NPASS Compound

Structure

NPC53587 OpenBabel07101718202D 35 38 0 0 1 0 0 0 0 0999 V2000 -3.4641 -1.0000 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 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 1 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 -2.5000 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 -0.0000 -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 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 -1.7321 -1.0000 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 9 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 13 1 0 0 0 0 4 10 2 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 11 1 0 0 0 0 6 16 2 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 32 1 0 0 0 0 9 24 2 0 0 0 0 9 32 1 0 0 0 0 10 12 1 0 0 0 0 11 25 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 19 2 0 0 0 0 15 33 1 0 0 0 0 16 19 1 0 0 0 0 16 34 1 0 0 0 0 17 8 1 6 0 0 0 17 20 1 0 0 0 0 17 35 1 0 0 0 0 18 28 2 0 0 0 0 18 33 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 22 1 0 0 0 0 21 30 1 6 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 34 1 6 0 0 0 23 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.11
Volume:	453.893
LogP:	0.98
LogD:	0.298
LogS:	-4.176
# Rotatable Bonds:	6
TPSA:	196.35
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	4.02
Fsp3:	0.304
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.318
MDCK Permeability:	2.0992420104448684e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.491
20% Bioavailability (F20%):	0.696
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	85.8460922241211%
Volume Distribution (VD):	0.823
Pgp-substrate:	17.85870933532715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.217
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.417
CYP2D6-inhibitor:	0.544
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.274
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	5.504
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.316
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.59
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.866
Carcinogencity:	0.178
Eye Corrosion:	0.003
Eye Irritation:	0.386
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC53587

Natural Product ID:	NPC53587
*Common Name:**	6''-O-Acetyl-5-O-Beta-D-Galactopyranosyl-7,3',4'-Trihydroxy-4-Phenylcoumarin
IUPAC Name:	[(2R,3R,4S,5R,6S)-6-[4-(3,4-dihydroxyphenyl)-7-hydroxy-2-oxochromen-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Synonyms:
Standard InCHIKey:	YHQLUSZEFHCADG-SUHOFRIBSA-N
Standard InCHI:	InChI=1S/C23H22O12/c1-9(24)32-8-17-20(29)21(30)22(31)23(35-17)34-16-6-11(25)5-15-19(16)12(7-18(28)33-15)10-2-3-13(26)14(27)4-10/h2-7,17,20-23,25-27,29-31H,8H2,1H3/t17-,20+,21+,22-,23-/m1/s1
SMILES:	CC(=O)OC[C@H]1O[C@@H](Oc2cc(O)cc3c2c(cc(=O)o3)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL552043
PubChem CID:	45270513
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]
NPO1684	Hintonia standleyana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19140696]
NPO1684	Hintonia standleyana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	10

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-9.2	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-29.9	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-28.6	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-25.0	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-30.6	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-5.0	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-20.7	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-29.5	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-34.7	%	PMID[503913]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-37.2	%	PMID[503913]

☑ 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 NPC53587 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	402
0.1-0.2	1675
0.2-0.3	3648
0.3-0.4	8772
0.4-0.5	9457
0.5-0.6	4432
0.6-0.7	5069
0.7-0.8	5586
0.8-0.85	2484
0.85-0.9	846
0.9-0.95	320
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC176186
1.0	High Similarity	NPC169404
0.9931	High Similarity	NPC150442
0.9514	High Similarity	NPC226722
0.9459	High Similarity	NPC476352
0.9459	High Similarity	NPC215060
0.9452	High Similarity	NPC476348
0.9452	High Similarity	NPC93924
0.9452	High Similarity	NPC187398
0.9392	High Similarity	NPC213197
0.9388	High Similarity	NPC106138
0.9384	High Similarity	NPC41844
0.9384	High Similarity	NPC476347
0.9324	High Similarity	NPC294522
0.9324	High Similarity	NPC120426
0.9324	High Similarity	NPC21184
0.9324	High Similarity	NPC205727
0.9315	High Similarity	NPC125755
0.9315	High Similarity	NPC199928
0.931	High Similarity	NPC469313
0.931	High Similarity	NPC76176
0.931	High Similarity	NPC138227
0.931	High Similarity	NPC168579
0.931	High Similarity	NPC292443
0.9257	High Similarity	NPC212670
0.9257	High Similarity	NPC176903
0.9257	High Similarity	NPC206264
0.9257	High Similarity	NPC313334
0.9257	High Similarity	NPC30688
0.9252	High Similarity	NPC52740
0.9252	High Similarity	NPC15538
0.9252	High Similarity	NPC473480
0.9247	High Similarity	NPC277867
0.9247	High Similarity	NPC475096
0.9247	High Similarity	NPC161700
0.9241	High Similarity	NPC37793
0.9195	High Similarity	NPC114740
0.9189	High Similarity	NPC478237
0.9189	High Similarity	NPC96294
0.9184	High Similarity	NPC190714
0.9184	High Similarity	NPC268515
0.9184	High Similarity	NPC99515
0.9184	High Similarity	NPC40222
0.9178	High Similarity	NPC232228
0.9172	High Similarity	NPC475084
0.9172	High Similarity	NPC189115
0.9122	High Similarity	NPC15577
0.9122	High Similarity	NPC227902
0.911	High Similarity	NPC478239
0.911	High Similarity	NPC473044
0.9103	High Similarity	NPC469661
0.9103	High Similarity	NPC186406
0.9085	High Similarity	NPC284810
0.9079	High Similarity	NPC8712
0.9073	High Similarity	NPC120774
0.9073	High Similarity	NPC470264
0.9073	High Similarity	NPC264875
0.9073	High Similarity	NPC163598
0.906	High Similarity	NPC280945
0.906	High Similarity	NPC175976
0.9048	High Similarity	NPC25292
0.9048	High Similarity	NPC473045
0.9041	High Similarity	NPC157816
0.9041	High Similarity	NPC469559
0.9041	High Similarity	NPC140502
0.9028	High Similarity	NPC474886
0.9028	High Similarity	NPC124149
0.9007	High Similarity	NPC473621
0.8993	High Similarity	NPC471764
0.8993	High Similarity	NPC87950
0.8986	High Similarity	NPC252292
0.8986	High Similarity	NPC476382
0.8986	High Similarity	NPC85624
0.8986	High Similarity	NPC34587
0.8986	High Similarity	NPC34927
0.8986	High Similarity	NPC100998
0.8981	High Similarity	NPC121290
0.898	High Similarity	NPC252169
0.898	High Similarity	NPC91492
0.898	High Similarity	NPC7439
0.898	High Similarity	NPC256555
0.898	High Similarity	NPC110067
0.898	High Similarity	NPC34245
0.8973	High Similarity	NPC210192
0.8966	High Similarity	NPC98777
0.8966	High Similarity	NPC212770
0.8958	High Similarity	NPC242028
0.8958	High Similarity	NPC203230
0.8947	High Similarity	NPC21902
0.8947	High Similarity	NPC302610
0.894	High Similarity	NPC100818
0.8933	High Similarity	NPC169510
0.8926	High Similarity	NPC74320
0.8926	High Similarity	NPC107120
0.8926	High Similarity	NPC476865
0.8919	High Similarity	NPC476867
0.8912	High Similarity	NPC145319
0.8897	High Similarity	NPC65530
0.8897	High Similarity	NPC59324
0.8897	High Similarity	NPC262328
0.8897	High Similarity	NPC87777
0.8889	High Similarity	NPC78809
0.8874	High Similarity	NPC90896
0.8874	High Similarity	NPC283839
0.8867	High Similarity	NPC232992
0.8867	High Similarity	NPC296377
0.8867	High Similarity	NPC39657
0.8861	High Similarity	NPC19709
0.8859	High Similarity	NPC476869
0.8859	High Similarity	NPC476866
0.8859	High Similarity	NPC476864
0.8859	High Similarity	NPC476868
0.8851	High Similarity	NPC81638
0.8846	High Similarity	NPC478269
0.8836	High Similarity	NPC100389
0.8831	High Similarity	NPC268484
0.8828	High Similarity	NPC166180
0.8828	High Similarity	NPC306441
0.8828	High Similarity	NPC103409
0.8828	High Similarity	NPC16435
0.8824	High Similarity	NPC472611
0.8824	High Similarity	NPC472612
0.8824	High Similarity	NPC289967
0.882	High Similarity	NPC116864
0.882	High Similarity	NPC244776
0.8816	High Similarity	NPC472709
0.8816	High Similarity	NPC472710
0.8812	High Similarity	NPC229729
0.8805	High Similarity	NPC22832
0.8805	High Similarity	NPC311830
0.8797	High Similarity	NPC127782
0.8797	High Similarity	NPC300537
0.8797	High Similarity	NPC77660
0.8797	High Similarity	NPC12326
0.8797	High Similarity	NPC473043
0.8797	High Similarity	NPC189142
0.8792	High Similarity	NPC297342
0.8792	High Similarity	NPC471763
0.879	High Similarity	NPC203020
0.879	High Similarity	NPC239966
0.8784	High Similarity	NPC193722
0.8784	High Similarity	NPC472714
0.8784	High Similarity	NPC278469
0.8784	High Similarity	NPC5262
0.8776	High Similarity	NPC202700
0.8776	High Similarity	NPC106944
0.8767	High Similarity	NPC211549
0.8767	High Similarity	NPC78363
0.8767	High Similarity	NPC470413
0.8767	High Similarity	NPC138738
0.8767	High Similarity	NPC38874
0.8767	High Similarity	NPC134260
0.8767	High Similarity	NPC126206
0.8766	High Similarity	NPC223720
0.8765	High Similarity	NPC211594
0.8765	High Similarity	NPC175107
0.8765	High Similarity	NPC190003
0.8765	High Similarity	NPC254540
0.8765	High Similarity	NPC153755
0.8765	High Similarity	NPC172807
0.8759	High Similarity	NPC61946
0.8759	High Similarity	NPC164787
0.8759	High Similarity	NPC112246
0.8759	High Similarity	NPC470356
0.8759	High Similarity	NPC94750
0.8759	High Similarity	NPC224941
0.8759	High Similarity	NPC476870
0.8759	High Similarity	NPC260898
0.8759	High Similarity	NPC185778
0.8759	High Similarity	NPC238243
0.8759	High Similarity	NPC474206
0.8759	High Similarity	NPC151224
0.8759	High Similarity	NPC121812
0.8759	High Similarity	NPC112939
0.8759	High Similarity	NPC234333
0.8759	High Similarity	NPC311430
0.8759	High Similarity	NPC47398
0.875	High Similarity	NPC286235
0.875	High Similarity	NPC473427
0.875	High Similarity	NPC471062
0.875	High Similarity	NPC475250
0.875	High Similarity	NPC294166
0.875	High Similarity	NPC476386
0.875	High Similarity	NPC306890
0.875	High Similarity	NPC115674
0.875	High Similarity	NPC476398
0.875	High Similarity	NPC210073
0.875	High Similarity	NPC94871
0.875	High Similarity	NPC470933
0.875	High Similarity	NPC115022
0.875	High Similarity	NPC5778
0.875	High Similarity	NPC11060
0.875	High Similarity	NPC236934
0.875	High Similarity	NPC55158
0.875	High Similarity	NPC59516
0.875	High Similarity	NPC259347
0.875	High Similarity	NPC51328
0.8742	High Similarity	NPC284960
0.8742	High Similarity	NPC168822
0.8742	High Similarity	NPC243930

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 NPC53587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	930
0.2-0.3	1852
0.3-0.4	2637
0.4-0.5	1879
0.5-0.6	958
0.6-0.7	343
0.7-0.8	138
0.8-0.85	34
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9257	High Similarity	NPD1653	Approved
0.8707	High Similarity	NPD7266	Discontinued
0.8681	High Similarity	NPD1612	Clinical (unspecified phase)
0.8681	High Similarity	NPD1613	Approved
0.8642	High Similarity	NPD7054	Approved
0.8589	High Similarity	NPD7074	Phase 3
0.8589	High Similarity	NPD7472	Approved
0.8545	High Similarity	NPD4338	Clinical (unspecified phase)
0.8537	High Similarity	NPD6797	Phase 2
0.8485	Intermediate Similarity	NPD7251	Discontinued
0.8481	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD3818	Discontinued
0.8428	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD3027	Phase 3
0.8333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7808	Phase 3
0.8242	Intermediate Similarity	NPD7228	Approved
0.8176	Intermediate Similarity	NPD1934	Approved
0.8148	Intermediate Similarity	NPD6234	Discontinued
0.8125	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5124	Phase 1
0.8121	Intermediate Similarity	NPD6166	Phase 2
0.8105	Intermediate Similarity	NPD1652	Phase 2
0.8084	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD37	Approved
0.8049	Intermediate Similarity	NPD7199	Phase 2
0.8047	Intermediate Similarity	NPD6559	Discontinued
0.8025	Intermediate Similarity	NPD4966	Approved
0.8025	Intermediate Similarity	NPD4965	Approved
0.8025	Intermediate Similarity	NPD4967	Phase 2
0.7988	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD5844	Phase 1
0.7963	Intermediate Similarity	NPD3817	Phase 2
0.7917	Intermediate Similarity	NPD422	Phase 1
0.7917	Intermediate Similarity	NPD1091	Approved
0.7905	Intermediate Similarity	NPD4908	Phase 1
0.7901	Intermediate Similarity	NPD2801	Approved
0.7901	Intermediate Similarity	NPD1465	Phase 2
0.7871	Intermediate Similarity	NPD6674	Discontinued
0.7844	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4380	Phase 2
0.78	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8455	Phase 2
0.7785	Intermediate Similarity	NPD1511	Approved
0.7758	Intermediate Similarity	NPD7075	Discontinued
0.7744	Intermediate Similarity	NPD5402	Approved
0.7733	Intermediate Similarity	NPD7685	Pre-registration
0.7733	Intermediate Similarity	NPD7240	Approved
0.7688	Intermediate Similarity	NPD7549	Discontinued
0.7688	Intermediate Similarity	NPD1512	Approved
0.7673	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1610	Phase 2
0.764	Intermediate Similarity	NPD5403	Approved
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1548	Phase 1
0.7622	Intermediate Similarity	NPD6801	Discontinued
0.7595	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD3882	Suspended
0.7582	Intermediate Similarity	NPD4060	Phase 1
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD5401	Approved
0.7483	Intermediate Similarity	NPD2861	Phase 2
0.7471	Intermediate Similarity	NPD6232	Discontinued
0.747	Intermediate Similarity	NPD7819	Suspended
0.7455	Intermediate Similarity	NPD7411	Suspended
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.7436	Intermediate Similarity	NPD7097	Phase 1
0.7407	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3225	Approved
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7391	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4625	Phase 3
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4628	Phase 3
0.7374	Intermediate Similarity	NPD6843	Phase 3
0.7374	Intermediate Similarity	NPD6842	Approved
0.7374	Intermediate Similarity	NPD6841	Approved
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7368	Intermediate Similarity	NPD3018	Phase 2
0.7358	Intermediate Similarity	NPD1549	Phase 2
0.7353	Intermediate Similarity	NPD5494	Approved
0.7351	Intermediate Similarity	NPD2797	Approved
0.7348	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6799	Approved
0.7341	Intermediate Similarity	NPD7473	Discontinued
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6798	Discontinued
0.7333	Intermediate Similarity	NPD4749	Approved
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7680	Approved
0.7321	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8127	Discontinued
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD4340	Discontinued
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5058	Phase 3
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7585	Approved
0.7256	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3496	Discontinued
0.7246	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7213	Phase 3
0.7239	Intermediate Similarity	NPD7212	Phase 2
0.7235	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2796	Approved
0.7226	Intermediate Similarity	NPD3268	Approved
0.7219	Intermediate Similarity	NPD2983	Phase 2
0.7219	Intermediate Similarity	NPD2982	Phase 2
0.7215	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7583	Approved
0.7209	Intermediate Similarity	NPD6959	Discontinued
0.72	Intermediate Similarity	NPD3705	Approved
0.7197	Intermediate Similarity	NPD1933	Approved
0.7197	Intermediate Similarity	NPD6355	Discontinued
0.7195	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7447	Phase 1
0.7188	Intermediate Similarity	NPD5763	Approved
0.7188	Intermediate Similarity	NPD5762	Approved
0.7186	Intermediate Similarity	NPD6599	Discontinued
0.7184	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6233	Phase 2
0.717	Intermediate Similarity	NPD1510	Phase 2
0.7161	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD2981	Phase 2
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7126	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1551	Phase 2
0.7125	Intermediate Similarity	NPD2935	Discontinued
0.7114	Intermediate Similarity	NPD1357	Approved
0.7111	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4536	Approved
0.7107	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4538	Approved
0.7103	Intermediate Similarity	NPD5535	Approved
0.7099	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD919	Approved
0.7089	Intermediate Similarity	NPD447	Suspended
0.7066	Intermediate Similarity	NPD3687	Approved
0.7066	Intermediate Similarity	NPD3686	Approved
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7048	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.7035	Intermediate Similarity	NPD3749	Approved
0.7034	Intermediate Similarity	NPD228	Approved
0.7031	Intermediate Similarity	NPD7584	Approved
0.7025	Intermediate Similarity	NPD4140	Approved
0.7024	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6032	Approved
0.7019	Intermediate Similarity	NPD6100	Approved
0.7019	Intermediate Similarity	NPD6099	Approved
0.7006	Intermediate Similarity	NPD1296	Phase 2
0.6986	Remote Similarity	NPD7843	Approved
0.6975	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7435	Discontinued
0.6959	Remote Similarity	NPD7157	Approved
0.6959	Remote Similarity	NPD6671	Approved
0.6959	Remote Similarity	NPD2978	Approved
0.6959	Remote Similarity	NPD2977	Approved
0.6957	Remote Similarity	NPD5588	Approved
0.6957	Remote Similarity	NPD4308	Phase 3
0.6957	Remote Similarity	NPD5960	Phase 3
0.6954	Remote Similarity	NPD4626	Approved
0.6951	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8651	Approved
0.6944	Remote Similarity	NPD2684	Approved
0.6939	Remote Similarity	NPD5283	Phase 1
0.6937	Remote Similarity	NPD6653	Approved
0.6928	Remote Similarity	NPD4357	Discontinued
0.6923	Remote Similarity	NPD7458	Discontinued
0.6919	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3620	Phase 2
0.6918	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1558	Phase 1
0.6918	Remote Similarity	NPD1240	Approved
0.6903	Remote Similarity	NPD3266	Approved
0.6903	Remote Similarity	NPD3267	Approved
0.6901	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6779	Approved
0.6895	Remote Similarity	NPD6782	Approved
0.6895	Remote Similarity	NPD6778	Approved
0.6895	Remote Similarity	NPD6780	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