NPASS Compound

Structure

NPC470825 OpenBabel07101719242D 32 34 0 0 1 0 0 0 0 0999 V2000 -3.4641 -4.0000 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 6.0622 -1.5000 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 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -4.3301 -2.5000 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 -4.3301 -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 -3.4641 -1.0000 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 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -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 -5.1962 -1.0000 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 -3.4641 -0.0000 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 -1.7321 -1.0000 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 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 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 1 0 0 0 10 14 1 0 0 0 0 10 30 1 0 0 0 0 12 9 1 6 0 0 0 12 15 1 0 0 0 0 12 31 1 0 0 0 0 13 22 2 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 6 0 0 0 15 17 1 0 0 0 0 15 24 1 1 0 0 0 16 18 1 0 0 0 0 16 25 1 1 0 0 0 17 19 1 0 0 0 0 17 26 1 6 0 0 0 18 20 1 0 0 0 0 18 27 1 1 0 0 0 19 21 1 0 0 0 0 19 28 1 1 0 0 0 20 29 1 6 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 21 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.16
Volume:	429.613
LogP:	0.198
LogD:	-0.376
LogS:	-2.508
# Rotatable Bonds:	7
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.204
Synthetic Accessibility Score:	4.288
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
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:	-5.875
MDCK Permeability:	7.025940431049094e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.932
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	55.59855651855469%
Volume Distribution (VD):	0.556
Pgp-substrate:	26.740327835083008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.136
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.141
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.488
AMES Toxicity:	0.372
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.916
Carcinogencity:	0.102
Eye Corrosion:	0.013
Eye Irritation:	0.731
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC470825

Natural Product ID:	NPC470825
*Common Name:**	Gleditschiaside A
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	BVUBTNCZSYXLNC-SWQDJAIOSA-N
Standard InCHI:	InChI=1S/C21H28O11/c1-10-14(23)16(25)18(27)20(30-10)29-9-12-15(24)17(26)19(28)21(31-12)32-13(22)8-7-11-5-3-2-4-6-11/h2-8,10,12,14-21,23-28H,9H2,1H3/b8-7+/t10-,12+,14-,15+,16+,17-,18+,19+,20+,21-/m0/s1
SMILES:	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(=O)C=CC3=CC=CC=C3)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2253067
PubChem CID:	76319177
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters [CHEMONTID:0003479] O-cinnamoyl 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
NPO15650	Picea neoveitchii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22901896]
NPO15650	Picea neoveitchii	Species	Pinaceae	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	9

Activity Type	# Activity
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1493	Organism	Ceratocystis paradoxa	Ceratocystis paradoxa	GI	=	0.0	%	PMID[459960]
NPT1494	Organism	Alternaria mali	Alternaria mali	GI	=	0.0	%	PMID[459960]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	GI	=	0.0	%	PMID[459960]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	GI	=	0.0	%	PMID[459960]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	62.2	%	PMID[459960]
NPT1493	Organism	Ceratocystis paradoxa	Ceratocystis paradoxa	IZ	=	0.0	mm	PMID[459960]
NPT1494	Organism	Alternaria mali	Alternaria mali	IZ	=	0.0	mm	PMID[459960]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	IZ	=	0.0	mm	PMID[459960]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	IZ	=	0.0	mm	PMID[459960]

☑ 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 NPC470825 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	203
0.1-0.2	922
0.2-0.3	2387
0.3-0.4	7225
0.4-0.5	12975
0.5-0.6	14865
0.6-0.7	3492
0.7-0.8	539
0.8-0.85	54
0.85-0.9	30
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC184633
0.9439	High Similarity	NPC474641
0.934	High Similarity	NPC43584
0.9223	High Similarity	NPC469527
0.8957	High Similarity	NPC140561
0.8957	High Similarity	NPC141970
0.8829	High Similarity	NPC29607
0.8807	High Similarity	NPC30563
0.8803	High Similarity	NPC87153
0.8803	High Similarity	NPC162925
0.8783	High Similarity	NPC229600
0.8729	High Similarity	NPC28069
0.8729	High Similarity	NPC77651
0.8716	High Similarity	NPC276061
0.8716	High Similarity	NPC474148
0.8655	High Similarity	NPC35338
0.8655	High Similarity	NPC290276
0.8655	High Similarity	NPC10883
0.8655	High Similarity	NPC231888
0.8655	High Similarity	NPC63404
0.8655	High Similarity	NPC92283
0.8655	High Similarity	NPC198918
0.8655	High Similarity	NPC124878
0.8655	High Similarity	NPC204214
0.8655	High Similarity	NPC10121
0.8644	High Similarity	NPC145287
0.8583	High Similarity	NPC471025
0.8583	High Similarity	NPC231627
0.8583	High Similarity	NPC106677
0.8512	High Similarity	NPC226101
0.8512	High Similarity	NPC471024
0.8512	High Similarity	NPC237182
0.85	High Similarity	NPC114096
0.85	High Similarity	NPC267733
0.85	High Similarity	NPC276047
0.85	High Similarity	NPC471157
0.8475	Intermediate Similarity	NPC52097
0.8448	Intermediate Similarity	NPC476096
0.843	Intermediate Similarity	NPC148026
0.8417	Intermediate Similarity	NPC126991
0.8417	Intermediate Similarity	NPC83218
0.839	Intermediate Similarity	NPC11724
0.8349	Intermediate Similarity	NPC37714
0.8349	Intermediate Similarity	NPC152384
0.8347	Intermediate Similarity	NPC147032
0.8347	Intermediate Similarity	NPC252114
0.8333	Intermediate Similarity	NPC57607
0.8306	Intermediate Similarity	NPC235294
0.8306	Intermediate Similarity	NPC246869
0.8306	Intermediate Similarity	NPC138777
0.8306	Intermediate Similarity	NPC225384
0.8306	Intermediate Similarity	NPC46137
0.8305	Intermediate Similarity	NPC476872
0.8304	Intermediate Similarity	NPC264784
0.8279	Intermediate Similarity	NPC173150
0.8279	Intermediate Similarity	NPC156692
0.8279	Intermediate Similarity	NPC471882
0.8279	Intermediate Similarity	NPC471881
0.8279	Intermediate Similarity	NPC35288
0.8279	Intermediate Similarity	NPC288416
0.8279	Intermediate Similarity	NPC175333
0.8279	Intermediate Similarity	NPC45224
0.824	Intermediate Similarity	NPC473285
0.8226	Intermediate Similarity	NPC319995
0.8226	Intermediate Similarity	NPC289415
0.8211	Intermediate Similarity	NPC301857
0.8211	Intermediate Similarity	NPC225307
0.8182	Intermediate Similarity	NPC244454
0.8145	Intermediate Similarity	NPC253595
0.8145	Intermediate Similarity	NPC295970
0.8131	Intermediate Similarity	NPC262826
0.812	Intermediate Similarity	NPC216605
0.812	Intermediate Similarity	NPC122245
0.812	Intermediate Similarity	NPC266389
0.8099	Intermediate Similarity	NPC473881
0.8091	Intermediate Similarity	NPC47286
0.808	Intermediate Similarity	NPC17567
0.8049	Intermediate Similarity	NPC61181
0.8049	Intermediate Similarity	NPC471026
0.8047	Intermediate Similarity	NPC263829
0.8031	Intermediate Similarity	NPC322503
0.8031	Intermediate Similarity	NPC470143
0.8016	Intermediate Similarity	NPC478255
0.8016	Intermediate Similarity	NPC254819
0.8016	Intermediate Similarity	NPC281798
0.8	Intermediate Similarity	NPC477293
0.8	Intermediate Similarity	NPC229784
0.8	Intermediate Similarity	NPC477294
0.7984	Intermediate Similarity	NPC103533
0.7946	Intermediate Similarity	NPC475203
0.7946	Intermediate Similarity	NPC136962
0.7946	Intermediate Similarity	NPC472315
0.7946	Intermediate Similarity	NPC474376
0.7946	Intermediate Similarity	NPC472316
0.7928	Intermediate Similarity	NPC148060
0.7923	Intermediate Similarity	NPC476376
0.792	Intermediate Similarity	NPC146540
0.792	Intermediate Similarity	NPC232880
0.7913	Intermediate Similarity	NPC234376
0.7891	Intermediate Similarity	NPC28637
0.7891	Intermediate Similarity	NPC254398
0.7874	Intermediate Similarity	NPC219677
0.7863	Intermediate Similarity	NPC81515
0.7863	Intermediate Similarity	NPC68092
0.7863	Intermediate Similarity	NPC64141
0.7863	Intermediate Similarity	NPC197316
0.7863	Intermediate Similarity	NPC472350
0.7863	Intermediate Similarity	NPC476383
0.7863	Intermediate Similarity	NPC89105
0.7857	Intermediate Similarity	NPC11025
0.7846	Intermediate Similarity	NPC472132
0.7845	Intermediate Similarity	NPC265002
0.784	Intermediate Similarity	NPC230331
0.784	Intermediate Similarity	NPC476873
0.7829	Intermediate Similarity	NPC169398
0.7829	Intermediate Similarity	NPC34293
0.7829	Intermediate Similarity	NPC287597
0.7829	Intermediate Similarity	NPC886
0.7829	Intermediate Similarity	NPC471883
0.7812	Intermediate Similarity	NPC473924
0.7805	Intermediate Similarity	NPC470815
0.7788	Intermediate Similarity	NPC37115
0.7787	Intermediate Similarity	NPC475328
0.7786	Intermediate Similarity	NPC260425
0.7786	Intermediate Similarity	NPC101686
0.7786	Intermediate Similarity	NPC469364
0.7786	Intermediate Similarity	NPC78363
0.7786	Intermediate Similarity	NPC65262
0.7778	Intermediate Similarity	NPC120217
0.7769	Intermediate Similarity	NPC185778
0.7769	Intermediate Similarity	NPC476870
0.7768	Intermediate Similarity	NPC280616
0.7768	Intermediate Similarity	NPC171831
0.7768	Intermediate Similarity	NPC242913
0.7759	Intermediate Similarity	NPC185840
0.7744	Intermediate Similarity	NPC475513
0.7744	Intermediate Similarity	NPC473755
0.7744	Intermediate Similarity	NPC476377
0.7744	Intermediate Similarity	NPC134405
0.7744	Intermediate Similarity	NPC47471
0.7744	Intermediate Similarity	NPC476385
0.7736	Intermediate Similarity	NPC472319
0.7727	Intermediate Similarity	NPC31745
0.7727	Intermediate Similarity	NPC220936
0.7727	Intermediate Similarity	NPC205195
0.7727	Intermediate Similarity	NPC49597
0.7724	Intermediate Similarity	NPC476142
0.7717	Intermediate Similarity	NPC27712
0.7712	Intermediate Similarity	NPC313193
0.771	Intermediate Similarity	NPC37468
0.771	Intermediate Similarity	NPC471345
0.771	Intermediate Similarity	NPC157554
0.771	Intermediate Similarity	NPC166180
0.7687	Intermediate Similarity	NPC265648
0.7687	Intermediate Similarity	NPC222433
0.7687	Intermediate Similarity	NPC284957
0.7669	Intermediate Similarity	NPC202700
0.7669	Intermediate Similarity	NPC473799
0.7669	Intermediate Similarity	NPC475530
0.7661	Intermediate Similarity	NPC138798
0.7642	Intermediate Similarity	NPC55608
0.763	Intermediate Similarity	NPC112
0.763	Intermediate Similarity	NPC476397
0.763	Intermediate Similarity	NPC175214
0.763	Intermediate Similarity	NPC476381
0.763	Intermediate Similarity	NPC269141
0.763	Intermediate Similarity	NPC247032
0.763	Intermediate Similarity	NPC96795
0.763	Intermediate Similarity	NPC264632
0.763	Intermediate Similarity	NPC476384
0.763	Intermediate Similarity	NPC476378
0.763	Intermediate Similarity	NPC76406
0.763	Intermediate Similarity	NPC476380
0.763	Intermediate Similarity	NPC298257
0.763	Intermediate Similarity	NPC205864
0.763	Intermediate Similarity	NPC476375
0.763	Intermediate Similarity	NPC119537
0.763	Intermediate Similarity	NPC111466
0.763	Intermediate Similarity	NPC293154
0.7619	Intermediate Similarity	NPC476971
0.7619	Intermediate Similarity	NPC476972
0.7615	Intermediate Similarity	NPC136608
0.7615	Intermediate Similarity	NPC30361
0.7615	Intermediate Similarity	NPC38420
0.7615	Intermediate Similarity	NPC114116
0.7612	Intermediate Similarity	NPC80098
0.76	Intermediate Similarity	NPC471758
0.7594	Intermediate Similarity	NPC220942
0.7594	Intermediate Similarity	NPC226005
0.7594	Intermediate Similarity	NPC328273
0.7594	Intermediate Similarity	NPC171134
0.7594	Intermediate Similarity	NPC321184
0.7594	Intermediate Similarity	NPC100389
0.7594	Intermediate Similarity	NPC321638
0.7583	Intermediate Similarity	NPC175771
0.7583	Intermediate Similarity	NPC470820
0.7583	Intermediate Similarity	NPC148055
0.7581	Intermediate Similarity	NPC12016
0.7576	Intermediate Similarity	NPC103409
0.7576	Intermediate Similarity	NPC470572

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 NPC470825 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	680
0.2-0.3	1386
0.3-0.4	3348
0.4-0.5	2498
0.5-0.6	974
0.6-0.7	77
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7863	Intermediate Similarity	NPD7266	Discontinued
0.7759	Intermediate Similarity	NPD969	Suspended
0.7674	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5125	Phase 3
0.748	Intermediate Similarity	NPD5126	Approved
0.7383	Intermediate Similarity	NPD689	Discontinued
0.7241	Intermediate Similarity	NPD5048	Discontinued
0.7222	Intermediate Similarity	NPD1091	Approved
0.7217	Intermediate Similarity	NPD6647	Phase 2
0.7196	Intermediate Similarity	NPD1282	Approved
0.7092	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1653	Approved
0.6911	Remote Similarity	NPD6010	Discontinued
0.6891	Remote Similarity	NPD6685	Approved
0.688	Remote Similarity	NPD694	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2067	Discontinued
0.68	Remote Similarity	NPD4198	Discontinued
0.6724	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5926	Approved
0.6723	Remote Similarity	NPD5909	Discontinued
0.6694	Remote Similarity	NPD1358	Approved
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7798	Approved
0.6643	Remote Similarity	NPD6190	Approved
0.6639	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5765	Approved
0.662	Remote Similarity	NPD1652	Phase 2
0.6619	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6912	Phase 3
0.66	Remote Similarity	NPD8455	Phase 2
0.6587	Remote Similarity	NPD2629	Approved
0.6567	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6686	Approved
0.6538	Remote Similarity	NPD9716	Approved
0.6528	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3971	Phase 1
0.6504	Remote Similarity	NPD2182	Approved
0.6475	Remote Similarity	NPD3134	Approved
0.6471	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD9495	Approved
0.6415	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7838	Discovery
0.64	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD1238	Approved
0.6385	Remote Similarity	NPD9545	Approved
0.6385	Remote Similarity	NPD7741	Discontinued
0.6383	Remote Similarity	NPD7097	Phase 1
0.6357	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5124	Phase 1
0.6345	Remote Similarity	NPD4628	Phase 3
0.6336	Remote Similarity	NPD7503	Approved
0.6331	Remote Similarity	NPD6233	Phase 2
0.6328	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7685	Pre-registration
0.629	Remote Similarity	NPD290	Approved
0.627	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD5058	Phase 3
0.625	Remote Similarity	NPD2066	Phase 3
0.625	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7799	Discontinued
0.6241	Remote Similarity	NPD4340	Discontinued
0.622	Remote Similarity	NPD8312	Approved
0.622	Remote Similarity	NPD8313	Approved
0.6216	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7054	Approved
0.62	Remote Similarity	NPD5403	Approved
0.6196	Remote Similarity	NPD6559	Discontinued
0.6179	Remote Similarity	NPD164	Approved
0.6174	Remote Similarity	NPD5401	Approved
0.6173	Remote Similarity	NPD7472	Approved
0.6173	Remote Similarity	NPD7074	Phase 3
0.6172	Remote Similarity	NPD7843	Approved
0.6164	Remote Similarity	NPD6674	Discontinued
0.6149	Remote Similarity	NPD7228	Approved
0.6148	Remote Similarity	NPD6637	Approved
0.6143	Remote Similarity	NPD6798	Discontinued
0.6135	Remote Similarity	NPD6797	Phase 2
0.6131	Remote Similarity	NPD2625	Approved
0.6131	Remote Similarity	NPD2628	Approved
0.6131	Remote Similarity	NPD2160	Approved
0.6131	Remote Similarity	NPD2626	Approved
0.6131	Remote Similarity	NPD2159	Approved
0.6131	Remote Similarity	NPD2627	Approved
0.6127	Remote Similarity	NPD1933	Approved
0.6127	Remote Similarity	NPD230	Phase 1
0.6122	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD2575	Approved
0.6121	Remote Similarity	NPD46	Approved
0.6121	Remote Similarity	NPD6698	Approved
0.6121	Remote Similarity	NPD3672	Approved
0.6121	Remote Similarity	NPD3673	Approved
0.6119	Remote Similarity	NPD3496	Discontinued
0.6115	Remote Similarity	NPD2613	Approved
0.6111	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2684	Approved
0.6111	Remote Similarity	NPD7033	Discontinued
0.6107	Remote Similarity	NPD5292	Approved
0.6107	Remote Similarity	NPD5291	Approved
0.6104	Remote Similarity	NPD37	Approved
0.6103	Remote Similarity	NPD7876	Discontinued
0.6099	Remote Similarity	NPD4404	Approved
0.6098	Remote Similarity	NPD7251	Discontinued
0.609	Remote Similarity	NPD4967	Phase 2
0.609	Remote Similarity	NPD1357	Approved
0.609	Remote Similarity	NPD4965	Approved
0.609	Remote Similarity	NPD4966	Approved
0.6084	Remote Similarity	NPD6653	Approved
0.6078	Remote Similarity	NPD4380	Phase 2
0.6074	Remote Similarity	NPD3705	Approved
0.6074	Remote Similarity	NPD422	Phase 1
0.6071	Remote Similarity	NPD3027	Phase 3
0.6065	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7808	Phase 3
0.6061	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3225	Approved
0.6051	Remote Similarity	NPD7075	Discontinued
0.6049	Remote Similarity	NPD3818	Discontinued
0.6048	Remote Similarity	NPD1237	Approved
0.6045	Remote Similarity	NPD5306	Approved
0.6045	Remote Similarity	NPD5723	Approved
0.6045	Remote Similarity	NPD5305	Approved
0.6042	Remote Similarity	NPD4536	Approved
0.6042	Remote Similarity	NPD4538	Approved
0.6042	Remote Similarity	NPD5886	Approved
0.6042	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD41	Approved
0.6036	Remote Similarity	NPD226	Approved
0.6034	Remote Similarity	NPD5346	Phase 2
0.6034	Remote Similarity	NPD5347	Phase 2
0.6032	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD9532	Phase 3
0.6031	Remote Similarity	NPD7157	Approved
0.6028	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD5763	Approved
0.6027	Remote Similarity	NPD5762	Approved
0.6026	Remote Similarity	NPD5402	Approved
0.6015	Remote Similarity	NPD8294	Approved
0.6015	Remote Similarity	NPD8377	Approved
0.6013	Remote Similarity	NPD6234	Discontinued
0.6	Remote Similarity	NPD4106	Approved
0.6	Remote Similarity	NPD4617	Approved
0.6	Remote Similarity	NPD7240	Approved
0.6	Remote Similarity	NPD5203	Approved
0.6	Remote Similarity	NPD4620	Approved
0.6	Remote Similarity	NPD1989	Approved
0.6	Remote Similarity	NPD6801	Discontinued
0.6	Remote Similarity	NPD4135	Approved
0.6	Remote Similarity	NPD5201	Approved
0.6	Remote Similarity	NPD4793	Discontinued
0.6	Remote Similarity	NPD4136	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD6799	Approved
0.6	Remote Similarity	NPD8368	Discontinued
0.6	Remote Similarity	NPD7830	Approved
0.5987	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD2573	Approved
0.5986	Remote Similarity	NPD3614	Approved
0.5986	Remote Similarity	NPD2566	Approved
0.5986	Remote Similarity	NPD3087	Approved
0.5986	Remote Similarity	NPD2570	Approved
0.5986	Remote Similarity	NPD3616	Approved
0.5986	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD3088	Approved
0.5986	Remote Similarity	NPD4746	Phase 3
0.5986	Remote Similarity	NPD3089	Approved
0.5986	Remote Similarity	NPD4062	Phase 3
0.5986	Remote Similarity	NPD3615	Approved
0.5986	Remote Similarity	NPD2424	Discontinued
0.5986	Remote Similarity	NPD4745	Approved
0.5986	Remote Similarity	NPD3090	Approved
0.5986	Remote Similarity	NPD2574	Discontinued
0.5986	Remote Similarity	NPD2571	Approved
0.5985	Remote Similarity	NPD9493	Approved
0.5985	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD7328	Approved
0.5985	Remote Similarity	NPD7327	Approved
0.5983	Remote Similarity	NPD9256	Approved
0.5983	Remote Similarity	NPD9258	Approved
0.5971	Remote Similarity	NPD5647	Approved
0.597	Remote Similarity	NPD8513	Phase 3
0.597	Remote Similarity	NPD8033	Approved
0.597	Remote Similarity	NPD8516	Approved
0.597	Remote Similarity	NPD8380	Approved
0.597	Remote Similarity	NPD8335	Approved
0.597	Remote Similarity	NPD8378	Approved
0.597	Remote Similarity	NPD8379	Approved
0.597	Remote Similarity	NPD8517	Approved
0.597	Remote Similarity	NPD8296	Approved
0.597	Remote Similarity	NPD8515	Approved
0.5968	Remote Similarity	NPD1929	Approved
0.5968	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD1930	Approved
0.5966	Remote Similarity	NPD1202	Approved
0.5966	Remote Similarity	NPD1066	Discontinued
0.5965	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD9294	Approved
0.5957	Remote Similarity	NPD7008	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data