NPASS Compound

Structure

NPC475818 OpenBabel07101718302D 29 30 0 0 1 0 0 0 0 0999 V2000 5.9292 -2.0377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6879 0.5838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4841 -1.6756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0518 0.3581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3112 -0.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4788 -1.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9473 -0.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9653 0.7648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2247 -0.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6698 -0.8175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5021 -0.2743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3924 -0.9985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2014 -2.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1525 -2.8953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1525 -1.2773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0337 -1.0431 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.7743 0.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 -0.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2014 -1.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 -2.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7402 -2.0863 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 17 28 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 23 16 1 6 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 25 27 2 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.25
Volume:	440.549
LogP:	4.967
LogD:	4.828
LogS:	-4.873
# Rotatable Bonds:	11
TPSA:	66.74
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	4.123
Fsp3:	0.44
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:	-4.79
MDCK Permeability:	2.5665398425189778e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	98.60832214355469%
Volume Distribution (VD):	1.61
Pgp-substrate:	1.0859934091567993%

ADMET: Metabolism

CYP1A2-inhibitor:	0.362
CYP1A2-substrate:	0.644
CYP2C19-inhibitor:	0.792
CYP2C19-substrate:	0.137
CYP2C9-inhibitor:	0.77
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.9
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	6.751
Half-life (T1/2):	0.61

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.674
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.144
Skin Sensitization:	0.303
Carcinogencity:	0.364
Eye Corrosion:	0.003
Eye Irritation:	0.171
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: NPC475818

Natural Product ID:	NPC475818
*Common Name:**	Isopalinurin
IUPAC Name:	(2R)-2-[(2E,4E,10E)-13-(furan-3-yl)-2,6,10-trimethyltrideca-2,4,10-trienyl]-3-hydroxy-4-methyl-2H-furan-5-one
Synonyms:	Isopalinurin
Standard InCHIKey:	PZPXBUTUKYKUCW-KKGPLOBWSA-N
Standard InCHI:	InChI=1S/C25H34O4/c1-18(8-5-9-19(2)11-7-13-22-14-15-28-17-22)10-6-12-20(3)16-23-24(26)21(4)25(27)29-23/h6,10-12,14-15,17-18,23,26H,5,7-9,13,16H2,1-4H3/b10-6+,19-11+,20-12+/t18?,23-/m1/s1
SMILES:	CC(/C=C/C=C(/C[C@H]1OC(=O)C(=C1O)C)C)CCC/C(=C/CCc1cocc1)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516676
PubChem CID:	54726685
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270579]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	Korean	n.a.	PMID[23489626]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621941]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[547822]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	16.5	ug ml-1	PMID[547822]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	10.7	ug ml-1	PMID[547822]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	10.0	ug ml-1	PMID[547822]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[547822]

☑ 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 NPC475818 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	236
0.1-0.2	1084
0.2-0.3	4056
0.3-0.4	9743
0.4-0.5	10675
0.5-0.6	10943
0.6-0.7	5461
0.7-0.8	430
0.8-0.85	26
0.85-0.9	24
0.9-0.95	10
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC329694
0.9746	High Similarity	NPC81912
0.9746	High Similarity	NPC329922
0.9746	High Similarity	NPC474260
0.9741	High Similarity	NPC289911
0.9741	High Similarity	NPC283284
0.9739	High Similarity	NPC474817
0.9655	High Similarity	NPC474136
0.95	High Similarity	NPC476016
0.9496	High Similarity	NPC71274
0.9496	High Similarity	NPC75557
0.9492	High Similarity	NPC476351
0.9421	High Similarity	NPC474438
0.9421	High Similarity	NPC474279
0.9339	High Similarity	NPC474830
0.931	High Similarity	NPC131801
0.9174	High Similarity	NPC474829
0.9153	High Similarity	NPC473969
0.9016	High Similarity	NPC471559
0.8983	High Similarity	NPC144745
0.8983	High Similarity	NPC208906
0.8889	High Similarity	NPC17681
0.8879	High Similarity	NPC1811
0.8879	High Similarity	NPC26157
0.8871	High Similarity	NPC471554
0.8871	High Similarity	NPC473355
0.8871	High Similarity	NPC471573
0.8871	High Similarity	NPC471501
0.8828	High Similarity	NPC288209
0.8819	High Similarity	NPC97740
0.8793	High Similarity	NPC105249
0.877	High Similarity	NPC471549
0.877	High Similarity	NPC473379
0.8696	High Similarity	NPC471521
0.8696	High Similarity	NPC473356
0.8689	High Similarity	NPC1848
0.8678	High Similarity	NPC4898
0.8672	High Similarity	NPC45358
0.8626	High Similarity	NPC215109
0.8626	High Similarity	NPC170604
0.8615	High Similarity	NPC14650
0.8605	High Similarity	NPC474425
0.8605	High Similarity	NPC474426
0.8605	High Similarity	NPC474407
0.8595	High Similarity	NPC187547
0.8595	High Similarity	NPC21831
0.8571	High Similarity	NPC137570
0.848	Intermediate Similarity	NPC243269
0.8468	Intermediate Similarity	NPC263870
0.8462	Intermediate Similarity	NPC177331
0.8409	Intermediate Similarity	NPC303217
0.8222	Intermediate Similarity	NPC107571
0.8203	Intermediate Similarity	NPC138139
0.8203	Intermediate Similarity	NPC46536
0.8197	Intermediate Similarity	NPC28054
0.8189	Intermediate Similarity	NPC118853
0.8189	Intermediate Similarity	NPC188377
0.8189	Intermediate Similarity	NPC65735
0.8175	Intermediate Similarity	NPC477967
0.8168	Intermediate Similarity	NPC89133
0.814	Intermediate Similarity	NPC83178
0.8106	Intermediate Similarity	NPC471544
0.8106	Intermediate Similarity	NPC473344
0.8106	Intermediate Similarity	NPC471545
0.8077	Intermediate Similarity	NPC207294
0.8077	Intermediate Similarity	NPC112706
0.8074	Intermediate Similarity	NPC473268
0.8065	Intermediate Similarity	NPC312525
0.8065	Intermediate Similarity	NPC217180
0.806	Intermediate Similarity	NPC159786
0.8058	Intermediate Similarity	NPC267004
0.8058	Intermediate Similarity	NPC218712
0.8058	Intermediate Similarity	NPC307346
0.8058	Intermediate Similarity	NPC261733
0.7984	Intermediate Similarity	NPC179354
0.797	Intermediate Similarity	NPC471817
0.797	Intermediate Similarity	NPC473982
0.7969	Intermediate Similarity	NPC16922
0.7956	Intermediate Similarity	NPC90953
0.7953	Intermediate Similarity	NPC79557
0.7943	Intermediate Similarity	NPC104924
0.7926	Intermediate Similarity	NPC476947
0.792	Intermediate Similarity	NPC227660
0.791	Intermediate Similarity	NPC218838
0.7907	Intermediate Similarity	NPC477965
0.7907	Intermediate Similarity	NPC477038
0.7903	Intermediate Similarity	NPC205523
0.7902	Intermediate Similarity	NPC234494
0.7895	Intermediate Similarity	NPC298190
0.7895	Intermediate Similarity	NPC136340
0.7891	Intermediate Similarity	NPC317217
0.7863	Intermediate Similarity	NPC95567
0.7863	Intermediate Similarity	NPC319140
0.7857	Intermediate Similarity	NPC291619
0.7857	Intermediate Similarity	NPC80635
0.7857	Intermediate Similarity	NPC243704
0.7857	Intermediate Similarity	NPC254958
0.7857	Intermediate Similarity	NPC254198
0.784	Intermediate Similarity	NPC45536
0.781	Intermediate Similarity	NPC186626
0.7794	Intermediate Similarity	NPC92941
0.7786	Intermediate Similarity	NPC216810
0.7786	Intermediate Similarity	NPC121158
0.7786	Intermediate Similarity	NPC23086
0.7786	Intermediate Similarity	NPC74612
0.7778	Intermediate Similarity	NPC470740
0.7778	Intermediate Similarity	NPC125182
0.7778	Intermediate Similarity	NPC69647
0.7762	Intermediate Similarity	NPC255414
0.7761	Intermediate Similarity	NPC61788
0.776	Intermediate Similarity	NPC150895
0.7746	Intermediate Similarity	NPC34056
0.774	Intermediate Similarity	NPC33938
0.774	Intermediate Similarity	NPC121615
0.774	Intermediate Similarity	NPC294511
0.7737	Intermediate Similarity	NPC146872
0.773	Intermediate Similarity	NPC267632
0.7724	Intermediate Similarity	NPC470997
0.7721	Intermediate Similarity	NPC106247
0.7708	Intermediate Similarity	NPC7388
0.7698	Intermediate Similarity	NPC476014
0.7698	Intermediate Similarity	NPC476031
0.7698	Intermediate Similarity	NPC202260
0.7687	Intermediate Similarity	NPC253201
0.7687	Intermediate Similarity	NPC98206
0.7687	Intermediate Similarity	NPC34421
0.7687	Intermediate Similarity	NPC237259
0.7687	Intermediate Similarity	NPC302054
0.7687	Intermediate Similarity	NPC21460
0.7681	Intermediate Similarity	NPC470742
0.768	Intermediate Similarity	NPC292036
0.7676	Intermediate Similarity	NPC251865
0.7676	Intermediate Similarity	NPC137295
0.7669	Intermediate Similarity	NPC477123
0.7669	Intermediate Similarity	NPC477966
0.7669	Intermediate Similarity	NPC477039
0.7669	Intermediate Similarity	NPC477040
0.7651	Intermediate Similarity	NPC472777
0.7651	Intermediate Similarity	NPC472778
0.7651	Intermediate Similarity	NPC472776
0.7643	Intermediate Similarity	NPC56197
0.7639	Intermediate Similarity	NPC216755
0.7639	Intermediate Similarity	NPC471174
0.7635	Intermediate Similarity	NPC296807
0.7635	Intermediate Similarity	NPC155939
0.7635	Intermediate Similarity	NPC141538
0.7634	Intermediate Similarity	NPC130275
0.763	Intermediate Similarity	NPC475092
0.7626	Intermediate Similarity	NPC236532
0.7622	Intermediate Similarity	NPC195920
0.7619	Intermediate Similarity	NPC474378
0.7619	Intermediate Similarity	NPC474219
0.7619	Intermediate Similarity	NPC472672
0.7619	Intermediate Similarity	NPC268905
0.7615	Intermediate Similarity	NPC174915
0.7615	Intermediate Similarity	NPC270807
0.7612	Intermediate Similarity	NPC120836
0.7612	Intermediate Similarity	NPC223063
0.7606	Intermediate Similarity	NPC476946
0.7606	Intermediate Similarity	NPC22248
0.7603	Intermediate Similarity	NPC228842
0.7586	Intermediate Similarity	NPC93666
0.7586	Intermediate Similarity	NPC471007
0.7578	Intermediate Similarity	NPC293424
0.7569	Intermediate Similarity	NPC346
0.7559	Intermediate Similarity	NPC474987
0.7559	Intermediate Similarity	NPC76844
0.7556	Intermediate Similarity	NPC476925
0.7554	Intermediate Similarity	NPC310830
0.7552	Intermediate Similarity	NPC476944
0.7541	Intermediate Similarity	NPC140688
0.7537	Intermediate Similarity	NPC476917
0.7537	Intermediate Similarity	NPC26532
0.7537	Intermediate Similarity	NPC327527
0.7537	Intermediate Similarity	NPC329707
0.7535	Intermediate Similarity	NPC52412
0.7534	Intermediate Similarity	NPC472654
0.7533	Intermediate Similarity	NPC88007
0.7533	Intermediate Similarity	NPC7059
0.7533	Intermediate Similarity	NPC197137
0.7533	Intermediate Similarity	NPC194499
0.752	Intermediate Similarity	NPC22678
0.7519	Intermediate Similarity	NPC244862
0.7519	Intermediate Similarity	NPC67345
0.7518	Intermediate Similarity	NPC201370
0.7518	Intermediate Similarity	NPC67003
0.7518	Intermediate Similarity	NPC282973
0.7518	Intermediate Similarity	NPC148374
0.7518	Intermediate Similarity	NPC473983
0.7517	Intermediate Similarity	NPC250228
0.7517	Intermediate Similarity	NPC92979
0.7517	Intermediate Similarity	NPC302987
0.7517	Intermediate Similarity	NPC71821
0.7517	Intermediate Similarity	NPC281258
0.7517	Intermediate Similarity	NPC214541
0.7517	Intermediate Similarity	NPC476938
0.7517	Intermediate Similarity	NPC44675
0.7517	Intermediate Similarity	NPC476937
0.75	Intermediate Similarity	NPC220094
0.75	Intermediate Similarity	NPC477645

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 NPC475818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	886
0.2-0.3	2083
0.3-0.4	2888
0.4-0.5	1886
0.5-0.6	958
0.6-0.7	232
0.7-0.8	9
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
0.7447	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6355	Discontinued
0.7292	Intermediate Similarity	NPD4628	Phase 3
0.7206	Intermediate Similarity	NPD5647	Approved
0.7164	Intermediate Similarity	NPD9717	Approved
0.7122	Intermediate Similarity	NPD6798	Discontinued
0.712	Intermediate Similarity	NPD1358	Approved
0.7101	Intermediate Similarity	NPD6832	Phase 2
0.7099	Intermediate Similarity	NPD9092	Discovery
0.7042	Intermediate Similarity	NPD6653	Approved
0.704	Intermediate Similarity	NPD3134	Approved
0.695	Remote Similarity	NPD6233	Phase 2
0.695	Remote Similarity	NPD4062	Phase 3
0.6948	Remote Similarity	NPD5761	Phase 2
0.6948	Remote Similarity	NPD5760	Phase 2
0.6944	Remote Similarity	NPD2799	Discontinued
0.6906	Remote Similarity	NPD9494	Approved
0.6884	Remote Similarity	NPD2797	Approved
0.6884	Remote Similarity	NPD1203	Approved
0.6884	Remote Similarity	NPD6362	Approved
0.6884	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD447	Suspended
0.6846	Remote Similarity	NPD7843	Approved
0.6839	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1019	Discontinued
0.6822	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6273	Approved
0.68	Remote Similarity	NPD6799	Approved
0.6797	Remote Similarity	NPD2684	Approved
0.6794	Remote Similarity	NPD1241	Discontinued
0.6791	Remote Similarity	NPD9545	Approved
0.6781	Remote Similarity	NPD1551	Phase 2
0.6779	Remote Similarity	NPD3887	Approved
0.6779	Remote Similarity	NPD2354	Approved
0.6761	Remote Similarity	NPD2313	Discontinued
0.6761	Remote Similarity	NPD3268	Approved
0.6759	Remote Similarity	NPD7097	Phase 1
0.6742	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1933	Approved
0.6735	Remote Similarity	NPD6005	Phase 3
0.6735	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6002	Phase 3
0.6735	Remote Similarity	NPD6004	Phase 3
0.6727	Remote Similarity	NPD6765	Approved
0.6727	Remote Similarity	NPD6764	Approved
0.6726	Remote Similarity	NPD8434	Phase 2
0.6719	Remote Similarity	NPD290	Approved
0.6715	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4308	Phase 3
0.6711	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4110	Phase 3
0.6709	Remote Similarity	NPD7075	Discontinued
0.6692	Remote Similarity	NPD7157	Approved
0.6691	Remote Similarity	NPD1778	Approved
0.669	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD5958	Discontinued
0.6689	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6645	Remote Similarity	NPD5401	Approved
0.6645	Remote Similarity	NPD6599	Discontinued
0.6643	Remote Similarity	NPD411	Approved
0.6643	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD9493	Approved
0.6642	Remote Similarity	NPD3496	Discontinued
0.6627	Remote Similarity	NPD6559	Discontinued
0.6623	Remote Similarity	NPD7440	Discontinued
0.6622	Remote Similarity	NPD5763	Approved
0.6622	Remote Similarity	NPD5762	Approved
0.6622	Remote Similarity	NPD2344	Approved
0.6621	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5585	Approved
0.6615	Remote Similarity	NPD2067	Discontinued
0.6601	Remote Similarity	NPD5049	Phase 3
0.6599	Remote Similarity	NPD7033	Discontinued
0.6596	Remote Similarity	NPD2798	Approved
0.6581	Remote Similarity	NPD7458	Discontinued
0.6581	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4534	Discontinued
0.6568	Remote Similarity	NPD6785	Approved
0.6568	Remote Similarity	NPD6784	Approved
0.6561	Remote Similarity	NPD6801	Discontinued
0.6558	Remote Similarity	NPD920	Approved
0.6554	Remote Similarity	NPD2239	Approved
0.6554	Remote Similarity	NPD2935	Discontinued
0.6554	Remote Similarity	NPD2240	Approved
0.6552	Remote Similarity	NPD4060	Phase 1
0.6552	Remote Similarity	NPD4307	Phase 2
0.6536	Remote Similarity	NPD4661	Approved
0.6536	Remote Similarity	NPD4662	Approved
0.6525	Remote Similarity	NPD3266	Approved
0.6525	Remote Similarity	NPD3267	Approved
0.6522	Remote Similarity	NPD3847	Discontinued
0.6515	Remote Similarity	NPD969	Suspended
0.6513	Remote Similarity	NPD643	Clinical (unspecified phase)
0.651	Remote Similarity	NPD2353	Approved
0.651	Remote Similarity	NPD2346	Discontinued
0.651	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2424	Discontinued
0.6466	Remote Similarity	NPD5535	Approved
0.646	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.646	Remote Similarity	NPD919	Approved
0.6458	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD1876	Approved
0.6454	Remote Similarity	NPD3225	Approved
0.6449	Remote Similarity	NPD17	Approved
0.6447	Remote Similarity	NPD2309	Approved
0.6443	Remote Similarity	NPD6032	Approved
0.6438	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD9697	Approved
0.6429	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1481	Phase 2
0.6429	Remote Similarity	NPD3972	Approved
0.6415	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7819	Suspended
0.6414	Remote Similarity	NPD3764	Approved
0.6412	Remote Similarity	NPD2182	Approved
0.6408	Remote Similarity	NPD987	Approved
0.6392	Remote Similarity	NPD6677	Suspended
0.6392	Remote Similarity	NPD7411	Suspended
0.6389	Remote Similarity	NPD2614	Approved
0.6383	Remote Similarity	NPD4359	Approved
0.6382	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7003	Approved
0.6382	Remote Similarity	NPD3750	Approved
0.638	Remote Similarity	NPD8127	Discontinued
0.6375	Remote Similarity	NPD5402	Approved
0.6364	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1549	Phase 2
0.6357	Remote Similarity	NPD1535	Discovery
0.635	Remote Similarity	NPD5536	Phase 2
0.6338	Remote Similarity	NPD1283	Approved
0.6335	Remote Similarity	NPD7768	Phase 2
0.6335	Remote Similarity	NPD3882	Suspended
0.6333	Remote Similarity	NPD2438	Suspended
0.6333	Remote Similarity	NPD4477	Approved
0.6333	Remote Similarity	NPD2796	Approved
0.6333	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5712	Approved
0.6333	Remote Similarity	NPD4476	Approved
0.6327	Remote Similarity	NPD4140	Approved
0.6327	Remote Similarity	NPD3142	Approved
0.6327	Remote Similarity	NPD3140	Approved
0.6323	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD454	Approved
0.6316	Remote Similarity	NPD1243	Approved
0.6301	Remote Similarity	NPD1048	Approved
0.6299	Remote Similarity	NPD1238	Approved
0.6296	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1471	Phase 3
0.6291	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD958	Approved
0.6284	Remote Similarity	NPD4622	Approved
0.6284	Remote Similarity	NPD4618	Approved
0.6284	Remote Similarity	NPD230	Phase 1
0.6284	Remote Similarity	NPD4340	Discontinued
0.6279	Remote Similarity	NPD6647	Phase 2
0.6275	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD3817	Phase 2
0.6268	Remote Similarity	NPD3685	Discontinued
0.6267	Remote Similarity	NPD3748	Approved
0.6266	Remote Similarity	NPD2651	Approved
0.6266	Remote Similarity	NPD2649	Approved
0.6259	Remote Similarity	NPD8032	Phase 2
0.6259	Remote Similarity	NPD5691	Approved
0.625	Remote Similarity	NPD2629	Approved
0.625	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2897	Discontinued
0.625	Remote Similarity	NPD1934	Approved
0.6242	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD6808	Phase 2
0.6241	Remote Similarity	NPD1091	Approved
0.6233	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4380	Phase 2
0.6216	Remote Similarity	NPD2979	Phase 3
0.6214	Remote Similarity	NPD4626	Approved
0.6211	Remote Similarity	NPD8455	Phase 2
0.6211	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD1652	Phase 2
0.6202	Remote Similarity	NPD291	Approved
0.62	Remote Similarity	NPD5688	Approved
0.62	Remote Similarity	NPD5689	Approved
0.6196	Remote Similarity	NPD3749	Approved
0.6196	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3818	Discontinued
0.619	Remote Similarity	NPD2163	Approved
0.6182	Remote Similarity	NPD7199	Phase 2
0.6178	Remote Similarity	NPD2186	Approved
0.6174	Remote Similarity	NPD5124	Phase 1

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