NPASS Compound

Structure

NPC471110 OpenBabel07101719252D 42 42 0 0 1 0 0 0 0 0999 V2000 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 14.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 16.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 17.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 19.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 19.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 22.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 22.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 22.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 20.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 22.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 23.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 21.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 21.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 41 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 31 1 0 0 0 0 22 35 1 0 0 0 0 23 25 2 0 0 0 0 23 30 1 0 0 0 0 24 26 2 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 26 33 1 0 0 0 0 27 30 2 0 0 0 0 27 34 1 0 0 0 0 28 32 1 0 0 0 0 28 36 1 0 0 0 0 29 32 1 0 0 0 0 29 42 1 0 0 0 0 31 37 2 0 0 0 0 32 38 1 0 0 0 0 33 34 2 0 0 0 0 33 39 1 0 0 0 0 34 41 1 0 0 0 0 35 40 2 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.42
Volume:	651.072
LogP:	8.62
LogD:	4.332
LogS:	-4.164
# Rotatable Bonds:	29
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	3.147
Fsp3:	0.714
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.216
MDCK Permeability:	1.8270491636940278e-05
Pgp-inhibitor:	0.549
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	98.19404602050781%
Volume Distribution (VD):	0.725
Pgp-substrate:	0.39150747656822205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	7.103
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.481
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.507
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.089
Skin Sensitization:	0.976
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC471110

Natural Product ID:	NPC471110
*Common Name:**	1-(Omega-Feruloyldocosanoyl)Glycerol
IUPAC Name:	2,3-dihydroxypropyl (E)-25-(4-hydroxy-3-methoxyphenyl)-23-oxopentacos-24-enoate
Synonyms:
Standard InCHIKey:	ZVGREMLOMIBGBX-WJTDDFOZSA-N
Standard InCHI:	InChI=1S/C35H58O7/c1-41-34-27-30(24-26-33(34)39)23-25-31(37)21-19-17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18-20-22-35(40)42-29-32(38)28-36/h23-27,32,36,38-39H,2-22,28-29H2,1H3/b25-23+
SMILES:	COC1=C(C=CC(=C1)C=CC(=O)CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375495
PubChem CID:	73347275
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives

*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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell Line	MT4	Homo sapiens	IC50	=	16200.0	nM	PMID[475303]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC90	=	3.63	uM	PMID[475303]

☑ 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 NPC471110 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	274
0.1-0.2	1140
0.2-0.3	3301
0.3-0.4	7708
0.4-0.5	10681
0.5-0.6	4160
0.6-0.7	8882
0.7-0.8	5912
0.8-0.85	468
0.85-0.9	135
0.9-0.95	33
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9766	High Similarity	NPC475468
0.9291	High Similarity	NPC280767
0.9213	High Similarity	NPC20443
0.9213	High Similarity	NPC312404
0.9213	High Similarity	NPC273686
0.9213	High Similarity	NPC60517
0.9213	High Similarity	NPC146886
0.9134	High Similarity	NPC164778
0.9134	High Similarity	NPC257976
0.9134	High Similarity	NPC242372
0.9134	High Similarity	NPC4181
0.9077	High Similarity	NPC278308
0.9055	High Similarity	NPC114298
0.9008	High Similarity	NPC83062
0.9	High Similarity	NPC20404
0.9	High Similarity	NPC123228
0.9	High Similarity	NPC293641
0.9	High Similarity	NPC5018
0.9	High Similarity	NPC123722
0.9	High Similarity	NPC151167
0.9	High Similarity	NPC276466
0.9	High Similarity	NPC20287
0.9	High Similarity	NPC12022
0.8976	High Similarity	NPC194416
0.8976	High Similarity	NPC177291
0.8971	High Similarity	NPC284409
0.8963	High Similarity	NPC90431
0.8923	High Similarity	NPC213552
0.8923	High Similarity	NPC84076
0.8923	High Similarity	NPC120225
0.8923	High Similarity	NPC303680
0.8923	High Similarity	NPC90128
0.8923	High Similarity	NPC179777
0.8905	High Similarity	NPC289690
0.8905	High Similarity	NPC288452
0.8898	High Similarity	NPC158949
0.8898	High Similarity	NPC204466
0.8864	High Similarity	NPC241354
0.8864	High Similarity	NPC304622
0.8857	High Similarity	NPC469683
0.8846	High Similarity	NPC289459
0.8837	High Similarity	NPC163083
0.8828	High Similarity	NPC201777
0.8828	High Similarity	NPC70752
0.8819	High Similarity	NPC202474
0.8815	High Similarity	NPC135127
0.8797	High Similarity	NPC215941
0.8797	High Similarity	NPC137427
0.8797	High Similarity	NPC123196
0.8797	High Similarity	NPC172673
0.8797	High Similarity	NPC319282
0.8797	High Similarity	NPC65935
0.8797	High Similarity	NPC311419
0.8797	High Similarity	NPC275724
0.8797	High Similarity	NPC244246
0.8786	High Similarity	NPC469615
0.8769	High Similarity	NPC246704
0.875	High Similarity	NPC470990
0.875	High Similarity	NPC113295
0.8741	High Similarity	NPC478242
0.874	High Similarity	NPC299406
0.8723	High Similarity	NPC53884
0.8723	High Similarity	NPC258671
0.8705	High Similarity	NPC100675
0.8702	High Similarity	NPC257589
0.8702	High Similarity	NPC53305
0.8692	High Similarity	NPC244876
0.869	High Similarity	NPC473773
0.869	High Similarity	NPC475579
0.8676	High Similarity	NPC176814
0.8676	High Similarity	NPC300776
0.8676	High Similarity	NPC68779
0.8676	High Similarity	NPC4982
0.8676	High Similarity	NPC5310
0.8671	High Similarity	NPC472969
0.8671	High Similarity	NPC98009
0.8667	High Similarity	NPC239302
0.8667	High Similarity	NPC50763
0.8662	High Similarity	NPC98356
0.8661	High Similarity	NPC272471
0.8661	High Similarity	NPC107588
0.8661	High Similarity	NPC70744
0.8661	High Similarity	NPC137537
0.8661	High Similarity	NPC205502
0.8661	High Similarity	NPC309434
0.8661	High Similarity	NPC164706
0.8661	High Similarity	NPC203124
0.8657	High Similarity	NPC195292
0.8652	High Similarity	NPC304956
0.8647	High Similarity	NPC226661
0.8647	High Similarity	NPC110313
0.8639	High Similarity	NPC131532
0.8636	High Similarity	NPC276014
0.8636	High Similarity	NPC92207
0.8636	High Similarity	NPC127937
0.8633	High Similarity	NPC474784
0.8633	High Similarity	NPC322021
0.8623	High Similarity	NPC126206
0.8621	High Similarity	NPC118033
0.8621	High Similarity	NPC473680
0.8621	High Similarity	NPC473579
0.8621	High Similarity	NPC475311
0.8621	High Similarity	NPC475454
0.8615	High Similarity	NPC286573
0.8611	High Similarity	NPC476394
0.8611	High Similarity	NPC98809
0.8603	High Similarity	NPC129889
0.8603	High Similarity	NPC327410
0.8603	High Similarity	NPC307006
0.8601	High Similarity	NPC221383
0.8601	High Similarity	NPC143892
0.8601	High Similarity	NPC283081
0.8601	High Similarity	NPC299090
0.8594	High Similarity	NPC24474
0.8594	High Similarity	NPC311595
0.8593	High Similarity	NPC469480
0.8582	High Similarity	NPC48315
0.8571	High Similarity	NPC32163
0.8571	High Similarity	NPC281020
0.8571	High Similarity	NPC16651
0.8551	High Similarity	NPC471665
0.8551	High Similarity	NPC120852
0.8551	High Similarity	NPC471664
0.855	High Similarity	NPC160900
0.855	High Similarity	NPC18984
0.855	High Similarity	NPC106659
0.855	High Similarity	NPC229084
0.854	High Similarity	NPC106406
0.8529	High Similarity	NPC111888
0.8527	High Similarity	NPC2058
0.8521	High Similarity	NPC473090
0.8521	High Similarity	NPC160378
0.8519	High Similarity	NPC142985
0.8519	High Similarity	NPC66905
0.8507	High Similarity	NPC109275
0.8504	High Similarity	NPC281277
0.85	High Similarity	NPC147379
0.8489	Intermediate Similarity	NPC281780
0.8478	Intermediate Similarity	NPC204592
0.8478	Intermediate Similarity	NPC139519
0.8467	Intermediate Similarity	NPC159418
0.8467	Intermediate Similarity	NPC155209
0.8467	Intermediate Similarity	NPC168799
0.8467	Intermediate Similarity	NPC283823
0.8462	Intermediate Similarity	NPC473909
0.8462	Intermediate Similarity	NPC470848
0.8462	Intermediate Similarity	NPC470849
0.8462	Intermediate Similarity	NPC109083
0.8462	Intermediate Similarity	NPC143120
0.8462	Intermediate Similarity	NPC269843
0.8462	Intermediate Similarity	NPC14007
0.8462	Intermediate Similarity	NPC189844
0.8462	Intermediate Similarity	NPC60962
0.8462	Intermediate Similarity	NPC274960
0.8462	Intermediate Similarity	NPC224814
0.8456	Intermediate Similarity	NPC470896
0.8456	Intermediate Similarity	NPC198388
0.8456	Intermediate Similarity	NPC473275
0.845	Intermediate Similarity	NPC37858
0.8446	Intermediate Similarity	NPC469888
0.8438	Intermediate Similarity	NPC164386
0.8435	Intermediate Similarity	NPC75695
0.8429	Intermediate Similarity	NPC325625
0.8425	Intermediate Similarity	NPC233669
0.8421	Intermediate Similarity	NPC3221
0.8417	Intermediate Similarity	NPC157554
0.8414	Intermediate Similarity	NPC1580
0.8409	Intermediate Similarity	NPC21238
0.8406	Intermediate Similarity	NPC249791
0.8406	Intermediate Similarity	NPC119060
0.8406	Intermediate Similarity	NPC237594
0.8406	Intermediate Similarity	NPC476387
0.8403	Intermediate Similarity	NPC287495
0.8403	Intermediate Similarity	NPC9370
0.8397	Intermediate Similarity	NPC470212
0.8397	Intermediate Similarity	NPC54872
0.8397	Intermediate Similarity	NPC470804
0.8397	Intermediate Similarity	NPC324571
0.8397	Intermediate Similarity	NPC113865
0.8397	Intermediate Similarity	NPC262156
0.8397	Intermediate Similarity	NPC312675
0.8397	Intermediate Similarity	NPC184651
0.8397	Intermediate Similarity	NPC343720
0.8397	Intermediate Similarity	NPC473853
0.8394	Intermediate Similarity	NPC25581
0.8394	Intermediate Similarity	NPC18074
0.8394	Intermediate Similarity	NPC61
0.8394	Intermediate Similarity	NPC5419
0.838	Intermediate Similarity	NPC253722
0.838	Intermediate Similarity	NPC52664
0.838	Intermediate Similarity	NPC104956
0.838	Intermediate Similarity	NPC140502
0.838	Intermediate Similarity	NPC472410
0.838	Intermediate Similarity	NPC253481
0.838	Intermediate Similarity	NPC31751
0.8378	Intermediate Similarity	NPC19380
0.8378	Intermediate Similarity	NPC105942
0.8378	Intermediate Similarity	NPC205392
0.8378	Intermediate Similarity	NPC44730
0.8378	Intermediate Similarity	NPC146277

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 NPC471110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	782
0.2-0.3	1747
0.3-0.4	2459
0.4-0.5	1976
0.5-0.6	1093
0.6-0.7	686
0.7-0.8	154
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.855	High Similarity	NPD4379	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD9494	Approved
0.8125	Intermediate Similarity	NPD8166	Discontinued
0.811	Intermediate Similarity	NPD228	Approved
0.8015	Intermediate Similarity	NPD5536	Phase 2
0.7945	Intermediate Similarity	NPD6190	Approved
0.7943	Intermediate Similarity	NPD230	Phase 1
0.7943	Intermediate Similarity	NPD447	Suspended
0.7917	Intermediate Similarity	NPD7266	Discontinued
0.7914	Intermediate Similarity	NPD3027	Phase 3
0.7887	Intermediate Similarity	NPD6653	Approved
0.7877	Intermediate Similarity	NPD4628	Phase 3
0.7877	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4110	Phase 3
0.7838	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6355	Discontinued
0.7801	Intermediate Similarity	NPD6233	Phase 2
0.7795	Intermediate Similarity	NPD1358	Approved
0.7778	Intermediate Similarity	NPD1934	Approved
0.7742	Intermediate Similarity	NPD3882	Suspended
0.7742	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6798	Discontinued
0.7724	Intermediate Similarity	NPD2935	Discontinued
0.7698	Intermediate Similarity	NPD5647	Approved
0.7697	Intermediate Similarity	NPD3455	Phase 2
0.7676	Intermediate Similarity	NPD4062	Phase 3
0.7669	Intermediate Similarity	NPD7685	Pre-registration
0.7658	Intermediate Similarity	NPD8127	Discontinued
0.7634	Intermediate Similarity	NPD7843	Approved
0.7632	Intermediate Similarity	NPD1653	Approved
0.763	Intermediate Similarity	NPD1357	Approved
0.7613	Intermediate Similarity	NPD2801	Approved
0.7613	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7054	Approved
0.759	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3134	Approved
0.7576	Intermediate Similarity	NPD1241	Discontinued
0.7564	Intermediate Similarity	NPD3817	Phase 2
0.7556	Intermediate Similarity	NPD9545	Approved
0.7546	Intermediate Similarity	NPD7074	Phase 3
0.7546	Intermediate Similarity	NPD7472	Approved
0.7535	Intermediate Similarity	NPD7095	Approved
0.7532	Intermediate Similarity	NPD6234	Discontinued
0.7531	Intermediate Similarity	NPD3818	Discontinued
0.7518	Intermediate Similarity	NPD3496	Discontinued
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD825	Approved
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD826	Approved
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7075	Discontinued
0.7463	Intermediate Similarity	NPD7157	Approved
0.7462	Intermediate Similarity	NPD2684	Approved
0.7451	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4626	Approved
0.7444	Intermediate Similarity	NPD5283	Phase 1
0.7436	Intermediate Similarity	NPD37	Approved
0.7426	Intermediate Similarity	NPD1894	Discontinued
0.7423	Intermediate Similarity	NPD7228	Approved
0.741	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD9717	Approved
0.741	Intermediate Similarity	NPD7808	Phase 3
0.7405	Intermediate Similarity	NPD4966	Approved
0.7405	Intermediate Similarity	NPD4965	Approved
0.7405	Intermediate Similarity	NPD4967	Phase 2
0.7389	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1613	Approved
0.7379	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3620	Phase 2
0.7378	Intermediate Similarity	NPD5844	Phase 1
0.7376	Intermediate Similarity	NPD2797	Approved
0.7372	Intermediate Similarity	NPD6385	Approved
0.7372	Intermediate Similarity	NPD5691	Approved
0.7372	Intermediate Similarity	NPD6386	Approved
0.7368	Intermediate Similarity	NPD6799	Approved
0.7368	Intermediate Similarity	NPD1511	Approved
0.7365	Intermediate Similarity	NPD2240	Approved
0.7365	Intermediate Similarity	NPD2438	Suspended
0.7365	Intermediate Similarity	NPD2239	Approved
0.7361	Intermediate Similarity	NPD3268	Approved
0.7353	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7251	Discontinued
0.7343	Intermediate Similarity	NPD6832	Phase 2
0.7338	Intermediate Similarity	NPD1535	Discovery
0.7333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1933	Approved
0.7329	Intermediate Similarity	NPD555	Phase 2
0.7319	Intermediate Similarity	NPD1778	Approved
0.7308	Intermediate Similarity	NPD4380	Phase 2
0.7305	Intermediate Similarity	NPD1283	Approved
0.7297	Intermediate Similarity	NPD2799	Discontinued
0.729	Intermediate Similarity	NPD3686	Approved
0.729	Intermediate Similarity	NPD3687	Approved
0.7289	Intermediate Similarity	NPD6797	Phase 2
0.7286	Intermediate Similarity	NPD9269	Phase 2
0.7286	Intermediate Similarity	NPD1481	Phase 2
0.7285	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD9493	Approved
0.7278	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7819	Suspended
0.7273	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD1512	Approved
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4534	Discontinued
0.7267	Intermediate Similarity	NPD2424	Discontinued
0.7266	Intermediate Similarity	NPD3847	Discontinued
0.7256	Intermediate Similarity	NPD7473	Discontinued
0.7254	Intermediate Similarity	NPD1203	Approved
0.7254	Intermediate Similarity	NPD6362	Approved
0.7252	Intermediate Similarity	NPD290	Approved
0.7244	Intermediate Similarity	NPD7458	Discontinued
0.7241	Intermediate Similarity	NPD411	Approved
0.7233	Intermediate Similarity	NPD5402	Approved
0.7233	Intermediate Similarity	NPD5353	Approved
0.7226	Intermediate Similarity	NPD5403	Approved
0.7222	Intermediate Similarity	NPD7199	Phase 2
0.7215	Intermediate Similarity	NPD6801	Discontinued
0.7214	Intermediate Similarity	NPD3705	Approved
0.7208	Intermediate Similarity	NPD3146	Approved
0.7208	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD258	Approved
0.7203	Intermediate Similarity	NPD257	Approved
0.7197	Intermediate Similarity	NPD7028	Phase 2
0.7192	Intermediate Similarity	NPD2674	Phase 3
0.7192	Intermediate Similarity	NPD8032	Phase 2
0.7192	Intermediate Similarity	NPD259	Phase 1
0.7178	Intermediate Similarity	NPD6232	Discontinued
0.7171	Intermediate Similarity	NPD3750	Approved
0.717	Intermediate Similarity	NPD1465	Phase 2
0.7163	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD6873	Phase 2
0.7152	Intermediate Similarity	NPD5958	Discontinued
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7038	Approved
0.7143	Intermediate Similarity	NPD7039	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7134	Intermediate Similarity	NPD824	Approved
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD9570	Approved
0.7132	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD291	Approved
0.7124	Intermediate Similarity	NPD3887	Approved
0.7124	Intermediate Similarity	NPD2354	Approved
0.7122	Intermediate Similarity	NPD1651	Approved
0.7122	Intermediate Similarity	NPD5585	Approved
0.7114	Intermediate Similarity	NPD7097	Phase 1
0.7103	Intermediate Similarity	NPD2614	Approved
0.7103	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5401	Approved
0.7095	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD422	Phase 1
0.7092	Intermediate Similarity	NPD1281	Approved
0.7089	Intermediate Similarity	NPD6599	Discontinued
0.7086	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5763	Approved
0.7086	Intermediate Similarity	NPD5762	Approved
0.7086	Intermediate Similarity	NPD6004	Phase 3
0.7086	Intermediate Similarity	NPD6002	Phase 3
0.7086	Intermediate Similarity	NPD6005	Phase 3
0.7086	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7768	Phase 2
0.7078	Intermediate Similarity	NPD7440	Discontinued
0.7075	Intermediate Similarity	NPD6663	Approved
0.7075	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1510	Phase 2
0.7067	Intermediate Similarity	NPD7033	Discontinued
0.7067	Intermediate Similarity	NPD4308	Phase 3
0.7063	Intermediate Similarity	NPD8455	Phase 2
0.7047	Intermediate Similarity	NPD2653	Approved
0.7042	Intermediate Similarity	NPD3972	Approved
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.7039	Intermediate Similarity	NPD1549	Phase 2
0.7034	Intermediate Similarity	NPD9569	Approved
0.7034	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5736	Approved
0.7032	Intermediate Similarity	NPD4357	Discontinued
0.703	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1240	Approved
0.7027	Intermediate Similarity	NPD943	Approved
0.7027	Intermediate Similarity	NPD4140	Approved
0.7025	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3111	Phase 1
0.702	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6032	Approved
0.702	Intermediate Similarity	NPD1551	Phase 2
0.7014	Intermediate Similarity	NPD3266	Approved
0.7014	Intermediate Similarity	NPD3267	Approved
0.7012	Intermediate Similarity	NPD2821	Approved
0.7007	Intermediate Similarity	NPD3764	Approved
0.7007	Intermediate Similarity	NPD3144	Approved
0.7007	Intermediate Similarity	NPD2313	Discontinued
0.7007	Intermediate Similarity	NPD2629	Approved
0.7007	Intermediate Similarity	NPD3145	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