NPASS Compound

Structure

CID55608 OpenBabel06191715392D 41 44 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 -5.1962 0.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 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 -1.7321 0.0000 0.0000 C 0 0 2 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 1.7321 1.0000 0.0000 C 0 0 1 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 1.5000 0.0000 C 0 0 2 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 1.7321 -0.0000 0.0000 C 0 0 1 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 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 4.3301 -1.5000 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 2.5000 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 3.4641 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 -3.4641 0.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 36 1 0 0 0 0 9 27 1 0 0 0 0 10 1 1 1 0 0 0 10 15 1 0 0 0 0 10 37 1 0 0 0 0 11 2 1 6 0 0 0 11 22 1 0 0 0 0 11 38 1 0 0 0 0 13 28 1 0 0 0 0 14 9 1 1 0 0 0 14 16 1 0 0 0 0 14 39 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 6 0 0 0 16 23 1 0 0 0 0 16 30 1 6 0 0 0 17 19 1 0 0 0 0 17 31 1 1 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 6 0 0 0 19 25 1 0 0 0 0 19 33 1 1 0 0 0 20 26 1 0 0 0 0 20 34 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 21 35 1 6 0 0 0 22 40 1 1 0 0 0 23 41 1 1 0 0 0 24 36 1 1 0 0 0 24 39 1 0 0 0 0 25 37 1 0 0 0 0 25 40 1 6 0 0 0 26 38 1 0 0 0 0 26 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.24
Volume:	547.97
LogP:	-0.856
LogD:	-1.28
LogS:	-2.245
# Rotatable Bonds:	9
TPSA:	237.45
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.135
Synthetic Accessibility Score:	4.905
Fsp3:	0.769
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.481
MDCK Permeability:	0.00011598761921050027
Pgp-inhibitor:	0.006
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	44.00046920776367%
Volume Distribution (VD):	0.283
Pgp-substrate:	38.5693359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	0.654
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.437
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.931
Carcinogencity:	0.046
Eye Corrosion:	0.004
Eye Irritation:	0.069
Respiratory Toxicity:	0.064

Download Data

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

Natural Product: NPC55608

Natural Product ID:	NPC55608
*Common Name:**	Ligurobustoside M
IUPAC Name:	(2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxan-4-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms:	ligurobustoside M
Standard InCHIKey:	PZNQCWWNVMGWAG-MWLFWLFYSA-N
Standard InCHI:	InChI=1S/C26H40O15/c1-10-15(29)17(31)19(33)25(37-10)40-22-11(2)38-26(20(34)18(22)32)41-23-16(30)14(9-27)39-24(21(23)35)36-8-7-12-3-5-13(28)6-4-12/h3-6,10-11,14-35H,7-9H2,1-2H3/t10-,11-,14+,15-,16+,17+,18-,19+,20+,21+,22-,23-,24+,25-,26-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@H](C)O[C@H]([C@@H]([C@@H]1O)O)O[C@H]1[C@@H]([C@@H](CO)O[C@H]([C@@H]1O)OCCc1ccc(cc1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448458
PubChem CID:	10371226
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO2726	Ligustrum robustum	Species	Oleaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828473]
NPO2726	Ligustrum robustum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	=	134100.0	nM	PMID[561910]

☑ 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 NPC55608 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	304
0.1-0.2	1252
0.2-0.3	3076
0.3-0.4	8721
0.4-0.5	9820
0.5-0.6	11204
0.6-0.7	6908
0.7-0.8	1190
0.8-0.85	148
0.85-0.9	66
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9483	High Similarity	NPC282409
0.9483	High Similarity	NPC469702
0.9474	High Similarity	NPC148055
0.9402	High Similarity	NPC469548
0.9402	High Similarity	NPC476448
0.9402	High Similarity	NPC201402
0.9402	High Similarity	NPC476445
0.9402	High Similarity	NPC160854
0.9402	High Similarity	NPC469703
0.9402	High Similarity	NPC469704
0.9322	High Similarity	NPC469686
0.9298	High Similarity	NPC157338
0.9244	High Similarity	NPC471067
0.9167	High Similarity	NPC232454
0.9167	High Similarity	NPC178449
0.9167	High Similarity	NPC470907
0.904	High Similarity	NPC46137
0.904	High Similarity	NPC235294
0.9032	High Similarity	NPC184092
0.8974	High Similarity	NPC175771
0.8966	High Similarity	NPC313193
0.8926	High Similarity	NPC476142
0.8906	High Similarity	NPC263829
0.8889	High Similarity	NPC138777
0.8889	High Similarity	NPC225384
0.8889	High Similarity	NPC246869
0.8871	High Similarity	NPC79715
0.8871	High Similarity	NPC469687
0.8871	High Similarity	NPC106677
0.8871	High Similarity	NPC231607
0.8871	High Similarity	NPC108659
0.8871	High Similarity	NPC264900
0.8843	High Similarity	NPC266045
0.8819	High Similarity	NPC254275
0.879	High Similarity	NPC94179
0.873	High Similarity	NPC469549
0.872	High Similarity	NPC288416
0.871	High Similarity	NPC90318
0.8682	High Similarity	NPC35731
0.8661	High Similarity	NPC470122
0.8661	High Similarity	NPC17968
0.8661	High Similarity	NPC469705
0.8651	High Similarity	NPC148982
0.864	High Similarity	NPC471157
0.8626	High Similarity	NPC476376
0.8626	High Similarity	NPC101686
0.8626	High Similarity	NPC469364
0.8626	High Similarity	NPC65262
0.8618	High Similarity	NPC52097
0.8594	High Similarity	NPC478255
0.8571	High Similarity	NPC45224
0.8571	High Similarity	NPC471881
0.8571	High Similarity	NPC156692
0.8571	High Similarity	NPC35288
0.8571	High Similarity	NPC173150
0.8571	High Similarity	NPC471882
0.8561	High Similarity	NPC476383
0.8561	High Similarity	NPC81515
0.8561	High Similarity	NPC64141
0.8561	High Similarity	NPC89105
0.8561	High Similarity	NPC472350
0.8561	High Similarity	NPC68092
0.8561	High Similarity	NPC197316
0.856	High Similarity	NPC83218
0.856	High Similarity	NPC126991
0.8548	High Similarity	NPC212176
0.8538	High Similarity	NPC169398
0.8537	High Similarity	NPC11724
0.8527	High Similarity	NPC471095
0.8527	High Similarity	NPC471066
0.8507	High Similarity	NPC265648
0.8507	High Similarity	NPC222433
0.8504	High Similarity	NPC158673
0.8504	High Similarity	NPC225307
0.85	High Similarity	NPC301651
0.85	High Similarity	NPC473556
0.8492	Intermediate Similarity	NPC252114
0.8492	Intermediate Similarity	NPC61181
0.8485	Intermediate Similarity	NPC260425
0.8485	Intermediate Similarity	NPC304152
0.8485	Intermediate Similarity	NPC262328
0.8485	Intermediate Similarity	NPC87777
0.8462	Intermediate Similarity	NPC30563
0.8462	Intermediate Similarity	NPC164172
0.8455	Intermediate Similarity	NPC469412
0.8455	Intermediate Similarity	NPC198734
0.8455	Intermediate Similarity	NPC269242
0.8455	Intermediate Similarity	NPC476872
0.845	Intermediate Similarity	NPC65942
0.845	Intermediate Similarity	NPC248307
0.8444	Intermediate Similarity	NPC247032
0.8444	Intermediate Similarity	NPC476381
0.8444	Intermediate Similarity	NPC264632
0.8444	Intermediate Similarity	NPC76406
0.8444	Intermediate Similarity	NPC119537
0.8444	Intermediate Similarity	NPC476375
0.8444	Intermediate Similarity	NPC96795
0.8444	Intermediate Similarity	NPC269141
0.8444	Intermediate Similarity	NPC476397
0.8444	Intermediate Similarity	NPC112
0.8444	Intermediate Similarity	NPC476378
0.8444	Intermediate Similarity	NPC298257
0.8444	Intermediate Similarity	NPC205864
0.8444	Intermediate Similarity	NPC175214
0.8444	Intermediate Similarity	NPC476380
0.8444	Intermediate Similarity	NPC476384
0.8433	Intermediate Similarity	NPC476385
0.8433	Intermediate Similarity	NPC47471
0.8433	Intermediate Similarity	NPC134405
0.8433	Intermediate Similarity	NPC476377
0.8425	Intermediate Similarity	NPC103533
0.8421	Intermediate Similarity	NPC205195
0.8409	Intermediate Similarity	NPC3293
0.8409	Intermediate Similarity	NPC40664
0.8409	Intermediate Similarity	NPC177035
0.8409	Intermediate Similarity	NPC199459
0.8409	Intermediate Similarity	NPC138350
0.8409	Intermediate Similarity	NPC165482
0.8409	Intermediate Similarity	NPC52277
0.8409	Intermediate Similarity	NPC197723
0.8385	Intermediate Similarity	NPC473285
0.8382	Intermediate Similarity	NPC225445
0.8382	Intermediate Similarity	NPC64195
0.8376	Intermediate Similarity	NPC474148
0.8376	Intermediate Similarity	NPC276061
0.8374	Intermediate Similarity	NPC469708
0.8374	Intermediate Similarity	NPC60589
0.8358	Intermediate Similarity	NPC475530
0.8358	Intermediate Similarity	NPC473799
0.8358	Intermediate Similarity	NPC106944
0.8346	Intermediate Similarity	NPC78363
0.8346	Intermediate Similarity	NPC470413
0.8346	Intermediate Similarity	NPC138738
0.8333	Intermediate Similarity	NPC287429
0.8333	Intermediate Similarity	NPC238243
0.8321	Intermediate Similarity	NPC28637
0.8309	Intermediate Similarity	NPC113680
0.8309	Intermediate Similarity	NPC278961
0.8309	Intermediate Similarity	NPC116922
0.8308	Intermediate Similarity	NPC476407
0.8308	Intermediate Similarity	NPC9912
0.8308	Intermediate Similarity	NPC475824
0.8296	Intermediate Similarity	NPC273932
0.8296	Intermediate Similarity	NPC89686
0.8296	Intermediate Similarity	NPC257095
0.8295	Intermediate Similarity	NPC253595
0.8295	Intermediate Similarity	NPC307110
0.8271	Intermediate Similarity	NPC469383
0.8268	Intermediate Similarity	NPC123704
0.8261	Intermediate Similarity	NPC229505
0.8258	Intermediate Similarity	NPC470881
0.8258	Intermediate Similarity	NPC287597
0.8258	Intermediate Similarity	NPC34293
0.8258	Intermediate Similarity	NPC886
0.8258	Intermediate Similarity	NPC187194
0.8258	Intermediate Similarity	NPC130496
0.8258	Intermediate Similarity	NPC188555
0.8248	Intermediate Similarity	NPC196063
0.8248	Intermediate Similarity	NPC300894
0.8248	Intermediate Similarity	NPC141455
0.8248	Intermediate Similarity	NPC296954
0.8248	Intermediate Similarity	NPC177597
0.8235	Intermediate Similarity	NPC230718
0.8235	Intermediate Similarity	NPC49542
0.8235	Intermediate Similarity	NPC84207
0.8235	Intermediate Similarity	NPC128337
0.8235	Intermediate Similarity	NPC5253
0.8235	Intermediate Similarity	NPC139976
0.8231	Intermediate Similarity	NPC472024
0.8231	Intermediate Similarity	NPC80600
0.8209	Intermediate Similarity	NPC469696
0.8201	Intermediate Similarity	NPC232992
0.8195	Intermediate Similarity	NPC79957
0.8195	Intermediate Similarity	NPC123988
0.8188	Intermediate Similarity	NPC476382
0.8188	Intermediate Similarity	NPC252292
0.8188	Intermediate Similarity	NPC34927
0.8188	Intermediate Similarity	NPC34587
0.8188	Intermediate Similarity	NPC100998
0.8182	Intermediate Similarity	NPC294166
0.8182	Intermediate Similarity	NPC6836
0.8182	Intermediate Similarity	NPC115022
0.8175	Intermediate Similarity	NPC105005
0.8175	Intermediate Similarity	NPC204644
0.8168	Intermediate Similarity	NPC475067
0.8168	Intermediate Similarity	NPC281798
0.8168	Intermediate Similarity	NPC254819
0.8167	Intermediate Similarity	NPC290353
0.8167	Intermediate Similarity	NPC42911
0.8167	Intermediate Similarity	NPC153795
0.8162	Intermediate Similarity	NPC472711
0.8154	Intermediate Similarity	NPC295970
0.8154	Intermediate Similarity	NPC477294
0.8154	Intermediate Similarity	NPC270849
0.8154	Intermediate Similarity	NPC248355
0.8154	Intermediate Similarity	NPC166040
0.8154	Intermediate Similarity	NPC26653
0.8154	Intermediate Similarity	NPC477293
0.8154	Intermediate Similarity	NPC97326
0.8154	Intermediate Similarity	NPC229784

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 NPC55608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	747
0.2-0.3	1567
0.3-0.4	3157
0.4-0.5	1907
0.5-0.6	1207
0.6-0.7	290
0.7-0.8	15
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
0.8561	High Similarity	NPD7266	Discontinued
0.8095	Intermediate Similarity	NPD1091	Approved
0.744	Intermediate Similarity	NPD7843	Approved
0.7414	Intermediate Similarity	NPD2933	Approved
0.7414	Intermediate Similarity	NPD2934	Approved
0.7385	Intermediate Similarity	NPD5126	Approved
0.7385	Intermediate Similarity	NPD5125	Phase 3
0.7353	Intermediate Similarity	NPD3027	Phase 3
0.735	Intermediate Similarity	NPD2859	Approved
0.735	Intermediate Similarity	NPD2860	Approved
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD6674	Discontinued
0.7266	Intermediate Similarity	NPD7157	Approved
0.7258	Intermediate Similarity	NPD2684	Approved
0.7241	Intermediate Similarity	NPD5058	Phase 3
0.723	Intermediate Similarity	NPD1653	Approved
0.7194	Intermediate Similarity	NPD1613	Approved
0.7194	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD846	Approved
0.719	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD940	Approved
0.7185	Intermediate Similarity	NPD3094	Phase 2
0.717	Intermediate Similarity	NPD7074	Phase 3
0.7167	Intermediate Similarity	NPD3020	Approved
0.7163	Intermediate Similarity	NPD7097	Phase 1
0.7163	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD3705	Approved
0.7121	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7054	Approved
0.7063	Intermediate Similarity	NPD3022	Approved
0.7063	Intermediate Similarity	NPD3021	Approved
0.7063	Intermediate Similarity	NPD7472	Approved
0.705	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1357	Approved
0.7044	Intermediate Similarity	NPD7228	Approved
0.7042	Intermediate Similarity	NPD4536	Approved
0.7042	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4538	Approved
0.704	Intermediate Similarity	NPD290	Approved
0.7015	Intermediate Similarity	NPD3092	Approved
0.6985	Remote Similarity	NPD8651	Approved
0.6975	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7251	Discontinued
0.697	Remote Similarity	NPD1548	Phase 1
0.6957	Remote Similarity	NPD2861	Phase 2
0.6939	Remote Similarity	NPD6190	Approved
0.6933	Remote Similarity	NPD7808	Phase 3
0.693	Remote Similarity	NPD111	Approved
0.6929	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD6797	Phase 2
0.6912	Remote Similarity	NPD4659	Approved
0.6906	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1610	Phase 2
0.6879	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD5960	Phase 3
0.6875	Remote Similarity	NPD5588	Approved
0.6842	Remote Similarity	NPD3091	Approved
0.6835	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3028	Approved
0.6829	Remote Similarity	NPD1242	Phase 1
0.6822	Remote Similarity	NPD228	Approved
0.6822	Remote Similarity	NPD969	Suspended
0.6812	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4103	Phase 2
0.6803	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4380	Phase 2
0.6788	Remote Similarity	NPD3685	Discontinued
0.6783	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5124	Phase 1
0.6768	Remote Similarity	NPD7685	Pre-registration
0.6767	Remote Similarity	NPD856	Approved
0.6767	Remote Similarity	NPD16	Approved
0.6761	Remote Similarity	NPD6407	Approved
0.6761	Remote Similarity	NPD6405	Approved
0.6742	Remote Similarity	NPD6671	Approved
0.6741	Remote Similarity	NPD5846	Approved
0.6741	Remote Similarity	NPD6516	Phase 2
0.6741	Remote Similarity	NPD9381	Approved
0.6741	Remote Similarity	NPD9384	Approved
0.6718	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD9545	Approved
0.6715	Remote Similarity	NPD2561	Approved
0.6715	Remote Similarity	NPD2562	Approved
0.6714	Remote Similarity	NPD5736	Approved
0.671	Remote Similarity	NPD37	Approved
0.6709	Remote Similarity	NPD6234	Discontinued
0.6693	Remote Similarity	NPD968	Approved
0.6692	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6798	Discontinued
0.669	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4965	Approved
0.6688	Remote Similarity	NPD4966	Approved
0.6688	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7240	Approved
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD4750	Phase 3
0.6644	Remote Similarity	NPD4628	Phase 3
0.6644	Remote Similarity	NPD4108	Discontinued
0.6642	Remote Similarity	NPD422	Phase 1
0.6642	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD318	Approved
0.6642	Remote Similarity	NPD317	Approved
0.6641	Remote Similarity	NPD1358	Approved
0.6639	Remote Similarity	NPD844	Approved
0.6639	Remote Similarity	NPD1809	Phase 2
0.6627	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3818	Discontinued
0.6623	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5314	Approved
0.6621	Remote Similarity	NPD6653	Approved
0.662	Remote Similarity	NPD3179	Approved
0.662	Remote Similarity	NPD3180	Approved
0.6618	Remote Similarity	NPD3095	Discontinued
0.6612	Remote Similarity	NPD845	Approved
0.6597	Remote Similarity	NPD3062	Approved
0.6597	Remote Similarity	NPD3059	Approved
0.6597	Remote Similarity	NPD3061	Approved
0.6597	Remote Similarity	NPD4060	Phase 1
0.6593	Remote Similarity	NPD7741	Discontinued
0.6587	Remote Similarity	NPD8312	Approved
0.6587	Remote Similarity	NPD8313	Approved
0.6561	Remote Similarity	NPD2978	Approved
0.6561	Remote Similarity	NPD2977	Approved
0.656	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6355	Discontinued
0.6552	Remote Similarity	NPD5735	Approved
0.6547	Remote Similarity	NPD6582	Phase 2
0.6547	Remote Similarity	NPD6583	Phase 3
0.6547	Remote Similarity	NPD4749	Approved
0.6541	Remote Similarity	NPD7075	Discontinued
0.6533	Remote Similarity	NPD4535	Phase 3
0.6531	Remote Similarity	NPD7033	Discontinued
0.6528	Remote Similarity	NPD4062	Phase 3
0.6528	Remote Similarity	NPD6663	Approved
0.6525	Remote Similarity	NPD9619	Approved
0.6525	Remote Similarity	NPD9620	Approved
0.6525	Remote Similarity	NPD9621	Approved
0.6515	Remote Similarity	NPD5535	Approved
0.6515	Remote Similarity	NPD821	Approved
0.6513	Remote Similarity	NPD7213	Phase 3
0.6513	Remote Similarity	NPD7212	Phase 2
0.651	Remote Similarity	NPD2424	Discontinued
0.6507	Remote Similarity	NPD2568	Approved
0.6503	Remote Similarity	NPD6166	Phase 2
0.6503	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7095	Approved
0.6503	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD3620	Phase 2
0.6483	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3536	Discontinued
0.6471	Remote Similarity	NPD7447	Phase 1
0.6471	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD2229	Approved
0.6466	Remote Similarity	NPD5283	Phase 1
0.6466	Remote Similarity	NPD2234	Approved
0.6466	Remote Similarity	NPD2228	Approved
0.6458	Remote Similarity	NPD598	Approved
0.6458	Remote Similarity	NPD601	Approved
0.6458	Remote Similarity	NPD597	Approved
0.6456	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD1135	Approved
0.6454	Remote Similarity	NPD1131	Approved
0.6454	Remote Similarity	NPD1133	Approved
0.6454	Remote Similarity	NPD1134	Approved
0.6454	Remote Similarity	NPD1129	Approved
0.6452	Remote Similarity	NPD288	Approved
0.6447	Remote Similarity	NPD3122	Phase 3
0.6447	Remote Similarity	NPD5756	Phase 2
0.6443	Remote Similarity	NPD5762	Approved
0.6443	Remote Similarity	NPD5763	Approved
0.6438	Remote Similarity	NPD230	Phase 1
0.6434	Remote Similarity	NPD3134	Approved
0.6429	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2983	Phase 2
0.6429	Remote Similarity	NPD2982	Phase 2
0.6424	Remote Similarity	NPD8166	Discontinued
0.642	Remote Similarity	NPD7199	Phase 2
0.6418	Remote Similarity	NPD2629	Approved
0.6418	Remote Similarity	NPD9618	Approved
0.6418	Remote Similarity	NPD9614	Approved
0.6416	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD1130	Approved
0.6414	Remote Similarity	NPD1132	Approved
0.6414	Remote Similarity	NPD1136	Approved
0.6412	Remote Similarity	NPD5451	Approved
0.6412	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6584	Phase 3
0.6408	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD9608	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