NPASS Compound

Structure

NPC474527 OpenBabel07101718242D 25 26 0 0 1 0 0 0 0 0999 V2000 -5.0962 -0.8572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9622 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 3.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 -0.8572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9319 -0.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3641 0.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9397 1.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2301 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4397 2.4936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4981 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7660 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4397 2.4936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9397 1.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0962 0.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 0.1428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 0.6428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 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 1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3801 -2.1554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -1.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 17 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 14 2 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 16 4 1 6 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 16 1 1 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	387.78
LogP:	5.951
LogD:	3.924
LogS:	-3.668
# Rotatable Bonds:	6
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	4.862
Fsp3:	0.727
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:	-4.612
MDCK Permeability:	1.710091601125896e-05
Pgp-inhibitor:	0.921
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.228
20% Bioavailability (F20%):	0.374
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.711
Plasma Protein Binding (PPB):	97.60445404052734%
Volume Distribution (VD):	1.588
Pgp-substrate:	3.4575998783111572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.207
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.52
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.437
CYP3A4-substrate:	0.444

ADMET: Excretion

Clearance (CL):	5.395
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.924
Drug-inuced Liver Injury (DILI):	0.842
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.851
Carcinogencity:	0.036
Eye Corrosion:	0.659
Eye Irritation:	0.55
Respiratory Toxicity:	0.089

Download Data

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

Natural Product: NPC474527

Natural Product ID:	NPC474527
*Common Name:**	Isoacetylcoriacenone
IUPAC Name:	[(4E,8R,11R)-5-methyl-8-[(2R)-6-methylhept-5-en-2-yl]-10-oxo-11-bicyclo[7.2.0]undec-4-enyl] acetate
Synonyms:	Isoacetylcoriacenone
Standard InCHIKey:	SOAIWELMVRCOAD-GIAKDNIESA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-14(2)8-6-10-16(4)18-13-12-15(3)9-7-11-19-20(18)21(24)22(19)25-17(5)23/h8-9,16,18-20,22H,6-7,10-13H2,1-5H3/b15-9+/t16-,18-,19?,20?,22-/m1/s1
SMILES:	CC(=CCC[C@H]([C@H]1CC/C(=C/CCC2C1C(=O)[C@@H]2OC(=O)C)/C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470989
PubChem CID:	44584503
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0003677] Alpha-acyloxy carbonyl compounds [CHEMONTID:0003420] Alpha-acyloxy ketones

*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
NPO29273	Dilophus ligulatus	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277314]
NPO29273	Dilophus ligulatus	Species	Dictyotaceae	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
ED50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[488887]
NPT168	Cell Line	P388	Mus musculus	ED50	=	6.0	ug ml-1	PMID[488887]
NPT168	Cell Line	P388	Mus musculus	ED50	>	10.0	ug ml-1	PMID[488887]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	6.82	ug ml-1	PMID[488887]

☑ 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 NPC474527 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	222
0.1-0.2	1903
0.2-0.3	8585
0.3-0.4	16939
0.4-0.5	8004
0.5-0.6	5823
0.6-0.7	1151
0.7-0.8	65
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471726
0.8947	High Similarity	NPC304795
0.863	High Similarity	NPC40327
0.8514	High Similarity	NPC470237
0.8289	Intermediate Similarity	NPC324762
0.8108	Intermediate Similarity	NPC144511
0.8108	Intermediate Similarity	NPC296522
0.8052	Intermediate Similarity	NPC474419
0.7927	Intermediate Similarity	NPC474703
0.7821	Intermediate Similarity	NPC475861
0.7816	Intermediate Similarity	NPC219874
0.7763	Intermediate Similarity	NPC472955
0.7763	Intermediate Similarity	NPC475310
0.775	Intermediate Similarity	NPC321180
0.7711	Intermediate Similarity	NPC222358
0.7692	Intermediate Similarity	NPC472966
0.7683	Intermediate Similarity	NPC286229
0.7654	Intermediate Similarity	NPC471740
0.7654	Intermediate Similarity	NPC276647
0.7654	Intermediate Similarity	NPC622
0.7632	Intermediate Similarity	NPC199557
0.7625	Intermediate Similarity	NPC195785
0.7625	Intermediate Similarity	NPC211279
0.7625	Intermediate Similarity	NPC15975
0.7595	Intermediate Similarity	NPC244166
0.7564	Intermediate Similarity	NPC135703
0.7531	Intermediate Similarity	NPC474341
0.7531	Intermediate Similarity	NPC128276
0.75	Intermediate Similarity	NPC472967
0.75	Intermediate Similarity	NPC266159
0.75	Intermediate Similarity	NPC475989
0.75	Intermediate Similarity	NPC52609
0.75	Intermediate Similarity	NPC1761
0.747	Intermediate Similarity	NPC255580
0.747	Intermediate Similarity	NPC471325
0.747	Intermediate Similarity	NPC39411
0.7442	Intermediate Similarity	NPC202394
0.7442	Intermediate Similarity	NPC38576
0.7442	Intermediate Similarity	NPC279859
0.7439	Intermediate Similarity	NPC469690
0.7436	Intermediate Similarity	NPC129665
0.7412	Intermediate Similarity	NPC474359
0.7407	Intermediate Similarity	NPC470240
0.7407	Intermediate Similarity	NPC107668
0.7407	Intermediate Similarity	NPC476264
0.7407	Intermediate Similarity	NPC476794
0.7407	Intermediate Similarity	NPC476325
0.7407	Intermediate Similarity	NPC57744
0.7407	Intermediate Similarity	NPC65603
0.7403	Intermediate Similarity	NPC477449
0.7403	Intermediate Similarity	NPC477448
0.7375	Intermediate Similarity	NPC138408
0.7375	Intermediate Similarity	NPC226669
0.7375	Intermediate Similarity	NPC155587
0.7375	Intermediate Similarity	NPC193351
0.7356	Intermediate Similarity	NPC471739
0.7349	Intermediate Similarity	NPC103634
0.7342	Intermediate Similarity	NPC472956
0.7342	Intermediate Similarity	NPC92909
0.7342	Intermediate Similarity	NPC107783
0.7333	Intermediate Similarity	NPC476597
0.7333	Intermediate Similarity	NPC476598
0.7326	Intermediate Similarity	NPC472686
0.7326	Intermediate Similarity	NPC290329
0.7317	Intermediate Similarity	NPC35574
0.7303	Intermediate Similarity	NPC471818
0.7294	Intermediate Similarity	NPC475842
0.7294	Intermediate Similarity	NPC108045
0.7294	Intermediate Similarity	NPC475622
0.7284	Intermediate Similarity	NPC226242
0.7284	Intermediate Similarity	NPC110461
0.7284	Intermediate Similarity	NPC61863
0.7284	Intermediate Similarity	NPC12740
0.7284	Intermediate Similarity	NPC472959
0.7284	Intermediate Similarity	NPC235906
0.7262	Intermediate Similarity	NPC25684
0.7262	Intermediate Similarity	NPC470241
0.7262	Intermediate Similarity	NPC475665
0.7262	Intermediate Similarity	NPC42470
0.7262	Intermediate Similarity	NPC474955
0.7262	Intermediate Similarity	NPC281949
0.7262	Intermediate Similarity	NPC301477
0.7253	Intermediate Similarity	NPC476596
0.725	Intermediate Similarity	NPC469643
0.725	Intermediate Similarity	NPC469691
0.725	Intermediate Similarity	NPC167049
0.725	Intermediate Similarity	NPC469641
0.725	Intermediate Similarity	NPC140287
0.725	Intermediate Similarity	NPC474551
0.725	Intermediate Similarity	NPC330016
0.7237	Intermediate Similarity	NPC477982
0.7229	Intermediate Similarity	NPC178277
0.7229	Intermediate Similarity	NPC182550
0.7229	Intermediate Similarity	NPC617
0.7229	Intermediate Similarity	NPC469620
0.7229	Intermediate Similarity	NPC89128
0.7215	Intermediate Similarity	NPC163003
0.7209	Intermediate Similarity	NPC100391
0.7209	Intermediate Similarity	NPC474776
0.7195	Intermediate Similarity	NPC474760
0.7195	Intermediate Similarity	NPC180290
0.7191	Intermediate Similarity	NPC475971
0.7179	Intermediate Similarity	NPC22301
0.7179	Intermediate Similarity	NPC5714
0.7176	Intermediate Similarity	NPC475936
0.7176	Intermediate Similarity	NPC145963
0.7176	Intermediate Similarity	NPC35556
0.716	Intermediate Similarity	NPC469678
0.716	Intermediate Similarity	NPC475771
0.716	Intermediate Similarity	NPC469669
0.7143	Intermediate Similarity	NPC74673
0.7143	Intermediate Similarity	NPC477361
0.7143	Intermediate Similarity	NPC276356
0.7143	Intermediate Similarity	NPC69271
0.7143	Intermediate Similarity	NPC202824
0.7143	Intermediate Similarity	NPC302426
0.7126	Intermediate Similarity	NPC470223
0.7126	Intermediate Similarity	NPC78089
0.7125	Intermediate Similarity	NPC474543
0.7125	Intermediate Similarity	NPC472018
0.7125	Intermediate Similarity	NPC238425
0.7125	Intermediate Similarity	NPC167145
0.7111	Intermediate Similarity	NPC469718
0.7111	Intermediate Similarity	NPC329857
0.7108	Intermediate Similarity	NPC11796
0.7108	Intermediate Similarity	NPC218817
0.7108	Intermediate Similarity	NPC4827
0.7097	Intermediate Similarity	NPC477354
0.7093	Intermediate Similarity	NPC53867
0.7093	Intermediate Similarity	NPC39588
0.7093	Intermediate Similarity	NPC193198
0.7079	Intermediate Similarity	NPC469628
0.7079	Intermediate Similarity	NPC474845
0.7079	Intermediate Similarity	NPC469631
0.7079	Intermediate Similarity	NPC471047
0.7079	Intermediate Similarity	NPC28227
0.7079	Intermediate Similarity	NPC469653
0.7079	Intermediate Similarity	NPC475906
0.7073	Intermediate Similarity	NPC474447
0.7073	Intermediate Similarity	NPC239127
0.7073	Intermediate Similarity	NPC271070
0.7073	Intermediate Similarity	NPC279537
0.7065	Intermediate Similarity	NPC148463
0.7059	Intermediate Similarity	NPC476988
0.7059	Intermediate Similarity	NPC141810
0.7059	Intermediate Similarity	NPC327002
0.7059	Intermediate Similarity	NPC207188
0.7045	Intermediate Similarity	NPC261721
0.7045	Intermediate Similarity	NPC474045
0.7045	Intermediate Similarity	NPC195640
0.7045	Intermediate Similarity	NPC107787
0.7045	Intermediate Similarity	NPC261253
0.7042	Intermediate Similarity	NPC223677
0.7042	Intermediate Similarity	NPC10316
0.7042	Intermediate Similarity	NPC28779
0.7042	Intermediate Similarity	NPC200845
0.7042	Intermediate Similarity	NPC128061
0.7037	Intermediate Similarity	NPC476355
0.7037	Intermediate Similarity	NPC259599
0.7037	Intermediate Similarity	NPC306928
0.7037	Intermediate Similarity	NPC15499
0.7037	Intermediate Similarity	NPC117746
0.7037	Intermediate Similarity	NPC166797
0.7037	Intermediate Similarity	NPC294434
0.7033	Intermediate Similarity	NPC20713
0.7027	Intermediate Similarity	NPC229252
0.7027	Intermediate Similarity	NPC143857
0.7024	Intermediate Similarity	NPC82488
0.7024	Intermediate Similarity	NPC308545
0.7024	Intermediate Similarity	NPC470239
0.7024	Intermediate Similarity	NPC264227
0.7024	Intermediate Similarity	NPC327674
0.7024	Intermediate Similarity	NPC472965
0.7024	Intermediate Similarity	NPC63649
0.7024	Intermediate Similarity	NPC28319
0.7024	Intermediate Similarity	NPC470244
0.7013	Intermediate Similarity	NPC154728
0.7013	Intermediate Similarity	NPC126899
0.7013	Intermediate Similarity	NPC304665
0.7011	Intermediate Similarity	NPC295799
0.7011	Intermediate Similarity	NPC312660
0.7011	Intermediate Similarity	NPC165287
0.7011	Intermediate Similarity	NPC115786
0.7011	Intermediate Similarity	NPC139566
0.7	Intermediate Similarity	NPC477983
0.7	Intermediate Similarity	NPC477981
0.6989	Remote Similarity	NPC470974
0.6989	Remote Similarity	NPC470978
0.6989	Remote Similarity	NPC273197
0.6989	Remote Similarity	NPC234339
0.6988	Remote Similarity	NPC187568
0.6988	Remote Similarity	NPC472300
0.6988	Remote Similarity	NPC41780
0.6988	Remote Similarity	NPC97516
0.6979	Remote Similarity	NPC473384
0.6977	Remote Similarity	NPC240302
0.6977	Remote Similarity	NPC173609
0.6977	Remote Similarity	NPC471326
0.6977	Remote Similarity	NPC89555
0.6977	Remote Similarity	NPC221231

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 NPC474527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	2548
0.2-0.3	3891
0.3-0.4	1735
0.4-0.5	501
0.5-0.6	206
0.6-0.7	48
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7273	Intermediate Similarity	NPD6672	Approved
0.7273	Intermediate Similarity	NPD5737	Approved
0.7059	Intermediate Similarity	NPD5369	Approved
0.7045	Intermediate Similarity	NPD7146	Approved
0.7045	Intermediate Similarity	NPD7334	Approved
0.7045	Intermediate Similarity	NPD6684	Approved
0.7045	Intermediate Similarity	NPD7521	Approved
0.7045	Intermediate Similarity	NPD5330	Approved
0.7045	Intermediate Similarity	NPD6409	Approved
0.7045	Intermediate Similarity	NPD6098	Approved
0.6977	Remote Similarity	NPD6435	Approved
0.6889	Remote Similarity	NPD6903	Approved
0.6889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6904	Approved
0.6813	Remote Similarity	NPD6673	Approved
0.6813	Remote Similarity	NPD6080	Approved
0.6782	Remote Similarity	NPD4269	Approved
0.6782	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD6399	Phase 3
0.6753	Remote Similarity	NPD3197	Phase 1
0.6747	Remote Similarity	NPD8039	Approved
0.6744	Remote Similarity	NPD5368	Approved
0.6742	Remote Similarity	NPD1694	Approved
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7154	Phase 3
0.6705	Remote Similarity	NPD5362	Discontinued
0.6702	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5786	Approved
0.6632	Remote Similarity	NPD5695	Phase 3
0.663	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6101	Approved
0.6598	Remote Similarity	NPD5696	Approved
0.6591	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5692	Phase 3
0.6556	Remote Similarity	NPD5363	Approved
0.6552	Remote Similarity	NPD4252	Approved
0.6526	Remote Similarity	NPD7748	Approved
0.6495	Remote Similarity	NPD7902	Approved
0.6489	Remote Similarity	NPD5693	Phase 1
0.6489	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD5694	Approved
0.6479	Remote Similarity	NPD28	Approved
0.6479	Remote Similarity	NPD29	Approved
0.6456	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1695	Approved
0.6421	Remote Similarity	NPD5779	Approved
0.6421	Remote Similarity	NPD5778	Approved
0.6383	Remote Similarity	NPD5785	Approved
0.6375	Remote Similarity	NPD7331	Phase 2
0.6374	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7128	Approved
0.6373	Remote Similarity	NPD5739	Approved
0.6373	Remote Similarity	NPD6402	Approved
0.6373	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5282	Discontinued
0.6346	Remote Similarity	NPD6372	Approved
0.6346	Remote Similarity	NPD6373	Approved
0.6316	Remote Similarity	NPD7515	Phase 2
0.6304	Remote Similarity	NPD6422	Discontinued
0.6304	Remote Similarity	NPD5279	Phase 3
0.6289	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD6899	Approved
0.6237	Remote Similarity	NPD3573	Approved
0.6226	Remote Similarity	NPD6650	Approved
0.6226	Remote Similarity	NPD6649	Approved
0.6224	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5209	Approved
0.6222	Remote Similarity	NPD3667	Approved
0.6216	Remote Similarity	NPD3194	Approved
0.6216	Remote Similarity	NPD3195	Phase 2
0.6216	Remote Similarity	NPD3196	Approved
0.6216	Remote Similarity	NPD4266	Approved
0.6211	Remote Similarity	NPD6698	Approved
0.6211	Remote Similarity	NPD46	Approved
0.6211	Remote Similarity	NPD5207	Approved
0.6207	Remote Similarity	NPD4756	Discovery
0.618	Remote Similarity	NPD4822	Approved
0.618	Remote Similarity	NPD4695	Discontinued
0.618	Remote Similarity	NPD4819	Approved
0.618	Remote Similarity	NPD4820	Approved
0.618	Remote Similarity	NPD4821	Approved
0.617	Remote Similarity	NPD5208	Approved
0.6154	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5331	Approved
0.6154	Remote Similarity	NPD5697	Approved
0.6146	Remote Similarity	NPD7983	Approved
0.6136	Remote Similarity	NPD4271	Approved
0.6136	Remote Similarity	NPD4268	Approved
0.6132	Remote Similarity	NPD7102	Approved
0.6132	Remote Similarity	NPD7290	Approved
0.6132	Remote Similarity	NPD6883	Approved
0.6129	Remote Similarity	NPD3618	Phase 1
0.6122	Remote Similarity	NPD5654	Approved
0.6111	Remote Similarity	NPD857	Phase 3
0.6111	Remote Similarity	NPD4790	Discontinued
0.6105	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD6109	Phase 1
0.6095	Remote Similarity	NPD6011	Approved
0.6087	Remote Similarity	NPD3133	Approved
0.6087	Remote Similarity	NPD3665	Phase 1
0.6087	Remote Similarity	NPD3666	Approved
0.6087	Remote Similarity	NPD3668	Phase 3
0.6081	Remote Similarity	NPD3172	Approved
0.6075	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6847	Approved
0.6075	Remote Similarity	NPD6617	Approved
0.6075	Remote Similarity	NPD6869	Approved
0.6075	Remote Similarity	NPD8130	Phase 1
0.6056	Remote Similarity	NPD5343	Approved
0.6038	Remote Similarity	NPD6012	Approved
0.6038	Remote Similarity	NPD6014	Approved
0.6038	Remote Similarity	NPD6013	Approved
0.6022	Remote Similarity	NPD5329	Approved
0.602	Remote Similarity	NPD6001	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD5959	Approved
0.6	Remote Similarity	NPD6614	Approved
0.5979	Remote Similarity	NPD8034	Phase 2
0.5979	Remote Similarity	NPD8035	Phase 2
0.5978	Remote Similarity	NPD6110	Phase 1
0.5976	Remote Similarity	NPD3704	Approved
0.5938	Remote Similarity	NPD4753	Phase 2
0.5938	Remote Similarity	NPD5370	Suspended
0.5938	Remote Similarity	NPD5328	Approved
0.5914	Remote Similarity	NPD4197	Approved
0.5905	Remote Similarity	NPD6008	Approved
0.59	Remote Similarity	NPD4697	Phase 3
0.59	Remote Similarity	NPD7839	Suspended
0.5895	Remote Similarity	NPD4250	Approved
0.5895	Remote Similarity	NPD4251	Approved
0.5876	Remote Similarity	NPD3672	Approved
0.5876	Remote Similarity	NPD3673	Approved
0.587	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD2699	Approved
0.5856	Remote Similarity	NPD6868	Approved
0.5851	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6371	Approved
0.5824	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD3198	Approved
0.5816	Remote Similarity	NPD5284	Approved
0.5816	Remote Similarity	NPD5281	Approved
0.5816	Remote Similarity	NPD6079	Approved
0.5816	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5777	Approved
0.5811	Remote Similarity	NPD6927	Phase 3
0.5802	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5210	Approved
0.58	Remote Similarity	NPD4629	Approved
0.5789	Remote Similarity	NPD5690	Phase 2
0.5789	Remote Similarity	NPD4694	Approved
0.5789	Remote Similarity	NPD4249	Approved
0.5789	Remote Similarity	NPD5280	Approved
0.5784	Remote Similarity	NPD7638	Approved
0.578	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3732	Approved
0.5778	Remote Similarity	NPD3617	Approved
0.5775	Remote Similarity	NPD3174	Discontinued
0.5773	Remote Similarity	NPD6051	Approved
0.5758	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6335	Approved
0.575	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5222	Approved
0.5743	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5221	Approved
0.5743	Remote Similarity	NPD7732	Phase 3
0.5732	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD7639	Approved
0.5728	Remote Similarity	NPD7640	Approved
0.5714	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD6052	Approved
0.5714	Remote Similarity	NPD7838	Discovery
0.5702	Remote Similarity	NPD7100	Approved
0.5702	Remote Similarity	NPD7101	Approved
0.5699	Remote Similarity	NPD4223	Phase 3
0.5699	Remote Similarity	NPD4221	Approved
0.5696	Remote Similarity	NPD287	Approved
0.5686	Remote Similarity	NPD5173	Approved
0.5686	Remote Similarity	NPD4755	Approved
0.5664	Remote Similarity	NPD6317	Approved
0.5657	Remote Similarity	NPD7637	Suspended
0.5648	Remote Similarity	NPD6686	Approved
0.5641	Remote Similarity	NPD8328	Phase 3
0.5634	Remote Similarity	NPD6097	Approved
0.5634	Remote Similarity	NPD6096	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