NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.16
Volume:	304.533
LogP:	4.533
LogD:	3.95
LogS:	-4.137
# Rotatable Bonds:	3
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	3.637
Fsp3:	0.389
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:	-4.671
MDCK Permeability:	1.548546424601227e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	96.1351547241211%
Volume Distribution (VD):	0.192
Pgp-substrate:	3.5652358531951904%

ADMET: Metabolism

CYP1A2-inhibitor:	0.65
CYP1A2-substrate:	0.354
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.479
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	1.116
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.815
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.787
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.943
Carcinogencity:	0.823
Eye Corrosion:	0.412
Eye Irritation:	0.976
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC26224

Natural Product ID:	NPC26224
*Common Name:**	Tanzawaic Acid A
IUPAC Name:	(2E,4E)-5-[(6S,8R)-2,6,8-trimethyl-5,6,7,8-tetrahydronaphthalen-1-yl]penta-2,4-dienoic acid
Synonyms:
Standard InCHIKey:	GCHCATJQYLAKIS-UFSSINQASA-N
Standard InCHI:	InChI=1S/C18H22O2/c1-12-10-14(3)18-15(11-12)9-8-13(2)16(18)6-4-5-7-17(19)20/h4-9,12,14H,10-11H2,1-3H3,(H,19,20)/b6-4+,7-5+/t12-,14+/m0/s1
SMILES:	C[C@H]1C[C@@H](C)c2c(C1)ccc(c2/C=C/C=C/C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353035
PubChem CID:	9970370
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO33154	penicillium sp. sf-6013	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453820]

☑ 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

Activity Type	# Activity
Cell Line	5
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	8200.0	nM	PMID[514276]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	21900.0	nM	PMID[514276]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15700.0	nM	PMID[514276]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	17500.0	nM	PMID[514276]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	7100.0	nM	PMID[514276]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	27000.0	nM	PMID[514276]

☑ 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 NPC26224 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	190
0.1-0.2	1642
0.2-0.3	3696
0.3-0.4	14135
0.4-0.5	16449
0.5-0.6	5370
0.6-0.7	1017
0.7-0.8	185
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC472221
0.875	High Similarity	NPC472222
0.8621	High Similarity	NPC267704
0.8571	High Similarity	NPC50192
0.8511	High Similarity	NPC251579
0.8511	High Similarity	NPC133135
0.8488	Intermediate Similarity	NPC242628
0.837	Intermediate Similarity	NPC475059
0.837	Intermediate Similarity	NPC475023
0.828	Intermediate Similarity	NPC475057
0.8235	Intermediate Similarity	NPC133308
0.8214	Intermediate Similarity	NPC32203
0.8214	Intermediate Similarity	NPC206800
0.7981	Intermediate Similarity	NPC66208
0.7976	Intermediate Similarity	NPC54269
0.7895	Intermediate Similarity	NPC153885
0.7879	Intermediate Similarity	NPC133809
0.7879	Intermediate Similarity	NPC128248
0.7879	Intermediate Similarity	NPC136810
0.7879	Intermediate Similarity	NPC225079
0.7879	Intermediate Similarity	NPC469481
0.7812	Intermediate Similarity	NPC238219
0.7789	Intermediate Similarity	NPC133461
0.7757	Intermediate Similarity	NPC186933
0.7755	Intermediate Similarity	NPC239185
0.7755	Intermediate Similarity	NPC226041
0.7732	Intermediate Similarity	NPC260233
0.7714	Intermediate Similarity	NPC475002
0.7714	Intermediate Similarity	NPC95126
0.7708	Intermediate Similarity	NPC323420
0.7708	Intermediate Similarity	NPC155232
0.7692	Intermediate Similarity	NPC243289
0.7692	Intermediate Similarity	NPC208183
0.7692	Intermediate Similarity	NPC318327
0.7677	Intermediate Similarity	NPC134882
0.7677	Intermediate Similarity	NPC49994
0.7667	Intermediate Similarity	NPC303245
0.7653	Intermediate Similarity	NPC219573
0.7653	Intermediate Similarity	NPC185208
0.7647	Intermediate Similarity	NPC329282
0.7614	Intermediate Similarity	NPC287790
0.7614	Intermediate Similarity	NPC3190
0.7614	Intermediate Similarity	NPC3672
0.7614	Intermediate Similarity	NPC249018
0.76	Intermediate Similarity	NPC221825
0.7579	Intermediate Similarity	NPC298115
0.7576	Intermediate Similarity	NPC265220
0.757	Intermediate Similarity	NPC93287
0.7549	Intermediate Similarity	NPC247976
0.7527	Intermediate Similarity	NPC123476
0.7526	Intermediate Similarity	NPC59677
0.7526	Intermediate Similarity	NPC188844
0.7526	Intermediate Similarity	NPC1682
0.7525	Intermediate Similarity	NPC476993
0.7525	Intermediate Similarity	NPC109514
0.75	Intermediate Similarity	NPC471721
0.75	Intermediate Similarity	NPC142326
0.75	Intermediate Similarity	NPC94751
0.75	Intermediate Similarity	NPC75724
0.75	Intermediate Similarity	NPC277277
0.75	Intermediate Similarity	NPC173413
0.7453	Intermediate Similarity	NPC273837
0.7451	Intermediate Similarity	NPC304873
0.7449	Intermediate Similarity	NPC289883
0.7447	Intermediate Similarity	NPC160339
0.7447	Intermediate Similarity	NPC307
0.7444	Intermediate Similarity	NPC78517
0.7444	Intermediate Similarity	NPC159661
0.7444	Intermediate Similarity	NPC167577
0.7442	Intermediate Similarity	NPC1008
0.7442	Intermediate Similarity	NPC226999
0.7442	Intermediate Similarity	NPC158028
0.7442	Intermediate Similarity	NPC135433
0.7442	Intermediate Similarity	NPC87099
0.7442	Intermediate Similarity	NPC280135
0.7442	Intermediate Similarity	NPC39799
0.7442	Intermediate Similarity	NPC193578
0.7429	Intermediate Similarity	NPC21929
0.7423	Intermediate Similarity	NPC284475
0.7423	Intermediate Similarity	NPC125226
0.7423	Intermediate Similarity	NPC220596
0.7419	Intermediate Similarity	NPC44546
0.7404	Intermediate Similarity	NPC105899
0.7383	Intermediate Similarity	NPC474057
0.7381	Intermediate Similarity	NPC6107
0.7379	Intermediate Similarity	NPC19856
0.7379	Intermediate Similarity	NPC255676
0.7379	Intermediate Similarity	NPC329556
0.7368	Intermediate Similarity	NPC69057
0.7368	Intermediate Similarity	NPC269923
0.7368	Intermediate Similarity	NPC167323
0.7363	Intermediate Similarity	NPC285716
0.7363	Intermediate Similarity	NPC17408
0.7358	Intermediate Similarity	NPC475006
0.7347	Intermediate Similarity	NPC314690
0.734	Intermediate Similarity	NPC53299
0.7333	Intermediate Similarity	NPC176228
0.7333	Intermediate Similarity	NPC100767
0.7327	Intermediate Similarity	NPC229242
0.7327	Intermediate Similarity	NPC120393
0.7327	Intermediate Similarity	NPC179411
0.7327	Intermediate Similarity	NPC154517
0.732	Intermediate Similarity	NPC86670
0.732	Intermediate Similarity	NPC70940
0.732	Intermediate Similarity	NPC240108
0.732	Intermediate Similarity	NPC274455
0.732	Intermediate Similarity	NPC213156
0.7315	Intermediate Similarity	NPC280789
0.73	Intermediate Similarity	NPC469893
0.7297	Intermediate Similarity	NPC470820
0.7297	Intermediate Similarity	NPC242764
0.7297	Intermediate Similarity	NPC105141
0.7297	Intermediate Similarity	NPC212891
0.7292	Intermediate Similarity	NPC157778
0.7292	Intermediate Similarity	NPC153308
0.7283	Intermediate Similarity	NPC71795
0.7283	Intermediate Similarity	NPC89950
0.7273	Intermediate Similarity	NPC221275
0.7273	Intermediate Similarity	NPC93181
0.7262	Intermediate Similarity	NPC113837
0.7262	Intermediate Similarity	NPC289915
0.7255	Intermediate Similarity	NPC80115
0.7255	Intermediate Similarity	NPC217621
0.7248	Intermediate Similarity	NPC206414
0.7248	Intermediate Similarity	NPC287055
0.7248	Intermediate Similarity	NPC306977
0.7248	Intermediate Similarity	NPC242957
0.7245	Intermediate Similarity	NPC103346
0.7241	Intermediate Similarity	NPC85511
0.7241	Intermediate Similarity	NPC155429
0.7238	Intermediate Similarity	NPC243677
0.7228	Intermediate Similarity	NPC469890
0.7228	Intermediate Similarity	NPC469891
0.7228	Intermediate Similarity	NPC469892
0.7222	Intermediate Similarity	NPC179726
0.7222	Intermediate Similarity	NPC265513
0.7209	Intermediate Similarity	NPC246822
0.7209	Intermediate Similarity	NPC213570
0.7209	Intermediate Similarity	NPC139416
0.7204	Intermediate Similarity	NPC99240
0.72	Intermediate Similarity	NPC172925
0.7196	Intermediate Similarity	NPC470039
0.7191	Intermediate Similarity	NPC307195
0.7188	Intermediate Similarity	NPC43945
0.7184	Intermediate Similarity	NPC264728
0.7174	Intermediate Similarity	NPC315216
0.7172	Intermediate Similarity	NPC128645
0.717	Intermediate Similarity	NPC37914
0.7158	Intermediate Similarity	NPC475710
0.7157	Intermediate Similarity	NPC135951
0.7156	Intermediate Similarity	NPC471188
0.7143	Intermediate Similarity	NPC198023
0.7143	Intermediate Similarity	NPC158157
0.7143	Intermediate Similarity	NPC19256
0.7143	Intermediate Similarity	NPC103488
0.7143	Intermediate Similarity	NPC32312
0.7143	Intermediate Similarity	NPC155172
0.7128	Intermediate Similarity	NPC324835
0.7128	Intermediate Similarity	NPC44830
0.7128	Intermediate Similarity	NPC308619
0.7128	Intermediate Similarity	NPC127491
0.7126	Intermediate Similarity	NPC95289
0.7117	Intermediate Similarity	NPC217111
0.7117	Intermediate Similarity	NPC476357
0.7115	Intermediate Similarity	NPC25458
0.7113	Intermediate Similarity	NPC267262
0.7111	Intermediate Similarity	NPC175393
0.7105	Intermediate Similarity	NPC202015
0.7103	Intermediate Similarity	NPC249811
0.7103	Intermediate Similarity	NPC27252
0.7103	Intermediate Similarity	NPC472979
0.7103	Intermediate Similarity	NPC472980
0.7094	Intermediate Similarity	NPC275145
0.7093	Intermediate Similarity	NPC311343
0.7091	Intermediate Similarity	NPC470253
0.7083	Intermediate Similarity	NPC164526
0.7083	Intermediate Similarity	NPC474211
0.708	Intermediate Similarity	NPC45794
0.7079	Intermediate Similarity	NPC96835
0.7079	Intermediate Similarity	NPC258492
0.7075	Intermediate Similarity	NPC243601
0.7075	Intermediate Similarity	NPC303141
0.7075	Intermediate Similarity	NPC471186
0.7071	Intermediate Similarity	NPC472319
0.7071	Intermediate Similarity	NPC86987
0.7065	Intermediate Similarity	NPC469894
0.7065	Intermediate Similarity	NPC139901
0.7065	Intermediate Similarity	NPC151405
0.7059	Intermediate Similarity	NPC255781
0.7059	Intermediate Similarity	NPC324602
0.7059	Intermediate Similarity	NPC253423
0.7043	Intermediate Similarity	NPC234337
0.7043	Intermediate Similarity	NPC133389
0.7043	Intermediate Similarity	NPC183339
0.7041	Intermediate Similarity	NPC325709
0.7041	Intermediate Similarity	NPC199567
0.7041	Intermediate Similarity	NPC418308
0.7037	Intermediate Similarity	NPC149455
0.7037	Intermediate Similarity	NPC470252
0.7037	Intermediate Similarity	NPC64642

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 NPC26224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1077
0.2-0.3	1430
0.3-0.4	3255
0.4-0.5	2197
0.5-0.6	850
0.6-0.7	138
0.7-0.8	20
0.8-0.85	1
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9326	High Similarity	NPD6049	Phase 2
0.9326	High Similarity	NPD6048	Clinical (unspecified phase)
0.9167	High Similarity	NPD3971	Phase 1
0.8736	High Similarity	NPD5734	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD9716	Approved
0.7778	Intermediate Similarity	NPD2066	Phase 3
0.7757	Intermediate Similarity	NPD5951	Approved
0.7755	Intermediate Similarity	NPD3495	Discontinued
0.7526	Intermediate Similarity	NPD7631	Approved
0.7476	Intermediate Similarity	NPD5909	Discontinued
0.7449	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7609	Phase 3
0.7379	Intermediate Similarity	NPD1930	Approved
0.7379	Intermediate Similarity	NPD1929	Approved
0.7379	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1089	Approved
0.732	Intermediate Similarity	NPD1090	Approved
0.732	Intermediate Similarity	NPD1086	Approved
0.7216	Intermediate Similarity	NPD800	Approved
0.7212	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6647	Phase 2
0.72	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1087	Approved
0.7188	Intermediate Similarity	NPD650	Approved
0.7172	Intermediate Similarity	NPD1088	Approved
0.7157	Intermediate Similarity	NPD5926	Approved
0.7115	Intermediate Similarity	NPD1932	Approved
0.7071	Intermediate Similarity	NPD1239	Approved
0.7064	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1566	Phase 3
0.7059	Intermediate Similarity	NPD1565	Approved
0.7059	Intermediate Similarity	NPD1564	Approved
0.7041	Intermediate Similarity	NPD5346	Phase 2
0.7041	Intermediate Similarity	NPD5347	Phase 2
0.7037	Intermediate Similarity	NPD2329	Discontinued
0.703	Intermediate Similarity	NPD1693	Approved
0.6961	Remote Similarity	NPD1989	Approved
0.6931	Remote Similarity	NPD1563	Approved
0.6897	Remote Similarity	NPD4626	Approved
0.6869	Remote Similarity	NPD689	Discontinued
0.6837	Remote Similarity	NPD4793	Discontinued
0.6837	Remote Similarity	NPD1282	Approved
0.6832	Remote Similarity	NPD1508	Approved
0.68	Remote Similarity	NPD3672	Approved
0.68	Remote Similarity	NPD3673	Approved
0.6786	Remote Similarity	NPD7635	Approved
0.6759	Remote Similarity	NPD5048	Discontinued
0.6748	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7008	Discontinued
0.6737	Remote Similarity	NPD942	Approved
0.6737	Remote Similarity	NPD226	Approved
0.6637	Remote Similarity	NPD6858	Approved
0.6637	Remote Similarity	NPD7094	Approved
0.6635	Remote Similarity	NPD3093	Approved
0.6635	Remote Similarity	NPD2895	Discontinued
0.6635	Remote Similarity	NPD1843	Approved
0.6634	Remote Similarity	NPD9256	Approved
0.6634	Remote Similarity	NPD9258	Approved
0.6632	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD675	Discontinued
0.6607	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3020	Approved
0.6602	Remote Similarity	NPD1202	Approved
0.6602	Remote Similarity	NPD845	Approved
0.66	Remote Similarity	NPD1101	Approved
0.6598	Remote Similarity	NPD9491	Approved
0.6596	Remote Similarity	NPD227	Approved
0.6596	Remote Similarity	NPD225	Approved
0.6579	Remote Similarity	NPD6010	Discontinued
0.6577	Remote Similarity	NPD2182	Approved
0.6574	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4544	Approved
0.6529	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5691	Approved
0.6522	Remote Similarity	NPD2629	Approved
0.6518	Remote Similarity	NPD1317	Discontinued
0.6514	Remote Similarity	NPD164	Approved
0.65	Remote Similarity	NPD5618	Discontinued
0.6496	Remote Similarity	NPD7610	Discontinued
0.6486	Remote Similarity	NPD2342	Discontinued
0.6476	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD2860	Approved
0.6476	Remote Similarity	NPD2859	Approved
0.6471	Remote Similarity	NPD4199	Phase 3
0.6466	Remote Similarity	NPD3317	Approved
0.6466	Remote Similarity	NPD4198	Discontinued
0.646	Remote Similarity	NPD3643	Approved
0.646	Remote Similarity	NPD3642	Approved
0.646	Remote Similarity	NPD3644	Approved
0.646	Remote Similarity	NPD5927	Discontinued
0.6458	Remote Similarity	NPD3903	Approved
0.6458	Remote Similarity	NPD3981	Approved
0.6458	Remote Similarity	NPD3979	Approved
0.6458	Remote Similarity	NPD3904	Approved
0.6441	Remote Similarity	NPD7009	Phase 2
0.6435	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4635	Approved
0.641	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3099	Discontinued
0.64	Remote Similarity	NPD9257	Approved
0.64	Remote Similarity	NPD9259	Approved
0.6381	Remote Similarity	NPD4814	Discontinued
0.6381	Remote Similarity	NPD2934	Approved
0.6381	Remote Similarity	NPD2933	Approved
0.6372	Remote Similarity	NPD5240	Approved
0.6372	Remote Similarity	NPD5237	Approved
0.6372	Remote Similarity	NPD5239	Approved
0.6372	Remote Similarity	NPD5235	Approved
0.6372	Remote Similarity	NPD5236	Approved
0.6371	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1237	Approved
0.6354	Remote Similarity	NPD9490	Approved
0.6349	Remote Similarity	NPD6966	Discovery
0.6341	Remote Similarity	NPD1283	Approved
0.6341	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2932	Approved
0.6333	Remote Similarity	NPD3019	Approved
0.6333	Remote Similarity	NPD2345	Approved
0.6333	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4818	Approved
0.633	Remote Similarity	NPD4817	Approved
0.633	Remote Similarity	NPD2193	Phase 2
0.633	Remote Similarity	NPD2648	Phase 3
0.632	Remote Similarity	NPD5736	Approved
0.6311	Remote Similarity	NPD4878	Approved
0.6296	Remote Similarity	NPD1238	Approved
0.6286	Remote Similarity	NPD1409	Phase 3
0.6286	Remote Similarity	NPD1066	Discontinued
0.6281	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5765	Approved
0.6269	Remote Similarity	NPD7003	Approved
0.6263	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD288	Approved
0.625	Remote Similarity	NPD3134	Approved
0.625	Remote Similarity	NPD6685	Approved
0.6239	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6354	Discontinued
0.6239	Remote Similarity	NPD1616	Discontinued
0.623	Remote Similarity	NPD1281	Approved
0.6224	Remote Similarity	NPD3035	Approved
0.6218	Remote Similarity	NPD6065	Approved
0.6216	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5408	Approved
0.6212	Remote Similarity	NPD5405	Approved
0.6212	Remote Similarity	NPD5406	Approved
0.6212	Remote Similarity	NPD5404	Approved
0.6207	Remote Similarity	NPD4192	Approved
0.6207	Remote Similarity	NPD4194	Approved
0.6207	Remote Similarity	NPD4193	Approved
0.6207	Remote Similarity	NPD5277	Phase 2
0.6207	Remote Similarity	NPD4191	Approved
0.6204	Remote Similarity	NPD9495	Approved
0.6204	Remote Similarity	NPD253	Approved
0.62	Remote Similarity	NPD3429	Approved
0.62	Remote Similarity	NPD3427	Approved
0.6198	Remote Similarity	NPD5306	Approved
0.6198	Remote Similarity	NPD5125	Phase 3
0.6198	Remote Similarity	NPD5126	Approved
0.6198	Remote Similarity	NPD5305	Approved
0.6198	Remote Similarity	NPD5836	Discontinued
0.6182	Remote Similarity	NPD2196	Discontinued
0.6179	Remote Similarity	NPD6637	Approved
0.6179	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3426	Approved
0.6176	Remote Similarity	NPD3428	Approved
0.6174	Remote Similarity	NPD2201	Approved
0.6168	Remote Similarity	NPD844	Approved
0.6168	Remote Similarity	NPD1809	Phase 2
0.6167	Remote Similarity	NPD3091	Approved
0.6167	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4479	Discontinued
0.6162	Remote Similarity	NPD4170	Approved
0.6162	Remote Similarity	NPD4169	Approved
0.6162	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.616	Remote Similarity	NPD2797	Approved
0.6154	Remote Similarity	NPD3598	Phase 3
0.6148	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4879	Approved
0.6147	Remote Similarity	NPD1067	Discontinued
0.6147	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD9294	Approved
0.6132	Remote Similarity	NPD3982	Approved
0.6132	Remote Similarity	NPD2878	Approved
0.6132	Remote Similarity	NPD3980	Approved
0.6132	Remote Similarity	NPD3719	Approved
0.6132	Remote Similarity	NPD3718	Approved
0.6126	Remote Similarity	NPD5103	Approved
0.6126	Remote Similarity	NPD3680	Approved
0.6126	Remote Similarity	NPD3682	Approved
0.6126	Remote Similarity	NPD4231	Approved
0.6126	Remote Similarity	NPD4229	Approved
0.6124	Remote Similarity	NPD6663	Approved
0.6124	Remote Similarity	NPD7961	Discontinued
0.6121	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD9508	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