NPASS Compound

Structure

NPC67959 OpenBabel07101719242D 31 35 0 0 0 0 0 0 0 0999 V2000 4.3301 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1723 1.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9979 0.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3403 0.0082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.0860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7678 -0.3285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.0860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3213 -0.9916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.0860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.0860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.0860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4763 -0.2890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.0860 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 -0.8660 3.0860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 9 1 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 5 19 1 0 0 0 0 6 12 1 0 0 0 0 6 20 1 0 0 0 0 7 13 2 0 0 0 0 7 21 1 0 0 0 0 8 14 2 0 0 0 0 8 22 1 0 0 0 0 9 15 2 0 0 0 0 9 29 1 0 0 0 0 10 16 2 0 0 0 0 10 29 1 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 27 2 0 0 0 0 19 31 1 0 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.02
Volume:	379.385
LogP:	1.485
LogD:	0.665
LogS:	-5.388
# Rotatable Bonds:	2
TPSA:	191.03
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.179
Synthetic Accessibility Score:	3.637
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.455
MDCK Permeability:	1.0056925930257421e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.557
20% Bioavailability (F20%):	0.081
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	84.76461029052734%
Volume Distribution (VD):	0.553
Pgp-substrate:	33.35220718383789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.53
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.544
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	3.255
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.393
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.634
Skin Sensitization:	0.901
Carcinogencity:	0.633
Eye Corrosion:	0.003
Eye Irritation:	0.899
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC67959

Natural Product ID:	NPC67959
*Common Name:**	Eschweilenol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LGMNKSBINQXDAI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H10O11/c21-7-1-2-9(15(25)13(7)23)29-10-4-6-12-11-5(19(27)31-18(12)16(10)26)3-8(22)14(24)17(11)30-20(6)28/h1-4,21-26H
SMILES:	Oc1ccc(c(c1O)O)Oc1cc2c(=O)oc3c4c2c(c1O)oc(=O)c4cc(c3O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472022
PubChem CID:	10410181
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	Eukaryota	bark	Suriname rainforest	n.a.	PMID[9677272]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	1000.0	ug ml-1	PMID[478980]

☑ 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 NPC67959 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	619
0.1-0.2	2472
0.2-0.3	5894
0.3-0.4	11315
0.4-0.5	5452
0.5-0.6	4418
0.6-0.7	5554
0.7-0.8	4735
0.8-0.85	1611
0.85-0.9	587
0.9-0.95	37
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC40702
0.9487	High Similarity	NPC267627
0.9487	High Similarity	NPC37502
0.9481	High Similarity	NPC178134
0.9423	High Similarity	NPC247713
0.9193	High Similarity	NPC142614
0.9096	High Similarity	NPC297574
0.9085	High Similarity	NPC181778
0.9062	High Similarity	NPC24164
0.9062	High Similarity	NPC53889
0.9057	High Similarity	NPC289322
0.9057	High Similarity	NPC160512
0.9057	High Similarity	NPC68324
0.9057	High Similarity	NPC114179
0.9057	High Similarity	NPC38779
0.9057	High Similarity	NPC156818
0.9018	High Similarity	NPC272560
0.9	High Similarity	NPC87317
0.8994	High Similarity	NPC104983
0.8994	High Similarity	NPC291948
0.8994	High Similarity	NPC250436
0.8994	High Similarity	NPC318432
0.8994	High Similarity	NPC88803
0.8994	High Similarity	NPC300845
0.8976	High Similarity	NPC166674
0.8976	High Similarity	NPC473550
0.8976	High Similarity	NPC219600
0.8976	High Similarity	NPC46640
0.8976	High Similarity	NPC263119
0.8976	High Similarity	NPC34436
0.8963	High Similarity	NPC473818
0.8944	High Similarity	NPC24627
0.8935	High Similarity	NPC53680
0.8935	High Similarity	NPC125352
0.8935	High Similarity	NPC208797
0.8935	High Similarity	NPC8940
0.8916	High Similarity	NPC289396
0.8916	High Similarity	NPC212038
0.8916	High Similarity	NPC271848
0.8916	High Similarity	NPC81332
0.8916	High Similarity	NPC262580
0.8895	High Similarity	NPC477081
0.8895	High Similarity	NPC477083
0.8882	High Similarity	NPC129533
0.8882	High Similarity	NPC123259
0.8876	High Similarity	NPC80956
0.8855	High Similarity	NPC313304
0.8848	High Similarity	NPC14662
0.8839	High Similarity	NPC262282
0.8839	High Similarity	NPC131766
0.8827	High Similarity	NPC200746
0.8827	High Similarity	NPC139036
0.8817	High Similarity	NPC476619
0.8817	High Similarity	NPC476618
0.8817	High Similarity	NPC476622
0.8817	High Similarity	NPC476620
0.8817	High Similarity	NPC476621
0.8817	High Similarity	NPC476623
0.8812	High Similarity	NPC20541
0.8805	High Similarity	NPC474656
0.8802	High Similarity	NPC158226
0.8797	High Similarity	NPC248102
0.8795	High Similarity	NPC163130
0.8795	High Similarity	NPC280493
0.8795	High Similarity	NPC476279
0.8795	High Similarity	NPC165979
0.879	High Similarity	NPC107636
0.8788	High Similarity	NPC472449
0.8786	High Similarity	NPC290289
0.8786	High Similarity	NPC223534
0.8786	High Similarity	NPC240200
0.8786	High Similarity	NPC158214
0.878	High Similarity	NPC474350
0.878	High Similarity	NPC146134
0.8779	High Similarity	NPC261623
0.8779	High Similarity	NPC469650
0.8779	High Similarity	NPC111490
0.8765	High Similarity	NPC473785
0.8765	High Similarity	NPC36354
0.8758	High Similarity	NPC274730
0.8758	High Similarity	NPC54928
0.875	High Similarity	NPC144801
0.875	High Similarity	NPC98583
0.875	High Similarity	NPC116850
0.875	High Similarity	NPC291510
0.875	High Similarity	NPC197188
0.875	High Similarity	NPC43872
0.875	High Similarity	NPC238672
0.8743	High Similarity	NPC109827
0.8743	High Similarity	NPC124470
0.8742	High Similarity	NPC251110
0.8736	High Similarity	NPC187632
0.8736	High Similarity	NPC472721
0.8736	High Similarity	NPC93065
0.8736	High Similarity	NPC31208
0.8736	High Similarity	NPC472724
0.8736	High Similarity	NPC472720
0.8736	High Similarity	NPC160543
0.8736	High Similarity	NPC469652
0.8735	High Similarity	NPC243877
0.8735	High Similarity	NPC234331
0.8728	High Similarity	NPC469649
0.8728	High Similarity	NPC237202
0.8728	High Similarity	NPC260521
0.8727	High Similarity	NPC8070
0.8721	High Similarity	NPC154527
0.872	High Similarity	NPC25152
0.8712	High Similarity	NPC155101
0.871	High Similarity	NPC134975
0.8706	High Similarity	NPC98546
0.8706	High Similarity	NPC207467
0.8706	High Similarity	NPC297807
0.8706	High Similarity	NPC472387
0.8704	High Similarity	NPC185526
0.8704	High Similarity	NPC167098
0.8704	High Similarity	NPC36077
0.8704	High Similarity	NPC241904
0.8704	High Similarity	NPC296044
0.8704	High Similarity	NPC300727
0.8696	High Similarity	NPC292385
0.8696	High Similarity	NPC125709
0.8693	High Similarity	NPC477082
0.869	High Similarity	NPC65333
0.869	High Similarity	NPC100251
0.869	High Similarity	NPC38438
0.8688	High Similarity	NPC39007
0.8688	High Similarity	NPC161277
0.8686	High Similarity	NPC97924
0.8686	High Similarity	NPC40078
0.8686	High Similarity	NPC471091
0.8683	High Similarity	NPC99613
0.8683	High Similarity	NPC49487
0.8679	High Similarity	NPC61620
0.8678	High Similarity	NPC269046
0.8678	High Similarity	NPC119094
0.8678	High Similarity	NPC173872
0.8675	High Similarity	NPC29160
0.8671	High Similarity	NPC226725
0.8667	High Similarity	NPC248638
0.8667	High Similarity	NPC300984
0.8667	High Similarity	NPC236521
0.8667	High Similarity	NPC121290
0.8667	High Similarity	NPC23298
0.8667	High Similarity	NPC189473
0.8667	High Similarity	NPC152659
0.8659	High Similarity	NPC303565
0.8659	High Similarity	NPC196179
0.8659	High Similarity	NPC124747
0.8659	High Similarity	NPC155754
0.8659	High Similarity	NPC109061
0.8659	High Similarity	NPC34089
0.865	High Similarity	NPC328122
0.865	High Similarity	NPC7543
0.865	High Similarity	NPC238381
0.865	High Similarity	NPC98083
0.865	High Similarity	NPC476242
0.865	High Similarity	NPC474290
0.865	High Similarity	NPC24339
0.865	High Similarity	NPC166456
0.865	High Similarity	NPC100123
0.865	High Similarity	NPC94220
0.8647	High Similarity	NPC472723
0.8647	High Similarity	NPC472992
0.8647	High Similarity	NPC472991
0.8647	High Similarity	NPC79736
0.8647	High Similarity	NPC67629
0.8642	High Similarity	NPC227062
0.8639	High Similarity	NPC163165
0.8634	High Similarity	NPC167091
0.8634	High Similarity	NPC89474
0.8634	High Similarity	NPC292214
0.8634	High Similarity	NPC88645
0.8634	High Similarity	NPC206238
0.8634	High Similarity	NPC271779
0.8631	High Similarity	NPC476365
0.8625	High Similarity	NPC198615
0.8625	High Similarity	NPC78505
0.8625	High Similarity	NPC202157
0.8625	High Similarity	NPC171010
0.8625	High Similarity	NPC228662
0.8623	High Similarity	NPC86477
0.8621	High Similarity	NPC269625
0.8614	High Similarity	NPC259757
0.8614	High Similarity	NPC472450
0.8614	High Similarity	NPC29411
0.8614	High Similarity	NPC275780
0.8614	High Similarity	NPC239752
0.8613	High Similarity	NPC231254
0.8608	High Similarity	NPC139839
0.8608	High Similarity	NPC77378
0.8608	High Similarity	NPC207729
0.8606	High Similarity	NPC90905
0.8606	High Similarity	NPC93739
0.8606	High Similarity	NPC52204
0.8606	High Similarity	NPC476371
0.8606	High Similarity	NPC477841
0.8606	High Similarity	NPC329760
0.8606	High Similarity	NPC42797
0.8606	High Similarity	NPC4013
0.8606	High Similarity	NPC476372

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 NPC67959 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	512
0.1-0.2	1117
0.2-0.3	2216
0.3-0.4	2661
0.4-0.5	1550
0.5-0.6	746
0.6-0.7	215
0.7-0.8	101
0.8-0.85	24
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD1465	Phase 2
0.8994	High Similarity	NPD4868	Clinical (unspecified phase)
0.8909	High Similarity	NPD5844	Phase 1
0.858	High Similarity	NPD7993	Clinical (unspecified phase)
0.8503	High Similarity	NPD6168	Clinical (unspecified phase)
0.8503	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD6167	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6232	Discontinued
0.8405	Intermediate Similarity	NPD2801	Approved
0.8364	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD1934	Approved
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8266	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3750	Approved
0.8198	Intermediate Similarity	NPD7074	Phase 3
0.8187	Intermediate Similarity	NPD1511	Approved
0.814	Intermediate Similarity	NPD7054	Approved
0.8107	Intermediate Similarity	NPD6959	Discontinued
0.8092	Intermediate Similarity	NPD7472	Approved
0.809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD1512	Approved
0.8081	Intermediate Similarity	NPD3818	Discontinued
0.8072	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5494	Approved
0.8024	Intermediate Similarity	NPD3817	Phase 2
0.7976	Intermediate Similarity	NPD3882	Suspended
0.7964	Intermediate Similarity	NPD7819	Suspended
0.7943	Intermediate Similarity	NPD6797	Phase 2
0.7911	Intermediate Similarity	NPD3748	Approved
0.7898	Intermediate Similarity	NPD7251	Discontinued
0.7895	Intermediate Similarity	NPD7199	Phase 2
0.7874	Intermediate Similarity	NPD7228	Approved
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7808	Phase 3
0.7844	Intermediate Similarity	NPD7411	Suspended
0.7824	Intermediate Similarity	NPD7075	Discontinued
0.7824	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD5402	Approved
0.7803	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4380	Phase 2
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7771	Intermediate Similarity	NPD3751	Discontinued
0.7771	Intermediate Similarity	NPD1653	Approved
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3226	Approved
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7768	Phase 2
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1549	Phase 2
0.7647	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6190	Approved
0.7611	Intermediate Similarity	NPD8312	Approved
0.7611	Intermediate Similarity	NPD8313	Approved
0.761	Intermediate Similarity	NPD447	Suspended
0.7609	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6801	Discontinued
0.7588	Intermediate Similarity	NPD37	Approved
0.7558	Intermediate Similarity	NPD4966	Approved
0.7558	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD4965	Approved
0.7547	Intermediate Similarity	NPD1613	Approved
0.7547	Intermediate Similarity	NPD943	Approved
0.7547	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD3764	Approved
0.753	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6799	Approved
0.7528	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7485	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD919	Approved
0.7471	Intermediate Similarity	NPD6599	Discontinued
0.7469	Intermediate Similarity	NPD1510	Phase 2
0.7459	Intermediate Similarity	NPD7549	Discontinued
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7442	Intermediate Similarity	NPD8455	Phase 2
0.7423	Intermediate Similarity	NPD2935	Discontinued
0.7405	Intermediate Similarity	NPD4287	Approved
0.7403	Intermediate Similarity	NPD7240	Approved
0.7403	Intermediate Similarity	NPD7685	Pre-registration
0.7399	Intermediate Similarity	NPD4288	Approved
0.7396	Intermediate Similarity	NPD5403	Approved
0.7386	Intermediate Similarity	NPD1247	Approved
0.7385	Intermediate Similarity	NPD8151	Discontinued
0.7381	Intermediate Similarity	NPD2534	Approved
0.7381	Intermediate Similarity	NPD2533	Approved
0.7381	Intermediate Similarity	NPD2532	Approved
0.7381	Intermediate Similarity	NPD5401	Approved
0.7378	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD9269	Phase 2
0.7349	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.7329	Intermediate Similarity	NPD1240	Approved
0.7321	Intermediate Similarity	NPD7390	Discontinued
0.7317	Intermediate Similarity	NPD1551	Phase 2
0.7312	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD920	Approved
0.7246	Intermediate Similarity	NPD7003	Approved
0.7239	Intermediate Similarity	NPD1607	Approved
0.7235	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7435	Discontinued
0.7215	Intermediate Similarity	NPD1203	Approved
0.7212	Intermediate Similarity	NPD5408	Approved
0.7212	Intermediate Similarity	NPD5406	Approved
0.7212	Intermediate Similarity	NPD5404	Approved
0.7212	Intermediate Similarity	NPD6099	Approved
0.7212	Intermediate Similarity	NPD2796	Approved
0.7212	Intermediate Similarity	NPD5405	Approved
0.7212	Intermediate Similarity	NPD6100	Approved
0.7207	Intermediate Similarity	NPD5242	Approved
0.7204	Intermediate Similarity	NPD8150	Discontinued
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7186	Intermediate Similarity	NPD1243	Approved
0.7186	Intermediate Similarity	NPD2800	Approved
0.7178	Intermediate Similarity	NPD1933	Approved
0.7176	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD3225	Approved
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6778	Approved
0.715	Intermediate Similarity	NPD6776	Approved
0.715	Intermediate Similarity	NPD6782	Approved
0.715	Intermediate Similarity	NPD6777	Approved
0.715	Intermediate Similarity	NPD6779	Approved
0.715	Intermediate Similarity	NPD6781	Approved
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7134	Intermediate Similarity	NPD1608	Approved
0.7128	Intermediate Similarity	NPD7680	Approved
0.7125	Intermediate Similarity	NPD9494	Approved
0.7107	Intermediate Similarity	NPD2797	Approved
0.7099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3268	Approved
0.7099	Intermediate Similarity	NPD2313	Discontinued
0.7098	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9268	Approved
0.7088	Intermediate Similarity	NPD7177	Discontinued
0.7076	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD422	Phase 1
0.7066	Intermediate Similarity	NPD7266	Discontinued
0.7059	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.7048	Intermediate Similarity	NPD2799	Discontinued
0.7041	Intermediate Similarity	NPD7696	Phase 3
0.7041	Intermediate Similarity	NPD7698	Approved
0.7041	Intermediate Similarity	NPD7697	Approved
0.7037	Intermediate Similarity	NPD4625	Phase 3
0.7035	Intermediate Similarity	NPD6273	Approved
0.7021	Intermediate Similarity	NPD8434	Phase 2
0.7011	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD5353	Approved
0.7005	Intermediate Similarity	NPD7871	Phase 2
0.7005	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD7874	Approved
0.7	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2309	Approved
0.6994	Remote Similarity	NPD6798	Discontinued
0.6985	Remote Similarity	NPD7701	Phase 2
0.6973	Remote Similarity	NPD5953	Discontinued
0.6962	Remote Similarity	NPD1610	Phase 2
0.6961	Remote Similarity	NPD5710	Approved
0.6961	Remote Similarity	NPD5711	Approved
0.6957	Remote Similarity	NPD7286	Phase 2
0.6943	Remote Similarity	NPD17	Approved
0.6941	Remote Similarity	NPD8166	Discontinued
0.6941	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7038	Approved
0.6935	Remote Similarity	NPD7039	Approved
0.6932	Remote Similarity	NPD6386	Approved
0.6932	Remote Similarity	NPD6385	Approved
0.6918	Remote Similarity	NPD1481	Phase 2
0.6918	Remote Similarity	NPD9717	Approved
0.6915	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4307	Phase 2
0.6909	Remote Similarity	NPD4060	Phase 1
0.6907	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6823	Phase 2
0.6894	Remote Similarity	NPD3266	Approved
0.6894	Remote Similarity	NPD3267	Approved
0.6891	Remote Similarity	NPD6534	Approved
0.6891	Remote Similarity	NPD6535	Approved
0.689	Remote Similarity	NPD1296	Phase 2
0.6875	Remote Similarity	NPD4379	Clinical (unspecified phase)

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