NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	261.669
LogP:	2.936
LogD:	2.314
LogS:	-3.384
# Rotatable Bonds:	1
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	2.752
Fsp3:	0.2
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:	-4.997
MDCK Permeability:	1.7430664229323156e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.058
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.316

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	95.25074005126953%
Volume Distribution (VD):	0.605
Pgp-substrate:	9.734383583068848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.845
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.209
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.678
CYP2D6-inhibitor:	0.623
CYP2D6-substrate:	0.372
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	6.326
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.547
Rat Oral Acute Toxicity:	0.292
Maximum Recommended Daily Dose:	0.496
Skin Sensitization:	0.858
Carcinogencity:	0.692
Eye Corrosion:	0.003
Eye Irritation:	0.278
Respiratory Toxicity:	0.247

Download Data

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

Natural Product: NPC105709

Natural Product ID:	NPC105709
*Common Name:**	Stenocarpoquinone B
IUPAC Name:	(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione
Synonyms:	stenocarpoquinone B
Standard InCHIKey:	JEXUSWQCJDSVMY-NSHDSACASA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-15(2,18)11-7-10-12(16)8-5-3-4-6-9(8)13(17)14(10)19-11/h3-6,11,18H,7H2,1-2H3/t11-/m0/s1
SMILES:	CC(C)([C@@H]1CC2=C(C(=O)c3ccccc3C2=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226338
PubChem CID:	44423355
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
NPO3629	Avicennia marina	Species	Acanthaceae	Eukaryota	twigs	n.a.	n.a.	PMID[17500572]
NPO3629	Avicennia marina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19377635]
NPO3629	Avicennia marina	Species	Acanthaceae	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
GI50	2
MIC	7
Others	1

Activity Type	# Activity
Cell Line	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	GI50	=	1.2	ug.mL-1	PMID[487671]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	0.2	ug.mL-1	PMID[487671]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	4.3	ug.mL-1	PMID[487671]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	12.5	ug.mL-1	PMID[487671]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	12.5	ug.mL-1	PMID[487671]
NPT5246	Organism	Mycobacterium aurum	Mycobacterium aurum	MIC	=	12.5	ug.mL-1	PMID[487671]
NPT3473	Organism	Mycobacterium vaccae	Mycobacterium vaccae	MIC	=	6.25	ug.mL-1	PMID[487671]
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	25.0	ug.mL-1	PMID[487671]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[487671]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	25.0	ug.mL-1	PMID[487671]

☑ 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 NPC105709 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	219
0.1-0.2	1016
0.2-0.3	2541
0.3-0.4	7569
0.4-0.5	13311
0.5-0.6	11802
0.6-0.7	5811
0.7-0.8	384
0.8-0.85	36
0.85-0.9	4
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC81135
0.9167	High Similarity	NPC236405
0.9035	High Similarity	NPC241851
0.8957	High Similarity	NPC470764
0.876	High Similarity	NPC65627
0.8596	High Similarity	NPC192577
0.8548	High Similarity	NPC328997
0.8548	High Similarity	NPC294050
0.8482	Intermediate Similarity	NPC274443
0.8448	Intermediate Similarity	NPC137315
0.8413	Intermediate Similarity	NPC316553
0.8393	Intermediate Similarity	NPC222390
0.8393	Intermediate Similarity	NPC244427
0.8376	Intermediate Similarity	NPC292834
0.8333	Intermediate Similarity	NPC172483
0.8304	Intermediate Similarity	NPC112552
0.825	Intermediate Similarity	NPC62138
0.8235	Intermediate Similarity	NPC477411
0.8197	Intermediate Similarity	NPC318173
0.819	Intermediate Similarity	NPC470391
0.8189	Intermediate Similarity	NPC146239
0.8167	Intermediate Similarity	NPC217111
0.8136	Intermediate Similarity	NPC291799
0.813	Intermediate Similarity	NPC204784
0.812	Intermediate Similarity	NPC38158
0.8115	Intermediate Similarity	NPC323440
0.8115	Intermediate Similarity	NPC471553
0.8115	Intermediate Similarity	NPC222968
0.8115	Intermediate Similarity	NPC80605
0.8099	Intermediate Similarity	NPC226093
0.8095	Intermediate Similarity	NPC328107
0.8095	Intermediate Similarity	NPC318067
0.8036	Intermediate Similarity	NPC156021
0.8034	Intermediate Similarity	NPC203732
0.7984	Intermediate Similarity	NPC478162
0.7984	Intermediate Similarity	NPC478165
0.797	Intermediate Similarity	NPC23894
0.7955	Intermediate Similarity	NPC144257
0.7953	Intermediate Similarity	NPC325740
0.7949	Intermediate Similarity	NPC100767
0.7934	Intermediate Similarity	NPC326664
0.7891	Intermediate Similarity	NPC246166
0.7868	Intermediate Similarity	NPC173980
0.7863	Intermediate Similarity	NPC134120
0.7863	Intermediate Similarity	NPC262819
0.7851	Intermediate Similarity	NPC143768
0.7787	Intermediate Similarity	NPC67377
0.7769	Intermediate Similarity	NPC212415
0.7761	Intermediate Similarity	NPC171968
0.7752	Intermediate Similarity	NPC295664
0.7742	Intermediate Similarity	NPC469843
0.7717	Intermediate Similarity	NPC144547
0.7704	Intermediate Similarity	NPC474659
0.7692	Intermediate Similarity	NPC247976
0.7687	Intermediate Similarity	NPC477407
0.7686	Intermediate Similarity	NPC474057
0.768	Intermediate Similarity	NPC61651
0.7667	Intermediate Similarity	NPC475282
0.7661	Intermediate Similarity	NPC135730
0.7652	Intermediate Similarity	NPC145052
0.7652	Intermediate Similarity	NPC237225
0.7642	Intermediate Similarity	NPC196075
0.7638	Intermediate Similarity	NPC289432
0.7638	Intermediate Similarity	NPC988
0.7627	Intermediate Similarity	NPC329282
0.7623	Intermediate Similarity	NPC186128
0.7622	Intermediate Similarity	NPC476821
0.7607	Intermediate Similarity	NPC320891
0.7597	Intermediate Similarity	NPC139171
0.7591	Intermediate Similarity	NPC232996
0.7589	Intermediate Similarity	NPC476484
0.7578	Intermediate Similarity	NPC476234
0.7578	Intermediate Similarity	NPC472981
0.7576	Intermediate Similarity	NPC115797
0.7576	Intermediate Similarity	NPC51448
0.7561	Intermediate Similarity	NPC13784
0.7559	Intermediate Similarity	NPC476645
0.7559	Intermediate Similarity	NPC202015
0.7556	Intermediate Similarity	NPC477406
0.7554	Intermediate Similarity	NPC114620
0.7554	Intermediate Similarity	NPC103337
0.7538	Intermediate Similarity	NPC51079
0.7538	Intermediate Similarity	NPC135062
0.7537	Intermediate Similarity	NPC471334
0.7537	Intermediate Similarity	NPC198305
0.7537	Intermediate Similarity	NPC27659
0.7536	Intermediate Similarity	NPC264022
0.7518	Intermediate Similarity	NPC309056
0.75	Intermediate Similarity	NPC83409
0.75	Intermediate Similarity	NPC196673
0.75	Intermediate Similarity	NPC185763
0.75	Intermediate Similarity	NPC238861
0.75	Intermediate Similarity	NPC51037
0.75	Intermediate Similarity	NPC77000
0.75	Intermediate Similarity	NPC310662
0.7463	Intermediate Similarity	NPC471832
0.7462	Intermediate Similarity	NPC164947
0.746	Intermediate Similarity	NPC108532
0.7448	Intermediate Similarity	NPC306799
0.7448	Intermediate Similarity	NPC101043
0.7445	Intermediate Similarity	NPC212207
0.744	Intermediate Similarity	NPC474408
0.744	Intermediate Similarity	NPC228936
0.7438	Intermediate Similarity	NPC211439
0.7438	Intermediate Similarity	NPC112903
0.7431	Intermediate Similarity	NPC273798
0.7431	Intermediate Similarity	NPC136878
0.7429	Intermediate Similarity	NPC477408
0.7426	Intermediate Similarity	NPC309430
0.7424	Intermediate Similarity	NPC476599
0.7419	Intermediate Similarity	NPC470253
0.7415	Intermediate Similarity	NPC471613
0.7413	Intermediate Similarity	NPC29932
0.741	Intermediate Similarity	NPC119542
0.7398	Intermediate Similarity	NPC265513
0.7388	Intermediate Similarity	NPC165257
0.7381	Intermediate Similarity	NPC260886
0.7376	Intermediate Similarity	NPC472546
0.7372	Intermediate Similarity	NPC254603
0.7368	Intermediate Similarity	NPC15837
0.7368	Intermediate Similarity	NPC231774
0.7364	Intermediate Similarity	NPC232958
0.7361	Intermediate Similarity	NPC474309
0.7361	Intermediate Similarity	NPC478160
0.7353	Intermediate Similarity	NPC205360
0.7348	Intermediate Similarity	NPC310540
0.7339	Intermediate Similarity	NPC218855
0.7339	Intermediate Similarity	NPC474314
0.7339	Intermediate Similarity	NPC477250
0.7333	Intermediate Similarity	NPC249067
0.7333	Intermediate Similarity	NPC49272
0.7329	Intermediate Similarity	NPC280025
0.7329	Intermediate Similarity	NPC132810
0.7329	Intermediate Similarity	NPC94781
0.7328	Intermediate Similarity	NPC223351
0.7328	Intermediate Similarity	NPC12695
0.7321	Intermediate Similarity	NPC157778
0.7319	Intermediate Similarity	NPC472247
0.7313	Intermediate Similarity	NPC472707
0.7313	Intermediate Similarity	NPC324209
0.7302	Intermediate Similarity	NPC474095
0.7302	Intermediate Similarity	NPC274839
0.7288	Intermediate Similarity	NPC474308
0.7287	Intermediate Similarity	NPC472708
0.7286	Intermediate Similarity	NPC301341
0.7286	Intermediate Similarity	NPC284184
0.728	Intermediate Similarity	NPC272524
0.7279	Intermediate Similarity	NPC120171
0.7279	Intermediate Similarity	NPC280753
0.7279	Intermediate Similarity	NPC44378
0.7273	Intermediate Similarity	NPC471466
0.7273	Intermediate Similarity	NPC85511
0.7273	Intermediate Similarity	NPC228739
0.7267	Intermediate Similarity	NPC478159
0.7267	Intermediate Similarity	NPC478161
0.7266	Intermediate Similarity	NPC268930
0.7266	Intermediate Similarity	NPC472551
0.7266	Intermediate Similarity	NPC472545
0.7265	Intermediate Similarity	NPC103048
0.726	Intermediate Similarity	NPC469425
0.7258	Intermediate Similarity	NPC210089
0.7258	Intermediate Similarity	NPC260818
0.7254	Intermediate Similarity	NPC182869
0.725	Intermediate Similarity	NPC329556
0.7244	Intermediate Similarity	NPC149691
0.7241	Intermediate Similarity	NPC475923
0.7241	Intermediate Similarity	NPC474630
0.7236	Intermediate Similarity	NPC281604
0.7236	Intermediate Similarity	NPC265407
0.7236	Intermediate Similarity	NPC83628
0.7236	Intermediate Similarity	NPC474364
0.7234	Intermediate Similarity	NPC476643
0.7232	Intermediate Similarity	NPC43945
0.7227	Intermediate Similarity	NPC158623
0.7226	Intermediate Similarity	NPC477412
0.7222	Intermediate Similarity	NPC307651
0.7222	Intermediate Similarity	NPC478164
0.7222	Intermediate Similarity	NPC474363
0.7222	Intermediate Similarity	NPC234637
0.7222	Intermediate Similarity	NPC11824
0.7222	Intermediate Similarity	NPC308744
0.7222	Intermediate Similarity	NPC127857
0.7222	Intermediate Similarity	NPC130591
0.7218	Intermediate Similarity	NPC474766
0.7218	Intermediate Similarity	NPC478108
0.7214	Intermediate Similarity	NPC315275
0.7214	Intermediate Similarity	NPC39549
0.7213	Intermediate Similarity	NPC475905
0.7213	Intermediate Similarity	NPC37914
0.7213	Intermediate Similarity	NPC193640
0.7213	Intermediate Similarity	NPC25385
0.7211	Intermediate Similarity	NPC51602
0.7211	Intermediate Similarity	NPC471103
0.7203	Intermediate Similarity	NPC317280
0.7203	Intermediate Similarity	NPC329387
0.72	Intermediate Similarity	NPC321852
0.7197	Intermediate Similarity	NPC91478
0.7193	Intermediate Similarity	NPC110420
0.7193	Intermediate Similarity	NPC303967
0.7193	Intermediate Similarity	NPC173413

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 NPC105709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	794
0.2-0.3	1420
0.3-0.4	2910
0.4-0.5	2433
0.5-0.6	1155
0.6-0.7	218
0.7-0.8	15
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
0.8136	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2067	Discontinued
0.7333	Intermediate Similarity	NPD1237	Approved
0.725	Intermediate Similarity	NPD1930	Approved
0.725	Intermediate Similarity	NPD1929	Approved
0.725	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD650	Approved
0.7226	Intermediate Similarity	NPD7961	Discontinued
0.7176	Intermediate Similarity	NPD4879	Approved
0.7167	Intermediate Similarity	NPD1932	Approved
0.713	Intermediate Similarity	NPD7609	Phase 3
0.712	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7236	Approved
0.708	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7631	Approved
0.705	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2629	Approved
0.7	Intermediate Similarity	NPD2066	Phase 3
0.6993	Remote Similarity	NPD1471	Phase 3
0.696	Remote Similarity	NPD2182	Approved
0.696	Remote Similarity	NPD2329	Discontinued
0.6917	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD164	Approved
0.6867	Remote Similarity	NPD7239	Suspended
0.6864	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7009	Phase 2
0.6807	Remote Similarity	NPD1693	Approved
0.6807	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1470	Approved
0.6777	Remote Similarity	NPD9495	Approved
0.6772	Remote Similarity	NPD1317	Discontinued
0.6769	Remote Similarity	NPD5951	Approved
0.6744	Remote Similarity	NPD6858	Approved
0.6744	Remote Similarity	NPD7094	Approved
0.6742	Remote Similarity	NPD7610	Discontinued
0.6739	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4628	Phase 3
0.6718	Remote Similarity	NPD4198	Discontinued
0.6694	Remote Similarity	NPD6647	Phase 2
0.6694	Remote Similarity	NPD3495	Discontinued
0.6691	Remote Similarity	NPD4878	Approved
0.6639	Remote Similarity	NPD1508	Approved
0.6612	Remote Similarity	NPD1989	Approved
0.661	Remote Similarity	NPD1089	Approved
0.661	Remote Similarity	NPD1086	Approved
0.661	Remote Similarity	NPD1090	Approved
0.6596	Remote Similarity	NPD7008	Discontinued
0.6594	Remote Similarity	NPD1876	Approved
0.6593	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5306	Approved
0.6593	Remote Similarity	NPD5305	Approved
0.6577	Remote Similarity	NPD2354	Approved
0.6561	Remote Similarity	NPD7058	Phase 2
0.6561	Remote Similarity	NPD7057	Phase 3
0.6555	Remote Similarity	NPD1239	Approved
0.6549	Remote Similarity	NPD3764	Approved
0.6544	Remote Similarity	NPD4106	Approved
0.6544	Remote Similarity	NPD4135	Approved
0.6544	Remote Similarity	NPD4136	Approved
0.6538	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2346	Discontinued
0.6531	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6355	Discontinued
0.6525	Remote Similarity	NPD800	Approved
0.6507	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1088	Approved
0.6496	Remote Similarity	NPD4807	Approved
0.6496	Remote Similarity	NPD4806	Approved
0.6496	Remote Similarity	NPD1201	Approved
0.6475	Remote Similarity	NPD1843	Approved
0.6467	Remote Similarity	NPD3887	Approved
0.6466	Remote Similarity	NPD3317	Approved
0.6454	Remote Similarity	NPD5204	Approved
0.6454	Remote Similarity	NPD9494	Approved
0.6452	Remote Similarity	NPD6599	Discontinued
0.6452	Remote Similarity	NPD1238	Approved
0.645	Remote Similarity	NPD8434	Phase 2
0.6449	Remote Similarity	NPD3972	Approved
0.6444	Remote Similarity	NPD9545	Approved
0.6439	Remote Similarity	NPD1241	Discontinued
0.6435	Remote Similarity	NPD9491	Approved
0.6424	Remote Similarity	NPD3300	Phase 2
0.6423	Remote Similarity	NPD1566	Phase 3
0.6423	Remote Similarity	NPD1564	Approved
0.6423	Remote Similarity	NPD1565	Approved
0.6419	Remote Similarity	NPD2344	Approved
0.6415	Remote Similarity	NPD7075	Discontinued
0.6412	Remote Similarity	NPD969	Suspended
0.6404	Remote Similarity	NPD942	Approved
0.6402	Remote Similarity	NPD7799	Discontinued
0.6397	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD4102	Approved
0.6397	Remote Similarity	NPD4105	Approved
0.6395	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6799	Approved
0.6378	Remote Similarity	NPD5909	Discontinued
0.6356	Remote Similarity	NPD1087	Approved
0.6352	Remote Similarity	NPD3882	Suspended
0.635	Remote Similarity	NPD2932	Approved
0.635	Remote Similarity	NPD2345	Approved
0.6347	Remote Similarity	NPD8368	Discontinued
0.6338	Remote Similarity	NPD3662	Phase 3
0.6338	Remote Similarity	NPD3664	Approved
0.6338	Remote Similarity	NPD7084	Phase 3
0.6338	Remote Similarity	NPD3661	Approved
0.6338	Remote Similarity	NPD3663	Approved
0.6333	Remote Similarity	NPD9258	Approved
0.6333	Remote Similarity	NPD9256	Approved
0.6331	Remote Similarity	NPD8407	Phase 2
0.632	Remote Similarity	NPD7798	Approved
0.6319	Remote Similarity	NPD2313	Discontinued
0.6319	Remote Similarity	NPD6798	Discontinued
0.6316	Remote Similarity	NPD2652	Approved
0.6316	Remote Similarity	NPD2650	Approved
0.6316	Remote Similarity	NPD6010	Discontinued
0.6311	Remote Similarity	NPD1202	Approved
0.6309	Remote Similarity	NPD2353	Approved
0.6309	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6273	Approved
0.6299	Remote Similarity	NPD5049	Phase 3
0.6296	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4620	Approved
0.6294	Remote Similarity	NPD5201	Approved
0.6294	Remote Similarity	NPD4617	Approved
0.6294	Remote Similarity	NPD5203	Approved
0.6291	Remote Similarity	NPD8166	Discontinued
0.6286	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2799	Discontinued
0.6284	Remote Similarity	NPD7305	Phase 1
0.6282	Remote Similarity	NPD3226	Approved
0.6282	Remote Similarity	NPD7458	Discontinued
0.6279	Remote Similarity	NPD6685	Approved
0.6277	Remote Similarity	NPD1245	Approved
0.6275	Remote Similarity	NPD3950	Discontinued
0.6275	Remote Similarity	NPD8165	Discontinued
0.6269	Remote Similarity	NPD1246	Approved
0.6268	Remote Similarity	NPD2788	Approved
0.6266	Remote Similarity	NPD6801	Discontinued
0.6261	Remote Similarity	NPD226	Approved
0.6259	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD6287	Discontinued
0.6257	Remote Similarity	NPD8150	Discontinued
0.625	Remote Similarity	NPD6764	Approved
0.625	Remote Similarity	NPD6190	Approved
0.625	Remote Similarity	NPD2309	Approved
0.625	Remote Similarity	NPD6765	Approved
0.6242	Remote Similarity	NPD4380	Phase 2
0.6241	Remote Similarity	NPD1283	Approved
0.6233	Remote Similarity	NPD943	Approved
0.6232	Remote Similarity	NPD5126	Approved
0.6232	Remote Similarity	NPD3019	Approved
0.6232	Remote Similarity	NPD5125	Phase 3
0.6225	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4619	Approved
0.6207	Remote Similarity	NPD4621	Approved
0.6205	Remote Similarity	NPD3751	Discontinued
0.6202	Remote Similarity	NPD5048	Discontinued
0.62	Remote Similarity	NPD5763	Approved
0.62	Remote Similarity	NPD5762	Approved
0.6198	Remote Similarity	NPD3672	Approved
0.6198	Remote Similarity	NPD3673	Approved
0.6197	Remote Similarity	NPD2625	Approved
0.6197	Remote Similarity	NPD2159	Approved
0.6197	Remote Similarity	NPD2628	Approved
0.6197	Remote Similarity	NPD2627	Approved
0.6197	Remote Similarity	NPD2626	Approved
0.6197	Remote Similarity	NPD2160	Approved
0.619	Remote Similarity	NPD230	Phase 1
0.6181	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD1563	Approved
0.6178	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD2651	Approved
0.6178	Remote Similarity	NPD2649	Approved
0.6174	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD1510	Phase 2
0.617	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5157	Phase 1
0.617	Remote Similarity	NPD5159	Phase 2
0.6164	Remote Similarity	NPD6233	Phase 2
0.6164	Remote Similarity	NPD4062	Phase 3
0.6164	Remote Similarity	NPD6663	Approved
0.6163	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD1549	Phase 2
0.6159	Remote Similarity	NPD1651	Approved
0.6159	Remote Similarity	NPD2424	Discontinued
0.6154	Remote Similarity	NPD2798	Approved
0.6149	Remote Similarity	NPD1607	Approved
0.6136	Remote Similarity	NPD4234	Approved
0.6136	Remote Similarity	NPD4233	Approved
0.6134	Remote Similarity	NPD9257	Approved
0.6134	Remote Similarity	NPD9259	Approved
0.6131	Remote Similarity	NPD6065	Approved
0.6129	Remote Similarity	NPD2532	Approved
0.6129	Remote Similarity	NPD2533	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