermediate Similarity	NPC116104
0.8406	Intermediate Similarity	NPC237872
0.8406	Intermediate Similarity	NPC263397
0.8406	Intermediate Similarity	NPC247032
0.8406	Intermediate Similarity	NPC302286
0.8406	Intermediate Similarity	NPC476384
0.8406	Intermediate Similarity	NPC119537
0.8406	Intermediate Similarity	NPC476381
0.8406	Intermediate Similarity	NPC269141
0.8403	Intermediate Similarity	NPC184633
0.8394	Intermediate Similarity	NPC7518
0.8394	Intermediate Similarity	NPC154262
0.8394	Intermediate Similarity	NPC476442
0.8394	Intermediate Similarity	NPC215512
0.8394	Intermediate Similarity	NPC159387
0.8394	Intermediate Similarity	NPC137501
0.837	Intermediate Similarity	NPC103409
0.8357	Intermediate Similarity	NPC119773
0.8357	Intermediate Similarity	NPC229505
0.8357	Intermediate Similarity	NPC475539
0.8357	Intermediate Similarity	NPC291153
0.8357	Intermediate Similarity	NPC143246
0.8357	Intermediate Similarity	NPC474268
0.8347	Intermediate Similarity	NPC470825
0.8345	Intermediate Similarity	NPC476867
0.8345	Intermediate Similarity	NPC296659
0.8345	Intermediate Similarity	NPC202391
0.8345	Intermediate Similarity	NPC232228
0.8345	Intermediate Similarity	NPC292443
0.8345	Intermediate Similarity	NPC77922
0.8345	Intermediate Similarity	NPC64195
0.8345	Intermediate Similarity	NPC473281
0.8333	Intermediate Similarity	NPC469705
0.8333	Intermediate Similarity	NPC17968
0.8333	Intermediate Similarity	NPC470122
0.8333	Intermediate Similarity	NPC296643
0.8321	Intermediate Similarity	NPC158673
0.831	Intermediate Similarity	NPC478242
0.8309	Intermediate Similarity	NPC124149
0.8298	Intermediate Similarity	NPC18789
0.8295	Intermediate Similarity	NPC287429
0.8286	Intermediate Similarity	NPC262182
0.8286	Intermediate Similarity	NPC34587
0.8286	Intermediate Similarity	NPC476869
0.8286	Intermediate Similarity	NPC476866
0.8286	Intermediate Similarity	NPC252292
0.8286	Intermediate Similarity	NPC476868
0.8286	Intermediate Similarity	NPC100998
0.8286	Intermediate Similarity	NPC83743
0.8286	Intermediate Similarity	NPC34927
0.8286	Intermediate Similarity	NPC216819
0.8286	Intermediate Similarity	NPC476864
0.8286	Intermediate Similarity	NPC287615
0.8286	Intermediate Similarity	NPC476382

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 NPC252114 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	766
0.2-0.3	1627
0.3-0.4	3024
0.4-0.5	1947
0.5-0.6	1213
0.6-0.7	329
0.7-0.8	9
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8657	High Similarity	NPD7266	Discontinued
0.7931	Intermediate Similarity	NPD1653	Approved
0.7923	Intermediate Similarity	NPD1091	Approved
0.7762	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD969	Suspended
0.744	Intermediate Similarity	NPD1358	Approved
0.7394	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9545	Approved
0.726	Intermediate Similarity	NPD1652	Phase 2
0.7222	Intermediate Similarity	NPD3134	Approved
0.7208	Intermediate Similarity	NPD8455	Phase 2
0.7178	Intermediate Similarity	NPD7685	Pre-registration
0.7153	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5124	Phase 1
0.7133	Intermediate Similarity	NPD4340	Discontinued
0.7124	Intermediate Similarity	NPD4380	Phase 2
0.7095	Intermediate Similarity	NPD4628	Phase 3
0.7073	Intermediate Similarity	NPD6559	Discontinued
0.7042	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD3818	Discontinued
0.703	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD422	Phase 1
0.7	Intermediate Similarity	NPD5058	Phase 3
0.6994	Remote Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6233	Phase 2
0.6985	Remote Similarity	NPD5126	Approved
0.6985	Remote Similarity	NPD5125	Phase 3
0.6972	Remote Similarity	NPD3027	Phase 3
0.6962	Remote Similarity	NPD7075	Discontinued
0.6954	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7472	Approved
0.6951	Remote Similarity	NPD7074	Phase 3
0.6944	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1613	Approved
0.6928	Remote Similarity	NPD5403	Approved
0.6912	Remote Similarity	NPD1357	Approved
0.6909	Remote Similarity	NPD6797	Phase 2
0.6899	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7843	Approved
0.6886	Remote Similarity	NPD8312	Approved
0.6886	Remote Similarity	NPD8313	Approved
0.6867	Remote Similarity	NPD8166	Discontinued
0.6867	Remote Similarity	NPD7251	Discontinued
0.6867	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2424	Discontinued
0.6846	Remote Similarity	NPD2684	Approved
0.6829	Remote Similarity	NPD7228	Approved
0.6828	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7808	Phase 3
0.6815	Remote Similarity	NPD37	Approved
0.6815	Remote Similarity	NPD6801	Discontinued
0.6813	Remote Similarity	NPD6234	Discontinued
0.6806	Remote Similarity	NPD6798	Discontinued
0.6805	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5401	Approved
0.6792	Remote Similarity	NPD4967	Phase 2
0.6792	Remote Similarity	NPD4966	Approved
0.6792	Remote Similarity	NPD4965	Approved
0.6772	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD290	Approved
0.6769	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3705	Approved
0.6757	Remote Similarity	NPD7033	Discontinued
0.6755	Remote Similarity	NPD3750	Approved
0.6741	Remote Similarity	NPD7157	Approved
0.6738	Remote Similarity	NPD3225	Approved
0.6733	Remote Similarity	NPD1549	Phase 2
0.6732	Remote Similarity	NPD6799	Approved
0.673	Remote Similarity	NPD5402	Approved
0.6727	Remote Similarity	NPD3751	Discontinued
0.6715	Remote Similarity	NPD1548	Phase 1
0.6713	Remote Similarity	NPD2861	Phase 2
0.6712	Remote Similarity	NPD4060	Phase 1
0.671	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2934	Approved
0.6694	Remote Similarity	NPD2933	Approved
0.6694	Remote Similarity	NPD689	Discontinued
0.6691	Remote Similarity	NPD9493	Approved
0.6691	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3496	Discontinued
0.669	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4536	Approved
0.6689	Remote Similarity	NPD6674	Discontinued
0.6689	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4538	Approved
0.6688	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7411	Suspended
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5960	Phase 3
0.6644	Remote Similarity	NPD4062	Phase 3
0.6644	Remote Similarity	NPD5588	Approved
0.6643	Remote Similarity	NPD1610	Phase 2
0.6643	Remote Similarity	NPD5647	Approved
0.6642	Remote Similarity	NPD5536	Phase 2
0.6642	Remote Similarity	NPD5535	Approved
0.664	Remote Similarity	NPD2860	Approved
0.664	Remote Similarity	NPD2859	Approved
0.6624	Remote Similarity	NPD7458	Discontinued
0.6622	Remote Similarity	NPD6653	Approved
0.6621	Remote Similarity	NPD7095	Approved
0.662	Remote Similarity	NPD8651	Approved
0.6618	Remote Similarity	NPD4198	Discontinued
0.6607	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1934	Approved
0.6597	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1241	Discontinued
0.6581	Remote Similarity	NPD3536	Discontinued
0.6575	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3094	Phase 2
0.6565	Remote Similarity	NPD968	Approved
0.6562	Remote Similarity	NPD1242	Phase 1
0.6562	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6355	Discontinued
0.6554	Remote Similarity	NPD1933	Approved
0.6538	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1510	Phase 2
0.6528	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1535	Discovery
0.6524	Remote Similarity	NPD7199	Phase 2
0.6522	Remote Similarity	NPD3817	Phase 2
0.6512	Remote Similarity	NPD940	Approved
0.6512	Remote Similarity	NPD846	Approved
0.6506	Remote Similarity	NPD6166	Phase 2
0.6506	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4626	Approved
0.65	Remote Similarity	NPD6516	Phase 2
0.65	Remote Similarity	NPD5846	Approved
0.65	Remote Similarity	NPD111	Approved
0.6494	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1551	Phase 2
0.649	Remote Similarity	NPD2935	Discontinued
0.6489	Remote Similarity	NPD9697	Approved
0.6485	Remote Similarity	NPD3787	Discontinued
0.6484	Remote Similarity	NPD3020	Approved
0.6483	Remote Similarity	NPD5736	Approved
0.6479	Remote Similarity	NPD1481	Phase 2
0.6479	Remote Similarity	NPD9269	Phase 2
0.6478	Remote Similarity	NPD6599	Discontinued
0.6475	Remote Similarity	NPD1894	Discontinued
0.6474	Remote Similarity	NPD8150	Discontinued
0.6471	Remote Similarity	NPD7240	Approved
0.6471	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3268	Approved
0.6462	Remote Similarity	NPD6647	Phase 2
0.646	Remote Similarity	NPD7819	Suspended
0.6458	Remote Similarity	NPD1203	Approved
0.6458	Remote Similarity	NPD2797	Approved
0.6458	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD3847	Discontinued
0.6447	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5763	Approved
0.6447	Remote Similarity	NPD5762	Approved
0.6444	Remote Similarity	NPD228	Approved
0.6441	Remote Similarity	NPD6534	Approved
0.6441	Remote Similarity	NPD6535	Approved
0.6434	Remote Similarity	NPD4749	Approved
0.6434	Remote Similarity	NPD3685	Discontinued
0.6429	Remote Similarity	NPD7435	Discontinued
0.6429	Remote Similarity	NPD5691	Approved
0.6424	Remote Similarity	NPD3748	Approved
0.6423	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD3022	Approved
0.6418	Remote Similarity	NPD3021	Approved
0.6418	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3455	Phase 2
0.6408	Remote Similarity	NPD3092	Approved
0.6395	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3180	Approved
0.6395	Remote Similarity	NPD3179	Approved
0.6393	Remote Similarity	NPD1282	Approved
0.6393	Remote Similarity	NPD8320	Phase 1
0.6393	Remote Similarity	NPD8319	Approved
0.6391	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5844	Phase 1
0.6383	Remote Similarity	NPD1778	Approved
0.6377	Remote Similarity	NPD6671	Approved
0.6376	Remote Similarity	NPD4140	Approved
0.6376	Remote Similarity	NPD1240	Approved
0.637	Remote Similarity	NPD9494	Approved
0.6369	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5048	Discontinued
0.6364	Remote Similarity	NPD9717	Approved
0.6358	Remote Similarity	NPD2801	Approved
0.6354	Remote Similarity	NPD6776	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