NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	214.14
Volume:	240.571
LogP:	5.16
LogD:	4.448
LogS:	-6.454
# Rotatable Bonds:	0
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	3.143
Fsp3:	0.467
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:	-4.753
MDCK Permeability:	1.84015716513386e-05
Pgp-inhibitor:	0.062
Pgp-substrate:	0.127
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.902
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.48
Plasma Protein Binding (PPB):	98.75577545166016%
Volume Distribution (VD):	3.561
Pgp-substrate:	2.0846328735351562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.673
CYP2C19-substrate:	0.338
CYP2C9-inhibitor:	0.541
CYP2C9-substrate:	0.81
CYP2D6-inhibitor:	0.5
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.45
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	8.55
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.64
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.801
Skin Sensitization:	0.222
Carcinogencity:	0.485
Eye Corrosion:	0.004
Eye Irritation:	0.198
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC324117

Natural Product ID:	NPC324117
*Common Name:**	Farfugin A
IUPAC Name:	3,5,9-trimethyl-6,7,8,9-tetrahydrobenzo[g][1]benzofuran
Synonyms:
Standard InCHIKey:	LBXSOZAXYXJJLL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H18O/c1-9-5-4-6-12-10(2)7-13-11(3)8-16-15(13)14(9)12/h7-9H,4-6H2,1-3H3
SMILES:	CC1CCCC2=C1C3=C(C=C2C)C(=CO3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399793
PubChem CID:	5317316
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17672504]
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18044832]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13228	Farfugium japonicum	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
EC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	10.9	ug.mL-1	PMID[469435]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	13.6	ug.mL-1	PMID[469435]

☑ 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 NPC324117 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	523
0.1-0.2	1849
0.2-0.3	4412
0.3-0.4	12184
0.4-0.5	6268
0.5-0.6	5761
0.6-0.7	9226
0.7-0.8	2392
0.8-0.85	65
0.85-0.9	13
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9695	High Similarity	NPC233707
0.969	High Similarity	NPC209858
0.9197	High Similarity	NPC158871
0.913	High Similarity	NPC290038
0.9015	High Similarity	NPC279596
0.8873	High Similarity	NPC95526
0.8837	High Similarity	NPC178382
0.8811	High Similarity	NPC472298
0.8788	High Similarity	NPC59502
0.8779	High Similarity	NPC474737
0.8667	High Similarity	NPC183103
0.863	High Similarity	NPC44606
0.8531	High Similarity	NPC478166
0.8521	High Similarity	NPC117674
0.8507	High Similarity	NPC50583
0.8504	High Similarity	NPC59035
0.8504	High Similarity	NPC79202
0.8503	High Similarity	NPC10429
0.8472	Intermediate Similarity	NPC281398
0.8462	Intermediate Similarity	NPC93241
0.8462	Intermediate Similarity	NPC27798
0.8462	Intermediate Similarity	NPC97566
0.8462	Intermediate Similarity	NPC114513
0.8462	Intermediate Similarity	NPC245522
0.8456	Intermediate Similarity	NPC164295
0.8456	Intermediate Similarity	NPC239134
0.8435	Intermediate Similarity	NPC115869
0.8421	Intermediate Similarity	NPC470858
0.8417	Intermediate Similarity	NPC307401
0.8406	Intermediate Similarity	NPC265793
0.8385	Intermediate Similarity	NPC246214
0.8372	Intermediate Similarity	NPC206007
0.8367	Intermediate Similarity	NPC13282
0.8345	Intermediate Similarity	NPC217914
0.8344	Intermediate Similarity	NPC472299
0.8308	Intermediate Similarity	NPC137710
0.8298	Intermediate Similarity	NPC202260
0.8286	Intermediate Similarity	NPC64157
0.8286	Intermediate Similarity	NPC278832
0.8278	Intermediate Similarity	NPC123153
0.8273	Intermediate Similarity	NPC274876
0.8271	Intermediate Similarity	NPC141252
0.8271	Intermediate Similarity	NPC11799
0.8255	Intermediate Similarity	NPC24232
0.8243	Intermediate Similarity	NPC144010
0.8227	Intermediate Similarity	NPC186647
0.8227	Intermediate Similarity	NPC130976
0.8209	Intermediate Similarity	NPC471074
0.8209	Intermediate Similarity	NPC473885
0.8201	Intermediate Similarity	NPC470406
0.82	Intermediate Similarity	NPC179170
0.8194	Intermediate Similarity	NPC27220
0.8188	Intermediate Similarity	NPC145830
0.8175	Intermediate Similarity	NPC57552
0.8169	Intermediate Similarity	NPC62735
0.8162	Intermediate Similarity	NPC428300
0.8156	Intermediate Similarity	NPC471670
0.8129	Intermediate Similarity	NPC293253
0.8125	Intermediate Similarity	NPC263337
0.8121	Intermediate Similarity	NPC472406
0.8116	Intermediate Similarity	NPC245395
0.8092	Intermediate Similarity	NPC180924
0.8088	Intermediate Similarity	NPC177925
0.8088	Intermediate Similarity	NPC474264
0.8082	Intermediate Similarity	NPC189650
0.8082	Intermediate Similarity	NPC308006
0.8079	Intermediate Similarity	NPC290927
0.8077	Intermediate Similarity	NPC279768
0.8077	Intermediate Similarity	NPC41689
0.8074	Intermediate Similarity	NPC75432
0.8058	Intermediate Similarity	NPC301717
0.8058	Intermediate Similarity	NPC470977
0.8058	Intermediate Similarity	NPC196979
0.8058	Intermediate Similarity	NPC470976
0.8043	Intermediate Similarity	NPC66246
0.8043	Intermediate Similarity	NPC170546
0.8041	Intermediate Similarity	NPC478163
0.8041	Intermediate Similarity	NPC150215
0.8039	Intermediate Similarity	NPC96342
0.8039	Intermediate Similarity	NPC10051
0.8039	Intermediate Similarity	NPC246647
0.8039	Intermediate Similarity	NPC299094
0.8039	Intermediate Similarity	NPC212967
0.8039	Intermediate Similarity	NPC164110
0.8029	Intermediate Similarity	NPC329707
0.8028	Intermediate Similarity	NPC163029
0.8015	Intermediate Similarity	NPC83301
0.8015	Intermediate Similarity	NPC232387
0.8013	Intermediate Similarity	NPC308156
0.8	Intermediate Similarity	NPC149780
0.7987	Intermediate Similarity	NPC192069
0.7986	Intermediate Similarity	NPC282230
0.7986	Intermediate Similarity	NPC183348
0.7986	Intermediate Similarity	NPC470407
0.7975	Intermediate Similarity	NPC472660
0.7974	Intermediate Similarity	NPC221992
0.7973	Intermediate Similarity	NPC39361
0.7973	Intermediate Similarity	NPC473927
0.7972	Intermediate Similarity	NPC290601
0.7961	Intermediate Similarity	NPC88958
0.7959	Intermediate Similarity	NPC471305
0.7959	Intermediate Similarity	NPC56731
0.7958	Intermediate Similarity	NPC22644
0.7956	Intermediate Similarity	NPC141059
0.7941	Intermediate Similarity	NPC111088
0.7941	Intermediate Similarity	NPC56332
0.7939	Intermediate Similarity	NPC316062
0.7929	Intermediate Similarity	NPC15083
0.7919	Intermediate Similarity	NPC198427
0.7917	Intermediate Similarity	NPC265181
0.7914	Intermediate Similarity	NPC939
0.7911	Intermediate Similarity	NPC255787
0.7911	Intermediate Similarity	NPC291742
0.7908	Intermediate Similarity	NPC478159
0.7908	Intermediate Similarity	NPC478161
0.7908	Intermediate Similarity	NPC148938
0.7907	Intermediate Similarity	NPC22678
0.7905	Intermediate Similarity	NPC208584
0.7898	Intermediate Similarity	NPC132054
0.7895	Intermediate Similarity	NPC282793
0.7895	Intermediate Similarity	NPC27615
0.7895	Intermediate Similarity	NPC38361
0.7895	Intermediate Similarity	NPC130015
0.7895	Intermediate Similarity	NPC87708
0.7891	Intermediate Similarity	NPC472840
0.7887	Intermediate Similarity	NPC1249
0.7885	Intermediate Similarity	NPC269117
0.7885	Intermediate Similarity	NPC24761
0.7879	Intermediate Similarity	NPC212918
0.7872	Intermediate Similarity	NPC312560
0.7872	Intermediate Similarity	NPC474340
0.7871	Intermediate Similarity	NPC250076
0.7871	Intermediate Similarity	NPC226287
0.7868	Intermediate Similarity	NPC182646
0.7868	Intermediate Similarity	NPC118853
0.7867	Intermediate Similarity	NPC474107
0.7867	Intermediate Similarity	NPC472839
0.7863	Intermediate Similarity	NPC205523
0.7863	Intermediate Similarity	NPC150895
0.7862	Intermediate Similarity	NPC112757
0.7857	Intermediate Similarity	NPC61788
0.7857	Intermediate Similarity	NPC470725
0.7852	Intermediate Similarity	NPC71821
0.7852	Intermediate Similarity	NPC190572
0.7847	Intermediate Similarity	NPC177262
0.7847	Intermediate Similarity	NPC29638
0.7843	Intermediate Similarity	NPC469966
0.7843	Intermediate Similarity	NPC84721
0.7843	Intermediate Similarity	NPC235333
0.7842	Intermediate Similarity	NPC125887
0.7842	Intermediate Similarity	NPC3009
0.7842	Intermediate Similarity	NPC181675
0.7838	Intermediate Similarity	NPC469642
0.7838	Intermediate Similarity	NPC472836
0.7838	Intermediate Similarity	NPC91694
0.7838	Intermediate Similarity	NPC469385
0.7838	Intermediate Similarity	NPC17262
0.7838	Intermediate Similarity	NPC300603
0.7836	Intermediate Similarity	NPC232958
0.7832	Intermediate Similarity	NPC88065
0.7832	Intermediate Similarity	NPC95485
0.7832	Intermediate Similarity	NPC89504
0.7829	Intermediate Similarity	NPC58668
0.7829	Intermediate Similarity	NPC474417
0.7829	Intermediate Similarity	NPC72958
0.7829	Intermediate Similarity	NPC149085
0.7829	Intermediate Similarity	NPC106372
0.7829	Intermediate Similarity	NPC232645
0.7829	Intermediate Similarity	NPC149526
0.7823	Intermediate Similarity	NPC329493
0.7821	Intermediate Similarity	NPC21046
0.782	Intermediate Similarity	NPC171023
0.7817	Intermediate Similarity	NPC59459
0.7815	Intermediate Similarity	NPC288036
0.7815	Intermediate Similarity	NPC100985
0.7815	Intermediate Similarity	NPC228906
0.7815	Intermediate Similarity	NPC158338
0.7815	Intermediate Similarity	NPC97029
0.7815	Intermediate Similarity	NPC469416
0.7815	Intermediate Similarity	NPC97028
0.7815	Intermediate Similarity	NPC65589
0.7815	Intermediate Similarity	NPC471348
0.7808	Intermediate Similarity	NPC472523
0.7801	Intermediate Similarity	NPC41847
0.7801	Intermediate Similarity	NPC473982
0.78	Intermediate Similarity	NPC22005
0.78	Intermediate Similarity	NPC93666
0.78	Intermediate Similarity	NPC7943
0.78	Intermediate Similarity	NPC123202
0.78	Intermediate Similarity	NPC252208
0.7799	Intermediate Similarity	NPC298071
0.7799	Intermediate Similarity	NPC191012
0.7794	Intermediate Similarity	NPC16922
0.7792	Intermediate Similarity	NPC213936
0.7792	Intermediate Similarity	NPC233776
0.7792	Intermediate Similarity	NPC297531
0.7791	Intermediate Similarity	NPC295914
0.7785	Intermediate Similarity	NPC233763
0.7785	Intermediate Similarity	NPC49282
0.7785	Intermediate Similarity	NPC62799

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 NPC324117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	460
0.1-0.2	1000
0.2-0.3	1426
0.3-0.4	2758
0.4-0.5	1953
0.5-0.6	1050
0.6-0.7	437
0.7-0.8	63
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8429	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD1651	Approved
0.8267	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD1281	Approved
0.7941	Intermediate Similarity	NPD1283	Approved
0.7941	Intermediate Similarity	NPD1876	Approved
0.7917	Intermediate Similarity	NPD1471	Phase 3
0.7917	Intermediate Similarity	NPD2346	Discontinued
0.7872	Intermediate Similarity	NPD2979	Phase 3
0.7794	Intermediate Similarity	NPD3972	Approved
0.7793	Intermediate Similarity	NPD2344	Approved
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.777	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD5691	Approved
0.7755	Intermediate Similarity	NPD7003	Approved
0.7733	Intermediate Similarity	NPD6273	Approved
0.7721	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD1241	Discontinued
0.7697	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1243	Approved
0.7682	Intermediate Similarity	NPD920	Approved
0.7667	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2438	Suspended
0.7603	Intermediate Similarity	NPD2531	Phase 2
0.7584	Intermediate Similarity	NPD2309	Approved
0.7552	Intermediate Similarity	NPD8032	Phase 2
0.7532	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD2796	Approved
0.7464	Intermediate Similarity	NPD1611	Approved
0.7455	Intermediate Similarity	NPD6559	Discontinued
0.745	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2798	Approved
0.7445	Intermediate Similarity	NPD4626	Approved
0.7445	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1247	Approved
0.7436	Intermediate Similarity	NPD6280	Approved
0.7436	Intermediate Similarity	NPD6279	Approved
0.7415	Intermediate Similarity	NPD3748	Approved
0.7375	Intermediate Similarity	NPD5494	Approved
0.7375	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4477	Approved
0.7365	Intermediate Similarity	NPD4476	Approved
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7361	Intermediate Similarity	NPD2313	Discontinued
0.7355	Intermediate Similarity	NPD3226	Approved
0.7343	Intermediate Similarity	NPD6832	Phase 2
0.7329	Intermediate Similarity	NPD6959	Discontinued
0.732	Intermediate Similarity	NPD2533	Approved
0.732	Intermediate Similarity	NPD2534	Approved
0.732	Intermediate Similarity	NPD2532	Approved
0.7319	Intermediate Similarity	NPD17	Approved
0.7317	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4628	Phase 3
0.726	Intermediate Similarity	NPD4060	Phase 1
0.726	Intermediate Similarity	NPD4307	Phase 2
0.7244	Intermediate Similarity	NPD7458	Discontinued
0.7234	Intermediate Similarity	NPD5327	Phase 3
0.7226	Intermediate Similarity	NPD3869	Phase 3
0.7226	Intermediate Similarity	NPD3873	Phase 3
0.7211	Intermediate Similarity	NPD6355	Discontinued
0.7211	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3750	Approved
0.7169	Intermediate Similarity	NPD5844	Phase 1
0.7163	Intermediate Similarity	NPD1608	Approved
0.7162	Intermediate Similarity	NPD1607	Approved
0.7134	Intermediate Similarity	NPD3926	Phase 2
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7133	Intermediate Similarity	NPD2797	Approved
0.7133	Intermediate Similarity	NPD3267	Approved
0.7123	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5585	Approved
0.7097	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6599	Discontinued
0.7073	Intermediate Similarity	NPD6808	Phase 2
0.7067	Intermediate Similarity	NPD4308	Phase 3
0.7063	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1549	Phase 2
0.7037	Intermediate Similarity	NPD3749	Approved
0.7027	Intermediate Similarity	NPD1240	Approved
0.7027	Intermediate Similarity	NPD3140	Approved
0.7027	Intermediate Similarity	NPD3142	Approved
0.7027	Intermediate Similarity	NPD4140	Approved
0.7025	Intermediate Similarity	NPD2651	Approved
0.7025	Intermediate Similarity	NPD2649	Approved
0.702	Intermediate Similarity	NPD6099	Approved
0.702	Intermediate Similarity	NPD6100	Approved
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2296	Approved
0.7013	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD7177	Discontinued
0.6993	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5536	Phase 2
0.6978	Remote Similarity	NPD7644	Approved
0.6975	Remote Similarity	NPD3882	Suspended
0.6975	Remote Similarity	NPD7768	Phase 2
0.6974	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1201	Approved
0.6963	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1510	Phase 2
0.6954	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1778	Approved
0.6948	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7473	Discontinued
0.6943	Remote Similarity	NPD5049	Phase 3
0.6939	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4625	Phase 3
0.6937	Remote Similarity	NPD7411	Suspended
0.6929	Remote Similarity	NPD1894	Discontinued
0.6928	Remote Similarity	NPD2897	Discontinued
0.6923	Remote Similarity	NPD6799	Approved
0.6918	Remote Similarity	NPD9494	Approved
0.6912	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5404	Approved
0.6908	Remote Similarity	NPD5405	Approved
0.6908	Remote Similarity	NPD5406	Approved
0.6908	Remote Similarity	NPD5408	Approved
0.6903	Remote Similarity	NPD3887	Approved
0.6899	Remote Similarity	NPD7427	Discontinued
0.6897	Remote Similarity	NPD1203	Approved
0.6897	Remote Similarity	NPD1470	Approved
0.6892	Remote Similarity	NPD411	Approved
0.6892	Remote Similarity	NPD6798	Discontinued
0.6892	Remote Similarity	NPD3764	Approved
0.6883	Remote Similarity	NPD2800	Approved
0.6879	Remote Similarity	NPD3445	Approved
0.6879	Remote Similarity	NPD3025	Approved
0.6879	Remote Similarity	NPD3024	Approved
0.6879	Remote Similarity	NPD3444	Approved
0.6879	Remote Similarity	NPD3443	Approved
0.6875	Remote Similarity	NPD4359	Approved
0.6867	Remote Similarity	NPD4618	Approved
0.6867	Remote Similarity	NPD4622	Approved
0.6867	Remote Similarity	NPD6232	Discontinued
0.6867	Remote Similarity	NPD7229	Phase 3
0.6852	Remote Similarity	NPD5761	Phase 2
0.6852	Remote Similarity	NPD5760	Phase 2
0.6849	Remote Similarity	NPD1019	Discontinued
0.6839	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8434	Phase 2
0.6839	Remote Similarity	NPD4110	Phase 3
0.6831	Remote Similarity	NPD3019	Approved
0.6831	Remote Similarity	NPD2932	Approved
0.6829	Remote Similarity	NPD7075	Discontinued
0.6828	Remote Similarity	NPD6696	Suspended
0.6821	Remote Similarity	NPD2157	Approved
0.6812	Remote Similarity	NPD1398	Phase 1
0.6812	Remote Similarity	NPD5283	Phase 1
0.681	Remote Similarity	NPD5977	Approved
0.681	Remote Similarity	NPD5978	Approved
0.6806	Remote Similarity	NPD9717	Approved
0.6806	Remote Similarity	NPD1840	Phase 2
0.6803	Remote Similarity	NPD2861	Phase 2
0.68	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3134	Approved
0.679	Remote Similarity	NPD1934	Approved
0.679	Remote Similarity	NPD6801	Discontinued
0.6788	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7340	Approved
0.6786	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3023	Approved
0.6783	Remote Similarity	NPD3026	Approved
0.6779	Remote Similarity	NPD7985	Registered
0.6779	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5689	Approved
0.6776	Remote Similarity	NPD5688	Approved
0.6774	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4661	Approved
0.6772	Remote Similarity	NPD4662	Approved
0.677	Remote Similarity	NPD4380	Phase 2
0.6766	Remote Similarity	NPD5711	Approved
0.6766	Remote Similarity	NPD5710	Approved
0.6763	Remote Similarity	NPD8313	Approved
0.6763	Remote Similarity	NPD8312	Approved
0.6761	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1669	Approved
0.6755	Remote Similarity	NPD1933	Approved
0.6755	Remote Similarity	NPD5735	Approved
0.6753	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2353	Approved
0.6753	Remote Similarity	NPD6002	Phase 3
0.6753	Remote Similarity	NPD5763	Approved
0.6753	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6004	Phase 3
0.6753	Remote Similarity	NPD6005	Phase 3
0.6753	Remote Similarity	NPD5762	Approved
0.6753	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3658	Clinical (unspecified phase)

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