NPASS Compound

Structure

NPC470331 OpenBabel07101718202D 30 32 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 6.9128 -4.3005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4026 1.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9128 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -2.5685 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 -0.5000 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 7.4128 -3.4345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9128 -2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.7024 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 -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 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2437 -0.0933 0.0000 C 0 0 1 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 8.4128 -3.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4128 -1.7024 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 5.4516 0.8849 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 4.4347 -1.4945 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 8 2 0 0 0 0 2 9 1 0 0 0 0 3 27 1 0 0 0 0 4 11 1 0 0 0 0 4 12 2 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 28 1 0 0 0 0 9 10 1 0 0 0 0 9 22 2 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 23 1 0 0 0 0 13 29 1 0 0 0 0 14 6 1 1 0 0 0 14 15 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 6 0 0 0 16 17 1 0 0 0 0 16 25 1 1 0 0 0 17 20 1 0 0 0 0 17 26 1 6 0 0 0 18 8 1 6 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 19 27 1 1 0 0 0 20 28 1 1 0 0 0 20 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.15
Volume:	403.527
LogP:	0.716
LogD:	0.399
LogS:	-2.619
# Rotatable Bonds:	7
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	4.563
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.231
MDCK Permeability:	1.3813374607707374e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.807
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277
Plasma Protein Binding (PPB):	55.845947265625%
Volume Distribution (VD):	0.618
Pgp-substrate:	48.7205696105957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	1.699
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.873
AMES Toxicity:	0.852
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.167
Carcinogencity:	0.89
Eye Corrosion:	0.003
Eye Irritation:	0.053
Respiratory Toxicity:	0.094

Download Data

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

Natural Product: NPC470331

Natural Product ID:	NPC470331
*Common Name:**	(2R,3S)-6-Acetyl-2-[1-O-(Beta-D-Glucopyranosyl)-2-Propenyl]-5-Hydroxy-3-Methoxy-2,3,Dihydrobenzofuran
IUPAC Name:	1-[(2R,3S)-5-hydroxy-3-methoxy-2-[3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-en-2-yl]-2,3-dihydro-1-benzofuran-6-yl]ethanone
Synonyms:
Standard InCHIKey:	SCYVAILUHNGMEE-NXZWVFBWSA-N
Standard InCHI:	InChI=1S/C20H26O10/c1-8(7-28-20-17(26)16(25)15(24)14(6-21)30-20)18-19(27-3)11-4-12(23)10(9(2)22)5-13(11)29-18/h4-5,14-21,23-26H,1,6-7H2,2-3H3/t14-,15-,16+,17-,18-,19+,20-/m1/s1
SMILES:	CC(=O)C1=C(C=C2C(C(OC2=C1)C(=C)COC3C(C(C(C(O3)CO)O)O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011645
PubChem CID:	57331845
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:0002207] O-glycosyl compounds

*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
NPO23708	Aster koraiensis	Species	Asteraceae	Eukaryota	aerial parts	Euidang-myun, Gongju city, Chungchengnam-do, Republic of Korea	2007-Aug	PMID[22264115]
NPO23708	Aster koraiensis	Species	Asteraceae	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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	>	50000.0	nM	PMID[490712]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	30000.0	nM	PMID[490712]

☑ 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 NPC470331 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	360
0.1-0.2	1393
0.2-0.3	3252
0.3-0.4	7589
0.4-0.5	10884
0.5-0.6	4429
0.6-0.7	6088
0.7-0.8	7679
0.8-0.85	907
0.85-0.9	107
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.94	High Similarity	NPC183536
0.94	High Similarity	NPC34965
0.9195	High Similarity	NPC83975
0.9032	High Similarity	NPC177742
0.8973	High Similarity	NPC98395
0.8924	High Similarity	NPC278329
0.8924	High Similarity	NPC146837
0.8896	High Similarity	NPC215811
0.8868	High Similarity	NPC127415
0.8839	High Similarity	NPC299761
0.8839	High Similarity	NPC279281
0.8839	High Similarity	NPC299435
0.8839	High Similarity	NPC230439
0.8839	High Similarity	NPC260604
0.8839	High Similarity	NPC92153
0.8831	High Similarity	NPC190217
0.8824	High Similarity	NPC88886
0.8824	High Similarity	NPC104172
0.8816	High Similarity	NPC4958
0.8816	High Similarity	NPC92054
0.8816	High Similarity	NPC140722
0.8812	High Similarity	NPC178281
0.8805	High Similarity	NPC212099
0.8805	High Similarity	NPC101116
0.8805	High Similarity	NPC56735
0.8805	High Similarity	NPC61594
0.8805	High Similarity	NPC216752
0.879	High Similarity	NPC470606
0.8766	High Similarity	NPC477240
0.8766	High Similarity	NPC106025
0.8766	High Similarity	NPC214454
0.8765	High Similarity	NPC246274
0.8758	High Similarity	NPC199335
0.875	High Similarity	NPC147596
0.875	High Similarity	NPC94777
0.8734	High Similarity	NPC231475
0.8734	High Similarity	NPC470607
0.8734	High Similarity	NPC57072
0.8733	High Similarity	NPC242756
0.8727	High Similarity	NPC475233
0.872	High Similarity	NPC98776
0.8718	High Similarity	NPC301233
0.8712	High Similarity	NPC44558
0.8712	High Similarity	NPC105511
0.8712	High Similarity	NPC212748
0.8712	High Similarity	NPC224462
0.871	High Similarity	NPC23253
0.8704	High Similarity	NPC63470
0.8693	High Similarity	NPC23084
0.8671	High Similarity	NPC474401
0.8671	High Similarity	NPC474398
0.8671	High Similarity	NPC476026
0.8671	High Similarity	NPC474441
0.8662	High Similarity	NPC470604
0.8662	High Similarity	NPC99233
0.8662	High Similarity	NPC470605
0.8662	High Similarity	NPC470603
0.8659	High Similarity	NPC271385
0.8659	High Similarity	NPC5029
0.8659	High Similarity	NPC315619
0.8659	High Similarity	NPC48773
0.8659	High Similarity	NPC76128
0.8659	High Similarity	NPC111536
0.8659	High Similarity	NPC30432
0.8659	High Similarity	NPC307518
0.8659	High Similarity	NPC205076
0.865	High Similarity	NPC472383
0.865	High Similarity	NPC183036
0.865	High Similarity	NPC472381
0.865	High Similarity	NPC191653
0.8645	High Similarity	NPC93619
0.8645	High Similarity	NPC473966
0.8645	High Similarity	NPC191154
0.8642	High Similarity	NPC178851
0.8642	High Similarity	NPC99957
0.8642	High Similarity	NPC181616
0.8642	High Similarity	NPC70441
0.8634	High Similarity	NPC17432
0.8625	High Similarity	NPC217950
0.8616	High Similarity	NPC279732
0.8616	High Similarity	NPC73511
0.8614	High Similarity	NPC102053
0.8614	High Similarity	NPC257714
0.8608	High Similarity	NPC265480
0.8608	High Similarity	NPC261866
0.8608	High Similarity	NPC272550
0.8608	High Similarity	NPC17521
0.8608	High Similarity	NPC149368
0.8606	High Similarity	NPC85368
0.8599	High Similarity	NPC78021
0.8599	High Similarity	NPC268950
0.8599	High Similarity	NPC185103
0.8599	High Similarity	NPC108706
0.8599	High Similarity	NPC106625
0.8599	High Similarity	NPC87304
0.8599	High Similarity	NPC211158
0.8598	High Similarity	NPC34287
0.8598	High Similarity	NPC474434
0.8598	High Similarity	NPC21190
0.8598	High Similarity	NPC471416
0.8598	High Similarity	NPC183357
0.8598	High Similarity	NPC22195
0.859	High Similarity	NPC134819
0.859	High Similarity	NPC175617
0.8589	High Similarity	NPC135345
0.8589	High Similarity	NPC93099
0.858	High Similarity	NPC165720
0.8571	High Similarity	NPC127782
0.8571	High Similarity	NPC22324
0.8571	High Similarity	NPC300537
0.8571	High Similarity	NPC218685
0.8562	High Similarity	NPC200708
0.8562	High Similarity	NPC470358
0.8554	High Similarity	NPC199533
0.8554	High Similarity	NPC68381
0.8554	High Similarity	NPC472607
0.8554	High Similarity	NPC470454
0.8553	High Similarity	NPC313163
0.8553	High Similarity	NPC161749
0.8553	High Similarity	NPC43638
0.8553	High Similarity	NPC23817
0.8553	High Similarity	NPC197896
0.8553	High Similarity	NPC6985
0.8553	High Similarity	NPC156457
0.8553	High Similarity	NPC60966
0.8553	High Similarity	NPC258035
0.8545	High Similarity	NPC235575
0.8545	High Similarity	NPC301683
0.8545	High Similarity	NPC472386
0.8545	High Similarity	NPC267254
0.8544	High Similarity	NPC326910
0.8543	High Similarity	NPC164599
0.8537	High Similarity	NPC473202
0.8537	High Similarity	NPC105025
0.8537	High Similarity	NPC58053
0.8537	High Similarity	NPC112755
0.8537	High Similarity	NPC226294
0.8537	High Similarity	NPC201292
0.8537	High Similarity	NPC170675
0.8537	High Similarity	NPC222455
0.8537	High Similarity	NPC259905
0.8537	High Similarity	NPC471457
0.8537	High Similarity	NPC45638
0.8537	High Similarity	NPC210042
0.8537	High Similarity	NPC475942
0.8537	High Similarity	NPC186807
0.8537	High Similarity	NPC93337
0.8537	High Similarity	NPC469931
0.8537	High Similarity	NPC229687
0.8537	High Similarity	NPC95855
0.8535	High Similarity	NPC321363
0.8535	High Similarity	NPC471347
0.8535	High Similarity	NPC259767
0.8535	High Similarity	NPC253904
0.8535	High Similarity	NPC121001
0.8535	High Similarity	NPC259182
0.8535	High Similarity	NPC88484
0.8535	High Similarity	NPC471349
0.8526	High Similarity	NPC213723
0.8519	High Similarity	NPC88043
0.8519	High Similarity	NPC470178
0.8516	High Similarity	NPC191634
0.8512	High Similarity	NPC58538
0.8509	High Similarity	NPC132737
0.8509	High Similarity	NPC303913
0.8509	High Similarity	NPC269117
0.8503	High Similarity	NPC475246
0.8503	High Similarity	NPC46958
0.8503	High Similarity	NPC232818
0.8503	High Similarity	NPC314489
0.8503	High Similarity	NPC198893
0.8494	Intermediate Similarity	NPC236191
0.8494	Intermediate Similarity	NPC199357
0.8494	Intermediate Similarity	NPC239549
0.8494	Intermediate Similarity	NPC203751
0.8494	Intermediate Similarity	NPC51774
0.8491	Intermediate Similarity	NPC127406
0.8491	Intermediate Similarity	NPC154341
0.8491	Intermediate Similarity	NPC206378
0.8491	Intermediate Similarity	NPC45165
0.8491	Intermediate Similarity	NPC170475
0.8485	Intermediate Similarity	NPC298778
0.8485	Intermediate Similarity	NPC199079
0.8485	Intermediate Similarity	NPC210808
0.8485	Intermediate Similarity	NPC72249
0.8476	Intermediate Similarity	NPC45618
0.8476	Intermediate Similarity	NPC229729
0.8476	Intermediate Similarity	NPC146792
0.8476	Intermediate Similarity	NPC48640
0.8476	Intermediate Similarity	NPC45400
0.8476	Intermediate Similarity	NPC58716
0.8476	Intermediate Similarity	NPC149244
0.8476	Intermediate Similarity	NPC42892
0.8476	Intermediate Similarity	NPC116745
0.8466	Intermediate Similarity	NPC280923
0.8466	Intermediate Similarity	NPC294722
0.8466	Intermediate Similarity	NPC475979
0.8462	Intermediate Similarity	NPC205054
0.8457	Intermediate Similarity	NPC473043
0.8457	Intermediate Similarity	NPC469575

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 NPC470331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	853
0.2-0.3	1774
0.3-0.4	2584
0.4-0.5	1989
0.5-0.6	1084
0.6-0.7	398
0.7-0.8	156
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.872	High Similarity	NPD6559	Discontinued
0.8589	High Similarity	NPD3818	Discontinued
0.8553	High Similarity	NPD4381	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD8313	Approved
0.8284	Intermediate Similarity	NPD8312	Approved
0.8263	Intermediate Similarity	NPD7074	Phase 3
0.8225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7054	Approved
0.8199	Intermediate Similarity	NPD5402	Approved
0.8161	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7472	Approved
0.8107	Intermediate Similarity	NPD6797	Phase 2
0.8095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.7963	Intermediate Similarity	NPD1934	Approved
0.795	Intermediate Similarity	NPD4380	Phase 2
0.7949	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3882	Suspended
0.7914	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2801	Approved
0.7879	Intermediate Similarity	NPD7075	Discontinued
0.7845	Intermediate Similarity	NPD6777	Approved
0.7845	Intermediate Similarity	NPD6778	Approved
0.7845	Intermediate Similarity	NPD6781	Approved
0.7845	Intermediate Similarity	NPD6780	Approved
0.7845	Intermediate Similarity	NPD6782	Approved
0.7845	Intermediate Similarity	NPD6779	Approved
0.7845	Intermediate Similarity	NPD6776	Approved
0.7818	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6166	Phase 2
0.7811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2935	Discontinued
0.7784	Intermediate Similarity	NPD5494	Approved
0.7764	Intermediate Similarity	NPD5403	Approved
0.776	Intermediate Similarity	NPD6823	Phase 2
0.775	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2532	Approved
0.775	Intermediate Similarity	NPD2533	Approved
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7717	Intermediate Similarity	NPD7435	Discontinued
0.7716	Intermediate Similarity	NPD1653	Approved
0.7707	Intermediate Similarity	NPD1549	Phase 2
0.7697	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1551	Phase 2
0.7687	Intermediate Similarity	NPD1091	Approved
0.7669	Intermediate Similarity	NPD3226	Approved
0.7662	Intermediate Similarity	NPD447	Suspended
0.7643	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.7643	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5401	Approved
0.7636	Intermediate Similarity	NPD6801	Discontinued
0.7633	Intermediate Similarity	NPD6959	Discontinued
0.7622	Intermediate Similarity	NPD7696	Phase 3
0.7622	Intermediate Similarity	NPD6599	Discontinued
0.7622	Intermediate Similarity	NPD7698	Approved
0.7622	Intermediate Similarity	NPD7697	Approved
0.759	Intermediate Similarity	NPD7819	Suspended
0.7581	Intermediate Similarity	NPD7870	Phase 2
0.7581	Intermediate Similarity	NPD7871	Phase 2
0.7578	Intermediate Similarity	NPD6799	Approved
0.7572	Intermediate Similarity	NPD5844	Phase 1
0.7569	Intermediate Similarity	NPD6534	Approved
0.7569	Intermediate Similarity	NPD6535	Approved
0.7553	Intermediate Similarity	NPD7701	Phase 2
0.7545	Intermediate Similarity	NPD3817	Phase 2
0.7531	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.7514	Intermediate Similarity	NPD7228	Approved
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.7514	Intermediate Similarity	NPD6212	Phase 3
0.7514	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6213	Phase 3
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7874	Approved
0.747	Intermediate Similarity	NPD7411	Suspended
0.7469	Intermediate Similarity	NPD1511	Approved
0.7468	Intermediate Similarity	NPD2796	Approved
0.7468	Intermediate Similarity	NPD411	Approved
0.7468	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.7446	Intermediate Similarity	NPD7699	Phase 2
0.7446	Intermediate Similarity	NPD7700	Phase 2
0.744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2800	Approved
0.7436	Intermediate Similarity	NPD1933	Approved
0.7435	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7801	Approved
0.7435	Intermediate Similarity	NPD7783	Phase 2
0.7425	Intermediate Similarity	NPD6844	Discontinued
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1510	Phase 2
0.74	Intermediate Similarity	NPD9717	Approved
0.7384	Intermediate Similarity	NPD3787	Discontinued
0.7384	Intermediate Similarity	NPD6232	Discontinued
0.7381	Intermediate Similarity	NPD8455	Phase 2
0.7378	Intermediate Similarity	NPD1512	Approved
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1240	Approved
0.7368	Intermediate Similarity	NPD1203	Approved
0.7356	Intermediate Similarity	NPD7473	Discontinued
0.7355	Intermediate Similarity	NPD2313	Discontinued
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8150	Discontinued
0.733	Intermediate Similarity	NPD8151	Discontinued
0.7326	Intermediate Similarity	NPD1247	Approved
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2798	Approved
0.7317	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2344	Approved
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7283	Intermediate Similarity	NPD5711	Approved
0.7283	Intermediate Similarity	NPD5710	Approved
0.7267	Intermediate Similarity	NPD2424	Discontinued
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3749	Approved
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.7229	Intermediate Similarity	NPD920	Approved
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7266	Discontinued
0.72	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7768	Phase 2
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7178	Intermediate Similarity	NPD3750	Approved
0.7176	Intermediate Similarity	NPD1465	Phase 2
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7135	Intermediate Similarity	NPD7584	Approved
0.7134	Intermediate Similarity	NPD2309	Approved
0.712	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD8320	Phase 1
0.7117	Intermediate Similarity	NPD6674	Discontinued
0.7117	Intermediate Similarity	NPD1243	Approved
0.711	Intermediate Similarity	NPD919	Approved
0.7108	Intermediate Similarity	NPD4662	Approved
0.7108	Intermediate Similarity	NPD4661	Approved
0.7108	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD230	Phase 1
0.71	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6004	Phase 3
0.7099	Intermediate Similarity	NPD6005	Phase 3
0.7099	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1019	Discontinued
0.7097	Intermediate Similarity	NPD5647	Approved
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7047	Intermediate Similarity	NPD9493	Approved
0.7045	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1613	Approved
0.7044	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3496	Discontinued
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4749	Approved
0.7011	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8059	Phase 3
0.7	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6995	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6233	Phase 2
0.698	Remote Similarity	NPD6671	Approved
0.6977	Remote Similarity	NPD5760	Phase 2
0.6977	Remote Similarity	NPD5761	Phase 2
0.6974	Remote Similarity	NPD1778	Approved
0.6968	Remote Similarity	NPD6696	Suspended
0.6957	Remote Similarity	NPD6651	Approved
0.6957	Remote Similarity	NPD6653	Approved
0.6941	Remote Similarity	NPD2651	Approved
0.6941	Remote Similarity	NPD2649	Approved
0.6937	Remote Similarity	NPD943	Approved
0.6937	Remote Similarity	NPD4307	Phase 2
0.6928	Remote Similarity	NPD6190	Approved
0.6923	Remote Similarity	NPD1470	Approved
0.6923	Remote Similarity	NPD2797	Approved
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD7985	Registered
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3268	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