NPASS Compound

Structure

NPC185778 OpenBabel07101718302D 25 26 0 0 1 0 0 0 0 0999 V2000 -6.9282 3.0000 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 -4.3301 -1.5000 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 -2.5981 -1.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 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 -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 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 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 12 1 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 8 1 0 0 0 0 5 10 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 17 1 0 0 0 0 9 18 1 0 0 0 0 10 24 1 0 0 0 0 11 7 1 6 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 19 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 1 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 16 1 0 0 0 0 15 22 1 1 0 0 0 16 24 1 6 0 0 0 16 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.11
Volume:	334.109
LogP:	-0.125
LogD:	0.137
LogS:	-1.522
# Rotatable Bonds:	6
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	3.748
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.777
MDCK Permeability:	6.25475513515994e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.848
Human Intestinal Absorption (HIA):	0.783
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.309
Plasma Protein Binding (PPB):	59.3663444519043%
Volume Distribution (VD):	0.333
Pgp-substrate:	27.084278106689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.213
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.754
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	3.323
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.119
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.519
Carcinogencity:	0.04
Eye Corrosion:	0.005
Eye Irritation:	0.199
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC185778

Natural Product ID:	NPC185778
*Common Name:**	Methyl 3-O-Beta-D-Glucopyranosyl-5-Hydroxycinnamate
IUPAC Name:	methyl (E)-3-[3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate
Synonyms:
Standard InCHIKey:	ZROOQFAPMUQERH-JGWMVUGPSA-N
Standard InCHI:	InChI=1S/C16H20O9/c1-23-12(19)3-2-8-4-9(18)6-10(5-8)24-16-15(22)14(21)13(20)11(7-17)25-16/h2-6,11,13-18,20-22H,7H2,1H3/b3-2+/t11-,13-,14+,15-,16-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(/C=C/C(=O)OC)cc(c2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520439
PubChem CID:	11222008
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO14305	Moricandia arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844940]
NPO14305	Moricandia arvensis	Species	Brassicaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.35	mM	PMID[479130]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	630.8	ug.mL-1	PMID[479130]

☑ 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 NPC185778 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	287
0.1-0.2	1410
0.2-0.3	4131
0.3-0.4	9425
0.4-0.5	8889
0.5-0.6	4955
0.6-0.7	8338
0.7-0.8	4751
0.8-0.85	395
0.85-0.9	99
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC124149
0.9219	High Similarity	NPC12308
0.9185	High Similarity	NPC100389
0.9179	High Similarity	NPC37468
0.9143	High Similarity	NPC478237
0.913	High Similarity	NPC297342
0.9118	High Similarity	NPC210478
0.9098	High Similarity	NPC115022
0.9098	High Similarity	NPC294166
0.9084	High Similarity	NPC218003
0.9078	High Similarity	NPC106138
0.9037	High Similarity	NPC157554
0.9037	High Similarity	NPC186418
0.9023	High Similarity	NPC303422
0.9023	High Similarity	NPC165686
0.9023	High Similarity	NPC85799
0.9023	High Similarity	NPC26080
0.9015	High Similarity	NPC262606
0.9008	High Similarity	NPC146540
0.8986	High Similarity	NPC145319
0.8986	High Similarity	NPC157816
0.8978	High Similarity	NPC202700
0.8963	High Similarity	NPC238243
0.8955	High Similarity	NPC49074
0.8951	High Similarity	NPC213197
0.8947	High Similarity	NPC121376
0.8939	High Similarity	NPC295970
0.8936	High Similarity	NPC41844
0.8921	High Similarity	NPC478239
0.8913	High Similarity	NPC186406
0.8905	High Similarity	NPC226005
0.8897	High Similarity	NPC138350
0.8897	High Similarity	NPC3293
0.8897	High Similarity	NPC103409
0.8897	High Similarity	NPC40664
0.8897	High Similarity	NPC165482
0.8897	High Similarity	NPC166180
0.8897	High Similarity	NPC197723
0.8889	High Similarity	NPC188555
0.8889	High Similarity	NPC130496
0.8881	High Similarity	NPC162093
0.8873	High Similarity	NPC93924
0.8873	High Similarity	NPC96294
0.8865	High Similarity	NPC199928
0.8857	High Similarity	NPC292443
0.8824	High Similarity	NPC55040
0.8815	High Similarity	NPC132895
0.8811	High Similarity	NPC283839
0.8811	High Similarity	NPC206264
0.8811	High Similarity	NPC313334
0.8811	High Similarity	NPC90896
0.8811	High Similarity	NPC212670
0.8806	High Similarity	NPC475067
0.8803	High Similarity	NPC52740
0.8794	High Similarity	NPC226722
0.8794	High Similarity	NPC85624
0.8794	High Similarity	NPC138915
0.8777	High Similarity	NPC215512
0.8777	High Similarity	NPC476442
0.8768	High Similarity	NPC212770
0.8768	High Similarity	NPC98777
0.8759	High Similarity	NPC164857
0.8759	High Similarity	NPC104167
0.8759	High Similarity	NPC169404
0.8759	High Similarity	NPC176186
0.8759	High Similarity	NPC203230
0.8759	High Similarity	NPC53587
0.8759	High Similarity	NPC242028
0.875	High Similarity	NPC251981
0.875	High Similarity	NPC114740
0.875	High Similarity	NPC48863
0.875	High Similarity	NPC13745
0.8741	High Similarity	NPC169510
0.8741	High Similarity	NPC299144
0.8732	High Similarity	NPC476865
0.8723	High Similarity	NPC232228
0.8723	High Similarity	NPC476867
0.8722	High Similarity	NPC40377
0.8714	High Similarity	NPC140502
0.8699	High Similarity	NPC150442
0.8696	High Similarity	NPC65530
0.8696	High Similarity	NPC59324
0.8696	High Similarity	NPC134260
0.8692	High Similarity	NPC52097
0.8686	High Similarity	NPC470236
0.8676	High Similarity	NPC215833
0.8676	High Similarity	NPC69513
0.8671	High Similarity	NPC296377
0.8671	High Similarity	NPC471764
0.8671	High Similarity	NPC87950
0.8662	High Similarity	NPC476864
0.8662	High Similarity	NPC476869
0.8662	High Similarity	NPC476866
0.8662	High Similarity	NPC476868
0.8657	High Similarity	NPC229784
0.8657	High Similarity	NPC477294
0.8657	High Similarity	NPC97326
0.8657	High Similarity	NPC477293
0.8657	High Similarity	NPC248355
0.8652	High Similarity	NPC242756
0.8643	High Similarity	NPC210192
0.8643	High Similarity	NPC257095
0.8643	High Similarity	NPC89686
0.8643	High Similarity	NPC273932
0.8639	High Similarity	NPC260604
0.8639	High Similarity	NPC299435
0.863	High Similarity	NPC472611
0.863	High Similarity	NPC289967
0.863	High Similarity	NPC472612
0.863	High Similarity	NPC215060
0.863	High Similarity	NPC476352
0.8615	High Similarity	NPC11724
0.8613	High Similarity	NPC107478
0.8611	High Similarity	NPC140722
0.8611	High Similarity	NPC4958
0.8611	High Similarity	NPC92054
0.8603	High Similarity	NPC470270
0.8603	High Similarity	NPC473285
0.8592	High Similarity	NPC110063
0.8582	High Similarity	NPC475084
0.8582	High Similarity	NPC302378
0.8582	High Similarity	NPC189115
0.8582	High Similarity	NPC232880
0.8582	High Similarity	NPC469559
0.8571	High Similarity	NPC233559
0.8571	High Similarity	NPC246893
0.8571	High Similarity	NPC471157
0.8571	High Similarity	NPC105827
0.8571	High Similarity	NPC310661
0.8561	High Similarity	NPC195196
0.854	High Similarity	NPC254398
0.8538	High Similarity	NPC476872
0.8533	High Similarity	NPC160780
0.8533	High Similarity	NPC289811
0.8531	High Similarity	NPC34927
0.8531	High Similarity	NPC34587
0.8531	High Similarity	NPC476382
0.8531	High Similarity	NPC216819
0.8531	High Similarity	NPC262182
0.8531	High Similarity	NPC83743
0.8531	High Similarity	NPC100998
0.8531	High Similarity	NPC287615
0.8531	High Similarity	NPC252292
0.8529	High Similarity	NPC166168
0.8529	High Similarity	NPC219677
0.8521	High Similarity	NPC473044
0.8519	High Similarity	NPC166040
0.8519	High Similarity	NPC307110
0.8519	High Similarity	NPC48315
0.8511	High Similarity	NPC469661
0.8507	High Similarity	NPC156692
0.8507	High Similarity	NPC106677
0.8507	High Similarity	NPC173150
0.8507	High Similarity	NPC140750
0.8507	High Similarity	NPC471882
0.8507	High Similarity	NPC45224
0.8507	High Similarity	NPC476873
0.8507	High Similarity	NPC471881
0.8507	High Similarity	NPC35288
0.8503	High Similarity	NPC470264
0.8496	Intermediate Similarity	NPC126991
0.8496	Intermediate Similarity	NPC83218
0.8489	Intermediate Similarity	NPC26954
0.8489	Intermediate Similarity	NPC471719
0.8489	Intermediate Similarity	NPC38099
0.8483	Intermediate Similarity	NPC187398
0.8483	Intermediate Similarity	NPC302989
0.8483	Intermediate Similarity	NPC476348
0.8483	Intermediate Similarity	NPC83975
0.8478	Intermediate Similarity	NPC111635
0.8478	Intermediate Similarity	NPC87696
0.8478	Intermediate Similarity	NPC471883
0.8477	Intermediate Similarity	NPC203020
0.8477	Intermediate Similarity	NPC239966
0.8473	Intermediate Similarity	NPC226712
0.8472	Intermediate Similarity	NPC107120
0.8472	Intermediate Similarity	NPC74320
0.8467	Intermediate Similarity	NPC245120
0.8467	Intermediate Similarity	NPC5423
0.8467	Intermediate Similarity	NPC473924
0.8467	Intermediate Similarity	NPC1913
0.8462	Intermediate Similarity	NPC473045
0.8462	Intermediate Similarity	NPC25292
0.8456	Intermediate Similarity	NPC472024
0.8456	Intermediate Similarity	NPC80600
0.8456	Intermediate Similarity	NPC470079
0.8451	Intermediate Similarity	NPC65833
0.8451	Intermediate Similarity	NPC193722
0.8451	Intermediate Similarity	NPC31081
0.8451	Intermediate Similarity	NPC278469
0.8451	Intermediate Similarity	NPC245219
0.8446	Intermediate Similarity	NPC34965
0.8446	Intermediate Similarity	NPC183536
0.8444	Intermediate Similarity	NPC109275
0.8444	Intermediate Similarity	NPC198487
0.844	Intermediate Similarity	NPC267291
0.8435	Intermediate Similarity	NPC93619
0.8433	Intermediate Similarity	NPC252114
0.8429	Intermediate Similarity	NPC262328
0.8429	Intermediate Similarity	NPC126206

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 NPC185778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	813
0.2-0.3	1837
0.3-0.4	2809
0.4-0.5	1820
0.5-0.6	1085
0.6-0.7	472
0.7-0.8	76
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8811	High Similarity	NPD1653	Approved
0.8473	Intermediate Similarity	NPD1091	Approved
0.8239	Intermediate Similarity	NPD7266	Discontinued
0.7987	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1652	Phase 2
0.7857	Intermediate Similarity	NPD3027	Phase 3
0.784	Intermediate Similarity	NPD6559	Discontinued
0.7817	Intermediate Similarity	NPD1613	Approved
0.7817	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD422	Phase 1
0.7764	Intermediate Similarity	NPD7054	Approved
0.7716	Intermediate Similarity	NPD7472	Approved
0.7716	Intermediate Similarity	NPD7074	Phase 3
0.7702	Intermediate Similarity	NPD3818	Discontinued
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6797	Phase 2
0.7639	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5124	Phase 1
0.7628	Intermediate Similarity	NPD5402	Approved
0.7622	Intermediate Similarity	NPD7251	Discontinued
0.7591	Intermediate Similarity	NPD3496	Discontinued
0.7584	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7808	Phase 3
0.7546	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7075	Discontinued
0.7516	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD7228	Approved
0.7484	Intermediate Similarity	NPD6234	Discontinued
0.7468	Intermediate Similarity	NPD4965	Approved
0.7468	Intermediate Similarity	NPD4967	Phase 2
0.7468	Intermediate Similarity	NPD4966	Approved
0.7467	Intermediate Similarity	NPD4628	Phase 3
0.7466	Intermediate Similarity	NPD6653	Approved
0.7465	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1358	Approved
0.7432	Intermediate Similarity	NPD1551	Phase 2
0.7431	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4749	Approved
0.7413	Intermediate Similarity	NPD4908	Phase 1
0.7397	Intermediate Similarity	NPD230	Phase 1
0.7391	Intermediate Similarity	NPD7199	Phase 2
0.7389	Intermediate Similarity	NPD1934	Approved
0.7386	Intermediate Similarity	NPD5401	Approved
0.7372	Intermediate Similarity	NPD4380	Phase 2
0.7342	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD8455	Phase 2
0.7342	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4060	Phase 1
0.7328	Intermediate Similarity	NPD290	Approved
0.7321	Intermediate Similarity	NPD8312	Approved
0.7321	Intermediate Similarity	NPD8313	Approved
0.732	Intermediate Similarity	NPD6799	Approved
0.7319	Intermediate Similarity	NPD1357	Approved
0.731	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7685	Pre-registration
0.7303	Intermediate Similarity	NPD6190	Approved
0.7296	Intermediate Similarity	NPD3817	Phase 2
0.729	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1610	Phase 2
0.7278	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7266	Intermediate Similarity	NPD1778	Approved
0.7256	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6166	Phase 2
0.7252	Intermediate Similarity	NPD3134	Approved
0.7246	Intermediate Similarity	NPD1548	Phase 1
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4625	Phase 3
0.7233	Intermediate Similarity	NPD7819	Suspended
0.7229	Intermediate Similarity	NPD5844	Phase 1
0.7208	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD7843	Approved
0.7183	Intermediate Similarity	NPD2982	Phase 2
0.7183	Intermediate Similarity	NPD2983	Phase 2
0.7181	Intermediate Similarity	NPD7097	Phase 1
0.7171	Intermediate Similarity	NPD6674	Discontinued
0.7169	Intermediate Similarity	NPD3751	Discontinued
0.7163	Intermediate Similarity	NPD3705	Approved
0.7162	Intermediate Similarity	NPD447	Suspended
0.7162	Intermediate Similarity	NPD4340	Discontinued
0.7153	Intermediate Similarity	NPD7157	Approved
0.7153	Intermediate Similarity	NPD6671	Approved
0.7151	Intermediate Similarity	NPD6843	Phase 3
0.7151	Intermediate Similarity	NPD6842	Approved
0.7151	Intermediate Similarity	NPD6841	Approved
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD5058	Phase 3
0.7133	Intermediate Similarity	NPD3225	Approved
0.7126	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2801	Approved
0.7124	Intermediate Similarity	NPD3750	Approved
0.7113	Intermediate Similarity	NPD2981	Phase 2
0.7111	Intermediate Similarity	NPD969	Suspended
0.7107	Intermediate Similarity	NPD7411	Suspended
0.7105	Intermediate Similarity	NPD2424	Discontinued
0.7105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1549	Phase 2
0.7103	Intermediate Similarity	NPD2861	Phase 2
0.7101	Intermediate Similarity	NPD7240	Approved
0.7071	Intermediate Similarity	NPD5585	Approved
0.7067	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1933	Approved
0.7044	Intermediate Similarity	NPD6599	Discontinued
0.7039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5647	Approved
0.703	Intermediate Similarity	NPD3787	Discontinued
0.702	Intermediate Similarity	NPD7033	Discontinued
0.7019	Intermediate Similarity	NPD1465	Phase 2
0.7007	Intermediate Similarity	NPD7095	Approved
0.7006	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1608	Approved
0.6993	Remote Similarity	NPD9717	Approved
0.6992	Remote Similarity	NPD968	Approved
0.6987	Remote Similarity	NPD1511	Approved
0.6987	Remote Similarity	NPD4357	Discontinued
0.6986	Remote Similarity	NPD3018	Phase 2
0.6974	Remote Similarity	NPD6100	Approved
0.6974	Remote Similarity	NPD6099	Approved
0.6974	Remote Similarity	NPD6032	Approved
0.6974	Remote Similarity	NPD2935	Discontinued
0.6966	Remote Similarity	NPD2797	Approved
0.6966	Remote Similarity	NPD1203	Approved
0.6959	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD1048	Approved
0.6954	Remote Similarity	NPD4536	Approved
0.6954	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4538	Approved
0.6948	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6832	Phase 2
0.6939	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7768	Phase 2
0.6933	Remote Similarity	NPD6355	Discontinued
0.6929	Remote Similarity	NPD5536	Phase 2
0.6928	Remote Similarity	NPD6005	Phase 3
0.6928	Remote Similarity	NPD6004	Phase 3
0.6928	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6002	Phase 3
0.6928	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3686	Approved
0.6918	Remote Similarity	NPD3687	Approved
0.6917	Remote Similarity	NPD9697	Approved
0.6913	Remote Similarity	NPD4062	Phase 3
0.6901	Remote Similarity	NPD4626	Approved
0.6899	Remote Similarity	NPD1512	Approved
0.6894	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9545	Approved
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2231	Phase 2
0.6875	Remote Similarity	NPD2235	Phase 2
0.6871	Remote Similarity	NPD5353	Approved
0.6871	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4140	Approved
0.6863	Remote Similarity	NPD2796	Approved
0.6861	Remote Similarity	NPD228	Approved
0.686	Remote Similarity	NPD7549	Discontinued
0.6849	Remote Similarity	NPD6362	Approved
0.6846	Remote Similarity	NPD3268	Approved
0.6846	Remote Similarity	NPD411	Approved
0.6845	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3536	Discontinued
0.6835	Remote Similarity	NPD2534	Approved
0.6835	Remote Similarity	NPD2532	Approved
0.6835	Remote Similarity	NPD2533	Approved
0.6831	Remote Similarity	NPD5691	Approved
0.6828	Remote Similarity	NPD4359	Approved
0.6826	Remote Similarity	NPD6232	Discontinued
0.6818	Remote Similarity	NPD3656	Approved
0.6818	Remote Similarity	NPD291	Approved
0.6812	Remote Similarity	NPD5535	Approved
0.6797	Remote Similarity	NPD1510	Phase 2
0.6797	Remote Similarity	NPD5588	Approved
0.6797	Remote Similarity	NPD3748	Approved
0.6797	Remote Similarity	NPD5960	Phase 3
0.6795	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6971	Discontinued
0.6783	Remote Similarity	NPD5126	Approved
0.6783	Remote Similarity	NPD5125	Phase 3
0.6783	Remote Similarity	NPD17	Approved
0.6781	Remote Similarity	NPD8651	Approved
0.6774	Remote Similarity	NPD7585	Approved
0.6766	Remote Similarity	NPD8127	Discontinued
0.6766	Remote Similarity	NPD6959	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