NPASS Compound

Structure

NPC150442 OpenBabel07101718312D 34 37 0 0 1 0 0 0 0 0999 V2000 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 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 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 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 2.5981 -1.5000 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 3.4641 -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 0.8660 -2.5000 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 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 5.1962 -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 -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 -1.7321 -1.0000 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 6.0622 -1.5000 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 3.4641 3.0000 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 5.1962 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 24 1 0 0 0 0 10 12 1 0 0 0 0 11 30 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 25 1 0 0 0 0 14 31 1 0 0 0 0 15 19 2 0 0 0 0 15 32 1 0 0 0 0 16 19 1 0 0 0 0 16 33 1 0 0 0 0 17 9 1 6 0 0 0 17 20 1 0 0 0 0 17 34 1 0 0 0 0 18 26 2 0 0 0 0 18 32 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 21 22 1 0 0 0 0 21 28 1 6 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 33 1 6 0 0 0 23 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.13
Volume:	447.739
LogP:	1.11
LogD:	0.9
LogS:	-3.998
# Rotatable Bonds:	6
TPSA:	168.28
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	3.839
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.072
MDCK Permeability:	2.4014503651414998e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.931
Human Intestinal Absorption (HIA):	0.501
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	77.55403137207031%
Volume Distribution (VD):	0.74
Pgp-substrate:	15.765790939331055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.172
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.675
CYP2D6-inhibitor:	0.38
CYP2D6-substrate:	0.725
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	9.302
Half-life (T1/2):	0.686

ADMET: Toxicity

hERG Blockers:	0.375
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.526
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.198
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.053
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC150442

Natural Product ID:	NPC150442
*Common Name:**	5-O-Beta-D-Glucopyranosyl-7,4'-Dimethoxy-3'-Hydroxy-4-Phenylcoumarin
IUPAC Name:	4-(3-hydroxy-4-methoxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
Synonyms:
Standard InCHIKey:	FYSYTMFBANOLPM-LDBVRRDLSA-N
Standard InCHI:	InChI=1S/C23H24O11/c1-30-11-6-15-19(12(8-18(26)32-15)10-3-4-14(31-2)13(25)5-10)16(7-11)33-23-22(29)21(28)20(27)17(9-24)34-23/h3-8,17,20-25,27-29H,9H2,1-2H3/t17-,20-,21+,22-,23-/m1/s1
SMILES:	COc1cc2c(c(cc(=O)o2)c2ccc(c(c2)O)OC)c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465425
PubChem CID:	16091571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0001743] Coumarin 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
NPO7125	Hintonia latiflora	Species	Rubiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17067158]
NPO7125	Hintonia latiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19140696]
NPO7125	Hintonia latiflora	Species	Rubiaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	35.1	%	PMID[483668]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	24.7	%	PMID[483668]

☑ 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 NPC150442 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	406
0.1-0.2	1692
0.2-0.3	3699
0.3-0.4	8978
0.4-0.5	9295
0.5-0.6	4354
0.6-0.7	5060
0.7-0.8	5590
0.8-0.85	2381
0.85-0.9	910
0.9-0.95	326
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC176186
0.9931	High Similarity	NPC53587
0.9931	High Similarity	NPC169404
0.9527	High Similarity	NPC215060
0.9527	High Similarity	NPC476352
0.9521	High Similarity	NPC93924
0.9521	High Similarity	NPC187398
0.9521	High Similarity	NPC476348
0.9459	High Similarity	NPC213197
0.9456	High Similarity	NPC106138
0.9452	High Similarity	NPC476347
0.9452	High Similarity	NPC41844
0.9448	High Similarity	NPC226722
0.9392	High Similarity	NPC21184
0.9392	High Similarity	NPC205727
0.9392	High Similarity	NPC120426
0.9392	High Similarity	NPC294522
0.9384	High Similarity	NPC125755
0.9384	High Similarity	NPC199928
0.9324	High Similarity	NPC30688
0.9324	High Similarity	NPC206264
0.9324	High Similarity	NPC212670
0.9324	High Similarity	NPC176903
0.9324	High Similarity	NPC313334
0.932	High Similarity	NPC52740
0.9315	High Similarity	NPC475096
0.9315	High Similarity	NPC277867
0.9315	High Similarity	NPC161700
0.9262	High Similarity	NPC114740
0.9257	High Similarity	NPC478237
0.9257	High Similarity	NPC96294
0.9252	High Similarity	NPC99515
0.9252	High Similarity	NPC190714
0.9247	High Similarity	NPC168579
0.9247	High Similarity	NPC76176
0.9247	High Similarity	NPC138227
0.9247	High Similarity	NPC292443
0.9247	High Similarity	NPC232228
0.9247	High Similarity	NPC469313
0.9241	High Similarity	NPC475084
0.9241	High Similarity	NPC189115
0.9189	High Similarity	NPC15538
0.9189	High Similarity	NPC15577
0.9189	High Similarity	NPC473480
0.9189	High Similarity	NPC227902
0.9178	High Similarity	NPC37793
0.9178	High Similarity	NPC478239
0.9172	High Similarity	NPC469661
0.915	High Similarity	NPC284810
0.9139	High Similarity	NPC120774
0.9139	High Similarity	NPC264875
0.9139	High Similarity	NPC163598
0.9139	High Similarity	NPC470264
0.9128	High Similarity	NPC175976
0.9122	High Similarity	NPC40222
0.9122	High Similarity	NPC268515
0.9116	High Similarity	NPC25292
0.9116	High Similarity	NPC473045
0.911	High Similarity	NPC157816
0.911	High Similarity	NPC469559
0.911	High Similarity	NPC140502
0.9054	High Similarity	NPC100998
0.9054	High Similarity	NPC476382
0.9054	High Similarity	NPC34587
0.9054	High Similarity	NPC34927
0.9054	High Similarity	NPC252292
0.9048	High Similarity	NPC252169
0.9048	High Similarity	NPC7439
0.9048	High Similarity	NPC110067
0.9048	High Similarity	NPC91492
0.9048	High Similarity	NPC256555
0.9048	High Similarity	NPC473044
0.9048	High Similarity	NPC34245
0.9041	High Similarity	NPC186406
0.9034	High Similarity	NPC98777
0.9034	High Similarity	NPC212770
0.902	High Similarity	NPC8712
0.9013	High Similarity	NPC302610
0.9013	High Similarity	NPC21902
0.9	High Similarity	NPC280945
0.8993	High Similarity	NPC476865
0.8966	High Similarity	NPC59324
0.8966	High Similarity	NPC65530
0.8966	High Similarity	NPC474886
0.8966	High Similarity	NPC124149
0.8954	High Similarity	NPC78809
0.8947	High Similarity	NPC473621
0.894	High Similarity	NPC283839
0.894	High Similarity	NPC90896
0.8933	High Similarity	NPC232992
0.8933	High Similarity	NPC87950
0.8933	High Similarity	NPC39657
0.8933	High Similarity	NPC471764
0.8926	High Similarity	NPC85624
0.8926	High Similarity	NPC476869
0.8926	High Similarity	NPC476864
0.8926	High Similarity	NPC476868
0.8926	High Similarity	NPC476866
0.8924	High Similarity	NPC121290
0.8919	High Similarity	NPC81638
0.8912	High Similarity	NPC210192
0.891	High Similarity	NPC478269
0.8904	High Similarity	NPC100389
0.8897	High Similarity	NPC242028
0.8897	High Similarity	NPC16435
0.8897	High Similarity	NPC306441
0.8897	High Similarity	NPC203230
0.8889	High Similarity	NPC472612
0.8889	High Similarity	NPC289967
0.8889	High Similarity	NPC472611
0.8882	High Similarity	NPC472709
0.8882	High Similarity	NPC100818
0.8882	High Similarity	NPC472710
0.8875	High Similarity	NPC229729
0.8874	High Similarity	NPC169510
0.8868	High Similarity	NPC22832
0.8868	High Similarity	NPC311830
0.8867	High Similarity	NPC107120
0.8867	High Similarity	NPC74320
0.8859	High Similarity	NPC297342
0.8859	High Similarity	NPC476867
0.8859	High Similarity	NPC471763
0.8854	High Similarity	NPC239966
0.8854	High Similarity	NPC203020
0.8851	High Similarity	NPC193722
0.8851	High Similarity	NPC5262
0.8851	High Similarity	NPC145319
0.8851	High Similarity	NPC472714
0.8851	High Similarity	NPC278469
0.8844	High Similarity	NPC202700
0.8844	High Similarity	NPC106944
0.8836	High Similarity	NPC470413
0.8836	High Similarity	NPC87777
0.8836	High Similarity	NPC211549
0.8836	High Similarity	NPC262328
0.8836	High Similarity	NPC126206
0.8836	High Similarity	NPC138738
0.8828	High Similarity	NPC47398
0.8828	High Similarity	NPC224941
0.8828	High Similarity	NPC94750
0.8828	High Similarity	NPC112246
0.8828	High Similarity	NPC112939
0.8828	High Similarity	NPC474206
0.8828	High Similarity	NPC121812
0.8828	High Similarity	NPC260898
0.8828	High Similarity	NPC470356
0.8828	High Similarity	NPC234333
0.8828	High Similarity	NPC311430
0.8828	High Similarity	NPC61946
0.8827	High Similarity	NPC153755
0.8827	High Similarity	NPC254540
0.8827	High Similarity	NPC172807
0.8827	High Similarity	NPC211594
0.8816	High Similarity	NPC306890
0.8816	High Similarity	NPC475250
0.8816	High Similarity	NPC473427
0.8816	High Similarity	NPC471062
0.8816	High Similarity	NPC51328
0.8816	High Similarity	NPC470933
0.8816	High Similarity	NPC476386
0.8816	High Similarity	NPC55158
0.8816	High Similarity	NPC259347
0.8816	High Similarity	NPC286235
0.8816	High Similarity	NPC94871
0.8816	High Similarity	NPC476398
0.8812	High Similarity	NPC59516
0.8812	High Similarity	NPC5778
0.8812	High Similarity	NPC236934
0.8808	High Similarity	NPC296377
0.8805	High Similarity	NPC191306
0.8805	High Similarity	NPC19709
0.8805	High Similarity	NPC88023
0.8805	High Similarity	NPC284960
0.8805	High Similarity	NPC222936
0.8805	High Similarity	NPC270335
0.8805	High Similarity	NPC243930
0.8805	High Similarity	NPC309025
0.8797	High Similarity	NPC478267
0.879	High Similarity	NPC173726
0.879	High Similarity	NPC160780
0.879	High Similarity	NPC289811
0.879	High Similarity	NPC241600
0.8784	High Similarity	NPC224876
0.8784	High Similarity	NPC83375
0.8782	High Similarity	NPC11411
0.8782	High Similarity	NPC228357
0.8776	High Similarity	NPC292487
0.8774	High Similarity	NPC268484
0.8773	High Similarity	NPC4390
0.8773	High Similarity	NPC472993
0.8773	High Similarity	NPC163165
0.8767	High Similarity	NPC199459
0.8767	High Similarity	NPC269091
0.8767	High Similarity	NPC177035
0.8767	High Similarity	NPC157554
0.8767	High Similarity	NPC166180
0.8767	High Similarity	NPC471664
0.8767	High Similarity	NPC474639
0.8767	High Similarity	NPC302701
0.8767	High Similarity	NPC227503

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 NPC150442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	935
0.2-0.3	1883
0.3-0.4	2638
0.4-0.5	1856
0.5-0.6	942
0.6-0.7	350
0.7-0.8	131
0.8-0.85	34
0.85-0.9	11
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9324	High Similarity	NPD1653	Approved
0.8704	High Similarity	NPD7054	Approved
0.865	High Similarity	NPD7472	Approved
0.865	High Similarity	NPD7074	Phase 3
0.8649	High Similarity	NPD7266	Discontinued
0.8621	High Similarity	NPD1612	Clinical (unspecified phase)
0.8621	High Similarity	NPD1613	Approved
0.8606	High Similarity	NPD4338	Clinical (unspecified phase)
0.8528	High Similarity	NPD3818	Discontinued
0.8485	Intermediate Similarity	NPD6797	Phase 2
0.8434	Intermediate Similarity	NPD7251	Discontinued
0.8428	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD3027	Phase 3
0.8383	Intermediate Similarity	NPD7808	Phase 3
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7228	Approved
0.8276	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1934	Approved
0.821	Intermediate Similarity	NPD6234	Discontinued
0.8182	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD37	Approved
0.811	Intermediate Similarity	NPD7199	Phase 2
0.8086	Intermediate Similarity	NPD4966	Approved
0.8086	Intermediate Similarity	NPD4965	Approved
0.8086	Intermediate Similarity	NPD4967	Phase 2
0.8075	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD5124	Phase 1
0.8067	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1652	Phase 2
0.8036	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD6559	Discontinued
0.7963	Intermediate Similarity	NPD2801	Approved
0.7963	Intermediate Similarity	NPD1465	Phase 2
0.7941	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6674	Discontinued
0.7904	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1091	Approved
0.7862	Intermediate Similarity	NPD422	Phase 1
0.7852	Intermediate Similarity	NPD4908	Phase 1
0.7791	Intermediate Similarity	NPD7240	Approved
0.7791	Intermediate Similarity	NPD7685	Pre-registration
0.7778	Intermediate Similarity	NPD4380	Phase 2
0.7748	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7549	Discontinued
0.7744	Intermediate Similarity	NPD8455	Phase 2
0.7736	Intermediate Similarity	NPD1511	Approved
0.7736	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7075	Discontinued
0.7702	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5402	Approved
0.7651	Intermediate Similarity	NPD3882	Suspended
0.764	Intermediate Similarity	NPD1512	Approved
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5403	Approved
0.7586	Intermediate Similarity	NPD1548	Phase 1
0.7576	Intermediate Similarity	NPD6801	Discontinued
0.7547	Intermediate Similarity	NPD3750	Approved
0.7532	Intermediate Similarity	NPD4060	Phase 1
0.753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6232	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.7469	Intermediate Similarity	NPD5401	Approved
0.7446	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3018	Phase 2
0.7434	Intermediate Similarity	NPD2861	Phase 2
0.743	Intermediate Similarity	NPD6843	Phase 3
0.743	Intermediate Similarity	NPD6842	Approved
0.743	Intermediate Similarity	NPD6841	Approved
0.7425	Intermediate Similarity	NPD7819	Suspended
0.7412	Intermediate Similarity	NPD5494	Approved
0.741	Intermediate Similarity	NPD7411	Suspended
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.74	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7473	Discontinued
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7097	Phase 1
0.738	Intermediate Similarity	NPD7680	Approved
0.7368	Intermediate Similarity	NPD8127	Discontinued
0.7362	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD3225	Approved
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7326	Intermediate Similarity	NPD3787	Discontinued
0.7317	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1549	Phase 2
0.7308	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2797	Approved
0.7301	Intermediate Similarity	NPD6799	Approved
0.7294	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6798	Discontinued
0.729	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2983	Phase 2
0.7285	Intermediate Similarity	NPD2982	Phase 2
0.7285	Intermediate Similarity	NPD4749	Approved
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3705	Approved
0.7267	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4340	Discontinued
0.7261	Intermediate Similarity	NPD230	Phase 1
0.7261	Intermediate Similarity	NPD1933	Approved
0.7256	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5058	Phase 3
0.7235	Intermediate Similarity	NPD7768	Phase 2
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7233	Intermediate Similarity	NPD3748	Approved
0.7225	Intermediate Similarity	NPD7585	Approved
0.7222	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2981	Phase 2
0.7202	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3496	Discontinued
0.7195	Intermediate Similarity	NPD7213	Phase 3
0.7195	Intermediate Similarity	NPD7212	Phase 2
0.7188	Intermediate Similarity	NPD2796	Approved
0.7181	Intermediate Similarity	NPD1357	Approved
0.7179	Intermediate Similarity	NPD3268	Approved
0.7173	Intermediate Similarity	NPD7583	Approved
0.717	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6959	Discontinued
0.7167	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD7447	Phase 1
0.7151	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD3686	Approved
0.7126	Intermediate Similarity	NPD3687	Approved
0.7125	Intermediate Similarity	NPD1510	Phase 2
0.7115	Intermediate Similarity	NPD7095	Approved
0.7103	Intermediate Similarity	NPD228	Approved
0.7099	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2424	Discontinued
0.7083	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2935	Discontinued
0.7081	Intermediate Similarity	NPD1551	Phase 2
0.7063	Intermediate Similarity	NPD4538	Approved
0.7063	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4536	Approved
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5535	Approved
0.7051	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7783	Phase 2
0.7026	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2978	Approved
0.7018	Intermediate Similarity	NPD2977	Approved
0.7012	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4110	Phase 3
0.701	Intermediate Similarity	NPD8151	Discontinued
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7006	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7584	Approved
0.6994	Remote Similarity	NPD3749	Approved
0.6988	Remote Similarity	NPD4357	Discontinued
0.6982	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4140	Approved
0.6981	Remote Similarity	NPD3620	Phase 2
0.6981	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1558	Phase 1
0.6977	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6032	Approved
0.6975	Remote Similarity	NPD6099	Approved
0.6975	Remote Similarity	NPD6100	Approved
0.6962	Remote Similarity	NPD1296	Phase 2
0.6959	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5177	Phase 3
0.6941	Remote Similarity	NPD4675	Approved
0.6941	Remote Similarity	NPD4678	Approved
0.6939	Remote Similarity	NPD7843	Approved
0.6933	Remote Similarity	NPD3540	Phase 1
0.6933	Remote Similarity	NPD5536	Phase 2
0.6933	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7435	Discontinued
0.6914	Remote Similarity	NPD5960	Phase 3
0.6914	Remote Similarity	NPD4308	Phase 3
0.6914	Remote Similarity	NPD5588	Approved
0.6913	Remote Similarity	NPD7157	Approved
0.6913	Remote Similarity	NPD6671	Approved
0.6908	Remote Similarity	NPD4626	Approved
0.6906	Remote Similarity	NPD7039	Approved
0.6906	Remote Similarity	NPD7038	Approved
0.6903	Remote Similarity	NPD8651	Approved
0.6897	Remote Similarity	NPD2684	Approved
0.6894	Remote Similarity	NPD6653	Approved
0.6885	Remote Similarity	NPD8054	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