NPASS Compound

Structure

CID247136 OpenBabel06191716052D 24 27 0 0 0 0 0 0 0 0999 V2000 2.1661 2.8754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2556 -2.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7290 0.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3648 -1.8536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9530 -1.3773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6122 -1.7745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8981 -0.1246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0321 -0.6246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1359 -1.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8981 0.8754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1661 -0.1246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2150 -0.4337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4079 -1.2524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0321 1.3754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1661 0.8754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6272 0.3754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0976 -0.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7641 1.3754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0572 -2.1889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0321 2.3754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0484 -1.0341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8350 0.5503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2150 1.1844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	322.581
LogP:	3.676
LogD:	3.141
LogS:	-4.468
# Rotatable Bonds:	3
TPSA:	81.29
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.765
Synthetic Accessibility Score:	3.003
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.93
MDCK Permeability:	1.510763104306534e-05
Pgp-inhibitor:	0.874
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	89.32052612304688%
Volume Distribution (VD):	0.755
Pgp-substrate:	16.228872299194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.8
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.279
CYP2C19-substrate:	0.701
CYP2C9-inhibitor:	0.539
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.622
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	8.21
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.584
Rat Oral Acute Toxicity:	0.57
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.776
Carcinogencity:	0.103
Eye Corrosion:	0.004
Eye Irritation:	0.522
Respiratory Toxicity:	0.372

Download Data

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

Natural Product: NPC247136

Natural Product ID:	NPC247136
*Common Name:**	Bussealin E
IUPAC Name:	n.a.
Synonyms:	Bussealin E
Standard InCHIKey:	FMAUKBYYDCNROF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-21-14-10(19)7-8-5-4-6-9-12-11(8)15(14)24-16(12)18(23-3)17(22-2)13(9)20/h7,19-20H,4-6H2,1-3H3
SMILES:	COc1c(cc2CCCc3c4c2c1oc4c(c(c3O)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631159
PubChem CID:	50900323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0000015] Dibenzofurans

*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
NPO11403	Bussea sakalava	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[20942441]
NPO11403	Bussea sakalava	Species	Fabaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	45000.0	nM	PMID[488856]

☑ 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 NPC247136 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	445
0.1-0.2	1991
0.2-0.3	4713
0.3-0.4	11270
0.4-0.5	6509
0.5-0.6	3869
0.6-0.7	5135
0.7-0.8	5720
0.8-0.85	1686
0.85-0.9	1033
0.9-0.95	315
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC133065
0.9563	High Similarity	NPC45449
0.9563	High Similarity	NPC36320
0.9563	High Similarity	NPC39306
0.95	High Similarity	NPC59295
0.95	High Similarity	NPC263092
0.95	High Similarity	NPC1755
0.95	High Similarity	NPC39305
0.95	High Similarity	NPC1706
0.9437	High Similarity	NPC312056
0.9437	High Similarity	NPC238995
0.9437	High Similarity	NPC84515
0.9437	High Similarity	NPC272722
0.9375	High Similarity	NPC188486
0.9371	High Similarity	NPC196879
0.9333	High Similarity	NPC216842
0.9333	High Similarity	NPC476640
0.9333	High Similarity	NPC82217
0.9277	High Similarity	NPC287243
0.9273	High Similarity	NPC54098
0.9273	High Similarity	NPC230619
0.925	High Similarity	NPC195832
0.925	High Similarity	NPC16935
0.9245	High Similarity	NPC45131
0.9226	High Similarity	NPC476273
0.9222	High Similarity	NPC8127
0.9222	High Similarity	NPC49667
0.9217	High Similarity	NPC30550
0.9212	High Similarity	NPC476641
0.9207	High Similarity	NPC247973
0.9187	High Similarity	NPC241904
0.9187	High Similarity	NPC300727
0.9141	High Similarity	NPC475985
0.913	High Similarity	NPC476242
0.9125	High Similarity	NPC472461
0.9125	High Similarity	NPC274730
0.9102	High Similarity	NPC65885
0.9102	High Similarity	NPC149846
0.9091	High Similarity	NPC470704
0.9085	High Similarity	NPC37183
0.9085	High Similarity	NPC291110
0.9085	High Similarity	NPC326520
0.9074	High Similarity	NPC14353
0.9074	High Similarity	NPC228785
0.9074	High Similarity	NPC246478
0.9074	High Similarity	NPC56085
0.9068	High Similarity	NPC235215
0.9068	High Similarity	NPC101830
0.9068	High Similarity	NPC7973
0.9068	High Similarity	NPC203891
0.9068	High Similarity	NPC78302
0.9068	High Similarity	NPC472438
0.9068	High Similarity	NPC29841
0.9068	High Similarity	NPC110070
0.9064	High Similarity	NPC476170
0.9057	High Similarity	NPC125300
0.9053	High Similarity	NPC23553
0.9053	High Similarity	NPC77179
0.9048	High Similarity	NPC227906
0.9042	High Similarity	NPC174700
0.903	High Similarity	NPC277480
0.903	High Similarity	NPC170245
0.9024	High Similarity	NPC270837
0.9018	High Similarity	NPC40491
0.9018	High Similarity	NPC278052
0.9018	High Similarity	NPC61010
0.9012	High Similarity	NPC25495
0.9012	High Similarity	NPC253634
0.9012	High Similarity	NPC261004
0.9012	High Similarity	NPC105242
0.9012	High Similarity	NPC191459
0.9012	High Similarity	NPC100123
0.9012	High Similarity	NPC300943
0.9012	High Similarity	NPC18772
0.9012	High Similarity	NPC176300
0.9012	High Similarity	NPC9609
0.9012	High Similarity	NPC130894
0.9012	High Similarity	NPC22472
0.9012	High Similarity	NPC18607
0.9012	High Similarity	NPC115798
0.9012	High Similarity	NPC288669
0.9012	High Similarity	NPC19687
0.9012	High Similarity	NPC143828
0.9012	High Similarity	NPC7846
0.9012	High Similarity	NPC204854
0.9012	High Similarity	NPC4481
0.9012	High Similarity	NPC152166
0.9006	High Similarity	NPC266960
0.9006	High Similarity	NPC55619
0.9006	High Similarity	NPC200388
0.9006	High Similarity	NPC474520
0.9006	High Similarity	NPC43243
0.9006	High Similarity	NPC245546
0.9006	High Similarity	NPC100916
0.9006	High Similarity	NPC292107
0.9006	High Similarity	NPC268161
0.9006	High Similarity	NPC49824
0.9006	High Similarity	NPC228209
0.9	High Similarity	NPC89474
0.8994	High Similarity	NPC58668
0.8994	High Similarity	NPC106372
0.8988	High Similarity	NPC473834
0.8988	High Similarity	NPC310794
0.8988	High Similarity	NPC277510
0.8982	High Similarity	NPC28042
0.8976	High Similarity	NPC50394
0.8963	High Similarity	NPC294965
0.8957	High Similarity	NPC200746
0.8957	High Similarity	NPC320359
0.8951	High Similarity	NPC93376
0.8951	High Similarity	NPC217677
0.8951	High Similarity	NPC224137
0.8951	High Similarity	NPC469584
0.8951	High Similarity	NPC163524
0.8951	High Similarity	NPC176665
0.8951	High Similarity	NPC189179
0.8951	High Similarity	NPC287979
0.8951	High Similarity	NPC165977
0.8951	High Similarity	NPC75215
0.8951	High Similarity	NPC305663
0.8951	High Similarity	NPC227192
0.8944	High Similarity	NPC201451
0.8944	High Similarity	NPC189960
0.8944	High Similarity	NPC32557
0.8944	High Similarity	NPC80534
0.8944	High Similarity	NPC44079
0.8944	High Similarity	NPC56786
0.8944	High Similarity	NPC26227
0.8941	High Similarity	NPC475783
0.8941	High Similarity	NPC297807
0.8941	High Similarity	NPC246877
0.8941	High Similarity	NPC98546
0.8941	High Similarity	NPC221820
0.8938	High Similarity	NPC304954
0.8938	High Similarity	NPC207624
0.8935	High Similarity	NPC289244
0.8929	High Similarity	NPC307286
0.8922	High Similarity	NPC202470
0.8916	High Similarity	NPC477517
0.8909	High Similarity	NPC152659
0.8909	High Similarity	NPC41301
0.8909	High Similarity	NPC7483
0.8909	High Similarity	NPC248638
0.8909	High Similarity	NPC470459
0.8909	High Similarity	NPC236521
0.8909	High Similarity	NPC236132
0.8909	High Similarity	NPC220313
0.8902	High Similarity	NPC66288
0.8896	High Similarity	NPC329091
0.8896	High Similarity	NPC238381
0.8896	High Similarity	NPC152904
0.8896	High Similarity	NPC193842
0.8895	High Similarity	NPC240508
0.8895	High Similarity	NPC246153
0.8895	High Similarity	NPC8927
0.8889	High Similarity	NPC98661
0.8889	High Similarity	NPC247017
0.8889	High Similarity	NPC178854
0.8889	High Similarity	NPC265511
0.8889	High Similarity	NPC142339
0.8882	High Similarity	NPC255350
0.8882	High Similarity	NPC162351
0.8882	High Similarity	NPC22519
0.8882	High Similarity	NPC75279
0.8882	High Similarity	NPC24258
0.8882	High Similarity	NPC183878
0.8882	High Similarity	NPC145379
0.8882	High Similarity	NPC231018
0.8882	High Similarity	NPC270620
0.8882	High Similarity	NPC179126
0.8882	High Similarity	NPC86485
0.8882	High Similarity	NPC69394
0.8882	High Similarity	NPC276409
0.8882	High Similarity	NPC246204
0.8882	High Similarity	NPC274327
0.8882	High Similarity	NPC47781
0.8882	High Similarity	NPC250822
0.8882	High Similarity	NPC236223
0.8882	High Similarity	NPC58382
0.8882	High Similarity	NPC176775
0.8882	High Similarity	NPC160951
0.8882	High Similarity	NPC78326
0.8875	High Similarity	NPC23668
0.8875	High Similarity	NPC202157
0.8875	High Similarity	NPC115324
0.8875	High Similarity	NPC193976
0.8869	High Similarity	NPC131866
0.8862	High Similarity	NPC86477
0.8862	High Similarity	NPC76482
0.8857	High Similarity	NPC295436
0.8855	High Similarity	NPC224280
0.8855	High Similarity	NPC8070
0.8855	High Similarity	NPC275780
0.8855	High Similarity	NPC473286
0.8855	High Similarity	NPC470457
0.8855	High Similarity	NPC239752
0.8855	High Similarity	NPC472450
0.8851	High Similarity	NPC240808
0.8848	High Similarity	NPC25152
0.8848	High Similarity	NPC81679

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 NPC247136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	1006
0.2-0.3	1905
0.3-0.4	2757
0.4-0.5	1658
0.5-0.6	932
0.6-0.7	338
0.7-0.8	119
0.8-0.85	15
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9006	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD2801	Approved
0.8589	High Similarity	NPD1934	Approved
0.8521	High Similarity	NPD6166	Phase 2
0.8521	High Similarity	NPD6168	Clinical (unspecified phase)
0.8521	High Similarity	NPD6167	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3926	Phase 2
0.8452	Intermediate Similarity	NPD1247	Approved
0.8447	Intermediate Similarity	NPD1512	Approved
0.8424	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD3817	Phase 2
0.8323	Intermediate Similarity	NPD1511	Approved
0.8314	Intermediate Similarity	NPD3818	Discontinued
0.8294	Intermediate Similarity	NPD6232	Discontinued
0.8286	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD5494	Approved
0.8256	Intermediate Similarity	NPD7473	Discontinued
0.816	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD919	Approved
0.8107	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1465	Phase 2
0.8068	Intermediate Similarity	NPD6797	Phase 2
0.8059	Intermediate Similarity	NPD3749	Approved
0.8057	Intermediate Similarity	NPD5844	Phase 1
0.8023	Intermediate Similarity	NPD7251	Discontinued
0.8011	Intermediate Similarity	NPD7074	Phase 3
0.7988	Intermediate Similarity	NPD6799	Approved
0.7978	Intermediate Similarity	NPD7808	Phase 3
0.7966	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7054	Approved
0.7953	Intermediate Similarity	NPD7075	Discontinued
0.7919	Intermediate Similarity	NPD6959	Discontinued
0.7917	Intermediate Similarity	NPD6599	Discontinued
0.791	Intermediate Similarity	NPD7472	Approved
0.7882	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD2344	Approved
0.7836	Intermediate Similarity	NPD5402	Approved
0.7831	Intermediate Similarity	NPD2532	Approved
0.7831	Intermediate Similarity	NPD2534	Approved
0.7831	Intermediate Similarity	NPD2533	Approved
0.7829	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7819	Suspended
0.7744	Intermediate Similarity	NPD2800	Approved
0.773	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6801	Discontinued
0.7706	Intermediate Similarity	NPD4380	Phase 2
0.7688	Intermediate Similarity	NPD1240	Approved
0.7688	Intermediate Similarity	NPD943	Approved
0.7683	Intermediate Similarity	NPD1549	Phase 2
0.7654	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2309	Approved
0.7644	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7199	Phase 2
0.7607	Intermediate Similarity	NPD1510	Phase 2
0.76	Intermediate Similarity	NPD6234	Discontinued
0.7598	Intermediate Similarity	NPD3751	Discontinued
0.7593	Intermediate Similarity	NPD1607	Approved
0.7571	Intermediate Similarity	NPD3787	Discontinued
0.7561	Intermediate Similarity	NPD2796	Approved
0.7554	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1243	Approved
0.7529	Intermediate Similarity	NPD920	Approved
0.7529	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3750	Approved
0.7457	Intermediate Similarity	NPD7411	Suspended
0.7455	Intermediate Similarity	NPD2935	Discontinued
0.7447	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5403	Approved
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7419	Intermediate Similarity	NPD8434	Phase 2
0.7414	Intermediate Similarity	NPD37	Approved
0.7412	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1471	Phase 3
0.7389	Intermediate Similarity	NPD2403	Approved
0.7389	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD7768	Phase 2
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7390	Discontinued
0.7353	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD447	Suspended
0.731	Intermediate Similarity	NPD5401	Approved
0.7308	Intermediate Similarity	NPD7228	Approved
0.7294	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3027	Phase 3
0.7278	Intermediate Similarity	NPD5710	Approved
0.7278	Intermediate Similarity	NPD5711	Approved
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1613	Approved
0.7256	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6099	Approved
0.7246	Intermediate Similarity	NPD6100	Approved
0.7241	Intermediate Similarity	NPD3226	Approved
0.7235	Intermediate Similarity	NPD6190	Approved
0.7209	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3748	Approved
0.7186	Intermediate Similarity	NPD2799	Discontinued
0.7182	Intermediate Similarity	NPD7229	Phase 3
0.7176	Intermediate Similarity	NPD4628	Phase 3
0.7158	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7135	Intermediate Similarity	NPD2296	Approved
0.7134	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2163	Approved
0.7118	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7907	Approved
0.7101	Intermediate Similarity	NPD2346	Discontinued
0.7092	Intermediate Similarity	NPD6778	Approved
0.7092	Intermediate Similarity	NPD6776	Approved
0.7092	Intermediate Similarity	NPD6777	Approved
0.7092	Intermediate Similarity	NPD6782	Approved
0.7092	Intermediate Similarity	NPD6781	Approved
0.7092	Intermediate Similarity	NPD6780	Approved
0.7092	Intermediate Similarity	NPD6779	Approved
0.7076	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7435	Discontinued
0.7066	Intermediate Similarity	NPD6651	Approved
0.7055	Intermediate Similarity	NPD9494	Approved
0.7048	Intermediate Similarity	NPD4060	Phase 1
0.7019	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.7005	Intermediate Similarity	NPD4111	Phase 1
0.7005	Intermediate Similarity	NPD4665	Approved
0.7005	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7286	Phase 2
0.6989	Remote Similarity	NPD1653	Approved
0.6988	Remote Similarity	NPD6233	Phase 2
0.6984	Remote Similarity	NPD8312	Approved
0.6984	Remote Similarity	NPD8313	Approved
0.698	Remote Similarity	NPD8151	Discontinued
0.697	Remote Similarity	NPD2494	Approved
0.697	Remote Similarity	NPD2493	Approved
0.6968	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5089	Approved
0.6966	Remote Similarity	NPD5090	Approved
0.6963	Remote Similarity	NPD8150	Discontinued
0.6957	Remote Similarity	NPD5242	Approved
0.695	Remote Similarity	NPD7870	Phase 2
0.695	Remote Similarity	NPD7871	Phase 2
0.6939	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6927	Remote Similarity	NPD6279	Approved
0.6927	Remote Similarity	NPD6280	Approved
0.6919	Remote Similarity	NPD2654	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7783	Phase 2
0.6912	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4908	Phase 1
0.6905	Remote Similarity	NPD1933	Approved
0.69	Remote Similarity	NPD7696	Phase 3
0.69	Remote Similarity	NPD7697	Approved
0.69	Remote Similarity	NPD7698	Approved
0.6884	Remote Similarity	NPD3452	Approved
0.6884	Remote Similarity	NPD3450	Approved
0.6879	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7685	Pre-registration
0.6878	Remote Similarity	NPD7240	Approved
0.6875	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4625	Phase 3
0.6866	Remote Similarity	NPD4582	Approved
0.6866	Remote Similarity	NPD4583	Approved
0.6863	Remote Similarity	NPD7874	Approved
0.6863	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9269	Phase 2
0.6847	Remote Similarity	NPD7701	Phase 2
0.6845	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6535	Approved
0.6837	Remote Similarity	NPD6534	Approved
0.6831	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1203	Approved
0.6826	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2313	Discontinued
0.6816	Remote Similarity	NPD4002	Approved
0.6816	Remote Similarity	NPD4004	Approved
0.6811	Remote Similarity	NPD6808	Phase 2
0.6796	Remote Similarity	NPD5761	Phase 2
0.6796	Remote Similarity	NPD5760	Phase 2
0.6769	Remote Similarity	NPD2490	Approved
0.6769	Remote Similarity	NPD2488	Approved
0.6768	Remote Similarity	NPD2974	Approved
0.6768	Remote Similarity	NPD2973	Approved
0.6768	Remote Similarity	NPD2975	Approved
0.6766	Remote Similarity	NPD3057	Approved
0.6761	Remote Similarity	NPD4357	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