NPASS Compound

Structure

CID318575 OpenBabel06191716142D 30 35 0 0 1 0 0 0 0 0999 V2000 1.4653 -1.8687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1714 -1.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0857 -1.2724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5510 -2.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3796 -1.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5837 -1.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1219 -0.8368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9697 -0.2168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9859 -3.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2898 -1.7463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3412 -3.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6367 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6787 -1.7369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2857 -3.1178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2571 -2.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0620 -2.6868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.7068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7280 -1.1742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6371 -0.5519 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8988 -1.9406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6694 -2.3425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9142 -2.2961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3736 -4.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6037 0.0423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5263 0.6499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0507 -4.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7289 -5.0291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2013 -2.5523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8380 -3.4736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 15 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 9 11 2 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 15 2 0 0 0 0 12 23 1 0 0 0 0 14 29 1 0 0 0 0 14 30 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 5 1 6 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 7 1 6 0 0 0 18 25 1 0 0 0 0 19 8 1 1 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 13 1 1 0 0 0 21 13 1 1 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.21
Volume:	426.255
LogP:	6.387
LogD:	4.79
LogS:	-3.948
# Rotatable Bonds:	8
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	5.618
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.754
MDCK Permeability:	2.341704566788394e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.686
30% Bioavailability (F30%):	0.483

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.333
Plasma Protein Binding (PPB):	98.99153137207031%
Volume Distribution (VD):	0.427
Pgp-substrate:	1.8702305555343628%

ADMET: Metabolism

CYP1A2-inhibitor:	0.831
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.323
CYP2C9-inhibitor:	0.774
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.708
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	7.629
Half-life (T1/2):	0.578

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.711
Drug-inuced Liver Injury (DILI):	0.298
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.427
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.808
Carcinogencity:	0.173
Eye Corrosion:	0.009
Eye Irritation:	0.027
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC318575

Natural Product ID:	NPC318575
*Common Name:**	JEVKBOABRNPNLG-VLZOBNMESA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Endiandric Acid L
Standard InCHIKey:	JEVKBOABRNPNLG-VLZOBNMESA-N
Standard InCHI:	InChI=1S/C26H30O4/c27-24(28)11-9-16-18-7-8-19-20(16)13-21-17(25(18)26(19)21)5-3-1-2-4-15-6-10-22-23(12-15)30-14-29-22/h6-12,16-21,25-26H,1-5,13-14H2,(H,27,28)/b11-9+/t16-,17-,18-,19+,20-,21-,25+,26-/m0/s1
SMILES:	OC(=O)/C=C/[C@H]1[C@@H]2C=C[C@@H]3[C@H]1C[C@H]1[C@@H]([C@H]2[C@@H]31)CCCCCc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821989
PubChem CID:	56678990
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	roots	Mudan, Pingtung County, Taiwan	2009-APR	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	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	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	Emax	=	91.42	%	PMID[547835]
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	39560.0	nM	PMID[547835]

☑ 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 NPC318575 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	353
0.1-0.2	1608
0.2-0.3	3244
0.3-0.4	8881
0.4-0.5	10526
0.5-0.6	9216
0.6-0.7	7804
0.7-0.8	1052
0.8-0.85	7
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9493	High Similarity	NPC189054
0.927	High Similarity	NPC323601
0.9051	High Similarity	NPC52968
0.9051	High Similarity	NPC231719
0.8473	Intermediate Similarity	NPC57501
0.8456	Intermediate Similarity	NPC64948
0.8414	Intermediate Similarity	NPC327623
0.8356	Intermediate Similarity	NPC271607
0.8356	Intermediate Similarity	NPC280717
0.8333	Intermediate Similarity	NPC69670
0.8322	Intermediate Similarity	NPC178290
0.8321	Intermediate Similarity	NPC177167
0.8309	Intermediate Similarity	NPC17348
0.8286	Intermediate Similarity	NPC227002
0.8284	Intermediate Similarity	NPC114845
0.8264	Intermediate Similarity	NPC275150
0.8243	Intermediate Similarity	NPC476336
0.8231	Intermediate Similarity	NPC19862
0.8231	Intermediate Similarity	NPC235195
0.8201	Intermediate Similarity	NPC476748
0.8182	Intermediate Similarity	NPC212643
0.8182	Intermediate Similarity	NPC199209
0.8175	Intermediate Similarity	NPC85830
0.8162	Intermediate Similarity	NPC249788
0.8148	Intermediate Similarity	NPC301641
0.8148	Intermediate Similarity	NPC80241
0.8143	Intermediate Similarity	NPC477694
0.8143	Intermediate Similarity	NPC477705
0.8134	Intermediate Similarity	NPC344161
0.8116	Intermediate Similarity	NPC213711
0.8116	Intermediate Similarity	NPC274356
0.8116	Intermediate Similarity	NPC40352
0.8088	Intermediate Similarity	NPC256167
0.8085	Intermediate Similarity	NPC477706
0.8082	Intermediate Similarity	NPC162851
0.8082	Intermediate Similarity	NPC218092
0.8082	Intermediate Similarity	NPC246474
0.8069	Intermediate Similarity	NPC76032
0.8069	Intermediate Similarity	NPC132723
0.8067	Intermediate Similarity	NPC96930
0.8067	Intermediate Similarity	NPC32017
0.8056	Intermediate Similarity	NPC230968
0.8056	Intermediate Similarity	NPC102260
0.8042	Intermediate Similarity	NPC471913
0.8013	Intermediate Similarity	NPC273358
0.8013	Intermediate Similarity	NPC298647
0.8013	Intermediate Similarity	NPC292206
0.8	Intermediate Similarity	NPC166184
0.7973	Intermediate Similarity	NPC125134
0.7973	Intermediate Similarity	NPC472564
0.7973	Intermediate Similarity	NPC137920
0.7973	Intermediate Similarity	NPC86455
0.7972	Intermediate Similarity	NPC205915
0.797	Intermediate Similarity	NPC471936
0.7961	Intermediate Similarity	NPC208785
0.7961	Intermediate Similarity	NPC470618
0.7961	Intermediate Similarity	NPC470619
0.7961	Intermediate Similarity	NPC12854
0.7961	Intermediate Similarity	NPC145527
0.7959	Intermediate Similarity	NPC28398
0.7959	Intermediate Similarity	NPC282291
0.7959	Intermediate Similarity	NPC166137
0.7956	Intermediate Similarity	NPC30462
0.7955	Intermediate Similarity	NPC294941
0.7947	Intermediate Similarity	NPC262804
0.7947	Intermediate Similarity	NPC40654
0.7929	Intermediate Similarity	NPC100129
0.7917	Intermediate Similarity	NPC19890
0.7917	Intermediate Similarity	NPC110958
0.7914	Intermediate Similarity	NPC9067
0.7902	Intermediate Similarity	NPC259742
0.7902	Intermediate Similarity	NPC219671
0.7902	Intermediate Similarity	NPC104077
0.7902	Intermediate Similarity	NPC147616
0.7899	Intermediate Similarity	NPC470887
0.7895	Intermediate Similarity	NPC127827
0.7891	Intermediate Similarity	NPC278076
0.7887	Intermediate Similarity	NPC134764
0.7887	Intermediate Similarity	NPC275950
0.7887	Intermediate Similarity	NPC171550
0.7883	Intermediate Similarity	NPC193484
0.7872	Intermediate Similarity	NPC478215
0.7871	Intermediate Similarity	NPC476364
0.7867	Intermediate Similarity	NPC307205
0.7862	Intermediate Similarity	NPC174191
0.7857	Intermediate Similarity	NPC213552
0.7857	Intermediate Similarity	NPC120225
0.7847	Intermediate Similarity	NPC169973
0.7843	Intermediate Similarity	NPC147224
0.7842	Intermediate Similarity	NPC60517
0.7842	Intermediate Similarity	NPC20443
0.7842	Intermediate Similarity	NPC146886
0.7838	Intermediate Similarity	NPC29599
0.7836	Intermediate Similarity	NPC111225
0.7832	Intermediate Similarity	NPC476345
0.7829	Intermediate Similarity	NPC308178
0.7817	Intermediate Similarity	NPC30174
0.7808	Intermediate Similarity	NPC90431
0.7808	Intermediate Similarity	NPC120852
0.7808	Intermediate Similarity	NPC476699
0.7806	Intermediate Similarity	NPC205392
0.7806	Intermediate Similarity	NPC105942
0.7801	Intermediate Similarity	NPC158737
0.78	Intermediate Similarity	NPC46880
0.7794	Intermediate Similarity	NPC37858
0.7792	Intermediate Similarity	NPC269914
0.7792	Intermediate Similarity	NPC478249
0.7786	Intermediate Similarity	NPC289459
0.7786	Intermediate Similarity	NPC228771
0.7786	Intermediate Similarity	NPC29008
0.7786	Intermediate Similarity	NPC266705
0.7786	Intermediate Similarity	NPC31279
0.7785	Intermediate Similarity	NPC104956
0.7785	Intermediate Similarity	NPC67467
0.7785	Intermediate Similarity	NPC52664
0.7778	Intermediate Similarity	NPC97316
0.7778	Intermediate Similarity	NPC471505
0.7778	Intermediate Similarity	NPC106739
0.7778	Intermediate Similarity	NPC24193
0.7778	Intermediate Similarity	NPC280001
0.7778	Intermediate Similarity	NPC286809
0.7771	Intermediate Similarity	NPC478248
0.7762	Intermediate Similarity	NPC181079
0.7762	Intermediate Similarity	NPC173308
0.7761	Intermediate Similarity	NPC475815
0.7761	Intermediate Similarity	NPC47194
0.7761	Intermediate Similarity	NPC473264
0.7754	Intermediate Similarity	NPC38996
0.7754	Intermediate Similarity	NPC70752
0.7754	Intermediate Similarity	NPC160380
0.7748	Intermediate Similarity	NPC247221
0.7746	Intermediate Similarity	NPC226862
0.7746	Intermediate Similarity	NPC158471
0.7746	Intermediate Similarity	NPC57119
0.7746	Intermediate Similarity	NPC165128
0.7742	Intermediate Similarity	NPC478268
0.774	Intermediate Similarity	NPC135777
0.774	Intermediate Similarity	NPC142547
0.774	Intermediate Similarity	NPC18576
0.773	Intermediate Similarity	NPC471930
0.773	Intermediate Similarity	NPC471935
0.773	Intermediate Similarity	NPC471929
0.7727	Intermediate Similarity	NPC475722
0.7727	Intermediate Similarity	NPC24425
0.7721	Intermediate Similarity	NPC277460
0.7721	Intermediate Similarity	NPC164706
0.7721	Intermediate Similarity	NPC137537
0.7721	Intermediate Similarity	NPC107588
0.7721	Intermediate Similarity	NPC272471
0.7721	Intermediate Similarity	NPC70744
0.7721	Intermediate Similarity	NPC124916
0.7718	Intermediate Similarity	NPC78987
0.7718	Intermediate Similarity	NPC82336
0.7714	Intermediate Similarity	NPC246704
0.7714	Intermediate Similarity	NPC471927
0.7712	Intermediate Similarity	NPC181464
0.7703	Intermediate Similarity	NPC226005
0.7702	Intermediate Similarity	NPC100420
0.7697	Intermediate Similarity	NPC475197
0.7697	Intermediate Similarity	NPC3982
0.7697	Intermediate Similarity	NPC472560
0.7697	Intermediate Similarity	NPC33832
0.7697	Intermediate Similarity	NPC473467
0.7692	Intermediate Similarity	NPC83062
0.7692	Intermediate Similarity	NPC89693
0.7692	Intermediate Similarity	NPC478241
0.7692	Intermediate Similarity	NPC229548
0.7692	Intermediate Similarity	NPC469699
0.7687	Intermediate Similarity	NPC143895
0.7687	Intermediate Similarity	NPC11453
0.7682	Intermediate Similarity	NPC15743
0.7682	Intermediate Similarity	NPC50696
0.7681	Intermediate Similarity	NPC204466
0.7676	Intermediate Similarity	NPC223807
0.7673	Intermediate Similarity	NPC179914
0.7673	Intermediate Similarity	NPC68619
0.7671	Intermediate Similarity	NPC67247
0.7671	Intermediate Similarity	NPC68779
0.7671	Intermediate Similarity	NPC5310
0.7671	Intermediate Similarity	NPC300776
0.7671	Intermediate Similarity	NPC176814
0.7671	Intermediate Similarity	NPC47181
0.7671	Intermediate Similarity	NPC4982
0.7669	Intermediate Similarity	NPC208818
0.7667	Intermediate Similarity	NPC191231
0.7667	Intermediate Similarity	NPC140502
0.7667	Intermediate Similarity	NPC287124
0.7662	Intermediate Similarity	NPC472567
0.7658	Intermediate Similarity	NPC11411
0.7658	Intermediate Similarity	NPC109765
0.7655	Intermediate Similarity	NPC239302
0.7651	Intermediate Similarity	NPC470855
0.7651	Intermediate Similarity	NPC110699
0.7651	Intermediate Similarity	NPC106055
0.7647	Intermediate Similarity	NPC304687
0.7647	Intermediate Similarity	NPC101755
0.7647	Intermediate Similarity	NPC65574
0.7647	Intermediate Similarity	NPC80230
0.7647	Intermediate Similarity	NPC104024
0.7643	Intermediate Similarity	NPC31344

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 NPC318575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	904
0.2-0.3	1548
0.3-0.4	2806
0.4-0.5	2170
0.5-0.6	1112
0.6-0.7	294
0.7-0.8	28
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
0.8389	Intermediate Similarity	NPD7028	Phase 2
0.7867	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD4626	Approved
0.7626	Intermediate Similarity	NPD3705	Approved
0.7612	Intermediate Similarity	NPD5283	Phase 1
0.758	Intermediate Similarity	NPD37	Approved
0.7547	Intermediate Similarity	NPD4966	Approved
0.7547	Intermediate Similarity	NPD4967	Phase 2
0.7547	Intermediate Similarity	NPD4965	Approved
0.7536	Intermediate Similarity	NPD1357	Approved
0.7534	Intermediate Similarity	NPD3620	Phase 2
0.7534	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7199	Phase 2
0.7453	Intermediate Similarity	NPD6234	Discontinued
0.7415	Intermediate Similarity	NPD4140	Approved
0.741	Intermediate Similarity	NPD5691	Approved
0.7394	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5536	Phase 2
0.7378	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD8127	Discontinued
0.732	Intermediate Similarity	NPD4110	Phase 3
0.732	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3657	Discovery
0.7241	Intermediate Similarity	NPD4624	Approved
0.7237	Intermediate Similarity	NPD5763	Approved
0.7237	Intermediate Similarity	NPD5762	Approved
0.7209	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8166	Discontinued
0.7206	Intermediate Similarity	NPD228	Approved
0.72	Intermediate Similarity	NPD2492	Phase 1
0.717	Intermediate Similarity	NPD7458	Discontinued
0.7164	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD7228	Approved
0.7124	Intermediate Similarity	NPD7266	Discontinued
0.7114	Intermediate Similarity	NPD8032	Phase 2
0.7107	Intermediate Similarity	NPD1653	Approved
0.7103	Intermediate Similarity	NPD1283	Approved
0.709	Intermediate Similarity	NPD3134	Approved
0.7089	Intermediate Similarity	NPD6273	Approved
0.7034	Intermediate Similarity	NPD5327	Phase 3
0.7032	Intermediate Similarity	NPD6674	Discontinued
0.702	Intermediate Similarity	NPD5735	Approved
0.7014	Intermediate Similarity	NPD1281	Approved
0.6994	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1876	Approved
0.698	Remote Similarity	NPD7095	Approved
0.6977	Remote Similarity	NPD7685	Pre-registration
0.6974	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6353	Approved
0.6959	Remote Similarity	NPD5736	Approved
0.6944	Remote Similarity	NPD3496	Discontinued
0.6918	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6355	Discontinued
0.6906	Remote Similarity	NPD5535	Approved
0.6887	Remote Similarity	NPD6663	Approved
0.6883	Remote Similarity	NPD4108	Discontinued
0.6879	Remote Similarity	NPD7003	Approved
0.6879	Remote Similarity	NPD7240	Approved
0.6875	Remote Similarity	NPD2932	Approved
0.6867	Remote Similarity	NPD3027	Phase 3
0.6863	Remote Similarity	NPD6653	Approved
0.6857	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2861	Phase 2
0.6842	Remote Similarity	NPD2979	Phase 3
0.6839	Remote Similarity	NPD2438	Suspended
0.6839	Remote Similarity	NPD2935	Discontinued
0.6824	Remote Similarity	NPD2898	Approved
0.6821	Remote Similarity	NPD5111	Phase 2
0.6821	Remote Similarity	NPD5109	Approved
0.6821	Remote Similarity	NPD5110	Phase 2
0.6818	Remote Similarity	NPD7097	Phase 1
0.6812	Remote Similarity	NPD3022	Approved
0.6812	Remote Similarity	NPD3021	Approved
0.6806	Remote Similarity	NPD1651	Approved
0.6805	Remote Similarity	NPD6232	Discontinued
0.6798	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1933	Approved
0.6784	Remote Similarity	NPD7473	Discontinued
0.6779	Remote Similarity	NPD2798	Approved
0.6779	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4628	Phase 3
0.6772	Remote Similarity	NPD6331	Phase 2
0.6772	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6873	Phase 2
0.6761	Remote Similarity	NPD7157	Approved
0.6759	Remote Similarity	NPD3019	Approved
0.6755	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2157	Approved
0.6747	Remote Similarity	NPD5977	Approved
0.6747	Remote Similarity	NPD5978	Approved
0.6744	Remote Similarity	NPD3818	Discontinued
0.6739	Remote Similarity	NPD2684	Approved
0.6736	Remote Similarity	NPD3091	Approved
0.6733	Remote Similarity	NPD9494	Approved
0.6731	Remote Similarity	NPD2161	Phase 2
0.6712	Remote Similarity	NPD3847	Discontinued
0.6711	Remote Similarity	NPD3764	Approved
0.6711	Remote Similarity	NPD2797	Approved
0.6705	Remote Similarity	NPD5844	Phase 1
0.6688	Remote Similarity	NPD4340	Discontinued
0.6688	Remote Similarity	NPD447	Suspended
0.6688	Remote Similarity	NPD1375	Discontinued
0.6687	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7831	Phase 2
0.6667	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1138	Approved
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD7833	Phase 2
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6667	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2653	Approved
0.6645	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4097	Suspended
0.6644	Remote Similarity	NPD4059	Approved
0.6644	Remote Similarity	NPD8651	Approved
0.6644	Remote Similarity	NPD3095	Discontinued
0.6628	Remote Similarity	NPD4481	Phase 3
0.6627	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2531	Phase 2
0.6605	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6798	Discontinued
0.6601	Remote Similarity	NPD3268	Approved
0.66	Remote Similarity	NPD3094	Phase 2
0.6599	Remote Similarity	NPD3026	Approved
0.6599	Remote Similarity	NPD3023	Approved
0.6596	Remote Similarity	NPD1139	Approved
0.6596	Remote Similarity	NPD1137	Approved
0.6585	Remote Similarity	NPD4210	Discontinued
0.6582	Remote Similarity	NPD2346	Discontinued
0.6582	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6004	Phase 3
0.6582	Remote Similarity	NPD6005	Phase 3
0.6582	Remote Similarity	NPD6002	Phase 3
0.6579	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2983	Phase 2
0.6577	Remote Similarity	NPD2982	Phase 2
0.6575	Remote Similarity	NPD3025	Approved
0.6575	Remote Similarity	NPD3024	Approved
0.6575	Remote Similarity	NPD5585	Approved
0.6564	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3750	Approved
0.6556	Remote Similarity	NPD5647	Approved
0.6543	Remote Similarity	NPD4357	Discontinued
0.6541	Remote Similarity	NPD5958	Discontinued
0.6541	Remote Similarity	NPD7037	Approved
0.6528	Remote Similarity	NPD709	Approved
0.6524	Remote Similarity	NPD5699	Approved
0.6524	Remote Similarity	NPD4727	Phase 1
0.6522	Remote Similarity	NPD9697	Approved
0.6517	Remote Similarity	NPD7281	Phase 3
0.6517	Remote Similarity	NPD7280	Phase 3
0.6516	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD1613	Approved
0.6513	Remote Similarity	NPD3018	Phase 2
0.6513	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3972	Approved
0.651	Remote Similarity	NPD1608	Approved
0.651	Remote Similarity	NPD2233	Approved
0.651	Remote Similarity	NPD2981	Phase 2
0.651	Remote Similarity	NPD2232	Approved
0.651	Remote Similarity	NPD2230	Approved
0.6509	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1241	Discontinued
0.6503	Remote Similarity	NPD4739	Approved
0.6503	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6896	Approved
0.6497	Remote Similarity	NPD6559	Discontinued
0.6497	Remote Similarity	NPD6895	Approved
0.6491	Remote Similarity	NPD5494	Approved
0.649	Remote Similarity	NPD987	Approved
0.6488	Remote Similarity	NPD2978	Approved
0.6488	Remote Similarity	NPD2977	Approved
0.6479	Remote Similarity	NPD969	Suspended
0.6474	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5124	Phase 1
0.6471	Remote Similarity	NPD2614	Approved
0.6467	Remote Similarity	NPD1669	Approved
0.6467	Remote Similarity	NPD4749	Approved
0.6463	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3748	Approved
0.6454	Remote Similarity	NPD5451	Approved
0.6452	Remote Similarity	NPD2674	Phase 3
0.6452	Remote Similarity	NPD6233	Phase 2
0.645	Remote Similarity	NPD3817	Phase 2
0.6443	Remote Similarity	NPD422	Phase 1
0.6443	Remote Similarity	NPD1091	Approved
0.6438	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD970	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