NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.09
Volume:	267.538
LogP:	3.214
LogD:	3.263
LogS:	-3.961
# Rotatable Bonds:	2
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.894
Synthetic Accessibility Score:	2.301
Fsp3:	0.125
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:	-4.958
MDCK Permeability:	1.5596684534102678e-05
Pgp-inhibitor:	0.38
Pgp-substrate:	0.815
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.362
Plasma Protein Binding (PPB):	96.80812072753906%
Volume Distribution (VD):	0.884
Pgp-substrate:	3.0071189403533936%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.805
CYP2C19-substrate:	0.214
CYP2C9-inhibitor:	0.639
CYP2C9-substrate:	0.817
CYP2D6-inhibitor:	0.704
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.473
CYP3A4-substrate:	0.592

ADMET: Excretion

Clearance (CL):	11.901
Half-life (T1/2):	0.63

ADMET: Toxicity

hERG Blockers:	0.248
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.319
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.636
Skin Sensitization:	0.605
Carcinogencity:	0.658
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.444

Download Data

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

Natural Product: NPC106215

Natural Product ID:	NPC106215
*Common Name:**	Dalbergichromene
IUPAC Name:	7-methoxy-4-phenyl-2H-chromen-6-ol
Synonyms:
Standard InCHIKey:	WZIKSEWGSSYQHA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O3/c1-18-16-10-15-13(9-14(16)17)12(7-8-19-15)11-5-3-2-4-6-11/h2-7,9-10,17H,8H2,1H3
SMILES:	COc1cc2OCC=C(c2cc1O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289674
PubChem CID:	5316291
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0002582] Neoflavenes

*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
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	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
EC50	1
Others	1

Activity Type	# Activity
CELL-LINE	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT23156	CELL-LINE	Calvarial osteoblast	n.a.	Emax	=	10.0	nM	PMID[456493]
NPT23156	CELL-LINE	Calvarial osteoblast	n.a.	EC50	=	1700.0	nM	PMID[456493]

☑ 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 NPC106215 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	437
0.1-0.2	1805
0.2-0.3	5665
0.3-0.4	13196
0.4-0.5	3951
0.5-0.6	4134
0.6-0.7	6262
0.7-0.8	5365
0.8-0.85	1074
0.85-0.9	517
0.9-0.95	237
0.95-1	54

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC276490
0.9618	High Similarity	NPC474282
0.9618	High Similarity	NPC176051
0.9618	High Similarity	NPC107551
0.9618	High Similarity	NPC102904
0.9618	High Similarity	NPC103976
0.9618	High Similarity	NPC326797
0.9612	High Similarity	NPC168059
0.9612	High Similarity	NPC229442
0.9545	High Similarity	NPC25966
0.9545	High Similarity	NPC127218
0.9545	High Similarity	NPC319647
0.9545	High Similarity	NPC245207
0.9542	High Similarity	NPC472336
0.9542	High Similarity	NPC472334
0.9535	High Similarity	NPC86655
0.9535	High Similarity	NPC202762
0.9531	High Similarity	NPC91291
0.9466	High Similarity	NPC112246
0.9466	High Similarity	NPC472337
0.9466	High Similarity	NPC470356
0.9466	High Similarity	NPC474206
0.9466	High Similarity	NPC195022
0.9466	High Similarity	NPC121812
0.9466	High Similarity	NPC112939
0.9466	High Similarity	NPC94750
0.9403	High Similarity	NPC471389
0.9398	High Similarity	NPC292882
0.9394	High Similarity	NPC265433
0.9394	High Similarity	NPC173660
0.9394	High Similarity	NPC270456
0.9394	High Similarity	NPC306441
0.9394	High Similarity	NPC248727
0.9394	High Similarity	NPC16435
0.9394	High Similarity	NPC474639
0.9394	High Similarity	NPC227503
0.9394	High Similarity	NPC162659
0.9394	High Similarity	NPC230734
0.9389	High Similarity	NPC317380
0.9385	High Similarity	NPC127624
0.938	High Similarity	NPC234488
0.938	High Similarity	NPC311680
0.938	High Similarity	NPC299221
0.938	High Similarity	NPC51840
0.938	High Similarity	NPC214860
0.9333	High Similarity	NPC107161
0.9328	High Similarity	NPC254759
0.9328	High Similarity	NPC160283
0.9328	High Similarity	NPC259519
0.9323	High Similarity	NPC211549
0.9318	High Similarity	NPC234333
0.9318	High Similarity	NPC134968
0.9318	High Similarity	NPC61946
0.9318	High Similarity	NPC47398
0.9318	High Similarity	NPC151224
0.9318	High Similarity	NPC260898
0.9313	High Similarity	NPC11060
0.9313	High Similarity	NPC475840
0.9308	High Similarity	NPC474356
0.9308	High Similarity	NPC45715
0.9308	High Similarity	NPC12275
0.9302	High Similarity	NPC45824
0.9302	High Similarity	NPC58164
0.9302	High Similarity	NPC10225
0.9265	High Similarity	NPC256555
0.9265	High Similarity	NPC110067
0.9265	High Similarity	NPC34245
0.9265	High Similarity	NPC91492
0.9265	High Similarity	NPC7439
0.9259	High Similarity	NPC247291
0.9254	High Similarity	NPC471388
0.9254	High Similarity	NPC236306
0.9254	High Similarity	NPC473739
0.9254	High Similarity	NPC260741
0.9254	High Similarity	NPC70682
0.9254	High Similarity	NPC232164
0.9248	High Similarity	NPC269091
0.9248	High Similarity	NPC302701
0.9242	High Similarity	NPC310854
0.9237	High Similarity	NPC78770
0.9237	High Similarity	NPC261619
0.9237	High Similarity	NPC61477
0.9237	High Similarity	NPC6451
0.9237	High Similarity	NPC185604
0.9237	High Similarity	NPC15658
0.9237	High Similarity	NPC219876
0.9237	High Similarity	NPC126029
0.9231	High Similarity	NPC220935
0.9225	High Similarity	NPC226331
0.9225	High Similarity	NPC46274
0.9225	High Similarity	NPC63179
0.9225	High Similarity	NPC266691
0.9197	High Similarity	NPC50250
0.9197	High Similarity	NPC93323
0.9197	High Similarity	NPC12641
0.9197	High Similarity	NPC45257
0.9197	High Similarity	NPC280092
0.9191	High Similarity	NPC204347
0.9191	High Similarity	NPC59841
0.9191	High Similarity	NPC475891
0.9191	High Similarity	NPC2613
0.9185	High Similarity	NPC27495
0.9185	High Similarity	NPC309124
0.9185	High Similarity	NPC22317
0.9185	High Similarity	NPC184797
0.9173	High Similarity	NPC201357
0.9173	High Similarity	NPC164787
0.9173	High Similarity	NPC255147
0.9173	High Similarity	NPC473413
0.9173	High Similarity	NPC281521
0.9167	High Similarity	NPC263064
0.9167	High Similarity	NPC36661
0.916	High Similarity	NPC220825
0.916	High Similarity	NPC232275
0.916	High Similarity	NPC472597
0.916	High Similarity	NPC268342
0.916	High Similarity	NPC42760
0.916	High Similarity	NPC268266
0.9154	High Similarity	NPC190144
0.9147	High Similarity	NPC236791
0.9147	High Similarity	NPC210355
0.9147	High Similarity	NPC293054
0.9147	High Similarity	NPC5447
0.9147	High Similarity	NPC82679
0.9147	High Similarity	NPC324112
0.9147	High Similarity	NPC282000
0.9147	High Similarity	NPC216836
0.9147	High Similarity	NPC169474
0.9147	High Similarity	NPC124452
0.9147	High Similarity	NPC74817
0.9147	High Similarity	NPC246620
0.9147	High Similarity	NPC159968
0.9147	High Similarity	NPC50368
0.9147	High Similarity	NPC250432
0.9141	High Similarity	NPC60885
0.9141	High Similarity	NPC234400
0.9137	High Similarity	NPC21776
0.9137	High Similarity	NPC16269
0.9124	High Similarity	NPC102044
0.9124	High Similarity	NPC47633
0.9124	High Similarity	NPC477616
0.9124	High Similarity	NPC85264
0.9118	High Similarity	NPC35216
0.9118	High Similarity	NPC311530
0.9111	High Similarity	NPC19869
0.9104	High Similarity	NPC234952
0.9104	High Similarity	NPC470802
0.9098	High Similarity	NPC170694
0.9091	High Similarity	NPC160991
0.9091	High Similarity	NPC184447
0.9091	High Similarity	NPC161203
0.9091	High Similarity	NPC16208
0.9091	High Similarity	NPC35932
0.9091	High Similarity	NPC253105
0.9091	High Similarity	NPC470752
0.9091	High Similarity	NPC7903
0.9091	High Similarity	NPC201587
0.9084	High Similarity	NPC224157
0.9084	High Similarity	NPC192687
0.9084	High Similarity	NPC472338
0.9077	High Similarity	NPC19694
0.907	High Similarity	NPC28730
0.907	High Similarity	NPC223136
0.907	High Similarity	NPC18924
0.907	High Similarity	NPC78974
0.907	High Similarity	NPC44748
0.907	High Similarity	NPC214406
0.907	High Similarity	NPC103823
0.9062	High Similarity	NPC122792
0.9062	High Similarity	NPC228972
0.9058	High Similarity	NPC63879
0.9051	High Similarity	NPC472335
0.9051	High Similarity	NPC472332
0.9037	High Similarity	NPC201145
0.9037	High Similarity	NPC25111
0.9037	High Similarity	NPC90615
0.9037	High Similarity	NPC6262
0.9037	High Similarity	NPC73535
0.9037	High Similarity	NPC272157
0.903	High Similarity	NPC327382
0.9023	High Similarity	NPC94236
0.9023	High Similarity	NPC269528
0.9023	High Similarity	NPC37196
0.9015	High Similarity	NPC82503
0.9015	High Similarity	NPC309787
0.9008	High Similarity	NPC476968
0.9008	High Similarity	NPC190629
0.9008	High Similarity	NPC212015
0.9008	High Similarity	NPC469963
0.9008	High Similarity	NPC285339
0.9008	High Similarity	NPC3439
0.9008	High Similarity	NPC222004
0.9008	High Similarity	NPC273295
0.9008	High Similarity	NPC226788
0.9008	High Similarity	NPC470258
0.9008	High Similarity	NPC469951
0.9008	High Similarity	NPC202582
0.9008	High Similarity	NPC210623
0.9008	High Similarity	NPC170844
0.9008	High Similarity	NPC218856

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 NPC106215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	941
0.2-0.3	1926
0.3-0.4	2708
0.4-0.5	1549
0.5-0.6	833
0.6-0.7	637
0.7-0.8	139
0.8-0.85	12
0.85-0.9	3
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9237	High Similarity	NPD1612	Clinical (unspecified phase)
0.9237	High Similarity	NPD1613	Approved
0.9225	High Similarity	NPD1529	Clinical (unspecified phase)
0.9147	High Similarity	NPD1530	Clinical (unspecified phase)
0.9008	High Similarity	NPD3027	Phase 3
0.8661	High Similarity	NPD1548	Phase 1
0.8538	High Similarity	NPD1610	Phase 2
0.8446	Intermediate Similarity	NPD2801	Approved
0.8378	Intermediate Similarity	NPD1934	Approved
0.837	Intermediate Similarity	NPD4908	Phase 1
0.8296	Intermediate Similarity	NPD2861	Phase 2
0.8248	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1653	Approved
0.811	Intermediate Similarity	NPD228	Approved
0.8082	Intermediate Similarity	NPD1511	Approved
0.8079	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD4625	Phase 3
0.8029	Intermediate Similarity	NPD3018	Phase 2
0.8	Intermediate Similarity	NPD4749	Approved
0.7973	Intermediate Similarity	NPD1512	Approved
0.7872	Intermediate Similarity	NPD1558	Phase 1
0.7868	Intermediate Similarity	NPD2983	Phase 2
0.7868	Intermediate Similarity	NPD2982	Phase 2
0.7863	Intermediate Similarity	NPD6671	Approved
0.7857	Intermediate Similarity	NPD3882	Suspended
0.7857	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD422	Phase 1
0.7848	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6166	Phase 2
0.7848	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD2981	Phase 2
0.7792	Intermediate Similarity	NPD3817	Phase 2
0.775	Intermediate Similarity	NPD3818	Discontinued
0.7717	Intermediate Similarity	NPD968	Approved
0.771	Intermediate Similarity	NPD5283	Phase 1
0.7702	Intermediate Similarity	NPD7054	Approved
0.7654	Intermediate Similarity	NPD7074	Phase 3
0.7654	Intermediate Similarity	NPD7472	Approved
0.7643	Intermediate Similarity	NPD6234	Discontinued
0.7622	Intermediate Similarity	NPD4060	Phase 1
0.7622	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2684	Approved
0.7593	Intermediate Similarity	NPD5844	Phase 1
0.7568	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7447	Phase 1
0.7547	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD4675	Approved
0.7532	Intermediate Similarity	NPD4678	Approved
0.7519	Intermediate Similarity	NPD290	Approved
0.7515	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD3620	Phase 2
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7484	Intermediate Similarity	NPD5494	Approved
0.7483	Intermediate Similarity	NPD7212	Phase 2
0.7483	Intermediate Similarity	NPD7213	Phase 3
0.7467	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1091	Approved
0.7455	Intermediate Similarity	NPD7251	Discontinued
0.7453	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1652	Phase 2
0.745	Intermediate Similarity	NPD6674	Discontinued
0.7447	Intermediate Similarity	NPD6584	Phase 3
0.7447	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD37	Approved
0.7432	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3540	Phase 1
0.7432	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8651	Approved
0.7419	Intermediate Similarity	NPD4380	Phase 2
0.7415	Intermediate Similarity	NPD1510	Phase 2
0.741	Intermediate Similarity	NPD7808	Phase 3
0.7405	Intermediate Similarity	NPD4966	Approved
0.7405	Intermediate Similarity	NPD3021	Approved
0.7405	Intermediate Similarity	NPD4965	Approved
0.7405	Intermediate Similarity	NPD3022	Approved
0.7405	Intermediate Similarity	NPD4967	Phase 2
0.74	Intermediate Similarity	NPD3750	Approved
0.7383	Intermediate Similarity	NPD1549	Phase 2
0.7368	Intermediate Similarity	NPD7843	Approved
0.7365	Intermediate Similarity	NPD2796	Approved
0.7365	Intermediate Similarity	NPD6099	Approved
0.7365	Intermediate Similarity	NPD3539	Phase 1
0.7365	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4005	Discontinued
0.7347	Intermediate Similarity	NPD4536	Approved
0.7347	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4538	Approved
0.7342	Intermediate Similarity	NPD5402	Approved
0.7338	Intermediate Similarity	NPD3705	Approved
0.7333	Intermediate Similarity	NPD5177	Phase 3
0.7333	Intermediate Similarity	NPD7157	Approved
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7323	Intermediate Similarity	NPD1242	Phase 1
0.7319	Intermediate Similarity	NPD5846	Approved
0.7319	Intermediate Similarity	NPD6516	Phase 2
0.7317	Intermediate Similarity	NPD7228	Approved
0.7315	Intermediate Similarity	NPD7266	Discontinued
0.731	Intermediate Similarity	NPD6233	Phase 2
0.7305	Intermediate Similarity	NPD6696	Suspended
0.7297	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6331	Phase 2
0.7284	Intermediate Similarity	NPD6232	Discontinued
0.7266	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD940	Approved
0.7266	Intermediate Similarity	NPD3496	Discontinued
0.726	Intermediate Similarity	NPD1240	Approved
0.725	Intermediate Similarity	NPD7075	Discontinued
0.725	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6798	Discontinued
0.7234	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6582	Phase 2
0.7234	Intermediate Similarity	NPD6583	Phase 3
0.7233	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1247	Approved
0.7219	Intermediate Similarity	NPD8053	Approved
0.7219	Intermediate Similarity	NPD8054	Approved
0.7211	Intermediate Similarity	NPD230	Phase 1
0.7208	Intermediate Similarity	NPD4123	Phase 3
0.7181	Intermediate Similarity	NPD5588	Approved
0.7181	Intermediate Similarity	NPD5960	Phase 3
0.7172	Intermediate Similarity	NPD7095	Approved
0.7171	Intermediate Similarity	NPD3892	Phase 2
0.717	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1607	Approved
0.7161	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4750	Phase 3
0.7143	Intermediate Similarity	NPD6799	Approved
0.7133	Intermediate Similarity	NPD2797	Approved
0.7133	Intermediate Similarity	NPD2935	Discontinued
0.7124	Intermediate Similarity	NPD6190	Approved
0.7124	Intermediate Similarity	NPD2677	Approved
0.7122	Intermediate Similarity	NPD1357	Approved
0.7107	Intermediate Similarity	NPD6801	Discontinued
0.7105	Intermediate Similarity	NPD3060	Approved
0.7101	Intermediate Similarity	NPD5536	Phase 2
0.7097	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4340	Discontinued
0.7095	Intermediate Similarity	NPD5735	Approved
0.7095	Intermediate Similarity	NPD6355	Discontinued
0.7086	Intermediate Similarity	NPD1375	Discontinued
0.7078	Intermediate Similarity	NPD5058	Phase 3
0.7078	Intermediate Similarity	NPD7124	Phase 2
0.7075	Intermediate Similarity	NPD2674	Phase 3
0.7067	Intermediate Similarity	NPD7033	Discontinued
0.7067	Intermediate Similarity	NPD3748	Approved
0.7066	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3225	Approved
0.7063	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7466	Approved
0.7044	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1608	Approved
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.7039	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD9494	Approved
0.7027	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2238	Phase 2
0.7027	Intermediate Similarity	NPD943	Approved
0.702	Intermediate Similarity	NPD1551	Phase 2
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2563	Approved
0.7019	Intermediate Similarity	NPD2560	Approved
0.7013	Intermediate Similarity	NPD2219	Phase 1
0.7006	Intermediate Similarity	NPD5403	Approved
0.7006	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD291	Approved
0.7	Intermediate Similarity	NPD6111	Discontinued
0.6994	Remote Similarity	NPD919	Approved
0.6994	Remote Similarity	NPD7906	Approved
0.6993	Remote Similarity	NPD4162	Approved
0.6993	Remote Similarity	NPD4237	Approved
0.6993	Remote Similarity	NPD4236	Phase 3
0.6988	Remote Similarity	NPD27	Approved
0.6988	Remote Similarity	NPD2489	Approved
0.6987	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5401	Approved
0.6985	Remote Similarity	NPD5535	Approved
0.6981	Remote Similarity	NPD6599	Discontinued
0.698	Remote Similarity	NPD447	Suspended
0.6975	Remote Similarity	NPD7768	Phase 2
0.6974	Remote Similarity	NPD5762	Approved
0.6974	Remote Similarity	NPD5763	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