NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	264.072
LogP:	2.736
LogD:	2.743
LogS:	-3.418
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	3.685
Fsp3:	0.4
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:	-4.744
MDCK Permeability:	1.4463536899711471e-05
Pgp-inhibitor:	0.245
Pgp-substrate:	0.907
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.801
30% Bioavailability (F30%):	0.096

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.869
Plasma Protein Binding (PPB):	66.3735580444336%
Volume Distribution (VD):	1.467
Pgp-substrate:	28.832239151000977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.807
CYP1A2-substrate:	0.481
CYP2C19-inhibitor:	0.257
CYP2C19-substrate:	0.795
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.753
CYP2D6-inhibitor:	0.157
CYP2D6-substrate:	0.284
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	7.027
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.677
AMES Toxicity:	0.343
Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.723
Skin Sensitization:	0.893
Carcinogencity:	0.106
Eye Corrosion:	0.022
Eye Irritation:	0.491
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC273683

Natural Product ID:	NPC273683
*Common Name:**	Lacinilene C
IUPAC Name:	(1R)-1,7-dihydroxy-1,6-dimethyl-4-propan-2-ylnaphthalen-2-one
Synonyms:	Lacinilene C
Standard InCHIKey:	JLCJSBOHWRDWQW-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-8(2)10-6-14(17)15(4,18)12-7-13(16)9(3)5-11(10)12/h5-8,16,18H,1-4H3/t15-/m1/s1
SMILES:	CC(C1=CC(=O)[C@](c2c1cc(C)c(c2)O)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254803
PubChem CID:	170551
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29953	Bombax malabaricum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17764148]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23734721]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29953	Bombax malabaricum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29953	Bombax malabaricum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15986	Alangium chinense	Species	Cornaceae	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	3

Activity Type	# Activity
Cell Line	1
Organism	1
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2511	Cell Line	HGC-27	Homo sapiens	IC50	>	10000.0	nM	PMID[448450]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	39800.0	nM	PMID[448451]
NPT3494	Organism	Coxsackievirus	Coxsackievirus	IC50	=	15400.0	nM	PMID[448451]

☑ 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 NPC273683 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	301
0.1-0.2	1526
0.2-0.3	3319
0.3-0.4	9469
0.4-0.5	9941
0.5-0.6	7097
0.6-0.7	8453
0.7-0.8	2305
0.8-0.85	224
0.85-0.9	50
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC123506
0.9431	High Similarity	NPC253488
0.9412	High Similarity	NPC282577
0.9256	High Similarity	NPC199273
0.9194	High Similarity	NPC171460
0.9127	High Similarity	NPC312560
0.9032	High Similarity	NPC72667
0.9008	High Similarity	NPC154696
0.8968	High Similarity	NPC108129
0.896	High Similarity	NPC96024
0.8952	High Similarity	NPC254492
0.888	High Similarity	NPC78364
0.888	High Similarity	NPC176130
0.888	High Similarity	NPC69424
0.888	High Similarity	NPC84672
0.8819	High Similarity	NPC470725
0.88	High Similarity	NPC15837
0.877	High Similarity	NPC259703
0.877	High Similarity	NPC32322
0.876	High Similarity	NPC78307
0.875	High Similarity	NPC471851
0.874	High Similarity	NPC276238
0.874	High Similarity	NPC303910
0.8692	High Similarity	NPC202225
0.8661	High Similarity	NPC3009
0.8618	High Similarity	NPC190971
0.8615	High Similarity	NPC59459
0.8615	High Similarity	NPC263817
0.8594	High Similarity	NPC278928
0.8571	High Similarity	NPC137750
0.8561	High Similarity	NPC86524
0.856	High Similarity	NPC471187
0.856	High Similarity	NPC275145
0.8537	High Similarity	NPC478121
0.8527	High Similarity	NPC198305
0.8516	High Similarity	NPC24869
0.8496	Intermediate Similarity	NPC475957
0.8496	Intermediate Similarity	NPC471452
0.8492	Intermediate Similarity	NPC474766
0.8492	Intermediate Similarity	NPC310540
0.848	Intermediate Similarity	NPC176208
0.848	Intermediate Similarity	NPC164947
0.848	Intermediate Similarity	NPC307174
0.8473	Intermediate Similarity	NPC138472
0.8473	Intermediate Similarity	NPC477139
0.8468	Intermediate Similarity	NPC241001
0.8462	Intermediate Similarity	NPC41847
0.8448	Intermediate Similarity	NPC21594
0.8433	Intermediate Similarity	NPC230811
0.8421	Intermediate Similarity	NPC475549
0.8421	Intermediate Similarity	NPC471670
0.8421	Intermediate Similarity	NPC474311
0.8417	Intermediate Similarity	NPC242136
0.8413	Intermediate Similarity	NPC135062
0.84	Intermediate Similarity	NPC162935
0.84	Intermediate Similarity	NPC249340
0.8385	Intermediate Similarity	NPC27659
0.8376	Intermediate Similarity	NPC228737
0.8374	Intermediate Similarity	NPC328694
0.8359	Intermediate Similarity	NPC160499
0.8359	Intermediate Similarity	NPC231774
0.8359	Intermediate Similarity	NPC71610
0.8358	Intermediate Similarity	NPC156888
0.8358	Intermediate Similarity	NPC470721
0.8358	Intermediate Similarity	NPC6100
0.8358	Intermediate Similarity	NPC470722
0.8346	Intermediate Similarity	NPC68756
0.8346	Intermediate Similarity	NPC290803
0.8346	Intermediate Similarity	NPC181334
0.8346	Intermediate Similarity	NPC152525
0.8346	Intermediate Similarity	NPC22644
0.8333	Intermediate Similarity	NPC111845
0.8333	Intermediate Similarity	NPC231717
0.8333	Intermediate Similarity	NPC171968
0.8333	Intermediate Similarity	NPC11250
0.8333	Intermediate Similarity	NPC121168
0.8306	Intermediate Similarity	NPC473767
0.8271	Intermediate Similarity	NPC50924
0.8271	Intermediate Similarity	NPC218854
0.8271	Intermediate Similarity	NPC52368
0.8258	Intermediate Similarity	NPC165612
0.8258	Intermediate Similarity	NPC309430
0.8254	Intermediate Similarity	NPC120545
0.8248	Intermediate Similarity	NPC110810
0.824	Intermediate Similarity	NPC285829
0.824	Intermediate Similarity	NPC206778
0.8231	Intermediate Similarity	NPC237225
0.8222	Intermediate Similarity	NPC53001
0.8222	Intermediate Similarity	NPC36868
0.822	Intermediate Similarity	NPC151477
0.8217	Intermediate Similarity	NPC306765
0.8217	Intermediate Similarity	NPC474737
0.8217	Intermediate Similarity	NPC1991
0.8211	Intermediate Similarity	NPC477453
0.8209	Intermediate Similarity	NPC153088
0.8203	Intermediate Similarity	NPC74507
0.8203	Intermediate Similarity	NPC164014
0.8203	Intermediate Similarity	NPC234890
0.8203	Intermediate Similarity	NPC173978
0.8195	Intermediate Similarity	NPC52407
0.8195	Intermediate Similarity	NPC267205
0.8189	Intermediate Similarity	NPC91478
0.8188	Intermediate Similarity	NPC308572
0.8188	Intermediate Similarity	NPC201297
0.8182	Intermediate Similarity	NPC93015
0.8182	Intermediate Similarity	NPC286222
0.8182	Intermediate Similarity	NPC85342
0.8182	Intermediate Similarity	NPC476847
0.8175	Intermediate Similarity	NPC164852
0.8168	Intermediate Similarity	NPC117899
0.8162	Intermediate Similarity	NPC87723
0.8162	Intermediate Similarity	NPC475104
0.8154	Intermediate Similarity	NPC19432
0.8154	Intermediate Similarity	NPC324209
0.8151	Intermediate Similarity	NPC279887
0.8151	Intermediate Similarity	NPC68260
0.8148	Intermediate Similarity	NPC191976
0.8145	Intermediate Similarity	NPC160199
0.814	Intermediate Similarity	NPC131799
0.814	Intermediate Similarity	NPC477454
0.8134	Intermediate Similarity	NPC12070
0.813	Intermediate Similarity	NPC322197
0.8125	Intermediate Similarity	NPC198014
0.811	Intermediate Similarity	NPC25168
0.811	Intermediate Similarity	NPC253627
0.8106	Intermediate Similarity	NPC62219
0.8106	Intermediate Similarity	NPC117609
0.8099	Intermediate Similarity	NPC151537
0.8095	Intermediate Similarity	NPC318552
0.8095	Intermediate Similarity	NPC190501
0.8092	Intermediate Similarity	NPC193203
0.8092	Intermediate Similarity	NPC48248
0.8088	Intermediate Similarity	NPC264022
0.8088	Intermediate Similarity	NPC277559
0.8083	Intermediate Similarity	NPC26013
0.8083	Intermediate Similarity	NPC282855
0.8083	Intermediate Similarity	NPC95172
0.8083	Intermediate Similarity	NPC58865
0.8077	Intermediate Similarity	NPC473691
0.8077	Intermediate Similarity	NPC295202
0.8077	Intermediate Similarity	NPC51037
0.8077	Intermediate Similarity	NPC227741
0.8077	Intermediate Similarity	NPC3224
0.8077	Intermediate Similarity	NPC136342
0.8077	Intermediate Similarity	NPC49647
0.8074	Intermediate Similarity	NPC283088
0.8074	Intermediate Similarity	NPC249272
0.8074	Intermediate Similarity	NPC80035
0.8065	Intermediate Similarity	NPC325646
0.8065	Intermediate Similarity	NPC28951
0.8065	Intermediate Similarity	NPC471668
0.8062	Intermediate Similarity	NPC142956
0.806	Intermediate Similarity	NPC49742
0.806	Intermediate Similarity	NPC254603
0.806	Intermediate Similarity	NPC314048
0.806	Intermediate Similarity	NPC48036
0.806	Intermediate Similarity	NPC53896
0.806	Intermediate Similarity	NPC114183
0.806	Intermediate Similarity	NPC37299
0.806	Intermediate Similarity	NPC4170
0.806	Intermediate Similarity	NPC180261
0.8058	Intermediate Similarity	NPC248068
0.8051	Intermediate Similarity	NPC117115
0.8049	Intermediate Similarity	NPC93181
0.8045	Intermediate Similarity	NPC474517
0.8045	Intermediate Similarity	NPC244699
0.8045	Intermediate Similarity	NPC18798
0.8045	Intermediate Similarity	NPC239134
0.8045	Intermediate Similarity	NPC291001
0.8045	Intermediate Similarity	NPC72669
0.8043	Intermediate Similarity	NPC169452
0.8043	Intermediate Similarity	NPC181560
0.8043	Intermediate Similarity	NPC471853
0.8033	Intermediate Similarity	NPC250323
0.8031	Intermediate Similarity	NPC472046
0.8031	Intermediate Similarity	NPC165197
0.803	Intermediate Similarity	NPC34414
0.803	Intermediate Similarity	NPC99731
0.803	Intermediate Similarity	NPC92624
0.803	Intermediate Similarity	NPC146647
0.8029	Intermediate Similarity	NPC13715
0.8029	Intermediate Similarity	NPC173980
0.8017	Intermediate Similarity	NPC474057
0.8017	Intermediate Similarity	NPC132720
0.8017	Intermediate Similarity	NPC208229
0.8016	Intermediate Similarity	NPC473974
0.8016	Intermediate Similarity	NPC42657
0.8016	Intermediate Similarity	NPC31296
0.8016	Intermediate Similarity	NPC258366
0.8016	Intermediate Similarity	NPC79933
0.8015	Intermediate Similarity	NPC118919
0.8015	Intermediate Similarity	NPC471530
0.8015	Intermediate Similarity	NPC30491
0.8015	Intermediate Similarity	NPC315275
0.8015	Intermediate Similarity	NPC254847
0.8015	Intermediate Similarity	NPC472308
0.8015	Intermediate Similarity	NPC262936
0.8014	Intermediate Similarity	NPC478160
0.8	Intermediate Similarity	NPC475733
0.8	Intermediate Similarity	NPC174087

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 NPC273683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	954
0.2-0.3	1462
0.3-0.4	2687
0.4-0.5	2074
0.5-0.6	1139
0.6-0.7	455
0.7-0.8	59
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.824	Intermediate Similarity	NPD2932	Approved
0.8095	Intermediate Similarity	NPD3019	Approved
0.8016	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD1201	Approved
0.792	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD7390	Discontinued
0.7746	Intermediate Similarity	NPD3300	Phase 2
0.7742	Intermediate Similarity	NPD7635	Approved
0.7727	Intermediate Similarity	NPD1470	Approved
0.7652	Intermediate Similarity	NPD1283	Approved
0.7607	Intermediate Similarity	NPD288	Approved
0.7597	Intermediate Similarity	NPD1651	Approved
0.7538	Intermediate Similarity	NPD4626	Approved
0.7521	Intermediate Similarity	NPD844	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4750	Phase 3
0.7481	Intermediate Similarity	NPD3026	Approved
0.7481	Intermediate Similarity	NPD3023	Approved
0.7462	Intermediate Similarity	NPD3025	Approved
0.7462	Intermediate Similarity	NPD3024	Approved
0.7447	Intermediate Similarity	NPD5404	Approved
0.7447	Intermediate Similarity	NPD5405	Approved
0.7447	Intermediate Similarity	NPD5408	Approved
0.7447	Intermediate Similarity	NPD5406	Approved
0.7424	Intermediate Similarity	NPD1281	Approved
0.7397	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1809	Phase 2
0.735	Intermediate Similarity	NPD845	Approved
0.7339	Intermediate Similarity	NPD2342	Discontinued
0.7333	Intermediate Similarity	NPD3020	Approved
0.7333	Intermediate Similarity	NPD1164	Approved
0.7324	Intermediate Similarity	NPD6099	Approved
0.7324	Intermediate Similarity	NPD6100	Approved
0.7313	Intermediate Similarity	NPD1755	Approved
0.7273	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6663	Approved
0.7241	Intermediate Similarity	NPD7003	Approved
0.7226	Intermediate Similarity	NPD5736	Approved
0.7222	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD943	Approved
0.7203	Intermediate Similarity	NPD2935	Discontinued
0.72	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5691	Approved
0.7162	Intermediate Similarity	NPD2532	Approved
0.7162	Intermediate Similarity	NPD2534	Approved
0.7162	Intermediate Similarity	NPD2533	Approved
0.7162	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD4059	Approved
0.7143	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD8166	Discontinued
0.7123	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3091	Approved
0.7113	Intermediate Similarity	NPD1607	Approved
0.7111	Intermediate Similarity	NPD3972	Approved
0.7092	Intermediate Similarity	NPD4060	Phase 1
0.7092	Intermediate Similarity	NPD2979	Phase 3
0.7087	Intermediate Similarity	NPD3022	Approved
0.7087	Intermediate Similarity	NPD3021	Approved
0.7083	Intermediate Similarity	NPD2860	Approved
0.7083	Intermediate Similarity	NPD2859	Approved
0.7077	Intermediate Similarity	NPD5951	Approved
0.7059	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD2934	Approved
0.7	Intermediate Similarity	NPD1398	Phase 1
0.7	Intermediate Similarity	NPD2933	Approved
0.7	Intermediate Similarity	NPD7473	Discontinued
0.6992	Remote Similarity	NPD9545	Approved
0.6985	Remote Similarity	NPD1608	Approved
0.6977	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3226	Approved
0.6974	Remote Similarity	NPD7458	Discontinued
0.6972	Remote Similarity	NPD1240	Approved
0.697	Remote Similarity	NPD7340	Approved
0.6962	Remote Similarity	NPD6959	Discontinued
0.695	Remote Similarity	NPD3764	Approved
0.6947	Remote Similarity	NPD497	Approved
0.6935	Remote Similarity	NPD846	Approved
0.6935	Remote Similarity	NPD940	Approved
0.6918	Remote Similarity	NPD6232	Discontinued
0.6918	Remote Similarity	NPD2344	Approved
0.6912	Remote Similarity	NPD3092	Approved
0.6911	Remote Similarity	NPD2066	Phase 3
0.6906	Remote Similarity	NPD2798	Approved
0.6889	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2286	Discontinued
0.6889	Remote Similarity	NPD1751	Approved
0.6884	Remote Similarity	NPD1876	Approved
0.6884	Remote Similarity	NPD6696	Suspended
0.6875	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD74	Approved
0.6875	Remote Similarity	NPD9266	Approved
0.687	Remote Similarity	NPD498	Approved
0.687	Remote Similarity	NPD495	Approved
0.687	Remote Similarity	NPD496	Approved
0.687	Remote Similarity	NPD1241	Discontinued
0.6861	Remote Similarity	NPD9269	Phase 2
0.6842	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9493	Approved
0.6835	Remote Similarity	NPD2797	Approved
0.6835	Remote Similarity	NPD3094	Phase 2
0.6831	Remote Similarity	NPD3268	Approved
0.6825	Remote Similarity	NPD1237	Approved
0.6824	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2800	Approved
0.6822	Remote Similarity	NPD1792	Phase 2
0.6815	Remote Similarity	NPD4093	Discontinued
0.6815	Remote Similarity	NPD9268	Approved
0.6812	Remote Similarity	NPD4749	Approved
0.6803	Remote Similarity	NPD1471	Phase 3
0.6797	Remote Similarity	NPD9267	Approved
0.6797	Remote Similarity	NPD9264	Approved
0.6797	Remote Similarity	NPD9263	Approved
0.6795	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7819	Suspended
0.679	Remote Similarity	NPD5033	Approved
0.6786	Remote Similarity	NPD8150	Discontinued
0.6783	Remote Similarity	NPD8032	Phase 2
0.6781	Remote Similarity	NPD1510	Phase 2
0.6779	Remote Similarity	NPD3750	Approved
0.6776	Remote Similarity	NPD1512	Approved
0.6767	Remote Similarity	NPD256	Approved
0.6767	Remote Similarity	NPD6671	Approved
0.6767	Remote Similarity	NPD3317	Approved
0.6767	Remote Similarity	NPD255	Approved
0.6765	Remote Similarity	NPD17	Approved
0.6765	Remote Similarity	NPD3095	Discontinued
0.6761	Remote Similarity	NPD4625	Phase 3
0.6759	Remote Similarity	NPD6651	Approved
0.6753	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1930	Approved
0.6746	Remote Similarity	NPD1929	Approved
0.6746	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2228	Approved
0.6742	Remote Similarity	NPD2229	Approved
0.6742	Remote Similarity	NPD2234	Approved
0.6739	Remote Similarity	NPD4878	Approved
0.6738	Remote Similarity	NPD9494	Approved
0.6738	Remote Similarity	NPD4208	Discontinued
0.6735	Remote Similarity	NPD2531	Phase 2
0.6735	Remote Similarity	NPD4477	Approved
0.6735	Remote Similarity	NPD2438	Suspended
0.6735	Remote Similarity	NPD4476	Approved
0.6733	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD2309	Approved
0.6721	Remote Similarity	NPD1693	Approved
0.6719	Remote Similarity	NPD1444	Approved
0.6719	Remote Similarity	NPD1445	Approved
0.6718	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2629	Approved
0.669	Remote Similarity	NPD230	Phase 1
0.669	Remote Similarity	NPD6355	Discontinued
0.6689	Remote Similarity	NPD7236	Approved
0.6687	Remote Similarity	NPD5027	Approved
0.6687	Remote Similarity	NPD5029	Approved
0.6687	Remote Similarity	NPD5031	Approved
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD1090	Approved
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD1086	Approved
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD1089	Approved
0.6647	Remote Similarity	NPD4955	Approved
0.6647	Remote Similarity	NPD5032	Approved
0.6647	Remote Similarity	NPD4954	Approved
0.6647	Remote Similarity	NPD5034	Approved
0.6647	Remote Similarity	NPD5026	Approved
0.6647	Remote Similarity	NPD5028	Approved
0.6647	Remote Similarity	NPD36	Approved
0.6646	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1511	Approved
0.6644	Remote Similarity	NPD4097	Suspended
0.6642	Remote Similarity	NPD1778	Approved
0.6639	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5968	Phase 3
0.6623	Remote Similarity	NPD6190	Approved
0.6618	Remote Similarity	NPD5304	Approved
0.6618	Remote Similarity	NPD5303	Approved
0.6617	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5035	Approved
0.6606	Remote Similarity	NPD5844	Phase 1
0.6605	Remote Similarity	NPD5711	Approved
0.6605	Remote Similarity	NPD5710	Approved
0.6603	Remote Similarity	NPD7028	Phase 2
0.6603	Remote Similarity	NPD4380	Phase 2
0.6597	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2313	Discontinued
0.6594	Remote Similarity	NPD4879	Approved
0.6587	Remote Similarity	NPD5030	Phase 2
0.6587	Remote Similarity	NPD5039	Approved
0.6587	Remote Similarity	NPD1242	Phase 1

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