NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.14
Volume:	284.238
LogP:	2.566
LogD:	2.851
LogS:	-3.962
# Rotatable Bonds:	3
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	4.18
Fsp3:	0.625
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:	-4.769
MDCK Permeability:	2.551846955611836e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.316

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	92.58524322509766%
Volume Distribution (VD):	1.272
Pgp-substrate:	12.234248161315918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.741
CYP1A2-substrate:	0.311
CYP2C19-inhibitor:	0.91
CYP2C19-substrate:	0.653
CYP2C9-inhibitor:	0.669
CYP2C9-substrate:	0.306
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.664
CYP3A4-substrate:	0.448

ADMET: Excretion

Clearance (CL):	4.101
Half-life (T1/2):	0.433

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.651
AMES Toxicity:	0.194
Rat Oral Acute Toxicity:	0.302
Maximum Recommended Daily Dose:	0.164
Skin Sensitization:	0.12
Carcinogencity:	0.458
Eye Corrosion:	0.004
Eye Irritation:	0.124
Respiratory Toxicity:	0.389

Download Data

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

Natural Product: NPC224418

Natural Product ID:	NPC224418
*Common Name:**	Norpinguisone Acetate
IUPAC Name:	[(4aR,7R,7aR)-4a,7-dimethyl-4-oxo-5,6,7,8-tetrahydrocyclopenta[f][1]benzofuran-7a-yl]methyl acetate
Synonyms:	Norpinguisone Acetate
Standard InCHIKey:	IUFYKFUROQQFKO-HPEXNQPKSA-N
Standard InCHI:	InChI=1S/C16H20O4/c1-10-4-6-15(3)14(18)12-5-7-19-13(12)8-16(10,15)9-20-11(2)17/h5,7,10H,4,6,8-9H2,1-3H3/t10-,15+,16-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(C)C(=O)c3ccoc3C[C@@]12COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774431
PubChem CID:	52951745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO30691	Porella chilensis	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[21384863]
NPO30691	Porella chilensis	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21384863]
NPO30908	Porella	Genus	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21384863]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	27.0	%	PMID[536320]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	20.0	%	PMID[536320]

☑ 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 NPC224418 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	391
0.1-0.2	1695
0.2-0.3	3529
0.3-0.4	9329
0.4-0.5	11472
0.5-0.6	6647
0.6-0.7	8216
0.7-0.8	1353
0.8-0.85	59
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9371	High Similarity	NPC233763
0.8811	High Similarity	NPC177262
0.8758	High Similarity	NPC81405
0.875	High Similarity	NPC25351
0.8718	High Similarity	NPC472664
0.8716	High Similarity	NPC471292
0.8707	High Similarity	NPC238843
0.8707	High Similarity	NPC199044
0.8701	High Similarity	NPC140952
0.8675	High Similarity	NPC144010
0.8649	High Similarity	NPC56731
0.8611	High Similarity	NPC42400
0.8599	High Similarity	NPC56358
0.8591	High Similarity	NPC62799
0.8581	High Similarity	NPC84479
0.8552	High Similarity	NPC236532
0.8542	High Similarity	NPC146872
0.8526	High Similarity	NPC287559
0.8526	High Similarity	NPC333139
0.8491	Intermediate Similarity	NPC270312
0.8483	Intermediate Similarity	NPC307401
0.8477	Intermediate Similarity	NPC93666
0.8462	Intermediate Similarity	NPC293253
0.8462	Intermediate Similarity	NPC470740
0.8452	Intermediate Similarity	NPC104736
0.8435	Intermediate Similarity	NPC18904
0.8435	Intermediate Similarity	NPC56197
0.8411	Intermediate Similarity	NPC281398
0.8405	Intermediate Similarity	NPC167340
0.8397	Intermediate Similarity	NPC304692
0.8389	Intermediate Similarity	NPC267632
0.8387	Intermediate Similarity	NPC472786
0.8367	Intermediate Similarity	NPC474722
0.8367	Intermediate Similarity	NPC202260
0.8366	Intermediate Similarity	NPC156189
0.8355	Intermediate Similarity	NPC19747
0.8354	Intermediate Similarity	NPC197596
0.8344	Intermediate Similarity	NPC262198
0.8333	Intermediate Similarity	NPC142113
0.8333	Intermediate Similarity	NPC41880
0.8333	Intermediate Similarity	NPC204663
0.8323	Intermediate Similarity	NPC471863
0.8313	Intermediate Similarity	NPC121995
0.8312	Intermediate Similarity	NPC272590
0.8311	Intermediate Similarity	NPC148374
0.831	Intermediate Similarity	NPC59502
0.8303	Intermediate Similarity	NPC295914
0.8301	Intermediate Similarity	NPC211625
0.8301	Intermediate Similarity	NPC192069
0.8301	Intermediate Similarity	NPC472654
0.8299	Intermediate Similarity	NPC476943
0.8289	Intermediate Similarity	NPC71821
0.828	Intermediate Similarity	NPC195131
0.8278	Intermediate Similarity	NPC185456
0.8269	Intermediate Similarity	NPC88958
0.8269	Intermediate Similarity	NPC179170
0.8269	Intermediate Similarity	NPC75310
0.8267	Intermediate Similarity	NPC205071
0.8258	Intermediate Similarity	NPC145830
0.8258	Intermediate Similarity	NPC246164
0.8247	Intermediate Similarity	NPC469335
0.8247	Intermediate Similarity	NPC196864
0.8247	Intermediate Similarity	NPC472298
0.8247	Intermediate Similarity	NPC477404
0.8247	Intermediate Similarity	NPC159927
0.8243	Intermediate Similarity	NPC265181
0.8242	Intermediate Similarity	NPC472665
0.8239	Intermediate Similarity	NPC18986
0.8231	Intermediate Similarity	NPC470742
0.8231	Intermediate Similarity	NPC310830
0.8228	Intermediate Similarity	NPC474932
0.8228	Intermediate Similarity	NPC474611
0.8228	Intermediate Similarity	NPC84349
0.8212	Intermediate Similarity	NPC117674
0.82	Intermediate Similarity	NPC473152
0.8194	Intermediate Similarity	NPC472787
0.8194	Intermediate Similarity	NPC136340
0.8194	Intermediate Similarity	NPC116717
0.8187	Intermediate Similarity	NPC285567
0.8187	Intermediate Similarity	NPC663
0.8187	Intermediate Similarity	NPC224394
0.8187	Intermediate Similarity	NPC283209
0.8182	Intermediate Similarity	NPC329180
0.8182	Intermediate Similarity	NPC95526
0.8182	Intermediate Similarity	NPC470791
0.8182	Intermediate Similarity	NPC470790
0.8176	Intermediate Similarity	NPC220094
0.817	Intermediate Similarity	NPC221809
0.817	Intermediate Similarity	NPC10088
0.8165	Intermediate Similarity	NPC221992
0.816	Intermediate Similarity	NPC44602
0.8158	Intermediate Similarity	NPC27798
0.8158	Intermediate Similarity	NPC93241
0.8158	Intermediate Similarity	NPC34056
0.8153	Intermediate Similarity	NPC92979
0.8148	Intermediate Similarity	NPC473753
0.8148	Intermediate Similarity	NPC473766
0.8146	Intermediate Similarity	NPC223415
0.8141	Intermediate Similarity	NPC475777
0.8141	Intermediate Similarity	NPC75906
0.8138	Intermediate Similarity	NPC471817
0.8137	Intermediate Similarity	NPC276735
0.8137	Intermediate Similarity	NPC261184
0.8133	Intermediate Similarity	NPC20500
0.8129	Intermediate Similarity	NPC470997
0.8129	Intermediate Similarity	NPC212257
0.8129	Intermediate Similarity	NPC5180
0.8129	Intermediate Similarity	NPC228842
0.8125	Intermediate Similarity	NPC472767
0.8125	Intermediate Similarity	NPC471167
0.8125	Intermediate Similarity	NPC68848
0.8125	Intermediate Similarity	NPC471166
0.8125	Intermediate Similarity	NPC188649
0.8125	Intermediate Similarity	NPC6326
0.8125	Intermediate Similarity	NPC471003
0.8121	Intermediate Similarity	NPC474615
0.8113	Intermediate Similarity	NPC473368
0.8108	Intermediate Similarity	NPC170604
0.8108	Intermediate Similarity	NPC215109
0.8105	Intermediate Similarity	NPC276676
0.8105	Intermediate Similarity	NPC346
0.8095	Intermediate Similarity	NPC92941
0.8092	Intermediate Similarity	NPC251865
0.8092	Intermediate Similarity	NPC476944
0.8089	Intermediate Similarity	NPC178932
0.8089	Intermediate Similarity	NPC10429
0.8089	Intermediate Similarity	NPC114880
0.8086	Intermediate Similarity	NPC475779
0.8079	Intermediate Similarity	NPC263337
0.8079	Intermediate Similarity	NPC52412
0.8077	Intermediate Similarity	NPC291150
0.8075	Intermediate Similarity	NPC88841
0.8075	Intermediate Similarity	NPC471168
0.8075	Intermediate Similarity	NPC288602
0.8069	Intermediate Similarity	NPC298190
0.8065	Intermediate Similarity	NPC195325
0.8065	Intermediate Similarity	NPC471001
0.8065	Intermediate Similarity	NPC234494
0.8063	Intermediate Similarity	NPC191828
0.8052	Intermediate Similarity	NPC302987
0.8052	Intermediate Similarity	NPC216755
0.8052	Intermediate Similarity	NPC471174
0.805	Intermediate Similarity	NPC469847
0.8039	Intermediate Similarity	NPC290038
0.8038	Intermediate Similarity	NPC469336
0.8038	Intermediate Similarity	NPC472785
0.8038	Intermediate Similarity	NPC469850
0.8028	Intermediate Similarity	NPC179354
0.8026	Intermediate Similarity	NPC470273
0.8026	Intermediate Similarity	NPC470741
0.8025	Intermediate Similarity	NPC33938
0.8025	Intermediate Similarity	NPC121615
0.8025	Intermediate Similarity	NPC294511
0.8014	Intermediate Similarity	NPC125153
0.8013	Intermediate Similarity	NPC46551
0.8013	Intermediate Similarity	NPC205765
0.8012	Intermediate Similarity	NPC472668
0.8	Intermediate Similarity	NPC472823
0.8	Intermediate Similarity	NPC21460
0.8	Intermediate Similarity	NPC97566
0.7975	Intermediate Similarity	NPC44606
0.7975	Intermediate Similarity	NPC24232
0.7975	Intermediate Similarity	NPC149945
0.7973	Intermediate Similarity	NPC159786
0.7963	Intermediate Similarity	NPC472669
0.7963	Intermediate Similarity	NPC165218
0.7962	Intermediate Similarity	NPC18135
0.7961	Intermediate Similarity	NPC121158
0.7959	Intermediate Similarity	NPC471006
0.7958	Intermediate Similarity	NPC178382
0.7952	Intermediate Similarity	NPC469848
0.795	Intermediate Similarity	NPC472299
0.7937	Intermediate Similarity	NPC194499
0.7937	Intermediate Similarity	NPC472772
0.7937	Intermediate Similarity	NPC195954
0.7937	Intermediate Similarity	NPC167142
0.7937	Intermediate Similarity	NPC88007
0.7937	Intermediate Similarity	NPC472283
0.7937	Intermediate Similarity	NPC197137
0.7935	Intermediate Similarity	NPC470941
0.7931	Intermediate Similarity	NPC208389
0.7927	Intermediate Similarity	NPC476224
0.7927	Intermediate Similarity	NPC478179
0.7927	Intermediate Similarity	NPC472764
0.7927	Intermediate Similarity	NPC472784
0.7925	Intermediate Similarity	NPC290927
0.7925	Intermediate Similarity	NPC264943
0.7922	Intermediate Similarity	NPC245522
0.7922	Intermediate Similarity	NPC195920
0.7922	Intermediate Similarity	NPC114513
0.7919	Intermediate Similarity	NPC46896
0.7911	Intermediate Similarity	NPC471002
0.7911	Intermediate Similarity	NPC470996
0.7908	Intermediate Similarity	NPC80635
0.7902	Intermediate Similarity	NPC471074
0.7902	Intermediate Similarity	NPC473885
0.7901	Intermediate Similarity	NPC472782
0.7901	Intermediate Similarity	NPC472781
0.7898	Intermediate Similarity	NPC476122
0.7892	Intermediate Similarity	NPC294512

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 NPC224418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	1020
0.2-0.3	1898
0.3-0.4	2760
0.4-0.5	2038
0.5-0.6	817
0.6-0.7	242
0.7-0.8	29
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD5537	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1471	Phase 3
0.7812	Intermediate Similarity	NPD5760	Phase 2
0.7812	Intermediate Similarity	NPD5761	Phase 2
0.7771	Intermediate Similarity	NPD920	Approved
0.7763	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6764	Approved
0.7751	Intermediate Similarity	NPD6765	Approved
0.763	Intermediate Similarity	NPD8434	Phase 2
0.7572	Intermediate Similarity	NPD6785	Approved
0.7572	Intermediate Similarity	NPD6784	Approved
0.7532	Intermediate Similarity	NPD2344	Approved
0.7532	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6808	Phase 2
0.7453	Intermediate Similarity	NPD3226	Approved
0.7419	Intermediate Similarity	NPD2346	Discontinued
0.7415	Intermediate Similarity	NPD1876	Approved
0.7405	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6273	Approved
0.7342	Intermediate Similarity	NPD2309	Approved
0.7303	Intermediate Similarity	NPD8032	Phase 2
0.7279	Intermediate Similarity	NPD3972	Approved
0.7237	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD6832	Phase 2
0.7219	Intermediate Similarity	NPD1247	Approved
0.7215	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1243	Approved
0.7212	Intermediate Similarity	NPD6280	Approved
0.7212	Intermediate Similarity	NPD6279	Approved
0.7205	Intermediate Similarity	NPD2532	Approved
0.7205	Intermediate Similarity	NPD2533	Approved
0.7205	Intermediate Similarity	NPD2534	Approved
0.7202	Intermediate Similarity	NPD919	Approved
0.7195	Intermediate Similarity	NPD6599	Discontinued
0.717	Intermediate Similarity	NPD4628	Phase 3
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7107	Intermediate Similarity	NPD2800	Approved
0.7097	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1019	Discontinued
0.7059	Intermediate Similarity	NPD5494	Approved
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.7025	Intermediate Similarity	NPD2796	Approved
0.702	Intermediate Similarity	NPD3266	Approved
0.702	Intermediate Similarity	NPD3267	Approved
0.698	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7236	Approved
0.6974	Remote Similarity	NPD2798	Approved
0.6959	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3749	Approved
0.6936	Remote Similarity	NPD3926	Phase 2
0.6933	Remote Similarity	NPD9717	Approved
0.6933	Remote Similarity	NPD6799	Approved
0.6928	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD2979	Phase 3
0.6923	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8127	Discontinued
0.6903	Remote Similarity	NPD3268	Approved
0.6892	Remote Similarity	NPD5691	Approved
0.6892	Remote Similarity	NPD5585	Approved
0.6879	Remote Similarity	NPD447	Suspended
0.6875	Remote Similarity	NPD6004	Phase 3
0.6875	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6005	Phase 3
0.6875	Remote Similarity	NPD6002	Phase 3
0.6864	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5647	Approved
0.6854	Remote Similarity	NPD6559	Discontinued
0.6853	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7003	Approved
0.6846	Remote Similarity	NPD17	Approved
0.6832	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2182	Approved
0.6828	Remote Similarity	NPD1241	Discontinued
0.6824	Remote Similarity	NPD2296	Approved
0.6824	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4140	Approved
0.6813	Remote Similarity	NPD1551	Phase 2
0.6805	Remote Similarity	NPD6801	Discontinued
0.68	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD411	Approved
0.6788	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6355	Discontinued
0.6766	Remote Similarity	NPD7239	Suspended
0.6761	Remote Similarity	NPD7473	Discontinued
0.6755	Remote Similarity	NPD1281	Approved
0.675	Remote Similarity	NPD3748	Approved
0.6748	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4110	Phase 3
0.6746	Remote Similarity	NPD5889	Approved
0.6746	Remote Similarity	NPD5890	Approved
0.6744	Remote Similarity	NPD7075	Discontinued
0.6733	Remote Similarity	NPD1778	Approved
0.6726	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3817	Phase 2
0.6711	Remote Similarity	NPD1608	Approved
0.6709	Remote Similarity	NPD4307	Phase 2
0.6707	Remote Similarity	NPD3887	Approved
0.6689	Remote Similarity	NPD3496	Discontinued
0.6688	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1203	Approved
0.6686	Remote Similarity	NPD3882	Suspended
0.6686	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6232	Discontinued
0.6686	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD5327	Phase 3
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4359	Approved
0.6646	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6959	Discontinued
0.6626	Remote Similarity	NPD1549	Phase 2
0.6623	Remote Similarity	NPD4626	Approved
0.6623	Remote Similarity	NPD1283	Approved
0.661	Remote Similarity	NPD2403	Approved
0.6605	Remote Similarity	NPD2531	Phase 2
0.6605	Remote Similarity	NPD2438	Suspended
0.6604	Remote Similarity	NPD3142	Approved
0.6604	Remote Similarity	NPD3140	Approved
0.6591	Remote Similarity	NPD5710	Approved
0.6591	Remote Similarity	NPD5711	Approved
0.659	Remote Similarity	NPD7768	Phase 2
0.6588	Remote Similarity	NPD6585	Discontinued
0.6581	Remote Similarity	NPD2797	Approved
0.6579	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3134	Approved
0.6564	Remote Similarity	NPD5762	Approved
0.6564	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2353	Approved
0.6564	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5763	Approved
0.6564	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4622	Approved
0.6562	Remote Similarity	NPD4618	Approved
0.6556	Remote Similarity	NPD1651	Approved
0.655	Remote Similarity	NPD8404	Phase 2
0.6549	Remote Similarity	NPD164	Approved
0.6545	Remote Similarity	NPD3750	Approved
0.6543	Remote Similarity	NPD7033	Discontinued
0.6543	Remote Similarity	NPD1510	Phase 2
0.6543	Remote Similarity	NPD4308	Phase 3
0.6541	Remote Similarity	NPD6663	Approved
0.6536	Remote Similarity	NPD7799	Discontinued
0.6536	Remote Similarity	NPD3818	Discontinued
0.6534	Remote Similarity	NPD7199	Phase 2
0.6532	Remote Similarity	NPD5402	Approved
0.6522	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1607	Approved
0.6522	Remote Similarity	NPD6653	Approved
0.6522	Remote Similarity	NPD6651	Approved
0.6519	Remote Similarity	NPD5953	Discontinued
0.6519	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1934	Approved
0.6509	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4477	Approved
0.6503	Remote Similarity	NPD8313	Approved
0.6503	Remote Similarity	NPD4476	Approved
0.6503	Remote Similarity	NPD8312	Approved
0.65	Remote Similarity	NPD7286	Phase 2
0.65	Remote Similarity	NPD5844	Phase 1
0.65	Remote Similarity	NPD1240	Approved
0.6497	Remote Similarity	NPD9494	Approved
0.6497	Remote Similarity	NPD7315	Approved
0.6494	Remote Similarity	NPD7057	Phase 3
0.6494	Remote Similarity	NPD7058	Phase 2
0.6491	Remote Similarity	NPD4380	Phase 2
0.649	Remote Similarity	NPD9545	Approved
0.6488	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5689	Approved
0.6481	Remote Similarity	NPD5688	Approved
0.6478	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3764	Approved
0.6474	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2801	Approved
0.6474	Remote Similarity	NPD6362	Approved
0.6467	Remote Similarity	NPD9493	Approved
0.6463	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4107	Approved
0.6457	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3024	Approved
0.6447	Remote Similarity	NPD3025	Approved
0.6446	Remote Similarity	NPD8166	Discontinued
0.6438	Remote Similarity	NPD4870	Approved
0.6438	Remote Similarity	NPD7961	Discontinued
0.6437	Remote Similarity	NPD5978	Approved
0.6437	Remote Similarity	NPD5977	Approved
0.6436	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1611	Approved
0.6429	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6353	Approved
0.6416	Remote Similarity	NPD6844	Discontinued
0.6414	Remote Similarity	NPD1358	Approved
0.6412	Remote Similarity	NPD5403	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