NPASS Compound

Structure

CID108164 OpenBabel06191715452D 25 28 0 0 1 0 0 0 0 0999 V2000 3.9332 -1.3060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3853 0.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5765 1.5259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0007 -2.5513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0311 -1.5473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4011 -0.8084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9589 -2.2097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1501 -2.6766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -1.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5924 -1.2757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7677 -0.8088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1501 0.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5765 0.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9589 -1.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7677 0.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1501 -0.8088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9589 0.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3413 -2.2097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8087 -0.4673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4674 -1.7424 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3413 -1.2758 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9589 1.5259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7109 -0.2260 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 5 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 5 24 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 1 0 0 0 19 22 1 0 0 0 0 20 22 1 1 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 4 1 1 0 0 0 22 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.24
Volume:	373.304
LogP:	5.042
LogD:	4.202
LogS:	-5.061
# Rotatable Bonds:	3
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.848
Synthetic Accessibility Score:	5.031
Fsp3:	0.727
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:	-4.725
MDCK Permeability:	2.172471613448579e-05
Pgp-inhibitor:	0.768
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.385

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.334
Plasma Protein Binding (PPB):	96.29788970947266%
Volume Distribution (VD):	1.924
Pgp-substrate:	2.408902645111084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.21
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.297
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.351
CYP2C9-substrate:	0.302
CYP2D6-inhibitor:	0.328
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.742
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	5.439
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.154
AMES Toxicity:	0.377
Rat Oral Acute Toxicity:	0.392
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.934
Carcinogencity:	0.675
Eye Corrosion:	0.003
Eye Irritation:	0.769
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC108164

Natural Product ID:	NPC108164
*Common Name:**	KZYXNKRMNALLBY-CBPXPLCBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KZYXNKRMNALLBY-CBPXPLCBSA-N
Standard InCHI:	InChI=1S/C22H32O3/c1-5-24-20-22-10-6-9-21(4,13-25-20)19(22)8-7-15-11-16(14(2)3)18(23)12-17(15)22/h11-12,14,19-20,23H,5-10,13H2,1-4H3/t19-,20+,21+,22-/m0/s1
SMILES:	CCO[C@@H]1OC[C@@]2([C@H]3[C@]1(CCC2)c1cc(O)c(cc1CC3)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651071
PubChem CID:	50900595
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
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[520503]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[520503]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[520503]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[520503]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[520503]

☑ 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 NPC108164 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	347
0.1-0.2	1553
0.2-0.3	3168
0.3-0.4	7666
0.4-0.5	10953
0.5-0.6	10205
0.6-0.7	7517
0.7-0.8	1210
0.8-0.85	58
0.85-0.9	14
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC100414
0.9917	High Similarity	NPC43000
0.9752	High Similarity	NPC325294
0.9752	High Similarity	NPC321822
0.9444	High Similarity	NPC321086
0.9062	High Similarity	NPC473047
0.8926	High Similarity	NPC304510
0.8926	High Similarity	NPC172219
0.8852	High Similarity	NPC471671
0.8837	High Similarity	NPC472793
0.8828	High Similarity	NPC223912
0.878	High Similarity	NPC469644
0.876	High Similarity	NPC192948
0.876	High Similarity	NPC35797
0.874	High Similarity	NPC124030
0.8689	High Similarity	NPC308311
0.8689	High Similarity	NPC477137
0.8689	High Similarity	NPC471668
0.8689	High Similarity	NPC38893
0.8686	High Similarity	NPC100242
0.8636	High Similarity	NPC49742
0.8605	High Similarity	NPC186889
0.8605	High Similarity	NPC471077
0.8583	High Similarity	NPC260323
0.8583	High Similarity	NPC176279
0.8548	High Similarity	NPC469609
0.8548	High Similarity	NPC154030
0.8537	High Similarity	NPC219112
0.8525	High Similarity	NPC268160
0.8504	High Similarity	NPC478058
0.848	Intermediate Similarity	NPC93071
0.848	Intermediate Similarity	NPC126002
0.8468	Intermediate Similarity	NPC477136
0.8455	Intermediate Similarity	NPC147179
0.8413	Intermediate Similarity	NPC135467
0.8413	Intermediate Similarity	NPC260832
0.8409	Intermediate Similarity	NPC99795
0.8394	Intermediate Similarity	NPC164743
0.8387	Intermediate Similarity	NPC469663
0.8387	Intermediate Similarity	NPC92
0.8387	Intermediate Similarity	NPC308828
0.8374	Intermediate Similarity	NPC195922
0.8361	Intermediate Similarity	NPC250323
0.8359	Intermediate Similarity	NPC71094
0.8347	Intermediate Similarity	NPC141782
0.8333	Intermediate Similarity	NPC472792
0.8333	Intermediate Similarity	NPC476452
0.8333	Intermediate Similarity	NPC472791
0.8322	Intermediate Similarity	NPC183380
0.8284	Intermediate Similarity	NPC59239
0.8279	Intermediate Similarity	NPC151537
0.8254	Intermediate Similarity	NPC206
0.825	Intermediate Similarity	NPC151477
0.824	Intermediate Similarity	NPC141001
0.8217	Intermediate Similarity	NPC11250
0.8217	Intermediate Similarity	NPC471794
0.8211	Intermediate Similarity	NPC228425
0.8211	Intermediate Similarity	NPC46940
0.8209	Intermediate Similarity	NPC78575
0.8209	Intermediate Similarity	NPC312341
0.8203	Intermediate Similarity	NPC328504
0.8197	Intermediate Similarity	NPC132720
0.8197	Intermediate Similarity	NPC13482
0.8156	Intermediate Similarity	NPC96447
0.8154	Intermediate Similarity	NPC471187
0.8151	Intermediate Similarity	NPC106669
0.8151	Intermediate Similarity	NPC475227
0.8151	Intermediate Similarity	NPC200645
0.8148	Intermediate Similarity	NPC165612
0.8145	Intermediate Similarity	NPC715
0.814	Intermediate Similarity	NPC162935
0.814	Intermediate Similarity	NPC249340
0.8134	Intermediate Similarity	NPC196193
0.8134	Intermediate Similarity	NPC473048
0.813	Intermediate Similarity	NPC95716
0.8129	Intermediate Similarity	NPC472794
0.8129	Intermediate Similarity	NPC473049
0.8125	Intermediate Similarity	NPC295573
0.8125	Intermediate Similarity	NPC470208
0.8092	Intermediate Similarity	NPC181334
0.8085	Intermediate Similarity	NPC204644
0.8083	Intermediate Similarity	NPC117115
0.808	Intermediate Similarity	NPC471534
0.8077	Intermediate Similarity	NPC121168
0.806	Intermediate Similarity	NPC25729
0.806	Intermediate Similarity	NPC474494
0.8047	Intermediate Similarity	NPC151197
0.8045	Intermediate Similarity	NPC476536
0.8042	Intermediate Similarity	NPC471608
0.8033	Intermediate Similarity	NPC11554
0.8031	Intermediate Similarity	NPC16030
0.803	Intermediate Similarity	NPC137750
0.803	Intermediate Similarity	NPC87985
0.8028	Intermediate Similarity	NPC164183
0.8028	Intermediate Similarity	NPC133251
0.8017	Intermediate Similarity	NPC21594
0.8016	Intermediate Similarity	NPC469719
0.8014	Intermediate Similarity	NPC77310
0.8	Intermediate Similarity	NPC249425
0.8	Intermediate Similarity	NPC263753
0.8	Intermediate Similarity	NPC253627
0.7984	Intermediate Similarity	NPC478121
0.7984	Intermediate Similarity	NPC469912
0.7984	Intermediate Similarity	NPC68339
0.7984	Intermediate Similarity	NPC3239
0.7984	Intermediate Similarity	NPC282255
0.7984	Intermediate Similarity	NPC77772
0.7984	Intermediate Similarity	NPC322753
0.7972	Intermediate Similarity	NPC272619
0.7972	Intermediate Similarity	NPC286245
0.7971	Intermediate Similarity	NPC279463
0.7971	Intermediate Similarity	NPC137580
0.7969	Intermediate Similarity	NPC48342
0.7969	Intermediate Similarity	NPC164649
0.7967	Intermediate Similarity	NPC58865
0.7956	Intermediate Similarity	NPC227719
0.7956	Intermediate Similarity	NPC177712
0.7956	Intermediate Similarity	NPC24913
0.7955	Intermediate Similarity	NPC10154
0.7955	Intermediate Similarity	NPC265413
0.7953	Intermediate Similarity	NPC474358
0.7953	Intermediate Similarity	NPC474387
0.7953	Intermediate Similarity	NPC247858
0.7953	Intermediate Similarity	NPC154511
0.7953	Intermediate Similarity	NPC137496
0.7953	Intermediate Similarity	NPC257540
0.7945	Intermediate Similarity	NPC225815
0.7945	Intermediate Similarity	NPC214326
0.7945	Intermediate Similarity	NPC9933
0.7945	Intermediate Similarity	NPC145979
0.7945	Intermediate Similarity	NPC469706
0.7945	Intermediate Similarity	NPC469707
0.7945	Intermediate Similarity	NPC182368
0.7945	Intermediate Similarity	NPC218041
0.7945	Intermediate Similarity	NPC185955
0.7945	Intermediate Similarity	NPC260781
0.7943	Intermediate Similarity	NPC3218
0.7939	Intermediate Similarity	NPC152946
0.7934	Intermediate Similarity	NPC99557
0.7934	Intermediate Similarity	NPC219286
0.7931	Intermediate Similarity	NPC179809
0.7923	Intermediate Similarity	NPC259703
0.7923	Intermediate Similarity	NPC241001
0.7923	Intermediate Similarity	NPC32322
0.792	Intermediate Similarity	NPC62867
0.792	Intermediate Similarity	NPC177962
0.7914	Intermediate Similarity	NPC68292
0.7902	Intermediate Similarity	NPC471065
0.7902	Intermediate Similarity	NPC253015
0.7895	Intermediate Similarity	NPC293801
0.7895	Intermediate Similarity	NPC4286
0.7895	Intermediate Similarity	NPC76119
0.7891	Intermediate Similarity	NPC299180
0.7887	Intermediate Similarity	NPC272907
0.7887	Intermediate Similarity	NPC186033
0.7887	Intermediate Similarity	NPC2681
0.7886	Intermediate Similarity	NPC149455
0.7886	Intermediate Similarity	NPC64642
0.7886	Intermediate Similarity	NPC472982
0.7883	Intermediate Similarity	NPC27578
0.7883	Intermediate Similarity	NPC85595
0.7883	Intermediate Similarity	NPC289624
0.7879	Intermediate Similarity	NPC198014
0.7877	Intermediate Similarity	NPC44452
0.7877	Intermediate Similarity	NPC181452
0.7877	Intermediate Similarity	NPC220006
0.7874	Intermediate Similarity	NPC84999
0.7874	Intermediate Similarity	NPC246760
0.7868	Intermediate Similarity	NPC325003
0.7863	Intermediate Similarity	NPC469686
0.7863	Intermediate Similarity	NPC142198
0.7863	Intermediate Similarity	NPC474115
0.7863	Intermediate Similarity	NPC154696
0.7863	Intermediate Similarity	NPC77569
0.7862	Intermediate Similarity	NPC470330
0.7857	Intermediate Similarity	NPC317869
0.7857	Intermediate Similarity	NPC322239
0.7852	Intermediate Similarity	NPC201069
0.784	Intermediate Similarity	NPC470770
0.784	Intermediate Similarity	NPC266937
0.7836	Intermediate Similarity	NPC470724
0.7826	Intermediate Similarity	NPC211352
0.7823	Intermediate Similarity	NPC314187
0.7823	Intermediate Similarity	NPC247219
0.781	Intermediate Similarity	NPC476847
0.781	Intermediate Similarity	NPC153019
0.7808	Intermediate Similarity	NPC130959
0.7808	Intermediate Similarity	NPC159697
0.7808	Intermediate Similarity	NPC474795
0.7808	Intermediate Similarity	NPC95990
0.7808	Intermediate Similarity	NPC474940
0.7808	Intermediate Similarity	NPC303013
0.7808	Intermediate Similarity	NPC291326
0.7808	Intermediate Similarity	NPC474856
0.7808	Intermediate Similarity	NPC290902
0.7808	Intermediate Similarity	NPC474834
0.7808	Intermediate Similarity	NPC117788
0.7803	Intermediate Similarity	NPC297057
0.7803	Intermediate Similarity	NPC176208
0.78	Intermediate Similarity	NPC474501

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 NPC108164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	897
0.2-0.3	1500
0.3-0.4	2977
0.4-0.5	1971
0.5-0.6	1107
0.6-0.7	349
0.7-0.8	42
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
0.7969	Intermediate Similarity	NPD3091	Approved
0.7943	Intermediate Similarity	NPD6674	Discontinued
0.791	Intermediate Similarity	NPD5736	Approved
0.7863	Intermediate Similarity	NPD3092	Approved
0.7778	Intermediate Similarity	NPD7635	Approved
0.7737	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD6663	Approved
0.7661	Intermediate Similarity	NPD2342	Discontinued
0.763	Intermediate Similarity	NPD3094	Phase 2
0.7609	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3019	Approved
0.7576	Intermediate Similarity	NPD4059	Approved
0.7576	Intermediate Similarity	NPD3095	Discontinued
0.7574	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6696	Suspended
0.754	Intermediate Similarity	NPD4750	Phase 3
0.7536	Intermediate Similarity	NPD4625	Phase 3
0.7464	Intermediate Similarity	NPD4908	Phase 1
0.7444	Intermediate Similarity	NPD2932	Approved
0.7417	Intermediate Similarity	NPD1809	Phase 2
0.7394	Intermediate Similarity	NPD4097	Suspended
0.7391	Intermediate Similarity	NPD2861	Phase 2
0.7377	Intermediate Similarity	NPD3020	Approved
0.7355	Intermediate Similarity	NPD288	Approved
0.7353	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4749	Approved
0.7353	Intermediate Similarity	NPD5327	Phase 3
0.7324	Intermediate Similarity	NPD5735	Approved
0.7315	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4626	Approved
0.731	Intermediate Similarity	NPD7266	Discontinued
0.7292	Intermediate Similarity	NPD4108	Discontinued
0.7287	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD844	Approved
0.7254	Intermediate Similarity	NPD4060	Phase 1
0.7254	Intermediate Similarity	NPD3620	Phase 2
0.7254	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4140	Approved
0.7241	Intermediate Similarity	NPD6099	Approved
0.7241	Intermediate Similarity	NPD6100	Approved
0.7239	Intermediate Similarity	NPD5691	Approved
0.7214	Intermediate Similarity	NPD2605	Approved
0.7214	Intermediate Similarity	NPD2606	Approved
0.7211	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1610	Phase 2
0.7194	Intermediate Similarity	NPD4624	Approved
0.719	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2286	Discontinued
0.7185	Intermediate Similarity	NPD5125	Phase 3
0.7185	Intermediate Similarity	NPD5126	Approved
0.7177	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5155	Approved
0.7163	Intermediate Similarity	NPD5156	Approved
0.7162	Intermediate Similarity	NPD8166	Discontinued
0.7153	Intermediate Similarity	NPD6353	Approved
0.7143	Intermediate Similarity	NPD7340	Approved
0.7132	Intermediate Similarity	NPD3021	Approved
0.7132	Intermediate Similarity	NPD3022	Approved
0.7131	Intermediate Similarity	NPD2859	Approved
0.7131	Intermediate Similarity	NPD2860	Approved
0.7124	Intermediate Similarity	NPD7458	Discontinued
0.7111	Intermediate Similarity	NPD4093	Discontinued
0.7107	Intermediate Similarity	NPD845	Approved
0.7099	Intermediate Similarity	NPD7228	Approved
0.7092	Intermediate Similarity	NPD3594	Approved
0.7092	Intermediate Similarity	NPD3595	Approved
0.708	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3705	Approved
0.708	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4726	Approved
0.7075	Intermediate Similarity	NPD4725	Approved
0.7075	Intermediate Similarity	NPD4721	Approved
0.7059	Intermediate Similarity	NPD1751	Approved
0.7055	Intermediate Similarity	NPD7743	Approved
0.7055	Intermediate Similarity	NPD7742	Approved
0.705	Intermediate Similarity	NPD8651	Approved
0.7049	Intermediate Similarity	NPD2933	Approved
0.7049	Intermediate Similarity	NPD2934	Approved
0.7047	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7003	Approved
0.7037	Intermediate Similarity	NPD7741	Discontinued
0.7021	Intermediate Similarity	NPD3636	Approved
0.7021	Intermediate Similarity	NPD3637	Approved
0.7021	Intermediate Similarity	NPD3635	Approved
0.702	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7041	Phase 2
0.7015	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5408	Approved
0.7007	Intermediate Similarity	NPD3026	Approved
0.7007	Intermediate Similarity	NPD5404	Approved
0.7007	Intermediate Similarity	NPD5406	Approved
0.7007	Intermediate Similarity	NPD3023	Approved
0.7007	Intermediate Similarity	NPD5405	Approved
0.6987	Remote Similarity	NPD37	Approved
0.6986	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3025	Approved
0.6985	Remote Similarity	NPD3024	Approved
0.6984	Remote Similarity	NPD846	Approved
0.6984	Remote Similarity	NPD940	Approved
0.6981	Remote Similarity	NPD6234	Discontinued
0.6974	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4965	Approved
0.6962	Remote Similarity	NPD4967	Phase 2
0.6962	Remote Similarity	NPD4966	Approved
0.6959	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1201	Approved
0.694	Remote Similarity	NPD6671	Approved
0.6929	Remote Similarity	NPD1283	Approved
0.6917	Remote Similarity	NPD1398	Phase 1
0.6917	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7294	Phase 1
0.6846	Remote Similarity	NPD5763	Approved
0.6846	Remote Similarity	NPD5762	Approved
0.6845	Remote Similarity	NPD8313	Approved
0.6845	Remote Similarity	NPD8312	Approved
0.6835	Remote Similarity	NPD8455	Phase 2
0.6835	Remote Similarity	NPD1091	Approved
0.6831	Remote Similarity	NPD2194	Approved
0.6831	Remote Similarity	NPD2195	Approved
0.6828	Remote Similarity	NPD8032	Phase 2
0.6824	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1778	Approved
0.6812	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4589	Approved
0.68	Remote Similarity	NPD7037	Approved
0.6797	Remote Similarity	NPD7390	Discontinued
0.6797	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1548	Phase 1
0.6776	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4727	Phase 1
0.6772	Remote Similarity	NPD1242	Phase 1
0.6761	Remote Similarity	NPD1470	Approved
0.6759	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7097	Phase 1
0.6757	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3638	Discontinued
0.6742	Remote Similarity	NPD1792	Phase 2
0.6741	Remote Similarity	NPD497	Approved
0.6739	Remote Similarity	NPD1651	Approved
0.6739	Remote Similarity	NPD1357	Approved
0.6726	Remote Similarity	NPD7240	Approved
0.6714	Remote Similarity	NPD1281	Approved
0.6713	Remote Similarity	NPD6584	Phase 3
0.6712	Remote Similarity	NPD6407	Approved
0.6712	Remote Similarity	NPD6405	Approved
0.671	Remote Similarity	NPD6273	Approved
0.6691	Remote Similarity	NPD7157	Approved
0.6691	Remote Similarity	NPD709	Approved
0.669	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7095	Approved
0.6688	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD498	Approved
0.6667	Remote Similarity	NPD1613	Approved
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD496	Approved
0.6667	Remote Similarity	NPD2228	Approved
0.6667	Remote Similarity	NPD7330	Discontinued
0.6667	Remote Similarity	NPD3109	Approved
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD495	Approved
0.6667	Remote Similarity	NPD5303	Approved
0.6667	Remote Similarity	NPD2234	Approved
0.6667	Remote Similarity	NPD3110	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2229	Approved
0.6667	Remote Similarity	NPD5304	Approved
0.6646	Remote Similarity	NPD3051	Approved
0.6644	Remote Similarity	NPD3764	Approved
0.6625	Remote Similarity	NPD7819	Suspended
0.6623	Remote Similarity	NPD6666	Approved
0.6623	Remote Similarity	NPD6667	Approved
0.6622	Remote Similarity	NPD5124	Phase 1
0.6622	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3657	Discovery
0.6621	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4659	Approved
0.6606	Remote Similarity	NPD2970	Approved
0.6606	Remote Similarity	NPD2969	Approved
0.6603	Remote Similarity	NPD6090	Discontinued
0.66	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1611	Approved
0.6594	Remote Similarity	NPD7644	Approved
0.6593	Remote Similarity	NPD1138	Approved
0.6585	Remote Similarity	NPD7199	Phase 2
0.6584	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2420	Approved
0.6581	Remote Similarity	NPD2421	Approved
0.6581	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2157	Approved
0.6577	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3027	Phase 3
0.6569	Remote Similarity	NPD6387	Discontinued
0.6569	Remote Similarity	NPD4198	Discontinued
0.6566	Remote Similarity	NPD27	Approved
0.6566	Remote Similarity	NPD2489	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