NPASS Compound

Structure

CID323126 OpenBabel06191716172D 25 28 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -0.5000 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 -2.5981 -0.5000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -0.8660 -1.5000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 14 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 24 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 21 1 1 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 1 0 0 0 19 25 1 0 0 0 0 21 22 1 1 0 0 0 22 12 1 1 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.24
Volume:	373.304
LogP:	5.785
LogD:	4.572
LogS:	-5.328
# Rotatable Bonds:	1
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	4.462
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.802
MDCK Permeability:	1.789095767890103e-05
Pgp-inhibitor:	0.944
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.87

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.286
Plasma Protein Binding (PPB):	96.57775115966797%
Volume Distribution (VD):	2.59
Pgp-substrate:	4.093512058258057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.327
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.459
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.451
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.459
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.74
CYP3A4-substrate:	0.523

ADMET: Excretion

Clearance (CL):	10.825
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.195
Human Hepatotoxicity (H-HT):	0.489
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.762
Maximum Recommended Daily Dose:	0.576
Skin Sensitization:	0.9
Carcinogencity:	0.521
Eye Corrosion:	0.003
Eye Irritation:	0.358
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC323126

Natural Product ID:	NPC323126
*Common Name:**	Strongylin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AHDRBWCUVQGBTR-DNEUNLEDSA-N
Standard InCHI:	InChI=1S/C22H32O3/c1-14-7-10-18-20(2,3)11-6-12-22(18)21(14,4)13-15-17(24-5)9-8-16(23)19(15)25-22/h8-9,14,18,23H,6-7,10-13H2,1-5H3/t14-,18-,21+,22-/m0/s1
SMILES:	CC1CCC2C(CCCC23C1(CC4=C(C=CC(=C4O3)O)OC)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490779
PubChem CID:	9928112
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO30122	Strongylophora hartmani	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1791476]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	13.0	ug.mL-1	PMID[539123]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	6.5	ug.mL-1	PMID[539123]
NPT27	Others	Unspecified		TI	=	9.0	n.a.	PMID[539123]

☑ 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 NPC323126 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	523
0.1-0.2	1689
0.2-0.3	4076
0.3-0.4	9870
0.4-0.5	8983
0.5-0.6	4609
0.6-0.7	9121
0.7-0.8	3387
0.8-0.85	388
0.85-0.9	43
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9357	High Similarity	NPC90645
0.9343	High Similarity	NPC19869
0.9265	High Similarity	NPC327382
0.9236	High Similarity	NPC2745
0.922	High Similarity	NPC472457
0.9172	High Similarity	NPC157783
0.9167	High Similarity	NPC195561
0.9167	High Similarity	NPC158784
0.9103	High Similarity	NPC302915
0.9041	High Similarity	NPC325860
0.9028	High Similarity	NPC212142
0.9021	High Similarity	NPC475896
0.8951	High Similarity	NPC292256
0.8936	High Similarity	NPC35216
0.8929	High Similarity	NPC127218
0.8929	High Similarity	NPC25966
0.8929	High Similarity	NPC319647
0.8929	High Similarity	NPC245207
0.8912	High Similarity	NPC160196
0.8897	High Similarity	NPC473876
0.8881	High Similarity	NPC50250
0.8873	High Similarity	NPC204347
0.8873	High Similarity	NPC2613
0.8873	High Similarity	NPC59841
0.8873	High Similarity	NPC475891
0.8865	High Similarity	NPC198038
0.8865	High Similarity	NPC259519
0.8857	High Similarity	NPC276490
0.8836	High Similarity	NPC476969
0.8832	High Similarity	NPC82503
0.8828	High Similarity	NPC16269
0.8828	High Similarity	NPC21776
0.8803	High Similarity	NPC471389
0.8794	High Similarity	NPC212942
0.8794	High Similarity	NPC29868
0.8794	High Similarity	NPC260741
0.8794	High Similarity	NPC79622
0.8794	High Similarity	NPC70682
0.8792	High Similarity	NPC188578
0.8792	High Similarity	NPC80918
0.8786	High Similarity	NPC270456
0.8786	High Similarity	NPC248727
0.8786	High Similarity	NPC173660
0.8786	High Similarity	NPC265433
0.8786	High Similarity	NPC162659
0.8777	High Similarity	NPC103967
0.8759	High Similarity	NPC112251
0.8759	High Similarity	NPC220935
0.8759	High Similarity	NPC233980
0.875	High Similarity	NPC473108
0.875	High Similarity	NPC469795
0.875	High Similarity	NPC93323
0.875	High Similarity	NPC45257
0.875	High Similarity	NPC63879
0.875	High Similarity	NPC473845
0.875	High Similarity	NPC280092
0.875	High Similarity	NPC12641
0.8741	High Similarity	NPC107161
0.8732	High Similarity	NPC234568
0.8723	High Similarity	NPC474282
0.8723	High Similarity	NPC107551
0.8723	High Similarity	NPC326797
0.8723	High Similarity	NPC102904
0.8723	High Similarity	NPC176051
0.8723	High Similarity	NPC103976
0.8714	High Similarity	NPC281521
0.8714	High Similarity	NPC313081
0.8714	High Similarity	NPC195022
0.8714	High Similarity	NPC283009
0.8714	High Similarity	NPC261873
0.8714	High Similarity	NPC255147
0.8714	High Similarity	NPC201357
0.8699	High Similarity	NPC101376
0.8699	High Similarity	NPC474397
0.8696	High Similarity	NPC469907
0.8696	High Similarity	NPC45715
0.8696	High Similarity	NPC474356
0.8696	High Similarity	NPC12275
0.8686	High Similarity	NPC222108
0.8686	High Similarity	NPC96719
0.8681	High Similarity	NPC85264
0.8681	High Similarity	NPC47633
0.8681	High Similarity	NPC102044
0.8671	High Similarity	NPC247291
0.8662	High Similarity	NPC292882
0.8662	High Similarity	NPC184613
0.8662	High Similarity	NPC471388
0.8652	High Similarity	NPC230734
0.8652	High Similarity	NPC205442
0.8652	High Similarity	NPC143139
0.8652	High Similarity	NPC474639
0.8652	High Similarity	NPC472800
0.8652	High Similarity	NPC202846
0.8652	High Similarity	NPC227503
0.8643	High Similarity	NPC317380
0.8643	High Similarity	NPC106215
0.8636	High Similarity	NPC140346
0.8633	High Similarity	NPC218884
0.8633	High Similarity	NPC127624
0.8633	High Similarity	NPC202762
0.8633	High Similarity	NPC6451
0.8633	High Similarity	NPC86655
0.863	High Similarity	NPC475872
0.8613	High Similarity	NPC266691
0.8611	High Similarity	NPC175838
0.8603	High Similarity	NPC245060
0.8603	High Similarity	NPC476006
0.8603	High Similarity	NPC112596
0.8601	High Similarity	NPC184797
0.8601	High Similarity	NPC254759
0.8601	High Similarity	NPC73505
0.8601	High Similarity	NPC295719
0.8601	High Similarity	NPC165026
0.8601	High Similarity	NPC309124
0.8601	High Similarity	NPC160283
0.8601	High Similarity	NPC27495
0.8601	High Similarity	NPC34431
0.8593	High Similarity	NPC248557
0.8592	High Similarity	NPC25111
0.8592	High Similarity	NPC6262
0.8592	High Similarity	NPC90615
0.8592	High Similarity	NPC73535
0.8592	High Similarity	NPC211549
0.8592	High Similarity	NPC272157
0.8592	High Similarity	NPC201145
0.8582	High Similarity	NPC474206
0.8582	High Similarity	NPC108198
0.8582	High Similarity	NPC151224
0.8582	High Similarity	NPC470356
0.8582	High Similarity	NPC94750
0.8582	High Similarity	NPC121812
0.8582	High Similarity	NPC112246
0.8582	High Similarity	NPC69029
0.8582	High Similarity	NPC134968
0.8582	High Similarity	NPC294884
0.8582	High Similarity	NPC158142
0.8582	High Similarity	NPC200557
0.8582	High Similarity	NPC241241
0.8582	High Similarity	NPC112939
0.8582	High Similarity	NPC10314
0.8571	High Similarity	NPC269528
0.8571	High Similarity	NPC37196
0.8571	High Similarity	NPC94236
0.8562	High Similarity	NPC469557
0.8561	High Similarity	NPC232275
0.8552	High Similarity	NPC474104
0.8552	High Similarity	NPC477616
0.8552	High Similarity	NPC472451
0.8551	High Similarity	NPC190144
0.8542	High Similarity	NPC178054
0.8542	High Similarity	NPC265075
0.8542	High Similarity	NPC71046
0.854	High Similarity	NPC216836
0.8531	High Similarity	NPC232164
0.8531	High Similarity	NPC473739
0.8531	High Similarity	NPC6300
0.8531	High Similarity	NPC230124
0.8531	High Similarity	NPC32630
0.8531	High Similarity	NPC114171
0.8531	High Similarity	NPC236306
0.8523	High Similarity	NPC477612
0.8521	High Similarity	NPC302701
0.8521	High Similarity	NPC269091
0.8521	High Similarity	NPC476639
0.8521	High Similarity	NPC16435
0.8521	High Similarity	NPC114155
0.8521	High Similarity	NPC30632
0.8521	High Similarity	NPC306441
0.8521	High Similarity	NPC300846
0.8521	High Similarity	NPC126101
0.8521	High Similarity	NPC234952
0.8521	High Similarity	NPC472336
0.8521	High Similarity	NPC472334
0.8514	High Similarity	NPC281549
0.8511	High Similarity	NPC125649
0.8511	High Similarity	NPC209199
0.8511	High Similarity	NPC160697
0.8503	High Similarity	NPC211758
0.8503	High Similarity	NPC260397
0.8503	High Similarity	NPC87794
0.85	High Similarity	NPC14224
0.85	High Similarity	NPC161958
0.85	High Similarity	NPC161203
0.8489	Intermediate Similarity	NPC299221
0.8489	Intermediate Similarity	NPC234488
0.8489	Intermediate Similarity	NPC311680
0.8489	Intermediate Similarity	NPC214860
0.8489	Intermediate Similarity	NPC192687
0.8489	Intermediate Similarity	NPC51840
0.8489	Intermediate Similarity	NPC224157
0.8478	Intermediate Similarity	NPC63179
0.8478	Intermediate Similarity	NPC47288
0.8472	Intermediate Similarity	NPC291101
0.8472	Intermediate Similarity	NPC12668
0.8472	Intermediate Similarity	NPC308768
0.8472	Intermediate Similarity	NPC266197
0.8472	Intermediate Similarity	NPC20520
0.8472	Intermediate Similarity	NPC61783
0.8472	Intermediate Similarity	NPC22317
0.8462	Intermediate Similarity	NPC56329

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 NPC323126 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	894
0.2-0.3	1893
0.3-0.4	2928
0.4-0.5	1556
0.5-0.6	945
0.6-0.7	445
0.7-0.8	62
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8489	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD4625	Phase 3
0.8273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD4749	Approved
0.8239	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1613	Approved
0.8099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD4908	Phase 1
0.8082	Intermediate Similarity	NPD6100	Approved
0.8082	Intermediate Similarity	NPD6099	Approved
0.8058	Intermediate Similarity	NPD6696	Suspended
0.8028	Intermediate Similarity	NPD3027	Phase 3
0.7943	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6671	Approved
0.7842	Intermediate Similarity	NPD1610	Phase 2
0.78	Intermediate Similarity	NPD6674	Discontinued
0.7762	Intermediate Similarity	NPD2861	Phase 2
0.7748	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3620	Phase 2
0.774	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD7340	Approved
0.761	Intermediate Similarity	NPD2801	Approved
0.759	Intermediate Similarity	NPD5844	Phase 1
0.7547	Intermediate Similarity	NPD1934	Approved
0.7531	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD7228	Approved
0.7516	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD7906	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4577	Approved
0.7471	Intermediate Similarity	NPD4578	Approved
0.745	Intermediate Similarity	NPD5735	Approved
0.7445	Intermediate Similarity	NPD1398	Phase 1
0.7442	Intermediate Similarity	NPD4663	Approved
0.7429	Intermediate Similarity	NPD1548	Phase 1
0.741	Intermediate Similarity	NPD6166	Phase 2
0.741	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7311	Approved
0.7368	Intermediate Similarity	NPD7310	Approved
0.7368	Intermediate Similarity	NPD7312	Approved
0.7368	Intermediate Similarity	NPD7313	Approved
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD37	Approved
0.7326	Intermediate Similarity	NPD7309	Approved
0.7325	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7549	Discontinued
0.731	Intermediate Similarity	NPD8651	Approved
0.7305	Intermediate Similarity	NPD2489	Approved
0.7305	Intermediate Similarity	NPD27	Approved
0.7301	Intermediate Similarity	NPD4967	Phase 2
0.7301	Intermediate Similarity	NPD4965	Approved
0.7301	Intermediate Similarity	NPD4966	Approved
0.7299	Intermediate Similarity	NPD228	Approved
0.7289	Intermediate Similarity	NPD3051	Approved
0.7284	Intermediate Similarity	NPD1465	Phase 2
0.7279	Intermediate Similarity	NPD3018	Phase 2
0.7273	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD4060	Phase 1
0.7262	Intermediate Similarity	NPD7473	Discontinued
0.7246	Intermediate Similarity	NPD2969	Approved
0.7246	Intermediate Similarity	NPD2970	Approved
0.7241	Intermediate Similarity	NPD5327	Phase 3
0.7235	Intermediate Similarity	NPD7074	Phase 3
0.7229	Intermediate Similarity	NPD7199	Phase 2
0.7225	Intermediate Similarity	NPD8053	Approved
0.7225	Intermediate Similarity	NPD8054	Approved
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5762	Approved
0.7208	Intermediate Similarity	NPD5763	Approved
0.7194	Intermediate Similarity	NPD5283	Phase 1
0.7186	Intermediate Similarity	NPD6232	Discontinued
0.7184	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7095	Approved
0.7176	Intermediate Similarity	NPD7054	Approved
0.7171	Intermediate Similarity	NPD6353	Approved
0.7171	Intermediate Similarity	NPD4097	Suspended
0.7153	Intermediate Similarity	NPD4750	Phase 3
0.7152	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7472	Approved
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7123	Intermediate Similarity	NPD2982	Phase 2
0.7123	Intermediate Similarity	NPD2983	Phase 2
0.7107	Intermediate Similarity	NPD7447	Phase 1
0.7105	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1091	Approved
0.7095	Intermediate Similarity	NPD4624	Approved
0.7092	Intermediate Similarity	NPD7157	Approved
0.7091	Intermediate Similarity	NPD3882	Suspended
0.707	Intermediate Similarity	NPD7466	Approved
0.7063	Intermediate Similarity	NPD1512	Approved
0.7063	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2981	Phase 2
0.7052	Intermediate Similarity	NPD7240	Approved
0.7048	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7831	Phase 2
0.7048	Intermediate Similarity	NPD7833	Phase 2
0.7039	Intermediate Similarity	NPD1558	Phase 1
0.7039	Intermediate Similarity	NPD4140	Approved
0.703	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6959	Discontinued
0.702	Intermediate Similarity	NPD7985	Registered
0.7013	Intermediate Similarity	NPD6111	Discontinued
0.7012	Intermediate Similarity	NPD5722	Discontinued
0.7011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5177	Phase 3
0.7	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7635	Approved
0.6993	Remote Similarity	NPD7644	Approved
0.6987	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD422	Phase 1
0.6982	Remote Similarity	NPD3787	Discontinued
0.6981	Remote Similarity	NPD7124	Phase 2
0.6968	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3892	Phase 2
0.6962	Remote Similarity	NPD8166	Discontinued
0.6954	Remote Similarity	NPD7251	Discontinued
0.6939	Remote Similarity	NPD2233	Approved
0.6939	Remote Similarity	NPD2232	Approved
0.6939	Remote Similarity	NPD2230	Approved
0.6937	Remote Similarity	NPD7212	Phase 2
0.6937	Remote Similarity	NPD7213	Phase 3
0.6934	Remote Similarity	NPD968	Approved
0.6928	Remote Similarity	NPD2238	Phase 2
0.6928	Remote Similarity	NPD3817	Phase 2
0.6919	Remote Similarity	NPD3818	Discontinued
0.6918	Remote Similarity	NPD3496	Discontinued
0.6914	Remote Similarity	NPD7808	Phase 3
0.6913	Remote Similarity	NPD3094	Phase 2
0.6908	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3021	Approved
0.6906	Remote Similarity	NPD3022	Approved
0.6903	Remote Similarity	NPD7097	Phase 1
0.6897	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6797	Phase 2
0.6894	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4380	Phase 2
0.6884	Remote Similarity	NPD290	Approved
0.6883	Remote Similarity	NPD3657	Discovery
0.6882	Remote Similarity	NPD6071	Discontinued
0.6879	Remote Similarity	NPD7266	Discontinued
0.6871	Remote Similarity	NPD3092	Approved
0.6871	Remote Similarity	NPD3705	Approved
0.6871	Remote Similarity	NPD1611	Approved
0.6867	Remote Similarity	NPD7819	Suspended
0.6867	Remote Similarity	NPD5929	Approved
0.6865	Remote Similarity	NPD2494	Approved
0.6865	Remote Similarity	NPD2493	Approved
0.6855	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3750	Approved
0.6855	Remote Similarity	NPD4110	Phase 3
0.6852	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1778	Approved
0.6848	Remote Similarity	NPD6072	Discontinued
0.6845	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7075	Discontinued
0.6845	Remote Similarity	NPD4583	Approved
0.6845	Remote Similarity	NPD4582	Approved
0.6836	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2684	Approved
0.6833	Remote Similarity	NPD2490	Approved
0.6833	Remote Similarity	NPD2488	Approved
0.6828	Remote Similarity	NPD7741	Discontinued
0.6826	Remote Similarity	NPD2560	Approved
0.6826	Remote Similarity	NPD2563	Approved
0.6826	Remote Similarity	NPD5402	Approved
0.6821	Remote Similarity	NPD3751	Discontinued
0.6821	Remote Similarity	NPD8251	Approved
0.6821	Remote Similarity	NPD8252	Approved
0.6821	Remote Similarity	NPD8099	Discontinued
0.6815	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2677	Approved
0.6813	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2797	Approved
0.6795	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4536	Approved
0.6795	Remote Similarity	NPD4538	Approved
0.6792	Remote Similarity	NPD1652	Phase 2
0.6791	Remote Similarity	NPD4004	Approved
0.6791	Remote Similarity	NPD4002	Approved
0.679	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4675	Approved
0.6788	Remote Similarity	NPD4678	Approved
0.6786	Remote Similarity	NPD7768	Phase 2
0.6784	Remote Similarity	NPD7229	Phase 3
0.6782	Remote Similarity	NPD8156	Discontinued
0.6778	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3452	Approved
0.6774	Remote Similarity	NPD3450	Approved
0.6772	Remote Similarity	NPD3540	Phase 1
0.6766	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7843	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