NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.09
Volume:	229.48
LogP:	3.612
LogD:	3.972
LogS:	-4.413
# Rotatable Bonds:	2
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	2.376
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.534
MDCK Permeability:	2.5079214537981898e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	94.45964050292969%
Volume Distribution (VD):	1.091
Pgp-substrate:	3.6051008701324463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.822
CYP2C19-inhibitor:	0.902
CYP2C19-substrate:	0.598
CYP2C9-inhibitor:	0.6
CYP2C9-substrate:	0.81
CYP2D6-inhibitor:	0.84
CYP2D6-substrate:	0.619
CYP3A4-inhibitor:	0.411
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	8.067
Half-life (T1/2):	0.623

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.817
Drug-inuced Liver Injury (DILI):	0.415
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.136
Skin Sensitization:	0.502
Carcinogencity:	0.865
Eye Corrosion:	0.004
Eye Irritation:	0.328
Respiratory Toxicity:	0.756

Download Data

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

Natural Product: NPC165556

Natural Product ID:	NPC165556
*Common Name:**	Methyl 2,2-Dimethylchromene-6-Carboxylate
IUPAC Name:	methyl 2,2-dimethylchromene-6-carboxylate
Synonyms:
Standard InCHIKey:	BVQOOKUOYKXECX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O3/c1-13(2)7-6-9-8-10(12(14)15-3)4-5-11(9)16-13/h4-8H,1-3H3
SMILES:	CC1(C)C=Cc2cc(ccc2O1)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489132
PubChem CID:	5316881
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO33179	piper sp.	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568762]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6061704]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8588862]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20123	Actinidia polygama	Species	Actinidiaceae	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
Others	10

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	5.0	ug	PMID[553259]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	5.0	ug	PMID[553259]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	GI	>	50.0	%	PMID[553260]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	100.0	%	PMID[553261]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	92.5	%	PMID[553261]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	3.75	%	PMID[553261]

☑ 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 NPC165556 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	347
0.1-0.2	1788
0.2-0.3	4804
0.3-0.4	10889
0.4-0.5	6832
0.5-0.6	4515
0.6-0.7	8654
0.7-0.8	4471
0.8-0.85	337
0.85-0.9	52
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC37512
0.959	High Similarity	NPC2401
0.928	High Similarity	NPC327457
0.928	High Similarity	NPC109778
0.928	High Similarity	NPC86774
0.9068	High Similarity	NPC220540
0.8943	High Similarity	NPC291189
0.8943	High Similarity	NPC69403
0.8915	High Similarity	NPC229646
0.8889	High Similarity	NPC121104
0.8864	High Similarity	NPC253616
0.8819	High Similarity	NPC125887
0.88	High Similarity	NPC221798
0.8797	High Similarity	NPC36414
0.8788	High Similarity	NPC268081
0.877	High Similarity	NPC61779
0.8769	High Similarity	NPC66158
0.875	High Similarity	NPC170546
0.875	High Similarity	NPC66246
0.872	High Similarity	NPC141252
0.872	High Similarity	NPC11799
0.8692	High Similarity	NPC470859
0.8692	High Similarity	NPC175159
0.8682	High Similarity	NPC183348
0.8682	High Similarity	NPC282230
0.8678	High Similarity	NPC470860
0.8667	High Similarity	NPC184053
0.8661	High Similarity	NPC475236
0.8661	High Similarity	NPC237868
0.8657	High Similarity	NPC473988
0.8651	High Similarity	NPC184219
0.8647	High Similarity	NPC472516
0.864	High Similarity	NPC67300
0.8626	High Similarity	NPC55147
0.8615	High Similarity	NPC470977
0.8615	High Similarity	NPC470976
0.8615	High Similarity	NPC472517
0.8615	High Similarity	NPC196979
0.8615	High Similarity	NPC15083
0.8613	High Similarity	NPC113397
0.8605	High Similarity	NPC473019
0.8593	High Similarity	NPC472515
0.8583	High Similarity	NPC470858
0.8583	High Similarity	NPC2771
0.8582	High Similarity	NPC38153
0.8571	High Similarity	NPC46869
0.8571	High Similarity	NPC151113
0.8512	High Similarity	NPC252004
0.8507	High Similarity	NPC161196
0.8496	Intermediate Similarity	NPC470844
0.8496	Intermediate Similarity	NPC61499
0.8496	Intermediate Similarity	NPC229128
0.8492	Intermediate Similarity	NPC13007
0.8492	Intermediate Similarity	NPC96286
0.8492	Intermediate Similarity	NPC257188
0.8492	Intermediate Similarity	NPC248429
0.8485	Intermediate Similarity	NPC54503
0.8467	Intermediate Similarity	NPC254010
0.8456	Intermediate Similarity	NPC136095
0.8456	Intermediate Similarity	NPC262635
0.8455	Intermediate Similarity	NPC45104
0.845	Intermediate Similarity	NPC293387
0.845	Intermediate Similarity	NPC49852
0.845	Intermediate Similarity	NPC475496
0.8444	Intermediate Similarity	NPC103001
0.8444	Intermediate Similarity	NPC332594
0.8444	Intermediate Similarity	NPC157855
0.8433	Intermediate Similarity	NPC104796
0.843	Intermediate Similarity	NPC90903
0.8425	Intermediate Similarity	NPC273772
0.8425	Intermediate Similarity	NPC154176
0.8425	Intermediate Similarity	NPC173350
0.8425	Intermediate Similarity	NPC290605
0.8425	Intermediate Similarity	NPC472518
0.8425	Intermediate Similarity	NPC109675
0.8421	Intermediate Similarity	NPC292998
0.8417	Intermediate Similarity	NPC208584
0.8417	Intermediate Similarity	NPC469953
0.8417	Intermediate Similarity	NPC171656
0.8417	Intermediate Similarity	NPC23332
0.8413	Intermediate Similarity	NPC144418
0.8409	Intermediate Similarity	NPC284424
0.8406	Intermediate Similarity	NPC313036
0.84	Intermediate Similarity	NPC230951
0.8394	Intermediate Similarity	NPC472409
0.8394	Intermediate Similarity	NPC470856
0.8387	Intermediate Similarity	NPC265547
0.8387	Intermediate Similarity	NPC94298
0.8387	Intermediate Similarity	NPC27633
0.8385	Intermediate Similarity	NPC157212
0.8385	Intermediate Similarity	NPC2596
0.8385	Intermediate Similarity	NPC473907
0.8382	Intermediate Similarity	NPC17848
0.8374	Intermediate Similarity	NPC131192
0.8359	Intermediate Similarity	NPC107846
0.8359	Intermediate Similarity	NPC27671
0.8359	Intermediate Similarity	NPC73413
0.8359	Intermediate Similarity	NPC111347
0.8359	Intermediate Similarity	NPC89630
0.8359	Intermediate Similarity	NPC201667
0.8358	Intermediate Similarity	NPC125920
0.8358	Intermediate Similarity	NPC66705
0.8357	Intermediate Similarity	NPC286038
0.8333	Intermediate Similarity	NPC103362
0.8333	Intermediate Similarity	NPC183648
0.8333	Intermediate Similarity	NPC301717
0.8321	Intermediate Similarity	NPC939
0.8321	Intermediate Similarity	NPC23257
0.8321	Intermediate Similarity	NPC473894
0.8321	Intermediate Similarity	NPC473076
0.8321	Intermediate Similarity	NPC11566
0.8321	Intermediate Similarity	NPC473209
0.832	Intermediate Similarity	NPC281356
0.832	Intermediate Similarity	NPC298796
0.8309	Intermediate Similarity	NPC221046
0.8306	Intermediate Similarity	NPC469954
0.8306	Intermediate Similarity	NPC183154
0.8306	Intermediate Similarity	NPC217423
0.8306	Intermediate Similarity	NPC263754
0.8298	Intermediate Similarity	NPC66991
0.8298	Intermediate Similarity	NPC129650
0.8296	Intermediate Similarity	NPC163029
0.8296	Intermediate Similarity	NPC60667
0.8293	Intermediate Similarity	NPC188907
0.8286	Intermediate Similarity	NPC294365
0.8284	Intermediate Similarity	NPC247743
0.8284	Intermediate Similarity	NPC108113
0.8284	Intermediate Similarity	NPC93756
0.8273	Intermediate Similarity	NPC51146
0.8273	Intermediate Similarity	NPC472840
0.8273	Intermediate Similarity	NPC11561
0.8273	Intermediate Similarity	NPC166858
0.8273	Intermediate Similarity	NPC226636
0.8271	Intermediate Similarity	NPC278556
0.8271	Intermediate Similarity	NPC302844
0.8264	Intermediate Similarity	NPC233238
0.8264	Intermediate Similarity	NPC57879
0.8261	Intermediate Similarity	NPC475680
0.8261	Intermediate Similarity	NPC150522
0.8261	Intermediate Similarity	NPC305355
0.8261	Intermediate Similarity	NPC471587
0.8258	Intermediate Similarity	NPC307732
0.8258	Intermediate Similarity	NPC42292
0.8248	Intermediate Similarity	NPC470668
0.8248	Intermediate Similarity	NPC131130
0.8248	Intermediate Similarity	NPC470669
0.8248	Intermediate Similarity	NPC71903
0.8244	Intermediate Similarity	NPC185066
0.8244	Intermediate Similarity	NPC473744
0.8244	Intermediate Similarity	NPC472519
0.824	Intermediate Similarity	NPC96705
0.824	Intermediate Similarity	NPC152306
0.8239	Intermediate Similarity	NPC211811
0.8239	Intermediate Similarity	NPC266743
0.8235	Intermediate Similarity	NPC174999
0.8235	Intermediate Similarity	NPC254741
0.8231	Intermediate Similarity	NPC234109
0.8231	Intermediate Similarity	NPC471826
0.8231	Intermediate Similarity	NPC154275
0.8231	Intermediate Similarity	NPC188327
0.8226	Intermediate Similarity	NPC128633
0.8217	Intermediate Similarity	NPC255073
0.8217	Intermediate Similarity	NPC291899
0.8214	Intermediate Similarity	NPC213900
0.8214	Intermediate Similarity	NPC17262
0.8214	Intermediate Similarity	NPC59522
0.8209	Intermediate Similarity	NPC101294
0.8209	Intermediate Similarity	NPC473655
0.8201	Intermediate Similarity	NPC156590
0.8201	Intermediate Similarity	NPC64908
0.8201	Intermediate Similarity	NPC147688
0.8201	Intermediate Similarity	NPC201820
0.8201	Intermediate Similarity	NPC118840
0.8201	Intermediate Similarity	NPC110969
0.8201	Intermediate Similarity	NPC205006
0.8195	Intermediate Similarity	NPC279596
0.8195	Intermediate Similarity	NPC104854
0.8195	Intermediate Similarity	NPC473777
0.8189	Intermediate Similarity	NPC235190
0.8189	Intermediate Similarity	NPC163200
0.8189	Intermediate Similarity	NPC180006
0.8188	Intermediate Similarity	NPC310370
0.8188	Intermediate Similarity	NPC170812
0.8188	Intermediate Similarity	NPC78913
0.8188	Intermediate Similarity	NPC183642
0.8188	Intermediate Similarity	NPC18260
0.8182	Intermediate Similarity	NPC164299
0.8182	Intermediate Similarity	NPC473809
0.8182	Intermediate Similarity	NPC88445
0.8175	Intermediate Similarity	NPC62735
0.8175	Intermediate Similarity	NPC259685
0.8169	Intermediate Similarity	NPC282335
0.8169	Intermediate Similarity	NPC180477
0.8169	Intermediate Similarity	NPC218300
0.8169	Intermediate Similarity	NPC74539
0.8169	Intermediate Similarity	NPC304443
0.8168	Intermediate Similarity	NPC22783
0.8162	Intermediate Similarity	NPC101752
0.8156	Intermediate Similarity	NPC246903
0.8156	Intermediate Similarity	NPC474044

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 NPC165556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	1017
0.2-0.3	1563
0.3-0.4	2624
0.4-0.5	1778
0.5-0.6	1228
0.6-0.7	455
0.7-0.8	155
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8593	High Similarity	NPD7421	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1243	Approved
0.8387	Intermediate Similarity	NPD9545	Approved
0.8279	Intermediate Similarity	NPD1241	Discontinued
0.8273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD17	Approved
0.8235	Intermediate Similarity	NPD2796	Approved
0.8169	Intermediate Similarity	NPD920	Approved
0.8162	Intermediate Similarity	NPD3748	Approved
0.8156	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD9697	Approved
0.8062	Intermediate Similarity	NPD9717	Approved
0.8062	Intermediate Similarity	NPD1608	Approved
0.8029	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD4307	Phase 2
0.7985	Intermediate Similarity	NPD1296	Phase 2
0.7985	Intermediate Similarity	NPD2313	Discontinued
0.7985	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD6832	Phase 2
0.7958	Intermediate Similarity	NPD6799	Approved
0.7955	Intermediate Similarity	NPD1019	Discontinued
0.7945	Intermediate Similarity	NPD7411	Suspended
0.7923	Intermediate Similarity	NPD3972	Approved
0.7902	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6801	Discontinued
0.7883	Intermediate Similarity	NPD1607	Approved
0.7879	Intermediate Similarity	NPD3267	Approved
0.7879	Intermediate Similarity	NPD3266	Approved
0.7879	Intermediate Similarity	NPD1203	Approved
0.7872	Intermediate Similarity	NPD3750	Approved
0.7857	Intermediate Similarity	NPD1549	Phase 2
0.7857	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD422	Phase 1
0.7838	Intermediate Similarity	NPD7819	Suspended
0.7838	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD2353	Approved
0.7786	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1510	Phase 2
0.777	Intermediate Similarity	NPD4308	Phase 3
0.7755	Intermediate Similarity	NPD6599	Discontinued
0.7748	Intermediate Similarity	NPD919	Approved
0.7744	Intermediate Similarity	NPD2797	Approved
0.7714	Intermediate Similarity	NPD1551	Phase 2
0.7714	Intermediate Similarity	NPD2935	Discontinued
0.771	Intermediate Similarity	NPD1281	Approved
0.7705	Intermediate Similarity	NPD3134	Approved
0.7692	Intermediate Similarity	NPD1778	Approved
0.7692	Intermediate Similarity	NPD3887	Approved
0.7682	Intermediate Similarity	NPD7075	Discontinued
0.7681	Intermediate Similarity	NPD1933	Approved
0.7681	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3225	Approved
0.766	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD9493	Approved
0.7643	Intermediate Similarity	NPD7033	Discontinued
0.7642	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD1358	Approved
0.7615	Intermediate Similarity	NPD5691	Approved
0.7609	Intermediate Similarity	NPD3142	Approved
0.7609	Intermediate Similarity	NPD3140	Approved
0.7591	Intermediate Similarity	NPD3268	Approved
0.7574	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2354	Approved
0.7568	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD2798	Approved
0.7538	Intermediate Similarity	NPD1894	Discontinued
0.7537	Intermediate Similarity	NPD1283	Approved
0.7537	Intermediate Similarity	NPD1876	Approved
0.7535	Intermediate Similarity	NPD2346	Discontinued
0.7535	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7483	Intermediate Similarity	NPD5049	Phase 3
0.7483	Intermediate Similarity	NPD2186	Approved
0.748	Intermediate Similarity	NPD5535	Approved
0.7465	Intermediate Similarity	NPD4476	Approved
0.7465	Intermediate Similarity	NPD4477	Approved
0.7464	Intermediate Similarity	NPD3764	Approved
0.7464	Intermediate Similarity	NPD411	Approved
0.7464	Intermediate Similarity	NPD6798	Discontinued
0.7434	Intermediate Similarity	NPD3817	Phase 2
0.7429	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD5124	Phase 1
0.7429	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4626	Approved
0.7415	Intermediate Similarity	NPD5401	Approved
0.7402	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4380	Phase 2
0.7389	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1481	Phase 2
0.7379	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1238	Approved
0.7348	Intermediate Similarity	NPD1651	Approved
0.7347	Intermediate Similarity	NPD1511	Approved
0.7338	Intermediate Similarity	NPD3749	Approved
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.7329	Intermediate Similarity	NPD2309	Approved
0.732	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD9261	Approved
0.7315	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5403	Approved
0.7313	Intermediate Similarity	NPD1535	Discovery
0.731	Intermediate Similarity	NPD2800	Approved
0.7308	Intermediate Similarity	NPD1247	Approved
0.7305	Intermediate Similarity	NPD230	Phase 1
0.7305	Intermediate Similarity	NPD6355	Discontinued
0.7297	Intermediate Similarity	NPD2533	Approved
0.7297	Intermediate Similarity	NPD2534	Approved
0.7297	Intermediate Similarity	NPD2532	Approved
0.7296	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1471	Phase 3
0.7285	Intermediate Similarity	NPD6585	Discontinued
0.7279	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5844	Phase 1
0.7248	Intermediate Similarity	NPD6273	Approved
0.7248	Intermediate Similarity	NPD1512	Approved
0.7246	Intermediate Similarity	NPD9494	Approved
0.7244	Intermediate Similarity	NPD5494	Approved
0.7237	Intermediate Similarity	NPD5890	Approved
0.7237	Intermediate Similarity	NPD5889	Approved
0.7234	Intermediate Similarity	NPD2979	Phase 3
0.723	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5585	Approved
0.7208	Intermediate Similarity	NPD4288	Approved
0.719	Intermediate Similarity	NPD1934	Approved
0.7185	Intermediate Similarity	NPD1611	Approved
0.7183	Intermediate Similarity	NPD4618	Approved
0.7183	Intermediate Similarity	NPD4622	Approved
0.7172	Intermediate Similarity	NPD6004	Phase 3
0.7172	Intermediate Similarity	NPD6005	Phase 3
0.7172	Intermediate Similarity	NPD6002	Phase 3
0.7172	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8032	Phase 2
0.716	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD2801	Approved
0.7133	Intermediate Similarity	NPD6651	Approved
0.7124	Intermediate Similarity	NPD6386	Approved
0.7124	Intermediate Similarity	NPD6385	Approved
0.7122	Intermediate Similarity	NPD454	Approved
0.7111	Intermediate Similarity	NPD3496	Discontinued
0.7111	Intermediate Similarity	NPD3847	Discontinued
0.7105	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1164	Approved
0.709	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD9264	Approved
0.7087	Intermediate Similarity	NPD9263	Approved
0.7087	Intermediate Similarity	NPD9267	Approved
0.7083	Intermediate Similarity	NPD5688	Approved
0.7083	Intermediate Similarity	NPD5689	Approved
0.7081	Intermediate Similarity	NPD7177	Discontinued
0.7075	Intermediate Similarity	NPD2654	Approved
0.7067	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3882	Suspended
0.7047	Intermediate Similarity	NPD7440	Discontinued
0.7044	Intermediate Similarity	NPD6232	Discontinued
0.7042	Intermediate Similarity	NPD6233	Phase 2
0.7042	Intermediate Similarity	NPD4062	Phase 3
0.7039	Intermediate Similarity	NPD957	Approved
0.7037	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1465	Phase 2
0.7031	Intermediate Similarity	NPD9266	Approved
0.7031	Intermediate Similarity	NPD2684	Approved
0.7031	Intermediate Similarity	NPD74	Approved
0.7013	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4060	Phase 1
0.6987	Remote Similarity	NPD5402	Approved
0.6986	Remote Similarity	NPD2531	Phase 2
0.6986	Remote Similarity	NPD6099	Approved
0.6986	Remote Similarity	NPD6100	Approved
0.6986	Remote Similarity	NPD2438	Suspended
0.6984	Remote Similarity	NPD164	Approved
0.6974	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6279	Approved
0.6968	Remote Similarity	NPD6280	Approved
0.6966	Remote Similarity	NPD7097	Phase 1
0.6959	Remote Similarity	NPD1652	Phase 2
0.6957	Remote Similarity	NPD4359	Approved
0.6957	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3146	Approved
0.6954	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD290	Approved
0.695	Remote Similarity	NPD2614	Approved
0.6944	Remote Similarity	NPD4340	Discontinued
0.694	Remote Similarity	NPD5536	Phase 2
0.6937	Remote Similarity	NPD6808	Phase 2
0.6934	Remote Similarity	NPD1610	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