NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	254.868
LogP:	2.414
LogD:	2.821
LogS:	-3.231
# Rotatable Bonds:	0
TPSA:	45.9
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	5.326
Fsp3:	0.733
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:	-4.6
MDCK Permeability:	2.278098872920964e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.906
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.542
30% Bioavailability (F30%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.717
Plasma Protein Binding (PPB):	83.74275970458984%
Volume Distribution (VD):	2.516
Pgp-substrate:	25.56409454345703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.267
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.76
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	12.951
Half-life (T1/2):	0.547

ADMET: Toxicity

hERG Blockers:	0.239
Human Hepatotoxicity (H-HT):	0.424
Drug-inuced Liver Injury (DILI):	0.336
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.348
Carcinogencity:	0.946
Eye Corrosion:	0.009
Eye Irritation:	0.038
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC97904

Natural Product ID:	NPC97904
*Common Name:**	UYVZYGGRZXBGRY-IJSGKQKWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UYVZYGGRZXBGRY-IJSGKQKWSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-7-17-10-6-15-11(18-15)5-4-9(2)14(15,3)13(16)12(8)10/h7,9,11,13,16H,4-6H2,1-3H3/t9-,11-,13+,14-,15-/m0/s1
SMILES:	Cc1coc2C[C@]34[C@H](CC[C@H](C)[C@@]3(C)[C@@H](c12)O)O4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400342
PubChem CID:	44445651
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]
NPO1183	Ligularia macrophylla	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	>=	20.0	ug.mL-1	PMID[568408]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	>=	20.0	ug.mL-1	PMID[568408]

☑ 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 NPC97904 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	348
0.1-0.2	1385
0.2-0.3	2990
0.3-0.4	6387
0.4-0.5	11909
0.5-0.6	7187
0.6-0.7	7994
0.7-0.8	4378
0.8-0.85	105
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC64568
0.9517	High Similarity	NPC114880
0.9241	High Similarity	NPC211625
0.9172	High Similarity	NPC19747
0.9091	High Similarity	NPC205071
0.9054	High Similarity	NPC475777
0.8933	High Similarity	NPC75310
0.8904	High Similarity	NPC62799
0.8889	High Similarity	NPC20578
0.8889	High Similarity	NPC62103
0.8808	High Similarity	NPC472785
0.8767	High Similarity	NPC84479
0.8758	High Similarity	NPC474611
0.863	High Similarity	NPC263337
0.8621	High Similarity	NPC61157
0.8621	High Similarity	NPC18904
0.8621	High Similarity	NPC473681
0.8621	High Similarity	NPC218204
0.8611	High Similarity	NPC471996
0.8609	High Similarity	NPC472787
0.859	High Similarity	NPC288602
0.859	High Similarity	NPC88841
0.8581	High Similarity	NPC41182
0.8571	High Similarity	NPC304692
0.8571	High Similarity	NPC243577
0.8553	High Similarity	NPC75906
0.8543	High Similarity	NPC212257
0.8542	High Similarity	NPC4764
0.8526	High Similarity	NPC18986
0.8526	High Similarity	NPC188649
0.8516	High Similarity	NPC140952
0.8506	High Similarity	NPC104736
0.8506	High Similarity	NPC41880
0.8491	Intermediate Similarity	NPC296558
0.8481	Intermediate Similarity	NPC121995
0.8472	Intermediate Similarity	NPC46896
0.8471	Intermediate Similarity	NPC472783
0.8471	Intermediate Similarity	NPC472780
0.8452	Intermediate Similarity	NPC81405
0.8452	Intermediate Similarity	NPC194499
0.8446	Intermediate Similarity	NPC103134
0.8442	Intermediate Similarity	NPC42458
0.8442	Intermediate Similarity	NPC158261
0.8429	Intermediate Similarity	NPC329707
0.8428	Intermediate Similarity	NPC472784
0.8428	Intermediate Similarity	NPC136641
0.8408	Intermediate Similarity	NPC472782
0.8408	Intermediate Similarity	NPC472781
0.8406	Intermediate Similarity	NPC178382
0.8397	Intermediate Similarity	NPC116639
0.8377	Intermediate Similarity	NPC57998
0.8377	Intermediate Similarity	NPC282445
0.8367	Intermediate Similarity	NPC67003
0.8365	Intermediate Similarity	NPC100849
0.8356	Intermediate Similarity	NPC472376
0.8355	Intermediate Similarity	NPC195325
0.8354	Intermediate Similarity	NPC283209
0.8344	Intermediate Similarity	NPC287559
0.8344	Intermediate Similarity	NPC221809
0.8333	Intermediate Similarity	NPC88007
0.8333	Intermediate Similarity	NPC472772
0.8333	Intermediate Similarity	NPC249021
0.8333	Intermediate Similarity	NPC5676
0.8333	Intermediate Similarity	NPC299038
0.8333	Intermediate Similarity	NPC195954
0.8333	Intermediate Similarity	NPC106247
0.8323	Intermediate Similarity	NPC35000
0.8323	Intermediate Similarity	NPC472786
0.8322	Intermediate Similarity	NPC476946
0.8312	Intermediate Similarity	NPC469503
0.8302	Intermediate Similarity	NPC56358
0.8291	Intermediate Similarity	NPC68848
0.8291	Intermediate Similarity	NPC5079
0.8276	Intermediate Similarity	NPC158525
0.8267	Intermediate Similarity	NPC476944
0.8264	Intermediate Similarity	NPC214097
0.8264	Intermediate Similarity	NPC293253
0.8258	Intermediate Similarity	NPC30222
0.8258	Intermediate Similarity	NPC178932
0.8239	Intermediate Similarity	NPC285567
0.8239	Intermediate Similarity	NPC234660
0.8239	Intermediate Similarity	NPC51568
0.8239	Intermediate Similarity	NPC39986
0.8239	Intermediate Similarity	NPC134254
0.8239	Intermediate Similarity	NPC302369
0.8235	Intermediate Similarity	NPC472654
0.8228	Intermediate Similarity	NPC335761
0.8217	Intermediate Similarity	NPC477674
0.8207	Intermediate Similarity	NPC471998
0.8205	Intermediate Similarity	NPC469336
0.8199	Intermediate Similarity	NPC473753
0.8199	Intermediate Similarity	NPC473766
0.8199	Intermediate Similarity	NPC270312
0.8194	Intermediate Similarity	NPC473131
0.8194	Intermediate Similarity	NPC121615
0.8194	Intermediate Similarity	NPC268905
0.8194	Intermediate Similarity	NPC470675
0.8194	Intermediate Similarity	NPC294511
0.8194	Intermediate Similarity	NPC471995
0.8188	Intermediate Similarity	NPC205765
0.8187	Intermediate Similarity	NPC476856
0.8187	Intermediate Similarity	NPC261184
0.8187	Intermediate Similarity	NPC476858
0.8187	Intermediate Similarity	NPC476857
0.8182	Intermediate Similarity	NPC228842
0.8182	Intermediate Similarity	NPC45947
0.8176	Intermediate Similarity	NPC193798
0.8176	Intermediate Similarity	NPC200782
0.8176	Intermediate Similarity	NPC79571
0.8176	Intermediate Similarity	NPC82851
0.8176	Intermediate Similarity	NPC472771
0.817	Intermediate Similarity	NPC66991
0.8165	Intermediate Similarity	NPC475967
0.8148	Intermediate Similarity	NPC471397
0.8146	Intermediate Similarity	NPC251865
0.8146	Intermediate Similarity	NPC158871
0.8137	Intermediate Similarity	NPC23387
0.8133	Intermediate Similarity	NPC121158
0.8133	Intermediate Similarity	NPC475519
0.8129	Intermediate Similarity	NPC18135
0.8125	Intermediate Similarity	NPC472773
0.8117	Intermediate Similarity	NPC125182
0.8117	Intermediate Similarity	NPC69647
0.8113	Intermediate Similarity	NPC25255
0.8113	Intermediate Similarity	NPC8389
0.8113	Intermediate Similarity	NPC472653
0.8113	Intermediate Similarity	NPC476350
0.8113	Intermediate Similarity	NPC476349
0.8108	Intermediate Similarity	NPC177262
0.8105	Intermediate Similarity	NPC250228
0.8105	Intermediate Similarity	NPC286038
0.8105	Intermediate Similarity	NPC255414
0.8101	Intermediate Similarity	NPC261597
0.8101	Intermediate Similarity	NPC164427
0.8101	Intermediate Similarity	NPC221992
0.8101	Intermediate Similarity	NPC187149
0.8098	Intermediate Similarity	NPC302392
0.8095	Intermediate Similarity	NPC214572
0.8089	Intermediate Similarity	NPC477669
0.8089	Intermediate Similarity	NPC469850
0.8086	Intermediate Similarity	NPC173516
0.8086	Intermediate Similarity	NPC476850
0.8086	Intermediate Similarity	NPC476853
0.8086	Intermediate Similarity	NPC476861
0.8086	Intermediate Similarity	NPC472282
0.8075	Intermediate Similarity	NPC271657
0.8075	Intermediate Similarity	NPC123088
0.8075	Intermediate Similarity	NPC476860
0.8075	Intermediate Similarity	NPC472664
0.8065	Intermediate Similarity	NPC476122
0.8065	Intermediate Similarity	NPC477404
0.8065	Intermediate Similarity	NPC196864
0.8063	Intermediate Similarity	NPC149896
0.8063	Intermediate Similarity	NPC117986
0.8063	Intermediate Similarity	NPC18347
0.8063	Intermediate Similarity	NPC329938
0.8054	Intermediate Similarity	NPC202260
0.8052	Intermediate Similarity	NPC245757
0.8052	Intermediate Similarity	NPC304351
0.805	Intermediate Similarity	NPC473368
0.805	Intermediate Similarity	NPC84349
0.805	Intermediate Similarity	NPC196448
0.805	Intermediate Similarity	NPC260902
0.805	Intermediate Similarity	NPC296957
0.805	Intermediate Similarity	NPC272196
0.8049	Intermediate Similarity	NPC475237
0.8049	Intermediate Similarity	NPC475641
0.8041	Intermediate Similarity	NPC286130
0.8041	Intermediate Similarity	NPC473268
0.8041	Intermediate Similarity	NPC310043
0.8039	Intermediate Similarity	NPC346
0.8038	Intermediate Similarity	NPC209364
0.8038	Intermediate Similarity	NPC107646
0.8038	Intermediate Similarity	NPC477687
0.8038	Intermediate Similarity	NPC477671
0.8038	Intermediate Similarity	NPC175192
0.8037	Intermediate Similarity	NPC160651
0.8037	Intermediate Similarity	NPC271235
0.8025	Intermediate Similarity	NPC475779
0.8013	Intermediate Similarity	NPC321896
0.8013	Intermediate Similarity	NPC52412
0.8013	Intermediate Similarity	NPC476185
0.8012	Intermediate Similarity	NPC663
0.8012	Intermediate Similarity	NPC224394
0.8012	Intermediate Similarity	NPC477405
0.8012	Intermediate Similarity	NPC269117
0.8	Intermediate Similarity	NPC148374
0.8	Intermediate Similarity	NPC472299
0.8	Intermediate Similarity	NPC90296
0.8	Intermediate Similarity	NPC470998
0.8	Intermediate Similarity	NPC477402
0.8	Intermediate Similarity	NPC61788
0.8	Intermediate Similarity	NPC226287
0.7988	Intermediate Similarity	NPC470995
0.7987	Intermediate Similarity	NPC472776
0.7987	Intermediate Similarity	NPC160015
0.7987	Intermediate Similarity	NPC286722
0.7987	Intermediate Similarity	NPC180924
0.7987	Intermediate Similarity	NPC247677
0.7987	Intermediate Similarity	NPC71821

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 NPC97904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	928
0.2-0.3	1877
0.3-0.4	2713
0.4-0.5	2077
0.5-0.6	883
0.6-0.7	315
0.7-0.8	47
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
0.8323	Intermediate Similarity	NPD5760	Phase 2
0.8323	Intermediate Similarity	NPD5761	Phase 2
0.7988	Intermediate Similarity	NPD8434	Phase 2
0.7829	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD920	Approved
0.7468	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1549	Phase 2
0.7403	Intermediate Similarity	NPD2796	Approved
0.7384	Intermediate Similarity	NPD6764	Approved
0.7384	Intermediate Similarity	NPD6765	Approved
0.7384	Intermediate Similarity	NPD6559	Discontinued
0.7378	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6959	Discontinued
0.7355	Intermediate Similarity	NPD1471	Phase 3
0.7355	Intermediate Similarity	NPD2344	Approved
0.7342	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6651	Approved
0.732	Intermediate Similarity	NPD1607	Approved
0.7317	Intermediate Similarity	NPD7819	Suspended
0.7308	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5494	Approved
0.7303	Intermediate Similarity	NPD1240	Approved
0.7289	Intermediate Similarity	NPD3749	Approved
0.7261	Intermediate Similarity	NPD1243	Approved
0.7256	Intermediate Similarity	NPD1934	Approved
0.725	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4380	Phase 2
0.7239	Intermediate Similarity	NPD6599	Discontinued
0.7229	Intermediate Similarity	NPD3882	Suspended
0.7226	Intermediate Similarity	NPD1510	Phase 2
0.7216	Intermediate Similarity	NPD6784	Approved
0.7216	Intermediate Similarity	NPD6785	Approved
0.7179	Intermediate Similarity	NPD1551	Phase 2
0.7171	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2309	Approved
0.716	Intermediate Similarity	NPD1247	Approved
0.7151	Intermediate Similarity	NPD3818	Discontinued
0.7118	Intermediate Similarity	NPD5710	Approved
0.7118	Intermediate Similarity	NPD5711	Approved
0.7108	Intermediate Similarity	NPD2801	Approved
0.7108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6273	Approved
0.7091	Intermediate Similarity	NPD7411	Suspended
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7083	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1511	Approved
0.7073	Intermediate Similarity	NPD3226	Approved
0.7048	Intermediate Similarity	NPD6801	Discontinued
0.7044	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD919	Approved
0.7035	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6166	Phase 2
0.7035	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2346	Discontinued
0.7011	Intermediate Similarity	NPD5844	Phase 1
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD7473	Discontinued
0.6994	Remote Similarity	NPD1512	Approved
0.698	Remote Similarity	NPD1608	Approved
0.6975	Remote Similarity	NPD6799	Approved
0.6954	Remote Similarity	NPD3751	Discontinued
0.6949	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD37	Approved
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8404	Phase 2
0.6923	Remote Similarity	NPD4967	Phase 2
0.6919	Remote Similarity	NPD6232	Discontinued
0.6919	Remote Similarity	NPD3787	Discontinued
0.6918	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6005	Phase 3
0.6918	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6004	Phase 3
0.6918	Remote Similarity	NPD6002	Phase 3
0.6914	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3750	Approved
0.6879	Remote Similarity	NPD3926	Phase 2
0.6875	Remote Similarity	NPD7074	Phase 3
0.6867	Remote Similarity	NPD3972	Approved
0.6867	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3817	Phase 2
0.6864	Remote Similarity	NPD5402	Approved
0.6855	Remote Similarity	NPD2935	Discontinued
0.6839	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2313	Discontinued
0.6831	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7768	Phase 2
0.6818	Remote Similarity	NPD7054	Approved
0.681	Remote Similarity	NPD7236	Approved
0.68	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7472	Approved
0.6779	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD17	Approved
0.6761	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5403	Approved
0.6744	Remote Similarity	NPD6234	Discontinued
0.6742	Remote Similarity	NPD6797	Phase 2
0.674	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2797	Approved
0.6731	Remote Similarity	NPD3268	Approved
0.6724	Remote Similarity	NPD7229	Phase 3
0.6722	Remote Similarity	NPD8313	Approved
0.6722	Remote Similarity	NPD8312	Approved
0.6709	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5124	Phase 1
0.6704	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7251	Discontinued
0.6688	Remote Similarity	NPD2798	Approved
0.6687	Remote Similarity	NPD3748	Approved
0.6687	Remote Similarity	NPD7003	Approved
0.6683	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7808	Phase 3
0.6648	Remote Similarity	NPD5953	Discontinued
0.6648	Remote Similarity	NPD2403	Approved
0.6648	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6279	Approved
0.6647	Remote Similarity	NPD6280	Approved
0.6646	Remote Similarity	NPD4140	Approved
0.6645	Remote Similarity	NPD9717	Approved
0.6629	Remote Similarity	NPD7286	Phase 2
0.6627	Remote Similarity	NPD5401	Approved
0.6624	Remote Similarity	NPD3764	Approved
0.6623	Remote Similarity	NPD1203	Approved
0.6608	Remote Similarity	NPD1465	Phase 2
0.6607	Remote Similarity	NPD7239	Suspended
0.6604	Remote Similarity	NPD447	Suspended
0.6604	Remote Similarity	NPD230	Phase 1
0.6603	Remote Similarity	NPD6832	Phase 2
0.6601	Remote Similarity	NPD4749	Approved
0.66	Remote Similarity	NPD4665	Approved
0.6588	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4308	Phase 3
0.6582	Remote Similarity	NPD8032	Phase 2
0.6581	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6779	Approved
0.6579	Remote Similarity	NPD6781	Approved
0.6579	Remote Similarity	NPD6780	Approved
0.6579	Remote Similarity	NPD6782	Approved
0.6579	Remote Similarity	NPD6776	Approved
0.6579	Remote Similarity	NPD1201	Approved
0.6579	Remote Similarity	NPD6778	Approved
0.6579	Remote Similarity	NPD1610	Phase 2
0.6579	Remote Similarity	NPD6777	Approved
0.6578	Remote Similarity	NPD4363	Phase 3
0.6578	Remote Similarity	NPD4360	Phase 2
0.6573	Remote Similarity	NPD7799	Discontinued
0.6573	Remote Similarity	NPD7228	Approved
0.6571	Remote Similarity	NPD7199	Phase 2
0.6566	Remote Similarity	NPD7390	Discontinued
0.6561	Remote Similarity	NPD4625	Phase 3
0.6558	Remote Similarity	NPD1876	Approved
0.6558	Remote Similarity	NPD1283	Approved
0.6543	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4361	Phase 2
0.6541	Remote Similarity	NPD4287	Approved
0.6538	Remote Similarity	NPD9494	Approved
0.6538	Remote Similarity	NPD2861	Phase 2
0.6534	Remote Similarity	NPD6808	Phase 2
0.6533	Remote Similarity	NPD9545	Approved
0.6531	Remote Similarity	NPD1241	Discontinued
0.6527	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2654	Approved
0.6522	Remote Similarity	NPD8150	Discontinued
0.6519	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD411	Approved
0.6519	Remote Similarity	NPD7685	Pre-registration
0.6516	Remote Similarity	NPD1470	Approved
0.651	Remote Similarity	NPD3057	Approved
0.6503	Remote Similarity	NPD8407	Phase 2
0.65	Remote Similarity	NPD6355	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