NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.09
Volume:	238.27
LogP:	3.287
LogD:	3.648
LogS:	-3.768
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	2.689
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.615
MDCK Permeability:	2.2385313059203327e-05
Pgp-inhibitor:	0.606
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.686
30% Bioavailability (F30%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.459
Plasma Protein Binding (PPB):	96.38410949707031%
Volume Distribution (VD):	0.746
Pgp-substrate:	3.1159286499023438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.771
CYP2C19-inhibitor:	0.47
CYP2C19-substrate:	0.398
CYP2C9-inhibitor:	0.484
CYP2C9-substrate:	0.77
CYP2D6-inhibitor:	0.812
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.524
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	8.36
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.638
Drug-inuced Liver Injury (DILI):	0.307
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.476
Maximum Recommended Daily Dose:	0.436
Skin Sensitization:	0.232
Carcinogencity:	0.623
Eye Corrosion:	0.004
Eye Irritation:	0.163
Respiratory Toxicity:	0.432

Download Data

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

Natural Product: NPC113397

Natural Product ID:	NPC113397
*Common Name:**	Methyl 8-Hydroxy-2,2-Dimethylchromene-6-Carboxylate
IUPAC Name:	methyl 8-hydroxy-2,2-dimethylchromene-6-carboxylate
Synonyms:
Standard InCHIKey:	AJGXTMLYNUPYFX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O4/c1-13(2)5-4-8-6-9(12(15)16-3)7-10(14)11(8)17-13/h4-7,14H,1-3H3
SMILES:	COC(=O)c1cc(O)c2c(c1)C=CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489133
PubChem CID:	44575762
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]

☑ 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	2

Activity Type	# Activity
Organism	2

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[497433]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	5.0	ug	PMID[497433]

☑ 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 NPC113397 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	354
0.1-0.2	1683
0.2-0.3	4442
0.3-0.4	9630
0.4-0.5	8063
0.5-0.6	3362
0.6-0.7	5842
0.7-0.8	7923
0.8-0.85	1254
0.85-0.9	135
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC326065
0.9197	High Similarity	NPC283823
0.9197	High Similarity	NPC159418
0.9161	High Similarity	NPC213900
0.9124	High Similarity	NPC111888
0.8978	High Similarity	NPC285776
0.8921	High Similarity	NPC239855
0.8844	High Similarity	NPC472969
0.8832	High Similarity	NPC2401
0.8828	High Similarity	NPC473090
0.8828	High Similarity	NPC469615
0.8828	High Similarity	NPC50954
0.8819	High Similarity	NPC184053
0.8803	High Similarity	NPC112068
0.8803	High Similarity	NPC25305
0.8803	High Similarity	NPC110899
0.8803	High Similarity	NPC125417
0.8803	High Similarity	NPC95679
0.88	High Similarity	NPC131121
0.8784	High Similarity	NPC107636
0.8784	High Similarity	NPC476394
0.8784	High Similarity	NPC98809
0.8768	High Similarity	NPC226855
0.8767	High Similarity	NPC275278
0.8767	High Similarity	NPC469683
0.8759	High Similarity	NPC158654
0.875	High Similarity	NPC472455
0.8733	High Similarity	NPC124842
0.8732	High Similarity	NPC475111
0.8707	High Similarity	NPC262282
0.8705	High Similarity	NPC109778
0.8701	High Similarity	NPC476980
0.8699	High Similarity	NPC134975
0.8693	High Similarity	NPC296044
0.8693	High Similarity	NPC167098
0.8686	High Similarity	NPC154275
0.8684	High Similarity	NPC180901
0.8684	High Similarity	NPC268008
0.8684	High Similarity	NPC472280
0.8684	High Similarity	NPC300757
0.8684	High Similarity	NPC234255
0.8684	High Similarity	NPC286052
0.8675	High Similarity	NPC199773
0.8654	High Similarity	NPC477689
0.8654	High Similarity	NPC234004
0.8645	High Similarity	NPC349525
0.8645	High Similarity	NPC469889
0.8636	High Similarity	NPC204879
0.8633	High Similarity	NPC94810
0.8627	High Similarity	NPC133970
0.8627	High Similarity	NPC6633
0.8627	High Similarity	NPC5322
0.8623	High Similarity	NPC281020
0.8618	High Similarity	NPC62051
0.8618	High Similarity	NPC298802
0.8613	High Similarity	NPC165556
0.8611	High Similarity	NPC112135
0.8611	High Similarity	NPC207516
0.8609	High Similarity	NPC75695
0.8601	High Similarity	NPC326847
0.8592	High Similarity	NPC155098
0.8591	High Similarity	NPC30647
0.8591	High Similarity	NPC55557
0.8591	High Similarity	NPC251188
0.8591	High Similarity	NPC61871
0.859	High Similarity	NPC83922
0.859	High Similarity	NPC472448
0.859	High Similarity	NPC8300
0.8581	High Similarity	NPC53889
0.8581	High Similarity	NPC292415
0.8581	High Similarity	NPC9370
0.8581	High Similarity	NPC157133
0.8581	High Similarity	NPC287495
0.8571	High Similarity	NPC476981
0.8571	High Similarity	NPC474681
0.8571	High Similarity	NPC298268
0.8571	High Similarity	NPC218313
0.8571	High Similarity	NPC86774
0.8571	High Similarity	NPC327457
0.8562	High Similarity	NPC230149
0.8562	High Similarity	NPC168247
0.8562	High Similarity	NPC117992
0.8562	High Similarity	NPC256925
0.8562	High Similarity	NPC152951
0.8562	High Similarity	NPC200246
0.8562	High Similarity	NPC57674
0.8562	High Similarity	NPC80489
0.8553	High Similarity	NPC471982
0.8553	High Similarity	NPC60972
0.8553	High Similarity	NPC39732
0.8553	High Similarity	NPC237994
0.8543	High Similarity	NPC29231
0.8535	High Similarity	NPC45943
0.8531	High Similarity	NPC139519
0.8526	High Similarity	NPC258331
0.8526	High Similarity	NPC103201
0.8526	High Similarity	NPC167678
0.8526	High Similarity	NPC473106
0.8526	High Similarity	NPC259456
0.8526	High Similarity	NPC29876
0.8516	High Similarity	NPC83763
0.8516	High Similarity	NPC168616
0.8516	High Similarity	NPC184755
0.8516	High Similarity	NPC74178
0.8516	High Similarity	NPC87317
0.8514	High Similarity	NPC207732
0.8514	High Similarity	NPC105213
0.8506	High Similarity	NPC471985
0.8503	High Similarity	NPC312256
0.8503	High Similarity	NPC236419
0.8497	Intermediate Similarity	NPC194095
0.8497	Intermediate Similarity	NPC33051
0.8497	Intermediate Similarity	NPC292214
0.8497	Intermediate Similarity	NPC475895
0.8497	Intermediate Similarity	NPC167091
0.8497	Intermediate Similarity	NPC327032
0.8497	Intermediate Similarity	NPC88645
0.8497	Intermediate Similarity	NPC227337
0.8497	Intermediate Similarity	NPC49402
0.8497	Intermediate Similarity	NPC271779
0.8497	Intermediate Similarity	NPC70433
0.8497	Intermediate Similarity	NPC191046
0.8497	Intermediate Similarity	NPC206238
0.8497	Intermediate Similarity	NPC273462
0.8489	Intermediate Similarity	NPC16651
0.8489	Intermediate Similarity	NPC32163
0.8487	Intermediate Similarity	NPC154345
0.8481	Intermediate Similarity	NPC130920
0.8481	Intermediate Similarity	NPC85057
0.8477	Intermediate Similarity	NPC205054
0.8477	Intermediate Similarity	NPC183950
0.8477	Intermediate Similarity	NPC223579
0.8477	Intermediate Similarity	NPC137062
0.8477	Intermediate Similarity	NPC52005
0.8477	Intermediate Similarity	NPC473091
0.8477	Intermediate Similarity	NPC287101
0.8472	Intermediate Similarity	NPC156307
0.8471	Intermediate Similarity	NPC261470
0.8471	Intermediate Similarity	NPC144843
0.8471	Intermediate Similarity	NPC474150
0.8471	Intermediate Similarity	NPC474162
0.8467	Intermediate Similarity	NPC168803
0.8467	Intermediate Similarity	NPC139839
0.8462	Intermediate Similarity	NPC328102
0.8462	Intermediate Similarity	NPC204290
0.8462	Intermediate Similarity	NPC472962
0.8462	Intermediate Similarity	NPC119209
0.8462	Intermediate Similarity	NPC118256
0.8462	Intermediate Similarity	NPC192686
0.8462	Intermediate Similarity	NPC45404
0.8462	Intermediate Similarity	NPC472961
0.8462	Intermediate Similarity	NPC130955
0.8462	Intermediate Similarity	NPC92830
0.8456	Intermediate Similarity	NPC287275
0.8456	Intermediate Similarity	NPC98356
0.8452	Intermediate Similarity	NPC247713
0.8452	Intermediate Similarity	NPC68324
0.8452	Intermediate Similarity	NPC52889
0.8452	Intermediate Similarity	NPC289322
0.8452	Intermediate Similarity	NPC114179
0.8452	Intermediate Similarity	NPC38779
0.8452	Intermediate Similarity	NPC262286
0.8452	Intermediate Similarity	NPC78225
0.8452	Intermediate Similarity	NPC27337
0.8452	Intermediate Similarity	NPC156818
0.8452	Intermediate Similarity	NPC36852
0.8452	Intermediate Similarity	NPC160512
0.8452	Intermediate Similarity	NPC291508
0.8446	Intermediate Similarity	NPC471763
0.8446	Intermediate Similarity	NPC258307
0.8442	Intermediate Similarity	NPC256612
0.8442	Intermediate Similarity	NPC39184
0.8442	Intermediate Similarity	NPC16286
0.8442	Intermediate Similarity	NPC20830
0.8435	Intermediate Similarity	NPC110419
0.8431	Intermediate Similarity	NPC120537
0.8431	Intermediate Similarity	NPC71334
0.8431	Intermediate Similarity	NPC310661
0.8431	Intermediate Similarity	NPC120163
0.8431	Intermediate Similarity	NPC295646
0.8431	Intermediate Similarity	NPC188203
0.8431	Intermediate Similarity	NPC275722
0.8431	Intermediate Similarity	NPC105827
0.8431	Intermediate Similarity	NPC156222
0.8431	Intermediate Similarity	NPC199100
0.8431	Intermediate Similarity	NPC275836
0.8431	Intermediate Similarity	NPC83508
0.8431	Intermediate Similarity	NPC239128
0.8431	Intermediate Similarity	NPC100887
0.8431	Intermediate Similarity	NPC198826
0.8431	Intermediate Similarity	NPC301323
0.8431	Intermediate Similarity	NPC289968
0.8431	Intermediate Similarity	NPC57030
0.8431	Intermediate Similarity	NPC212678
0.8431	Intermediate Similarity	NPC161277
0.8431	Intermediate Similarity	NPC39007
0.8431	Intermediate Similarity	NPC101996
0.8431	Intermediate Similarity	NPC180234
0.8431	Intermediate Similarity	NPC55205
0.8431	Intermediate Similarity	NPC293183

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 NPC113397 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	960
0.2-0.3	1837
0.3-0.4	2556
0.4-0.5	1746
0.5-0.6	1038
0.6-0.7	517
0.7-0.8	163
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8392	Intermediate Similarity	NPD230	Phase 1
0.8392	Intermediate Similarity	NPD447	Suspended
0.8387	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD2801	Approved
0.8357	Intermediate Similarity	NPD9494	Approved
0.8312	Intermediate Similarity	NPD1934	Approved
0.8267	Intermediate Similarity	NPD1511	Approved
0.8258	Intermediate Similarity	NPD1465	Phase 2
0.8258	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1512	Approved
0.8153	Intermediate Similarity	NPD3882	Suspended
0.8121	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD3817	Phase 2
0.8067	Intermediate Similarity	NPD4628	Phase 3
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7937	Intermediate Similarity	NPD919	Approved
0.7933	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD9545	Approved
0.7875	Intermediate Similarity	NPD7075	Discontinued
0.7866	Intermediate Similarity	NPD7473	Discontinued
0.7857	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD2313	Discontinued
0.7805	Intermediate Similarity	NPD6166	Phase 2
0.7805	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6190	Approved
0.7771	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD1608	Approved
0.7746	Intermediate Similarity	NPD9269	Phase 2
0.7738	Intermediate Similarity	NPD7685	Pre-registration
0.7736	Intermediate Similarity	NPD6801	Discontinued
0.7733	Intermediate Similarity	NPD2799	Discontinued
0.773	Intermediate Similarity	NPD1247	Approved
0.7725	Intermediate Similarity	NPD7074	Phase 3
0.7725	Intermediate Similarity	NPD7472	Approved
0.7722	Intermediate Similarity	NPD4380	Phase 2
0.7712	Intermediate Similarity	NPD3750	Approved
0.7707	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7819	Suspended
0.7677	Intermediate Similarity	NPD6799	Approved
0.7669	Intermediate Similarity	NPD5494	Approved
0.7643	Intermediate Similarity	NPD920	Approved
0.7632	Intermediate Similarity	NPD2346	Discontinued
0.763	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2533	Approved
0.7628	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2534	Approved
0.7628	Intermediate Similarity	NPD2532	Approved
0.7622	Intermediate Similarity	NPD9717	Approved
0.7616	Intermediate Similarity	NPD1510	Phase 2
0.7586	Intermediate Similarity	NPD1203	Approved
0.7584	Intermediate Similarity	NPD1240	Approved
0.7584	Intermediate Similarity	NPD943	Approved
0.7582	Intermediate Similarity	NPD1549	Phase 2
0.7574	Intermediate Similarity	NPD6797	Phase 2
0.7566	Intermediate Similarity	NPD1551	Phase 2
0.7562	Intermediate Similarity	NPD6386	Approved
0.7562	Intermediate Similarity	NPD6385	Approved
0.7562	Intermediate Similarity	NPD7411	Suspended
0.7558	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD17	Approved
0.7533	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1243	Approved
0.7529	Intermediate Similarity	NPD7251	Discontinued
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1607	Approved
0.7467	Intermediate Similarity	NPD1613	Approved
0.7467	Intermediate Similarity	NPD4060	Phase 1
0.7467	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9268	Approved
0.745	Intermediate Similarity	NPD411	Approved
0.745	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3764	Approved
0.7436	Intermediate Similarity	NPD2354	Approved
0.7431	Intermediate Similarity	NPD422	Phase 1
0.7423	Intermediate Similarity	NPD5402	Approved
0.7419	Intermediate Similarity	NPD2800	Approved
0.7413	Intermediate Similarity	NPD1778	Approved
0.7403	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2344	Approved
0.7394	Intermediate Similarity	NPD6234	Discontinued
0.7391	Intermediate Similarity	NPD228	Approved
0.7389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3748	Approved
0.7378	Intermediate Similarity	NPD7768	Phase 2
0.7372	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5049	Phase 3
0.7353	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2796	Approved
0.7333	Intermediate Similarity	NPD3749	Approved
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7326	Intermediate Similarity	NPD6559	Discontinued
0.7317	Intermediate Similarity	NPD5353	Approved
0.7305	Intermediate Similarity	NPD7199	Phase 2
0.7305	Intermediate Similarity	NPD8127	Discontinued
0.7303	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6355	Discontinued
0.7279	Intermediate Similarity	NPD1283	Approved
0.7279	Intermediate Similarity	NPD3225	Approved
0.7278	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7267	Intermediate Similarity	NPD3027	Phase 3
0.7261	Intermediate Similarity	NPD4110	Phase 3
0.7261	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1481	Phase 2
0.7254	Intermediate Similarity	NPD9493	Approved
0.7237	Intermediate Similarity	NPD4307	Phase 2
0.723	Intermediate Similarity	NPD2797	Approved
0.7226	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD824	Approved
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3926	Phase 2
0.7219	Intermediate Similarity	NPD3268	Approved
0.7219	Intermediate Similarity	NPD5242	Approved
0.7215	Intermediate Similarity	NPD2309	Approved
0.7212	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5403	Approved
0.7203	Intermediate Similarity	NPD5536	Phase 2
0.7195	Intermediate Similarity	NPD37	Approved
0.7192	Intermediate Similarity	NPD1535	Discovery
0.7188	Intermediate Similarity	NPD5401	Approved
0.7188	Intermediate Similarity	NPD3146	Approved
0.7188	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7179	Intermediate Similarity	NPD2353	Approved
0.7179	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4626	Approved
0.7169	Intermediate Similarity	NPD4965	Approved
0.7169	Intermediate Similarity	NPD4967	Phase 2
0.7169	Intermediate Similarity	NPD4966	Approved
0.7168	Intermediate Similarity	NPD5953	Discontinued
0.7163	Intermediate Similarity	NPD1241	Discontinued
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD7003	Approved
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7126	Intermediate Similarity	NPD7039	Approved
0.7126	Intermediate Similarity	NPD7038	Approved
0.7123	Intermediate Similarity	NPD3496	Discontinued
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.7117	Intermediate Similarity	NPD3455	Phase 2
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3887	Approved
0.7105	Intermediate Similarity	NPD1296	Phase 2
0.7101	Intermediate Similarity	NPD6959	Discontinued
0.7093	Intermediate Similarity	NPD7177	Discontinued
0.7093	Intermediate Similarity	NPD7228	Approved
0.7086	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5124	Phase 1
0.7075	Intermediate Similarity	NPD1281	Approved
0.707	Intermediate Similarity	NPD7266	Discontinued
0.707	Intermediate Similarity	NPD6004	Phase 3
0.707	Intermediate Similarity	NPD6002	Phase 3
0.707	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6005	Phase 3
0.707	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD5711	Approved
0.7048	Intermediate Similarity	NPD8455	Phase 2
0.7037	Intermediate Similarity	NPD6273	Approved
0.703	Intermediate Similarity	NPD6873	Phase 2
0.7013	Intermediate Similarity	NPD1558	Phase 1
0.7006	Intermediate Similarity	NPD4476	Approved
0.7006	Intermediate Similarity	NPD4477	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.7006	Intermediate Similarity	NPD6100	Approved
0.7	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD3266	Approved
0.6994	Remote Similarity	NPD3751	Discontinued
0.6987	Remote Similarity	NPD7097	Phase 1
0.6986	Remote Similarity	NPD5691	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