NPASS Compound

Structure

NPC470920 OpenBabel07101719122D 26 29 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2084 -1.8750 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 0.0000 -1.0000 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 0.8660 1.5000 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4265 -1.2515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 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 1.7321 1.0000 0.0000 C 0 0 2 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 1.7321 -1.5860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0376 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.5860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2557 -1.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 8 1 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 1 1 1 0 0 0 8 10 1 0 0 0 0 9 2 1 1 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 20 1 6 0 0 0 11 19 1 1 0 0 0 12 18 1 0 0 0 0 12 21 1 1 0 0 0 13 19 1 1 0 0 0 13 26 1 0 0 0 0 14 22 2 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 6 0 0 0 16 17 1 0 0 0 0 16 24 2 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.2
Volume:	367.719
LogP:	1.814
LogD:	1.008
LogS:	-1.704
# Rotatable Bonds:	0
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.551
Synthetic Accessibility Score:	5.279
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.088
MDCK Permeability:	9.410874190507457e-05
Pgp-inhibitor:	0.252
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.739
Plasma Protein Binding (PPB):	43.01106262207031%
Volume Distribution (VD):	0.733
Pgp-substrate:	41.50065612792969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.207
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.651
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	11.774
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.605
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.21
Carcinogencity:	0.116
Eye Corrosion:	0.043
Eye Irritation:	0.017
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC470920

Natural Product ID:	NPC470920
*Common Name:**	Chaparrolide
IUPAC Name:	n.a.
Synonyms:	Chaparrolide
Standard InCHIKey:	KBORUIMKALHADL-DXKQOFSOSA-N
Standard InCHI:	InChI=1S/C20H30O6/c1-8-5-12(21)18(25)20(4)10(8)6-13-19(3)11(7-14(22)26-13)9(2)15(23)16(24)17(19)20/h8-13,15,17-18,21,23,25H,5-7H2,1-4H3/t8-,9-,10+,11+,12+,13-,15+,17+,18-,19-,20+/m1/s1
SMILES:	CC1CC(C(C2(C1CC3C4(C2C(=O)C(C(C4CC(=O)O3)C)O)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2314661
PubChem CID:	441792
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[509913]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[509913]

☑ 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 NPC470920 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	497
0.1-0.2	3251
0.2-0.3	7878
0.3-0.4	14335
0.4-0.5	7148
0.5-0.6	5047
0.6-0.7	3283
0.7-0.8	1193
0.8-0.85	48
0.85-0.9	12
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9176	High Similarity	NPC236459
0.9167	High Similarity	NPC248216
0.8721	High Similarity	NPC120395
0.8706	High Similarity	NPC237938
0.8706	High Similarity	NPC219535
0.8539	High Similarity	NPC185529
0.8539	High Similarity	NPC472146
0.8523	High Similarity	NPC131104
0.8523	High Similarity	NPC3032
0.8523	High Similarity	NPC473319
0.8506	High Similarity	NPC83242
0.8462	Intermediate Similarity	NPC247877
0.8462	Intermediate Similarity	NPC309127
0.8427	Intermediate Similarity	NPC67653
0.8427	Intermediate Similarity	NPC471459
0.8387	Intermediate Similarity	NPC471241
0.8353	Intermediate Similarity	NPC329490
0.8353	Intermediate Similarity	NPC328639
0.8352	Intermediate Similarity	NPC472148
0.8352	Intermediate Similarity	NPC472147
0.8333	Intermediate Similarity	NPC475211
0.8333	Intermediate Similarity	NPC88337
0.828	Intermediate Similarity	NPC163685
0.8276	Intermediate Similarity	NPC473299
0.8214	Intermediate Similarity	NPC478084
0.8202	Intermediate Similarity	NPC239938
0.8191	Intermediate Similarity	NPC472145
0.8182	Intermediate Similarity	NPC477205
0.8182	Intermediate Similarity	NPC477445
0.8172	Intermediate Similarity	NPC62407
0.8172	Intermediate Similarity	NPC287354
0.8172	Intermediate Similarity	NPC82633
0.8161	Intermediate Similarity	NPC269684
0.814	Intermediate Similarity	NPC476071
0.8132	Intermediate Similarity	NPC77756
0.8132	Intermediate Similarity	NPC50443
0.8132	Intermediate Similarity	NPC18536
0.8111	Intermediate Similarity	NPC476435
0.8111	Intermediate Similarity	NPC476379
0.8105	Intermediate Similarity	NPC472144
0.8085	Intermediate Similarity	NPC256227
0.8085	Intermediate Similarity	NPC235109
0.8085	Intermediate Similarity	NPC475785
0.8081	Intermediate Similarity	NPC202524
0.8068	Intermediate Similarity	NPC473336
0.8068	Intermediate Similarity	NPC9060
0.8068	Intermediate Similarity	NPC477434
0.8068	Intermediate Similarity	NPC181871
0.8068	Intermediate Similarity	NPC471044
0.8046	Intermediate Similarity	NPC289486
0.8046	Intermediate Similarity	NPC121121
0.8046	Intermediate Similarity	NPC61107
0.8043	Intermediate Similarity	NPC198054
0.8041	Intermediate Similarity	NPC470172
0.8041	Intermediate Similarity	NPC471254
0.8023	Intermediate Similarity	NPC125366
0.8022	Intermediate Similarity	NPC200580
0.8022	Intermediate Similarity	NPC477443
0.8022	Intermediate Similarity	NPC477440
0.8	Intermediate Similarity	NPC472273
0.8	Intermediate Similarity	NPC26029
0.7979	Intermediate Similarity	NPC305808
0.7978	Intermediate Similarity	NPC62572
0.7978	Intermediate Similarity	NPC474572
0.7978	Intermediate Similarity	NPC131350
0.7978	Intermediate Similarity	NPC473350
0.7959	Intermediate Similarity	NPC473406
0.7959	Intermediate Similarity	NPC471253
0.7957	Intermediate Similarity	NPC474379
0.7957	Intermediate Similarity	NPC476189
0.7955	Intermediate Similarity	NPC227170
0.7955	Intermediate Similarity	NPC15091
0.7935	Intermediate Similarity	NPC477442
0.7935	Intermediate Similarity	NPC477444
0.7935	Intermediate Similarity	NPC477433
0.7935	Intermediate Similarity	NPC470114
0.7921	Intermediate Similarity	NPC27814
0.7907	Intermediate Similarity	NPC320144
0.7907	Intermediate Similarity	NPC80891
0.7907	Intermediate Similarity	NPC201276
0.79	Intermediate Similarity	NPC203974
0.79	Intermediate Similarity	NPC186054
0.7895	Intermediate Similarity	NPC219353
0.7895	Intermediate Similarity	NPC477264
0.7895	Intermediate Similarity	NPC475765
0.7889	Intermediate Similarity	NPC80700
0.7889	Intermediate Similarity	NPC476726
0.7889	Intermediate Similarity	NPC472272
0.7889	Intermediate Similarity	NPC476727
0.7872	Intermediate Similarity	NPC470424
0.7865	Intermediate Similarity	NPC475689
0.7857	Intermediate Similarity	NPC179858
0.7857	Intermediate Similarity	NPC159789
0.7849	Intermediate Similarity	NPC52756
0.7849	Intermediate Similarity	NPC475878
0.7835	Intermediate Similarity	NPC470388
0.7822	Intermediate Similarity	NPC208461
0.7822	Intermediate Similarity	NPC63841
0.7822	Intermediate Similarity	NPC289702
0.7822	Intermediate Similarity	NPC293850
0.7816	Intermediate Similarity	NPC477851
0.78	Intermediate Similarity	NPC181357
0.7791	Intermediate Similarity	NPC31031
0.7791	Intermediate Similarity	NPC224802
0.7791	Intermediate Similarity	NPC243594
0.7791	Intermediate Similarity	NPC80089
0.7791	Intermediate Similarity	NPC34046
0.7791	Intermediate Similarity	NPC171426
0.7791	Intermediate Similarity	NPC324700
0.7791	Intermediate Similarity	NPC185465
0.7791	Intermediate Similarity	NPC472608
0.7778	Intermediate Similarity	NPC277074
0.7778	Intermediate Similarity	NPC225238
0.7778	Intermediate Similarity	NPC209298
0.7778	Intermediate Similarity	NPC275583
0.7778	Intermediate Similarity	NPC107385
0.7766	Intermediate Similarity	NPC161035
0.7765	Intermediate Similarity	NPC471046
0.7765	Intermediate Similarity	NPC474020
0.7755	Intermediate Similarity	NPC252614
0.7745	Intermediate Similarity	NPC228190
0.7745	Intermediate Similarity	NPC236753
0.7738	Intermediate Similarity	NPC317212
0.7738	Intermediate Similarity	NPC55508
0.7732	Intermediate Similarity	NPC253995
0.7732	Intermediate Similarity	NPC474724
0.7727	Intermediate Similarity	NPC475743
0.7727	Intermediate Similarity	NPC48756
0.7727	Intermediate Similarity	NPC280781
0.7723	Intermediate Similarity	NPC471474
0.7723	Intermediate Similarity	NPC144854
0.7723	Intermediate Similarity	NPC3316
0.7717	Intermediate Similarity	NPC90676
0.7708	Intermediate Similarity	NPC29410
0.7708	Intermediate Similarity	NPC104568
0.7708	Intermediate Similarity	NPC193785
0.7708	Intermediate Similarity	NPC200054
0.7708	Intermediate Similarity	NPC476728
0.77	Intermediate Similarity	NPC301787
0.77	Intermediate Similarity	NPC327093
0.7692	Intermediate Similarity	NPC474215
0.7692	Intermediate Similarity	NPC92139
0.7692	Intermediate Similarity	NPC475729
0.7684	Intermediate Similarity	NPC470423
0.7674	Intermediate Similarity	NPC112463
0.767	Intermediate Similarity	NPC100908
0.767	Intermediate Similarity	NPC471093
0.7667	Intermediate Similarity	NPC105895
0.766	Intermediate Similarity	NPC216137
0.7653	Intermediate Similarity	NPC293890
0.7647	Intermediate Similarity	NPC469984
0.7647	Intermediate Similarity	NPC473410
0.7647	Intermediate Similarity	NPC277017
0.7647	Intermediate Similarity	NPC192813
0.7647	Intermediate Similarity	NPC471094
0.7647	Intermediate Similarity	NPC267753
0.7647	Intermediate Similarity	NPC154608
0.764	Intermediate Similarity	NPC30583
0.7634	Intermediate Similarity	NPC24705
0.7634	Intermediate Similarity	NPC61688
0.7634	Intermediate Similarity	NPC56962
0.7629	Intermediate Similarity	NPC470632
0.7629	Intermediate Similarity	NPC74466
0.7629	Intermediate Similarity	NPC470425
0.7624	Intermediate Similarity	NPC222833
0.7624	Intermediate Similarity	NPC56656
0.7619	Intermediate Similarity	NPC49451
0.7619	Intermediate Similarity	NPC81759
0.7619	Intermediate Similarity	NPC97002
0.7614	Intermediate Similarity	NPC134227
0.7614	Intermediate Similarity	NPC261616
0.7614	Intermediate Similarity	NPC470609
0.7609	Intermediate Similarity	NPC263802
0.7604	Intermediate Similarity	NPC470031
0.7604	Intermediate Similarity	NPC470232
0.7604	Intermediate Similarity	NPC98639
0.76	Intermediate Similarity	NPC139347
0.76	Intermediate Similarity	NPC122811
0.76	Intermediate Similarity	NPC34562
0.7596	Intermediate Similarity	NPC201992
0.7596	Intermediate Similarity	NPC171888
0.7596	Intermediate Similarity	NPC29505
0.7596	Intermediate Similarity	NPC146945
0.7579	Intermediate Similarity	NPC224060
0.7579	Intermediate Similarity	NPC244356
0.7576	Intermediate Similarity	NPC259654
0.7576	Intermediate Similarity	NPC298266
0.7573	Intermediate Similarity	NPC227879
0.7573	Intermediate Similarity	NPC208333
0.7573	Intermediate Similarity	NPC141350
0.7573	Intermediate Similarity	NPC310546
0.757	Intermediate Similarity	NPC146432
0.757	Intermediate Similarity	NPC470778
0.7558	Intermediate Similarity	NPC108840
0.7558	Intermediate Similarity	NPC472487
0.7558	Intermediate Similarity	NPC4209
0.7558	Intermediate Similarity	NPC472486
0.7551	Intermediate Similarity	NPC89099
0.7551	Intermediate Similarity	NPC38471
0.7551	Intermediate Similarity	NPC38296

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 NPC470920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	553
0.1-0.2	3484
0.2-0.3	3225
0.3-0.4	1207
0.4-0.5	351
0.5-0.6	224
0.6-0.7	85
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7857	Intermediate Similarity	NPD3703	Phase 2
0.7822	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6118	Approved
0.7791	Intermediate Similarity	NPD6115	Approved
0.7791	Intermediate Similarity	NPD6114	Approved
0.7791	Intermediate Similarity	NPD6697	Approved
0.7558	Intermediate Similarity	NPD6117	Approved
0.7471	Intermediate Similarity	NPD6116	Phase 1
0.7326	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3702	Approved
0.7018	Intermediate Similarity	NPD8328	Phase 3
0.6991	Remote Similarity	NPD6921	Approved
0.6977	Remote Similarity	NPD4789	Approved
0.6939	Remote Similarity	NPD8035	Phase 2
0.6939	Remote Similarity	NPD8034	Phase 2
0.6905	Remote Similarity	NPD4224	Phase 2
0.6897	Remote Similarity	NPD5777	Approved
0.6893	Remote Similarity	NPD1700	Approved
0.686	Remote Similarity	NPD3698	Phase 2
0.6842	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4632	Approved
0.68	Remote Similarity	NPD7748	Approved
0.6782	Remote Similarity	NPD4244	Approved
0.6782	Remote Similarity	NPD4245	Approved
0.6774	Remote Similarity	NPD1780	Approved
0.6774	Remote Similarity	NPD1779	Approved
0.6768	Remote Similarity	NPD7515	Phase 2
0.6765	Remote Similarity	NPD7902	Approved
0.6705	Remote Similarity	NPD6081	Approved
0.6636	Remote Similarity	NPD6402	Approved
0.6636	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD5739	Approved
0.6636	Remote Similarity	NPD6675	Approved
0.6632	Remote Similarity	NPD3669	Approved
0.6632	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3671	Phase 1
0.6609	Remote Similarity	NPD6319	Approved
0.6606	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6372	Approved
0.6606	Remote Similarity	NPD6373	Approved
0.6588	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5697	Approved
0.6574	Remote Similarity	NPD5701	Approved
0.6552	Remote Similarity	NPD5360	Phase 3
0.6552	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7638	Approved
0.6518	Remote Similarity	NPD8133	Approved
0.6514	Remote Similarity	NPD7320	Approved
0.6514	Remote Similarity	NPD6881	Approved
0.6514	Remote Similarity	NPD6899	Approved
0.6514	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD4697	Phase 3
0.6491	Remote Similarity	NPD6009	Approved
0.6489	Remote Similarity	NPD6928	Phase 2
0.6486	Remote Similarity	NPD6649	Approved
0.6486	Remote Similarity	NPD6650	Approved
0.6477	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7639	Approved
0.6476	Remote Similarity	NPD7640	Approved
0.6471	Remote Similarity	NPD7900	Approved
0.6471	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6014	Approved
0.6455	Remote Similarity	NPD6013	Approved
0.6455	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD8297	Approved
0.641	Remote Similarity	NPD5983	Phase 2
0.6404	Remote Similarity	NPD6940	Discontinued
0.6396	Remote Similarity	NPD7102	Approved
0.6396	Remote Similarity	NPD7290	Approved
0.6396	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6883	Approved
0.6373	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD3573	Approved
0.6355	Remote Similarity	NPD7632	Discontinued
0.6346	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5222	Approved
0.6346	Remote Similarity	NPD5221	Approved
0.6339	Remote Similarity	NPD8130	Phase 1
0.6339	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6617	Approved
0.6339	Remote Similarity	NPD6847	Approved
0.6339	Remote Similarity	NPD6869	Approved
0.6333	Remote Similarity	NPD7507	Approved
0.6333	Remote Similarity	NPD4758	Discontinued
0.633	Remote Similarity	NPD6008	Approved
0.6321	Remote Similarity	NPD8418	Phase 2
0.6303	Remote Similarity	NPD7604	Phase 2
0.6286	Remote Similarity	NPD4755	Approved
0.6286	Remote Similarity	NPD5173	Approved
0.6283	Remote Similarity	NPD6882	Approved
0.6279	Remote Similarity	NPD371	Approved
0.6279	Remote Similarity	NPD7909	Approved
0.6273	Remote Similarity	NPD6412	Phase 2
0.6263	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD7492	Approved
0.6238	Remote Similarity	NPD5328	Approved
0.6214	Remote Similarity	NPD8171	Discontinued
0.6198	Remote Similarity	NPD6336	Discontinued
0.6198	Remote Similarity	NPD6616	Approved
0.6186	Remote Similarity	NPD6059	Approved
0.6186	Remote Similarity	NPD6054	Approved
0.6179	Remote Similarity	NPD7319	Approved
0.6168	Remote Similarity	NPD5285	Approved
0.6168	Remote Similarity	NPD5286	Approved
0.6168	Remote Similarity	NPD4700	Approved
0.6168	Remote Similarity	NPD4696	Approved
0.6148	Remote Similarity	NPD8293	Discontinued
0.6148	Remote Similarity	NPD7078	Approved
0.6134	Remote Similarity	NPD6015	Approved
0.6134	Remote Similarity	NPD6016	Approved
0.6132	Remote Similarity	NPD6084	Phase 2
0.6132	Remote Similarity	NPD6083	Phase 2
0.6126	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6274	Approved
0.6121	Remote Similarity	NPD6868	Approved
0.6117	Remote Similarity	NPD6079	Approved
0.6117	Remote Similarity	NPD6411	Approved
0.6111	Remote Similarity	NPD5223	Approved
0.6105	Remote Similarity	NPD4802	Phase 2
0.6105	Remote Similarity	NPD4238	Approved
0.6105	Remote Similarity	NPD5364	Discontinued
0.6083	Remote Similarity	NPD5988	Approved
0.6083	Remote Similarity	NPD6370	Approved
0.6078	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5696	Approved
0.6071	Remote Similarity	NPD6686	Approved
0.6068	Remote Similarity	NPD7115	Discovery
0.6068	Remote Similarity	NPD6317	Approved
0.6055	Remote Similarity	NPD5211	Phase 2
0.6055	Remote Similarity	NPD5225	Approved
0.6055	Remote Similarity	NPD5226	Approved
0.6055	Remote Similarity	NPD5224	Approved
0.6055	Remote Similarity	NPD4633	Approved
0.6044	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD1811	Approved
0.6022	Remote Similarity	NPD1810	Approved
0.602	Remote Similarity	NPD3667	Approved
0.6017	Remote Similarity	NPD6313	Approved
0.6017	Remote Similarity	NPD6335	Approved
0.6017	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6672	Approved
0.598	Remote Similarity	NPD5737	Approved
0.598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7100	Approved
0.5966	Remote Similarity	NPD7101	Approved
0.5946	Remote Similarity	NPD5141	Approved
0.5943	Remote Similarity	NPD5695	Phase 3
0.5926	Remote Similarity	NPD4225	Approved
0.5922	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6101	Approved
0.59	Remote Similarity	NPD4786	Approved
0.5893	Remote Similarity	NPD4767	Approved
0.5893	Remote Similarity	NPD4768	Approved
0.5893	Remote Similarity	NPD6920	Discontinued
0.5868	Remote Similarity	NPD6908	Approved
0.5868	Remote Similarity	NPD6909	Approved
0.584	Remote Similarity	NPD6033	Approved
0.5833	Remote Similarity	NPD7516	Approved
0.5804	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4788	Approved
0.5789	Remote Similarity	NPD4730	Approved
0.5789	Remote Similarity	NPD5128	Approved
0.5789	Remote Similarity	NPD5168	Approved
0.5789	Remote Similarity	NPD4729	Approved
0.5784	Remote Similarity	NPD7146	Approved
0.5784	Remote Similarity	NPD6684	Approved
0.5784	Remote Similarity	NPD5330	Approved
0.5784	Remote Similarity	NPD7521	Approved
0.5784	Remote Similarity	NPD6409	Approved
0.5784	Remote Similarity	NPD7334	Approved
0.5773	Remote Similarity	NPD3617	Approved
0.5769	Remote Similarity	NPD4753	Phase 2
0.5766	Remote Similarity	NPD8084	Approved
0.5766	Remote Similarity	NPD8082	Approved
0.5766	Remote Similarity	NPD8086	Approved
0.5766	Remote Similarity	NPD8138	Approved
0.5766	Remote Similarity	NPD8083	Approved
0.5766	Remote Similarity	NPD8085	Approved
0.5766	Remote Similarity	NPD8139	Approved
0.5755	Remote Similarity	NPD5778	Approved
0.5755	Remote Similarity	NPD4202	Approved
0.5755	Remote Similarity	NPD5779	Approved
0.575	Remote Similarity	NPD7327	Approved
0.575	Remote Similarity	NPD7328	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