NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	261.435
LogP:	2.943
LogD:	3.405
LogS:	-4.173
# Rotatable Bonds:	1
TPSA:	47.28
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.561
Synthetic Accessibility Score:	4.074
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.644
MDCK Permeability:	2.3979146135388874e-05
Pgp-inhibitor:	0.345
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	89.33892059326172%
Volume Distribution (VD):	1.989
Pgp-substrate:	10.28300666809082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.707
CYP2C19-substrate:	0.623
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.453
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.905
CYP3A4-substrate:	0.556

ADMET: Excretion

Clearance (CL):	7.686
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.181
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.528
Maximum Recommended Daily Dose:	0.601
Skin Sensitization:	0.26
Carcinogencity:	0.909
Eye Corrosion:	0.017
Eye Irritation:	0.028
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC177262

Natural Product ID:	NPC177262
*Common Name:**	Chlorantene F
IUPAC Name:	(5S,6S)-6-ethenyl-3,6-dimethyl-5-prop-1-en-2-yl-5H-1-benzofuran-4,7-dione
Synonyms:	Chlorantene F
Standard InCHIKey:	RLWUPZZWFFGPKU-ABAIWWIYSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-6-15(5)11(8(2)3)12(16)10-9(4)7-18-13(10)14(15)17/h6-7,11H,1-2H2,3-5H3/t11-,15+/m1/s1
SMILES:	C=C[C@@]1(C)[C@H](C(=C)C)C(=O)c2c(C)coc2C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457444
PubChem CID:	25147592
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22372956]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588583]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724564]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT452	Organism	Helicobacter pylori SS1	Helicobacter pylori SS1	MIC	=	25.0	ug.mL-1	PMID[524895]

☑ 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 NPC177262 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	400
0.1-0.2	1637
0.2-0.3	3890
0.3-0.4	10147
0.4-0.5	10570
0.5-0.6	6751
0.6-0.7	8030
0.7-0.8	1213
0.8-0.85	40
0.85-0.9	16
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8873	High Similarity	NPC233763
0.8849	High Similarity	NPC18904
0.8811	High Similarity	NPC224418
0.8777	High Similarity	NPC265181
0.8776	High Similarity	NPC88958
0.8722	High Similarity	NPC184391
0.869	High Similarity	NPC192069
0.8681	High Similarity	NPC281398
0.8636	High Similarity	NPC178382
0.8613	High Similarity	NPC293253
0.8593	High Similarity	NPC59502
0.8582	High Similarity	NPC473681
0.8582	High Similarity	NPC218204
0.8582	High Similarity	NPC61157
0.855	High Similarity	NPC97566
0.8523	High Similarity	NPC472786
0.8472	Intermediate Similarity	NPC84479
0.8472	Intermediate Similarity	NPC117674
0.8446	Intermediate Similarity	NPC472787
0.8446	Intermediate Similarity	NPC144010
0.8414	Intermediate Similarity	NPC93241
0.8414	Intermediate Similarity	NPC114513
0.8414	Intermediate Similarity	NPC245522
0.8414	Intermediate Similarity	NPC27798
0.84	Intermediate Similarity	NPC179170
0.84	Intermediate Similarity	NPC75310
0.8389	Intermediate Similarity	NPC145830
0.8389	Intermediate Similarity	NPC475777
0.8356	Intermediate Similarity	NPC478166
0.8356	Intermediate Similarity	NPC62799
0.8333	Intermediate Similarity	NPC473152
0.8308	Intermediate Similarity	NPC79202
0.8308	Intermediate Similarity	NPC59035
0.8289	Intermediate Similarity	NPC81405
0.8286	Intermediate Similarity	NPC200718
0.8278	Intermediate Similarity	NPC472785
0.8276	Intermediate Similarity	NPC64568
0.8276	Intermediate Similarity	NPC205071
0.8267	Intermediate Similarity	NPC471613
0.8248	Intermediate Similarity	NPC329707
0.8243	Intermediate Similarity	NPC252208
0.8239	Intermediate Similarity	NPC307401
0.8239	Intermediate Similarity	NPC42400
0.8235	Intermediate Similarity	NPC140952
0.8231	Intermediate Similarity	NPC262198
0.8207	Intermediate Similarity	NPC263337
0.8188	Intermediate Similarity	NPC280025
0.8182	Intermediate Similarity	NPC333139
0.817	Intermediate Similarity	NPC221992
0.8162	Intermediate Similarity	NPC471074
0.8162	Intermediate Similarity	NPC473885
0.8143	Intermediate Similarity	NPC471817
0.8143	Intermediate Similarity	NPC473982
0.8133	Intermediate Similarity	NPC226578
0.8129	Intermediate Similarity	NPC45947
0.8125	Intermediate Similarity	NPC202260
0.8121	Intermediate Similarity	NPC19747
0.8108	Intermediate Similarity	NPC97904
0.8085	Intermediate Similarity	NPC470740
0.8082	Intermediate Similarity	NPC52412
0.8069	Intermediate Similarity	NPC148374
0.8067	Intermediate Similarity	NPC211625
0.8065	Intermediate Similarity	NPC287559
0.8056	Intermediate Similarity	NPC236532
0.8054	Intermediate Similarity	NPC250331
0.805	Intermediate Similarity	NPC44602
0.8042	Intermediate Similarity	NPC217914
0.8042	Intermediate Similarity	NPC146872
0.8042	Intermediate Similarity	NPC46896
0.8039	Intermediate Similarity	NPC25351
0.8038	Intermediate Similarity	NPC473766
0.8038	Intermediate Similarity	NPC473753
0.8025	Intermediate Similarity	NPC472664
0.8025	Intermediate Similarity	NPC56358
0.8	Intermediate Similarity	NPC294300
0.8	Intermediate Similarity	NPC104380
0.8	Intermediate Similarity	NPC476404
0.8	Intermediate Similarity	NPC317900
0.8	Intermediate Similarity	NPC217602
0.8	Intermediate Similarity	NPC473368
0.8	Intermediate Similarity	NPC473282
0.8	Intermediate Similarity	NPC233707
0.8	Intermediate Similarity	NPC10051
0.8	Intermediate Similarity	NPC299094
0.7987	Intermediate Similarity	NPC474261
0.7975	Intermediate Similarity	NPC475779
0.7973	Intermediate Similarity	NPC199044
0.7973	Intermediate Similarity	NPC238843
0.7972	Intermediate Similarity	NPC158525
0.7972	Intermediate Similarity	NPC209858
0.7945	Intermediate Similarity	NPC90296
0.7937	Intermediate Similarity	NPC473945
0.7933	Intermediate Similarity	NPC71821
0.7931	Intermediate Similarity	NPC472376
0.7929	Intermediate Similarity	NPC50583
0.7929	Intermediate Similarity	NPC208389
0.7925	Intermediate Similarity	NPC270312
0.7925	Intermediate Similarity	NPC472784
0.7922	Intermediate Similarity	NPC290927
0.7919	Intermediate Similarity	NPC185456
0.7914	Intermediate Similarity	NPC246392
0.7905	Intermediate Similarity	NPC243577
0.7905	Intermediate Similarity	NPC103134
0.7898	Intermediate Similarity	NPC18986
0.7898	Intermediate Similarity	NPC472781
0.7898	Intermediate Similarity	NPC472782
0.7895	Intermediate Similarity	NPC46551
0.7895	Intermediate Similarity	NPC45536
0.7885	Intermediate Similarity	NPC472823
0.7877	Intermediate Similarity	NPC474722
0.7871	Intermediate Similarity	NPC41880
0.7871	Intermediate Similarity	NPC104736
0.7867	Intermediate Similarity	NPC471292
0.7862	Intermediate Similarity	NPC232996
0.7862	Intermediate Similarity	NPC121995
0.7862	Intermediate Similarity	NPC132054
0.7857	Intermediate Similarity	NPC26532
0.7857	Intermediate Similarity	NPC114880
0.7857	Intermediate Similarity	NPC282793
0.7853	Intermediate Similarity	NPC167340
0.7852	Intermediate Similarity	NPC142113
0.7848	Intermediate Similarity	NPC472780
0.7848	Intermediate Similarity	NPC472783
0.7847	Intermediate Similarity	NPC324117
0.7843	Intermediate Similarity	NPC272590
0.7843	Intermediate Similarity	NPC472406
0.7842	Intermediate Similarity	NPC470858
0.7834	Intermediate Similarity	NPC191828
0.7821	Intermediate Similarity	NPC472283
0.7821	Intermediate Similarity	NPC304692
0.782	Intermediate Similarity	NPC150895
0.7817	Intermediate Similarity	NPC61788
0.7815	Intermediate Similarity	NPC471346
0.7808	Intermediate Similarity	NPC301341
0.7808	Intermediate Similarity	NPC476943
0.7808	Intermediate Similarity	NPC284184
0.7808	Intermediate Similarity	NPC471996
0.7806	Intermediate Similarity	NPC42458
0.7806	Intermediate Similarity	NPC158261
0.7806	Intermediate Similarity	NPC469966
0.7805	Intermediate Similarity	NPC472665
0.78	Intermediate Similarity	NPC56731
0.7792	Intermediate Similarity	NPC246164
0.7785	Intermediate Similarity	NPC267632
0.7785	Intermediate Similarity	NPC197596
0.7778	Intermediate Similarity	NPC477404
0.7778	Intermediate Similarity	NPC159927
0.7778	Intermediate Similarity	NPC196864
0.7778	Intermediate Similarity	NPC212257
0.7778	Intermediate Similarity	NPC228842
0.7778	Intermediate Similarity	NPC469335
0.7778	Intermediate Similarity	NPC472298
0.7771	Intermediate Similarity	NPC116639
0.7771	Intermediate Similarity	NPC474611
0.7764	Intermediate Similarity	NPC191012
0.7764	Intermediate Similarity	NPC298071
0.7762	Intermediate Similarity	NPC279596
0.7762	Intermediate Similarity	NPC471995
0.7756	Intermediate Similarity	NPC60973
0.7756	Intermediate Similarity	NPC263265
0.7742	Intermediate Similarity	NPC24232
0.774	Intermediate Similarity	NPC310830
0.773	Intermediate Similarity	NPC279877
0.7727	Intermediate Similarity	NPC22678
0.7716	Intermediate Similarity	NPC302392
0.7708	Intermediate Similarity	NPC218838
0.7708	Intermediate Similarity	NPC471006
0.7704	Intermediate Similarity	NPC212918
0.7703	Intermediate Similarity	NPC201370
0.7703	Intermediate Similarity	NPC473983
0.7703	Intermediate Similarity	NPC56197
0.7702	Intermediate Similarity	NPC279768
0.7698	Intermediate Similarity	NPC118853
0.7698	Intermediate Similarity	NPC141252
0.7698	Intermediate Similarity	NPC11799
0.7697	Intermediate Similarity	NPC302987
0.7697	Intermediate Similarity	NPC190572
0.7692	Intermediate Similarity	NPC23559
0.7692	Intermediate Similarity	NPC298190
0.7692	Intermediate Similarity	NPC41719
0.7687	Intermediate Similarity	NPC220094
0.7682	Intermediate Similarity	NPC290038
0.7682	Intermediate Similarity	NPC469385
0.7682	Intermediate Similarity	NPC195920
0.7677	Intermediate Similarity	NPC121615
0.7677	Intermediate Similarity	NPC294511
0.7676	Intermediate Similarity	NPC198904
0.7673	Intermediate Similarity	NPC470939
0.7673	Intermediate Similarity	NPC68848
0.7671	Intermediate Similarity	NPC214572
0.7667	Intermediate Similarity	NPC27220
0.766	Intermediate Similarity	NPC237868
0.766	Intermediate Similarity	NPC290955
0.7658	Intermediate Similarity	NPC237155
0.7658	Intermediate Similarity	NPC477403
0.7655	Intermediate Similarity	NPC477536
0.7654	Intermediate Similarity	NPC472895
0.7647	Intermediate Similarity	NPC87466
0.7647	Intermediate Similarity	NPC198427
0.7647	Intermediate Similarity	NPC243704

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 NPC177262 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	1027
0.2-0.3	1833
0.3-0.4	2844
0.4-0.5	1951
0.5-0.6	861
0.6-0.7	240
0.7-0.8	26
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8777	High Similarity	NPD1471	Phase 3
0.8182	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2344	Approved
0.7517	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1247	Approved
0.7434	Intermediate Similarity	NPD2309	Approved
0.7412	Intermediate Similarity	NPD8434	Phase 2
0.7376	Intermediate Similarity	NPD3972	Approved
0.7308	Intermediate Similarity	NPD920	Approved
0.7296	Intermediate Similarity	NPD6279	Approved
0.7296	Intermediate Similarity	NPD6280	Approved
0.729	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD919	Approved
0.7273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5760	Phase 2
0.725	Intermediate Similarity	NPD5761	Phase 2
0.7219	Intermediate Similarity	NPD6764	Approved
0.7219	Intermediate Similarity	NPD6765	Approved
0.719	Intermediate Similarity	NPD2800	Approved
0.7186	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6599	Discontinued
0.7163	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1876	Approved
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD6808	Phase 2
0.7108	Intermediate Similarity	NPD3926	Phase 2
0.7105	Intermediate Similarity	NPD2796	Approved
0.7078	Intermediate Similarity	NPD1243	Approved
0.707	Intermediate Similarity	NPD2532	Approved
0.707	Intermediate Similarity	NPD2534	Approved
0.707	Intermediate Similarity	NPD2533	Approved
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7052	Intermediate Similarity	NPD6784	Approved
0.7052	Intermediate Similarity	NPD6785	Approved
0.7029	Intermediate Similarity	NPD1241	Discontinued
0.7	Intermediate Similarity	NPD3226	Approved
0.6994	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3882	Suspended
0.6939	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD8032	Phase 2
0.6928	Remote Similarity	NPD5494	Approved
0.6918	Remote Similarity	NPD6273	Approved
0.6899	Remote Similarity	NPD6799	Approved
0.689	Remote Similarity	NPD2296	Approved
0.689	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2313	Discontinued
0.6859	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1651	Approved
0.6846	Remote Similarity	NPD6832	Phase 2
0.6829	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7819	Suspended
0.6815	Remote Similarity	NPD4628	Phase 3
0.6806	Remote Similarity	NPD17	Approved
0.6765	Remote Similarity	NPD2403	Approved
0.6763	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3266	Approved
0.6757	Remote Similarity	NPD3267	Approved
0.6736	Remote Similarity	NPD5691	Approved
0.6732	Remote Similarity	NPD6355	Discontinued
0.6731	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD9092	Discovery
0.6712	Remote Similarity	NPD1281	Approved
0.6711	Remote Similarity	NPD1019	Discontinued
0.6707	Remote Similarity	NPD7411	Suspended
0.6707	Remote Similarity	NPD7075	Discontinued
0.6691	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1778	Approved
0.6688	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1607	Approved
0.6688	Remote Similarity	NPD1549	Phase 2
0.6688	Remote Similarity	NPD6651	Approved
0.6687	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD9494	Approved
0.6647	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3268	Approved
0.6627	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7236	Approved
0.6623	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5327	Phase 3
0.6621	Remote Similarity	NPD5585	Approved
0.6607	Remote Similarity	NPD3749	Approved
0.6604	Remote Similarity	NPD7003	Approved
0.6603	Remote Similarity	NPD1510	Phase 2
0.6585	Remote Similarity	NPD7458	Discontinued
0.6577	Remote Similarity	NPD1283	Approved
0.6561	Remote Similarity	NPD6099	Approved
0.6561	Remote Similarity	NPD2935	Discontinued
0.6561	Remote Similarity	NPD1551	Phase 2
0.6561	Remote Similarity	NPD6100	Approved
0.6558	Remote Similarity	NPD2979	Phase 3
0.6543	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD411	Approved
0.6534	Remote Similarity	NPD6559	Discontinued
0.6519	Remote Similarity	NPD2353	Approved
0.6519	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD447	Suspended
0.6506	Remote Similarity	NPD5890	Approved
0.6506	Remote Similarity	NPD5889	Approved
0.6503	Remote Similarity	NPD1512	Approved
0.6494	Remote Similarity	NPD2163	Approved
0.6491	Remote Similarity	NPD6959	Discontinued
0.6474	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1934	Approved
0.6463	Remote Similarity	NPD4626	Approved
0.6453	Remote Similarity	NPD5710	Approved
0.6453	Remote Similarity	NPD5711	Approved
0.6452	Remote Similarity	NPD4060	Phase 1
0.6452	Remote Similarity	NPD4140	Approved
0.6442	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2654	Approved
0.6437	Remote Similarity	NPD7473	Discontinued
0.6429	Remote Similarity	NPD6798	Discontinued
0.6429	Remote Similarity	NPD2182	Approved
0.6429	Remote Similarity	NPD2801	Approved
0.6424	Remote Similarity	NPD7239	Suspended
0.6424	Remote Similarity	NPD2797	Approved
0.6424	Remote Similarity	NPD1470	Approved
0.6424	Remote Similarity	NPD1203	Approved
0.6417	Remote Similarity	NPD4107	Approved
0.6414	Remote Similarity	NPD405	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4359	Approved
0.6398	Remote Similarity	NPD4110	Phase 3
0.6398	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3748	Approved
0.6391	Remote Similarity	NPD5402	Approved
0.6386	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD5647	Approved
0.638	Remote Similarity	NPD1511	Approved
0.6379	Remote Similarity	NPD6166	Phase 2
0.6379	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD1201	Approved
0.6375	Remote Similarity	NPD2897	Discontinued
0.6375	Remote Similarity	NPD4534	Discontinued
0.6364	Remote Similarity	NPD5403	Approved
0.6364	Remote Similarity	NPD7095	Approved
0.6364	Remote Similarity	NPD3873	Phase 3
0.6364	Remote Similarity	NPD3869	Phase 3
0.6364	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2354	Approved
0.6358	Remote Similarity	NPD6232	Discontinued
0.6358	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD2531	Phase 2
0.6352	Remote Similarity	NPD2438	Suspended
0.6352	Remote Similarity	NPD4476	Approved
0.6352	Remote Similarity	NPD4477	Approved
0.6349	Remote Similarity	NPD3057	Approved
0.6347	Remote Similarity	NPD6585	Discontinued
0.6347	Remote Similarity	NPD4380	Phase 2
0.6346	Remote Similarity	NPD4307	Phase 2
0.6345	Remote Similarity	NPD7157	Approved
0.6345	Remote Similarity	NPD8404	Phase 2
0.6341	Remote Similarity	NPD5401	Approved
0.6341	Remote Similarity	NPD4662	Approved
0.6341	Remote Similarity	NPD4661	Approved
0.6327	Remote Similarity	NPD9545	Approved
0.6313	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD6002	Phase 3
0.6312	Remote Similarity	NPD6005	Phase 3
0.6312	Remote Similarity	NPD6004	Phase 3
0.6312	Remote Similarity	NPD5762	Approved
0.6312	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5763	Approved
0.6312	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD3496	Discontinued
0.6309	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD3818	Discontinued
0.6306	Remote Similarity	NPD4618	Approved
0.6306	Remote Similarity	NPD4622	Approved
0.6306	Remote Similarity	NPD1933	Approved
0.6304	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5049	Phase 3
0.6301	Remote Similarity	NPD9493	Approved
0.6296	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4482	Phase 3
0.6296	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD2651	Approved
0.6287	Remote Similarity	NPD2649	Approved
0.6286	Remote Similarity	NPD3134	Approved
0.6284	Remote Similarity	NPD3024	Approved
0.6284	Remote Similarity	NPD3025	Approved
0.6278	Remote Similarity	NPD2971	Approved
0.6278	Remote Similarity	NPD2968	Approved
0.6276	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5958	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