NPASS Compound

Structure

CID260781 OpenBabel06191716062D 41 44 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -6.0622 -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 2.0000 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 1.7321 -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 -5.1962 -1.0000 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 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 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 -4.3301 0.5000 0.0000 C 0 0 1 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 -4.3301 3.5000 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 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 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 -6.0622 0.5000 0.0000 C 0 0 0 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 -2.5981 -2.5000 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 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 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 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 36 1 0 0 0 0 2 37 1 0 0 0 0 3 38 1 0 0 0 0 4 39 1 0 0 0 0 5 12 1 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 17 2 0 0 0 0 9 29 1 0 0 0 0 10 30 1 0 0 0 0 11 40 1 0 0 0 0 12 21 1 0 0 0 0 14 9 1 6 0 0 0 14 15 1 0 0 0 0 15 11 1 6 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 16 36 1 0 0 0 0 17 22 1 0 0 0 0 17 37 1 0 0 0 0 18 24 2 0 0 0 0 18 38 1 0 0 0 0 19 10 1 1 0 0 0 19 23 1 0 0 0 0 19 41 1 0 0 0 0 20 13 1 1 0 0 0 20 21 1 0 0 0 0 21 27 2 0 0 0 0 22 31 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 27 1 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 34 1 1 0 0 0 26 28 1 0 0 0 0 26 35 1 6 0 0 0 27 39 1 0 0 0 0 28 40 1 1 0 0 0 28 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.23
Volume:	557.072
LogP:	0.197
LogD:	0.425
LogS:	-2.432
# Rotatable Bonds:	10
TPSA:	196.99
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	4.6
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.388
MDCK Permeability:	1.9639046513475478e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.815
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.278

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	77.37290954589844%
Volume Distribution (VD):	0.415
Pgp-substrate:	28.976566314697266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.265
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.619

ADMET: Excretion

Clearance (CL):	5.635
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.363
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.233
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC260781

Natural Product ID:	NPC260781
*Common Name:**	(2R,3S,4R)-3Alpha-[(Beta-D-Glucopyranosyl)Oxy]Lyoniresinol
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(1R,2S,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	PQQRNPDHSJDAGV-BNJSROQMSA-N
Standard InCHI:	InChI=1S/C28H38O13/c1-36-16-7-13(8-17(37-2)22(16)31)20-15(11-40-28-26(35)25(34)23(32)19(10-30)41-28)14(9-29)5-12-6-18(38-3)24(33)27(39-4)21(12)20/h6-8,14-15,19-20,23,25-26,28-35H,5,9-11H2,1-4H3/t14-,15+,19+,20-,23+,25-,26+,28+/m0/s1
SMILES:	OC[C@@H]1Cc2cc(OC)c(c(c2[C@H]([C@@H]1CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1cc(OC)c(c(c1)OC)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813180
PubChem CID:	56681890
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

*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
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	1000000.0	nM	PMID[551040]

☑ 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 NPC260781 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	465
0.1-0.2	1573
0.2-0.3	3854
0.3-0.4	8825
0.4-0.5	9112
0.5-0.6	4991
0.6-0.7	7507
0.7-0.8	4956
0.8-0.85	986
0.85-0.9	371
0.9-0.95	43
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC225815
1.0	High Similarity	NPC469706
1.0	High Similarity	NPC214326
1.0	High Similarity	NPC185955
1.0	High Similarity	NPC145979
1.0	High Similarity	NPC182368
1.0	High Similarity	NPC218041
1.0	High Similarity	NPC9933
1.0	High Similarity	NPC469707
0.9589	High Similarity	NPC21902
0.951	High Similarity	NPC272619
0.951	High Similarity	NPC286245
0.9441	High Similarity	NPC471065
0.9441	High Similarity	NPC253015
0.9437	High Similarity	NPC472714
0.9437	High Similarity	NPC5262
0.9384	High Similarity	NPC44452
0.932	High Similarity	NPC472709
0.932	High Similarity	NPC472710
0.9306	High Similarity	NPC472713
0.9306	High Similarity	NPC187774
0.9306	High Similarity	NPC473046
0.9306	High Similarity	NPC118385
0.9306	High Similarity	NPC472712
0.9241	High Similarity	NPC277867
0.9241	High Similarity	NPC475096
0.9241	High Similarity	NPC161700
0.9225	High Similarity	NPC230124
0.9225	High Similarity	NPC6300
0.9225	High Similarity	NPC114171
0.9189	High Similarity	NPC183380
0.9189	High Similarity	NPC24425
0.9178	High Similarity	NPC125755
0.9178	High Similarity	NPC190714
0.9178	High Similarity	NPC99515
0.9167	High Similarity	NPC191231
0.9133	High Similarity	NPC78809
0.9116	High Similarity	NPC227902
0.9116	High Similarity	NPC39657
0.9103	High Similarity	NPC37793
0.9091	High Similarity	NPC184613
0.9054	High Similarity	NPC175976
0.9054	High Similarity	NPC270751
0.9054	High Similarity	NPC248132
0.9054	High Similarity	NPC130449
0.9041	High Similarity	NPC25292
0.9041	High Similarity	NPC76176
0.9041	High Similarity	NPC164183
0.9041	High Similarity	NPC469313
0.9041	High Similarity	NPC168579
0.9041	High Similarity	NPC133251
0.9041	High Similarity	NPC473045
0.9041	High Similarity	NPC138227
0.9034	High Similarity	NPC189115
0.9034	High Similarity	NPC475084
0.9034	High Similarity	NPC469559
0.9026	High Similarity	NPC1253
0.9026	High Similarity	NPC100936
0.9007	High Similarity	NPC475227
0.9007	High Similarity	NPC200645
0.9007	High Similarity	NPC106669
0.8993	High Similarity	NPC51328
0.8993	High Similarity	NPC55158
0.8993	High Similarity	NPC286235
0.8986	High Similarity	NPC193473
0.8986	High Similarity	NPC213074
0.8986	High Similarity	NPC31325
0.8986	High Similarity	NPC224674
0.8986	High Similarity	NPC275284
0.8986	High Similarity	NPC15538
0.8986	High Similarity	NPC473480
0.8986	High Similarity	NPC15956
0.8986	High Similarity	NPC114505
0.898	High Similarity	NPC166506
0.898	High Similarity	NPC189239
0.898	High Similarity	NPC110763
0.898	High Similarity	NPC197352
0.8974	High Similarity	NPC116759
0.8974	High Similarity	NPC14294
0.8973	High Similarity	NPC278961
0.8973	High Similarity	NPC473044
0.8973	High Similarity	NPC113680
0.8966	High Similarity	NPC472711
0.8966	High Similarity	NPC469661
0.8951	High Similarity	NPC52277
0.8951	High Similarity	NPC199459
0.8951	High Similarity	NPC177035
0.8944	High Similarity	NPC107478
0.894	High Similarity	NPC474442
0.8926	High Similarity	NPC280945
0.8926	High Similarity	NPC179809
0.8924	High Similarity	NPC185498
0.8919	High Similarity	NPC112251
0.8912	High Similarity	NPC121661
0.8912	High Similarity	NPC473108
0.8912	High Similarity	NPC73467
0.8904	High Similarity	NPC48309
0.8889	High Similarity	NPC474039
0.8881	High Similarity	NPC313081
0.8874	High Similarity	NPC473621
0.8874	High Similarity	NPC2745
0.8867	High Similarity	NPC474893
0.8867	High Similarity	NPC220006
0.8867	High Similarity	NPC181452
0.8867	High Similarity	NPC475940
0.8859	High Similarity	NPC474397
0.8851	High Similarity	NPC307466
0.8851	High Similarity	NPC476301
0.8851	High Similarity	NPC43508
0.8846	High Similarity	NPC100465
0.8846	High Similarity	NPC152424
0.8844	High Similarity	NPC469630
0.8844	High Similarity	NPC477898
0.8844	High Similarity	NPC470950
0.8844	High Similarity	NPC185307
0.8844	High Similarity	NPC472451
0.8844	High Similarity	NPC324962
0.8844	High Similarity	NPC252169
0.8839	High Similarity	NPC185231
0.8836	High Similarity	NPC178054
0.8836	High Similarity	NPC210192
0.8828	High Similarity	NPC471183
0.8828	High Similarity	NPC212770
0.8828	High Similarity	NPC98777
0.8819	High Similarity	NPC202846
0.8819	High Similarity	NPC143139
0.8816	High Similarity	NPC44192
0.8816	High Similarity	NPC233467
0.8816	High Similarity	NPC302610
0.8816	High Similarity	NPC322899
0.8816	High Similarity	NPC272552
0.8816	High Similarity	NPC134911
0.8816	High Similarity	NPC469944
0.8816	High Similarity	NPC226108
0.8816	High Similarity	NPC471154
0.8816	High Similarity	NPC46283
0.8816	High Similarity	NPC157783
0.8812	High Similarity	NPC179240
0.8811	High Similarity	NPC125649
0.8811	High Similarity	NPC209199
0.8808	High Similarity	NPC98624
0.8808	High Similarity	NPC477612
0.8808	High Similarity	NPC195561
0.8808	High Similarity	NPC158784
0.8803	High Similarity	NPC161958
0.8803	High Similarity	NPC14224
0.8803	High Similarity	NPC470270
0.88	High Similarity	NPC291326
0.88	High Similarity	NPC473876
0.88	High Similarity	NPC474834
0.88	High Similarity	NPC474940
0.88	High Similarity	NPC290902
0.88	High Similarity	NPC474795
0.88	High Similarity	NPC159697
0.88	High Similarity	NPC474856
0.88	High Similarity	NPC117788
0.88	High Similarity	NPC303013
0.88	High Similarity	NPC130959
0.8797	High Similarity	NPC222531
0.8792	High Similarity	NPC474054
0.8792	High Similarity	NPC252286
0.8792	High Similarity	NPC33832
0.8792	High Similarity	NPC260397
0.8792	High Similarity	NPC233980
0.8792	High Similarity	NPC154971
0.8784	High Similarity	NPC84181
0.8784	High Similarity	NPC471667
0.8784	High Similarity	NPC79429
0.8784	High Similarity	NPC470235
0.8784	High Similarity	NPC217635
0.8784	High Similarity	NPC50250
0.8784	High Similarity	NPC283995
0.8784	High Similarity	NPC129417
0.8782	High Similarity	NPC91634
0.8782	High Similarity	NPC268718
0.8782	High Similarity	NPC150943
0.8776	High Similarity	NPC103637
0.8776	High Similarity	NPC230538
0.8776	High Similarity	NPC133934
0.8776	High Similarity	NPC36531
0.8776	High Similarity	NPC184684
0.8776	High Similarity	NPC229172
0.8776	High Similarity	NPC184641
0.8776	High Similarity	NPC41782
0.8776	High Similarity	NPC476356
0.8767	High Similarity	NPC266197
0.8767	High Similarity	NPC177868
0.8767	High Similarity	NPC106944
0.8767	High Similarity	NPC291101
0.8759	High Similarity	NPC470413
0.8759	High Similarity	NPC86605
0.8759	High Similarity	NPC138738
0.8759	High Similarity	NPC196420
0.8759	High Similarity	NPC3072
0.8759	High Similarity	NPC46277
0.8759	High Similarity	NPC59324
0.8759	High Similarity	NPC65530
0.8759	High Similarity	NPC304152
0.8759	High Similarity	NPC301765
0.8759	High Similarity	NPC156948

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 NPC260781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	866
0.2-0.3	1914
0.3-0.4	2838
0.4-0.5	1629
0.5-0.6	933
0.6-0.7	473
0.7-0.8	107
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8924	High Similarity	NPD7228	Approved
0.8836	High Similarity	NPD6674	Discontinued
0.8718	High Similarity	NPD6234	Discontinued
0.8636	High Similarity	NPD37	Approved
0.859	High Similarity	NPD4967	Phase 2
0.859	High Similarity	NPD4966	Approved
0.859	High Similarity	NPD4965	Approved
0.8462	Intermediate Similarity	NPD3027	Phase 3
0.8414	Intermediate Similarity	NPD1613	Approved
0.8414	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7240	Approved
0.8194	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1653	Approved
0.8138	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8079	Intermediate Similarity	NPD7266	Discontinued
0.8072	Intermediate Similarity	NPD7054	Approved
0.8037	Intermediate Similarity	NPD7199	Phase 2
0.8027	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7472	Approved
0.8014	Intermediate Similarity	NPD4908	Phase 1
0.7966	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3620	Phase 2
0.7919	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7251	Discontinued
0.7798	Intermediate Similarity	NPD3818	Discontinued
0.7791	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD7680	Approved
0.7785	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD3705	Approved
0.7765	Intermediate Similarity	NPD6797	Phase 2
0.7751	Intermediate Similarity	NPD5844	Phase 1
0.7746	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4625	Phase 3
0.7688	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6166	Phase 2
0.7679	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1091	Approved
0.7655	Intermediate Similarity	NPD1610	Phase 2
0.7636	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7473	Discontinued
0.7628	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1934	Approved
0.7561	Intermediate Similarity	NPD8455	Phase 2
0.7561	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6232	Discontinued
0.7551	Intermediate Similarity	NPD4749	Approved
0.7544	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.7467	Intermediate Similarity	NPD3018	Phase 2
0.7467	Intermediate Similarity	NPD2861	Phase 2
0.7455	Intermediate Similarity	NPD1465	Phase 2
0.7451	Intermediate Similarity	NPD4060	Phase 1
0.743	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7685	Pre-registration
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.736	Intermediate Similarity	NPD6842	Approved
0.736	Intermediate Similarity	NPD6843	Phase 3
0.736	Intermediate Similarity	NPD6841	Approved
0.7356	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7315	Intermediate Similarity	NPD2983	Phase 2
0.7315	Intermediate Similarity	NPD2982	Phase 2
0.7294	Intermediate Similarity	NPD6959	Discontinued
0.729	Intermediate Similarity	NPD5735	Approved
0.7284	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5125	Phase 3
0.7279	Intermediate Similarity	NPD5126	Approved
0.7278	Intermediate Similarity	NPD5763	Approved
0.7278	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5762	Approved
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7263	Intermediate Similarity	NPD7906	Approved
0.7261	Intermediate Similarity	NPD4108	Discontinued
0.726	Intermediate Similarity	NPD1548	Phase 1
0.7248	Intermediate Similarity	NPD2981	Phase 2
0.7246	Intermediate Similarity	NPD2801	Approved
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD6100	Approved
0.7212	Intermediate Similarity	NPD4005	Discontinued
0.7211	Intermediate Similarity	NPD8151	Discontinued
0.7211	Intermediate Similarity	NPD1357	Approved
0.7207	Intermediate Similarity	NPD4663	Approved
0.7202	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7195	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8127	Discontinued
0.7191	Intermediate Similarity	NPD8054	Approved
0.7191	Intermediate Similarity	NPD8053	Approved
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7179	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5124	Phase 1
0.7168	Intermediate Similarity	NPD2489	Approved
0.7168	Intermediate Similarity	NPD27	Approved
0.716	Intermediate Similarity	NPD5058	Phase 3
0.7151	Intermediate Similarity	NPD3051	Approved
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7135	Intermediate Similarity	NPD7313	Approved
0.7135	Intermediate Similarity	NPD5494	Approved
0.7135	Intermediate Similarity	NPD7311	Approved
0.7135	Intermediate Similarity	NPD7312	Approved
0.7135	Intermediate Similarity	NPD7310	Approved
0.7135	Intermediate Similarity	NPD4577	Approved
0.7135	Intermediate Similarity	NPD4578	Approved
0.7133	Intermediate Similarity	NPD228	Approved
0.7118	Intermediate Similarity	NPD7075	Discontinued
0.7117	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7041	Phase 2
0.711	Intermediate Similarity	NPD2969	Approved
0.711	Intermediate Similarity	NPD2970	Approved
0.7105	Intermediate Similarity	NPD3094	Phase 2
0.7101	Intermediate Similarity	NPD3817	Phase 2
0.7095	Intermediate Similarity	NPD7309	Approved
0.7081	Intermediate Similarity	NPD5177	Phase 3
0.7079	Intermediate Similarity	NPD7549	Discontinued
0.7074	Intermediate Similarity	NPD6823	Phase 2
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7447	Phase 1
0.707	Intermediate Similarity	NPD3657	Discovery
0.7059	Intermediate Similarity	NPD6778	Approved
0.7059	Intermediate Similarity	NPD6781	Approved
0.7059	Intermediate Similarity	NPD6777	Approved
0.7059	Intermediate Similarity	NPD6780	Approved
0.7059	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD6776	Approved
0.7059	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD6779	Approved
0.7041	Intermediate Similarity	NPD2978	Approved
0.7041	Intermediate Similarity	NPD2977	Approved
0.7039	Intermediate Similarity	NPD8651	Approved
0.7037	Intermediate Similarity	NPD7435	Discontinued
0.7012	Intermediate Similarity	NPD7212	Phase 2
0.7012	Intermediate Similarity	NPD1511	Approved
0.7012	Intermediate Similarity	NPD7213	Phase 3
0.7006	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6190	Approved
0.6993	Remote Similarity	NPD3021	Approved
0.6993	Remote Similarity	NPD3022	Approved
0.6987	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4538	Approved
0.6981	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4536	Approved
0.6975	Remote Similarity	NPD1652	Phase 2
0.6974	Remote Similarity	NPD5327	Phase 3
0.6974	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3540	Phase 1
0.6954	Remote Similarity	NPD7229	Phase 3
0.6954	Remote Similarity	NPD3092	Approved
0.6947	Remote Similarity	NPD7697	Approved
0.6947	Remote Similarity	NPD7696	Phase 3
0.6947	Remote Similarity	NPD7698	Approved
0.6941	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7157	Approved
0.6933	Remote Similarity	NPD3892	Phase 2
0.6933	Remote Similarity	NPD3750	Approved
0.6933	Remote Similarity	NPD8166	Discontinued
0.6928	Remote Similarity	NPD6696	Suspended
0.6928	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1512	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4097	Suspended
0.6914	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7870	Phase 2
0.6911	Remote Similarity	NPD7871	Phase 2
0.6905	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7458	Discontinued
0.6905	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2238	Phase 2
0.6894	Remote Similarity	NPD3539	Phase 1
0.6891	Remote Similarity	NPD7701	Phase 2
0.689	Remote Similarity	NPD2677	Approved
0.6882	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4750	Phase 3
0.6875	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7801	Approved
0.6872	Remote Similarity	NPD7783	Phase 2
0.6867	Remote Similarity	NPD2533	Approved
0.6867	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2534	Approved
0.6867	Remote Similarity	NPD2532	Approved
0.6864	Remote Similarity	NPD7028	Phase 2
0.686	Remote Similarity	NPD7768	Phase 2
0.6855	Remote Similarity	NPD6355	Discontinued

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