NPASS Compound

Structure

CID151530 OpenBabel06191715522D 23 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 22 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 18 2 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 23 1 0 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	353.835
LogP:	5.472
LogD:	4.583
LogS:	-5.613
# Rotatable Bonds:	9
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	2.402
Fsp3:	0.35
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:	-4.575
MDCK Permeability:	2.6586500098346733e-05
Pgp-inhibitor:	0.824
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.67

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	99.97089385986328%
Volume Distribution (VD):	1.699
Pgp-substrate:	2.231663942337036%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.345
CYP2C19-inhibitor:	0.867
CYP2C19-substrate:	0.334
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.486
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	12.05
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.942
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.953
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.168
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC151530

Natural Product ID:	NPC151530
*Common Name:**	(Z)-Methyl 3-(4-(3,7-Dimethylocta-2,6-Dienyloxy)Phenyl)Acrylate
IUPAC Name:	methyl (Z)-3-[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]phenyl]prop-2-enoate
Synonyms:
Standard InCHIKey:	KSSYIBXTLHIBBX-ICMDQPEBSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-16(2)6-5-7-17(3)14-15-23-19-11-8-18(9-12-19)10-13-20(21)22-4/h6,8-14H,5,7,15H2,1-4H3/b13-10-,17-14+
SMILES:	CC(=CCC/C(=C/COc1ccc(cc1)/C=CC(=O)OC)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334420
PubChem CID:	71720677
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19361168]
NPO25148.1	Helichrysum italicum	Under-species	n.a.	n.a.	Flowered aerial parts	Arzana, Sardinia	2010-Jul	PMID[23265253]
NPO11450	Pseudoceratina purpurea	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26035239]
NPO11450	Pseudoceratina purpurea	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26838	Adenophora triphylla	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29214	Teucrium massiliense	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26838	Adenophora triphylla	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28095	Boronia megastigma	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15808	Vibrio gazogenes	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27879	Ailanthus triphysa	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20978	Alternaria cinerariae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28117	Tor sinensis	Species	Cyprinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27588	Carpolobia lutea	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8266	Solanum anguivi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23311	Libanothamnus tamanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27219	Gonioma kamassi	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27948	Licania carii	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27381	Hypselodoris webbi	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27985	Plantago arenaria	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11450	Pseudoceratina purpurea	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1650	Boykinia watanabei	Species	Saxifragaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[492491]

☑ 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 NPC151530 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	244
0.1-0.2	2013
0.2-0.3	5618
0.3-0.4	11783
0.4-0.5	5547
0.5-0.6	8466
0.6-0.7	7866
0.7-0.8	1015
0.8-0.85	89
0.85-0.9	39
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC157473
0.9899	High Similarity	NPC176971
0.9798	High Similarity	NPC128730
0.97	High Similarity	NPC326447
0.9596	High Similarity	NPC179686
0.9406	High Similarity	NPC473855
0.9307	High Similarity	NPC283546
0.9216	High Similarity	NPC473393
0.92	High Similarity	NPC107101
0.9118	High Similarity	NPC109637
0.9118	High Similarity	NPC2518
0.9109	High Similarity	NPC307425
0.901	High Similarity	NPC13755
0.9	High Similarity	NPC175298
0.8962	High Similarity	NPC473809
0.8952	High Similarity	NPC291837
0.8911	High Similarity	NPC471576
0.8846	High Similarity	NPC238115
0.8835	High Similarity	NPC192596
0.8829	High Similarity	NPC293424
0.8785	High Similarity	NPC231251
0.8785	High Similarity	NPC25067
0.8785	High Similarity	NPC88868
0.8761	High Similarity	NPC235190
0.8761	High Similarity	NPC180006
0.875	High Similarity	NPC37858
0.8738	High Similarity	NPC51633
0.8692	High Similarity	NPC149545
0.8667	High Similarity	NPC470393
0.8667	High Similarity	NPC288760
0.8667	High Similarity	NPC139891
0.8667	High Similarity	NPC227255
0.8661	High Similarity	NPC277460
0.8654	High Similarity	NPC304638
0.8624	High Similarity	NPC199462
0.8596	High Similarity	NPC163200
0.8584	High Similarity	NPC281356
0.8584	High Similarity	NPC98748
0.8571	High Similarity	NPC108875
0.8571	High Similarity	NPC263754
0.8571	High Similarity	NPC38079
0.8571	High Similarity	NPC183154
0.8558	High Similarity	NPC84325
0.8545	High Similarity	NPC90903
0.8532	High Similarity	NPC245552
0.8519	High Similarity	NPC259554
0.8515	High Similarity	NPC471581
0.8505	High Similarity	NPC260952
0.8496	Intermediate Similarity	NPC124916
0.8496	Intermediate Similarity	NPC265547
0.8496	Intermediate Similarity	NPC159916
0.8485	Intermediate Similarity	NPC8002
0.8485	Intermediate Similarity	NPC99886
0.8485	Intermediate Similarity	NPC259134
0.8485	Intermediate Similarity	NPC177844
0.8482	Intermediate Similarity	NPC470860
0.8468	Intermediate Similarity	NPC235250
0.8468	Intermediate Similarity	NPC252004
0.8468	Intermediate Similarity	NPC87563
0.8462	Intermediate Similarity	NPC253746
0.8462	Intermediate Similarity	NPC221798
0.8435	Intermediate Similarity	NPC322569
0.8426	Intermediate Similarity	NPC206341
0.8421	Intermediate Similarity	NPC298796
0.8421	Intermediate Similarity	NPC264976
0.8411	Intermediate Similarity	NPC1065
0.84	Intermediate Similarity	NPC71853
0.8393	Intermediate Similarity	NPC296526
0.8378	Intermediate Similarity	NPC303522
0.8376	Intermediate Similarity	NPC273772
0.8376	Intermediate Similarity	NPC109675
0.8376	Intermediate Similarity	NPC21238
0.8365	Intermediate Similarity	NPC171843
0.8364	Intermediate Similarity	NPC139946
0.8362	Intermediate Similarity	NPC114845
0.8348	Intermediate Similarity	NPC31314
0.8348	Intermediate Similarity	NPC193193
0.8333	Intermediate Similarity	NPC96705
0.8333	Intermediate Similarity	NPC258171
0.8333	Intermediate Similarity	NPC152306
0.8319	Intermediate Similarity	NPC33717
0.8319	Intermediate Similarity	NPC128633
0.8319	Intermediate Similarity	NPC127604
0.8318	Intermediate Similarity	NPC127676
0.8317	Intermediate Similarity	NPC321956
0.8305	Intermediate Similarity	NPC73413
0.8305	Intermediate Similarity	NPC27671
0.8305	Intermediate Similarity	NPC201667
0.8304	Intermediate Similarity	NPC294941
0.8291	Intermediate Similarity	NPC96286
0.8291	Intermediate Similarity	NPC69403
0.8291	Intermediate Similarity	NPC248429
0.8291	Intermediate Similarity	NPC288238
0.8291	Intermediate Similarity	NPC291189
0.8276	Intermediate Similarity	NPC204466
0.8273	Intermediate Similarity	NPC179309
0.8273	Intermediate Similarity	NPC183700
0.8261	Intermediate Similarity	NPC69670
0.825	Intermediate Similarity	NPC224774
0.825	Intermediate Similarity	NPC121740
0.825	Intermediate Similarity	NPC258567
0.823	Intermediate Similarity	NPC220540
0.823	Intermediate Similarity	NPC51345
0.822	Intermediate Similarity	NPC472518
0.8205	Intermediate Similarity	NPC70752
0.8198	Intermediate Similarity	NPC57879
0.819	Intermediate Similarity	NPC202474
0.819	Intermediate Similarity	NPC100870
0.8182	Intermediate Similarity	NPC234639
0.8182	Intermediate Similarity	NPC469453
0.8182	Intermediate Similarity	NPC472519
0.8174	Intermediate Similarity	NPC101503
0.8167	Intermediate Similarity	NPC474476
0.8151	Intermediate Similarity	NPC60517
0.8151	Intermediate Similarity	NPC89630
0.8151	Intermediate Similarity	NPC146886
0.8151	Intermediate Similarity	NPC20443
0.8151	Intermediate Similarity	NPC246704
0.8148	Intermediate Similarity	NPC8302
0.8131	Intermediate Similarity	NPC298224
0.8125	Intermediate Similarity	NPC165646
0.8125	Intermediate Similarity	NPC266116
0.8125	Intermediate Similarity	NPC280760
0.812	Intermediate Similarity	NPC471877
0.812	Intermediate Similarity	NPC267064
0.8108	Intermediate Similarity	NPC183648
0.8108	Intermediate Similarity	NPC46844
0.8108	Intermediate Similarity	NPC141068
0.8103	Intermediate Similarity	NPC234956
0.8099	Intermediate Similarity	NPC473993
0.8099	Intermediate Similarity	NPC194841
0.8095	Intermediate Similarity	NPC95755
0.8087	Intermediate Similarity	NPC217423
0.8087	Intermediate Similarity	NPC45104
0.8087	Intermediate Similarity	NPC199209
0.8087	Intermediate Similarity	NPC212643
0.8083	Intermediate Similarity	NPC289459
0.8083	Intermediate Similarity	NPC471827
0.8083	Intermediate Similarity	NPC471828
0.8067	Intermediate Similarity	NPC315807
0.8067	Intermediate Similarity	NPC108545
0.8067	Intermediate Similarity	NPC279379
0.8056	Intermediate Similarity	NPC38209
0.8051	Intermediate Similarity	NPC144418
0.8049	Intermediate Similarity	NPC19242
0.8049	Intermediate Similarity	NPC183348
0.8049	Intermediate Similarity	NPC113098
0.8049	Intermediate Similarity	NPC282230
0.8037	Intermediate Similarity	NPC94343
0.8036	Intermediate Similarity	NPC23332
0.8036	Intermediate Similarity	NPC55300
0.8034	Intermediate Similarity	NPC471504
0.8034	Intermediate Similarity	NPC473290
0.8034	Intermediate Similarity	NPC474874
0.8034	Intermediate Similarity	NPC230951
0.8034	Intermediate Similarity	NPC222175
0.802	Intermediate Similarity	NPC173443
0.8018	Intermediate Similarity	NPC471954
0.8018	Intermediate Similarity	NPC75272
0.8017	Intermediate Similarity	NPC213552
0.8017	Intermediate Similarity	NPC120225
0.8017	Intermediate Similarity	NPC188327
0.8017	Intermediate Similarity	NPC70744
0.8017	Intermediate Similarity	NPC101894
0.8017	Intermediate Similarity	NPC272471
0.8017	Intermediate Similarity	NPC107588
0.8017	Intermediate Similarity	NPC137537
0.8017	Intermediate Similarity	NPC475236
0.8017	Intermediate Similarity	NPC234109
0.8017	Intermediate Similarity	NPC329272
0.8017	Intermediate Similarity	NPC164706
0.8	Intermediate Similarity	NPC281277
0.8	Intermediate Similarity	NPC19290
0.8	Intermediate Similarity	NPC268317
0.8	Intermediate Similarity	NPC291899
0.7984	Intermediate Similarity	NPC470977
0.7984	Intermediate Similarity	NPC272650
0.7984	Intermediate Similarity	NPC15083
0.7984	Intermediate Similarity	NPC196979
0.7984	Intermediate Similarity	NPC29734
0.7984	Intermediate Similarity	NPC267336
0.7984	Intermediate Similarity	NPC470976
0.7983	Intermediate Similarity	NPC13007
0.7983	Intermediate Similarity	NPC257188
0.7982	Intermediate Similarity	NPC328593
0.7982	Intermediate Similarity	NPC33749
0.7982	Intermediate Similarity	NPC261453
0.7981	Intermediate Similarity	NPC32977
0.7981	Intermediate Similarity	NPC81010
0.7967	Intermediate Similarity	NPC168710
0.7967	Intermediate Similarity	NPC295970
0.7967	Intermediate Similarity	NPC170546
0.7967	Intermediate Similarity	NPC66246
0.7963	Intermediate Similarity	NPC305205
0.7951	Intermediate Similarity	NPC243688
0.7951	Intermediate Similarity	NPC37512
0.7949	Intermediate Similarity	NPC61779
0.7934	Intermediate Similarity	NPC165556
0.7934	Intermediate Similarity	NPC473626
0.7934	Intermediate Similarity	NPC27352

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 NPC151530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1091
0.2-0.3	1479
0.3-0.4	2676
0.4-0.5	1865
0.5-0.6	1127
0.6-0.7	559
0.7-0.8	126
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.97	High Similarity	NPD3134	Approved
0.9412	High Similarity	NPD1358	Approved
0.8667	High Similarity	NPD9697	Approved
0.8624	High Similarity	NPD5535	Approved
0.8545	High Similarity	NPD1241	Discontinued
0.8426	Intermediate Similarity	NPD2684	Approved
0.8421	Intermediate Similarity	NPD5691	Approved
0.8276	Intermediate Similarity	NPD3496	Discontinued
0.8125	Intermediate Similarity	NPD7843	Approved
0.8103	Intermediate Similarity	NPD5585	Approved
0.8034	Intermediate Similarity	NPD4626	Approved
0.8017	Intermediate Similarity	NPD1894	Discontinued
0.7965	Intermediate Similarity	NPD821	Approved
0.7931	Intermediate Similarity	NPD5536	Phase 2
0.7913	Intermediate Similarity	NPD7157	Approved
0.7899	Intermediate Similarity	NPD422	Phase 1
0.7886	Intermediate Similarity	NPD6832	Phase 2
0.7881	Intermediate Similarity	NPD1778	Approved
0.7838	Intermediate Similarity	NPD290	Approved
0.7769	Intermediate Similarity	NPD4359	Approved
0.7748	Intermediate Similarity	NPD968	Approved
0.7724	Intermediate Similarity	NPD1019	Discontinued
0.7712	Intermediate Similarity	NPD9545	Approved
0.7699	Intermediate Similarity	NPD5451	Approved
0.7692	Intermediate Similarity	NPD3596	Phase 2
0.7686	Intermediate Similarity	NPD9717	Approved
0.768	Intermediate Similarity	NPD5163	Phase 2
0.768	Intermediate Similarity	NPD5746	Approved
0.7667	Intermediate Similarity	NPD3847	Discontinued
0.7642	Intermediate Similarity	NPD2797	Approved
0.7619	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6798	Discontinued
0.7619	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4340	Discontinued
0.7563	Intermediate Similarity	NPD6581	Approved
0.7563	Intermediate Similarity	NPD6580	Approved
0.7559	Intermediate Similarity	NPD4062	Phase 3
0.7559	Intermediate Similarity	NPD6233	Phase 2
0.7559	Intermediate Similarity	NPD5745	Approved
0.7541	Intermediate Similarity	NPD3972	Approved
0.7524	Intermediate Similarity	NPD9365	Approved
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD3142	Approved
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD4140	Approved
0.75	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3140	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.748	Intermediate Similarity	NPD3685	Discontinued
0.748	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD1282	Approved
0.746	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD1535	Discovery
0.7459	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2557	Approved
0.7444	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6355	Discontinued
0.7438	Intermediate Similarity	NPD17	Approved
0.7438	Intermediate Similarity	NPD6516	Phase 2
0.7438	Intermediate Similarity	NPD5846	Approved
0.7436	Intermediate Similarity	NPD5283	Phase 1
0.7419	Intermediate Similarity	NPD3225	Approved
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7402	Intermediate Similarity	NPD7095	Approved
0.7398	Intermediate Similarity	NPD1481	Phase 2
0.7388	Intermediate Similarity	NPD4628	Phase 3
0.7381	Intermediate Similarity	NPD454	Approved
0.7381	Intermediate Similarity	NPD2237	Approved
0.736	Intermediate Similarity	NPD987	Approved
0.736	Intermediate Similarity	NPD1203	Approved
0.736	Intermediate Similarity	NPD6362	Approved
0.735	Intermediate Similarity	NPD769	Approved
0.7344	Intermediate Similarity	NPD3268	Approved
0.7339	Intermediate Similarity	NPD6582	Phase 2
0.7339	Intermediate Similarity	NPD5327	Phase 3
0.7339	Intermediate Similarity	NPD6583	Phase 3
0.7333	Intermediate Similarity	NPD3887	Approved
0.7328	Intermediate Similarity	NPD7097	Phase 1
0.7323	Intermediate Similarity	NPD2614	Approved
0.7317	Intermediate Similarity	NPD1281	Approved
0.7317	Intermediate Similarity	NPD1611	Approved
0.7311	Intermediate Similarity	NPD6671	Approved
0.7308	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD1933	Approved
0.7308	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5647	Approved
0.7295	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD592	Approved
0.7288	Intermediate Similarity	NPD594	Approved
0.7287	Intermediate Similarity	NPD8032	Phase 2
0.7287	Intermediate Similarity	NPD4870	Approved
0.728	Intermediate Similarity	NPD1876	Approved
0.7273	Intermediate Similarity	NPD1182	Approved
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7265	Intermediate Similarity	NPD228	Approved
0.7258	Intermediate Similarity	NPD1608	Approved
0.725	Intermediate Similarity	NPD9493	Approved
0.7231	Intermediate Similarity	NPD2979	Phase 3
0.7231	Intermediate Similarity	NPD4307	Phase 2
0.7226	Intermediate Similarity	NPD6799	Approved
0.7218	Intermediate Similarity	NPD4476	Approved
0.7218	Intermediate Similarity	NPD2239	Approved
0.7218	Intermediate Similarity	NPD2796	Approved
0.7218	Intermediate Similarity	NPD2240	Approved
0.7218	Intermediate Similarity	NPD4477	Approved
0.7213	Intermediate Similarity	NPD2594	Approved
0.7213	Intermediate Similarity	NPD3049	Approved
0.7213	Intermediate Similarity	NPD1651	Approved
0.7213	Intermediate Similarity	NPD3443	Approved
0.7213	Intermediate Similarity	NPD3444	Approved
0.7213	Intermediate Similarity	NPD2595	Approved
0.7213	Intermediate Similarity	NPD3445	Approved
0.7213	Intermediate Similarity	NPD1357	Approved
0.7213	Intermediate Similarity	NPD6382	Discontinued
0.7209	Intermediate Similarity	NPD1048	Approved
0.7209	Intermediate Similarity	NPD1296	Phase 2
0.7207	Intermediate Similarity	NPD1238	Approved
0.72	Intermediate Similarity	NPD4129	Approved
0.72	Intermediate Similarity	NPD6540	Phase 3
0.72	Intermediate Similarity	NPD6542	Approved
0.72	Intermediate Similarity	NPD6539	Approved
0.72	Intermediate Similarity	NPD2428	Approved
0.72	Intermediate Similarity	NPD6543	Approved
0.72	Intermediate Similarity	NPD2429	Approved
0.7185	Intermediate Similarity	NPD1652	Phase 2
0.7179	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3705	Approved
0.7176	Intermediate Similarity	NPD4618	Approved
0.7176	Intermediate Similarity	NPD4622	Approved
0.7165	Intermediate Similarity	NPD3690	Phase 2
0.7165	Intermediate Similarity	NPD6584	Phase 3
0.7165	Intermediate Similarity	NPD3691	Phase 2
0.7164	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2353	Approved
0.7156	Intermediate Similarity	NPD2934	Approved
0.7156	Intermediate Similarity	NPD2933	Approved
0.7155	Intermediate Similarity	NPD2182	Approved
0.7154	Intermediate Similarity	NPD2554	Approved
0.7154	Intermediate Similarity	NPD2556	Approved
0.7153	Intermediate Similarity	NPD7440	Discontinued
0.7143	Intermediate Similarity	NPD6541	Approved
0.7143	Intermediate Similarity	NPD6538	Approved
0.7143	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD3748	Approved
0.7122	Intermediate Similarity	NPD6273	Approved
0.7122	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2186	Approved
0.7121	Intermediate Similarity	NPD6653	Approved
0.7121	Intermediate Similarity	NPD2653	Approved
0.7119	Intermediate Similarity	NPD1137	Approved
0.7119	Intermediate Similarity	NPD1139	Approved
0.7115	Intermediate Similarity	NPD111	Approved
0.7111	Intermediate Similarity	NPD4534	Discontinued
0.7109	Intermediate Similarity	NPD9494	Approved
0.7109	Intermediate Similarity	NPD4993	Discontinued
0.7091	Intermediate Similarity	NPD2859	Approved
0.7091	Intermediate Similarity	NPD2860	Approved
0.709	Intermediate Similarity	NPD2935	Discontinued
0.7087	Intermediate Similarity	NPD1817	Approved
0.7087	Intermediate Similarity	NPD1820	Approved
0.7087	Intermediate Similarity	NPD3567	Approved
0.7087	Intermediate Similarity	NPD3568	Approved
0.7087	Intermediate Similarity	NPD1818	Approved
0.7087	Intermediate Similarity	NPD1819	Approved
0.708	Intermediate Similarity	NPD291	Approved
0.7077	Intermediate Similarity	NPD2313	Discontinued
0.7077	Intermediate Similarity	NPD411	Approved
0.7069	Intermediate Similarity	NPD5374	Approved
0.7069	Intermediate Similarity	NPD5373	Approved
0.7068	Intermediate Similarity	NPD5689	Approved
0.7068	Intermediate Similarity	NPD5688	Approved
0.7059	Intermediate Similarity	NPD1138	Approved
0.7054	Intermediate Similarity	NPD4908	Phase 1
0.7054	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD447	Suspended
0.704	Intermediate Similarity	NPD1610	Phase 2
0.704	Intermediate Similarity	NPD1091	Approved
0.7037	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7018	Phase 2
0.7031	Intermediate Similarity	NPD2798	Approved
0.7023	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2667	Approved
0.7016	Intermediate Similarity	NPD2668	Approved
0.7015	Intermediate Similarity	NPD7033	Discontinued
0.7015	Intermediate Similarity	NPD4308	Phase 3
0.7009	Intermediate Similarity	NPD9295	Approved
0.7008	Intermediate Similarity	NPD8651	Approved
0.7008	Intermediate Similarity	NPD196	Phase 1
0.7008	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4110	Phase 3
0.7	Intermediate Similarity	NPD2598	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3180	Approved
0.7	Intermediate Similarity	NPD3165	Approved
0.7	Intermediate Similarity	NPD3166	Approved
0.7	Intermediate Similarity	NPD3167	Approved
0.7	Intermediate Similarity	NPD3164	Approved
0.7	Intermediate Similarity	NPD3179	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