NPASS Compound

Structure

CID296659 OpenBabel06191716102D 38 41 0 0 1 0 0 0 0 0999 V2000 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 -2.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -0.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 -0.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 -2.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -1.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 0.5672 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 -3.8581 0.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1235 -1.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7852 -2.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -5.5054 0.7752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -1.7321 4.0000 0.0000 C 0 0 0 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 -0.8660 -0.5000 0.0000 C 0 0 1 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 -4.1161 -3.3564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1964 1.7262 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 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 0.0320 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 0.0000 -0.0000 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 1 34 1 0 0 0 0 2 6 1 0 0 0 0 2 13 2 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 9 19 1 0 0 0 0 10 27 1 0 0 0 0 11 35 1 0 0 0 0 12 17 2 0 0 0 0 12 36 1 0 0 0 0 14 11 1 1 0 0 0 14 20 1 0 0 0 0 15 28 1 0 0 0 0 16 8 1 6 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 24 1 0 0 0 0 18 10 1 6 0 0 0 18 21 1 0 0 0 0 18 37 1 0 0 0 0 19 29 2 0 0 0 0 19 35 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 36 1 0 0 0 0 25 38 1 0 0 0 0 26 37 1 0 0 0 0 26 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.19
Volume:	511.054
LogP:	1.851
LogD:	2.039
LogS:	-2.379
# Rotatable Bonds:	10
TPSA:	181.44
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.219
Synthetic Accessibility Score:	4.693
Fsp3:	0.538
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:	-6.09
MDCK Permeability:	6.155748997116461e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.093
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.666
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	75.54570770263672%
Volume Distribution (VD):	0.419
Pgp-substrate:	16.29537582397461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	2.843
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.165
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.207
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.307
Skin Sensitization:	0.903
Carcinogencity:	0.791
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.761

Download Data

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

Natural Product: NPC296659

Natural Product ID:	NPC296659
*Common Name:**	Luzonoside D
IUPAC Name:	methyl (1S,4aS,7S,7aS)-7-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:	luzonoside D
Standard InCHIKey:	COQOXCPEJJIULA-YITUERRASA-N
Standard InCHI:	InChI=1S/C26H32O12/c1-34-24(33)17-12-36-25(38-26-23(32)22(31)21(30)18(10-27)37-26)20-14(5-8-16(17)20)11-35-19(29)9-4-13-2-6-15(28)7-3-13/h2-4,6-7,9,12,14,16,18,20-23,25-28,30-32H,5,8,10-11H2,1H3/b9-4-/t14-,16-,18-,20-,21-,22+,23-,25+,26+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@H](CC3)COC(=O)/C=Cc2ccc(cc2)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486467
PubChem CID:	11785975
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-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	=	100000.0	nM	PMID[511280]

☑ 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 NPC296659 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	283
0.1-0.2	1015
0.2-0.3	2313
0.3-0.4	4495
0.4-0.5	9190
0.5-0.6	10184
0.6-0.7	10960
0.7-0.8	3949
0.8-0.85	210
0.85-0.9	64
0.9-0.95	29
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202391
0.9645	High Similarity	NPC96599
0.9577	High Similarity	NPC117346
0.9577	High Similarity	NPC240592
0.9429	High Similarity	NPC184464
0.9429	High Similarity	NPC251062
0.9375	High Similarity	NPC289021
0.9375	High Similarity	NPC158546
0.9357	High Similarity	NPC186296
0.9348	High Similarity	NPC220936
0.9348	High Similarity	NPC31745
0.9252	High Similarity	NPC475484
0.9241	High Similarity	NPC475379
0.922	High Similarity	NPC293154
0.9214	High Similarity	NPC154262
0.9214	High Similarity	NPC137501
0.9214	High Similarity	NPC7518
0.9214	High Similarity	NPC159387
0.9197	High Similarity	NPC169398
0.9161	High Similarity	NPC143246
0.9161	High Similarity	NPC119773
0.9161	High Similarity	NPC473147
0.9161	High Similarity	NPC474268
0.9161	High Similarity	NPC475539
0.9155	High Similarity	NPC77922
0.9155	High Similarity	NPC473281
0.9103	High Similarity	NPC478234
0.9103	High Similarity	NPC478236
0.9091	High Similarity	NPC475528
0.9085	High Similarity	NPC475213
0.9085	High Similarity	NPC152796
0.9067	High Similarity	NPC179914
0.906	High Similarity	NPC475378
0.9028	High Similarity	NPC212808
0.9021	High Similarity	NPC63304
0.9021	High Similarity	NPC194938
0.9	High Similarity	NPC101686
0.9	High Similarity	NPC65262
0.9	High Similarity	NPC469364
0.8986	High Similarity	NPC257847
0.8978	High Similarity	NPC254819
0.8966	High Similarity	NPC473149
0.8936	High Similarity	NPC49597
0.8919	High Similarity	NPC194705
0.8919	High Similarity	NPC478235
0.8912	High Similarity	NPC69367
0.8912	High Similarity	NPC35097
0.8904	High Similarity	NPC120728
0.8889	High Similarity	NPC145847
0.8881	High Similarity	NPC296643
0.8859	High Similarity	NPC229354
0.8851	High Similarity	NPC474620
0.8831	High Similarity	NPC109990
0.8811	High Similarity	NPC46644
0.8794	High Similarity	NPC472132
0.8792	High Similarity	NPC203664
0.875	High Similarity	NPC187205
0.8714	High Similarity	NPC470143
0.8714	High Similarity	NPC322503
0.8699	High Similarity	NPC210330
0.869	High Similarity	NPC302286
0.869	High Similarity	NPC116104
0.869	High Similarity	NPC263397
0.869	High Similarity	NPC88754
0.869	High Similarity	NPC478250
0.869	High Similarity	NPC237872
0.8675	High Similarity	NPC478232
0.8662	High Similarity	NPC471345
0.8636	High Similarity	NPC208676
0.8636	High Similarity	NPC130489
0.8608	High Similarity	NPC21956
0.8591	High Similarity	NPC161955
0.8582	High Similarity	NPC114116
0.8571	High Similarity	NPC235294
0.8571	High Similarity	NPC46137
0.8571	High Similarity	NPC478255
0.8571	High Similarity	NPC281798
0.8571	High Similarity	NPC469384
0.8551	High Similarity	NPC45224
0.8551	High Similarity	NPC471881
0.8551	High Similarity	NPC106677
0.8551	High Similarity	NPC288416
0.8551	High Similarity	NPC35288
0.8551	High Similarity	NPC156692
0.8551	High Similarity	NPC173150
0.8551	High Similarity	NPC471882
0.8526	High Similarity	NPC476011
0.8523	High Similarity	NPC189631
0.8523	High Similarity	NPC23677
0.8516	High Similarity	NPC474936
0.8516	High Similarity	NPC138993
0.8514	High Similarity	NPC37838
0.8514	High Similarity	NPC320734
0.8506	High Similarity	NPC475663
0.8506	High Similarity	NPC286919
0.8503	High Similarity	NPC478240
0.85	High Similarity	NPC17567
0.8489	Intermediate Similarity	NPC225307
0.8478	Intermediate Similarity	NPC61181
0.8478	Intermediate Similarity	NPC471157
0.8477	Intermediate Similarity	NPC77310
0.8477	Intermediate Similarity	NPC478249
0.8477	Intermediate Similarity	NPC269914
0.8456	Intermediate Similarity	NPC18789
0.8456	Intermediate Similarity	NPC52097
0.8456	Intermediate Similarity	NPC470330
0.844	Intermediate Similarity	NPC138777
0.844	Intermediate Similarity	NPC225384
0.844	Intermediate Similarity	NPC246869
0.8435	Intermediate Similarity	NPC469367
0.8435	Intermediate Similarity	NPC204644
0.8429	Intermediate Similarity	NPC469549
0.8429	Intermediate Similarity	NPC253595
0.8417	Intermediate Similarity	NPC103533
0.8411	Intermediate Similarity	NPC179128
0.8411	Intermediate Similarity	NPC12006
0.8411	Intermediate Similarity	NPC147224
0.8411	Intermediate Similarity	NPC116292
0.8411	Intermediate Similarity	NPC267469
0.8411	Intermediate Similarity	NPC87630
0.8406	Intermediate Similarity	NPC126991
0.8406	Intermediate Similarity	NPC83218
0.84	Intermediate Similarity	NPC308178
0.8389	Intermediate Similarity	NPC291153
0.8389	Intermediate Similarity	NPC208293
0.8387	Intermediate Similarity	NPC329997
0.8387	Intermediate Similarity	NPC49173
0.8382	Intermediate Similarity	NPC11724
0.838	Intermediate Similarity	NPC471095
0.838	Intermediate Similarity	NPC471066
0.8369	Intermediate Similarity	NPC470122
0.8369	Intermediate Similarity	NPC469705
0.8369	Intermediate Similarity	NPC319995
0.8369	Intermediate Similarity	NPC289415
0.8369	Intermediate Similarity	NPC17968
0.8367	Intermediate Similarity	NPC284957
0.8366	Intermediate Similarity	NPC61604
0.8366	Intermediate Similarity	NPC245615
0.8366	Intermediate Similarity	NPC299706
0.8366	Intermediate Similarity	NPC115466
0.8365	Intermediate Similarity	NPC301910
0.8365	Intermediate Similarity	NPC130730
0.8345	Intermediate Similarity	NPC252114
0.8344	Intermediate Similarity	NPC478242
0.8333	Intermediate Similarity	NPC263829
0.8333	Intermediate Similarity	NPC97240
0.8323	Intermediate Similarity	NPC478248
0.8322	Intermediate Similarity	NPC136608
0.8322	Intermediate Similarity	NPC38420
0.8322	Intermediate Similarity	NPC164172
0.8309	Intermediate Similarity	NPC476872
0.8299	Intermediate Similarity	NPC80098
0.8291	Intermediate Similarity	NPC206815
0.8289	Intermediate Similarity	NPC182350
0.8289	Intermediate Similarity	NPC162569
0.8289	Intermediate Similarity	NPC229882
0.8289	Intermediate Similarity	NPC35160
0.8289	Intermediate Similarity	NPC158635
0.8288	Intermediate Similarity	NPC324262
0.8288	Intermediate Similarity	NPC81515
0.8288	Intermediate Similarity	NPC476383
0.8288	Intermediate Similarity	NPC171134
0.8288	Intermediate Similarity	NPC64141
0.8288	Intermediate Similarity	NPC472350
0.8288	Intermediate Similarity	NPC68092
0.8288	Intermediate Similarity	NPC220942
0.8288	Intermediate Similarity	NPC321638
0.8288	Intermediate Similarity	NPC62800
0.8288	Intermediate Similarity	NPC89105
0.8288	Intermediate Similarity	NPC328273
0.8288	Intermediate Similarity	NPC197316
0.8288	Intermediate Similarity	NPC321184
0.8278	Intermediate Similarity	NPC473138
0.8278	Intermediate Similarity	NPC28776
0.8273	Intermediate Similarity	NPC123704
0.8269	Intermediate Similarity	NPC4747
0.8269	Intermediate Similarity	NPC226759
0.8269	Intermediate Similarity	NPC104275
0.8267	Intermediate Similarity	NPC473867
0.8264	Intermediate Similarity	NPC886
0.8264	Intermediate Similarity	NPC471883
0.8264	Intermediate Similarity	NPC287597
0.8264	Intermediate Similarity	NPC34293
0.8258	Intermediate Similarity	NPC156624
0.8258	Intermediate Similarity	NPC38699
0.8258	Intermediate Similarity	NPC172920
0.8255	Intermediate Similarity	NPC471028
0.8252	Intermediate Similarity	NPC473285
0.825	Intermediate Similarity	NPC282551
0.8247	Intermediate Similarity	NPC229548
0.8247	Intermediate Similarity	NPC469699
0.8247	Intermediate Similarity	NPC89693
0.8247	Intermediate Similarity	NPC478241
0.8243	Intermediate Similarity	NPC148080
0.8243	Intermediate Similarity	NPC469623
0.8228	Intermediate Similarity	NPC117943
0.8228	Intermediate Similarity	NPC477627
0.8228	Intermediate Similarity	NPC293568
0.8227	Intermediate Similarity	NPC158673
0.8219	Intermediate Similarity	NPC476376

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 NPC296659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	673
0.2-0.3	1459
0.3-0.4	2561
0.4-0.5	2323
0.5-0.6	1318
0.6-0.7	510
0.7-0.8	64
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
0.7925	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7736	Intermediate Similarity	NPD8455	Phase 2
0.7712	Intermediate Similarity	NPD6190	Approved
0.7669	Intermediate Similarity	NPD7199	Phase 2
0.7651	Intermediate Similarity	NPD7228	Approved
0.7635	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6355	Discontinued
0.7562	Intermediate Similarity	NPD37	Approved
0.7547	Intermediate Similarity	NPD4380	Phase 2
0.7546	Intermediate Similarity	NPD6234	Discontinued
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.7532	Intermediate Similarity	NPD1653	Approved
0.7531	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD4967	Phase 2
0.7531	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD6559	Discontinued
0.747	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7456	Intermediate Similarity	NPD7472	Approved
0.7455	Intermediate Similarity	NPD8127	Discontinued
0.7447	Intermediate Similarity	NPD9545	Approved
0.7417	Intermediate Similarity	NPD6653	Approved
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD3764	Approved
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7347	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6002	Phase 3
0.7338	Intermediate Similarity	NPD6005	Phase 3
0.7338	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6004	Phase 3
0.7333	Intermediate Similarity	NPD6663	Approved
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.732	Intermediate Similarity	NPD7033	Discontinued
0.7317	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6797	Phase 2
0.7308	Intermediate Similarity	NPD8166	Discontinued
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5736	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7240	Approved
0.7255	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7097	Phase 1
0.725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1091	Approved
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7237	Intermediate Similarity	NPD230	Phase 1
0.7233	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5647	Approved
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7197	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD7799	Discontinued
0.7134	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5763	Approved
0.7115	Intermediate Similarity	NPD5762	Approved
0.7091	Intermediate Similarity	NPD7819	Suspended
0.7089	Intermediate Similarity	NPD3750	Approved
0.7081	Intermediate Similarity	NPD6273	Approved
0.707	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2861	Phase 2
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6362	Approved
0.7037	Intermediate Similarity	NPD5403	Approved
0.703	Intermediate Similarity	NPD1934	Approved
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7013	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5124	Phase 1
0.7012	Intermediate Similarity	NPD7028	Phase 2
0.6994	Remote Similarity	NPD5844	Phase 1
0.6988	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1510	Phase 2
0.6986	Remote Similarity	NPD5126	Approved
0.6986	Remote Similarity	NPD5125	Phase 3
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4110	Phase 3
0.6974	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7411	Suspended
0.6962	Remote Similarity	NPD5958	Discontinued
0.6962	Remote Similarity	NPD1549	Phase 2
0.6959	Remote Similarity	NPD1608	Approved
0.6957	Remote Similarity	NPD6799	Approved
0.6946	Remote Similarity	NPD5402	Approved
0.6946	Remote Similarity	NPD3817	Phase 2
0.6943	Remote Similarity	NPD2935	Discontinued
0.6933	Remote Similarity	NPD3094	Phase 2
0.6919	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6166	Phase 2
0.6918	Remote Similarity	NPD6674	Discontinued
0.6914	Remote Similarity	NPD5401	Approved
0.6914	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6599	Discontinued
0.6905	Remote Similarity	NPD7768	Phase 2
0.6899	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7435	Discontinued
0.6894	Remote Similarity	NPD7236	Approved
0.6894	Remote Similarity	NPD5058	Phase 3
0.6887	Remote Similarity	NPD2798	Approved
0.6883	Remote Similarity	NPD4062	Phase 3
0.6879	Remote Similarity	NPD7473	Discontinued
0.6875	Remote Similarity	NPD7157	Approved
0.6872	Remote Similarity	NPD8434	Phase 2
0.6872	Remote Similarity	NPD8150	Discontinued
0.6871	Remote Similarity	NPD3019	Approved
0.6871	Remote Similarity	NPD2932	Approved
0.6867	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1876	Approved
0.6865	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7095	Approved
0.6863	Remote Similarity	NPD3027	Phase 3
0.6862	Remote Similarity	NPD8320	Phase 1
0.6862	Remote Similarity	NPD8319	Approved
0.6855	Remote Similarity	NPD2424	Discontinued
0.6842	Remote Similarity	NPD7585	Approved
0.6839	Remote Similarity	NPD4060	Phase 1
0.6839	Remote Similarity	NPD4140	Approved
0.6839	Remote Similarity	NPD3751	Discontinued
0.6835	Remote Similarity	NPD2438	Suspended
0.6835	Remote Similarity	NPD6685	Approved
0.6835	Remote Similarity	NPD2796	Approved
0.6831	Remote Similarity	NPD969	Suspended
0.6821	Remote Similarity	NPD3267	Approved
0.6821	Remote Similarity	NPD3266	Approved
0.6821	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD5909	Discontinued
0.681	Remote Similarity	NPD2533	Approved
0.681	Remote Similarity	NPD2534	Approved
0.681	Remote Similarity	NPD2532	Approved
0.6809	Remote Similarity	NPD2067	Discontinued
0.6809	Remote Similarity	NPD7680	Approved
0.6806	Remote Similarity	NPD2629	Approved
0.6806	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7930	Approved
0.6802	Remote Similarity	NPD6232	Discontinued
0.68	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4908	Phase 1
0.6795	Remote Similarity	NPD4340	Discontinued
0.679	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7583	Approved
0.6788	Remote Similarity	NPD7239	Suspended
0.6786	Remote Similarity	NPD2801	Approved
0.6786	Remote Similarity	NPD1358	Approved
0.6786	Remote Similarity	NPD1465	Phase 2
0.6786	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7843	Approved
0.6779	Remote Similarity	NPD3092	Approved
0.6779	Remote Similarity	NPD422	Phase 1
0.6779	Remote Similarity	NPD3705	Approved
0.6774	Remote Similarity	NPD8032	Phase 2
0.6772	Remote Similarity	NPD2799	Discontinued
0.6772	Remote Similarity	NPD3748	Approved
0.676	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD17	Approved
0.6755	Remote Similarity	NPD3225	Approved
0.675	Remote Similarity	NPD4534	Discontinued
0.6747	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6535	Approved
0.6739	Remote Similarity	NPD6534	Approved
0.6739	Remote Similarity	NPD6647	Phase 2
0.6738	Remote Similarity	NPD6776	Approved
0.6738	Remote Similarity	NPD6779	Approved
0.6738	Remote Similarity	NPD6778	Approved
0.6738	Remote Similarity	NPD6777	Approved
0.6738	Remote Similarity	NPD6780	Approved
0.6738	Remote Similarity	NPD6781	Approved
0.6738	Remote Similarity	NPD6782	Approved
0.6737	Remote Similarity	NPD7999	Approved
0.6735	Remote Similarity	NPD7741	Discontinued
0.6731	Remote Similarity	NPD1240	Approved
0.6731	Remote Similarity	NPD1613	Approved
0.6731	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6099	Approved
0.673	Remote Similarity	NPD6100	Approved
0.672	Remote Similarity	NPD7700	Phase 2
0.672	Remote Similarity	NPD7699	Phase 2
0.6719	Remote Similarity	NPD8151	Discontinued
0.6714	Remote Similarity	NPD3134	Approved
0.6712	Remote Similarity	NPD9493	Approved
0.671	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7410	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