NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.08
Volume:	250.242
LogP:	3.189
LogD:	3.01
LogS:	-4.645
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	2.622
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.505
MDCK Permeability:	2.196518653363455e-05
Pgp-inhibitor:	0.725
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.31
30% Bioavailability (F30%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	98.79533386230469%
Volume Distribution (VD):	0.684
Pgp-substrate:	1.035078763961792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.515
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.904
CYP2C9-substrate:	0.332
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.796
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	1.475
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.836
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.784
Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.36
Carcinogencity:	0.863
Eye Corrosion:	0.004
Eye Irritation:	0.504
Respiratory Toxicity:	0.785

Download Data

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

Natural Product: NPC291799

Natural Product ID:	NPC291799
*Common Name:**	Dehydro-Alpha-Lapachone
IUPAC Name:	2,2-dimethylbenzo[g]chromene-5,10-dione
Synonyms:	Dehydro-Alpha-Lapachone
Standard InCHIKey:	OWFHAMHRUCUSRM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-8H,1-2H3
SMILES:	CC1(C)C=CC2=C(C(=O)c3ccccc3C2=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL272253
PubChem CID:	72734
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19674905]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32044231]
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	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
Others	4

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	=	214.0	nM	PMID[507817]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	>	10000.0	nM	PMID[507818]
NPT2936	Individual Protein	NADPH--cytochrome P450 reductase	Homo sapiens	Activity	=	852.0	micromol/min	PMID[507820]
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	Activity	=	774.0	micromol/min	PMID[507820]
NPT2	Others	Unspecified		Selectivity ratio	=	0.91	n.a.	PMID[507820]
NPT35	Others	n.a.		Activity	=	-1.22	V	PMID[507820]

☑ 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 NPC291799 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	305
0.1-0.2	1509
0.2-0.3	3809
0.3-0.4	10373
0.4-0.5	11532
0.5-0.6	11125
0.6-0.7	3714
0.7-0.8	295
0.8-0.85	25
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC192577
0.9327	High Similarity	NPC470391
0.9065	High Similarity	NPC137315
0.8981	High Similarity	NPC212415
0.8932	High Similarity	NPC112552
0.8909	High Similarity	NPC470764
0.8667	High Similarity	NPC244427
0.8667	High Similarity	NPC222390
0.8649	High Similarity	NPC196075
0.8585	High Similarity	NPC274443
0.8559	High Similarity	NPC13784
0.8547	High Similarity	NPC65627
0.8482	Intermediate Similarity	NPC241851
0.8482	Intermediate Similarity	NPC326664
0.844	Intermediate Similarity	NPC203732
0.8426	Intermediate Similarity	NPC209632
0.8426	Intermediate Similarity	NPC172483
0.8407	Intermediate Similarity	NPC474408
0.8407	Intermediate Similarity	NPC228936
0.8362	Intermediate Similarity	NPC204784
0.8333	Intermediate Similarity	NPC114594
0.8333	Intermediate Similarity	NPC135730
0.8319	Intermediate Similarity	NPC477411
0.8291	Intermediate Similarity	NPC232958
0.8286	Intermediate Similarity	NPC156021
0.8198	Intermediate Similarity	NPC269023
0.8198	Intermediate Similarity	NPC99846
0.8182	Intermediate Similarity	NPC236405
0.8174	Intermediate Similarity	NPC226093
0.8158	Intermediate Similarity	NPC67377
0.8142	Intermediate Similarity	NPC292834
0.8136	Intermediate Similarity	NPC476225
0.8136	Intermediate Similarity	NPC105709
0.8099	Intermediate Similarity	NPC295664
0.8087	Intermediate Similarity	NPC474095
0.8067	Intermediate Similarity	NPC144547
0.8053	Intermediate Similarity	NPC474157
0.8053	Intermediate Similarity	NPC210089
0.8019	Intermediate Similarity	NPC12695
0.8018	Intermediate Similarity	NPC30594
0.8018	Intermediate Similarity	NPC37622
0.8017	Intermediate Similarity	NPC62138
0.7983	Intermediate Similarity	NPC289432
0.7983	Intermediate Similarity	NPC988
0.7981	Intermediate Similarity	NPC476484
0.7967	Intermediate Similarity	NPC81135
0.7941	Intermediate Similarity	NPC43945
0.7928	Intermediate Similarity	NPC134120
0.7913	Intermediate Similarity	NPC143768
0.7913	Intermediate Similarity	NPC272524
0.7909	Intermediate Similarity	NPC60679
0.7864	Intermediate Similarity	NPC157778
0.7846	Intermediate Similarity	NPC284184
0.7846	Intermediate Similarity	NPC301341
0.7845	Intermediate Similarity	NPC308744
0.7833	Intermediate Similarity	NPC77000
0.7833	Intermediate Similarity	NPC238861
0.7812	Intermediate Similarity	NPC171968
0.7778	Intermediate Similarity	NPC471832
0.7778	Intermediate Similarity	NPC474685
0.7778	Intermediate Similarity	NPC103048
0.7778	Intermediate Similarity	NPC210092
0.7739	Intermediate Similarity	NPC243355
0.7739	Intermediate Similarity	NPC474057
0.7724	Intermediate Similarity	NPC51079
0.7714	Intermediate Similarity	NPC173413
0.7706	Intermediate Similarity	NPC145052
0.7699	Intermediate Similarity	NPC100767
0.7699	Intermediate Similarity	NPC119271
0.7679	Intermediate Similarity	NPC31786
0.7672	Intermediate Similarity	NPC186128
0.7672	Intermediate Similarity	NPC79496
0.7667	Intermediate Similarity	NPC318173
0.7658	Intermediate Similarity	NPC45613
0.7647	Intermediate Similarity	NPC469843
0.7642	Intermediate Similarity	NPC284475
0.7636	Intermediate Similarity	NPC325497
0.7632	Intermediate Similarity	NPC56493
0.7607	Intermediate Similarity	NPC161611
0.7593	Intermediate Similarity	NPC5472
0.7589	Intermediate Similarity	NPC247976
0.7586	Intermediate Similarity	NPC167504
0.7583	Intermediate Similarity	NPC323440
0.7583	Intermediate Similarity	NPC222968
0.7583	Intermediate Similarity	NPC80605
0.7581	Intermediate Similarity	NPC328107
0.7581	Intermediate Similarity	NPC182646
0.7581	Intermediate Similarity	NPC318067
0.7578	Intermediate Similarity	NPC27659
0.757	Intermediate Similarity	NPC188844
0.757	Intermediate Similarity	NPC1682
0.757	Intermediate Similarity	NPC155232
0.7565	Intermediate Similarity	NPC83628
0.7565	Intermediate Similarity	NPC17417
0.7565	Intermediate Similarity	NPC265407
0.7565	Intermediate Similarity	NPC10251
0.7563	Intermediate Similarity	NPC149691
0.7563	Intermediate Similarity	NPC260886
0.7559	Intermediate Similarity	NPC237225
0.7549	Intermediate Similarity	NPC215008
0.7547	Intermediate Similarity	NPC110420
0.7547	Intermediate Similarity	NPC67585
0.7547	Intermediate Similarity	NPC303967
0.7547	Intermediate Similarity	NPC19256
0.7542	Intermediate Similarity	NPC196673
0.754	Intermediate Similarity	NPC177925
0.754	Intermediate Similarity	NPC51292
0.7522	Intermediate Similarity	NPC329282
0.7519	Intermediate Similarity	NPC173980
0.7519	Intermediate Similarity	NPC205360
0.75	Intermediate Similarity	NPC214067
0.75	Intermediate Similarity	NPC320891
0.75	Intermediate Similarity	NPC238219
0.75	Intermediate Similarity	NPC232996
0.75	Intermediate Similarity	NPC174099
0.75	Intermediate Similarity	NPC93084
0.75	Intermediate Similarity	NPC251854
0.75	Intermediate Similarity	NPC164947
0.75	Intermediate Similarity	NPC289883
0.75	Intermediate Similarity	NPC196246
0.7479	Intermediate Similarity	NPC93181
0.7477	Intermediate Similarity	NPC133461
0.7455	Intermediate Similarity	NPC249912
0.7455	Intermediate Similarity	NPC276775
0.7455	Intermediate Similarity	NPC92754
0.744	Intermediate Similarity	NPC135062
0.7438	Intermediate Similarity	NPC268930
0.7438	Intermediate Similarity	NPC228318
0.7436	Intermediate Similarity	NPC305912
0.7436	Intermediate Similarity	NPC260818
0.7436	Intermediate Similarity	NPC1082
0.7434	Intermediate Similarity	NPC474365
0.7434	Intermediate Similarity	NPC301943
0.7434	Intermediate Similarity	NPC89886
0.7431	Intermediate Similarity	NPC130398
0.7431	Intermediate Similarity	NPC260233
0.7424	Intermediate Similarity	NPC217914
0.7414	Intermediate Similarity	NPC40178
0.7414	Intermediate Similarity	NPC85493
0.7411	Intermediate Similarity	NPC42211
0.7411	Intermediate Similarity	NPC70624
0.7407	Intermediate Similarity	NPC153885
0.7407	Intermediate Similarity	NPC59677
0.7402	Intermediate Similarity	NPC51037
0.7398	Intermediate Similarity	NPC473243
0.7387	Intermediate Similarity	NPC49994
0.7387	Intermediate Similarity	NPC75724
0.7387	Intermediate Similarity	NPC134882
0.7387	Intermediate Similarity	NPC78701
0.7387	Intermediate Similarity	NPC35448
0.7387	Intermediate Similarity	NPC229242
0.7387	Intermediate Similarity	NPC225060
0.7381	Intermediate Similarity	NPC310540
0.7373	Intermediate Similarity	NPC270699
0.7373	Intermediate Similarity	NPC321852
0.7373	Intermediate Similarity	NPC82899
0.7373	Intermediate Similarity	NPC23332
0.7358	Intermediate Similarity	NPC267262
0.7355	Intermediate Similarity	NPC158157
0.735	Intermediate Similarity	NPC273837
0.7344	Intermediate Similarity	NPC45537
0.7344	Intermediate Similarity	NPC428300
0.7344	Intermediate Similarity	NPC478162
0.7344	Intermediate Similarity	NPC478165
0.7339	Intermediate Similarity	NPC472981
0.7339	Intermediate Similarity	NPC34243
0.7333	Intermediate Similarity	NPC306740
0.7333	Intermediate Similarity	NPC160339
0.7333	Intermediate Similarity	NPC307
0.7328	Intermediate Similarity	NPC470007
0.7328	Intermediate Similarity	NPC47536
0.7323	Intermediate Similarity	NPC476599
0.7321	Intermediate Similarity	NPC203925
0.7321	Intermediate Similarity	NPC146351
0.7321	Intermediate Similarity	NPC118343
0.7315	Intermediate Similarity	NPC110704
0.7313	Intermediate Similarity	NPC186647
0.7311	Intermediate Similarity	NPC128368
0.7308	Intermediate Similarity	NPC198305
0.7302	Intermediate Similarity	NPC325740
0.7297	Intermediate Similarity	NPC265220
0.7297	Intermediate Similarity	NPC239185
0.7295	Intermediate Similarity	NPC61651
0.7293	Intermediate Similarity	NPC309056
0.7293	Intermediate Similarity	NPC22644
0.729	Intermediate Similarity	NPC418308
0.7288	Intermediate Similarity	NPC183648
0.7287	Intermediate Similarity	NPC165257
0.7273	Intermediate Similarity	NPC100353
0.7273	Intermediate Similarity	NPC471616
0.7266	Intermediate Similarity	NPC231774
0.7265	Intermediate Similarity	NPC474364
0.7264	Intermediate Similarity	NPC96625
0.7259	Intermediate Similarity	NPC265181
0.7258	Intermediate Similarity	NPC206778
0.7258	Intermediate Similarity	NPC285829
0.7257	Intermediate Similarity	NPC109514
0.7257	Intermediate Similarity	NPC476993
0.725	Intermediate Similarity	NPC471721
0.725	Intermediate Similarity	NPC153053

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 NPC291799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	962
0.2-0.3	1188
0.3-0.4	3013
0.4-0.5	2384
0.5-0.6	1076
0.6-0.7	205
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8981	High Similarity	NPD1609	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD650	Approved
0.7833	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD164	Approved
0.7642	Intermediate Similarity	NPD7609	Phase 3
0.7627	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD7631	Approved
0.7565	Intermediate Similarity	NPD2182	Approved
0.7436	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5909	Discontinued
0.7339	Intermediate Similarity	NPD4879	Approved
0.7339	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1238	Approved
0.7297	Intermediate Similarity	NPD3495	Discontinued
0.7259	Intermediate Similarity	NPD1471	Phase 3
0.725	Intermediate Similarity	NPD1241	Discontinued
0.7217	Intermediate Similarity	NPD1237	Approved
0.7203	Intermediate Similarity	NPD2067	Discontinued
0.7143	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1930	Approved
0.713	Intermediate Similarity	NPD1929	Approved
0.7109	Intermediate Similarity	NPD1876	Approved
0.7087	Intermediate Similarity	NPD3972	Approved
0.7049	Intermediate Similarity	NPD5951	Approved
0.7027	Intermediate Similarity	NPD1202	Approved
0.7018	Intermediate Similarity	NPD2066	Phase 3
0.7009	Intermediate Similarity	NPD9257	Approved
0.7009	Intermediate Similarity	NPD9259	Approved
0.6975	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4878	Approved
0.695	Remote Similarity	NPD3950	Discontinued
0.6937	Remote Similarity	NPD1508	Approved
0.6935	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1932	Approved
0.6879	Remote Similarity	NPD7236	Approved
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2798	Approved
0.6857	Remote Similarity	NPD942	Approved
0.685	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1470	Approved
0.6789	Remote Similarity	NPD1087	Approved
0.6789	Remote Similarity	NPD1282	Approved
0.6772	Remote Similarity	NPD1651	Approved
0.6763	Remote Similarity	NPD2346	Discontinued
0.6757	Remote Similarity	NPD9256	Approved
0.6757	Remote Similarity	NPD9258	Approved
0.6754	Remote Similarity	NPD1989	Approved
0.6754	Remote Similarity	NPD1843	Approved
0.6744	Remote Similarity	NPD6287	Discontinued
0.6744	Remote Similarity	NPD1201	Approved
0.6742	Remote Similarity	NPD2788	Approved
0.6739	Remote Similarity	NPD3748	Approved
0.6726	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7008	Discontinued
0.6694	Remote Similarity	NPD2329	Discontinued
0.6693	Remote Similarity	NPD7009	Phase 2
0.6693	Remote Similarity	NPD9545	Approved
0.6691	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD9490	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3267	Approved
0.6644	Remote Similarity	NPD7239	Suspended
0.6643	Remote Similarity	NPD2353	Approved
0.6643	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7961	Discontinued
0.6615	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD1281	Approved
0.6614	Remote Similarity	NPD7610	Discontinued
0.6613	Remote Similarity	NPD7094	Approved
0.6613	Remote Similarity	NPD6858	Approved
0.6607	Remote Similarity	NPD1089	Approved
0.6607	Remote Similarity	NPD1090	Approved
0.6607	Remote Similarity	NPD1086	Approved
0.6579	Remote Similarity	NPD1563	Approved
0.6574	Remote Similarity	NPD9491	Approved
0.6565	Remote Similarity	NPD6637	Approved
0.6549	Remote Similarity	NPD1239	Approved
0.6535	Remote Similarity	NPD9493	Approved
0.6522	Remote Similarity	NPD9260	Approved
0.6518	Remote Similarity	NPD800	Approved
0.6512	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3750	Approved
0.65	Remote Similarity	NPD4308	Phase 3
0.6496	Remote Similarity	NPD9495	Approved
0.6496	Remote Similarity	NPD7713	Phase 3
0.6491	Remote Similarity	NPD1088	Approved
0.6486	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3226	Approved
0.6466	Remote Similarity	NPD5667	Approved
0.6466	Remote Similarity	NPD1283	Approved
0.6462	Remote Similarity	NPD2932	Approved
0.6462	Remote Similarity	NPD17	Approved
0.6458	Remote Similarity	NPD3887	Approved
0.6458	Remote Similarity	NPD2354	Approved
0.6457	Remote Similarity	NPD4198	Discontinued
0.6457	Remote Similarity	NPD3317	Approved
0.6454	Remote Similarity	NPD2796	Approved
0.6449	Remote Similarity	NPD3140	Approved
0.6449	Remote Similarity	NPD3142	Approved
0.6449	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD9717	Approved
0.6429	Remote Similarity	NPD6010	Discontinued
0.6423	Remote Similarity	NPD3268	Approved
0.6418	Remote Similarity	NPD2797	Approved
0.6417	Remote Similarity	NPD6647	Phase 2
0.6417	Remote Similarity	NPD9261	Approved
0.6415	Remote Similarity	NPD227	Approved
0.6415	Remote Similarity	NPD225	Approved
0.641	Remote Similarity	NPD1565	Approved
0.641	Remote Similarity	NPD1566	Phase 3
0.641	Remote Similarity	NPD1564	Approved
0.6408	Remote Similarity	NPD2344	Approved
0.6408	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6832	Phase 2
0.6397	Remote Similarity	NPD7055	Discontinued
0.6389	Remote Similarity	NPD7003	Approved
0.6385	Remote Similarity	NPD3025	Approved
0.6385	Remote Similarity	NPD3024	Approved
0.6383	Remote Similarity	NPD2799	Discontinued
0.6383	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2629	Approved
0.6377	Remote Similarity	NPD8032	Phase 2
0.6371	Remote Similarity	NPD1317	Discontinued
0.637	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1607	Approved
0.635	Remote Similarity	NPD6039	Approved
0.6341	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7057	Phase 3
0.634	Remote Similarity	NPD7058	Phase 2
0.6336	Remote Similarity	NPD3019	Approved
0.6331	Remote Similarity	NPD1240	Approved
0.6327	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3672	Approved
0.6316	Remote Similarity	NPD3673	Approved
0.6316	Remote Similarity	NPD1608	Approved
0.6311	Remote Similarity	NPD9697	Approved
0.6301	Remote Similarity	NPD3300	Phase 2
0.6296	Remote Similarity	NPD1203	Approved
0.6288	Remote Similarity	NPD3023	Approved
0.6288	Remote Similarity	NPD3026	Approved
0.6284	Remote Similarity	NPD6273	Approved
0.6284	Remote Similarity	NPD5049	Phase 3
0.6269	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD1510	Phase 2
0.626	Remote Similarity	NPD4102	Approved
0.626	Remote Similarity	NPD4105	Approved
0.626	Remote Similarity	NPD5691	Approved
0.6259	Remote Similarity	NPD6799	Approved
0.625	Remote Similarity	NPD4980	Approved
0.625	Remote Similarity	NPD970	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1019	Discontinued
0.6239	Remote Similarity	NPD226	Approved
0.6233	Remote Similarity	NPD2309	Approved
0.6233	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD2347	Approved
0.6225	Remote Similarity	NPD6599	Discontinued
0.6222	Remote Similarity	NPD2198	Approved
0.6222	Remote Similarity	NPD2199	Approved
0.6216	Remote Similarity	NPD5401	Approved
0.6214	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD2979	Phase 3
0.6212	Remote Similarity	NPD5305	Approved
0.6212	Remote Similarity	NPD5306	Approved
0.6212	Remote Similarity	NPD2345	Approved
0.621	Remote Similarity	NPD9267	Approved
0.621	Remote Similarity	NPD9263	Approved
0.621	Remote Similarity	NPD9264	Approved
0.6207	Remote Similarity	NPD1243	Approved
0.6181	Remote Similarity	NPD7611	Approved
0.6181	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1933	Approved
0.6165	Remote Similarity	NPD4106	Approved
0.6165	Remote Similarity	NPD4135	Approved
0.6165	Remote Similarity	NPD4136	Approved
0.6164	Remote Similarity	NPD8166	Discontinued
0.6164	Remote Similarity	NPD4628	Phase 3
0.616	Remote Similarity	NPD74	Approved
0.616	Remote Similarity	NPD9266	Approved
0.6154	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5159	Phase 2
0.6148	Remote Similarity	NPD5157	Phase 1
0.6144	Remote Similarity	NPD6801	Discontinued
0.6142	Remote Similarity	NPD9508	Approved
0.6138	Remote Similarity	NPD1549	Phase 2
0.6138	Remote Similarity	NPD2897	Discontinued
0.6136	Remote Similarity	NPD1245	Approved
0.6133	Remote Similarity	NPD5403	Approved
0.6129	Remote Similarity	NPD3134	Approved
0.6126	Remote Similarity	NPD3971	Phase 1
0.6124	Remote Similarity	NPD1246	Approved
0.6119	Remote Similarity	NPD4807	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