NPASS Compound

Structure

CID251062 OpenBabel06191716052D 44 47 0 0 1 0 0 0 0 0999 V2000 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0326 -4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5326 -5.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5326 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5326 -5.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0326 -5.9128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5326 -3.3147 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 -4.5380 -1.4781 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 -3.4641 1.0000 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 -6.8904 -0.9781 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 -9.0326 -4.1808 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 -10.0326 -5.9128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -5.5326 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0326 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 2 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 -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 -5.1962 1.0000 0.0000 C 0 0 1 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 -5.9393 -0.6691 0.0000 C 0 0 1 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 -7.6335 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5326 -6.7788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5326 -1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 -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 -6.6824 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 -6.0326 -2.4487 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 6 1 0 0 0 0 3 16 2 0 0 0 0 4 7 2 0 0 0 0 4 16 1 0 0 0 0 5 8 2 0 0 0 0 5 16 1 0 0 0 0 6 18 2 0 0 0 0 7 18 1 0 0 0 0 8 22 1 0 0 0 0 9 15 1 0 0 0 0 9 23 1 0 0 0 0 10 21 1 0 0 0 0 11 31 1 0 0 0 0 12 17 2 0 0 0 0 12 40 1 0 0 0 0 13 17 1 0 0 0 0 13 41 1 0 0 0 0 14 30 1 0 0 0 0 14 32 1 0 0 0 0 17 19 1 0 0 0 0 18 33 1 0 0 0 0 19 10 1 1 0 0 0 19 24 1 0 0 0 0 20 11 1 6 0 0 0 20 25 1 0 0 0 0 20 42 1 0 0 0 0 21 30 1 6 0 0 0 21 43 1 0 0 0 0 22 34 2 0 0 0 0 22 43 1 0 0 0 0 23 35 2 0 0 0 0 23 44 1 0 0 0 0 24 28 1 0 0 0 0 24 30 1 1 0 0 0 25 26 1 0 0 0 0 25 36 1 1 0 0 0 26 27 1 0 0 0 0 26 37 1 6 0 0 0 27 29 1 0 0 0 0 27 38 1 1 0 0 0 28 40 1 0 0 0 0 28 44 1 6 0 0 0 29 41 1 6 0 0 0 29 42 1 0 0 0 0 30 39 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.24
Volume:	597.818
LogP:	1.332
LogD:	0.564
LogS:	-2.647
# Rotatable Bonds:	13
TPSA:	221.9
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.12
Synthetic Accessibility Score:	5.137
Fsp3:	0.6
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.204
MDCK Permeability:	9.671718726167455e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.746
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	67.19387817382812%
Volume Distribution (VD):	0.362
Pgp-substrate:	18.577966690063477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	1.437
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.128
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.68
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.889
Carcinogencity:	0.875
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.763

Download Data

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

Natural Product: NPC251062

Natural Product ID:	NPC251062
*Common Name:**	Luzonoside A
IUPAC Name:	[(1S,4aS,6S,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-6-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate
Synonyms:
Standard InCHIKey:	VUZLGISBPIEZOX-HJBLAVRFSA-N
Standard InCHI:	InChI=1S/C30H40O14/c1-15(2)9-23(35)44-28-24-19(17(12-40-28)13-41-29-27(38)26(37)25(36)20(11-31)42-29)10-21(30(24,39)14-32)43-22(34)8-5-16-3-6-18(33)7-4-16/h3-8,12,15,19-21,24-29,31-33,36-39H,9-11,13-14H2,1-2H3/b8-5+/t19-,20-,21+,24-,25-,26+,27-,28+,29-,30-/m1/s1
SMILES:	CC(C)CC(=O)O[C@H]1[C@H]2[C@H](C[C@@H]([C@@]2(CO)O)OC(=O)/C=C/c2ccc(cc2)O)C(=CO1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510787
PubChem CID:	11319570
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568771]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15635247]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3390.0	nM	PMID[490340]

☑ 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 NPC251062 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	1062
0.2-0.3	2477
0.3-0.4	5118
0.4-0.5	10106
0.5-0.6	10224
0.6-0.7	10853
0.7-0.8	2357
0.8-0.85	143
0.85-0.9	46
0.9-0.95	16
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC184464
0.9781	High Similarity	NPC186296
0.9779	High Similarity	NPC154262
0.9779	High Similarity	NPC137501
0.9779	High Similarity	NPC7518
0.9779	High Similarity	NPC159387
0.9507	High Similarity	NPC96599
0.9489	High Similarity	NPC49597
0.9441	High Similarity	NPC240592
0.9441	High Similarity	NPC117346
0.9429	High Similarity	NPC296659
0.9429	High Similarity	NPC202391
0.9353	High Similarity	NPC46644
0.9241	High Similarity	NPC289021
0.9241	High Similarity	NPC158546
0.922	High Similarity	NPC237872
0.922	High Similarity	NPC302286
0.922	High Similarity	NPC263397
0.922	High Similarity	NPC116104
0.922	High Similarity	NPC88754
0.9122	High Similarity	NPC475484
0.911	High Similarity	NPC475379
0.906	High Similarity	NPC475378
0.9028	High Similarity	NPC37838
0.9021	High Similarity	NPC478240
0.8978	High Similarity	NPC254819
0.8973	High Similarity	NPC478234
0.8973	High Similarity	NPC478236
0.8966	High Similarity	NPC18789
0.8936	High Similarity	NPC220936
0.8936	High Similarity	NPC31745
0.8921	High Similarity	NPC169398
0.8919	High Similarity	NPC194705
0.8912	High Similarity	NPC147224
0.8859	High Similarity	NPC229354
0.8851	High Similarity	NPC269914
0.8851	High Similarity	NPC478249
0.8819	High Similarity	NPC293154
0.8816	High Similarity	NPC179914
0.8808	High Similarity	NPC478248
0.8792	High Similarity	NPC478235
0.8784	High Similarity	NPC35097
0.8776	High Similarity	NPC308178
0.8767	High Similarity	NPC473147
0.8767	High Similarity	NPC119773
0.8767	High Similarity	NPC474268
0.8767	High Similarity	NPC475539
0.8767	High Similarity	NPC143246
0.8759	High Similarity	NPC194938
0.8759	High Similarity	NPC63304
0.8733	High Similarity	NPC229548
0.8733	High Similarity	NPC89693
0.8733	High Similarity	NPC478241
0.8732	High Similarity	NPC65262
0.8732	High Similarity	NPC101686
0.8732	High Similarity	NPC469364
0.871	High Similarity	NPC109990
0.8705	High Similarity	NPC478255
0.8705	High Similarity	NPC475824
0.8699	High Similarity	NPC475528
0.869	High Similarity	NPC475213
0.869	High Similarity	NPC152796
0.8686	High Similarity	NPC106677
0.8675	High Similarity	NPC478232
0.8662	High Similarity	NPC472132
0.8649	High Similarity	NPC120728
0.8645	High Similarity	NPC145847
0.863	High Similarity	NPC473281
0.863	High Similarity	NPC77922
0.8621	High Similarity	NPC296643
0.8613	High Similarity	NPC267733
0.8613	High Similarity	NPC276047
0.8609	High Similarity	NPC257847
0.8582	High Similarity	NPC470143
0.8582	High Similarity	NPC322503
0.8571	High Similarity	NPC46137
0.8571	High Similarity	NPC235294
0.8551	High Similarity	NPC471881
0.8551	High Similarity	NPC288416
0.8551	High Similarity	NPC45224
0.8551	High Similarity	NPC35288
0.8551	High Similarity	NPC173150
0.8551	High Similarity	NPC156692
0.8551	High Similarity	NPC471882
0.8533	High Similarity	NPC69367
0.8516	High Similarity	NPC130489
0.8516	High Similarity	NPC478265
0.8516	High Similarity	NPC138993
0.8516	High Similarity	NPC208676
0.8514	High Similarity	NPC212808
0.8514	High Similarity	NPC320734
0.8506	High Similarity	NPC329997
0.8491	Intermediate Similarity	NPC21956
0.8489	Intermediate Similarity	NPC225307
0.8478	Intermediate Similarity	NPC252114
0.8478	Intermediate Similarity	NPC471157
0.8478	Intermediate Similarity	NPC61181
0.8477	Intermediate Similarity	NPC77310
0.8477	Intermediate Similarity	NPC474620
0.8467	Intermediate Similarity	NPC161955
0.8467	Intermediate Similarity	NPC145287
0.8456	Intermediate Similarity	NPC52097
0.8456	Intermediate Similarity	NPC473149
0.844	Intermediate Similarity	NPC281798
0.844	Intermediate Similarity	NPC138777
0.844	Intermediate Similarity	NPC246869
0.844	Intermediate Similarity	NPC225384
0.8435	Intermediate Similarity	NPC204644
0.8429	Intermediate Similarity	NPC253595
0.8421	Intermediate Similarity	NPC203664
0.8417	Intermediate Similarity	NPC175333
0.8417	Intermediate Similarity	NPC103533
0.8414	Intermediate Similarity	NPC321184
0.8414	Intermediate Similarity	NPC171134
0.8414	Intermediate Similarity	NPC328273
0.8414	Intermediate Similarity	NPC321638
0.8408	Intermediate Similarity	NPC476011
0.8406	Intermediate Similarity	NPC126991
0.8406	Intermediate Similarity	NPC83218
0.84	Intermediate Similarity	NPC189631
0.8397	Intermediate Similarity	NPC269668
0.8397	Intermediate Similarity	NPC474936
0.8387	Intermediate Similarity	NPC187205
0.8382	Intermediate Similarity	NPC11724
0.8366	Intermediate Similarity	NPC469699
0.8365	Intermediate Similarity	NPC130730
0.8365	Intermediate Similarity	NPC301910
0.8333	Intermediate Similarity	NPC263829
0.8333	Intermediate Similarity	NPC97240
0.8322	Intermediate Similarity	NPC254398
0.8322	Intermediate Similarity	NPC210330
0.8313	Intermediate Similarity	NPC208818
0.8311	Intermediate Similarity	NPC478250
0.8309	Intermediate Similarity	NPC476872
0.8298	Intermediate Similarity	NPC469549
0.8291	Intermediate Similarity	NPC206815
0.8288	Intermediate Similarity	NPC81515
0.8288	Intermediate Similarity	NPC64141
0.8288	Intermediate Similarity	NPC476383
0.8288	Intermediate Similarity	NPC68092
0.8288	Intermediate Similarity	NPC472350
0.8288	Intermediate Similarity	NPC89105
0.8288	Intermediate Similarity	NPC197316
0.8278	Intermediate Similarity	NPC23677
0.8276	Intermediate Similarity	NPC471345
0.8267	Intermediate Similarity	NPC474234
0.8264	Intermediate Similarity	NPC886
0.8264	Intermediate Similarity	NPC34293
0.8264	Intermediate Similarity	NPC471883
0.8264	Intermediate Similarity	NPC287597
0.8255	Intermediate Similarity	NPC196063
0.8255	Intermediate Similarity	NPC141455
0.8255	Intermediate Similarity	NPC96447
0.8255	Intermediate Similarity	NPC296954
0.8255	Intermediate Similarity	NPC300894
0.8252	Intermediate Similarity	NPC473924
0.8252	Intermediate Similarity	NPC473285
0.8243	Intermediate Similarity	NPC284957
0.8224	Intermediate Similarity	NPC478242
0.8219	Intermediate Similarity	NPC476376
0.8219	Intermediate Similarity	NPC260425
0.8217	Intermediate Similarity	NPC469384
0.8207	Intermediate Similarity	NPC476870
0.8205	Intermediate Similarity	NPC478266
0.8199	Intermediate Similarity	NPC286809
0.8194	Intermediate Similarity	NPC28637
0.8188	Intermediate Similarity	NPC105005
0.8188	Intermediate Similarity	NPC469367
0.8188	Intermediate Similarity	NPC40305
0.8182	Intermediate Similarity	NPC478268
0.8182	Intermediate Similarity	NPC219677
0.8176	Intermediate Similarity	NPC476385
0.8176	Intermediate Similarity	NPC134405
0.8176	Intermediate Similarity	NPC476377
0.8176	Intermediate Similarity	NPC47471
0.8175	Intermediate Similarity	NPC469548
0.8175	Intermediate Similarity	NPC476448
0.8175	Intermediate Similarity	NPC476445
0.8169	Intermediate Similarity	NPC229784
0.8169	Intermediate Similarity	NPC477293
0.8169	Intermediate Similarity	NPC295970
0.8169	Intermediate Similarity	NPC477294
0.8163	Intermediate Similarity	NPC220942
0.8163	Intermediate Similarity	NPC205195
0.8158	Intermediate Similarity	NPC220282
0.8158	Intermediate Similarity	NPC169510
0.8153	Intermediate Similarity	NPC475663
0.8153	Intermediate Similarity	NPC286919
0.8151	Intermediate Similarity	NPC470572
0.8146	Intermediate Similarity	NPC229505
0.8137	Intermediate Similarity	NPC282551
0.8133	Intermediate Similarity	NPC110063
0.8129	Intermediate Similarity	NPC232454
0.8129	Intermediate Similarity	NPC178449
0.8129	Intermediate Similarity	NPC470907
0.8121	Intermediate Similarity	NPC140502
0.8121	Intermediate Similarity	NPC265648
0.8121	Intermediate Similarity	NPC222433
0.8116	Intermediate Similarity	NPC469686
0.811	Intermediate Similarity	NPC195972

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 NPC251062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	685
0.2-0.3	1528
0.3-0.4	2711
0.4-0.5	2278
0.5-0.6	1303
0.6-0.7	359
0.7-0.8	46
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8288	Intermediate Similarity	NPD7266	Discontinued
0.8221	Intermediate Similarity	NPD7685	Pre-registration
0.7533	Intermediate Similarity	NPD6653	Approved
0.7532	Intermediate Similarity	NPD1653	Approved
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5736	Approved
0.7407	Intermediate Similarity	NPD8455	Phase 2
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6190	Approved
0.7368	Intermediate Similarity	NPD7097	Phase 1
0.7338	Intermediate Similarity	NPD5762	Approved
0.7338	Intermediate Similarity	NPD5763	Approved
0.7337	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7285	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3094	Phase 2
0.7255	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7199	Phase 2
0.7241	Intermediate Similarity	NPD1091	Approved
0.7239	Intermediate Similarity	NPD37	Approved
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.723	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6234	Discontinued
0.7226	Intermediate Similarity	NPD6002	Phase 3
0.7226	Intermediate Similarity	NPD6004	Phase 3
0.7226	Intermediate Similarity	NPD6005	Phase 3
0.7226	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6663	Approved
0.7212	Intermediate Similarity	NPD4966	Approved
0.7212	Intermediate Similarity	NPD4967	Phase 2
0.7212	Intermediate Similarity	NPD4965	Approved
0.7193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.7162	Intermediate Similarity	NPD6362	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD7799	Discontinued
0.7135	Intermediate Similarity	NPD3818	Discontinued
0.7124	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5124	Phase 1
0.7123	Intermediate Similarity	NPD3092	Approved
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7114	Intermediate Similarity	NPD5647	Approved
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7093	Intermediate Similarity	NPD7054	Approved
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7067	Intermediate Similarity	NPD2861	Phase 2
0.7066	Intermediate Similarity	NPD7075	Discontinued
0.7059	Intermediate Similarity	NPD4140	Approved
0.7059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7074	Phase 3
0.7052	Intermediate Similarity	NPD7472	Approved
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7013	Intermediate Similarity	NPD5735	Approved
0.7012	Intermediate Similarity	NPD7028	Phase 2
0.7	Intermediate Similarity	NPD5058	Phase 3
0.7	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5126	Approved
0.6986	Remote Similarity	NPD5125	Phase 3
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8166	Discontinued
0.6975	Remote Similarity	NPD6273	Approved
0.6974	Remote Similarity	NPD7095	Approved
0.6971	Remote Similarity	NPD7240	Approved
0.6971	Remote Similarity	NPD7251	Discontinued
0.6966	Remote Similarity	NPD9545	Approved
0.6962	Remote Similarity	NPD2424	Discontinued
0.6957	Remote Similarity	NPD6685	Approved
0.6951	Remote Similarity	NPD7458	Discontinued
0.6932	Remote Similarity	NPD7808	Phase 3
0.6932	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6674	Discontinued
0.6914	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6797	Phase 2
0.6905	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD7157	Approved
0.6875	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3027	Phase 3
0.6849	Remote Similarity	NPD3091	Approved
0.6849	Remote Similarity	NPD7741	Discontinued
0.6839	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4060	Phase 1
0.6839	Remote Similarity	NPD3620	Phase 2
0.6831	Remote Similarity	NPD969	Suspended
0.6829	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6801	Discontinued
0.6821	Remote Similarity	NPD2797	Approved
0.6818	Remote Similarity	NPD6798	Discontinued
0.681	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7503	Approved
0.6797	Remote Similarity	NPD4908	Phase 1
0.6795	Remote Similarity	NPD230	Phase 1
0.6795	Remote Similarity	NPD4340	Discontinued
0.679	Remote Similarity	NPD7236	Approved
0.6786	Remote Similarity	NPD1358	Approved
0.6783	Remote Similarity	NPD7843	Approved
0.6779	Remote Similarity	NPD422	Phase 1
0.6779	Remote Similarity	NPD3705	Approved
0.677	Remote Similarity	NPD3750	Approved
0.6768	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5765	Approved
0.6731	Remote Similarity	NPD1613	Approved
0.6731	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5403	Approved
0.6714	Remote Similarity	NPD3134	Approved
0.6713	Remote Similarity	NPD6912	Phase 3
0.671	Remote Similarity	NPD3268	Approved
0.671	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7239	Suspended
0.6686	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD4110	Phase 3
0.6647	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5402	Approved
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6353	Approved
0.6646	Remote Similarity	NPD5958	Discontinued
0.6645	Remote Similarity	NPD8651	Approved
0.6645	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4198	Discontinued
0.6644	Remote Similarity	NPD3095	Discontinued
0.6633	Remote Similarity	NPD7930	Approved
0.6632	Remote Similarity	NPD7497	Discontinued
0.6632	Remote Similarity	NPD7435	Discontinued
0.6627	Remote Similarity	NPD1934	Approved
0.6625	Remote Similarity	NPD2935	Discontinued
0.662	Remote Similarity	NPD2684	Approved
0.6619	Remote Similarity	NPD6647	Phase 2
0.6612	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5844	Phase 1
0.661	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7768	Phase 2
0.6606	Remote Similarity	NPD5401	Approved
0.6604	Remote Similarity	NPD4538	Approved
0.6604	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4536	Approved
0.6603	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD8320	Phase 1
0.6597	Remote Similarity	NPD8319	Approved
0.6596	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8434	Phase 2
0.6593	Remote Similarity	NPD8150	Discontinued
0.6588	Remote Similarity	NPD5761	Phase 2
0.6588	Remote Similarity	NPD5760	Phase 2
0.6588	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7585	Approved
0.6579	Remote Similarity	NPD5327	Phase 3
0.6577	Remote Similarity	NPD1357	Approved
0.6575	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7411	Suspended
0.6562	Remote Similarity	NPD7999	Approved
0.6562	Remote Similarity	NPD5588	Approved
0.6562	Remote Similarity	NPD1510	Phase 2
0.6561	Remote Similarity	NPD4062	Phase 3
0.6558	Remote Similarity	NPD4624	Approved
0.6558	Remote Similarity	NPD2798	Approved
0.6554	Remote Similarity	NPD3751	Discontinued
0.655	Remote Similarity	NPD3817	Phase 2
0.6545	Remote Similarity	NPD7680	Approved
0.6545	Remote Similarity	NPD6799	Approved
0.6543	Remote Similarity	NPD1549	Phase 2
0.6536	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD3225	Approved
0.6536	Remote Similarity	NPD1876	Approved
0.6534	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6166	Phase 2
0.6534	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3019	Approved
0.6533	Remote Similarity	NPD2932	Approved
0.6533	Remote Similarity	NPD4059	Approved
0.6533	Remote Similarity	NPD4626	Approved
0.6528	Remote Similarity	NPD7583	Approved
0.6522	Remote Similarity	NPD2438	Suspended
0.6522	Remote Similarity	NPD3020	Approved
0.6513	Remote Similarity	NPD1608	Approved
0.6509	Remote Similarity	NPD6599	Discontinued
0.6506	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6764	Approved
0.65	Remote Similarity	NPD6765	Approved
0.6497	Remote Similarity	NPD7473	Discontinued
0.6494	Remote Similarity	NPD987	Approved
0.6492	Remote Similarity	NPD6823	Phase 2
0.649	Remote Similarity	NPD3496	Discontinued
0.649	Remote Similarity	NPD3847	Discontinued
0.6486	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6667	Approved
0.6485	Remote Similarity	NPD6666	Approved
0.6484	Remote Similarity	NPD7090	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