NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	4.208
LogD:	2.941
LogS:	-3.406
# 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:	0.58
Synthetic Accessibility Score:	2.917
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.027
MDCK Permeability:	1.2998707461520098e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.77
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	95.09544372558594%
Volume Distribution (VD):	0.655
Pgp-substrate:	11.732043266296387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.236
CYP2C19-inhibitor:	0.239
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.707
CYP2C9-substrate:	0.594
CYP2D6-inhibitor:	0.636
CYP2D6-substrate:	0.284
CYP3A4-inhibitor:	0.182
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	8.952
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.673
Rat Oral Acute Toxicity:	0.667
Maximum Recommended Daily Dose:	0.867
Skin Sensitization:	0.939
Carcinogencity:	0.755
Eye Corrosion:	0.006
Eye Irritation:	0.918
Respiratory Toxicity:	0.583

Download Data

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

Natural Product: NPC477406

Natural Product ID:	NPC477406
*Common Name:**	Lantalucratin B
IUPAC Name:	6-hydroxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[g][1]benzofuran-4,5-dione
Synonyms:
Standard InCHIKey:	WKLGYQWVPPIRFC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O4/c1-7(2)11-6-9-13(17)14(18)12-8(15(9)19-11)4-3-5-10(12)16/h3-5,11,16H,1,6H2,2H3
SMILES:	CC(=C)C1CC2=C(O1)C3=C(C(=CC=C3)O)C(=O)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10060948
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
NPO8246	Lantana involucrata	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217280]
NPO8246	Lantana involucrata	Species	Verbenaceae	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	4
IC50	11
Others	1

Activity Type	# Activity
Cell Line	13
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2300	nM	PMID[15217280]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2100	nM	PMID[15217280]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1000	nM	PMID[15217280]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1800	nM	PMID[15217280]
NPT309	Cell Line	1A9	Homo sapiens	IC50	=	1500	nM	PMID[15217280]
NPT309	Cell Line	1A9	Homo sapiens	IC50	=	2100	nM	PMID[15217280]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1000	nM	PMID[15217280]
NPT307	Cell Line	HOS	Homo sapiens	IC50	=	2500	nM	PMID[15217280]
NPT308	Cell Line	CAKI-1	Homo sapiens	IC50	>	5000	nM	PMID[15217280]
NPT308	Cell Line	CAKI-1	Homo sapiens	Inhibition	=	16	%	PMID[15217280]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	210	nM	PMID[24631897]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	1000	nM	PMID[24631897]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	=	2200	nM	PMID[24631897]
NPT2	Others	Unspecified		IC50	=	2400	nM	PMID[15217280]
NPT2	Others	Unspecified		IC50	=	1900	nM	PMID[15217280]
NPT2	Others	Unspecified		GI50	=	460	nM	PMID[24631897]

☑ 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 NPC477406 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	292
0.1-0.2	1341
0.2-0.3	3126
0.3-0.4	7688
0.4-0.5	11079
0.5-0.6	4342
0.6-0.7	8287
0.7-0.8	6060
0.8-0.85	398
0.85-0.9	78
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9302	High Similarity	NPC477412
0.9084	High Similarity	NPC477407
0.8872	High Similarity	NPC59459
0.8846	High Similarity	NPC470841
0.8824	High Similarity	NPC173980
0.8815	High Similarity	NPC232996
0.8779	High Similarity	NPC237225
0.8769	High Similarity	NPC51037
0.876	High Similarity	NPC74507
0.876	High Similarity	NPC234890
0.8759	High Similarity	NPC477408
0.8741	High Similarity	NPC27407
0.8741	High Similarity	NPC281513
0.8741	High Similarity	NPC22222
0.8731	High Similarity	NPC171968
0.8731	High Similarity	NPC263817
0.8722	High Similarity	NPC205360
0.8722	High Similarity	NPC7012
0.8661	High Similarity	NPC7151
0.8661	High Similarity	NPC216297
0.8661	High Similarity	NPC473662
0.8647	High Similarity	NPC198305
0.8633	High Similarity	NPC149533
0.8623	High Similarity	NPC216312
0.8623	High Similarity	NPC29771
0.8623	High Similarity	NPC471602
0.8623	High Similarity	NPC256463
0.8623	High Similarity	NPC476477
0.8623	High Similarity	NPC306835
0.8623	High Similarity	NPC111422
0.8623	High Similarity	NPC299405
0.8615	High Similarity	NPC152525
0.8615	High Similarity	NPC68756
0.8615	High Similarity	NPC310540
0.8613	High Similarity	NPC119542
0.8605	High Similarity	NPC217756
0.8603	High Similarity	NPC142027
0.8593	High Similarity	NPC43627
0.8582	High Similarity	NPC89664
0.8582	High Similarity	NPC214702
0.8582	High Similarity	NPC477409
0.8582	High Similarity	NPC274085
0.8582	High Similarity	NPC470831
0.8561	High Similarity	NPC147542
0.8561	High Similarity	NPC327916
0.8561	High Similarity	NPC42262
0.8561	High Similarity	NPC32749
0.8561	High Similarity	NPC220496
0.8561	High Similarity	NPC241349
0.8561	High Similarity	NPC37992
0.8551	High Similarity	NPC126739
0.8551	High Similarity	NPC61590
0.8551	High Similarity	NPC197666
0.8529	High Similarity	NPC474097
0.8521	High Similarity	NPC474630
0.8519	High Similarity	NPC242358
0.8519	High Similarity	NPC246693
0.8519	High Similarity	NPC110609
0.8516	High Similarity	NPC285829
0.8516	High Similarity	NPC206778
0.8511	High Similarity	NPC476473
0.8507	High Similarity	NPC475741
0.85	High Similarity	NPC257003
0.85	High Similarity	NPC471444
0.8496	Intermediate Similarity	NPC165257
0.8496	Intermediate Similarity	NPC247250
0.8496	Intermediate Similarity	NPC767
0.8489	Intermediate Similarity	NPC114620
0.8489	Intermediate Similarity	NPC295339
0.8489	Intermediate Similarity	NPC103337
0.8485	Intermediate Similarity	NPC306765
0.8485	Intermediate Similarity	NPC231774
0.8473	Intermediate Similarity	NPC265910
0.8473	Intermediate Similarity	NPC91475
0.8462	Intermediate Similarity	NPC307174
0.8462	Intermediate Similarity	NPC46634
0.844	Intermediate Similarity	NPC329493
0.844	Intermediate Similarity	NPC474300
0.8429	Intermediate Similarity	NPC156872
0.8421	Intermediate Similarity	NPC45537
0.8406	Intermediate Similarity	NPC141934
0.8406	Intermediate Similarity	NPC291454
0.8406	Intermediate Similarity	NPC38158
0.8403	Intermediate Similarity	NPC476821
0.8397	Intermediate Similarity	NPC182646
0.8382	Intermediate Similarity	NPC309430
0.838	Intermediate Similarity	NPC21873
0.837	Intermediate Similarity	NPC136588
0.837	Intermediate Similarity	NPC199253
0.8369	Intermediate Similarity	NPC84273
0.8359	Intermediate Similarity	NPC41567
0.8357	Intermediate Similarity	NPC268052
0.8346	Intermediate Similarity	NPC477453
0.8346	Intermediate Similarity	NPC3224
0.8346	Intermediate Similarity	NPC108288
0.8346	Intermediate Similarity	NPC1991
0.8345	Intermediate Similarity	NPC301915
0.8345	Intermediate Similarity	NPC284184
0.8345	Intermediate Similarity	NPC261292
0.8345	Intermediate Similarity	NPC301341
0.8322	Intermediate Similarity	NPC103910
0.8322	Intermediate Similarity	NPC475201
0.8321	Intermediate Similarity	NPC52407
0.831	Intermediate Similarity	NPC69755
0.8298	Intermediate Similarity	NPC477535
0.8298	Intermediate Similarity	NPC477537
0.8296	Intermediate Similarity	NPC278928
0.8295	Intermediate Similarity	NPC232178
0.8288	Intermediate Similarity	NPC478219
0.8286	Intermediate Similarity	NPC33144
0.8286	Intermediate Similarity	NPC478200
0.8286	Intermediate Similarity	NPC221104
0.8286	Intermediate Similarity	NPC98395
0.8286	Intermediate Similarity	NPC191835
0.8284	Intermediate Similarity	NPC471530
0.8284	Intermediate Similarity	NPC181715
0.8276	Intermediate Similarity	NPC252208
0.8276	Intermediate Similarity	NPC478018
0.8273	Intermediate Similarity	NPC235115
0.8273	Intermediate Similarity	NPC315275
0.8271	Intermediate Similarity	NPC287473
0.8268	Intermediate Similarity	NPC161304
0.8264	Intermediate Similarity	NPC478019
0.8258	Intermediate Similarity	NPC375356
0.8258	Intermediate Similarity	NPC135062
0.8254	Intermediate Similarity	NPC477411
0.8252	Intermediate Similarity	NPC472006
0.8252	Intermediate Similarity	NPC478202
0.8248	Intermediate Similarity	NPC70622
0.8248	Intermediate Similarity	NPC470160
0.8248	Intermediate Similarity	NPC17843
0.8239	Intermediate Similarity	NPC313123
0.8239	Intermediate Similarity	NPC158634
0.8239	Intermediate Similarity	NPC470842
0.8239	Intermediate Similarity	NPC478217
0.8239	Intermediate Similarity	NPC90411
0.8239	Intermediate Similarity	NPC124365
0.8239	Intermediate Similarity	NPC283292
0.8235	Intermediate Similarity	NPC117609
0.8235	Intermediate Similarity	NPC147757
0.8227	Intermediate Similarity	NPC32360
0.8227	Intermediate Similarity	NPC1268
0.8227	Intermediate Similarity	NPC275356
0.8214	Intermediate Similarity	NPC70380
0.8214	Intermediate Similarity	NPC305060
0.8214	Intermediate Similarity	NPC71256
0.8209	Intermediate Similarity	NPC160499
0.8209	Intermediate Similarity	NPC96915
0.8209	Intermediate Similarity	NPC49647
0.8209	Intermediate Similarity	NPC136342
0.8209	Intermediate Similarity	NPC227741
0.8209	Intermediate Similarity	NPC295202
0.8207	Intermediate Similarity	NPC300540
0.8207	Intermediate Similarity	NPC470570
0.8207	Intermediate Similarity	NPC107625
0.82	Intermediate Similarity	NPC478223
0.8195	Intermediate Similarity	NPC4012
0.8194	Intermediate Similarity	NPC48762
0.8194	Intermediate Similarity	NPC193703
0.8194	Intermediate Similarity	NPC471451
0.8194	Intermediate Similarity	NPC21599
0.8194	Intermediate Similarity	NPC151607
0.8194	Intermediate Similarity	NPC42540
0.8188	Intermediate Similarity	NPC314048
0.8188	Intermediate Similarity	NPC153783
0.8188	Intermediate Similarity	NPC254603
0.8182	Intermediate Similarity	NPC300274
0.8182	Intermediate Similarity	NPC49108
0.8182	Intermediate Similarity	NPC11314
0.8175	Intermediate Similarity	NPC141549
0.8169	Intermediate Similarity	NPC155205
0.8168	Intermediate Similarity	NPC190971
0.8163	Intermediate Similarity	NPC4423
0.8163	Intermediate Similarity	NPC77325
0.8162	Intermediate Similarity	NPC34414
0.8162	Intermediate Similarity	NPC146647
0.8156	Intermediate Similarity	NPC212693
0.8156	Intermediate Similarity	NPC472602
0.8156	Intermediate Similarity	NPC94248
0.8151	Intermediate Similarity	NPC53362
0.8151	Intermediate Similarity	NPC119767
0.8151	Intermediate Similarity	NPC166583
0.8151	Intermediate Similarity	NPC71055
0.8146	Intermediate Similarity	NPC294300
0.8146	Intermediate Similarity	NPC317900
0.8146	Intermediate Similarity	NPC476404
0.8143	Intermediate Similarity	NPC86524
0.8138	Intermediate Similarity	NPC160777
0.8138	Intermediate Similarity	NPC34482
0.8138	Intermediate Similarity	NPC73416
0.8138	Intermediate Similarity	NPC83272
0.8134	Intermediate Similarity	NPC240744
0.8134	Intermediate Similarity	NPC131799
0.8134	Intermediate Similarity	NPC167055
0.8134	Intermediate Similarity	NPC103540
0.8129	Intermediate Similarity	NPC50924
0.8129	Intermediate Similarity	NPC175943
0.8125	Intermediate Similarity	NPC51106
0.8125	Intermediate Similarity	NPC469542
0.8125	Intermediate Similarity	NPC159721

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 NPC477406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	896
0.2-0.3	1376
0.3-0.4	2473
0.4-0.5	2183
0.5-0.6	1294
0.6-0.7	546
0.7-0.8	120
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8346	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD1470	Approved
0.8106	Intermediate Similarity	NPD1201	Approved
0.8028	Intermediate Similarity	NPD2346	Discontinued
0.7972	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD2344	Approved
0.7891	Intermediate Similarity	NPD2532	Approved
0.7891	Intermediate Similarity	NPD2533	Approved
0.7891	Intermediate Similarity	NPD2534	Approved
0.78	Intermediate Similarity	NPD3226	Approved
0.7786	Intermediate Similarity	NPD9493	Approved
0.7778	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1510	Phase 2
0.7746	Intermediate Similarity	NPD1607	Approved
0.773	Intermediate Similarity	NPD1240	Approved
0.7724	Intermediate Similarity	NPD1549	Phase 2
0.7708	Intermediate Similarity	NPD2935	Discontinued
0.7704	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2309	Approved
0.7674	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1471	Phase 3
0.7647	Intermediate Similarity	NPD1934	Approved
0.7597	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2313	Discontinued
0.7556	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2798	Approved
0.7552	Intermediate Similarity	NPD447	Suspended
0.7551	Intermediate Similarity	NPD2800	Approved
0.7537	Intermediate Similarity	NPD9545	Approved
0.7533	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6959	Discontinued
0.7518	Intermediate Similarity	NPD9717	Approved
0.7517	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD943	Approved
0.7482	Intermediate Similarity	NPD1203	Approved
0.7467	Intermediate Similarity	NPD1511	Approved
0.7465	Intermediate Similarity	NPD3764	Approved
0.7465	Intermediate Similarity	NPD411	Approved
0.7403	Intermediate Similarity	NPD4380	Phase 2
0.74	Intermediate Similarity	NPD3300	Phase 2
0.7389	Intermediate Similarity	NPD3882	Suspended
0.7383	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD9494	Approved
0.7375	Intermediate Similarity	NPD6232	Discontinued
0.7372	Intermediate Similarity	NPD2801	Approved
0.7368	Intermediate Similarity	NPD1512	Approved
0.7351	Intermediate Similarity	NPD7390	Discontinued
0.7347	Intermediate Similarity	NPD1551	Phase 2
0.7347	Intermediate Similarity	NPD2796	Approved
0.7346	Intermediate Similarity	NPD7473	Discontinued
0.7325	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD230	Phase 1
0.731	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2932	Approved
0.7297	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1241	Discontinued
0.7286	Intermediate Similarity	NPD1876	Approved
0.7286	Intermediate Similarity	NPD1283	Approved
0.7267	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD5711	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7267	Intermediate Similarity	NPD5710	Approved
0.7266	Intermediate Similarity	NPD1608	Approved
0.7266	Intermediate Similarity	NPD3972	Approved
0.7233	Intermediate Similarity	NPD3749	Approved
0.7226	Intermediate Similarity	NPD1651	Approved
0.7226	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8150	Discontinued
0.7203	Intermediate Similarity	NPD6832	Phase 2
0.72	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6844	Discontinued
0.7195	Intermediate Similarity	NPD3818	Discontinued
0.719	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1019	Discontinued
0.7178	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6166	Phase 2
0.7176	Intermediate Similarity	NPD74	Approved
0.7176	Intermediate Similarity	NPD9266	Approved
0.7174	Intermediate Similarity	NPD4626	Approved
0.7174	Intermediate Similarity	NPD3019	Approved
0.7143	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7075	Discontinued
0.7125	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5404	Approved
0.7114	Intermediate Similarity	NPD5406	Approved
0.7114	Intermediate Similarity	NPD6099	Approved
0.7114	Intermediate Similarity	NPD5405	Approved
0.7114	Intermediate Similarity	NPD5408	Approved
0.7114	Intermediate Similarity	NPD6100	Approved
0.7113	Intermediate Similarity	NPD1164	Approved
0.7107	Intermediate Similarity	NPD2296	Approved
0.7103	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3268	Approved
0.7101	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5691	Approved
0.7099	Intermediate Similarity	NPD9267	Approved
0.7099	Intermediate Similarity	NPD9264	Approved
0.7099	Intermediate Similarity	NPD9263	Approved
0.7097	Intermediate Similarity	NPD920	Approved
0.7078	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1281	Approved
0.707	Intermediate Similarity	NPD6599	Discontinued
0.7055	Intermediate Similarity	NPD6663	Approved
0.7052	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD17	Approved
0.705	Intermediate Similarity	NPD1778	Approved
0.7047	Intermediate Similarity	NPD4308	Phase 3
0.7047	Intermediate Similarity	NPD7033	Discontinued
0.7045	Intermediate Similarity	NPD2182	Approved
0.7044	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8313	Approved
0.7041	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD7003	Approved
0.7039	Intermediate Similarity	NPD8166	Discontinued
0.7027	Intermediate Similarity	NPD6651	Approved
0.7025	Intermediate Similarity	NPD7411	Suspended
0.7014	Intermediate Similarity	NPD5736	Approved
0.7013	Intermediate Similarity	NPD6799	Approved
0.7007	Intermediate Similarity	NPD2979	Phase 3
0.7006	Intermediate Similarity	NPD7074	Phase 3
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD2651	Approved
0.7006	Intermediate Similarity	NPD2649	Approved
0.7	Intermediate Similarity	NPD164	Approved
0.7	Intermediate Similarity	NPD5402	Approved
0.7	Intermediate Similarity	NPD3496	Discontinued
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD2797	Approved
0.6985	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6355	Discontinued
0.6957	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7236	Approved
0.6946	Remote Similarity	NPD7054	Approved
0.6946	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD5647	Approved
0.6939	Remote Similarity	NPD520	Approved
0.6934	Remote Similarity	NPD6671	Approved
0.6933	Remote Similarity	NPD3748	Approved
0.6933	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD288	Approved
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6559	Discontinued
0.6918	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7472	Approved
0.6903	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4060	Phase 1
0.689	Remote Similarity	NPD1247	Approved
0.6886	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD6280	Approved
0.6875	Remote Similarity	NPD3266	Approved
0.6875	Remote Similarity	NPD6279	Approved
0.6875	Remote Similarity	NPD3267	Approved
0.6875	Remote Similarity	NPD6801	Discontinued
0.687	Remote Similarity	NPD1237	Approved
0.6867	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6797	Phase 2
0.6863	Remote Similarity	NPD1243	Approved
0.6861	Remote Similarity	NPD9281	Approved
0.6859	Remote Similarity	NPD4661	Approved
0.6859	Remote Similarity	NPD4662	Approved
0.6853	Remote Similarity	NPD1755	Approved
0.6853	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7768	Phase 2
0.685	Remote Similarity	NPD844	Approved
0.6845	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5760	Phase 2
0.6832	Remote Similarity	NPD5761	Phase 2
0.6832	Remote Similarity	NPD1465	Phase 2
0.6831	Remote Similarity	NPD1611	Approved
0.6824	Remote Similarity	NPD7251	Discontinued
0.6821	Remote Similarity	NPD8434	Phase 2
0.6818	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6212	Phase 3
0.6818	Remote Similarity	NPD6213	Phase 3
0.6797	Remote Similarity	NPD2424	Discontinued
0.6794	Remote Similarity	NPD9261	Approved
0.6786	Remote Similarity	NPD7177	Discontinued
0.6784	Remote Similarity	NPD4954	Approved
0.6784	Remote Similarity	NPD5034	Approved
0.6784	Remote Similarity	NPD4955	Approved
0.6784	Remote Similarity	NPD7808	Phase 3
0.6784	Remote Similarity	NPD5026	Approved
0.6784	Remote Similarity	NPD5028	Approved
0.6784	Remote Similarity	NPD36	Approved
0.6784	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1481	Phase 2
0.6781	Remote Similarity	NPD2861	Phase 2

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