NPASS Compound

Structure

CID321822 OpenBabel06191716162D 23 26 0 0 1 0 0 0 0 0999 V2000 4.5300 0.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6945 1.5763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0007 -2.6356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4473 -0.8351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0236 -2.2826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1881 -2.7650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4476 -1.7999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6119 -1.3178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8590 -0.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1881 0.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6945 0.6116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0236 -1.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8590 0.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1881 -0.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0236 0.6115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3526 -2.2826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8354 -0.4827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4828 -1.7999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3526 -1.3179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0236 1.5763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7674 -0.2334 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 12 1 0 0 0 0 2 12 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 3 1 1 0 0 0 20 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	338.712
LogP:	3.985
LogD:	3.511
LogS:	-4.259
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.827
Synthetic Accessibility Score:	4.929
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.653
MDCK Permeability:	2.133164343831595e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.102
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.895

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.548
Plasma Protein Binding (PPB):	95.58177185058594%
Volume Distribution (VD):	2.396
Pgp-substrate:	3.4232873916625977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.172
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.392
CYP2D6-inhibitor:	0.381
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.67
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	9.993
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.808
Rat Oral Acute Toxicity:	0.745
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.912
Carcinogencity:	0.948
Eye Corrosion:	0.003
Eye Irritation:	0.616
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC321822

Natural Product ID:	NPC321822
*Common Name:**	QVGFDWPRYXYPGU-NMLBUPMWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QVGFDWPRYXYPGU-NMLBUPMWSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12(2)14-9-13-5-6-17-19(3)7-4-8-20(17,18(22)23-11-19)15(13)10-16(14)21/h9-10,12,17-18,21-22H,4-8,11H2,1-3H3/t17-,18+,19+,20-/m0/s1
SMILES:	CC(C)C1=C(C=C2C(=C1)CCC3C24CCCC3(COC4O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651067
PubChem CID:	53326128
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[498314]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[498314]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[498314]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[498314]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[498314]

☑ 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 NPC321822 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	333
0.1-0.2	1534
0.2-0.3	3204
0.3-0.4	7714
0.4-0.5	10936
0.5-0.6	9740
0.6-0.7	7879
0.7-0.8	1272
0.8-0.85	53
0.85-0.9	26
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC325294
0.9833	High Similarity	NPC43000
0.9833	High Similarity	NPC100414
0.9752	High Similarity	NPC108164
0.9365	High Similarity	NPC321086
0.916	High Similarity	NPC304510
0.916	High Similarity	NPC172219
0.9083	High Similarity	NPC471671
0.9008	High Similarity	NPC469644
0.8992	High Similarity	NPC192948
0.8992	High Similarity	NPC35797
0.8917	High Similarity	NPC477137
0.8917	High Similarity	NPC38893
0.8917	High Similarity	NPC308311
0.8906	High Similarity	NPC472793
0.8898	High Similarity	NPC223912
0.8837	High Similarity	NPC473047
0.8819	High Similarity	NPC186889
0.881	High Similarity	NPC124030
0.877	High Similarity	NPC154030
0.877	High Similarity	NPC469609
0.876	High Similarity	NPC219112
0.875	High Similarity	NPC268160
0.8702	High Similarity	NPC49742
0.8689	High Similarity	NPC477136
0.8678	High Similarity	NPC147179
0.8672	High Similarity	NPC471077
0.8655	High Similarity	NPC176279
0.8655	High Similarity	NPC260323
0.8613	High Similarity	NPC100242
0.8607	High Similarity	NPC469663
0.8607	High Similarity	NPC308828
0.8607	High Similarity	NPC92
0.8607	High Similarity	NPC471668
0.8485	Intermediate Similarity	NPC59239
0.8473	Intermediate Similarity	NPC99795
0.8443	Intermediate Similarity	NPC195922
0.843	Intermediate Similarity	NPC250323
0.8425	Intermediate Similarity	NPC478058
0.8425	Intermediate Similarity	NPC71094
0.8425	Intermediate Similarity	NPC471794
0.8417	Intermediate Similarity	NPC132720
0.8417	Intermediate Similarity	NPC141782
0.8413	Intermediate Similarity	NPC328504
0.84	Intermediate Similarity	NPC126002
0.84	Intermediate Similarity	NPC93071
0.8359	Intermediate Similarity	NPC471187
0.8347	Intermediate Similarity	NPC151537
0.8333	Intermediate Similarity	NPC196193
0.8333	Intermediate Similarity	NPC135467
0.8333	Intermediate Similarity	NPC260832
0.8321	Intermediate Similarity	NPC164743
0.8319	Intermediate Similarity	NPC151477
0.8295	Intermediate Similarity	NPC181334
0.8281	Intermediate Similarity	NPC11250
0.8279	Intermediate Similarity	NPC228425
0.8279	Intermediate Similarity	NPC46940
0.8271	Intermediate Similarity	NPC312341
0.8271	Intermediate Similarity	NPC78575
0.8264	Intermediate Similarity	NPC13482
0.8252	Intermediate Similarity	NPC183380
0.8231	Intermediate Similarity	NPC87985
0.8211	Intermediate Similarity	NPC715
0.8209	Intermediate Similarity	NPC165612
0.8203	Intermediate Similarity	NPC249340
0.8203	Intermediate Similarity	NPC162935
0.8197	Intermediate Similarity	NPC95716
0.8188	Intermediate Similarity	NPC473049
0.8188	Intermediate Similarity	NPC472794
0.8175	Intermediate Similarity	NPC206
0.8175	Intermediate Similarity	NPC164649
0.8175	Intermediate Similarity	NPC48342
0.816	Intermediate Similarity	NPC141001
0.8151	Intermediate Similarity	NPC117115
0.8145	Intermediate Similarity	NPC471534
0.814	Intermediate Similarity	NPC152946
0.814	Intermediate Similarity	NPC121168
0.8138	Intermediate Similarity	NPC476452
0.8129	Intermediate Similarity	NPC472791
0.8129	Intermediate Similarity	NPC472792
0.811	Intermediate Similarity	NPC151197
0.8106	Intermediate Similarity	NPC476536
0.8099	Intermediate Similarity	NPC11554
0.8099	Intermediate Similarity	NPC472982
0.8099	Intermediate Similarity	NPC471608
0.8099	Intermediate Similarity	NPC64642
0.8099	Intermediate Similarity	NPC149455
0.8095	Intermediate Similarity	NPC16030
0.8092	Intermediate Similarity	NPC4286
0.8092	Intermediate Similarity	NPC76119
0.8092	Intermediate Similarity	NPC137750
0.8083	Intermediate Similarity	NPC21594
0.8082	Intermediate Similarity	NPC475227
0.8082	Intermediate Similarity	NPC200645
0.8082	Intermediate Similarity	NPC106669
0.808	Intermediate Similarity	NPC469719
0.8077	Intermediate Similarity	NPC198014
0.8071	Intermediate Similarity	NPC2681
0.8071	Intermediate Similarity	NPC272907
0.8062	Intermediate Similarity	NPC253627
0.8062	Intermediate Similarity	NPC77569
0.8062	Intermediate Similarity	NPC142198
0.806	Intermediate Similarity	NPC249425
0.806	Intermediate Similarity	NPC325003
0.8049	Intermediate Similarity	NPC322753
0.8049	Intermediate Similarity	NPC77772
0.8047	Intermediate Similarity	NPC478121
0.8047	Intermediate Similarity	NPC3239
0.8047	Intermediate Similarity	NPC68339
0.8047	Intermediate Similarity	NPC282255
0.8033	Intermediate Similarity	NPC58865
0.803	Intermediate Similarity	NPC470724
0.8016	Intermediate Similarity	NPC257540
0.8016	Intermediate Similarity	NPC154511
0.8016	Intermediate Similarity	NPC137496
0.8016	Intermediate Similarity	NPC247858
0.8016	Intermediate Similarity	NPC474387
0.8016	Intermediate Similarity	NPC474358
0.8015	Intermediate Similarity	NPC227719
0.8014	Intermediate Similarity	NPC204644
0.8	Intermediate Similarity	NPC3218
0.7985	Intermediate Similarity	NPC25729
0.7985	Intermediate Similarity	NPC474494
0.7984	Intermediate Similarity	NPC241001
0.7984	Intermediate Similarity	NPC259703
0.7984	Intermediate Similarity	NPC32322
0.7973	Intermediate Similarity	NPC474501
0.7971	Intermediate Similarity	NPC68292
0.7958	Intermediate Similarity	NPC164183
0.7958	Intermediate Similarity	NPC133251
0.7958	Intermediate Similarity	NPC96447
0.7955	Intermediate Similarity	NPC470726
0.7955	Intermediate Similarity	NPC293801
0.7953	Intermediate Similarity	NPC299180
0.7945	Intermediate Similarity	NPC77310
0.7941	Intermediate Similarity	NPC27578
0.7941	Intermediate Similarity	NPC289624
0.7941	Intermediate Similarity	NPC85595
0.7937	Intermediate Similarity	NPC246760
0.7937	Intermediate Similarity	NPC84999
0.7931	Intermediate Similarity	NPC295573
0.7931	Intermediate Similarity	NPC470208
0.7926	Intermediate Similarity	NPC473048
0.7923	Intermediate Similarity	NPC154696
0.7923	Intermediate Similarity	NPC474115
0.7923	Intermediate Similarity	NPC475166
0.792	Intermediate Similarity	NPC322239
0.792	Intermediate Similarity	NPC317869
0.792	Intermediate Similarity	NPC263753
0.7917	Intermediate Similarity	NPC474991
0.7903	Intermediate Similarity	NPC470770
0.7903	Intermediate Similarity	NPC469912
0.7903	Intermediate Similarity	NPC266937
0.7902	Intermediate Similarity	NPC272619
0.7902	Intermediate Similarity	NPC286245
0.7899	Intermediate Similarity	NPC279463
0.7886	Intermediate Similarity	NPC314187
0.7883	Intermediate Similarity	NPC24913
0.7883	Intermediate Similarity	NPC177712
0.7883	Intermediate Similarity	NPC211352
0.7879	Intermediate Similarity	NPC265413
0.7879	Intermediate Similarity	NPC10154
0.7877	Intermediate Similarity	NPC469706
0.7877	Intermediate Similarity	NPC182368
0.7877	Intermediate Similarity	NPC145979
0.7877	Intermediate Similarity	NPC218041
0.7877	Intermediate Similarity	NPC469707
0.7877	Intermediate Similarity	NPC214326
0.7877	Intermediate Similarity	NPC260781
0.7877	Intermediate Similarity	NPC225815
0.7877	Intermediate Similarity	NPC9933
0.7877	Intermediate Similarity	NPC185955
0.7869	Intermediate Similarity	NPC27252
0.7869	Intermediate Similarity	NPC472979
0.7868	Intermediate Similarity	NPC476847
0.7868	Intermediate Similarity	NPC471851
0.7868	Intermediate Similarity	NPC153019
0.7863	Intermediate Similarity	NPC176208
0.7863	Intermediate Similarity	NPC321402
0.7862	Intermediate Similarity	NPC179809
0.7857	Intermediate Similarity	NPC107240
0.7857	Intermediate Similarity	NPC249270
0.7852	Intermediate Similarity	NPC470747
0.7851	Intermediate Similarity	NPC99557
0.7851	Intermediate Similarity	NPC219286
0.7851	Intermediate Similarity	NPC243601
0.784	Intermediate Similarity	NPC62867
0.784	Intermediate Similarity	NPC473521
0.784	Intermediate Similarity	NPC302371
0.784	Intermediate Similarity	NPC471179
0.784	Intermediate Similarity	NPC177962
0.7832	Intermediate Similarity	NPC253015
0.7832	Intermediate Similarity	NPC471065
0.7829	Intermediate Similarity	NPC176893
0.7829	Intermediate Similarity	NPC42657
0.7826	Intermediate Similarity	NPC213122
0.7826	Intermediate Similarity	NPC473107
0.7823	Intermediate Similarity	NPC224870
0.782	Intermediate Similarity	NPC476653
0.782	Intermediate Similarity	NPC105031

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 NPC321822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	902
0.2-0.3	1482
0.3-0.4	2956
0.4-0.5	1961
0.5-0.6	1127
0.6-0.7	376
0.7-0.8	51
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
0.8175	Intermediate Similarity	NPD3091	Approved
0.8062	Intermediate Similarity	NPD3092	Approved
0.7872	Intermediate Similarity	NPD6674	Discontinued
0.7836	Intermediate Similarity	NPD5736	Approved
0.782	Intermediate Similarity	NPD3094	Phase 2
0.7794	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD3095	Discontinued
0.7724	Intermediate Similarity	NPD2342	Discontinued
0.7698	Intermediate Similarity	NPD7635	Approved
0.7664	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4059	Approved
0.7634	Intermediate Similarity	NPD3019	Approved
0.763	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6663	Approved
0.76	Intermediate Similarity	NPD4750	Phase 3
0.7591	Intermediate Similarity	NPD4625	Phase 3
0.7518	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD2932	Approved
0.7481	Intermediate Similarity	NPD6696	Suspended
0.7479	Intermediate Similarity	NPD1809	Phase 2
0.7447	Intermediate Similarity	NPD4097	Suspended
0.7445	Intermediate Similarity	NPD2861	Phase 2
0.7438	Intermediate Similarity	NPD3020	Approved
0.7429	Intermediate Similarity	NPD4140	Approved
0.7429	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3620	Phase 2
0.7417	Intermediate Similarity	NPD288	Approved
0.7407	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4749	Approved
0.7379	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5735	Approved
0.7368	Intermediate Similarity	NPD4626	Approved
0.7365	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD844	Approved
0.7305	Intermediate Similarity	NPD4060	Phase 1
0.7293	Intermediate Similarity	NPD5691	Approved
0.7279	Intermediate Similarity	NPD5327	Phase 3
0.7266	Intermediate Similarity	NPD2605	Approved
0.7266	Intermediate Similarity	NPD2606	Approved
0.7259	Intermediate Similarity	NPD1610	Phase 2
0.725	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4624	Approved
0.7241	Intermediate Similarity	NPD7266	Discontinued
0.7239	Intermediate Similarity	NPD5125	Phase 3
0.7239	Intermediate Similarity	NPD5126	Approved
0.7239	Intermediate Similarity	NPD2286	Discontinued
0.7236	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4108	Discontinued
0.7214	Intermediate Similarity	NPD5156	Approved
0.7214	Intermediate Similarity	NPD5155	Approved
0.7209	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2859	Approved
0.719	Intermediate Similarity	NPD2860	Approved
0.7188	Intermediate Similarity	NPD3021	Approved
0.7188	Intermediate Similarity	NPD3022	Approved
0.7172	Intermediate Similarity	NPD6099	Approved
0.7172	Intermediate Similarity	NPD6100	Approved
0.7167	Intermediate Similarity	NPD845	Approved
0.7164	Intermediate Similarity	NPD4093	Discontinued
0.7143	Intermediate Similarity	NPD3594	Approved
0.7143	Intermediate Similarity	NPD3595	Approved
0.7133	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4725	Approved
0.7123	Intermediate Similarity	NPD4726	Approved
0.7123	Intermediate Similarity	NPD4721	Approved
0.7111	Intermediate Similarity	NPD1751	Approved
0.7107	Intermediate Similarity	NPD2934	Approved
0.7107	Intermediate Similarity	NPD2933	Approved
0.7103	Intermediate Similarity	NPD7743	Approved
0.7103	Intermediate Similarity	NPD7742	Approved
0.7101	Intermediate Similarity	NPD8651	Approved
0.7099	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8166	Discontinued
0.7095	Intermediate Similarity	NPD7003	Approved
0.709	Intermediate Similarity	NPD7741	Discontinued
0.7083	Intermediate Similarity	NPD6353	Approved
0.7071	Intermediate Similarity	NPD3636	Approved
0.7071	Intermediate Similarity	NPD3637	Approved
0.7071	Intermediate Similarity	NPD3635	Approved
0.7068	Intermediate Similarity	NPD7340	Approved
0.7059	Intermediate Similarity	NPD3026	Approved
0.7059	Intermediate Similarity	NPD3023	Approved
0.7055	Intermediate Similarity	NPD5406	Approved
0.7055	Intermediate Similarity	NPD5404	Approved
0.7055	Intermediate Similarity	NPD5408	Approved
0.7055	Intermediate Similarity	NPD5405	Approved
0.704	Intermediate Similarity	NPD940	Approved
0.704	Intermediate Similarity	NPD846	Approved
0.7037	Intermediate Similarity	NPD3025	Approved
0.7037	Intermediate Similarity	NPD7228	Approved
0.7037	Intermediate Similarity	NPD3024	Approved
0.7032	Intermediate Similarity	NPD37	Approved
0.702	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3705	Approved
0.7007	Intermediate Similarity	NPD1201	Approved
0.7007	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4967	Phase 2
0.7006	Intermediate Similarity	NPD4965	Approved
0.7006	Intermediate Similarity	NPD4966	Approved
0.6985	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1283	Approved
0.697	Remote Similarity	NPD1398	Phase 1
0.6954	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7041	Phase 2
0.6948	Remote Similarity	NPD7458	Discontinued
0.694	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6234	Discontinued
0.6913	Remote Similarity	NPD3638	Discontinued
0.6892	Remote Similarity	NPD5763	Approved
0.6892	Remote Similarity	NPD5762	Approved
0.6884	Remote Similarity	NPD1091	Approved
0.6879	Remote Similarity	NPD2194	Approved
0.6879	Remote Similarity	NPD2195	Approved
0.6871	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6671	Approved
0.6863	Remote Similarity	NPD6273	Approved
0.6861	Remote Similarity	NPD4589	Approved
0.6861	Remote Similarity	NPD1778	Approved
0.6846	Remote Similarity	NPD7037	Approved
0.6842	Remote Similarity	NPD7390	Discontinued
0.6839	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1548	Phase 1
0.6828	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1613	Approved
0.6825	Remote Similarity	NPD1242	Phase 1
0.6821	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1470	Approved
0.6806	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7294	Phase 1
0.6794	Remote Similarity	NPD1792	Phase 2
0.6791	Remote Similarity	NPD497	Approved
0.679	Remote Similarity	NPD3051	Approved
0.6788	Remote Similarity	NPD1651	Approved
0.6788	Remote Similarity	NPD1357	Approved
0.6786	Remote Similarity	NPD4659	Approved
0.6786	Remote Similarity	NPD8313	Approved
0.6786	Remote Similarity	NPD8312	Approved
0.6781	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5124	Phase 1
0.6772	Remote Similarity	NPD8455	Phase 2
0.6763	Remote Similarity	NPD1281	Approved
0.6761	Remote Similarity	NPD6584	Phase 3
0.6759	Remote Similarity	NPD6405	Approved
0.6759	Remote Similarity	NPD6407	Approved
0.6759	Remote Similarity	NPD8032	Phase 2
0.6748	Remote Similarity	NPD2970	Approved
0.6748	Remote Similarity	NPD2969	Approved
0.6741	Remote Similarity	NPD709	Approved
0.6741	Remote Similarity	NPD7157	Approved
0.6736	Remote Similarity	NPD3027	Phase 3
0.6728	Remote Similarity	NPD6959	Discontinued
0.6716	Remote Similarity	NPD2229	Approved
0.6716	Remote Similarity	NPD2234	Approved
0.6716	Remote Similarity	NPD2228	Approved
0.6716	Remote Similarity	NPD496	Approved
0.6716	Remote Similarity	NPD498	Approved
0.6716	Remote Similarity	NPD495	Approved
0.6715	Remote Similarity	NPD5303	Approved
0.6715	Remote Similarity	NPD5304	Approved
0.6713	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2238	Phase 2
0.6712	Remote Similarity	NPD3109	Approved
0.6712	Remote Similarity	NPD2979	Phase 3
0.6712	Remote Similarity	NPD3110	Approved
0.671	Remote Similarity	NPD4727	Phase 1
0.6707	Remote Similarity	NPD2489	Approved
0.6707	Remote Similarity	NPD27	Approved
0.669	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4103	Phase 2
0.669	Remote Similarity	NPD3764	Approved
0.6689	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7097	Phase 1
0.6688	Remote Similarity	NPD3645	Discontinued
0.6687	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD6667	Approved
0.6667	Remote Similarity	NPD7240	Approved
0.6667	Remote Similarity	NPD6666	Approved
0.6667	Remote Similarity	NPD3657	Discovery
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4628	Phase 3
0.6644	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1611	Approved
0.6642	Remote Similarity	NPD1138	Approved
0.6626	Remote Similarity	NPD7199	Phase 2
0.6623	Remote Similarity	NPD2420	Approved
0.6623	Remote Similarity	NPD2421	Approved
0.6622	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2157	Approved
0.6621	Remote Similarity	NPD7095	Approved
0.6621	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4198	Discontinued
0.6609	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5709	Phase 3

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