NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	458.23
Volume:	475.659
LogP:	4.036
LogD:	3.078
LogS:	-4.046
# Rotatable Bonds:	5
TPSA:	103.04
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.695
Synthetic Accessibility Score:	5.453
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.874
MDCK Permeability:	9.440192116016988e-06
Pgp-inhibitor:	0.03
Pgp-substrate:	0.219
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.481
Plasma Protein Binding (PPB):	93.5473861694336%
Volume Distribution (VD):	1.921
Pgp-substrate:	8.346226692199707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.24
CYP2C9-substrate:	0.159
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.562
CYP3A4-substrate:	0.512

ADMET: Excretion

Clearance (CL):	4.055
Half-life (T1/2):	0.42

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.752
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.334
Skin Sensitization:	0.39
Carcinogencity:	0.096
Eye Corrosion:	0.015
Eye Irritation:	0.017
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC476596

Natural Product ID:	NPC476596
*Common Name:**	Anthoptilide A
IUPAC Name:	[(1S,7S,8Z,12R,13S,14R)-14-acetyloxy-4,9,13,17-tetramethyl-5,15-dioxo-6-oxatricyclo[11.4.0.03,7]heptadeca-3,8,16-trien-12-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	LGEAXFGKCGRSHE-MQQWTTMNSA-N
Standard InCHI:	InChI=1S/C27H34O7/c1-8-15(3)25(30)34-23-10-9-14(2)11-22-19(17(5)26(31)33-22)13-20-16(4)12-21(29)24(27(20,23)7)32-18(6)28/h8,11-12,20,22-24H,9-10,13H2,1-7H3/b14-11-,15-8+/t20-,22-,23+,24-,27-/m0/s1
SMILES:	C/C=C(\C)/C(=O)O[C@@H]1CC/C(=C\[C@H]2C(=C(C(=O)O2)C)C[C@@H]3[C@@]1([C@H](C(=O)C=C3C)OC(=O)C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	21775679
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33618	Anthoptilum cf. kukenthali	Species	Anthoptilidae	Eukaryota	n.a.	at the depth of 267 m from CSIRO RV Southern Surveyor, on the Northwest side of Port Hedland (18.16.6 S, 118.11.2 E), Western Australia	n.a.	PMID[10757710]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	IC50	=	420000	nM	PMID[10757710]

☑ 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 NPC476596 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	232
0.1-0.2	1383
0.2-0.3	5420
0.3-0.4	12951
0.4-0.5	11191
0.5-0.6	6682
0.6-0.7	3992
0.7-0.8	799
0.8-0.85	33
0.85-0.9	10
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9885	High Similarity	NPC476597
0.9885	High Similarity	NPC476598
0.8851	High Similarity	NPC474193
0.8851	High Similarity	NPC12283
0.8791	High Similarity	NPC471818
0.871	High Similarity	NPC148463
0.8636	High Similarity	NPC474703
0.8636	High Similarity	NPC193198
0.8539	High Similarity	NPC474359
0.8462	Intermediate Similarity	NPC476600
0.8444	Intermediate Similarity	NPC189311
0.8427	Intermediate Similarity	NPC222358
0.8409	Intermediate Similarity	NPC471325
0.8391	Intermediate Similarity	NPC471299
0.837	Intermediate Similarity	NPC226863
0.8316	Intermediate Similarity	NPC470697
0.8229	Intermediate Similarity	NPC470978
0.8229	Intermediate Similarity	NPC470974
0.8211	Intermediate Similarity	NPC475657
0.82	Intermediate Similarity	NPC19239
0.82	Intermediate Similarity	NPC474166
0.8182	Intermediate Similarity	NPC472643
0.8182	Intermediate Similarity	NPC473384
0.8182	Intermediate Similarity	NPC178277
0.8163	Intermediate Similarity	NPC222011
0.8152	Intermediate Similarity	NPC220478
0.8132	Intermediate Similarity	NPC30486
0.8132	Intermediate Similarity	NPC149869
0.8111	Intermediate Similarity	NPC178676
0.8111	Intermediate Similarity	NPC200513
0.8105	Intermediate Similarity	NPC473944
0.8085	Intermediate Similarity	NPC73995
0.8085	Intermediate Similarity	NPC5509
0.8068	Intermediate Similarity	NPC471220
0.8068	Intermediate Similarity	NPC128276
0.8065	Intermediate Similarity	NPC312561
0.8061	Intermediate Similarity	NPC69385
0.8058	Intermediate Similarity	NPC476479
0.8046	Intermediate Similarity	NPC27205
0.8043	Intermediate Similarity	NPC110405
0.8041	Intermediate Similarity	NPC295347
0.8039	Intermediate Similarity	NPC472645
0.8022	Intermediate Similarity	NPC22611
0.8021	Intermediate Similarity	NPC139692
0.8	Intermediate Similarity	NPC469595
0.8	Intermediate Similarity	NPC152467
0.8	Intermediate Similarity	NPC232426
0.8	Intermediate Similarity	NPC212679
0.8	Intermediate Similarity	NPC220454
0.8	Intermediate Similarity	NPC281942
0.7979	Intermediate Similarity	NPC215831
0.7978	Intermediate Similarity	NPC270126
0.7959	Intermediate Similarity	NPC184065
0.7955	Intermediate Similarity	NPC57744
0.7955	Intermediate Similarity	NPC187568
0.7955	Intermediate Similarity	NPC41780
0.7941	Intermediate Similarity	NPC189616
0.7938	Intermediate Similarity	NPC477129
0.7938	Intermediate Similarity	NPC477130
0.7935	Intermediate Similarity	NPC31086
0.7935	Intermediate Similarity	NPC475100
0.7935	Intermediate Similarity	NPC159635
0.7917	Intermediate Similarity	NPC141831
0.7912	Intermediate Similarity	NPC471218
0.79	Intermediate Similarity	NPC470761
0.79	Intermediate Similarity	NPC473219
0.79	Intermediate Similarity	NPC476299
0.79	Intermediate Similarity	NPC472644
0.79	Intermediate Similarity	NPC474012
0.7895	Intermediate Similarity	NPC288699
0.7895	Intermediate Similarity	NPC280833
0.7895	Intermediate Similarity	NPC284561
0.7895	Intermediate Similarity	NPC174342
0.7879	Intermediate Similarity	NPC38530
0.7879	Intermediate Similarity	NPC84335
0.7879	Intermediate Similarity	NPC474343
0.7879	Intermediate Similarity	NPC208094
0.7879	Intermediate Similarity	NPC53844
0.7879	Intermediate Similarity	NPC110937
0.7857	Intermediate Similarity	NPC183012
0.7849	Intermediate Similarity	NPC65661
0.7841	Intermediate Similarity	NPC235906
0.7835	Intermediate Similarity	NPC115021
0.7822	Intermediate Similarity	NPC476478
0.7812	Intermediate Similarity	NPC469368
0.7812	Intermediate Similarity	NPC51486
0.7812	Intermediate Similarity	NPC469372
0.781	Intermediate Similarity	NPC475922
0.7802	Intermediate Similarity	NPC301477
0.7802	Intermediate Similarity	NPC25684
0.7802	Intermediate Similarity	NPC281949
0.7802	Intermediate Similarity	NPC42470
0.78	Intermediate Similarity	NPC54843
0.78	Intermediate Similarity	NPC252295
0.7789	Intermediate Similarity	NPC477128
0.7789	Intermediate Similarity	NPC475906
0.7789	Intermediate Similarity	NPC469628
0.7789	Intermediate Similarity	NPC469631
0.7789	Intermediate Similarity	NPC469653
0.7789	Intermediate Similarity	NPC471047
0.7789	Intermediate Similarity	NPC475902
0.7788	Intermediate Similarity	NPC475510
0.7788	Intermediate Similarity	NPC475587
0.7778	Intermediate Similarity	NPC234993
0.7778	Intermediate Similarity	NPC242848
0.7778	Intermediate Similarity	NPC134072
0.7766	Intermediate Similarity	NPC472863
0.7766	Intermediate Similarity	NPC305475
0.7766	Intermediate Similarity	NPC475461
0.7766	Intermediate Similarity	NPC279859
0.7766	Intermediate Similarity	NPC107787
0.7766	Intermediate Similarity	NPC261721
0.7766	Intermediate Similarity	NPC38576
0.7766	Intermediate Similarity	NPC202394
0.7755	Intermediate Similarity	NPC476415
0.7755	Intermediate Similarity	NPC38830
0.7755	Intermediate Similarity	NPC53685
0.7753	Intermediate Similarity	NPC476028
0.7753	Intermediate Similarity	NPC171204
0.7753	Intermediate Similarity	NPC141789
0.7745	Intermediate Similarity	NPC476081
0.7745	Intermediate Similarity	NPC183571
0.7736	Intermediate Similarity	NPC115257
0.7736	Intermediate Similarity	NPC161816
0.7732	Intermediate Similarity	NPC219874
0.7732	Intermediate Similarity	NPC65513
0.7732	Intermediate Similarity	NPC472814
0.7732	Intermediate Similarity	NPC72845
0.7732	Intermediate Similarity	NPC177037
0.7727	Intermediate Similarity	NPC155587
0.7727	Intermediate Similarity	NPC244166
0.7717	Intermediate Similarity	NPC35556
0.7717	Intermediate Similarity	NPC173609
0.7717	Intermediate Similarity	NPC186276
0.7714	Intermediate Similarity	NPC473939
0.7714	Intermediate Similarity	NPC473595
0.7714	Intermediate Similarity	NPC322903
0.7708	Intermediate Similarity	NPC168131
0.7708	Intermediate Similarity	NPC177141
0.7701	Intermediate Similarity	NPC16349
0.7701	Intermediate Similarity	NPC222244
0.77	Intermediate Similarity	NPC2049
0.77	Intermediate Similarity	NPC253826
0.7692	Intermediate Similarity	NPC195424
0.7692	Intermediate Similarity	NPC281132
0.7692	Intermediate Similarity	NPC304795
0.7692	Intermediate Similarity	NPC477125
0.7677	Intermediate Similarity	NPC209355
0.7677	Intermediate Similarity	NPC33473
0.7677	Intermediate Similarity	NPC473369
0.767	Intermediate Similarity	NPC132395
0.767	Intermediate Similarity	NPC474165
0.767	Intermediate Similarity	NPC120321
0.767	Intermediate Similarity	NPC69171
0.767	Intermediate Similarity	NPC471365
0.767	Intermediate Similarity	NPC471364
0.767	Intermediate Similarity	NPC254202
0.7667	Intermediate Similarity	NPC35574
0.766	Intermediate Similarity	NPC106416
0.766	Intermediate Similarity	NPC78089
0.766	Intermediate Similarity	NPC177932
0.766	Intermediate Similarity	NPC86316
0.766	Intermediate Similarity	NPC255307
0.7653	Intermediate Similarity	NPC248193
0.7653	Intermediate Similarity	NPC109414
0.7653	Intermediate Similarity	NPC475302
0.7647	Intermediate Similarity	NPC310981
0.7647	Intermediate Similarity	NPC303559
0.764	Intermediate Similarity	NPC473223
0.764	Intermediate Similarity	NPC123360
0.7634	Intermediate Similarity	NPC118423
0.7634	Intermediate Similarity	NPC475947
0.7629	Intermediate Similarity	NPC8062
0.7629	Intermediate Similarity	NPC101651
0.7629	Intermediate Similarity	NPC161638
0.7629	Intermediate Similarity	NPC159748
0.7624	Intermediate Similarity	NPC478056
0.7624	Intermediate Similarity	NPC264378
0.7624	Intermediate Similarity	NPC176845
0.7619	Intermediate Similarity	NPC91034
0.7619	Intermediate Similarity	NPC475294
0.7614	Intermediate Similarity	NPC474758
0.7614	Intermediate Similarity	NPC294434
0.7614	Intermediate Similarity	NPC476355
0.7614	Intermediate Similarity	NPC117746
0.7614	Intermediate Similarity	NPC140287
0.7614	Intermediate Similarity	NPC259599
0.7614	Intermediate Similarity	NPC15499
0.7609	Intermediate Similarity	NPC282293
0.7609	Intermediate Similarity	NPC141810
0.7609	Intermediate Similarity	NPC475665
0.7604	Intermediate Similarity	NPC472302
0.7604	Intermediate Similarity	NPC477302
0.7604	Intermediate Similarity	NPC241507
0.76	Intermediate Similarity	NPC301596
0.76	Intermediate Similarity	NPC299396
0.76	Intermediate Similarity	NPC307164
0.76	Intermediate Similarity	NPC172998
0.76	Intermediate Similarity	NPC112654
0.76	Intermediate Similarity	NPC202833

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 NPC476596 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	1926
0.2-0.3	3781
0.3-0.4	2171
0.4-0.5	681
0.5-0.6	254
0.6-0.7	115
0.7-0.8	8
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
0.8111	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5737	Approved
0.7789	Intermediate Similarity	NPD6672	Approved
0.766	Intermediate Similarity	NPD1694	Approved
0.7551	Intermediate Similarity	NPD5693	Phase 1
0.7396	Intermediate Similarity	NPD6684	Approved
0.7396	Intermediate Similarity	NPD7334	Approved
0.7396	Intermediate Similarity	NPD7521	Approved
0.7396	Intermediate Similarity	NPD7146	Approved
0.7396	Intermediate Similarity	NPD6409	Approved
0.7396	Intermediate Similarity	NPD5330	Approved
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7347	Intermediate Similarity	NPD6080	Approved
0.7347	Intermediate Similarity	NPD6673	Approved
0.7347	Intermediate Similarity	NPD6904	Approved
0.7327	Intermediate Similarity	NPD5695	Phase 3
0.73	Intermediate Similarity	NPD6399	Phase 3
0.7282	Intermediate Similarity	NPD4225	Approved
0.7282	Intermediate Similarity	NPD5696	Approved
0.7273	Intermediate Similarity	NPD5785	Approved
0.7245	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6903	Approved
0.7228	Intermediate Similarity	NPD7900	Approved
0.7228	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.72	Intermediate Similarity	NPD6050	Approved
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7182	Intermediate Similarity	NPD6649	Approved
0.7182	Intermediate Similarity	NPD6650	Approved
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7157	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6373	Approved
0.7156	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD8039	Approved
0.713	Intermediate Similarity	NPD5697	Approved
0.71	Intermediate Similarity	NPD5692	Phase 3
0.7091	Intermediate Similarity	NPD6883	Approved
0.7091	Intermediate Similarity	NPD7290	Approved
0.7091	Intermediate Similarity	NPD7102	Approved
0.7064	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6686	Approved
0.7059	Intermediate Similarity	NPD7748	Approved
0.7041	Intermediate Similarity	NPD6098	Approved
0.703	Intermediate Similarity	NPD5694	Approved
0.7027	Intermediate Similarity	NPD6847	Approved
0.7027	Intermediate Similarity	NPD6617	Approved
0.7027	Intermediate Similarity	NPD8130	Phase 1
0.7027	Intermediate Similarity	NPD6869	Approved
0.7019	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.6979	Remote Similarity	NPD5209	Approved
0.6972	Remote Similarity	NPD5701	Approved
0.6964	Remote Similarity	NPD8297	Approved
0.6964	Remote Similarity	NPD6882	Approved
0.6952	Remote Similarity	NPD7638	Approved
0.6947	Remote Similarity	NPD4695	Discontinued
0.6939	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6011	Approved
0.6887	Remote Similarity	NPD7640	Approved
0.6887	Remote Similarity	NPD7639	Approved
0.6863	Remote Similarity	NPD7515	Phase 2
0.6837	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3573	Approved
0.6786	Remote Similarity	NPD6371	Approved
0.6768	Remote Similarity	NPD5363	Approved
0.6765	Remote Similarity	NPD46	Approved
0.6765	Remote Similarity	NPD6698	Approved
0.6731	Remote Similarity	NPD5282	Discontinued
0.6727	Remote Similarity	NPD6008	Approved
0.6726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3618	Phase 1
0.67	Remote Similarity	NPD5279	Phase 3
0.6699	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6638	Remote Similarity	NPD6868	Approved
0.6638	Remote Similarity	NPD6274	Approved
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD3667	Approved
0.6632	Remote Similarity	NPD4756	Discovery
0.661	Remote Similarity	NPD7100	Approved
0.661	Remote Similarity	NPD7101	Approved
0.6606	Remote Similarity	NPD5211	Phase 2
0.6604	Remote Similarity	NPD5221	Approved
0.6604	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5222	Approved
0.6604	Remote Similarity	NPD4697	Phase 3
0.6602	Remote Similarity	NPD5207	Approved
0.6574	Remote Similarity	NPD5286	Approved
0.6574	Remote Similarity	NPD5285	Approved
0.6574	Remote Similarity	NPD4696	Approved
0.6569	Remote Similarity	NPD5208	Approved
0.6566	Remote Similarity	NPD7154	Phase 3
0.6562	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5959	Approved
0.6542	Remote Similarity	NPD4755	Approved
0.6542	Remote Similarity	NPD5173	Approved
0.6538	Remote Similarity	NPD6079	Approved
0.6525	Remote Similarity	NPD6335	Approved
0.6522	Remote Similarity	NPD6053	Discontinued
0.6505	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6101	Approved
0.6505	Remote Similarity	NPD5328	Approved
0.65	Remote Similarity	NPD3133	Approved
0.65	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD3665	Phase 1
0.6486	Remote Similarity	NPD5141	Approved
0.6465	Remote Similarity	NPD4270	Approved
0.6465	Remote Similarity	NPD4269	Approved
0.6455	Remote Similarity	NPD5225	Approved
0.6455	Remote Similarity	NPD5224	Approved
0.6455	Remote Similarity	NPD5226	Approved
0.6455	Remote Similarity	NPD4633	Approved
0.6444	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6317	Approved
0.6436	Remote Similarity	NPD5329	Approved
0.6436	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7260	Phase 2
0.6422	Remote Similarity	NPD4700	Approved
0.6417	Remote Similarity	NPD6319	Approved
0.6415	Remote Similarity	NPD6001	Approved
0.64	Remote Similarity	NPD5362	Discontinued
0.6396	Remote Similarity	NPD5175	Approved
0.6396	Remote Similarity	NPD5174	Approved
0.6387	Remote Similarity	NPD6313	Approved
0.6387	Remote Similarity	NPD6314	Approved
0.6381	Remote Similarity	NPD5284	Approved
0.6381	Remote Similarity	NPD5281	Approved
0.6373	Remote Similarity	NPD5786	Approved
0.6373	Remote Similarity	NPD5690	Phase 2
0.6364	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD6908	Approved
0.6364	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD5369	Approved
0.6341	Remote Similarity	NPD7492	Approved
0.6337	Remote Similarity	NPD4197	Approved
0.6333	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4632	Approved
0.6306	Remote Similarity	NPD7632	Discontinued
0.6303	Remote Similarity	NPD6009	Approved
0.63	Remote Similarity	NPD6435	Approved
0.6296	Remote Similarity	NPD7732	Phase 3
0.629	Remote Similarity	NPD6616	Approved
0.6286	Remote Similarity	NPD7838	Discovery
0.6281	Remote Similarity	NPD6054	Approved
0.6275	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6648	Approved
0.6263	Remote Similarity	NPD4252	Approved
0.6263	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8328	Phase 3
0.626	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD6052	Approved
0.624	Remote Similarity	NPD7078	Approved
0.623	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5983	Phase 2
0.6228	Remote Similarity	NPD6412	Phase 2
0.6226	Remote Similarity	NPD8034	Phase 2
0.6226	Remote Similarity	NPD7637	Suspended
0.6226	Remote Similarity	NPD8035	Phase 2
0.6224	Remote Similarity	NPD3617	Approved
0.6222	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5344	Discontinued
0.6214	Remote Similarity	NPD4623	Approved
0.6214	Remote Similarity	NPD4519	Discontinued
0.6214	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4694	Approved
0.6214	Remote Similarity	NPD5280	Approved
0.6207	Remote Similarity	NPD2067	Discontinued
0.619	Remote Similarity	NPD7736	Approved
0.6179	Remote Similarity	NPD6370	Approved
0.6174	Remote Similarity	NPD5128	Approved
0.6174	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4730	Approved
0.6174	Remote Similarity	NPD4729	Approved
0.617	Remote Similarity	NPD4691	Approved
0.6168	Remote Similarity	NPD4202	Approved
0.616	Remote Similarity	NPD7507	Approved
0.616	Remote Similarity	NPD6336	Discontinued

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