NPASS Compound

Structure

NPC75310 OpenBabel07101719122D 25 27 0 0 1 0 0 0 0 0999 V2000 -3.3404 -2.8929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -3.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1832 -2.1322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 -3.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6702 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6702 0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1541 0.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6702 -2.8929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -0.2980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -0.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8351 1.4464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6702 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8351 1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6702 0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -0.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6702 -1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8351 2.4107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 2.4107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 -1.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 1.2623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -1.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 6 10 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 11 2 0 0 0 0 9 24 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 12 20 1 6 0 0 0 13 15 1 0 0 0 0 13 21 1 1 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 6 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	359.576
LogP:	3.129
LogD:	3.461
LogS:	-3.845
# Rotatable Bonds:	3
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	4.718
Fsp3:	0.6
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:	-4.652
MDCK Permeability:	2.5531024220981635e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.214
30% Bioavailability (F30%):	0.814

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.396
Plasma Protein Binding (PPB):	85.76558685302734%
Volume Distribution (VD):	2.906
Pgp-substrate:	15.331721305847168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.802
CYP1A2-substrate:	0.782
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.623
CYP2C9-inhibitor:	0.883
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.302
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.416

ADMET: Excretion

Clearance (CL):	11.458
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.666
Drug-inuced Liver Injury (DILI):	0.205
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.272
Skin Sensitization:	0.247
Carcinogencity:	0.236
Eye Corrosion:	0.031
Eye Irritation:	0.025
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC75310

Natural Product ID:	NPC75310
*Common Name:**	6Beta-Angeloyloxy-1Alpha-Hydroxy-10Alpha-H-9-Oxofuranoeremophilane
IUPAC Name:	[(4S,4aR,5S,8S,8aS)-8-hydroxy-3,4a,5-trimethyl-9-oxo-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	FEVYLFPXBKQRPU-YZXFFQNQSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-6-10(2)19(23)25-18-14-11(3)9-24-17(14)16(22)15-13(21)8-7-12(4)20(15,18)5/h6,9,12-13,15,18,21H,7-8H2,1-5H3/b10-6-/t12-,13-,15-,18+,20+/m0/s1
SMILES:	C/C=C(C(=O)O[C@@H]1c2c(C)coc2C(=O)[C@H]2[C@@]1(C)[C@@H](C)CC[C@@H]2O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458911
PubChem CID:	11739482
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO28122	Senecio chionophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387646]
NPO28122	Senecio chionophilus	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	114.0	ug.mL-1	PMID[503211]

☑ 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 NPC75310 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	328
0.1-0.2	1278
0.2-0.3	2832
0.3-0.4	5788
0.4-0.5	10927
0.5-0.6	8662
0.6-0.7	7063
0.7-0.8	5417
0.8-0.85	324
0.85-0.9	71
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC475777
0.9524	High Similarity	NPC211625
0.94	High Similarity	NPC114880
0.932	High Similarity	NPC62799
0.9195	High Similarity	NPC19747
0.9156	High Similarity	NPC474611
0.9116	High Similarity	NPC64568
0.9085	High Similarity	NPC472785
0.9038	High Similarity	NPC18986
0.9032	High Similarity	NPC140952
0.8987	High Similarity	NPC121995
0.8987	High Similarity	NPC475779
0.8986	High Similarity	NPC205071
0.8968	High Similarity	NPC81405
0.8968	High Similarity	NPC304692
0.8933	High Similarity	NPC97904
0.8931	High Similarity	NPC472784
0.8926	High Similarity	NPC84479
0.8903	High Similarity	NPC41880
0.8903	High Similarity	NPC104736
0.8896	High Similarity	NPC178932
0.8889	High Similarity	NPC472787
0.8861	High Similarity	NPC472783
0.8861	High Similarity	NPC472780
0.8854	High Similarity	NPC287559
0.8846	High Similarity	NPC472772
0.8839	High Similarity	NPC469336
0.8831	High Similarity	NPC75906
0.8824	High Similarity	NPC212257
0.8812	High Similarity	NPC473766
0.8812	High Similarity	NPC473753
0.8805	High Similarity	NPC476858
0.8805	High Similarity	NPC476856
0.8805	High Similarity	NPC476857
0.8805	High Similarity	NPC56358
0.8805	High Similarity	NPC261184
0.8797	High Similarity	NPC188649
0.8797	High Similarity	NPC69028
0.8797	High Similarity	NPC472781
0.8797	High Similarity	NPC472782
0.8758	High Similarity	NPC195325
0.875	High Similarity	NPC23387
0.8742	High Similarity	NPC288602
0.8742	High Similarity	NPC477405
0.8742	High Similarity	NPC88841
0.8742	High Similarity	NPC283209
0.8742	High Similarity	NPC41182
0.8734	High Similarity	NPC25255
0.8733	High Similarity	NPC243577
0.8726	High Similarity	NPC249021
0.8726	High Similarity	NPC194499
0.8718	High Similarity	NPC472786
0.871	High Similarity	NPC469503
0.8696	High Similarity	NPC476853
0.8696	High Similarity	NPC476850
0.8696	High Similarity	NPC476861
0.8696	High Similarity	NPC472775
0.8696	High Similarity	NPC472774
0.8696	High Similarity	NPC270312
0.8688	High Similarity	NPC276551
0.8688	High Similarity	NPC472664
0.8688	High Similarity	NPC123088
0.8688	High Similarity	NPC476860
0.8684	High Similarity	NPC262198
0.8679	High Similarity	NPC472771
0.8679	High Similarity	NPC329938
0.8679	High Similarity	NPC5079
0.8679	High Similarity	NPC68848
0.8679	High Similarity	NPC193798
0.8671	High Similarity	NPC477403
0.8671	High Similarity	NPC475967
0.8671	High Similarity	NPC473368
0.8642	High Similarity	NPC296558
0.8642	High Similarity	NPC471397
0.8636	High Similarity	NPC472654
0.8634	High Similarity	NPC470875
0.8625	High Similarity	NPC292389
0.8625	High Similarity	NPC134254
0.8625	High Similarity	NPC285567
0.8625	High Similarity	NPC469338
0.8625	High Similarity	NPC224394
0.8625	High Similarity	NPC472773
0.8625	High Similarity	NPC234660
0.8625	High Similarity	NPC39986
0.8625	High Similarity	NPC663
0.8625	High Similarity	NPC302369
0.8625	High Similarity	NPC51568
0.8616	High Similarity	NPC477402
0.8616	High Similarity	NPC335761
0.8616	High Similarity	NPC333139
0.8608	High Similarity	NPC88007
0.8608	High Similarity	NPC195954
0.8608	High Similarity	NPC472283
0.8599	High Similarity	NPC35000
0.859	High Similarity	NPC246164
0.859	High Similarity	NPC121615
0.859	High Similarity	NPC294511
0.8581	High Similarity	NPC196864
0.8581	High Similarity	NPC469335
0.8581	High Similarity	NPC477404
0.8581	High Similarity	NPC159927
0.858	High Similarity	NPC173516
0.858	High Similarity	NPC472282
0.8571	High Similarity	NPC469849
0.8571	High Similarity	NPC470940
0.8562	High Similarity	NPC82851
0.8562	High Similarity	NPC263432
0.8562	High Similarity	NPC470939
0.8554	High Similarity	NPC472665
0.8553	High Similarity	NPC476944
0.8553	High Similarity	NPC116639
0.8544	High Similarity	NPC60973
0.8544	High Similarity	NPC263265
0.8535	High Similarity	NPC282445
0.8535	High Similarity	NPC30222
0.8533	High Similarity	NPC18904
0.8533	High Similarity	NPC473681
0.8533	High Similarity	NPC218204
0.8533	High Similarity	NPC61157
0.8533	High Similarity	NPC148374
0.8528	High Similarity	NPC160651
0.85	High Similarity	NPC191828
0.85	High Similarity	NPC472653
0.8491	Intermediate Similarity	NPC261597
0.8487	Intermediate Similarity	NPC267632
0.8481	Intermediate Similarity	NPC44675
0.8481	Intermediate Similarity	NPC264943
0.8481	Intermediate Similarity	NPC88958
0.8481	Intermediate Similarity	NPC214541
0.8476	Intermediate Similarity	NPC302392
0.8462	Intermediate Similarity	NPC228842
0.8447	Intermediate Similarity	NPC117986
0.8447	Intermediate Similarity	NPC472767
0.8447	Intermediate Similarity	NPC79571
0.8442	Intermediate Similarity	NPC233763
0.8438	Intermediate Similarity	NPC237155
0.8435	Intermediate Similarity	NPC293253
0.8431	Intermediate Similarity	NPC251865
0.8428	Intermediate Similarity	NPC107646
0.8428	Intermediate Similarity	NPC469485
0.8428	Intermediate Similarity	NPC209364
0.8424	Intermediate Similarity	NPC475237
0.8424	Intermediate Similarity	NPC475641
0.8421	Intermediate Similarity	NPC62103
0.8421	Intermediate Similarity	NPC20578
0.8421	Intermediate Similarity	NPC263337
0.8421	Intermediate Similarity	NPC121158
0.8418	Intermediate Similarity	NPC57998
0.8415	Intermediate Similarity	NPC271235
0.8408	Intermediate Similarity	NPC272590
0.8405	Intermediate Similarity	NPC149945
0.84	Intermediate Similarity	NPC471996
0.84	Intermediate Similarity	NPC177262
0.8397	Intermediate Similarity	NPC69647
0.8397	Intermediate Similarity	NPC125182
0.8395	Intermediate Similarity	NPC14499
0.8395	Intermediate Similarity	NPC475039
0.8395	Intermediate Similarity	NPC419
0.8395	Intermediate Similarity	NPC476035
0.8387	Intermediate Similarity	NPC286038
0.8387	Intermediate Similarity	NPC255414
0.8387	Intermediate Similarity	NPC221809
0.8387	Intermediate Similarity	NPC250228
0.8387	Intermediate Similarity	NPC71821
0.8385	Intermediate Similarity	NPC8389
0.8385	Intermediate Similarity	NPC305016
0.8385	Intermediate Similarity	NPC472299
0.8383	Intermediate Similarity	NPC167340
0.8378	Intermediate Similarity	NPC471998
0.8375	Intermediate Similarity	NPC472778
0.8375	Intermediate Similarity	NPC472777
0.8375	Intermediate Similarity	NPC45101
0.8375	Intermediate Similarity	NPC36655
0.8375	Intermediate Similarity	NPC472776
0.8375	Intermediate Similarity	NPC167142
0.8375	Intermediate Similarity	NPC299038
0.8375	Intermediate Similarity	NPC173544
0.8375	Intermediate Similarity	NPC286722
0.8375	Intermediate Similarity	NPC187149
0.8365	Intermediate Similarity	NPC281258
0.8365	Intermediate Similarity	NPC469850
0.8365	Intermediate Similarity	NPC92979
0.8364	Intermediate Similarity	NPC470995
0.8364	Intermediate Similarity	NPC44602
0.8354	Intermediate Similarity	NPC478179
0.8354	Intermediate Similarity	NPC472651
0.8344	Intermediate Similarity	NPC476122
0.8344	Intermediate Similarity	NPC202260
0.8344	Intermediate Similarity	NPC271657
0.8333	Intermediate Similarity	NPC18347
0.8333	Intermediate Similarity	NPC149896
0.8333	Intermediate Similarity	NPC200782
0.8333	Intermediate Similarity	NPC66991
0.8333	Intermediate Similarity	NPC6326
0.8333	Intermediate Similarity	NPC96443
0.8333	Intermediate Similarity	NPC290400
0.8333	Intermediate Similarity	NPC197596
0.8323	Intermediate Similarity	NPC473473
0.8323	Intermediate Similarity	NPC475295
0.8323	Intermediate Similarity	NPC307383

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 NPC75310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	888
0.2-0.3	1888
0.3-0.4	2605
0.4-0.5	2072
0.5-0.6	998
0.6-0.7	331
0.7-0.8	86
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
0.8616	High Similarity	NPD5537	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD8434	Phase 2
0.8137	Intermediate Similarity	NPD5760	Phase 2
0.8137	Intermediate Similarity	NPD5761	Phase 2
0.8059	Intermediate Similarity	NPD6765	Approved
0.8059	Intermediate Similarity	NPD6764	Approved
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7874	Intermediate Similarity	NPD6785	Approved
0.7874	Intermediate Similarity	NPD6784	Approved
0.7871	Intermediate Similarity	NPD1471	Phase 3
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD920	Approved
0.7756	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD7819	Suspended
0.7688	Intermediate Similarity	NPD6799	Approved
0.7665	Intermediate Similarity	NPD7075	Discontinued
0.7658	Intermediate Similarity	NPD2800	Approved
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6801	Discontinued
0.7633	Intermediate Similarity	NPD1247	Approved
0.7619	Intermediate Similarity	NPD919	Approved
0.7576	Intermediate Similarity	NPD7411	Suspended
0.7561	Intermediate Similarity	NPD3226	Approved
0.7547	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD6559	Discontinued
0.7531	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3882	Suspended
0.7456	Intermediate Similarity	NPD3749	Approved
0.744	Intermediate Similarity	NPD3817	Phase 2
0.744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5402	Approved
0.7438	Intermediate Similarity	NPD1243	Approved
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2346	Discontinued
0.7407	Intermediate Similarity	NPD7236	Approved
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7378	Intermediate Similarity	NPD6273	Approved
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5494	Approved
0.7358	Intermediate Similarity	NPD2796	Approved
0.7358	Intermediate Similarity	NPD1551	Phase 2
0.7333	Intermediate Similarity	NPD5403	Approved
0.7317	Intermediate Similarity	NPD5401	Approved
0.7314	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD5711	Approved
0.7278	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5844	Phase 1
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1549	Phase 2
0.7245	Intermediate Similarity	NPD8404	Phase 2
0.7244	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2313	Discontinued
0.7225	Intermediate Similarity	NPD6959	Discontinued
0.7216	Intermediate Similarity	NPD3818	Discontinued
0.7205	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2344	Approved
0.7205	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4380	Phase 2
0.7193	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7239	Suspended
0.7178	Intermediate Similarity	NPD3750	Approved
0.7175	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7473	Discontinued
0.7151	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD6100	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7799	Discontinued
0.7118	Intermediate Similarity	NPD37	Approved
0.7118	Intermediate Similarity	NPD1934	Approved
0.7111	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7102	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6166	Phase 2
0.7102	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6004	Phase 3
0.7099	Intermediate Similarity	NPD6005	Phase 3
0.7099	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7768	Phase 2
0.7093	Intermediate Similarity	NPD4966	Approved
0.7093	Intermediate Similarity	NPD4965	Approved
0.7093	Intermediate Similarity	NPD4967	Phase 2
0.7088	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6808	Phase 2
0.7086	Intermediate Similarity	NPD6232	Discontinued
0.7081	Intermediate Similarity	NPD3748	Approved
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.7081	Intermediate Similarity	NPD1510	Phase 2
0.7073	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1607	Approved
0.7063	Intermediate Similarity	NPD6651	Approved
0.7059	Intermediate Similarity	NPD1608	Approved
0.7044	Intermediate Similarity	NPD1240	Approved
0.7033	Intermediate Similarity	NPD8407	Phase 2
0.703	Intermediate Similarity	NPD2309	Approved
0.7029	Intermediate Similarity	NPD8127	Discontinued
0.7022	Intermediate Similarity	NPD3751	Discontinued
0.7006	Intermediate Similarity	NPD2403	Approved
0.7006	Intermediate Similarity	NPD6832	Phase 2
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6994	Remote Similarity	NPD5763	Approved
0.6994	Remote Similarity	NPD5762	Approved
0.6989	Remote Similarity	NPD3787	Discontinued
0.6989	Remote Similarity	NPD7229	Phase 3
0.6978	Remote Similarity	NPD8313	Approved
0.6978	Remote Similarity	NPD8312	Approved
0.6977	Remote Similarity	NPD2801	Approved
0.6964	Remote Similarity	NPD1512	Approved
0.6961	Remote Similarity	NPD8368	Discontinued
0.6961	Remote Similarity	NPD7251	Discontinued
0.6949	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD3266	Approved
0.6923	Remote Similarity	NPD3267	Approved
0.6923	Remote Similarity	NPD7808	Phase 3
0.6914	Remote Similarity	NPD6234	Discontinued
0.6906	Remote Similarity	NPD5953	Discontinued
0.6897	Remote Similarity	NPD7058	Phase 2
0.6897	Remote Similarity	NPD7057	Phase 3
0.6894	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7435	Discontinued
0.6889	Remote Similarity	NPD7286	Phase 2
0.6879	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7003	Approved
0.6865	Remote Similarity	NPD8150	Discontinued
0.6863	Remote Similarity	NPD17	Approved
0.6851	Remote Similarity	NPD7074	Phase 3
0.6845	Remote Similarity	NPD1511	Approved
0.6839	Remote Similarity	NPD9717	Approved
0.6839	Remote Similarity	NPD3972	Approved
0.6836	Remote Similarity	NPD7199	Phase 2
0.6832	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4140	Approved
0.6831	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3887	Approved
0.6824	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1203	Approved
0.6815	Remote Similarity	NPD2797	Approved
0.6813	Remote Similarity	NPD3764	Approved
0.6813	Remote Similarity	NPD6798	Discontinued
0.6796	Remote Similarity	NPD7054	Approved
0.679	Remote Similarity	NPD447	Suspended
0.679	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.679	Remote Similarity	NPD230	Phase 1
0.679	Remote Similarity	NPD5124	Phase 1
0.6782	Remote Similarity	NPD1465	Phase 2
0.6772	Remote Similarity	NPD2798	Approved
0.677	Remote Similarity	NPD8032	Phase 2
0.677	Remote Similarity	NPD6233	Phase 2
0.6768	Remote Similarity	NPD4308	Phase 3
0.6766	Remote Similarity	NPD4110	Phase 3
0.6766	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7472	Approved
0.6753	Remote Similarity	NPD1778	Approved
0.674	Remote Similarity	NPD7228	Approved
0.674	Remote Similarity	NPD2163	Approved
0.6736	Remote Similarity	NPD6777	Approved
0.6736	Remote Similarity	NPD6778	Approved
0.6736	Remote Similarity	NPD6779	Approved
0.6736	Remote Similarity	NPD6776	Approved
0.6736	Remote Similarity	NPD6780	Approved
0.6736	Remote Similarity	NPD6782	Approved
0.6736	Remote Similarity	NPD6781	Approved
0.6736	Remote Similarity	NPD4107	Approved
0.6728	Remote Similarity	NPD4060	Phase 1
0.6726	Remote Similarity	NPD6190	Approved
0.6726	Remote Similarity	NPD2354	Approved
0.6722	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD411	Approved
0.6702	Remote Similarity	NPD4287	Approved
0.6702	Remote Similarity	NPD8435	Approved
0.6699	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7874	Approved
0.6683	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9092	Discovery
0.6667	Remote Similarity	NPD5890	Approved
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD3057	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