NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	251.998
LogP:	3.308
LogD:	3.455
LogS:	-3.83
# Rotatable Bonds:	0
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	4.376
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.587
MDCK Permeability:	3.521213511703536e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.412
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	59.68072509765625%
Volume Distribution (VD):	1.201
Pgp-substrate:	51.375633239746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.508
CYP1A2-substrate:	0.229
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.494
CYP3A4-inhibitor:	0.544
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	11.486
Half-life (T1/2):	0.242

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.772
Drug-inuced Liver Injury (DILI):	0.769
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.285
Skin Sensitization:	0.058
Carcinogencity:	0.25
Eye Corrosion:	0.029
Eye Irritation:	0.185
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC5714

Natural Product ID:	NPC5714
*Common Name:**	Mokko Lactone
IUPAC Name:	(3S,3aS,6aR,9aR,9bS)-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
Synonyms:	mokko lactone
Standard InCHIKey:	UJADCNYXDHHISU-PEDHHIEDSA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h10-14H,1-2,4-7H2,3H3/t10-,11-,12-,13-,14-/m0/s1
SMILES:	C=C1CC[C@@H]2[C@H]1[C@H]1OC(=O)[C@H]([C@@H]1CCC2=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453274
PubChem CID:	167495
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10391	Dolomiaea souliei	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
IC50	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	251000.0	nM	PMID[530435]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[530435]

☑ 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 NPC5714 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	212
0.1-0.2	2086
0.2-0.3	13375
0.3-0.4	12776
0.4-0.5	8457
0.5-0.6	4656
0.6-0.7	923
0.7-0.8	176
0.8-0.85	24
0.85-0.9	9
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.913	High Similarity	NPC320537
0.913	High Similarity	NPC143979
0.875	High Similarity	NPC208223
0.8649	High Similarity	NPC51507
0.8649	High Similarity	NPC290508
0.8649	High Similarity	NPC293418
0.8649	High Similarity	NPC156658
0.8649	High Similarity	NPC73052
0.8649	High Similarity	NPC258965
0.8649	High Similarity	NPC6823
0.8592	High Similarity	NPC469643
0.8592	High Similarity	NPC469641
0.8533	High Similarity	NPC126248
0.8514	High Similarity	NPC182550
0.8493	Intermediate Similarity	NPC195785
0.8493	Intermediate Similarity	NPC15975
0.8429	Intermediate Similarity	NPC472955
0.8421	Intermediate Similarity	NPC246076
0.84	Intermediate Similarity	NPC69271
0.84	Intermediate Similarity	NPC74673
0.84	Intermediate Similarity	NPC276356
0.8312	Intermediate Similarity	NPC245665
0.8312	Intermediate Similarity	NPC111409
0.8312	Intermediate Similarity	NPC54468
0.8312	Intermediate Similarity	NPC128246
0.8286	Intermediate Similarity	NPC296522
0.8286	Intermediate Similarity	NPC144511
0.8219	Intermediate Similarity	NPC471491
0.8101	Intermediate Similarity	NPC284534
0.8101	Intermediate Similarity	NPC204105
0.8101	Intermediate Similarity	NPC300082
0.8082	Intermediate Similarity	NPC472966
0.8052	Intermediate Similarity	NPC255580
0.8052	Intermediate Similarity	NPC39411
0.8028	Intermediate Similarity	NPC199557
0.8	Intermediate Similarity	NPC238593
0.8	Intermediate Similarity	NPC64153
0.8	Intermediate Similarity	NPC236692
0.8	Intermediate Similarity	NPC309757
0.8	Intermediate Similarity	NPC56593
0.8	Intermediate Similarity	NPC304558
0.7975	Intermediate Similarity	NPC194859
0.7975	Intermediate Similarity	NPC224386
0.7975	Intermediate Similarity	NPC156485
0.7971	Intermediate Similarity	NPC157518
0.7922	Intermediate Similarity	NPC302426
0.7901	Intermediate Similarity	NPC118601
0.7901	Intermediate Similarity	NPC270270
0.7901	Intermediate Similarity	NPC201658
0.7901	Intermediate Similarity	NPC24728
0.7875	Intermediate Similarity	NPC235792
0.7848	Intermediate Similarity	NPC39588
0.7848	Intermediate Similarity	NPC215294
0.7821	Intermediate Similarity	NPC10276
0.7821	Intermediate Similarity	NPC35089
0.7821	Intermediate Similarity	NPC47635
0.7805	Intermediate Similarity	NPC217983
0.7805	Intermediate Similarity	NPC207114
0.7805	Intermediate Similarity	NPC79549
0.7805	Intermediate Similarity	NPC178875
0.7805	Intermediate Similarity	NPC53158
0.7805	Intermediate Similarity	NPC471149
0.7778	Intermediate Similarity	NPC67493
0.7778	Intermediate Similarity	NPC187661
0.7763	Intermediate Similarity	NPC53581
0.7763	Intermediate Similarity	NPC476794
0.7763	Intermediate Similarity	NPC470240
0.7763	Intermediate Similarity	NPC103987
0.7763	Intermediate Similarity	NPC65603
0.775	Intermediate Similarity	NPC165287
0.7746	Intermediate Similarity	NPC469868
0.7733	Intermediate Similarity	NPC324762
0.7733	Intermediate Similarity	NPC226669
0.7733	Intermediate Similarity	NPC193351
0.7733	Intermediate Similarity	NPC138408
0.7711	Intermediate Similarity	NPC283409
0.7711	Intermediate Similarity	NPC215556
0.7711	Intermediate Similarity	NPC155935
0.7711	Intermediate Similarity	NPC168679
0.7711	Intermediate Similarity	NPC472872
0.7711	Intermediate Similarity	NPC12872
0.7703	Intermediate Similarity	NPC472956
0.7692	Intermediate Similarity	NPC170038
0.7662	Intermediate Similarity	NPC35574
0.7654	Intermediate Similarity	NPC161957
0.7654	Intermediate Similarity	NPC78089
0.7654	Intermediate Similarity	NPC33570
0.7654	Intermediate Similarity	NPC21471
0.7632	Intermediate Similarity	NPC472967
0.7632	Intermediate Similarity	NPC266159
0.7632	Intermediate Similarity	NPC92489
0.7632	Intermediate Similarity	NPC472959
0.7632	Intermediate Similarity	NPC235906
0.7619	Intermediate Similarity	NPC216284
0.7619	Intermediate Similarity	NPC35809
0.7619	Intermediate Similarity	NPC297474
0.7619	Intermediate Similarity	NPC19087
0.7619	Intermediate Similarity	NPC54065
0.759	Intermediate Similarity	NPC91248
0.759	Intermediate Similarity	NPC224652
0.7568	Intermediate Similarity	NPC129665
0.7564	Intermediate Similarity	NPC470244
0.7564	Intermediate Similarity	NPC118987
0.7564	Intermediate Similarity	NPC470239
0.7561	Intermediate Similarity	NPC107787
0.7531	Intermediate Similarity	NPC115786
0.7531	Intermediate Similarity	NPC100391
0.7529	Intermediate Similarity	NPC191339
0.7529	Intermediate Similarity	NPC171360
0.7529	Intermediate Similarity	NPC184063
0.7529	Intermediate Similarity	NPC63193
0.7529	Intermediate Similarity	NPC286341
0.7529	Intermediate Similarity	NPC29821
0.7529	Intermediate Similarity	NPC293001
0.7529	Intermediate Similarity	NPC57304
0.7529	Intermediate Similarity	NPC475925
0.7529	Intermediate Similarity	NPC155215
0.7529	Intermediate Similarity	NPC35959
0.7529	Intermediate Similarity	NPC133888
0.75	Intermediate Similarity	NPC4986
0.75	Intermediate Similarity	NPC38392
0.75	Intermediate Similarity	NPC89555
0.75	Intermediate Similarity	NPC155587
0.747	Intermediate Similarity	NPC190753
0.747	Intermediate Similarity	NPC237540
0.7442	Intermediate Similarity	NPC200237
0.7442	Intermediate Similarity	NPC308656
0.7442	Intermediate Similarity	NPC473273
0.7442	Intermediate Similarity	NPC153590
0.7442	Intermediate Similarity	NPC473263
0.7442	Intermediate Similarity	NPC473234
0.7442	Intermediate Similarity	NPC475788
0.7442	Intermediate Similarity	NPC258216
0.7442	Intermediate Similarity	NPC60386
0.7436	Intermediate Similarity	NPC299235
0.7432	Intermediate Similarity	NPC18543
0.7412	Intermediate Similarity	NPC37607
0.7412	Intermediate Similarity	NPC301969
0.7381	Intermediate Similarity	NPC190718
0.7375	Intermediate Similarity	NPC223330
0.7375	Intermediate Similarity	NPC281949
0.7375	Intermediate Similarity	NPC475951
0.7375	Intermediate Similarity	NPC301477
0.7375	Intermediate Similarity	NPC25684
0.7375	Intermediate Similarity	NPC470241
0.7375	Intermediate Similarity	NPC38642
0.7375	Intermediate Similarity	NPC209318
0.7356	Intermediate Similarity	NPC473331
0.7349	Intermediate Similarity	NPC470242
0.7342	Intermediate Similarity	NPC89128
0.7342	Intermediate Similarity	NPC63649
0.7342	Intermediate Similarity	NPC264227
0.7342	Intermediate Similarity	NPC617
0.7342	Intermediate Similarity	NPC472965
0.7333	Intermediate Similarity	NPC40327
0.7333	Intermediate Similarity	NPC163003
0.7333	Intermediate Similarity	NPC470243
0.7326	Intermediate Similarity	NPC131209
0.7326	Intermediate Similarity	NPC133698
0.7308	Intermediate Similarity	NPC187568
0.7308	Intermediate Similarity	NPC41780
0.7294	Intermediate Similarity	NPC288699
0.7284	Intermediate Similarity	NPC226988
0.7273	Intermediate Similarity	NPC475861
0.7273	Intermediate Similarity	NPC474419
0.7273	Intermediate Similarity	NPC163228
0.7273	Intermediate Similarity	NPC167893
0.7273	Intermediate Similarity	NPC476053
0.7273	Intermediate Similarity	NPC472873
0.7262	Intermediate Similarity	NPC475773
0.7262	Intermediate Similarity	NPC167877
0.725	Intermediate Similarity	NPC223904
0.7241	Intermediate Similarity	NPC135776
0.7241	Intermediate Similarity	NPC472874
0.7237	Intermediate Similarity	NPC58956
0.7237	Intermediate Similarity	NPC92909
0.7237	Intermediate Similarity	NPC107783
0.7237	Intermediate Similarity	NPC295633
0.7237	Intermediate Similarity	NPC269206
0.7229	Intermediate Similarity	NPC470223
0.7215	Intermediate Similarity	NPC472960
0.72	Intermediate Similarity	NPC475310
0.7195	Intermediate Similarity	NPC470948
0.7195	Intermediate Similarity	NPC475622
0.7195	Intermediate Similarity	NPC194637
0.7195	Intermediate Similarity	NPC108045
0.7191	Intermediate Similarity	NPC474297
0.7191	Intermediate Similarity	NPC24956
0.7191	Intermediate Similarity	NPC18019
0.7191	Intermediate Similarity	NPC91771
0.7191	Intermediate Similarity	NPC142529
0.7188	Intermediate Similarity	NPC142103
0.7188	Intermediate Similarity	NPC305182
0.7179	Intermediate Similarity	NPC226242
0.7179	Intermediate Similarity	NPC474527
0.7179	Intermediate Similarity	NPC471726
0.7179	Intermediate Similarity	NPC41017
0.7179	Intermediate Similarity	NPC476601
0.7179	Intermediate Similarity	NPC123360
0.7176	Intermediate Similarity	NPC28227

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 NPC5714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	2907
0.2-0.3	4094
0.3-0.4	1251
0.4-0.5	488
0.5-0.6	133
0.6-0.7	37
0.7-0.8	1
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
0.75	Intermediate Similarity	NPD1695	Approved
0.6988	Remote Similarity	NPD5362	Discontinued
0.6951	Remote Similarity	NPD5369	Approved
0.6889	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6903	Approved
0.6744	Remote Similarity	NPD6684	Approved
0.6744	Remote Similarity	NPD7146	Approved
0.6744	Remote Similarity	NPD7521	Approved
0.6744	Remote Similarity	NPD7334	Approved
0.6744	Remote Similarity	NPD6409	Approved
0.6744	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4269	Approved
0.6628	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD1694	Approved
0.6591	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7154	Phase 3
0.6556	Remote Similarity	NPD8034	Phase 2
0.6556	Remote Similarity	NPD8035	Phase 2
0.6552	Remote Similarity	NPD5786	Approved
0.6528	Remote Similarity	NPD3198	Approved
0.6444	Remote Similarity	NPD5207	Approved
0.6437	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5363	Approved
0.6429	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4252	Approved
0.6404	Remote Similarity	NPD5737	Approved
0.6404	Remote Similarity	NPD6672	Approved
0.6395	Remote Similarity	NPD5332	Approved
0.6395	Remote Similarity	NPD5331	Approved
0.6386	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4790	Discontinued
0.6344	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4251	Approved
0.6292	Remote Similarity	NPD4250	Approved
0.6282	Remote Similarity	NPD229	Approved
0.6279	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3667	Approved
0.6264	Remote Similarity	NPD5785	Approved
0.6263	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD5777	Approved
0.6237	Remote Similarity	NPD6001	Approved
0.6235	Remote Similarity	NPD4821	Approved
0.6235	Remote Similarity	NPD4819	Approved
0.6235	Remote Similarity	NPD4822	Approved
0.6235	Remote Similarity	NPD4820	Approved
0.6216	Remote Similarity	NPD1145	Discontinued
0.619	Remote Similarity	NPD4271	Approved
0.619	Remote Similarity	NPD4268	Approved
0.618	Remote Similarity	NPD6098	Approved
0.6154	Remote Similarity	NPD6101	Approved
0.6154	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD3668	Phase 3
0.6136	Remote Similarity	NPD4786	Approved
0.6064	Remote Similarity	NPD5282	Discontinued
0.6056	Remote Similarity	NPD9298	Approved
0.6044	Remote Similarity	NPD5208	Approved
0.6024	Remote Similarity	NPD8039	Approved
0.6022	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD4238	Approved
0.5979	Remote Similarity	NPD5696	Approved
0.5978	Remote Similarity	NPD6904	Approved
0.5978	Remote Similarity	NPD6673	Approved
0.5978	Remote Similarity	NPD6080	Approved
0.5957	Remote Similarity	NPD5779	Approved
0.5957	Remote Similarity	NPD5778	Approved
0.5955	Remote Similarity	NPD3666	Approved
0.5955	Remote Similarity	NPD3133	Approved
0.5955	Remote Similarity	NPD3665	Phase 1
0.5938	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5692	Phase 3
0.5909	Remote Similarity	NPD2699	Approved
0.5897	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7900	Approved
0.5895	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6083	Phase 2
0.5876	Remote Similarity	NPD6084	Phase 2
0.5851	Remote Similarity	NPD5694	Approved
0.5851	Remote Similarity	NPD6050	Approved
0.5851	Remote Similarity	NPD5693	Phase 1
0.5843	Remote Similarity	NPD4788	Approved
0.5833	Remote Similarity	NPD3702	Approved
0.5833	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6422	Discontinued
0.5824	Remote Similarity	NPD5279	Phase 3
0.5821	Remote Similarity	NPD634	Phase 3
0.5755	Remote Similarity	NPD6053	Discontinued
0.5745	Remote Similarity	NPD46	Approved
0.5745	Remote Similarity	NPD6698	Approved
0.5743	Remote Similarity	NPD6052	Approved
0.573	Remote Similarity	NPD5209	Approved
0.5729	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD6371	Approved
0.5714	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7902	Approved
0.5684	Remote Similarity	NPD5284	Approved
0.5684	Remote Similarity	NPD5281	Approved
0.5684	Remote Similarity	NPD7637	Suspended
0.5684	Remote Similarity	NPD7983	Approved
0.5673	Remote Similarity	NPD7320	Approved
0.5657	Remote Similarity	NPD7638	Approved
0.5657	Remote Similarity	NPD4225	Approved
0.5652	Remote Similarity	NPD622	Approved
0.5638	Remote Similarity	NPD6051	Approved
0.5638	Remote Similarity	NPD5328	Approved
0.5638	Remote Similarity	NPD5370	Suspended
0.5634	Remote Similarity	NPD29	Approved
0.5634	Remote Similarity	NPD28	Approved
0.5631	Remote Similarity	NPD6402	Approved
0.5631	Remote Similarity	NPD6675	Approved
0.5631	Remote Similarity	NPD5739	Approved
0.5631	Remote Similarity	NPD7128	Approved
0.5625	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6373	Approved
0.5619	Remote Similarity	NPD6372	Approved
0.5618	Remote Similarity	NPD857	Phase 3
0.5616	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD387	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7640	Approved
0.56	Remote Similarity	NPD7639	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