NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	2.161
LogD:	2.491
LogS:	-3.277
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	4.539
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.669
MDCK Permeability:	3.5563531127991155e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.971
20% Bioavailability (F20%):	0.387
30% Bioavailability (F30%):	0.707

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.849
Plasma Protein Binding (PPB):	88.2762222290039%
Volume Distribution (VD):	0.501
Pgp-substrate:	9.360420227050781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.411
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.335
CYP2C19-substrate:	0.204
CYP2C9-inhibitor:	0.285
CYP2C9-substrate:	0.541
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.356
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	9.683
Half-life (T1/2):	0.694

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.331
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.737
Maximum Recommended Daily Dose:	0.513
Skin Sensitization:	0.737
Carcinogencity:	0.093
Eye Corrosion:	0.733
Eye Irritation:	0.399
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC167881

Natural Product ID:	NPC167881
*Common Name:**	Neobritannilactone B
IUPAC Name:	(3aR,4S,6E,10E,11aS)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
Synonyms:	neobritannilactone B
Standard InCHIKey:	PDEJECFRCJOMEN-RZPRNJIHSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13-,14+/m0/s1
SMILES:	C/C/1=C[C@@H]2OC(=O)C(=C)[C@@H]2[C@H](C/C(=C/CC1)/C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503702
PubChem CID:	11528898
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643020]
NPO3908	Eupatorium formosanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29832	Eupatorium cuneifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8594	Eupatorium glaucescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3908	Eupatorium formosanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29832	Eupatorium cuneifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3908	Eupatorium formosanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3908	Eupatorium formosanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8594	Eupatorium glaucescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17782	Inula britannica	Species	Asteraceae	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
IC50	4
Others	20

Activity Type	# Activity
Cell Line	24

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	14300.0	nM	PMID[529655]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	56100.0	nM	PMID[529655]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	27400.0	nM	PMID[529655]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	21400.0	nM	PMID[529655]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	10.73	%	PMID[529655]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	14.12	%	PMID[529655]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	41.62	%	PMID[529655]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	89.11	%	PMID[529655]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	96.81	%	PMID[529655]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	13.58	%	PMID[529655]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	24.46	%	PMID[529655]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	66.54	%	PMID[529655]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	82.27	%	PMID[529655]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	87.02	%	PMID[529655]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	9.82	%	PMID[529655]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	21.93	%	PMID[529655]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	77.57	%	PMID[529655]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	96.94	%	PMID[529655]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	98.29	%	PMID[529655]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	9.55	%	PMID[529655]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	8.66	%	PMID[529655]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	11.78	%	PMID[529655]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	15.95	%	PMID[529655]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	19.22	%	PMID[529655]

☑ 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 NPC167881 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	161
0.1-0.2	1146
0.2-0.3	5404
0.3-0.4	14680
0.4-0.5	10868
0.5-0.6	6743
0.6-0.7	2824
0.7-0.8	688
0.8-0.85	80
0.85-0.9	47
0.9-0.95	50
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC98557
0.9733	High Similarity	NPC24417
0.9605	High Similarity	NPC229825
0.9595	High Similarity	NPC471465
0.9595	High Similarity	NPC196653
0.9481	High Similarity	NPC59097
0.9481	High Similarity	NPC40746
0.9481	High Similarity	NPC473390
0.9481	High Similarity	NPC169575
0.9481	High Similarity	NPC131669
0.9359	High Similarity	NPC96259
0.9359	High Similarity	NPC141193
0.9359	High Similarity	NPC158756
0.9359	High Similarity	NPC476804
0.9359	High Similarity	NPC191476
0.9359	High Similarity	NPC114979
0.9241	High Similarity	NPC255307
0.9241	High Similarity	NPC470755
0.9221	High Similarity	NPC52861
0.92	High Similarity	NPC320630
0.92	High Similarity	NPC141789
0.92	High Similarity	NPC116177
0.92	High Similarity	NPC476028
0.92	High Similarity	NPC7563
0.92	High Similarity	NPC171204
0.9178	High Similarity	NPC295633
0.9178	High Similarity	NPC269206
0.9178	High Similarity	NPC58956
0.9125	High Similarity	NPC475461
0.9125	High Similarity	NPC469910
0.9125	High Similarity	NPC305475
0.9067	High Similarity	NPC68819
0.8961	High Similarity	NPC270126
0.8902	High Similarity	NPC473715
0.8902	High Similarity	NPC476805
0.8902	High Similarity	NPC476803
0.8902	High Similarity	NPC475819
0.8889	High Similarity	NPC150755
0.8846	High Similarity	NPC281132
0.8831	High Similarity	NPC108816
0.8831	High Similarity	NPC93763
0.8831	High Similarity	NPC267231
0.8816	High Similarity	NPC235906
0.8784	High Similarity	NPC163003
0.8765	High Similarity	NPC165162
0.875	High Similarity	NPC116543
0.8718	High Similarity	NPC470239
0.8718	High Similarity	NPC89128
0.8718	High Similarity	NPC470244
0.8701	High Similarity	NPC97516
0.869	High Similarity	NPC473619
0.869	High Similarity	NPC469368
0.869	High Similarity	NPC475855
0.869	High Similarity	NPC474232
0.8684	High Similarity	NPC155587
0.8625	High Similarity	NPC89555
0.8588	High Similarity	NPC473321
0.8553	High Similarity	NPC140287
0.8553	High Similarity	NPC476355
0.8533	High Similarity	NPC129665
0.8488	Intermediate Similarity	NPC295204
0.8488	Intermediate Similarity	NPC162205
0.8488	Intermediate Similarity	NPC288240
0.8488	Intermediate Similarity	NPC228451
0.8488	Intermediate Similarity	NPC273579
0.8488	Intermediate Similarity	NPC125674
0.8488	Intermediate Similarity	NPC475302
0.8488	Intermediate Similarity	NPC475838
0.8471	Intermediate Similarity	NPC179394
0.8471	Intermediate Similarity	NPC144133
0.8462	Intermediate Similarity	NPC474760
0.8391	Intermediate Similarity	NPC303942
0.8391	Intermediate Similarity	NPC57405
0.8391	Intermediate Similarity	NPC474247
0.8353	Intermediate Similarity	NPC474032
0.8333	Intermediate Similarity	NPC123360
0.8313	Intermediate Similarity	NPC21469
0.8312	Intermediate Similarity	NPC114727
0.8312	Intermediate Similarity	NPC476590
0.8312	Intermediate Similarity	NPC48641
0.8295	Intermediate Similarity	NPC471142
0.8295	Intermediate Similarity	NPC477922
0.8293	Intermediate Similarity	NPC250315
0.8272	Intermediate Similarity	NPC301477
0.8272	Intermediate Similarity	NPC141810
0.8272	Intermediate Similarity	NPC25684
0.8272	Intermediate Similarity	NPC281949
0.8256	Intermediate Similarity	NPC129419
0.825	Intermediate Similarity	NPC617
0.8235	Intermediate Similarity	NPC477302
0.8235	Intermediate Similarity	NPC136879
0.8228	Intermediate Similarity	NPC41780
0.8228	Intermediate Similarity	NPC187568
0.8228	Intermediate Similarity	NPC65603
0.8214	Intermediate Similarity	NPC50637
0.8205	Intermediate Similarity	NPC193351
0.8205	Intermediate Similarity	NPC138408
0.8205	Intermediate Similarity	NPC226669
0.8202	Intermediate Similarity	NPC477921
0.8202	Intermediate Similarity	NPC306041
0.8202	Intermediate Similarity	NPC230800
0.8202	Intermediate Similarity	NPC473859
0.8202	Intermediate Similarity	NPC279621
0.814	Intermediate Similarity	NPC206001
0.814	Intermediate Similarity	NPC268298
0.814	Intermediate Similarity	NPC218927
0.8118	Intermediate Similarity	NPC266957
0.809	Intermediate Similarity	NPC475659
0.809	Intermediate Similarity	NPC471141
0.8072	Intermediate Similarity	NPC474703
0.8068	Intermediate Similarity	NPC475912
0.8049	Intermediate Similarity	NPC470241
0.8049	Intermediate Similarity	NPC325031
0.8025	Intermediate Similarity	NPC19841
0.8025	Intermediate Similarity	NPC178277
0.8025	Intermediate Similarity	NPC475210
0.8023	Intermediate Similarity	NPC202672
0.8022	Intermediate Similarity	NPC471144
0.8022	Intermediate Similarity	NPC473326
0.8	Intermediate Similarity	NPC470240
0.8	Intermediate Similarity	NPC469483
0.8	Intermediate Similarity	NPC476794
0.8	Intermediate Similarity	NPC194871
0.7976	Intermediate Similarity	NPC156485
0.7976	Intermediate Similarity	NPC82297
0.7975	Intermediate Similarity	NPC329852
0.7955	Intermediate Similarity	NPC184463
0.7955	Intermediate Similarity	NPC30515
0.7955	Intermediate Similarity	NPC131209
0.7952	Intermediate Similarity	NPC474252
0.7935	Intermediate Similarity	NPC475949
0.7935	Intermediate Similarity	NPC288876
0.7931	Intermediate Similarity	NPC166919
0.7931	Intermediate Similarity	NPC295312
0.7922	Intermediate Similarity	NPC67183
0.7907	Intermediate Similarity	NPC160138
0.7895	Intermediate Similarity	NPC470256
0.7889	Intermediate Similarity	NPC14961
0.7889	Intermediate Similarity	NPC36954
0.7889	Intermediate Similarity	NPC52044
0.7889	Intermediate Similarity	NPC270013
0.7889	Intermediate Similarity	NPC304886
0.7882	Intermediate Similarity	NPC261380
0.7882	Intermediate Similarity	NPC50362
0.7882	Intermediate Similarity	NPC38468
0.7882	Intermediate Similarity	NPC319795
0.7865	Intermediate Similarity	NPC469692
0.7865	Intermediate Similarity	NPC179746
0.7865	Intermediate Similarity	NPC212486
0.7865	Intermediate Similarity	NPC476300
0.7865	Intermediate Similarity	NPC81419
0.7865	Intermediate Similarity	NPC469645
0.7848	Intermediate Similarity	NPC472966
0.7841	Intermediate Similarity	NPC51004
0.7831	Intermediate Similarity	NPC471325
0.7816	Intermediate Similarity	NPC277771
0.7816	Intermediate Similarity	NPC287089
0.7805	Intermediate Similarity	NPC182550
0.7805	Intermediate Similarity	NPC63649
0.7805	Intermediate Similarity	NPC264227
0.7805	Intermediate Similarity	NPC472965
0.7802	Intermediate Similarity	NPC476315
0.7792	Intermediate Similarity	NPC476591
0.7792	Intermediate Similarity	NPC88877
0.7791	Intermediate Similarity	NPC107787
0.7791	Intermediate Similarity	NPC261721
0.7778	Intermediate Similarity	NPC323008
0.7778	Intermediate Similarity	NPC474278
0.7778	Intermediate Similarity	NPC262133
0.7778	Intermediate Similarity	NPC470010
0.7778	Intermediate Similarity	NPC474035
0.7778	Intermediate Similarity	NPC121825
0.7778	Intermediate Similarity	NPC470013
0.7778	Intermediate Similarity	NPC477131
0.7778	Intermediate Similarity	NPC57744
0.7778	Intermediate Similarity	NPC474338
0.7778	Intermediate Similarity	NPC81386
0.7766	Intermediate Similarity	NPC471148
0.7765	Intermediate Similarity	NPC165287
0.7765	Intermediate Similarity	NPC159635
0.7765	Intermediate Similarity	NPC115786
0.7753	Intermediate Similarity	NPC261607
0.7753	Intermediate Similarity	NPC208886
0.7753	Intermediate Similarity	NPC300312
0.7753	Intermediate Similarity	NPC233345
0.7753	Intermediate Similarity	NPC186363
0.7753	Intermediate Similarity	NPC111114
0.7753	Intermediate Similarity	NPC12172
0.7753	Intermediate Similarity	NPC133698
0.7738	Intermediate Similarity	NPC85772
0.7738	Intermediate Similarity	NPC173609
0.7738	Intermediate Similarity	NPC474291
0.7727	Intermediate Similarity	NPC151770
0.7727	Intermediate Similarity	NPC307411
0.7717	Intermediate Similarity	NPC161493
0.7711	Intermediate Similarity	NPC276356
0.7711	Intermediate Similarity	NPC302426
0.7701	Intermediate Similarity	NPC178215
0.7701	Intermediate Similarity	NPC237540
0.7692	Intermediate Similarity	NPC213698

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 NPC167881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1710
0.2-0.3	3887
0.3-0.4	2379
0.4-0.5	657
0.5-0.6	303
0.6-0.7	44
0.7-0.8	19
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
0.7882	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6698	Approved
0.7444	Intermediate Similarity	NPD46	Approved
0.7442	Intermediate Similarity	NPD7154	Phase 3
0.7333	Intermediate Similarity	NPD1695	Approved
0.7294	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5785	Approved
0.7079	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5363	Approved
0.7079	Intermediate Similarity	NPD1694	Approved
0.7059	Intermediate Similarity	NPD4268	Approved
0.7059	Intermediate Similarity	NPD4271	Approved
0.7045	Intermediate Similarity	NPD5362	Discontinued
0.7	Intermediate Similarity	NPD4249	Approved
0.6932	Remote Similarity	NPD4270	Approved
0.6932	Remote Similarity	NPD6435	Approved
0.6932	Remote Similarity	NPD4269	Approved
0.6931	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4251	Approved
0.6923	Remote Similarity	NPD4250	Approved
0.6907	Remote Similarity	NPD4225	Approved
0.6897	Remote Similarity	NPD4252	Approved
0.6897	Remote Similarity	NPD4820	Approved
0.6897	Remote Similarity	NPD4821	Approved
0.6897	Remote Similarity	NPD4819	Approved
0.6897	Remote Similarity	NPD4822	Approved
0.6882	Remote Similarity	NPD7838	Discovery
0.6818	Remote Similarity	NPD5369	Approved
0.6813	Remote Similarity	NPD5786	Approved
0.6809	Remote Similarity	NPD7983	Approved
0.6742	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6371	Approved
0.6705	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5779	Approved
0.6562	Remote Similarity	NPD5778	Approved
0.6556	Remote Similarity	NPD5209	Approved
0.6538	Remote Similarity	NPD6686	Approved
0.6512	Remote Similarity	NPD8039	Approved
0.6509	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5332	Approved
0.6484	Remote Similarity	NPD5331	Approved
0.6444	Remote Similarity	NPD4790	Discontinued
0.6421	Remote Similarity	NPD5370	Suspended
0.6421	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6101	Approved
0.6413	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD7839	Suspended
0.6364	Remote Similarity	NPD4756	Discovery
0.6329	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5282	Discontinued
0.6296	Remote Similarity	NPD3197	Phase 1
0.6296	Remote Similarity	NPD6053	Discontinued
0.6289	Remote Similarity	NPD6411	Approved
0.6289	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7638	Approved
0.6216	Remote Similarity	NPD7115	Discovery
0.6176	Remote Similarity	NPD7639	Approved
0.6176	Remote Similarity	NPD7640	Approved
0.6122	Remote Similarity	NPD7637	Suspended
0.6117	Remote Similarity	NPD5344	Discontinued
0.6105	Remote Similarity	NPD6422	Discontinued
0.6071	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3172	Approved
0.6049	Remote Similarity	NPD368	Approved
0.6022	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD6927	Phase 3
0.5981	Remote Similarity	NPD5697	Approved
0.598	Remote Similarity	NPD7902	Approved
0.598	Remote Similarity	NPD6083	Phase 2
0.598	Remote Similarity	NPD6084	Phase 2
0.5974	Remote Similarity	NPD4266	Approved
0.5974	Remote Similarity	NPD3196	Approved
0.5974	Remote Similarity	NPD3195	Phase 2
0.5974	Remote Similarity	NPD3194	Approved
0.5952	Remote Similarity	NPD7331	Phase 2
0.5941	Remote Similarity	NPD5695	Phase 3
0.5938	Remote Similarity	NPD7146	Approved
0.5938	Remote Similarity	NPD7521	Approved
0.5938	Remote Similarity	NPD6684	Approved
0.5938	Remote Similarity	NPD5330	Approved
0.5938	Remote Similarity	NPD3618	Phase 1
0.5938	Remote Similarity	NPD7334	Approved
0.5938	Remote Similarity	NPD6409	Approved
0.5926	Remote Similarity	NPD6881	Approved
0.5926	Remote Similarity	NPD6899	Approved
0.5922	Remote Similarity	NPD5696	Approved
0.5909	Remote Similarity	NPD6650	Approved
0.5909	Remote Similarity	NPD6649	Approved
0.5897	Remote Similarity	NPD342	Phase 1
0.5895	Remote Similarity	NPD3665	Phase 1
0.5895	Remote Similarity	NPD4786	Approved
0.5895	Remote Similarity	NPD3133	Approved
0.5895	Remote Similarity	NPD3666	Approved
0.5888	Remote Similarity	NPD5739	Approved
0.5888	Remote Similarity	NPD7128	Approved
0.5888	Remote Similarity	NPD6675	Approved
0.5888	Remote Similarity	NPD6402	Approved
0.5872	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6014	Approved
0.5872	Remote Similarity	NPD6372	Approved
0.5872	Remote Similarity	NPD6013	Approved
0.5872	Remote Similarity	NPD6012	Approved
0.5872	Remote Similarity	NPD6373	Approved
0.5865	Remote Similarity	NPD6648	Approved
0.5849	Remote Similarity	NPD6647	Phase 2
0.5842	Remote Similarity	NPD7748	Approved
0.5833	Remote Similarity	NPD5701	Approved
0.5818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7102	Approved
0.5818	Remote Similarity	NPD7290	Approved
0.5818	Remote Similarity	NPD6883	Approved
0.5816	Remote Similarity	NPD6903	Approved
0.5816	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7515	Phase 2
0.5789	Remote Similarity	NPD6110	Phase 1
0.5783	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6011	Approved
0.578	Remote Similarity	NPD7320	Approved
0.5773	Remote Similarity	NPD5279	Phase 3
0.5766	Remote Similarity	NPD6869	Approved
0.5766	Remote Similarity	NPD6847	Approved
0.5766	Remote Similarity	NPD2204	Approved
0.5766	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6617	Approved
0.5766	Remote Similarity	NPD8130	Phase 1
0.5765	Remote Similarity	NPD3704	Approved
0.5761	Remote Similarity	NPD3732	Approved
0.575	Remote Similarity	NPD8074	Phase 3
0.5733	Remote Similarity	NPD3173	Approved
0.5728	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4228	Discovery
0.5714	Remote Similarity	NPD6882	Approved
0.5714	Remote Similarity	NPD8297	Approved
0.5686	Remote Similarity	NPD7900	Approved
0.5686	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6421	Discontinued
0.5676	Remote Similarity	NPD2067	Discontinued
0.567	Remote Similarity	NPD1696	Phase 3
0.5657	Remote Similarity	NPD6672	Approved
0.5657	Remote Similarity	NPD5737	Approved
0.5647	Remote Similarity	NPD7341	Phase 2
0.5644	Remote Similarity	NPD5281	Approved
0.5644	Remote Similarity	NPD8034	Phase 2
0.5644	Remote Similarity	NPD6079	Approved
0.5644	Remote Similarity	NPD5693	Phase 1
0.5644	Remote Similarity	NPD5284	Approved
0.5644	Remote Similarity	NPD8035	Phase 2
0.5638	Remote Similarity	NPD4695	Discontinued
0.5631	Remote Similarity	NPD4629	Approved
0.5631	Remote Similarity	NPD5210	Approved
0.563	Remote Similarity	NPD7642	Approved
0.563	Remote Similarity	NPD7829	Approved
0.563	Remote Similarity	NPD7830	Approved
0.5625	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.561	Remote Similarity	NPD3198	Approved
0.5607	Remote Similarity	NPD5211	Phase 2
0.5607	Remote Similarity	NPD7632	Discontinued
0.5603	Remote Similarity	NPD7641	Discontinued
0.56	Remote Similarity	NPD4753	Phase 2
0.56	Remote Similarity	NPD622	Approved
0.56	Remote Similarity	NPD5328	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