NPASS Compound

Structure

NPC472254 OpenBabel07101719142D 25 25 0 0 1 0 0 0 0 0999 V2000 1.2271 2.2147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5226 3.7970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -4.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5316 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1180 -3.2709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6000 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4954 2.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5135 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 -2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4181 2.8025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6180 -2.4049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 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 2.1180 -1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6180 -2.4049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1180 -1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 17 4 1 6 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 17 1 1 0 0 0 20 21 1 0 0 0 0 21 24 1 1 0 0 0 22 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.27
Volume:	396.337
LogP:	5.203
LogD:	4.522
LogS:	-5.031
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	4.628
Fsp3:	0.682
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:	-4.609
MDCK Permeability:	3.487903086352162e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.889
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.74

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	95.50890350341797%
Volume Distribution (VD):	1.485
Pgp-substrate:	5.914642810821533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.132
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.605
CYP2C9-inhibitor:	0.391
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.414
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	6.857
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.92
Drug-inuced Liver Injury (DILI):	0.646
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.783
Carcinogencity:	0.036
Eye Corrosion:	0.006
Eye Irritation:	0.026
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC472254

Natural Product ID:	NPC472254
*Common Name:**	PTGSYIPWFAXRLD-FFJUBWNPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PTGSYIPWFAXRLD-FFJUBWNPSA-N
Standard InCHI:	InChI=1S/C22H36O3/c1-15(2)8-7-9-17(4)20-12-10-16(3)11-13-22(25-19(6)23)18(5)14-21(20)24/h8,11,14,17,20-22,24H,7,9-10,12-13H2,1-6H3/b16-11+,18-14+/t17-,20+,21+,22+/m1/s1
SMILES:	CC1=CCC(C(=CC(C(CC1)C(C)CCC=C(C)C)O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3355404
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32773	dictyota plectens	Species	Dictyotaceae	Eukaryota	n.a.	China	n.a.	PMID[25495797]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	60000.0	nM	PMID[537114]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[537114]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	30500.0	nM	PMID[537114]

☑ 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 NPC472254 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	171
0.1-0.2	1303
0.2-0.3	6001
0.3-0.4	16961
0.4-0.5	9494
0.5-0.6	6011
0.6-0.7	2349
0.7-0.8	388
0.8-0.85	10
0.85-0.9	5
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC4299
0.9118	High Similarity	NPC101622
0.8784	High Similarity	NPC86971
0.8732	High Similarity	NPC477085
0.8592	High Similarity	NPC477087
0.8592	High Similarity	NPC477086
0.8514	High Similarity	NPC84360
0.8451	Intermediate Similarity	NPC473361
0.8451	Intermediate Similarity	NPC329904
0.8289	Intermediate Similarity	NPC325869
0.8289	Intermediate Similarity	NPC89128
0.8267	Intermediate Similarity	NPC476439
0.8182	Intermediate Similarity	NPC155025
0.8133	Intermediate Similarity	NPC469880
0.8077	Intermediate Similarity	NPC112868
0.8077	Intermediate Similarity	NPC52861
0.806	Intermediate Similarity	NPC122239
0.8052	Intermediate Similarity	NPC477088
0.8052	Intermediate Similarity	NPC471537
0.8052	Intermediate Similarity	NPC242767
0.8028	Intermediate Similarity	NPC472266
0.8026	Intermediate Similarity	NPC262747
0.8026	Intermediate Similarity	NPC40049
0.8	Intermediate Similarity	NPC476804
0.7971	Intermediate Similarity	NPC473508
0.7941	Intermediate Similarity	NPC99487
0.7922	Intermediate Similarity	NPC471465
0.7922	Intermediate Similarity	NPC196653
0.7922	Intermediate Similarity	NPC209135
0.7922	Intermediate Similarity	NPC474816
0.7901	Intermediate Similarity	NPC255307
0.7895	Intermediate Similarity	NPC256720
0.7895	Intermediate Similarity	NPC236228
0.7879	Intermediate Similarity	NPC96663
0.7875	Intermediate Similarity	NPC472473
0.7875	Intermediate Similarity	NPC23748
0.7875	Intermediate Similarity	NPC42476
0.7875	Intermediate Similarity	NPC231601
0.7848	Intermediate Similarity	NPC475944
0.7848	Intermediate Similarity	NPC474894
0.7848	Intermediate Similarity	NPC315731
0.7838	Intermediate Similarity	NPC316185
0.7838	Intermediate Similarity	NPC477084
0.7821	Intermediate Similarity	NPC139712
0.7808	Intermediate Similarity	NPC269841
0.7808	Intermediate Similarity	NPC151481
0.7805	Intermediate Similarity	NPC475461
0.7805	Intermediate Similarity	NPC305475
0.7794	Intermediate Similarity	NPC475931
0.7792	Intermediate Similarity	NPC116177
0.7792	Intermediate Similarity	NPC315394
0.7792	Intermediate Similarity	NPC7563
0.7792	Intermediate Similarity	NPC320630
0.7778	Intermediate Similarity	NPC191476
0.7778	Intermediate Similarity	NPC114979
0.7778	Intermediate Similarity	NPC474776
0.7778	Intermediate Similarity	NPC96259
0.7778	Intermediate Similarity	NPC141193
0.7763	Intermediate Similarity	NPC329852
0.7746	Intermediate Similarity	NPC308844
0.7722	Intermediate Similarity	NPC474739
0.7703	Intermediate Similarity	NPC469660
0.7683	Intermediate Similarity	NPC471494
0.7683	Intermediate Similarity	NPC35933
0.7683	Intermediate Similarity	NPC261380
0.7671	Intermediate Similarity	NPC305698
0.7671	Intermediate Similarity	NPC272961
0.7662	Intermediate Similarity	NPC476317
0.7662	Intermediate Similarity	NPC68819
0.7662	Intermediate Similarity	NPC477202
0.7662	Intermediate Similarity	NPC271070
0.7662	Intermediate Similarity	NPC61863
0.7654	Intermediate Similarity	NPC473390
0.7654	Intermediate Similarity	NPC161045
0.7654	Intermediate Similarity	NPC311070
0.7654	Intermediate Similarity	NPC40746
0.7654	Intermediate Similarity	NPC474809
0.7654	Intermediate Similarity	NPC49208
0.7654	Intermediate Similarity	NPC472377
0.7654	Intermediate Similarity	NPC169575
0.7654	Intermediate Similarity	NPC131669
0.7647	Intermediate Similarity	NPC226848
0.7647	Intermediate Similarity	NPC469368
0.7639	Intermediate Similarity	NPC311736
0.7632	Intermediate Similarity	NPC315843
0.7625	Intermediate Similarity	NPC325031
0.7625	Intermediate Similarity	NPC184208
0.7625	Intermediate Similarity	NPC24417
0.7625	Intermediate Similarity	NPC8538
0.7619	Intermediate Similarity	NPC476805
0.7619	Intermediate Similarity	NPC476803
0.7606	Intermediate Similarity	NPC34883
0.7606	Intermediate Similarity	NPC300593
0.76	Intermediate Similarity	NPC129665
0.7595	Intermediate Similarity	NPC167881
0.7595	Intermediate Similarity	NPC55304
0.7595	Intermediate Similarity	NPC98557
0.7595	Intermediate Similarity	NPC226226
0.759	Intermediate Similarity	NPC329692
0.759	Intermediate Similarity	NPC311163
0.759	Intermediate Similarity	NPC116575
0.7571	Intermediate Similarity	NPC55376
0.7564	Intermediate Similarity	NPC477203
0.7561	Intermediate Similarity	NPC158756
0.7561	Intermediate Similarity	NPC82297
0.7561	Intermediate Similarity	NPC186155
0.7561	Intermediate Similarity	NPC78673
0.7561	Intermediate Similarity	NPC160517
0.7534	Intermediate Similarity	NPC259299
0.7534	Intermediate Similarity	NPC163290
0.7532	Intermediate Similarity	NPC113639
0.7531	Intermediate Similarity	NPC85772
0.7531	Intermediate Similarity	NPC89555
0.7531	Intermediate Similarity	NPC471298
0.7531	Intermediate Similarity	NPC229825
0.7531	Intermediate Similarity	NPC323251
0.7529	Intermediate Similarity	NPC474032
0.75	Intermediate Similarity	NPC282760
0.75	Intermediate Similarity	NPC474765
0.75	Intermediate Similarity	NPC313658
0.75	Intermediate Similarity	NPC316138
0.75	Intermediate Similarity	NPC312561
0.747	Intermediate Similarity	NPC470755
0.747	Intermediate Similarity	NPC11804
0.747	Intermediate Similarity	NPC471795
0.7468	Intermediate Similarity	NPC267231
0.7468	Intermediate Similarity	NPC127526
0.7468	Intermediate Similarity	NPC108816
0.7468	Intermediate Similarity	NPC93763
0.7465	Intermediate Similarity	NPC217940
0.7442	Intermediate Similarity	NPC78973
0.7439	Intermediate Similarity	NPC474193
0.7439	Intermediate Similarity	NPC471297
0.7439	Intermediate Similarity	NPC12283
0.7439	Intermediate Similarity	NPC16488
0.7439	Intermediate Similarity	NPC477667
0.7439	Intermediate Similarity	NPC44261
0.7439	Intermediate Similarity	NPC116543
0.7436	Intermediate Similarity	NPC12740
0.7436	Intermediate Similarity	NPC301525
0.7436	Intermediate Similarity	NPC235906
0.7436	Intermediate Similarity	NPC279537
0.7436	Intermediate Similarity	NPC110461
0.7432	Intermediate Similarity	NPC474823
0.7432	Intermediate Similarity	NPC276290
0.7432	Intermediate Similarity	NPC224532
0.7432	Intermediate Similarity	NPC310210
0.7429	Intermediate Similarity	NPC19241
0.7412	Intermediate Similarity	NPC474629
0.7412	Intermediate Similarity	NPC472378
0.7412	Intermediate Similarity	NPC260343
0.7407	Intermediate Similarity	NPC159148
0.7403	Intermediate Similarity	NPC107654
0.7403	Intermediate Similarity	NPC474758
0.7403	Intermediate Similarity	NPC471525
0.7403	Intermediate Similarity	NPC470686
0.7391	Intermediate Similarity	NPC181872
0.7381	Intermediate Similarity	NPC61527
0.7381	Intermediate Similarity	NPC315395
0.7381	Intermediate Similarity	NPC316426
0.7381	Intermediate Similarity	NPC150755
0.7381	Intermediate Similarity	NPC469910
0.7375	Intermediate Similarity	NPC470239
0.7375	Intermediate Similarity	NPC470244
0.7375	Intermediate Similarity	NPC100906
0.7375	Intermediate Similarity	NPC321728
0.7361	Intermediate Similarity	NPC329698
0.7349	Intermediate Similarity	NPC70424
0.7349	Intermediate Similarity	NPC243618
0.7349	Intermediate Similarity	NPC471302
0.7349	Intermediate Similarity	NPC102048
0.7349	Intermediate Similarity	NPC474865
0.7349	Intermediate Similarity	NPC31086
0.7349	Intermediate Similarity	NPC126518
0.7342	Intermediate Similarity	NPC283619
0.7342	Intermediate Similarity	NPC107668
0.7342	Intermediate Similarity	NPC473756
0.7342	Intermediate Similarity	NPC474760
0.7333	Intermediate Similarity	NPC475004
0.7333	Intermediate Similarity	NPC329989
0.7333	Intermediate Similarity	NPC74722
0.7333	Intermediate Similarity	NPC304690
0.7333	Intermediate Similarity	NPC239373
0.7326	Intermediate Similarity	NPC474396
0.7326	Intermediate Similarity	NPC50488
0.7326	Intermediate Similarity	NPC20946
0.7326	Intermediate Similarity	NPC212598
0.7326	Intermediate Similarity	NPC246028
0.7324	Intermediate Similarity	NPC225342
0.7317	Intermediate Similarity	NPC474291
0.7308	Intermediate Similarity	NPC155587
0.7297	Intermediate Similarity	NPC193029
0.7297	Intermediate Similarity	NPC473357
0.7297	Intermediate Similarity	NPC114651
0.7294	Intermediate Similarity	NPC166857
0.7294	Intermediate Similarity	NPC131329
0.7294	Intermediate Similarity	NPC199382
0.7284	Intermediate Similarity	NPC472470
0.7284	Intermediate Similarity	NPC281880
0.7284	Intermediate Similarity	NPC233332

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 NPC472254 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1847
0.2-0.3	3932
0.3-0.4	2280
0.4-0.5	724
0.5-0.6	153
0.6-0.7	55
0.7-0.8	7
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
0.7746	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7154	Phase 3
0.7439	Intermediate Similarity	NPD5362	Discontinued
0.7349	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4819	Approved
0.7284	Intermediate Similarity	NPD4821	Approved
0.7284	Intermediate Similarity	NPD4820	Approved
0.7284	Intermediate Similarity	NPD4822	Approved
0.725	Intermediate Similarity	NPD4268	Approved
0.725	Intermediate Similarity	NPD4271	Approved
0.725	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5332	Approved
0.7229	Intermediate Similarity	NPD5331	Approved
0.7195	Intermediate Similarity	NPD4790	Discontinued
0.7108	Intermediate Similarity	NPD4270	Approved
0.7108	Intermediate Similarity	NPD4269	Approved
0.7083	Intermediate Similarity	NPD368	Approved
0.7073	Intermediate Similarity	NPD4252	Approved
0.7045	Intermediate Similarity	NPD7838	Discovery
0.7045	Intermediate Similarity	NPD6698	Approved
0.7045	Intermediate Similarity	NPD5785	Approved
0.7045	Intermediate Similarity	NPD46	Approved
0.6977	Remote Similarity	NPD5786	Approved
0.6966	Remote Similarity	NPD7637	Suspended
0.6944	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4251	Approved
0.6897	Remote Similarity	NPD4250	Approved
0.6892	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5778	Approved
0.6889	Remote Similarity	NPD5779	Approved
0.6875	Remote Similarity	NPD8264	Approved
0.686	Remote Similarity	NPD5363	Approved
0.6786	Remote Similarity	NPD5369	Approved
0.6782	Remote Similarity	NPD4249	Approved
0.6778	Remote Similarity	NPD7983	Approved
0.6737	Remote Similarity	NPD5344	Discontinued
0.6706	Remote Similarity	NPD6435	Approved
0.6702	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8039	Approved
0.6632	Remote Similarity	NPD7640	Approved
0.6632	Remote Similarity	NPD7639	Approved
0.6627	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6927	Phase 3
0.6556	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6101	Approved
0.6526	Remote Similarity	NPD7638	Approved
0.6512	Remote Similarity	NPD5209	Approved
0.6506	Remote Similarity	NPD5776	Phase 2
0.6506	Remote Similarity	NPD6925	Approved
0.6489	Remote Similarity	NPD7839	Suspended
0.6479	Remote Similarity	NPD342	Phase 1
0.6477	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7514	Phase 3
0.6471	Remote Similarity	NPD5368	Approved
0.6471	Remote Similarity	NPD7332	Phase 2
0.6458	Remote Similarity	NPD6648	Approved
0.6456	Remote Similarity	NPD6922	Approved
0.6456	Remote Similarity	NPD6923	Approved
0.6437	Remote Similarity	NPD6695	Phase 3
0.6429	Remote Similarity	NPD7145	Approved
0.6413	Remote Similarity	NPD6411	Approved
0.641	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6902	Approved
0.6383	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7144	Approved
0.6375	Remote Similarity	NPD7143	Approved
0.6374	Remote Similarity	NPD5370	Suspended
0.6374	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4265	Approved
0.6353	Remote Similarity	NPD6929	Approved
0.6341	Remote Similarity	NPD6926	Approved
0.6341	Remote Similarity	NPD6924	Approved
0.6322	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7150	Approved
0.6296	Remote Similarity	NPD7152	Approved
0.6296	Remote Similarity	NPD7151	Approved
0.6279	Remote Similarity	NPD6931	Approved
0.6279	Remote Similarity	NPD6930	Phase 2
0.6237	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD3197	Phase 1
0.6214	Remote Similarity	NPD6371	Approved
0.6207	Remote Similarity	NPD6898	Phase 1
0.619	Remote Similarity	NPD6933	Approved
0.6184	Remote Similarity	NPD4194	Approved
0.6184	Remote Similarity	NPD4191	Approved
0.6184	Remote Similarity	NPD4192	Approved
0.6184	Remote Similarity	NPD4193	Approved
0.617	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD7524	Approved
0.6154	Remote Similarity	NPD7750	Discontinued
0.6118	Remote Similarity	NPD6932	Approved
0.6111	Remote Similarity	NPD1694	Approved
0.6078	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7339	Approved
0.6071	Remote Similarity	NPD6942	Approved
0.6067	Remote Similarity	NPD6110	Phase 1
0.6044	Remote Similarity	NPD6422	Discontinued
0.6024	Remote Similarity	NPD4732	Discontinued
0.6022	Remote Similarity	NPD1695	Approved
0.6019	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6109	Phase 1
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4786	Approved
0.5977	Remote Similarity	NPD6683	Phase 2
0.5977	Remote Similarity	NPD7645	Phase 2
0.5955	Remote Similarity	NPD3667	Approved
0.5946	Remote Similarity	NPD4219	Approved
0.5943	Remote Similarity	NPD6053	Discontinued
0.5941	Remote Similarity	NPD6647	Phase 2
0.5938	Remote Similarity	NPD7748	Approved
0.5934	Remote Similarity	NPD6893	Approved
0.593	Remote Similarity	NPD4756	Discovery
0.5909	Remote Similarity	NPD7509	Discontinued
0.5895	Remote Similarity	NPD7515	Phase 2
0.5895	Remote Similarity	NPD7087	Discontinued
0.589	Remote Similarity	NPD4266	Approved
0.589	Remote Similarity	NPD3196	Approved
0.589	Remote Similarity	NPD3194	Approved
0.589	Remote Similarity	NPD3195	Phase 2
0.5875	Remote Similarity	NPD7331	Phase 2
0.5872	Remote Similarity	NPD7115	Discovery
0.587	Remote Similarity	NPD7334	Approved
0.587	Remote Similarity	NPD6684	Approved
0.587	Remote Similarity	NPD5330	Approved
0.587	Remote Similarity	NPD7146	Approved
0.587	Remote Similarity	NPD6409	Approved
0.587	Remote Similarity	NPD7521	Approved
0.581	Remote Similarity	NPD6413	Approved
0.5806	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD7902	Approved
0.5758	Remote Similarity	NPD6083	Phase 2
0.5753	Remote Similarity	NPD3172	Approved
0.5745	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6903	Approved
0.573	Remote Similarity	NPD7525	Registered
0.573	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD5343	Approved
0.5714	Remote Similarity	NPD3198	Approved
0.5682	Remote Similarity	NPD3732	Approved
0.5673	Remote Similarity	NPD6640	Phase 3
0.567	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8517	Approved
0.5664	Remote Similarity	NPD8513	Phase 3
0.5664	Remote Similarity	NPD8516	Approved
0.5664	Remote Similarity	NPD8515	Approved
0.5652	Remote Similarity	NPD39	Approved
0.5652	Remote Similarity	NPD3133	Approved
0.5652	Remote Similarity	NPD3665	Phase 1
0.5652	Remote Similarity	NPD3666	Approved
0.5634	Remote Similarity	NPD4220	Pre-registration
0.5634	Remote Similarity	NPD3173	Approved
0.5631	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7136	Phase 2
0.5607	Remote Similarity	NPD6420	Discontinued

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