NPASS Compound

Structure

CID321285 OpenBabel06191716152D 28 29 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 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 0.0000 -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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 2 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 -4.3301 -1.5000 0.0000 C 0 0 2 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 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 11 1 0 0 0 0 7 17 1 0 0 0 0 9 24 1 0 0 0 0 10 7 1 6 0 0 0 10 12 1 0 0 0 0 10 25 1 0 0 0 0 11 16 2 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 1 0 0 0 13 14 1 0 0 0 0 13 19 1 6 0 0 0 14 15 1 0 0 0 0 14 20 1 1 0 0 0 15 25 1 0 0 0 0 15 27 1 6 0 0 0 16 26 1 0 0 0 0 21 28 1 0 0 0 0 22 28 2 0 0 0 0 23 28 2 0 0 0 0 26 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	439.06
Volume:	376.255
LogP:	-0.386
LogD:	-0.902
LogS:	-0.664
# Rotatable Bonds:	8
TPSA:	175.34
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	4.155
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.007
MDCK Permeability:	2.8334765374893323e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.555
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	93.07362365722656%
Volume Distribution (VD):	0.646
Pgp-substrate:	6.453263759613037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.824
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	1.376
Half-life (T1/2):	0.744

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.753
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.114
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC321285

Natural Product ID:	NPC321285
*Common Name:**	Glucolimnanthin
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z)-2-(3-methoxyphenyl)-N-sulfooxyethanimidothioate
Synonyms:	Glucolimnanthin
Standard InCHIKey:	RYDIUEJGEAUJAI-OOMJLXHVSA-N
Standard InCHI:	InChI=1S/C15H21NO10S2/c1-24-9-4-2-3-8(5-9)6-11(16-26-28(21,22)23)27-15-14(20)13(19)12(18)10(7-17)25-15/h2-5,10,12-15,17-20H,6-7H2,1H3,(H,21,22,23)/b16-11-/t10-,12-,13+,14-,15+/m1/s1
SMILES:	OC[C@H]1O[C@@H](S/C(=NOS(=O)(=O)O)/Cc2cccc(c2)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463456
PubChem CID:	20843359
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0001540] Monosaccharides [CHEMONTID:0001498] Hexoses [CHEMONTID:0000373] Glucosinolates [CHEMONTID:0003925] Alkylglucosinolates

*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
NPO5653	Limnanthes alba	Species	Limnanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19170637]
NPO5653	Limnanthes alba	Species	Limnanthaceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	71.0	%	PMID[469163]

☑ 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 NPC321285 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	208
0.1-0.2	1286
0.2-0.3	5239
0.3-0.4	13510
0.4-0.5	5670
0.5-0.6	12699
0.6-0.7	3892
0.7-0.8	192
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7518	Intermediate Similarity	NPC135961
0.7482	Intermediate Similarity	NPC470804
0.7452	Intermediate Similarity	NPC150670
0.741	Intermediate Similarity	NPC473875
0.7379	Intermediate Similarity	NPC472024
0.7379	Intermediate Similarity	NPC80600
0.7361	Intermediate Similarity	NPC245826
0.7361	Intermediate Similarity	NPC252307
0.7361	Intermediate Similarity	NPC474178
0.7357	Intermediate Similarity	NPC476343
0.7338	Intermediate Similarity	NPC148615
0.7338	Intermediate Similarity	NPC35071
0.7338	Intermediate Similarity	NPC177475
0.7329	Intermediate Similarity	NPC475067
0.7329	Intermediate Similarity	NPC65942
0.7329	Intermediate Similarity	NPC248307
0.7324	Intermediate Similarity	NPC293701
0.7324	Intermediate Similarity	NPC114901
0.7324	Intermediate Similarity	NPC109822
0.7324	Intermediate Similarity	NPC48990
0.7324	Intermediate Similarity	NPC94276
0.7319	Intermediate Similarity	NPC329980
0.731	Intermediate Similarity	NPC26653
0.731	Intermediate Similarity	NPC97326
0.731	Intermediate Similarity	NPC5851
0.731	Intermediate Similarity	NPC270849
0.731	Intermediate Similarity	NPC86030
0.731	Intermediate Similarity	NPC166040
0.7305	Intermediate Similarity	NPC71090
0.7305	Intermediate Similarity	NPC476142
0.7305	Intermediate Similarity	NPC209567
0.7292	Intermediate Similarity	NPC41706
0.7292	Intermediate Similarity	NPC111247
0.7292	Intermediate Similarity	NPC118787
0.7292	Intermediate Similarity	NPC163332
0.7292	Intermediate Similarity	NPC198798
0.7292	Intermediate Similarity	NPC183181
0.7292	Intermediate Similarity	NPC292056
0.7292	Intermediate Similarity	NPC147821
0.7292	Intermediate Similarity	NPC319625
0.7266	Intermediate Similarity	NPC320987
0.7266	Intermediate Similarity	NPC181969
0.7241	Intermediate Similarity	NPC470084
0.7241	Intermediate Similarity	NPC302378
0.7241	Intermediate Similarity	NPC40377
0.7241	Intermediate Similarity	NPC72529
0.7222	Intermediate Similarity	NPC191037
0.7222	Intermediate Similarity	NPC178284
0.7222	Intermediate Similarity	NPC58607
0.7222	Intermediate Similarity	NPC206882
0.7214	Intermediate Similarity	NPC469708
0.7214	Intermediate Similarity	NPC60589
0.7211	Intermediate Similarity	NPC469625
0.7211	Intermediate Similarity	NPC469613
0.7211	Intermediate Similarity	NPC30043
0.7211	Intermediate Similarity	NPC9912
0.7211	Intermediate Similarity	NPC470095
0.7211	Intermediate Similarity	NPC470096
0.72	Intermediate Similarity	NPC14600
0.72	Intermediate Similarity	NPC41473
0.72	Intermediate Similarity	NPC204848
0.72	Intermediate Similarity	NPC160607
0.72	Intermediate Similarity	NPC312770
0.7194	Intermediate Similarity	NPC283616
0.7194	Intermediate Similarity	NPC474214
0.7194	Intermediate Similarity	NPC255675
0.7192	Intermediate Similarity	NPC218856
0.7192	Intermediate Similarity	NPC248355
0.7192	Intermediate Similarity	NPC210623
0.7192	Intermediate Similarity	NPC470258
0.7192	Intermediate Similarity	NPC226788
0.7192	Intermediate Similarity	NPC3439
0.7192	Intermediate Similarity	NPC202582
0.7192	Intermediate Similarity	NPC285339
0.7192	Intermediate Similarity	NPC190629
0.7192	Intermediate Similarity	NPC475875
0.7192	Intermediate Similarity	NPC273295
0.7192	Intermediate Similarity	NPC307110
0.7192	Intermediate Similarity	NPC222004
0.719	Intermediate Similarity	NPC63628
0.719	Intermediate Similarity	NPC178466
0.7181	Intermediate Similarity	NPC187194
0.7181	Intermediate Similarity	NPC35731
0.7181	Intermediate Similarity	NPC170694
0.7181	Intermediate Similarity	NPC470881
0.7179	Intermediate Similarity	NPC471032
0.7179	Intermediate Similarity	NPC470935
0.7172	Intermediate Similarity	NPC118533
0.7172	Intermediate Similarity	NPC165045
0.7172	Intermediate Similarity	NPC474119
0.7171	Intermediate Similarity	NPC123761
0.7163	Intermediate Similarity	NPC269242
0.7163	Intermediate Similarity	NPC469412
0.7163	Intermediate Similarity	NPC183262
0.7163	Intermediate Similarity	NPC198734
0.7162	Intermediate Similarity	NPC253105
0.7162	Intermediate Similarity	NPC7903
0.7162	Intermediate Similarity	NPC35932
0.7162	Intermediate Similarity	NPC184447
0.7162	Intermediate Similarity	NPC201587
0.7162	Intermediate Similarity	NPC16208
0.7162	Intermediate Similarity	NPC160991
0.7153	Intermediate Similarity	NPC194519
0.7153	Intermediate Similarity	NPC12308
0.7143	Intermediate Similarity	NPC474320
0.7143	Intermediate Similarity	NPC24474
0.7143	Intermediate Similarity	NPC257582
0.7143	Intermediate Similarity	NPC242807
0.7143	Intermediate Similarity	NPC153739
0.7143	Intermediate Similarity	NPC311595
0.7143	Intermediate Similarity	NPC477804
0.7143	Intermediate Similarity	NPC469612
0.7143	Intermediate Similarity	NPC469614
0.7143	Intermediate Similarity	NPC64201
0.7143	Intermediate Similarity	NPC241522
0.7143	Intermediate Similarity	NPC42300
0.7143	Intermediate Similarity	NPC187998
0.7143	Intermediate Similarity	NPC262606
0.7143	Intermediate Similarity	NPC174495
0.7143	Intermediate Similarity	NPC251306
0.7143	Intermediate Similarity	NPC77040
0.7143	Intermediate Similarity	NPC145305
0.7143	Intermediate Similarity	NPC194034
0.7143	Intermediate Similarity	NPC92164
0.7133	Intermediate Similarity	NPC471693
0.7133	Intermediate Similarity	NPC474130
0.7133	Intermediate Similarity	NPC165375
0.7133	Intermediate Similarity	NPC220598
0.7114	Intermediate Similarity	NPC25821
0.7114	Intermediate Similarity	NPC215833
0.7114	Intermediate Similarity	NPC263064
0.7114	Intermediate Similarity	NPC69513
0.7114	Intermediate Similarity	NPC170185
0.7114	Intermediate Similarity	NPC6836
0.7113	Intermediate Similarity	NPC226712
0.7113	Intermediate Similarity	NPC343720
0.7113	Intermediate Similarity	NPC324571
0.7113	Intermediate Similarity	NPC54872
0.7113	Intermediate Similarity	NPC184651
0.7113	Intermediate Similarity	NPC473853
0.7113	Intermediate Similarity	NPC312675
0.7113	Intermediate Similarity	NPC262156
0.7113	Intermediate Similarity	NPC113865
0.7113	Intermediate Similarity	NPC470212
0.7111	Intermediate Similarity	NPC46844
0.7111	Intermediate Similarity	NPC137685
0.7095	Intermediate Similarity	NPC166168
0.7095	Intermediate Similarity	NPC277804
0.7095	Intermediate Similarity	NPC472597
0.7086	Intermediate Similarity	NPC177035
0.7086	Intermediate Similarity	NPC52277
0.7086	Intermediate Similarity	NPC199459
0.7083	Intermediate Similarity	NPC287429
0.7078	Intermediate Similarity	NPC477800
0.7078	Intermediate Similarity	NPC477799
0.7078	Intermediate Similarity	NPC477794
0.7075	Intermediate Similarity	NPC170844
0.7075	Intermediate Similarity	NPC476968
0.7071	Intermediate Similarity	NPC63083
0.7067	Intermediate Similarity	NPC476411
0.7067	Intermediate Similarity	NPC251981
0.7067	Intermediate Similarity	NPC13745
0.7067	Intermediate Similarity	NPC135127
0.7067	Intermediate Similarity	NPC48863
0.7067	Intermediate Similarity	NPC107478
0.7067	Intermediate Similarity	NPC310854
0.7067	Intermediate Similarity	NPC264956
0.7063	Intermediate Similarity	NPC46586
0.7063	Intermediate Similarity	NPC204535
0.7059	Intermediate Similarity	NPC195814
0.7059	Intermediate Similarity	NPC266650
0.7055	Intermediate Similarity	NPC46067
0.7055	Intermediate Similarity	NPC5428
0.7055	Intermediate Similarity	NPC242032
0.705	Intermediate Similarity	NPC473556
0.705	Intermediate Similarity	NPC301651
0.705	Intermediate Similarity	NPC154256
0.705	Intermediate Similarity	NPC290470
0.705	Intermediate Similarity	NPC221049
0.7047	Intermediate Similarity	NPC252833
0.7047	Intermediate Similarity	NPC162093
0.7047	Intermediate Similarity	NPC470270
0.7047	Intermediate Similarity	NPC4940
0.7047	Intermediate Similarity	NPC299144
0.7042	Intermediate Similarity	NPC475529
0.7042	Intermediate Similarity	NPC207613
0.7039	Intermediate Similarity	NPC304152
0.7039	Intermediate Similarity	NPC299583
0.7039	Intermediate Similarity	NPC138738
0.7039	Intermediate Similarity	NPC470413
0.7039	Intermediate Similarity	NPC36434
0.7039	Intermediate Similarity	NPC477798
0.7039	Intermediate Similarity	NPC477797
0.7037	Intermediate Similarity	NPC474272
0.7034	Intermediate Similarity	NPC148627
0.7034	Intermediate Similarity	NPC470510
0.7029	Intermediate Similarity	NPC470837
0.7027	Intermediate Similarity	NPC472338
0.7027	Intermediate Similarity	NPC114102
0.702	Intermediate Similarity	NPC61946

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 NPC321285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	699
0.2-0.3	1423
0.3-0.4	2824
0.4-0.5	2251
0.5-0.6	1419
0.6-0.7	364
0.7-0.8	13
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
0.8333	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD821	Approved
0.7467	Intermediate Similarity	NPD1652	Phase 2
0.7329	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4739	Approved
0.7211	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4535	Phase 3
0.7188	Intermediate Similarity	NPD5929	Approved
0.7179	Intermediate Similarity	NPD2236	Approved
0.7143	Intermediate Similarity	NPD290	Approved
0.7113	Intermediate Similarity	NPD1091	Approved
0.7086	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3027	Phase 3
0.7044	Intermediate Similarity	NPD3111	Phase 1
0.7014	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD682	Discontinued
0.7007	Intermediate Similarity	NPD7843	Approved
0.7	Intermediate Similarity	NPD4340	Discontinued
0.698	Remote Similarity	NPD839	Approved
0.698	Remote Similarity	NPD840	Approved
0.6978	Remote Similarity	NPD7157	Approved
0.6963	Remote Similarity	NPD2684	Approved
0.6944	Remote Similarity	NPD2235	Phase 2
0.6944	Remote Similarity	NPD2231	Phase 2
0.6933	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1613	Approved
0.6933	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2586	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3540	Phase 1
0.6871	Remote Similarity	NPD558	Phase 2
0.6867	Remote Similarity	NPD1423	Approved
0.6863	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4319	Phase 2
0.6848	Remote Similarity	NPD6971	Discontinued
0.6835	Remote Similarity	NPD1774	Approved
0.6824	Remote Similarity	NPD1712	Approved
0.6821	Remote Similarity	NPD2238	Phase 2
0.6821	Remote Similarity	NPD1558	Phase 1
0.6818	Remote Similarity	NPD5712	Approved
0.6818	Remote Similarity	NPD3539	Phase 1
0.6815	Remote Similarity	NPD2677	Approved
0.6812	Remote Similarity	NPD228	Approved
0.6797	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4538	Approved
0.6797	Remote Similarity	NPD4536	Approved
0.6792	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7876	Discontinued
0.6768	Remote Similarity	NPD5773	Approved
0.6768	Remote Similarity	NPD5772	Approved
0.6755	Remote Similarity	NPD4062	Phase 3
0.6755	Remote Similarity	NPD2674	Phase 3
0.6752	Remote Similarity	NPD3367	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3892	Phase 2
0.675	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6390	Discontinued
0.675	Remote Similarity	NPD52	Approved
0.675	Remote Similarity	NPD7526	Approved
0.6738	Remote Similarity	NPD6671	Approved
0.6736	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2424	Discontinued
0.673	Remote Similarity	NPD6087	Phase 1
0.6723	Remote Similarity	NPD6842	Approved
0.6723	Remote Similarity	NPD6841	Approved
0.6723	Remote Similarity	NPD6843	Phase 3
0.6712	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.671	Remote Similarity	NPD2161	Phase 2
0.6689	Remote Similarity	NPD1048	Approved
0.6688	Remote Similarity	NPD4236	Phase 3
0.6688	Remote Similarity	NPD4237	Approved
0.6667	Remote Similarity	NPD600	Approved
0.6667	Remote Similarity	NPD1803	Phase 3
0.6667	Remote Similarity	NPD596	Approved
0.6667	Remote Similarity	NPD475	Phase 2
0.6667	Remote Similarity	NPD3685	Discontinued
0.6667	Remote Similarity	NPD1669	Approved
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6331	Phase 2
0.6645	Remote Similarity	NPD5960	Phase 3
0.6645	Remote Similarity	NPD4108	Discontinued
0.6645	Remote Similarity	NPD5588	Approved
0.6644	Remote Similarity	NPD4480	Approved
0.6626	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3180	Approved
0.6623	Remote Similarity	NPD3179	Approved
0.6623	Remote Similarity	NPD6653	Approved
0.6622	Remote Similarity	NPD2922	Phase 1
0.6619	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6032	Approved
0.66	Remote Similarity	NPD2861	Phase 2
0.66	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2233	Approved
0.6599	Remote Similarity	NPD2232	Approved
0.6599	Remote Similarity	NPD2230	Approved
0.6596	Remote Similarity	NPD5283	Phase 1
0.6585	Remote Similarity	NPD1642	Discontinued
0.6584	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4123	Phase 3
0.6582	Remote Similarity	NPD3060	Approved
0.6582	Remote Similarity	NPD5177	Phase 3
0.6579	Remote Similarity	NPD5110	Phase 2
0.6579	Remote Similarity	NPD3145	Approved
0.6579	Remote Similarity	NPD3144	Approved
0.6579	Remote Similarity	NPD5111	Phase 2
0.6579	Remote Similarity	NPD5109	Approved
0.6577	Remote Similarity	NPD1820	Approved
0.6577	Remote Similarity	NPD1818	Approved
0.6577	Remote Similarity	NPD1819	Approved
0.6577	Remote Similarity	NPD1817	Approved
0.6577	Remote Similarity	NPD1794	Approved
0.6569	Remote Similarity	NPD968	Approved
0.6562	Remote Similarity	NPD3122	Phase 3
0.6561	Remote Similarity	NPD5762	Approved
0.6561	Remote Similarity	NPD1375	Discontinued
0.6561	Remote Similarity	NPD3656	Approved
0.6561	Remote Similarity	NPD5763	Approved
0.6552	Remote Similarity	NPD1357	Approved
0.6543	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2154	Approved
0.6538	Remote Similarity	NPD2156	Approved
0.6538	Remote Similarity	NPD2155	Approved
0.6536	Remote Similarity	NPD7477	Discontinued
0.6533	Remote Similarity	NPD6584	Phase 3
0.6531	Remote Similarity	NPD776	Approved
0.6531	Remote Similarity	NPD3705	Approved
0.6519	Remote Similarity	NPD7153	Discontinued
0.6519	Remote Similarity	NPD291	Approved
0.6516	Remote Similarity	NPD2157	Approved
0.6516	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8651	Approved
0.6503	Remote Similarity	NPD709	Approved
0.6485	Remote Similarity	NPD4678	Approved
0.6485	Remote Similarity	NPD4675	Approved
0.6483	Remote Similarity	NPD1182	Approved
0.6478	Remote Similarity	NPD4162	Approved
0.6471	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3496	Discontinued
0.646	Remote Similarity	NPD5058	Phase 3
0.6456	Remote Similarity	NPD7266	Discontinued
0.6452	Remote Similarity	NPD5735	Approved
0.6447	Remote Similarity	NPD4908	Phase 1
0.6446	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD2983	Phase 2
0.6443	Remote Similarity	NPD4749	Approved
0.6443	Remote Similarity	NPD2982	Phase 2
0.6438	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD556	Approved
0.6429	Remote Similarity	NPD6233	Phase 2
0.6429	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2415	Discontinued
0.6429	Remote Similarity	NPD4404	Approved
0.6424	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3690	Phase 2
0.6424	Remote Similarity	NPD3691	Phase 2
0.6424	Remote Similarity	NPD4005	Discontinued
0.6419	Remote Similarity	NPD1610	Phase 2
0.641	Remote Similarity	NPD4097	Suspended
0.6405	Remote Similarity	NPD3166	Approved
0.6405	Remote Similarity	NPD1024	Discontinued
0.6405	Remote Similarity	NPD3167	Approved
0.6405	Remote Similarity	NPD3164	Approved
0.6405	Remote Similarity	NPD3165	Approved
0.6403	Remote Similarity	NPD1358	Approved
0.6402	Remote Similarity	NPD2122	Discontinued
0.6398	Remote Similarity	NPD2219	Phase 1
0.6398	Remote Similarity	NPD3692	Discontinued
0.6395	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2667	Approved
0.6395	Remote Similarity	NPD6516	Phase 2
0.6395	Remote Similarity	NPD5846	Approved
0.6395	Remote Similarity	NPD2668	Approved
0.6395	Remote Similarity	NPD1778	Approved
0.6392	Remote Similarity	NPD2531	Phase 2
0.6389	Remote Similarity	NPD6387	Discontinued
0.6387	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4060	Phase 1
0.6382	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD3018	Phase 2
0.638	Remote Similarity	NPD3985	Discontinued
0.6376	Remote Similarity	NPD2981	Phase 2
0.6376	Remote Similarity	NPD1840	Phase 2
0.6375	Remote Similarity	NPD5062	Approved
0.6375	Remote Similarity	NPD5061	Approved
0.637	Remote Similarity	NPD1548	Phase 1
0.6369	Remote Similarity	NPD5886	Approved
0.6369	Remote Similarity	NPD41	Approved
0.6369	Remote Similarity	NPD696	Discontinued
0.6364	Remote Similarity	NPD1039	Discontinued
0.6364	Remote Similarity	NPD1653	Approved
0.6364	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3687	Approved
0.6364	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3686	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