NPASS Compound

Structure

NPC13482 OpenBabel07101719242D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 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 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 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 1.7321 -0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 1.0000 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 -3.4641 0.0000 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 -0.8660 -0.5000 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 0.0000 1.0000 0.0000 C 0 0 1 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.21
Volume:	327.051
LogP:	5.957
LogD:	4.89
LogS:	-6.013
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	3.857
Fsp3:	0.6
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:	-4.914
MDCK Permeability:	1.9073559087701142e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.63
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	98.35960388183594%
Volume Distribution (VD):	4.26
Pgp-substrate:	2.1264727115631104%

ADMET: Metabolism

CYP1A2-inhibitor:	0.572
CYP1A2-substrate:	0.748
CYP2C19-inhibitor:	0.538
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.415
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.845
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.732
CYP3A4-substrate:	0.591

ADMET: Excretion

Clearance (CL):	7.405
Half-life (T1/2):	0.07

ADMET: Toxicity

hERG Blockers:	0.527
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.782
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.927
Carcinogencity:	0.74
Eye Corrosion:	0.042
Eye Irritation:	0.908
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC13482

Natural Product ID:	NPC13482
*Common Name:**	(4Bs,8As)-4B,8,8-Trimethyl-1-Propan-2-Yl-5,6,7,8A-Tetrahydrophenanthren-2-Ol
IUPAC Name:	(4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a-tetrahydrophenanthren-2-ol
Synonyms:
Standard InCHIKey:	PGAVPWXNOKXKIU-FXAWDEMLSA-N
Standard InCHI:	InChI=1S/C20H28O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h7-10,13,17,21H,6,11-12H2,1-5H3/t17-,20+/m0/s1
SMILES:	CC(c1c(O)ccc2c1C=C[C@@H]1[C@]2(C)CCCC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450305
PubChem CID:	484443
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29845	Chamaecyparis nootkatensis	Species	Cupressaceae	Eukaryota	n.a.	Alaskan	n.a.	PMID[15387645]
NPO29845	Chamaecyparis nootkatensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
ED50	1
GI50	6
MIC	6

Activity Type	# Activity
Cell Line	7
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.7	ug ml-1	PMID[475441]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[475441]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[475441]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[475441]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[475441]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[475441]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[475441]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	16.0	ug.mL-1	PMID[475441]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[475441]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	32.0	ug.mL-1	PMID[475441]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	16.0	ug.mL-1	PMID[475441]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4.0	ug.mL-1	PMID[475441]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	8.0	ug.mL-1	PMID[475441]

☑ 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 NPC13482 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	355
0.1-0.2	1801
0.2-0.3	3874
0.3-0.4	10836
0.4-0.5	8500
0.5-0.6	10008
0.6-0.7	5788
0.7-0.8	1212
0.8-0.85	206
0.85-0.9	74
0.9-0.95	38
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC250323
0.9615	High Similarity	NPC141782
0.9524	High Similarity	NPC176279
0.9524	High Similarity	NPC260323
0.9439	High Similarity	NPC195922
0.9358	High Similarity	NPC477136
0.9327	High Similarity	NPC151477
0.9266	High Similarity	NPC471668
0.9259	High Similarity	NPC268160
0.9231	High Similarity	NPC21594
0.9174	High Similarity	NPC147179
0.9174	High Similarity	NPC35797
0.9174	High Similarity	NPC192948
0.9167	High Similarity	NPC715
0.9159	High Similarity	NPC470770
0.9159	High Similarity	NPC322753
0.9159	High Similarity	NPC95716
0.9159	High Similarity	NPC266937
0.9151	High Similarity	NPC58865
0.9135	High Similarity	NPC117115
0.9118	High Similarity	NPC225506
0.9118	High Similarity	NPC211885
0.9091	High Similarity	NPC308311
0.9091	High Similarity	NPC477137
0.9091	High Similarity	NPC308828
0.9091	High Similarity	NPC219112
0.9091	High Similarity	NPC38893
0.9074	High Similarity	NPC62867
0.9074	High Similarity	NPC46940
0.9074	High Similarity	NPC228425
0.9074	High Similarity	NPC177962
0.9057	High Similarity	NPC11554
0.9048	High Similarity	NPC271274
0.9027	High Similarity	NPC259703
0.9027	High Similarity	NPC32322
0.902	High Similarity	NPC122005
0.902	High Similarity	NPC252821
0.9018	High Similarity	NPC93071
0.9009	High Similarity	NPC16030
0.9009	High Similarity	NPC172219
0.9009	High Similarity	NPC304510
0.8981	High Similarity	NPC77772
0.8962	High Similarity	NPC320439
0.8929	High Similarity	NPC471671
0.8929	High Similarity	NPC469609
0.8929	High Similarity	NPC154030
0.8922	High Similarity	NPC77492
0.8919	High Similarity	NPC469663
0.8919	High Similarity	NPC92
0.8889	High Similarity	NPC296683
0.885	High Similarity	NPC469644
0.885	High Similarity	NPC126002
0.8829	High Similarity	NPC469719
0.8807	High Similarity	NPC151537
0.8796	High Similarity	NPC314187
0.8783	High Similarity	NPC154696
0.8774	High Similarity	NPC138942
0.8772	High Similarity	NPC135467
0.8772	High Similarity	NPC260832
0.8762	High Similarity	NPC168829
0.875	High Similarity	NPC474358
0.875	High Similarity	NPC257540
0.875	High Similarity	NPC141001
0.875	High Similarity	NPC137496
0.875	High Similarity	NPC474387
0.875	High Similarity	NPC247858
0.875	High Similarity	NPC154511
0.8739	High Similarity	NPC107240
0.8739	High Similarity	NPC471534
0.8738	High Similarity	NPC225464
0.8725	High Similarity	NPC222146
0.8725	High Similarity	NPC8392
0.8725	High Similarity	NPC144682
0.8716	High Similarity	NPC132720
0.8696	High Similarity	NPC241001
0.8692	High Similarity	NPC155072
0.8679	High Similarity	NPC288411
0.8679	High Similarity	NPC238696
0.8667	High Similarity	NPC252105
0.8667	High Similarity	NPC51015
0.8654	High Similarity	NPC299762
0.8654	High Similarity	NPC33675
0.8654	High Similarity	NPC92730
0.8649	High Similarity	NPC322239
0.8627	High Similarity	NPC27323
0.8627	High Similarity	NPC316301
0.8627	High Similarity	NPC289769
0.8627	High Similarity	NPC152415
0.8627	High Similarity	NPC245187
0.8621	High Similarity	NPC249340
0.8621	High Similarity	NPC162935
0.8621	High Similarity	NPC253627
0.8598	High Similarity	NPC99557
0.8598	High Similarity	NPC219286
0.8596	High Similarity	NPC164649
0.8596	High Similarity	NPC48342
0.8585	High Similarity	NPC269212
0.8584	High Similarity	NPC312105
0.8559	High Similarity	NPC471179
0.8558	High Similarity	NPC32674
0.8558	High Similarity	NPC79241
0.8558	High Similarity	NPC6597
0.8558	High Similarity	NPC156313
0.8547	High Similarity	NPC121168
0.8547	High Similarity	NPC11250
0.8547	High Similarity	NPC176208
0.8547	High Similarity	NPC152946
0.8547	High Similarity	NPC471794
0.8534	High Similarity	NPC328504
0.8529	High Similarity	NPC55903
0.8522	High Similarity	NPC151197
0.8522	High Similarity	NPC42657
0.8519	High Similarity	NPC54765
0.8509	High Similarity	NPC299180
0.8487	Intermediate Similarity	NPC76119
0.8487	Intermediate Similarity	NPC4286
0.8482	Intermediate Similarity	NPC317869
0.8475	Intermediate Similarity	NPC198014
0.8475	Intermediate Similarity	NPC471187
0.8468	Intermediate Similarity	NPC165770
0.8468	Intermediate Similarity	NPC4493
0.8468	Intermediate Similarity	NPC225679
0.8468	Intermediate Similarity	NPC476632
0.8462	Intermediate Similarity	NPC312132
0.8462	Intermediate Similarity	NPC132271
0.8462	Intermediate Similarity	NPC292730
0.8462	Intermediate Similarity	NPC259512
0.8462	Intermediate Similarity	NPC473388
0.8462	Intermediate Similarity	NPC216520
0.8462	Intermediate Similarity	NPC82664
0.8448	Intermediate Similarity	NPC68339
0.8448	Intermediate Similarity	NPC325544
0.8448	Intermediate Similarity	NPC99734
0.8448	Intermediate Similarity	NPC318581
0.8448	Intermediate Similarity	NPC318552
0.8448	Intermediate Similarity	NPC477037
0.8448	Intermediate Similarity	NPC190501
0.8447	Intermediate Similarity	NPC76938
0.8435	Intermediate Similarity	NPC206
0.8431	Intermediate Similarity	NPC306074
0.8431	Intermediate Similarity	NPC204210
0.8431	Intermediate Similarity	NPC155908
0.8431	Intermediate Similarity	NPC304541
0.8426	Intermediate Similarity	NPC47284
0.8421	Intermediate Similarity	NPC261973
0.8417	Intermediate Similarity	NPC71610
0.8411	Intermediate Similarity	NPC108497
0.8403	Intermediate Similarity	NPC181334
0.8396	Intermediate Similarity	NPC72729
0.8393	Intermediate Similarity	NPC43525
0.839	Intermediate Similarity	NPC297057
0.839	Intermediate Similarity	NPC478058
0.8376	Intermediate Similarity	NPC164852
0.8365	Intermediate Similarity	NPC32714
0.8365	Intermediate Similarity	NPC274678
0.8365	Intermediate Similarity	NPC26244
0.8364	Intermediate Similarity	NPC95344
0.8364	Intermediate Similarity	NPC64586
0.8364	Intermediate Similarity	NPC262365
0.8362	Intermediate Similarity	NPC258366
0.8362	Intermediate Similarity	NPC473974
0.8362	Intermediate Similarity	NPC79933
0.8362	Intermediate Similarity	NPC31296
0.8362	Intermediate Similarity	NPC323074
0.835	Intermediate Similarity	NPC162314
0.835	Intermediate Similarity	NPC306884
0.835	Intermediate Similarity	NPC210497
0.835	Intermediate Similarity	NPC94139
0.835	Intermediate Similarity	NPC147284
0.835	Intermediate Similarity	NPC3358
0.8349	Intermediate Similarity	NPC477814
0.8349	Intermediate Similarity	NPC53740
0.8347	Intermediate Similarity	NPC72667
0.8333	Intermediate Similarity	NPC475580
0.8333	Intermediate Similarity	NPC124030
0.8333	Intermediate Similarity	NPC192
0.8333	Intermediate Similarity	NPC272029
0.8333	Intermediate Similarity	NPC84999
0.8333	Intermediate Similarity	NPC137750
0.8333	Intermediate Similarity	NPC474486
0.8333	Intermediate Similarity	NPC254965
0.8333	Intermediate Similarity	NPC246760
0.8333	Intermediate Similarity	NPC327811
0.8333	Intermediate Similarity	NPC87985
0.8319	Intermediate Similarity	NPC117846
0.8319	Intermediate Similarity	NPC263753
0.8319	Intermediate Similarity	NPC53567
0.8319	Intermediate Similarity	NPC321589
0.8318	Intermediate Similarity	NPC12221
0.8305	Intermediate Similarity	NPC77569
0.8305	Intermediate Similarity	NPC142198
0.8304	Intermediate Similarity	NPC469912
0.8302	Intermediate Similarity	NPC128723
0.8291	Intermediate Similarity	NPC478121
0.8291	Intermediate Similarity	NPC475245
0.8288	Intermediate Similarity	NPC228343
0.8288	Intermediate Similarity	NPC254833
0.8286	Intermediate Similarity	NPC202986
0.8273	Intermediate Similarity	NPC472980
0.8269	Intermediate Similarity	NPC151715

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 NPC13482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	990
0.2-0.3	1126
0.3-0.4	2918
0.4-0.5	1999
0.5-0.6	1246
0.6-0.7	391
0.7-0.8	96
0.8-0.85	23
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8725	High Similarity	NPD1809	Phase 2
0.8654	High Similarity	NPD3020	Approved
0.8627	High Similarity	NPD1432	Clinical (unspecified phase)
0.8611	High Similarity	NPD2342	Discontinued
0.8609	High Similarity	NPD2932	Approved
0.8596	High Similarity	NPD3091	Approved
0.8559	High Similarity	NPD7635	Approved
0.8529	High Similarity	NPD845	Approved
0.8462	Intermediate Similarity	NPD288	Approved
0.8448	Intermediate Similarity	NPD4059	Approved
0.8448	Intermediate Similarity	NPD3019	Approved
0.8396	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD2859	Approved
0.8365	Intermediate Similarity	NPD844	Approved
0.8365	Intermediate Similarity	NPD2860	Approved
0.8305	Intermediate Similarity	NPD3092	Approved
0.8288	Intermediate Similarity	NPD3021	Approved
0.8288	Intermediate Similarity	NPD3022	Approved
0.8269	Intermediate Similarity	NPD2933	Approved
0.8269	Intermediate Similarity	NPD2934	Approved
0.8205	Intermediate Similarity	NPD4093	Discontinued
0.8167	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD3095	Discontinued
0.8136	Intermediate Similarity	NPD1751	Approved
0.8125	Intermediate Similarity	NPD4750	Phase 3
0.8033	Intermediate Similarity	NPD3094	Phase 2
0.7983	Intermediate Similarity	NPD4589	Approved
0.7965	Intermediate Similarity	NPD1792	Phase 2
0.7903	Intermediate Similarity	NPD5736	Approved
0.7903	Intermediate Similarity	NPD3637	Approved
0.7903	Intermediate Similarity	NPD3636	Approved
0.7903	Intermediate Similarity	NPD3635	Approved
0.784	Intermediate Similarity	NPD2606	Approved
0.784	Intermediate Similarity	NPD2605	Approved
0.7833	Intermediate Similarity	NPD2286	Discontinued
0.7826	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2194	Approved
0.7823	Intermediate Similarity	NPD2195	Approved
0.7818	Intermediate Similarity	NPD940	Approved
0.7818	Intermediate Similarity	NPD846	Approved
0.7815	Intermediate Similarity	NPD5303	Approved
0.7815	Intermediate Similarity	NPD5304	Approved
0.7778	Intermediate Similarity	NPD5155	Approved
0.7778	Intermediate Similarity	NPD5156	Approved
0.7769	Intermediate Similarity	NPD3023	Approved
0.7769	Intermediate Similarity	NPD3026	Approved
0.7752	Intermediate Similarity	NPD4097	Suspended
0.775	Intermediate Similarity	NPD3025	Approved
0.775	Intermediate Similarity	NPD3024	Approved
0.7745	Intermediate Similarity	NPD111	Approved
0.7699	Intermediate Similarity	NPD1445	Approved
0.7699	Intermediate Similarity	NPD1444	Approved
0.7698	Intermediate Similarity	NPD3595	Approved
0.7698	Intermediate Similarity	NPD3594	Approved
0.7692	Intermediate Similarity	NPD2228	Approved
0.7692	Intermediate Similarity	NPD2234	Approved
0.7692	Intermediate Similarity	NPD2229	Approved
0.7692	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD4626	Approved
0.768	Intermediate Similarity	NPD4624	Approved
0.7667	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD6663	Approved
0.7647	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4060	Phase 1
0.7568	Intermediate Similarity	NPD1242	Phase 1
0.7561	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4625	Phase 3
0.7479	Intermediate Similarity	NPD497	Approved
0.7462	Intermediate Similarity	NPD3620	Phase 2
0.7462	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5327	Phase 3
0.7434	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1201	Approved
0.7417	Intermediate Similarity	NPD6671	Approved
0.7402	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD498	Approved
0.7395	Intermediate Similarity	NPD496	Approved
0.7395	Intermediate Similarity	NPD495	Approved
0.7381	Intermediate Similarity	NPD6696	Suspended
0.7377	Intermediate Similarity	NPD7330	Discontinued
0.7368	Intermediate Similarity	NPD7743	Approved
0.7368	Intermediate Similarity	NPD7742	Approved
0.7344	Intermediate Similarity	NPD2861	Phase 2
0.7333	Intermediate Similarity	NPD1793	Approved
0.7333	Intermediate Similarity	NPD1791	Approved
0.7328	Intermediate Similarity	NPD4140	Approved
0.7317	Intermediate Similarity	NPD5691	Approved
0.7317	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4749	Approved
0.7281	Intermediate Similarity	NPD9500	Approved
0.7273	Intermediate Similarity	NPD5735	Approved
0.7259	Intermediate Similarity	NPD4725	Approved
0.7259	Intermediate Similarity	NPD4721	Approved
0.7259	Intermediate Similarity	NPD4726	Approved
0.7257	Intermediate Similarity	NPD3028	Approved
0.725	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5283	Phase 1
0.7244	Intermediate Similarity	NPD1283	Approved
0.7239	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2230	Approved
0.7222	Intermediate Similarity	NPD2233	Approved
0.7222	Intermediate Similarity	NPD2232	Approved
0.7218	Intermediate Similarity	NPD6353	Approved
0.7213	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7636	Approved
0.7213	Intermediate Similarity	NPD7340	Approved
0.72	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3143	Discontinued
0.7188	Intermediate Similarity	NPD1470	Approved
0.7177	Intermediate Similarity	NPD1651	Approved
0.7165	Intermediate Similarity	NPD1669	Approved
0.7154	Intermediate Similarity	NPD4908	Phase 1
0.7153	Intermediate Similarity	NPD3638	Discontinued
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7131	Intermediate Similarity	NPD709	Approved
0.712	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD8651	Approved
0.7107	Intermediate Similarity	NPD1398	Phase 1
0.7101	Intermediate Similarity	NPD7003	Approved
0.7101	Intermediate Similarity	NPD8166	Discontinued
0.7087	Intermediate Similarity	NPD3070	Discontinued
0.7083	Intermediate Similarity	NPD228	Approved
0.7071	Intermediate Similarity	NPD7041	Phase 2
0.7071	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD9608	Approved
0.7069	Intermediate Similarity	NPD9610	Approved
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.705	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1281	Approved
0.7	Intermediate Similarity	NPD6584	Phase 3
0.6992	Remote Similarity	NPD8032	Phase 2
0.6992	Remote Similarity	NPD7157	Approved
0.6985	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2668	Approved
0.6984	Remote Similarity	NPD2667	Approved
0.697	Remote Similarity	NPD7095	Approved
0.6963	Remote Similarity	NPD2157	Approved
0.6957	Remote Similarity	NPD4256	Phase 2
0.6957	Remote Similarity	NPD4257	Approved
0.695	Remote Similarity	NPD2421	Approved
0.695	Remote Similarity	NPD2420	Approved
0.6947	Remote Similarity	NPD4208	Discontinued
0.694	Remote Similarity	NPD3110	Approved
0.694	Remote Similarity	NPD3109	Approved
0.694	Remote Similarity	NPD6346	Approved
0.6934	Remote Similarity	NPD6099	Approved
0.6934	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD1164	Approved
0.6917	Remote Similarity	NPD5451	Approved
0.6911	Remote Similarity	NPD5951	Approved
0.6906	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1755	Approved
0.6899	Remote Similarity	NPD4659	Approved
0.6885	Remote Similarity	NPD9379	Approved
0.6885	Remote Similarity	NPD9377	Approved
0.6884	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1611	Approved
0.6861	Remote Similarity	NPD4108	Discontinued
0.6855	Remote Similarity	NPD6387	Discontinued
0.6838	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7037	Approved
0.6833	Remote Similarity	NPD2684	Approved
0.6831	Remote Similarity	NPD7390	Discontinued
0.6825	Remote Similarity	NPD7741	Discontinued
0.6825	Remote Similarity	NPD1548	Phase 1
0.6818	Remote Similarity	NPD4212	Discontinued
0.6815	Remote Similarity	NPD2238	Phase 2
0.6812	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2935	Discontinued
0.6797	Remote Similarity	NPD1983	Approved
0.6797	Remote Similarity	NPD1981	Approved
0.6797	Remote Similarity	NPD1980	Approved
0.6794	Remote Similarity	NPD2797	Approved
0.6794	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3053	Approved
0.6794	Remote Similarity	NPD4103	Phase 2
0.6794	Remote Similarity	NPD3055	Approved
0.6791	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2209	Approved
0.6786	Remote Similarity	NPD2211	Approved
0.6783	Remote Similarity	NPD9273	Approved
0.6783	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3645	Discontinued
0.6774	Remote Similarity	NPD475	Phase 2
0.6772	Remote Similarity	NPD3445	Approved
0.6772	Remote Similarity	NPD3443	Approved
0.6772	Remote Similarity	NPD3444	Approved
0.6769	Remote Similarity	NPD6583	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data