NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.09
Volume:	249.747
LogP:	0.203
LogD:	0.967
LogS:	-1.647
# Rotatable Bonds:	6
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	2.651
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.663
MDCK Permeability:	5.7970806665252894e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	24.511690139770508%
Volume Distribution (VD):	0.842
Pgp-substrate:	52.634334564208984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.628
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.643

ADMET: Excretion

Clearance (CL):	9.326
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.234
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.18
Carcinogencity:	0.028
Eye Corrosion:	0.005
Eye Irritation:	0.092
Respiratory Toxicity:	0.059

Download Data

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

Natural Product: NPC203351

Natural Product ID:	NPC203351
*Common Name:**	Berfussinol
IUPAC Name:	methyl (2S)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
Synonyms:	Berfussinol
Standard InCHIKey:	YGUTYWCRKWUWOT-MRVPVSSYSA-N
Standard InCHI:	InChI=1S/C12H16O6/c1-16-9-4-7(5-10(17-2)11(9)14)8(6-13)12(15)18-3/h4-5,8,13-14H,6H2,1-3H3/t8-/m1/s1
SMILES:	COC(=O)[C@@H](c1cc(OC)c(c(c1)OC)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1760595
PubChem CID:	54586911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	trunk	Jeju island, Korea	2005-Dec	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[529383]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	27170.0	nM	PMID[529383]
NPT574	Cell Line	XF498	Homo sapiens	IC50	>	30000.0	nM	PMID[529383]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[529383]

☑ 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 NPC203351 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	315
0.1-0.2	1374
0.2-0.3	3946
0.3-0.4	8843
0.4-0.5	9643
0.5-0.6	3716
0.6-0.7	6169
0.7-0.8	7728
0.8-0.85	887
0.85-0.9	71
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC470991
0.9143	High Similarity	NPC27159
0.9118	High Similarity	NPC470990
0.8993	High Similarity	NPC4796
0.8958	High Similarity	NPC474903
0.8947	High Similarity	NPC281020
0.8939	High Similarity	NPC173608
0.8936	High Similarity	NPC470811
0.8936	High Similarity	NPC106920
0.8936	High Similarity	NPC477696
0.8936	High Similarity	NPC273657
0.8936	High Similarity	NPC477697
0.8912	High Similarity	NPC281477
0.8851	High Similarity	NPC16082
0.8851	High Similarity	NPC82592
0.8849	High Similarity	NPC125417
0.8849	High Similarity	NPC25305
0.8849	High Similarity	NPC95679
0.8849	High Similarity	NPC110899
0.8849	High Similarity	NPC112068
0.8832	High Similarity	NPC129889
0.8832	High Similarity	NPC307006
0.8828	High Similarity	NPC125570
0.875	High Similarity	NPC142985
0.875	High Similarity	NPC195292
0.8733	High Similarity	NPC84935
0.8733	High Similarity	NPC190020
0.8733	High Similarity	NPC77679
0.8725	High Similarity	NPC79998
0.8725	High Similarity	NPC199926
0.8716	High Similarity	NPC473236
0.8707	High Similarity	NPC96501
0.8705	High Similarity	NPC208760
0.869	High Similarity	NPC138978
0.8686	High Similarity	NPC469480
0.8667	High Similarity	NPC150227
0.8658	High Similarity	NPC136757
0.8658	High Similarity	NPC287504
0.8658	High Similarity	NPC25127
0.8649	High Similarity	NPC477699
0.8643	High Similarity	NPC209229
0.8636	High Similarity	NPC49341
0.8633	High Similarity	NPC155098
0.8611	High Similarity	NPC239608
0.8611	High Similarity	NPC46161
0.8592	High Similarity	NPC147379
0.8571	High Similarity	NPC274613
0.8571	High Similarity	NPC668
0.8571	High Similarity	NPC474965
0.8571	High Similarity	NPC293757
0.8571	High Similarity	NPC113295
0.8571	High Similarity	NPC216223
0.8571	High Similarity	NPC174512
0.8571	High Similarity	NPC477695
0.8571	High Similarity	NPC145569
0.8562	High Similarity	NPC103201
0.8562	High Similarity	NPC473106
0.8552	High Similarity	NPC223185
0.8552	High Similarity	NPC210425
0.8552	High Similarity	NPC277426
0.8552	High Similarity	NPC280404
0.8552	High Similarity	NPC86373
0.8543	High Similarity	NPC469474
0.8543	High Similarity	NPC227062
0.8542	High Similarity	NPC299154
0.854	High Similarity	NPC48315
0.854	High Similarity	NPC153547
0.8533	High Similarity	NPC197188
0.8533	High Similarity	NPC43872
0.8533	High Similarity	NPC291510
0.8533	High Similarity	NPC116850
0.8533	High Similarity	NPC238672
0.8533	High Similarity	NPC144801
0.8531	High Similarity	NPC100675
0.8531	High Similarity	NPC50823
0.8529	High Similarity	NPC12022
0.8529	High Similarity	NPC20404
0.8529	High Similarity	NPC20287
0.8529	High Similarity	NPC293641
0.8523	High Similarity	NPC75695
0.8523	High Similarity	NPC151425
0.8523	High Similarity	NPC204350
0.8519	High Similarity	NPC280767
0.8511	High Similarity	NPC156892
0.8507	High Similarity	NPC165375
0.8507	High Similarity	NPC220598
0.8506	High Similarity	NPC76687
0.85	High Similarity	NPC237330
0.8497	Intermediate Similarity	NPC292415
0.8496	Intermediate Similarity	NPC194416
0.8496	Intermediate Similarity	NPC177291
0.8483	Intermediate Similarity	NPC469542
0.8483	Intermediate Similarity	NPC51106
0.8477	Intermediate Similarity	NPC38898
0.8477	Intermediate Similarity	NPC20541
0.8472	Intermediate Similarity	NPC31751
0.8472	Intermediate Similarity	NPC67650
0.8472	Intermediate Similarity	NPC253722
0.8472	Intermediate Similarity	NPC1704
0.8472	Intermediate Similarity	NPC253481
0.8467	Intermediate Similarity	NPC289968
0.8467	Intermediate Similarity	NPC109275
0.8467	Intermediate Similarity	NPC472912
0.8467	Intermediate Similarity	NPC167903
0.8467	Intermediate Similarity	NPC65591
0.8467	Intermediate Similarity	NPC260979
0.8467	Intermediate Similarity	NPC199773
0.8467	Intermediate Similarity	NPC178574
0.8467	Intermediate Similarity	NPC278308
0.8462	Intermediate Similarity	NPC471819
0.8456	Intermediate Similarity	NPC477700
0.8456	Intermediate Similarity	NPC472279
0.8456	Intermediate Similarity	NPC76451
0.8451	Intermediate Similarity	NPC135837
0.8446	Intermediate Similarity	NPC477698
0.8446	Intermediate Similarity	NPC194653
0.8446	Intermediate Similarity	NPC203747
0.8446	Intermediate Similarity	NPC80710
0.8446	Intermediate Similarity	NPC139364
0.8446	Intermediate Similarity	NPC254702
0.8442	Intermediate Similarity	NPC349525
0.844	Intermediate Similarity	NPC182496
0.844	Intermediate Similarity	NPC180905
0.844	Intermediate Similarity	NPC72796
0.844	Intermediate Similarity	NPC44245
0.844	Intermediate Similarity	NPC211386
0.844	Intermediate Similarity	NPC18646
0.8435	Intermediate Similarity	NPC208507
0.8435	Intermediate Similarity	NPC30720
0.8435	Intermediate Similarity	NPC472333
0.8429	Intermediate Similarity	NPC159418
0.8429	Intermediate Similarity	NPC1321
0.8429	Intermediate Similarity	NPC156124
0.8429	Intermediate Similarity	NPC288743
0.8429	Intermediate Similarity	NPC304929
0.8429	Intermediate Similarity	NPC283823
0.8425	Intermediate Similarity	NPC207732
0.8425	Intermediate Similarity	NPC469683
0.8421	Intermediate Similarity	NPC54928
0.8421	Intermediate Similarity	NPC165483
0.8417	Intermediate Similarity	NPC264145
0.8417	Intermediate Similarity	NPC474017
0.8414	Intermediate Similarity	NPC474385
0.8411	Intermediate Similarity	NPC469550
0.8403	Intermediate Similarity	NPC19158
0.84	Intermediate Similarity	NPC95498
0.84	Intermediate Similarity	NPC200773
0.84	Intermediate Similarity	NPC246566
0.84	Intermediate Similarity	NPC215921
0.84	Intermediate Similarity	NPC256406
0.84	Intermediate Similarity	NPC476434
0.84	Intermediate Similarity	NPC240768
0.84	Intermediate Similarity	NPC70016
0.84	Intermediate Similarity	NPC56184
0.8394	Intermediate Similarity	NPC127587
0.8392	Intermediate Similarity	NPC325625
0.8389	Intermediate Similarity	NPC473091
0.8389	Intermediate Similarity	NPC264550
0.8389	Intermediate Similarity	NPC69430
0.8389	Intermediate Similarity	NPC200060
0.8389	Intermediate Similarity	NPC333691
0.8389	Intermediate Similarity	NPC142876
0.8389	Intermediate Similarity	NPC195763
0.8389	Intermediate Similarity	NPC270160
0.8389	Intermediate Similarity	NPC237440
0.8389	Intermediate Similarity	NPC139293
0.8389	Intermediate Similarity	NPC264289
0.8389	Intermediate Similarity	NPC40290
0.8382	Intermediate Similarity	NPC58279
0.8382	Intermediate Similarity	NPC300326
0.8378	Intermediate Similarity	NPC125449
0.8378	Intermediate Similarity	NPC188074
0.8378	Intermediate Similarity	NPC210320
0.8377	Intermediate Similarity	NPC24627
0.8369	Intermediate Similarity	NPC5310
0.8369	Intermediate Similarity	NPC68779
0.8369	Intermediate Similarity	NPC300776
0.8369	Intermediate Similarity	NPC176814
0.8369	Intermediate Similarity	NPC4982
0.8367	Intermediate Similarity	NPC213482
0.8367	Intermediate Similarity	NPC474799
0.8367	Intermediate Similarity	NPC157133
0.8367	Intermediate Similarity	NPC472560
0.8367	Intermediate Similarity	NPC287275
0.8366	Intermediate Similarity	NPC469584
0.8366	Intermediate Similarity	NPC129684
0.8366	Intermediate Similarity	NPC108456
0.8366	Intermediate Similarity	NPC179732
0.8366	Intermediate Similarity	NPC222689
0.8366	Intermediate Similarity	NPC299520
0.8366	Intermediate Similarity	NPC35598
0.8357	Intermediate Similarity	NPC50763
0.8357	Intermediate Similarity	NPC111888
0.8356	Intermediate Similarity	NPC119663
0.8356	Intermediate Similarity	NPC472006
0.8356	Intermediate Similarity	NPC471417
0.8356	Intermediate Similarity	NPC287722
0.8356	Intermediate Similarity	NPC469615
0.8356	Intermediate Similarity	NPC254659
0.8355	Intermediate Similarity	NPC476642

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 NPC203351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	913
0.2-0.3	1943
0.3-0.4	2626
0.4-0.5	1741
0.5-0.6	994
0.6-0.7	516
0.7-0.8	133
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8429	Intermediate Similarity	NPD230	Phase 1
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD3027	Phase 3
0.8224	Intermediate Similarity	NPD1934	Approved
0.8105	Intermediate Similarity	NPD37	Approved
0.8077	Intermediate Similarity	NPD6234	Discontinued
0.8065	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3882	Suspended
0.8052	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2801	Approved
0.8038	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD7199	Phase 2
0.7949	Intermediate Similarity	NPD4965	Approved
0.7949	Intermediate Similarity	NPD4967	Phase 2
0.7949	Intermediate Similarity	NPD4966	Approved
0.7937	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6166	Phase 2
0.7933	Intermediate Similarity	NPD1511	Approved
0.7881	Intermediate Similarity	NPD2532	Approved
0.7881	Intermediate Similarity	NPD2534	Approved
0.7881	Intermediate Similarity	NPD2533	Approved
0.7872	Intermediate Similarity	NPD9494	Approved
0.7853	Intermediate Similarity	NPD7074	Phase 3
0.784	Intermediate Similarity	NPD7228	Approved
0.784	Intermediate Similarity	NPD3818	Discontinued
0.7832	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1512	Approved
0.7821	Intermediate Similarity	NPD1465	Phase 2
0.7815	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1608	Approved
0.777	Intermediate Similarity	NPD9269	Phase 2
0.7764	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1510	Phase 2
0.7744	Intermediate Similarity	NPD7472	Approved
0.7733	Intermediate Similarity	NPD4628	Phase 3
0.7724	Intermediate Similarity	NPD1240	Approved
0.7724	Intermediate Similarity	NPD1613	Approved
0.7724	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6799	Approved
0.7683	Intermediate Similarity	NPD5844	Phase 1
0.7673	Intermediate Similarity	NPD7075	Discontinued
0.7669	Intermediate Similarity	NPD228	Approved
0.7628	Intermediate Similarity	NPD4380	Phase 2
0.7628	Intermediate Similarity	NPD6599	Discontinued
0.7622	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1607	Approved
0.7603	Intermediate Similarity	NPD943	Approved
0.7595	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7819	Suspended
0.759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6797	Phase 2
0.7569	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6190	Approved
0.7554	Intermediate Similarity	NPD17	Approved
0.7551	Intermediate Similarity	NPD447	Suspended
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7533	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1549	Phase 2
0.7482	Intermediate Similarity	NPD9268	Approved
0.7469	Intermediate Similarity	NPD5494	Approved
0.7467	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD2935	Discontinued
0.7467	Intermediate Similarity	NPD6100	Approved
0.7465	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5353	Approved
0.7419	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1283	Approved
0.7412	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD9545	Approved
0.74	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7411	Suspended
0.7351	Intermediate Similarity	NPD1551	Phase 2
0.7337	Intermediate Similarity	NPD7685	Pre-registration
0.7337	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD5242	Approved
0.7329	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6355	Discontinued
0.731	Intermediate Similarity	NPD5647	Approved
0.7308	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3146	Approved
0.7299	Intermediate Similarity	NPD5283	Phase 1
0.7285	Intermediate Similarity	NPD7033	Discontinued
0.7284	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD6651	Approved
0.7267	Intermediate Similarity	NPD6653	Approved
0.7248	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3620	Phase 2
0.7248	Intermediate Similarity	NPD4060	Phase 1
0.7237	Intermediate Similarity	NPD2796	Approved
0.7222	Intermediate Similarity	NPD2982	Phase 2
0.7222	Intermediate Similarity	NPD2983	Phase 2
0.7222	Intermediate Similarity	NPD5402	Approved
0.7215	Intermediate Similarity	NPD5403	Approved
0.7211	Intermediate Similarity	NPD4908	Phase 1
0.7203	Intermediate Similarity	NPD422	Phase 1
0.7203	Intermediate Similarity	NPD1281	Approved
0.7203	Intermediate Similarity	NPD3705	Approved
0.7203	Intermediate Similarity	NPD1610	Phase 2
0.7192	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1778	Approved
0.7169	Intermediate Similarity	NPD5710	Approved
0.7169	Intermediate Similarity	NPD5711	Approved
0.7161	Intermediate Similarity	NPD8166	Discontinued
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2981	Phase 2
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7133	Intermediate Similarity	NPD826	Approved
0.7133	Intermediate Similarity	NPD825	Approved
0.7126	Intermediate Similarity	NPD3926	Phase 2
0.7124	Intermediate Similarity	NPD2438	Suspended
0.7124	Intermediate Similarity	NPD9570	Approved
0.7114	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7114	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1357	Approved
0.7108	Intermediate Similarity	NPD1247	Approved
0.7108	Intermediate Similarity	NPD6959	Discontinued
0.7103	Intermediate Similarity	NPD4749	Approved
0.7097	Intermediate Similarity	NPD2800	Approved
0.7097	Intermediate Similarity	NPD1243	Approved
0.7097	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5401	Approved
0.7089	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6002	Phase 3
0.7078	Intermediate Similarity	NPD6005	Phase 3
0.7078	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6004	Phase 3
0.7078	Intermediate Similarity	NPD7266	Discontinued
0.7078	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6233	Phase 2
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7066	Intermediate Similarity	NPD3787	Discontinued
0.7047	Intermediate Similarity	NPD7095	Approved
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6386	Approved
0.7037	Intermediate Similarity	NPD6385	Approved
0.7034	Intermediate Similarity	NPD9717	Approved
0.703	Intermediate Similarity	NPD3749	Approved
0.7025	Intermediate Similarity	NPD4357	Discontinued
0.7021	Intermediate Similarity	NPD9493	Approved
0.702	Intermediate Similarity	NPD2979	Phase 3
0.7017	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3021	Approved
0.7007	Intermediate Similarity	NPD2797	Approved
0.7007	Intermediate Similarity	NPD3022	Approved
0.7006	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD2219	Phase 1
0.7	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD920	Approved
0.7	Intermediate Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD6111	Discontinued
0.6987	Remote Similarity	NPD1652	Phase 2
0.6974	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5124	Phase 1
0.6972	Remote Similarity	NPD5536	Phase 2
0.6962	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD257	Approved
0.6959	Remote Similarity	NPD258	Approved
0.6957	Remote Similarity	NPD3686	Approved
0.6957	Remote Similarity	NPD3687	Approved
0.6954	Remote Similarity	NPD4062	Phase 3
0.695	Remote Similarity	NPD7157	Approved
0.6948	Remote Similarity	NPD2799	Discontinued
0.6948	Remote Similarity	NPD3748	Approved
0.6948	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4626	Approved
0.6934	Remote Similarity	NPD2684	Approved
0.6933	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1548	Phase 1
0.6918	Remote Similarity	NPD1481	Phase 2
0.6914	Remote Similarity	NPD4005	Discontinued
0.6914	Remote Similarity	NPD7458	Discontinued
0.6901	Remote Similarity	NPD3751	Discontinued
0.6897	Remote Similarity	NPD3847	Discontinued
0.6892	Remote Similarity	NPD1203	Approved
0.6887	Remote Similarity	NPD411	Approved
0.6887	Remote Similarity	NPD1296	Phase 2
0.6879	Remote Similarity	NPD5953	Discontinued
0.6879	Remote Similarity	NPD2654	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