NPASS Compound

Structure

NPC79933 OpenBabel07101719512D 29 31 0 0 1 0 0 0 0 0999 V2000 -5.3249 -0.5806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9648 1.1136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 -1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6776 -0.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6557 0.1625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 19 2 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 19 21 1 0 0 0 0 20 4 1 6 0 0 0 20 24 1 0 0 0 0 22 28 1 0 0 0 0 23 12 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 6 0 0 0 25 27 1 6 0 0 0 26 29 2 0 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.32
Volume:	456.913
LogP:	7.402
LogD:	6.656
LogS:	-5.944
# Rotatable Bonds:	8
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	3.881
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	1.3497099644155242e-05
Pgp-inhibitor:	0.495
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	98.2917709350586%
Volume Distribution (VD):	1.536
Pgp-substrate:	1.6094675064086914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.449
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.34
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.322
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.779
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	9.182
Half-life (T1/2):	0.306

ADMET: Toxicity

hERG Blockers:	0.416
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.461
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.21
Skin Sensitization:	0.927
Carcinogencity:	0.023
Eye Corrosion:	0.435
Eye Irritation:	0.739
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC79933

Natural Product ID:	NPC79933
*Common Name:**	Calicoferol E
IUPAC Name:	(1R,3aS,4S,7aR)-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,4,6,7-hexahydro-1H-inden-5-one
Synonyms:	Calicoferol E
Standard InCHIKey:	OZROZYIBIZOAQQ-DLBXBJKMSA-N
Standard InCHI:	InChI=1S/C27H42O2/c1-18(2)7-6-8-20(4)24-13-14-25-23(26(29)15-16-27(24,25)5)12-10-21-17-22(28)11-9-19(21)3/h9,11,17-18,20,23-25,28H,6-8,10,12-16H2,1-5H3/t20-,23+,24-,25+,27-/m1/s1
SMILES:	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H](CCc3cc(ccc3C)O)C(=O)CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456936
PubChem CID:	5283685
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32924	gorgonian astrogorgia sp.	Species	n.a.	n.a.	n.a.	Chinese	n.a.	PMID[21982797]
NPO32639	muricella	Genus	Acanthogorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7595595]
NPO32639	muricella	Genus	Acanthogorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834177]

☑ 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	16
LD50	1

Activity Type	# Activity
Individual Protein	16
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1661	Individual Protein	ALK tyrosine kinase receptor	Homo sapiens	IC50	=	4730.0	nM	PMID[514140]
NPT1660	Individual Protein	NUAK family SNF1-like kinase 1	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]
NPT1659	Individual Protein	Tyrosine-protein kinase receptor UFO	Homo sapiens	IC50	=	32600.0	nM	PMID[514140]
NPT1436	Individual Protein	Focal adhesion kinase 1	Homo sapiens	IC50	=	9630.0	nM	PMID[514140]
NPT1438	Individual Protein	Insulin-like growth factor I receptor	Homo sapiens	IC50	=	2460.0	nM	PMID[514140]
NPT491	Individual Protein	Dual specificity mitogen-activated protein kinase kinase 1	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	71500.0	nM	PMID[514140]
NPT1658	Individual Protein	Serine/threonine-protein kinase NEK2	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]
NPT1657	Individual Protein	Serine/threonine-protein kinase NEK6	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]
NPT1656	Individual Protein	Protein kinase N1	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	2170.0	nM	PMID[514140]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	6010.0	nM	PMID[514140]
NPT140	Organism	Artemia	Artemia	LD50	>	100.0	ppm	PMID[514139]
NPT728	Individual Protein	Serine/threonine-protein kinase AKT	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	>	100000.0	nM	PMID[514140]

☑ 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 NPC79933 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	253
0.1-0.2	1347
0.2-0.3	2208
0.3-0.4	6478
0.4-0.5	11917
0.5-0.6	11549
0.6-0.7	7734
0.7-0.8	1127
0.8-0.85	54
0.85-0.9	20
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC258366
1.0	High Similarity	NPC31296
1.0	High Similarity	NPC473974
0.9561	High Similarity	NPC190501
0.9561	High Similarity	NPC318552
0.9328	High Similarity	NPC269598
0.9	High Similarity	NPC15127
0.8983	High Similarity	NPC32322
0.8983	High Similarity	NPC259703
0.8974	High Similarity	NPC42657
0.8934	High Similarity	NPC30491
0.8934	High Similarity	NPC262936
0.8879	High Similarity	NPC247858
0.8879	High Similarity	NPC474387
0.8879	High Similarity	NPC137496
0.8879	High Similarity	NPC474358
0.8879	High Similarity	NPC257540
0.8879	High Similarity	NPC154511
0.8824	High Similarity	NPC241001
0.8824	High Similarity	NPC21216
0.8772	High Similarity	NPC322753
0.875	High Similarity	NPC154696
0.8678	High Similarity	NPC121168
0.8678	High Similarity	NPC176208
0.8667	High Similarity	NPC474175
0.8607	High Similarity	NPC198014
0.8607	High Similarity	NPC471187
0.8595	High Similarity	NPC249340
0.8595	High Similarity	NPC253627
0.8595	High Similarity	NPC162935
0.8583	High Similarity	NPC68339
0.8537	High Similarity	NPC181334
0.8525	High Similarity	NPC11250
0.8512	High Similarity	NPC164852
0.8487	Intermediate Similarity	NPC471926
0.8482	Intermediate Similarity	NPC261573
0.8482	Intermediate Similarity	NPC8931
0.8482	Intermediate Similarity	NPC120693
0.8468	Intermediate Similarity	NPC87985
0.843	Intermediate Similarity	NPC99734
0.843	Intermediate Similarity	NPC478121
0.8421	Intermediate Similarity	NPC228737
0.8417	Intermediate Similarity	NPC164649
0.8417	Intermediate Similarity	NPC328694
0.8417	Intermediate Similarity	NPC48342
0.8403	Intermediate Similarity	NPC471928
0.8403	Intermediate Similarity	NPC471925
0.8403	Intermediate Similarity	NPC471924
0.84	Intermediate Similarity	NPC71610
0.8376	Intermediate Similarity	NPC286222
0.8362	Intermediate Similarity	NPC13482
0.8361	Intermediate Similarity	NPC190971
0.8348	Intermediate Similarity	NPC11554
0.8346	Intermediate Similarity	NPC276238
0.8333	Intermediate Similarity	NPC69424
0.8333	Intermediate Similarity	NPC188677
0.8333	Intermediate Similarity	NPC72667
0.8333	Intermediate Similarity	NPC176130
0.8333	Intermediate Similarity	NPC78364
0.8333	Intermediate Similarity	NPC84672
0.832	Intermediate Similarity	NPC137750
0.8319	Intermediate Similarity	NPC469719
0.8319	Intermediate Similarity	NPC327811
0.8319	Intermediate Similarity	NPC254965
0.8254	Intermediate Similarity	NPC254492
0.8244	Intermediate Similarity	NPC252343
0.8244	Intermediate Similarity	NPC477596
0.824	Intermediate Similarity	NPC199273
0.8226	Intermediate Similarity	NPC297057
0.822	Intermediate Similarity	NPC228425
0.822	Intermediate Similarity	NPC250323
0.8214	Intermediate Similarity	NPC211885
0.8211	Intermediate Similarity	NPC328504
0.8205	Intermediate Similarity	NPC141782
0.8205	Intermediate Similarity	NPC222905
0.8203	Intermediate Similarity	NPC171460
0.8198	Intermediate Similarity	NPC260000
0.8175	Intermediate Similarity	NPC137416
0.8174	Intermediate Similarity	NPC69332
0.8174	Intermediate Similarity	NPC95178
0.8174	Intermediate Similarity	NPC29989
0.8174	Intermediate Similarity	NPC70843
0.8168	Intermediate Similarity	NPC477594
0.8167	Intermediate Similarity	NPC322197
0.8145	Intermediate Similarity	NPC142198
0.8145	Intermediate Similarity	NPC77569
0.8142	Intermediate Similarity	NPC472585
0.814	Intermediate Similarity	NPC108129
0.8136	Intermediate Similarity	NPC260323
0.8136	Intermediate Similarity	NPC176279
0.8125	Intermediate Similarity	NPC280869
0.8125	Intermediate Similarity	NPC92730
0.8125	Intermediate Similarity	NPC96024
0.8125	Intermediate Similarity	NPC3009
0.812	Intermediate Similarity	NPC88141
0.8108	Intermediate Similarity	NPC202986
0.8103	Intermediate Similarity	NPC151477
0.8103	Intermediate Similarity	NPC320439
0.8099	Intermediate Similarity	NPC471668
0.8099	Intermediate Similarity	NPC477453
0.8095	Intermediate Similarity	NPC471927
0.8095	Intermediate Similarity	NPC474766
0.8088	Intermediate Similarity	NPC477209
0.8083	Intermediate Similarity	NPC268160
0.8083	Intermediate Similarity	NPC195922
0.808	Intermediate Similarity	NPC282577
0.8077	Intermediate Similarity	NPC476847
0.8077	Intermediate Similarity	NPC471851
0.8067	Intermediate Similarity	NPC62867
0.8067	Intermediate Similarity	NPC177962
0.8067	Intermediate Similarity	NPC231717
0.8062	Intermediate Similarity	NPC303910
0.8062	Intermediate Similarity	NPC25736
0.806	Intermediate Similarity	NPC248287
0.806	Intermediate Similarity	NPC234548
0.8051	Intermediate Similarity	NPC252544
0.8051	Intermediate Similarity	NPC321252
0.8047	Intermediate Similarity	NPC19432
0.8036	Intermediate Similarity	NPC225464
0.8034	Intermediate Similarity	NPC317305
0.8034	Intermediate Similarity	NPC64586
0.8033	Intermediate Similarity	NPC76308
0.8033	Intermediate Similarity	NPC477136
0.8033	Intermediate Similarity	NPC325295
0.8029	Intermediate Similarity	NPC477207
0.8017	Intermediate Similarity	NPC192948
0.8017	Intermediate Similarity	NPC35797
0.8017	Intermediate Similarity	NPC147179
0.8016	Intermediate Similarity	NPC273683
0.8015	Intermediate Similarity	NPC165612
0.8	Intermediate Similarity	NPC120545
0.7985	Intermediate Similarity	NPC98804
0.7985	Intermediate Similarity	NPC477592
0.7984	Intermediate Similarity	NPC229894
0.7983	Intermediate Similarity	NPC95716
0.7983	Intermediate Similarity	NPC470770
0.7983	Intermediate Similarity	NPC177576
0.7983	Intermediate Similarity	NPC77772
0.7983	Intermediate Similarity	NPC266937
0.797	Intermediate Similarity	NPC43353
0.7969	Intermediate Similarity	NPC471930
0.7969	Intermediate Similarity	NPC471929
0.7969	Intermediate Similarity	NPC15837
0.7969	Intermediate Similarity	NPC471935
0.7966	Intermediate Similarity	NPC58865
0.7955	Intermediate Similarity	NPC477139
0.7955	Intermediate Similarity	NPC78307
0.7955	Intermediate Similarity	NPC18982
0.7955	Intermediate Similarity	NPC475627
0.7955	Intermediate Similarity	NPC475457
0.7955	Intermediate Similarity	NPC475346
0.7953	Intermediate Similarity	NPC75432
0.7951	Intermediate Similarity	NPC277394
0.7951	Intermediate Similarity	NPC141001
0.7951	Intermediate Similarity	NPC28951
0.7951	Intermediate Similarity	NPC38893
0.7951	Intermediate Similarity	NPC308311
0.7951	Intermediate Similarity	NPC299252
0.7951	Intermediate Similarity	NPC61062
0.7951	Intermediate Similarity	NPC325646
0.7951	Intermediate Similarity	NPC477137
0.7951	Intermediate Similarity	NPC219112
0.7951	Intermediate Similarity	NPC308828
0.7946	Intermediate Similarity	NPC292730
0.7946	Intermediate Similarity	NPC216520
0.7946	Intermediate Similarity	NPC82664
0.7946	Intermediate Similarity	NPC132271
0.7946	Intermediate Similarity	NPC473388
0.7939	Intermediate Similarity	NPC243305
0.7937	Intermediate Similarity	NPC164947
0.7937	Intermediate Similarity	NPC91478
0.7937	Intermediate Similarity	NPC321402
0.7931	Intermediate Similarity	NPC117115
0.7928	Intermediate Similarity	NPC316301
0.7928	Intermediate Similarity	NPC27323
0.7926	Intermediate Similarity	NPC477593
0.7923	Intermediate Similarity	NPC30174
0.7923	Intermediate Similarity	NPC206028
0.7923	Intermediate Similarity	NPC117899
0.7923	Intermediate Similarity	NPC288290
0.7923	Intermediate Similarity	NPC131684
0.792	Intermediate Similarity	NPC98305
0.7917	Intermediate Similarity	NPC46940
0.791	Intermediate Similarity	NPC7464
0.791	Intermediate Similarity	NPC193358
0.7907	Intermediate Similarity	NPC471530
0.7903	Intermediate Similarity	NPC93071
0.7903	Intermediate Similarity	NPC182240
0.7903	Intermediate Similarity	NPC126002
0.7895	Intermediate Similarity	NPC202225
0.7895	Intermediate Similarity	NPC225506
0.7891	Intermediate Similarity	NPC123506
0.7886	Intermediate Similarity	NPC16030
0.7886	Intermediate Similarity	NPC304510
0.7886	Intermediate Similarity	NPC172219
0.7881	Intermediate Similarity	NPC31274
0.7876	Intermediate Similarity	NPC32674
0.7874	Intermediate Similarity	NPC275145
0.7869	Intermediate Similarity	NPC23402
0.7863	Intermediate Similarity	NPC155072

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 NPC79933 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	892
0.2-0.3	1042
0.3-0.4	2571
0.4-0.5	2375
0.5-0.6	1532
0.6-0.7	417
0.7-0.8	55
0.8-0.85	5
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9561	High Similarity	NPD2932	Approved
0.9561	High Similarity	NPD3019	Approved
0.8824	High Similarity	NPD3023	Approved
0.8824	High Similarity	NPD3026	Approved
0.8814	High Similarity	NPD3025	Approved
0.8814	High Similarity	NPD3024	Approved
0.8651	High Similarity	NPD6663	Approved
0.8629	High Similarity	NPD5736	Approved
0.843	Intermediate Similarity	NPD4059	Approved
0.8417	Intermediate Similarity	NPD3091	Approved
0.8145	Intermediate Similarity	NPD3092	Approved
0.8125	Intermediate Similarity	NPD3020	Approved
0.8077	Intermediate Similarity	NPD8032	Phase 2
0.7984	Intermediate Similarity	NPD3095	Discontinued
0.7956	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD3094	Phase 2
0.7857	Intermediate Similarity	NPD2860	Approved
0.7857	Intermediate Similarity	NPD2859	Approved
0.7815	Intermediate Similarity	NPD3021	Approved
0.7815	Intermediate Similarity	NPD3022	Approved
0.7769	Intermediate Similarity	NPD7635	Approved
0.7768	Intermediate Similarity	NPD2934	Approved
0.7768	Intermediate Similarity	NPD2933	Approved
0.776	Intermediate Similarity	NPD1651	Approved
0.7717	Intermediate Similarity	NPD1201	Approved
0.7692	Intermediate Similarity	NPD4624	Approved
0.7674	Intermediate Similarity	NPD1876	Approved
0.7674	Intermediate Similarity	NPD1283	Approved
0.7626	Intermediate Similarity	NPD8166	Discontinued
0.7619	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1755	Approved
0.7586	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD1751	Approved
0.7544	Intermediate Similarity	NPD1809	Phase 2
0.752	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1470	Approved
0.7481	Intermediate Similarity	NPD4140	Approved
0.748	Intermediate Similarity	NPD4093	Discontinued
0.7478	Intermediate Similarity	NPD288	Approved
0.7462	Intermediate Similarity	NPD5327	Phase 3
0.7442	Intermediate Similarity	NPD1281	Approved
0.7391	Intermediate Similarity	NPD7742	Approved
0.7391	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD844	Approved
0.7391	Intermediate Similarity	NPD7743	Approved
0.7377	Intermediate Similarity	NPD1792	Phase 2
0.7372	Intermediate Similarity	NPD6353	Approved
0.7368	Intermediate Similarity	NPD845	Approved
0.7361	Intermediate Similarity	NPD6273	Approved
0.7355	Intermediate Similarity	NPD2342	Discontinued
0.7353	Intermediate Similarity	NPD3620	Phase 2
0.7353	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD6099	Approved
0.7328	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7610	Discontinued
0.7299	Intermediate Similarity	NPD5735	Approved
0.7293	Intermediate Similarity	NPD2194	Approved
0.7293	Intermediate Similarity	NPD2195	Approved
0.728	Intermediate Similarity	NPD2229	Approved
0.728	Intermediate Similarity	NPD2234	Approved
0.728	Intermediate Similarity	NPD2228	Approved
0.7279	Intermediate Similarity	NPD7028	Phase 2
0.7239	Intermediate Similarity	NPD3635	Approved
0.7239	Intermediate Similarity	NPD3637	Approved
0.7239	Intermediate Similarity	NPD3636	Approved
0.7236	Intermediate Similarity	NPD4750	Phase 3
0.7222	Intermediate Similarity	NPD5951	Approved
0.7222	Intermediate Similarity	NPD2629	Approved
0.7206	Intermediate Similarity	NPD3764	Approved
0.7185	Intermediate Similarity	NPD2606	Approved
0.7185	Intermediate Similarity	NPD2605	Approved
0.7176	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6355	Discontinued
0.7165	Intermediate Similarity	NPD256	Approved
0.7165	Intermediate Similarity	NPD255	Approved
0.7154	Intermediate Similarity	NPD2286	Discontinued
0.7154	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD1242	Phase 1
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7003	Approved
0.7133	Intermediate Similarity	NPD4110	Phase 3
0.7132	Intermediate Similarity	NPD5156	Approved
0.7132	Intermediate Similarity	NPD7095	Approved
0.7132	Intermediate Similarity	NPD5155	Approved
0.7131	Intermediate Similarity	NPD1444	Approved
0.7131	Intermediate Similarity	NPD1445	Approved
0.7121	Intermediate Similarity	NPD1608	Approved
0.7121	Intermediate Similarity	NPD3972	Approved
0.712	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD111	Approved
0.7101	Intermediate Similarity	NPD2979	Phase 3
0.7101	Intermediate Similarity	NPD4060	Phase 1
0.7092	Intermediate Similarity	NPD5405	Approved
0.7092	Intermediate Similarity	NPD5404	Approved
0.7092	Intermediate Similarity	NPD5408	Approved
0.7092	Intermediate Similarity	NPD5406	Approved
0.709	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1164	Approved
0.7083	Intermediate Similarity	NPD940	Approved
0.7083	Intermediate Similarity	NPD846	Approved
0.7063	Intermediate Similarity	NPD3638	Discontinued
0.7059	Intermediate Similarity	NPD3594	Approved
0.7059	Intermediate Similarity	NPD3595	Approved
0.7023	Intermediate Similarity	NPD4589	Approved
0.7009	Intermediate Similarity	NPD1693	Approved
0.7008	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4097	Suspended
0.6986	Remote Similarity	NPD7390	Discontinued
0.6985	Remote Similarity	NPD2861	Phase 2
0.6977	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2935	Discontinued
0.6963	Remote Similarity	NPD2797	Approved
0.6947	Remote Similarity	NPD5585	Approved
0.694	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5762	Approved
0.6923	Remote Similarity	NPD5763	Approved
0.6918	Remote Similarity	NPD3300	Phase 2
0.6917	Remote Similarity	NPD2066	Phase 3
0.6912	Remote Similarity	NPD257	Approved
0.6912	Remote Similarity	NPD2798	Approved
0.6912	Remote Similarity	NPD258	Approved
0.6901	Remote Similarity	NPD2799	Discontinued
0.6899	Remote Similarity	NPD6671	Approved
0.6897	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD17	Approved
0.6894	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6696	Suspended
0.6885	Remote Similarity	NPD1930	Approved
0.6885	Remote Similarity	NPD1929	Approved
0.6885	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5283	Phase 1
0.687	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7741	Discontinued
0.687	Remote Similarity	NPD5304	Approved
0.687	Remote Similarity	NPD7009	Phase 2
0.687	Remote Similarity	NPD5303	Approved
0.6864	Remote Similarity	NPD688	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3028	Approved
0.6859	Remote Similarity	NPD8127	Discontinued
0.6857	Remote Similarity	NPD6346	Approved
0.6857	Remote Similarity	NPD943	Approved
0.6853	Remote Similarity	NPD4476	Approved
0.6853	Remote Similarity	NPD2531	Phase 2
0.6853	Remote Similarity	NPD4477	Approved
0.6853	Remote Similarity	NPD2438	Suspended
0.6849	Remote Similarity	NPD8131	Suspended
0.6846	Remote Similarity	NPD9568	Approved
0.6842	Remote Similarity	NPD3847	Discontinued
0.6838	Remote Similarity	NPD1088	Approved
0.6835	Remote Similarity	NPD3268	Approved
0.6824	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1793	Approved
0.6822	Remote Similarity	NPD1791	Approved
0.6818	Remote Similarity	NPD5691	Approved
0.6806	Remote Similarity	NPD2344	Approved
0.6797	Remote Similarity	NPD6858	Approved
0.6797	Remote Similarity	NPD7094	Approved
0.6791	Remote Similarity	NPD1535	Discovery
0.6788	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7305	Phase 1
0.678	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7157	Approved
0.6761	Remote Similarity	NPD6653	Approved
0.6761	Remote Similarity	NPD2157	Approved
0.6755	Remote Similarity	NPD7458	Discontinued
0.6753	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1241	Discontinued
0.6742	Remote Similarity	NPD1894	Discontinued
0.6742	Remote Similarity	NPD9545	Approved
0.6742	Remote Similarity	NPD7330	Discontinued
0.6741	Remote Similarity	NPD1481	Phase 2
0.6741	Remote Similarity	NPD2233	Approved
0.6741	Remote Similarity	NPD2232	Approved
0.6741	Remote Similarity	NPD2230	Approved
0.6739	Remote Similarity	NPD4208	Discontinued
0.6738	Remote Similarity	NPD825	Approved
0.6738	Remote Similarity	NPD826	Approved
0.6719	Remote Similarity	NPD228	Approved
0.6716	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3645	Discontinued
0.6711	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7315	Approved
0.6694	Remote Similarity	NPD1237	Approved
0.6694	Remote Similarity	NPD5909	Discontinued
0.6692	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD497	Approved
0.6691	Remote Similarity	NPD1669	Approved
0.6691	Remote Similarity	NPD4359	Approved
0.6691	Remote Similarity	NPD2614	Approved
0.6691	Remote Similarity	NPD4207	Discontinued
0.669	Remote Similarity	NPD4721	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