NPASS Compound

Structure

CID165646 OpenBabel06191715532D 23 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 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 -5.0000 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 0.0000 -6.0000 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 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 0.0000 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 1.7321 4.0000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 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 1.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 0.8660 -1.5000 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 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	356.472
LogP:	4.585
LogD:	3.948
LogS:	-4.74
# Rotatable Bonds:	9
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	2.554
Fsp3:	0.4
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:	-4.646
MDCK Permeability:	2.3632277589058504e-05
Pgp-inhibitor:	0.235
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.272
30% Bioavailability (F30%):	0.579

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.725
Plasma Protein Binding (PPB):	96.56504821777344%
Volume Distribution (VD):	1.995
Pgp-substrate:	3.8841359615325928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.842
CYP2C19-substrate:	0.625
CYP2C9-inhibitor:	0.696
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.551
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.591
CYP3A4-substrate:	0.37

ADMET: Excretion

Clearance (CL):	10.45
Half-life (T1/2):	0.596

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.625
Drug-inuced Liver Injury (DILI):	0.218
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.955
Carcinogencity:	0.068
Eye Corrosion:	0.005
Eye Irritation:	0.485
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC165646

Natural Product ID:	NPC165646
*Common Name:**	(E)-3-[4-[(2E)-3,7-Dimethylocta-2,6-Dienoxy]-3-Methoxyphenyl]Prop-2-En-1-Ol
IUPAC Name:	(E)-3-[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]-3-methoxyphenyl]prop-2-en-1-ol
Synonyms:
Standard InCHIKey:	UJQXYSRVSXKEES-YIERNNEGSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-16(2)7-5-8-17(3)12-14-23-19-11-10-18(9-6-13-21)15-20(19)22-4/h6-7,9-12,15,21H,5,8,13-14H2,1-4H3/b9-6+,17-12+
SMILES:	CC(=CCC/C(=C/COc1ccc(/C=C/CO)cc1OC)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1800815
PubChem CID:	6439279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568771]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15635247]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6148	Aesculus glabra	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2264	Salvia mexicana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8076	Viburnum luzonicum	Species	Adoxaceae	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	6
Others	9

Activity Type	# Activity
Cell Line	4
Individual Protein	7
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	29000.0	nM	PMID[519180]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	21000.0	nM	PMID[519180]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	31000.0	nM	PMID[519180]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	27000.0	nM	PMID[519180]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.932	n.a.	PMID[519181]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.054	n.a.	PMID[519181]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.272	n.a.	PMID[519181]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.071	n.a.	PMID[519181]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	3.019	n.a.	PMID[519181]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	4.488	n.a.	PMID[519181]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25000.0	nM	PMID[519180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23000.0	nM	PMID[519180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	80.0	%	PMID[519180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	41.0	%	PMID[519180]

☑ 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 NPC165646 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	293
0.1-0.2	1827
0.2-0.3	6389
0.3-0.4	13192
0.4-0.5	3931
0.5-0.6	7124
0.6-0.7	7314
0.7-0.8	2216
0.8-0.85	318
0.85-0.9	78
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC55300
0.9519	High Similarity	NPC258171
0.9519	High Similarity	NPC227894
0.9252	High Similarity	NPC137685
0.9204	High Similarity	NPC199023
0.9167	High Similarity	NPC139617
0.9167	High Similarity	NPC78918
0.9135	High Similarity	NPC192596
0.9038	High Similarity	NPC51633
0.9038	High Similarity	NPC310905
0.9038	High Similarity	NPC12714
0.9027	High Similarity	NPC37858
0.9018	High Similarity	NPC164386
0.8981	High Similarity	NPC246358
0.8981	High Similarity	NPC233731
0.8981	High Similarity	NPC7097
0.8981	High Similarity	NPC36108
0.8957	High Similarity	NPC290451
0.8957	High Similarity	NPC127389
0.8889	High Similarity	NPC114901
0.8889	High Similarity	NPC48990
0.8889	High Similarity	NPC293701
0.8889	High Similarity	NPC94276
0.8889	High Similarity	NPC109822
0.8879	High Similarity	NPC71090
0.8868	High Similarity	NPC292792
0.886	High Similarity	NPC311595
0.886	High Similarity	NPC24474
0.885	High Similarity	NPC86947
0.8818	High Similarity	NPC156840
0.8818	High Similarity	NPC8547
0.8818	High Similarity	NPC257124
0.8818	High Similarity	NPC245552
0.8818	High Similarity	NPC173746
0.8814	High Similarity	NPC194519
0.8785	High Similarity	NPC470393
0.8772	High Similarity	NPC474214
0.8772	High Similarity	NPC124916
0.8772	High Similarity	NPC159916
0.8772	High Similarity	NPC474040
0.8761	High Similarity	NPC221049
0.8739	High Similarity	NPC58607
0.8739	High Similarity	NPC191037
0.8739	High Similarity	NPC178284
0.8729	High Similarity	NPC74478
0.8727	High Similarity	NPC46844
0.8707	High Similarity	NPC207613
0.8696	High Similarity	NPC135961
0.8696	High Similarity	NPC474320
0.8692	High Similarity	NPC38079
0.8692	High Similarity	NPC108875
0.8684	High Similarity	NPC280001
0.8667	High Similarity	NPC319625
0.8667	High Similarity	NPC118787
0.8667	High Similarity	NPC41706
0.8667	High Similarity	NPC111247
0.8667	High Similarity	NPC147821
0.8667	High Similarity	NPC163332
0.8667	High Similarity	NPC183181
0.8667	High Similarity	NPC292056
0.8661	High Similarity	NPC303522
0.8632	High Similarity	NPC184651
0.8632	High Similarity	NPC262156
0.8632	High Similarity	NPC343720
0.8632	High Similarity	NPC312675
0.8632	High Similarity	NPC470804
0.8632	High Similarity	NPC470212
0.8632	High Similarity	NPC473853
0.8632	High Similarity	NPC324571
0.8632	High Similarity	NPC54872
0.8632	High Similarity	NPC113865
0.8609	High Similarity	NPC470626
0.8609	High Similarity	NPC255675
0.8584	High Similarity	NPC294941
0.8559	High Similarity	NPC85488
0.8559	High Similarity	NPC179309
0.8547	High Similarity	NPC204466
0.8534	High Similarity	NPC320987
0.8534	High Similarity	NPC281298
0.8534	High Similarity	NPC310338
0.8534	High Similarity	NPC181969
0.8525	High Similarity	NPC86030
0.8525	High Similarity	NPC5851
0.8525	High Similarity	NPC3439
0.8525	High Similarity	NPC218856
0.8525	High Similarity	NPC248355
0.8525	High Similarity	NPC273295
0.8525	High Similarity	NPC222004
0.8525	High Similarity	NPC285339
0.8525	High Similarity	NPC202582
0.8525	High Similarity	NPC190629
0.8525	High Similarity	NPC226788
0.8525	High Similarity	NPC470258
0.8525	High Similarity	NPC210623
0.8522	High Similarity	NPC293619
0.8522	High Similarity	NPC39793
0.8512	High Similarity	NPC474119
0.85	High Similarity	NPC87113
0.8496	Intermediate Similarity	NPC165106
0.8491	Intermediate Similarity	NPC471576
0.8487	Intermediate Similarity	NPC317769
0.8487	Intermediate Similarity	NPC31344
0.8487	Intermediate Similarity	NPC471693
0.8487	Intermediate Similarity	NPC280704
0.8482	Intermediate Similarity	NPC203924
0.8482	Intermediate Similarity	NPC195873
0.8475	Intermediate Similarity	NPC476343
0.8475	Intermediate Similarity	NPC70752
0.8468	Intermediate Similarity	NPC127326
0.8462	Intermediate Similarity	NPC35071
0.8462	Intermediate Similarity	NPC232316
0.8462	Intermediate Similarity	NPC177475
0.8462	Intermediate Similarity	NPC56214
0.8462	Intermediate Similarity	NPC227217
0.8462	Intermediate Similarity	NPC229401
0.8462	Intermediate Similarity	NPC474565
0.8462	Intermediate Similarity	NPC117780
0.8462	Intermediate Similarity	NPC165133
0.8462	Intermediate Similarity	NPC202474
0.8462	Intermediate Similarity	NPC95614
0.8462	Intermediate Similarity	NPC148615
0.8462	Intermediate Similarity	NPC242885
0.8455	Intermediate Similarity	NPC472338
0.8448	Intermediate Similarity	NPC277460
0.8448	Intermediate Similarity	NPC63083
0.8443	Intermediate Similarity	NPC302378
0.8443	Intermediate Similarity	NPC72529
0.844	Intermediate Similarity	NPC8302
0.8435	Intermediate Similarity	NPC9341
0.8435	Intermediate Similarity	NPC81067
0.843	Intermediate Similarity	NPC304630
0.843	Intermediate Similarity	NPC17837
0.8417	Intermediate Similarity	NPC60517
0.8417	Intermediate Similarity	NPC20443
0.8417	Intermediate Similarity	NPC146886
0.8417	Intermediate Similarity	NPC246704
0.8403	Intermediate Similarity	NPC261661
0.8403	Intermediate Similarity	NPC209567
0.8403	Intermediate Similarity	NPC270326
0.839	Intermediate Similarity	NPC472596
0.839	Intermediate Similarity	NPC189844
0.839	Intermediate Similarity	NPC158949
0.839	Intermediate Similarity	NPC109083
0.839	Intermediate Similarity	NPC166759
0.839	Intermediate Similarity	NPC269843
0.839	Intermediate Similarity	NPC224814
0.839	Intermediate Similarity	NPC14007
0.839	Intermediate Similarity	NPC267064
0.839	Intermediate Similarity	NPC60962
0.8387	Intermediate Similarity	NPC472597
0.8387	Intermediate Similarity	NPC30043
0.8387	Intermediate Similarity	NPC469625
0.8387	Intermediate Similarity	NPC469613
0.8376	Intermediate Similarity	NPC163036
0.8374	Intermediate Similarity	NPC166040
0.8374	Intermediate Similarity	NPC26653
0.8374	Intermediate Similarity	NPC270849
0.8362	Intermediate Similarity	NPC259638
0.8361	Intermediate Similarity	NPC210355
0.8349	Intermediate Similarity	NPC12987
0.8349	Intermediate Similarity	NPC474603
0.8348	Intermediate Similarity	NPC473264
0.8348	Intermediate Similarity	NPC47194
0.8348	Intermediate Similarity	NPC475815
0.8347	Intermediate Similarity	NPC148627
0.8347	Intermediate Similarity	NPC289459
0.8347	Intermediate Similarity	NPC280767
0.8333	Intermediate Similarity	NPC108545
0.8333	Intermediate Similarity	NPC204120
0.8333	Intermediate Similarity	NPC21238
0.8333	Intermediate Similarity	NPC244876
0.8333	Intermediate Similarity	NPC279379
0.832	Intermediate Similarity	NPC35932
0.832	Intermediate Similarity	NPC5423
0.832	Intermediate Similarity	NPC7903
0.832	Intermediate Similarity	NPC184447
0.832	Intermediate Similarity	NPC160991
0.832	Intermediate Similarity	NPC16208
0.8319	Intermediate Similarity	NPC49341
0.8319	Intermediate Similarity	NPC160380
0.8319	Intermediate Similarity	NPC38996
0.8319	Intermediate Similarity	NPC201777
0.8318	Intermediate Similarity	NPC100870
0.8306	Intermediate Similarity	NPC472024
0.8306	Intermediate Similarity	NPC469614
0.8306	Intermediate Similarity	NPC80600
0.8306	Intermediate Similarity	NPC469612
0.8305	Intermediate Similarity	NPC2058
0.8304	Intermediate Similarity	NPC165386
0.8293	Intermediate Similarity	NPC470084
0.8293	Intermediate Similarity	NPC226661
0.8293	Intermediate Similarity	NPC252307
0.8293	Intermediate Similarity	NPC245826
0.8293	Intermediate Similarity	NPC474178
0.8291	Intermediate Similarity	NPC107588
0.8291	Intermediate Similarity	NPC70744
0.8291	Intermediate Similarity	NPC137537
0.8291	Intermediate Similarity	NPC164706
0.8291	Intermediate Similarity	NPC272471
0.8288	Intermediate Similarity	NPC194034

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 NPC165646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	1050
0.2-0.3	1868
0.3-0.4	2631
0.4-0.5	1626
0.5-0.6	964
0.6-0.7	590
0.7-0.8	140
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD2684	Approved
0.8818	High Similarity	NPD228	Approved
0.8696	High Similarity	NPD1357	Approved
0.8571	High Similarity	NPD7843	Approved
0.8509	High Similarity	NPD7157	Approved
0.8496	Intermediate Similarity	NPD5283	Phase 1
0.8288	Intermediate Similarity	NPD290	Approved
0.8205	Intermediate Similarity	NPD5536	Phase 2
0.8182	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD291	Approved
0.808	Intermediate Similarity	NPD3027	Phase 3
0.8017	Intermediate Similarity	NPD3705	Approved
0.8	Intermediate Similarity	NPD9365	Approved
0.8	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD1358	Approved
0.7953	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD821	Approved
0.7886	Intermediate Similarity	NPD2982	Phase 2
0.7886	Intermediate Similarity	NPD2983	Phase 2
0.7881	Intermediate Similarity	NPD6671	Approved
0.7876	Intermediate Similarity	NPD3134	Approved
0.7876	Intermediate Similarity	NPD968	Approved
0.7851	Intermediate Similarity	NPD5846	Approved
0.7851	Intermediate Similarity	NPD6516	Phase 2
0.7805	Intermediate Similarity	NPD2981	Phase 2
0.7787	Intermediate Similarity	NPD3496	Discontinued
0.7778	Intermediate Similarity	NPD9494	Approved
0.7778	Intermediate Similarity	NPD9296	Approved
0.7752	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD3620	Phase 2
0.7752	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD1613	Approved
0.7734	Intermediate Similarity	NPD3144	Approved
0.7734	Intermediate Similarity	NPD3145	Approved
0.7727	Intermediate Similarity	NPD2161	Phase 2
0.7698	Intermediate Similarity	NPD6584	Phase 3
0.7687	Intermediate Similarity	NPD4162	Approved
0.7674	Intermediate Similarity	NPD2674	Phase 3
0.7672	Intermediate Similarity	NPD556	Approved
0.7661	Intermediate Similarity	NPD2235	Phase 2
0.7661	Intermediate Similarity	NPD2231	Phase 2
0.7638	Intermediate Similarity	NPD3018	Phase 2
0.7615	Intermediate Similarity	NPD1558	Phase 1
0.7615	Intermediate Similarity	NPD4060	Phase 1
0.7612	Intermediate Similarity	NPD7153	Discontinued
0.7578	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1778	Approved
0.7561	Intermediate Similarity	NPD4626	Approved
0.7541	Intermediate Similarity	NPD1182	Approved
0.754	Intermediate Similarity	NPD8651	Approved
0.7537	Intermediate Similarity	NPD1375	Discontinued
0.7521	Intermediate Similarity	NPD3022	Approved
0.7521	Intermediate Similarity	NPD3021	Approved
0.7519	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6331	Phase 2
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD2861	Phase 2
0.748	Intermediate Similarity	NPD5585	Approved
0.748	Intermediate Similarity	NPD1820	Approved
0.748	Intermediate Similarity	NPD5691	Approved
0.748	Intermediate Similarity	NPD1818	Approved
0.748	Intermediate Similarity	NPD1819	Approved
0.748	Intermediate Similarity	NPD1817	Approved
0.7479	Intermediate Similarity	NPD5535	Approved
0.746	Intermediate Similarity	NPD3685	Discontinued
0.746	Intermediate Similarity	NPD5327	Phase 3
0.746	Intermediate Similarity	NPD6583	Phase 3
0.746	Intermediate Similarity	NPD6582	Phase 2
0.744	Intermediate Similarity	NPD776	Approved
0.744	Intermediate Similarity	NPD1091	Approved
0.7426	Intermediate Similarity	NPD3060	Approved
0.7426	Intermediate Similarity	NPD4237	Approved
0.7426	Intermediate Similarity	NPD4236	Phase 3
0.7424	Intermediate Similarity	NPD5735	Approved
0.7422	Intermediate Similarity	NPD3691	Phase 2
0.7422	Intermediate Similarity	NPD3690	Phase 2
0.7417	Intermediate Similarity	NPD1241	Discontinued
0.741	Intermediate Similarity	NPD4123	Phase 3
0.7402	Intermediate Similarity	NPD2922	Phase 1
0.7398	Intermediate Similarity	NPD1548	Phase 1
0.7385	Intermediate Similarity	NPD7095	Approved
0.7385	Intermediate Similarity	NPD3180	Approved
0.7385	Intermediate Similarity	NPD3166	Approved
0.7385	Intermediate Similarity	NPD3165	Approved
0.7385	Intermediate Similarity	NPD3167	Approved
0.7385	Intermediate Similarity	NPD3179	Approved
0.7385	Intermediate Similarity	NPD3164	Approved
0.7377	Intermediate Similarity	NPD3596	Phase 2
0.7376	Intermediate Similarity	NPD3687	Approved
0.7376	Intermediate Similarity	NPD3686	Approved
0.7373	Intermediate Similarity	NPD5451	Approved
0.7368	Intermediate Similarity	NPD2653	Approved
0.7368	Intermediate Similarity	NPD6653	Approved
0.7357	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD7526	Approved
0.7357	Intermediate Similarity	NPD52	Approved
0.7348	Intermediate Similarity	NPD4140	Approved
0.7328	Intermediate Similarity	NPD5111	Phase 2
0.7328	Intermediate Similarity	NPD5109	Approved
0.7328	Intermediate Similarity	NPD5718	Phase 2
0.7328	Intermediate Similarity	NPD5110	Phase 2
0.7323	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5241	Discontinued
0.7308	Intermediate Similarity	NPD4908	Phase 1
0.7302	Intermediate Similarity	NPD1610	Phase 2
0.7297	Intermediate Similarity	NPD2933	Approved
0.7297	Intermediate Similarity	NPD2934	Approved
0.7293	Intermediate Similarity	NPD447	Suspended
0.728	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD111	Approved
0.7258	Intermediate Similarity	NPD6581	Approved
0.7258	Intermediate Similarity	NPD6580	Approved
0.7258	Intermediate Similarity	NPD1894	Discontinued
0.7252	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1840	Phase 2
0.7241	Intermediate Similarity	NPD9501	Approved
0.7234	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2859	Approved
0.7232	Intermediate Similarity	NPD2860	Approved
0.7231	Intermediate Similarity	NPD4993	Discontinued
0.7226	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1794	Approved
0.7203	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1798	Approved
0.72	Intermediate Similarity	NPD1797	Approved
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3020	Approved
0.7188	Intermediate Similarity	NPD4749	Approved
0.7188	Intermediate Similarity	NPD4359	Approved
0.7185	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4536	Approved
0.7185	Intermediate Similarity	NPD4538	Approved
0.7183	Intermediate Similarity	NPD2122	Discontinued
0.7174	Intermediate Similarity	NPD5177	Phase 3
0.7174	Intermediate Similarity	NPD6674	Discontinued
0.7164	Intermediate Similarity	NPD6355	Discontinued
0.7164	Intermediate Similarity	NPD3657	Discovery
0.7163	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD9295	Approved
0.7154	Intermediate Similarity	NPD5647	Approved
0.7154	Intermediate Similarity	NPD2557	Approved
0.7154	Intermediate Similarity	NPD558	Phase 2
0.7153	Intermediate Similarity	NPD4678	Approved
0.7153	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD2668	Approved
0.7143	Intermediate Similarity	NPD3531	Approved
0.7143	Intermediate Similarity	NPD3530	Approved
0.7143	Intermediate Similarity	NPD1423	Approved
0.7143	Intermediate Similarity	NPD3532	Approved
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7143	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2667	Approved
0.7133	Intermediate Similarity	NPD1653	Approved
0.7132	Intermediate Similarity	NPD2156	Approved
0.7132	Intermediate Similarity	NPD2154	Approved
0.7132	Intermediate Similarity	NPD2155	Approved
0.7123	Intermediate Similarity	NPD5773	Approved
0.7123	Intermediate Similarity	NPD5772	Approved
0.7111	Intermediate Similarity	NPD2157	Approved
0.7111	Intermediate Similarity	NPD6353	Approved
0.7109	Intermediate Similarity	NPD2230	Approved
0.7109	Intermediate Similarity	NPD2233	Approved
0.7109	Intermediate Similarity	NPD2232	Approved
0.7099	Intermediate Similarity	NPD1712	Approved
0.7092	Intermediate Similarity	NPD1774	Approved
0.7092	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD844	Approved
0.7077	Intermediate Similarity	NPD987	Approved
0.7075	Intermediate Similarity	NPD2563	Approved
0.7075	Intermediate Similarity	NPD2560	Approved
0.7071	Intermediate Similarity	NPD2677	Approved
0.7063	Intermediate Similarity	NPD1651	Approved
0.7063	Intermediate Similarity	NPD3445	Approved
0.7063	Intermediate Similarity	NPD3443	Approved
0.7063	Intermediate Similarity	NPD3444	Approved
0.7059	Intermediate Similarity	NPD6895	Approved
0.7059	Intermediate Similarity	NPD9552	Approved
0.7059	Intermediate Similarity	NPD6896	Approved
0.7054	Intermediate Similarity	NPD1669	Approved
0.705	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3146	Approved
0.7037	Intermediate Similarity	NPD4340	Discontinued
0.7034	Intermediate Similarity	NPD9697	Approved
0.7031	Intermediate Similarity	NPD422	Phase 1
0.7029	Intermediate Similarity	NPD5762	Approved
0.7029	Intermediate Similarity	NPD3540	Phase 1
0.7029	Intermediate Similarity	NPD5763	Approved
0.7023	Intermediate Similarity	NPD4624	Approved
0.7023	Intermediate Similarity	NPD6917	Clinical (unspecified phase)

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