NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.1
Volume:	250.009
LogP:	3.152
LogD:	3.167
LogS:	-2.585
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	2.756
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.68
MDCK Permeability:	2.244048664579168e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.117
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.542
30% Bioavailability (F30%):	0.511

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	97.8650894165039%
Volume Distribution (VD):	0.607
Pgp-substrate:	1.1531665325164795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.757
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.879
CYP2C19-substrate:	0.428
CYP2C9-inhibitor:	0.793
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.918
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.564
CYP3A4-substrate:	0.536

ADMET: Excretion

Clearance (CL):	13.975
Half-life (T1/2):	0.584

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.893
Carcinogencity:	0.281
Eye Corrosion:	0.029
Eye Irritation:	0.934
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC12221

Natural Product ID:	NPC12221
*Common Name:**	(S)-2-(1-Phenylallyl)Benzene-1,4-Diol
IUPAC Name:	2-[(1S)-1-phenylprop-2-enyl]benzene-1,4-diol
Synonyms:
Standard InCHIKey:	YWLDSNVXQNBZKU-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C15H14O2/c1-2-13(11-6-4-3-5-7-11)14-10-12(16)8-9-15(14)17/h2-10,13,16-17H,1H2/t13-/m0/s1
SMILES:	C=C[C@@H](c1ccccc1)c1cc(ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403074
PubChem CID:	24769835
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18154272]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22212722]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1830	Dalbergia sissoo	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
IC50	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	31600.0	nM	PMID[541312]

☑ 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 NPC12221 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	389
0.1-0.2	2040
0.2-0.3	5508
0.3-0.4	13216
0.4-0.5	5621
0.5-0.6	10104
0.6-0.7	4375
0.7-0.8	1140
0.8-0.85	204
0.85-0.9	83
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC233827
0.9394	High Similarity	NPC54765
0.93	High Similarity	NPC320439
0.9208	High Similarity	NPC95344
0.92	High Similarity	NPC67250
0.9192	High Similarity	NPC475580
0.9082	High Similarity	NPC48730
0.9082	High Similarity	NPC129373
0.9082	High Similarity	NPC248396
0.9072	High Similarity	NPC156313
0.9072	High Similarity	NPC152097
0.9062	High Similarity	NPC274678
0.9053	High Similarity	NPC29373
0.9053	High Similarity	NPC271440
0.9	High Similarity	NPC323810
0.898	High Similarity	NPC260775
0.8969	High Similarity	NPC312132
0.8969	High Similarity	NPC259512
0.8958	High Similarity	NPC76938
0.8958	High Similarity	NPC128062
0.8942	High Similarity	NPC266937
0.8942	High Similarity	NPC77772
0.8942	High Similarity	NPC470770
0.8911	High Similarity	NPC47284
0.89	High Similarity	NPC168393
0.89	High Similarity	NPC269212
0.89	High Similarity	NPC108497
0.8889	High Similarity	NPC130756
0.8889	High Similarity	NPC130103
0.8889	High Similarity	NPC70677
0.8889	High Similarity	NPC72729
0.8889	High Similarity	NPC12931
0.8878	High Similarity	NPC79241
0.8878	High Similarity	NPC6597
0.8878	High Similarity	NPC475078
0.8866	High Similarity	NPC32714
0.8857	High Similarity	NPC177962
0.8857	High Similarity	NPC62867
0.8824	High Similarity	NPC53740
0.8824	High Similarity	NPC155072
0.8812	High Similarity	NPC475225
0.8812	High Similarity	NPC288411
0.8812	High Similarity	NPC272029
0.8812	High Similarity	NPC102216
0.88	High Similarity	NPC477685
0.8776	High Similarity	NPC132271
0.8776	High Similarity	NPC292730
0.8776	High Similarity	NPC216520
0.8776	High Similarity	NPC82664
0.8763	High Similarity	NPC245187
0.8762	High Similarity	NPC54373
0.875	High Similarity	NPC45040
0.8725	High Similarity	NPC138942
0.8725	High Similarity	NPC239291
0.8713	High Similarity	NPC471228
0.8713	High Similarity	NPC235762
0.8713	High Similarity	NPC168829
0.87	High Similarity	NPC294741
0.87	High Similarity	NPC174911
0.8687	High Similarity	NPC88420
0.8687	High Similarity	NPC32674
0.866	High Similarity	NPC55903
0.8654	High Similarity	NPC169450
0.8646	High Similarity	NPC192
0.8641	High Similarity	NPC248904
0.8641	High Similarity	NPC469913
0.8632	High Similarity	NPC27974
0.8627	High Similarity	NPC238696
0.8617	High Similarity	NPC155393
0.8614	High Similarity	NPC100340
0.8614	High Similarity	NPC143659
0.8614	High Similarity	NPC80800
0.86	High Similarity	NPC33675
0.86	High Similarity	NPC299762
0.86	High Similarity	NPC92730
0.8586	High Similarity	NPC473388
0.8585	High Similarity	NPC224527
0.8571	High Similarity	NPC152415
0.8571	High Similarity	NPC151715
0.8571	High Similarity	NPC58865
0.8558	High Similarity	NPC66834
0.8557	High Similarity	NPC304541
0.8557	High Similarity	NPC306074
0.8557	High Similarity	NPC231150
0.8544	High Similarity	NPC117115
0.8532	High Similarity	NPC141001
0.8526	High Similarity	NPC307235
0.8526	High Similarity	NPC407
0.8519	High Similarity	NPC471534
0.85	High Similarity	NPC77492
0.85	High Similarity	NPC474073
0.85	High Similarity	NPC225464
0.8491	Intermediate Similarity	NPC132720
0.8491	Intermediate Similarity	NPC296683
0.8485	Intermediate Similarity	NPC8392
0.8485	Intermediate Similarity	NPC26244
0.8476	Intermediate Similarity	NPC262365
0.8476	Intermediate Similarity	NPC174981
0.8476	Intermediate Similarity	NPC11554
0.8476	Intermediate Similarity	NPC233835
0.8469	Intermediate Similarity	NPC3358
0.8469	Intermediate Similarity	NPC94139
0.8469	Intermediate Similarity	NPC210497
0.8469	Intermediate Similarity	NPC147284
0.8469	Intermediate Similarity	NPC162314
0.8469	Intermediate Similarity	NPC306884
0.8462	Intermediate Similarity	NPC271274
0.8454	Intermediate Similarity	NPC312304
0.8447	Intermediate Similarity	NPC93831
0.8447	Intermediate Similarity	NPC30506
0.8447	Intermediate Similarity	NPC471511
0.8447	Intermediate Similarity	NPC327811
0.8447	Intermediate Similarity	NPC241891
0.8447	Intermediate Similarity	NPC254965
0.8447	Intermediate Similarity	NPC130817
0.844	Intermediate Similarity	NPC232165
0.8431	Intermediate Similarity	NPC252105
0.8431	Intermediate Similarity	NPC51015
0.8411	Intermediate Similarity	NPC469912
0.8411	Intermediate Similarity	NPC95716
0.8411	Intermediate Similarity	NPC275627
0.8411	Intermediate Similarity	NPC151537
0.8396	Intermediate Similarity	NPC473524
0.8396	Intermediate Similarity	NPC228343
0.8396	Intermediate Similarity	NPC202647
0.8396	Intermediate Similarity	NPC33728
0.8396	Intermediate Similarity	NPC254833
0.8396	Intermediate Similarity	NPC314187
0.8396	Intermediate Similarity	NPC19808
0.8381	Intermediate Similarity	NPC233320
0.8381	Intermediate Similarity	NPC151477
0.8365	Intermediate Similarity	NPC292452
0.8365	Intermediate Similarity	NPC134829
0.8351	Intermediate Similarity	NPC258219
0.8333	Intermediate Similarity	NPC46940
0.8333	Intermediate Similarity	NPC302371
0.8318	Intermediate Similarity	NPC13482
0.8317	Intermediate Similarity	NPC291789
0.8316	Intermediate Similarity	NPC286904
0.8316	Intermediate Similarity	NPC150837
0.8304	Intermediate Similarity	NPC323074
0.8302	Intermediate Similarity	NPC279887
0.8302	Intermediate Similarity	NPC68260
0.83	Intermediate Similarity	NPC222146
0.8286	Intermediate Similarity	NPC310456
0.8286	Intermediate Similarity	NPC118286
0.8286	Intermediate Similarity	NPC470700
0.8286	Intermediate Similarity	NPC302681
0.8286	Intermediate Similarity	NPC39664
0.8286	Intermediate Similarity	NPC21594
0.8286	Intermediate Similarity	NPC39097
0.8286	Intermediate Similarity	NPC109691
0.8273	Intermediate Similarity	NPC84999
0.8273	Intermediate Similarity	NPC246760
0.8269	Intermediate Similarity	NPC119860
0.8257	Intermediate Similarity	NPC23804
0.8257	Intermediate Similarity	NPC715
0.8257	Intermediate Similarity	NPC261343
0.8247	Intermediate Similarity	NPC19680
0.8241	Intermediate Similarity	NPC308689
0.8241	Intermediate Similarity	NPC225679
0.8241	Intermediate Similarity	NPC476632
0.8241	Intermediate Similarity	NPC165770
0.8241	Intermediate Similarity	NPC4493
0.8235	Intermediate Similarity	NPC122005
0.8235	Intermediate Similarity	NPC78119
0.8235	Intermediate Similarity	NPC51333
0.8235	Intermediate Similarity	NPC252821
0.8235	Intermediate Similarity	NPC132078
0.8235	Intermediate Similarity	NPC216468
0.823	Intermediate Similarity	NPC318581
0.823	Intermediate Similarity	NPC325544
0.823	Intermediate Similarity	NPC477037
0.8224	Intermediate Similarity	NPC299568
0.8224	Intermediate Similarity	NPC282855
0.8224	Intermediate Similarity	NPC186385
0.8224	Intermediate Similarity	NPC26013
0.8224	Intermediate Similarity	NPC98392
0.8218	Intermediate Similarity	NPC202986
0.8208	Intermediate Similarity	NPC474352
0.8208	Intermediate Similarity	NPC54844
0.82	Intermediate Similarity	NPC316301
0.82	Intermediate Similarity	NPC27323
0.82	Intermediate Similarity	NPC289769
0.819	Intermediate Similarity	NPC474839
0.819	Intermediate Similarity	NPC246056
0.819	Intermediate Similarity	NPC471350
0.8182	Intermediate Similarity	NPC107240
0.8182	Intermediate Similarity	NPC204210
0.8182	Intermediate Similarity	NPC195922
0.8182	Intermediate Similarity	NPC249270
0.8182	Intermediate Similarity	NPC155908
0.8165	Intermediate Similarity	NPC43525
0.8165	Intermediate Similarity	NPC98372
0.8165	Intermediate Similarity	NPC250323
0.8165	Intermediate Similarity	NPC286222
0.8165	Intermediate Similarity	NPC228452
0.8165	Intermediate Similarity	NPC166995
0.8165	Intermediate Similarity	NPC228425
0.8163	Intermediate Similarity	NPC318325

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 NPC12221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	1049
0.2-0.3	1230
0.3-0.4	2953
0.4-0.5	1892
0.5-0.6	1153
0.6-0.7	407
0.7-0.8	65
0.8-0.85	10
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9278	High Similarity	NPD289	Clinical (unspecified phase)
0.8969	High Similarity	NPD288	Approved
0.8857	High Similarity	NPD7635	Approved
0.8788	High Similarity	NPD3020	Approved
0.8673	High Similarity	NPD844	Approved
0.8485	Intermediate Similarity	NPD2860	Approved
0.8485	Intermediate Similarity	NPD2859	Approved
0.8469	Intermediate Similarity	NPD845	Approved
0.8396	Intermediate Similarity	NPD3022	Approved
0.8396	Intermediate Similarity	NPD3021	Approved
0.8384	Intermediate Similarity	NPD2933	Approved
0.8384	Intermediate Similarity	NPD2934	Approved
0.8381	Intermediate Similarity	NPD2342	Discontinued
0.8224	Intermediate Similarity	NPD4750	Phase 3
0.82	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD1242	Phase 1
0.8108	Intermediate Similarity	NPD6671	Approved
0.8056	Intermediate Similarity	NPD1792	Phase 2
0.8018	Intermediate Similarity	NPD497	Approved
0.7944	Intermediate Similarity	NPD1445	Approved
0.7944	Intermediate Similarity	NPD1444	Approved
0.7944	Intermediate Similarity	NPD968	Approved
0.7941	Intermediate Similarity	NPD1809	Phase 2
0.7928	Intermediate Similarity	NPD495	Approved
0.7928	Intermediate Similarity	NPD496	Approved
0.7928	Intermediate Similarity	NPD498	Approved
0.7905	Intermediate Similarity	NPD846	Approved
0.7905	Intermediate Similarity	NPD940	Approved
0.7857	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD111	Approved
0.7833	Intermediate Similarity	NPD2861	Phase 2
0.766	Intermediate Similarity	NPD9088	Approved
0.7647	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD1201	Approved
0.7611	Intermediate Similarity	NPD2229	Approved
0.7611	Intermediate Similarity	NPD2228	Approved
0.7611	Intermediate Similarity	NPD2234	Approved
0.7586	Intermediate Similarity	NPD3091	Approved
0.7521	Intermediate Similarity	NPD4093	Discontinued
0.7479	Intermediate Similarity	NPD1610	Phase 2
0.7478	Intermediate Similarity	NPD709	Approved
0.7458	Intermediate Similarity	NPD2286	Discontinued
0.7458	Intermediate Similarity	NPD2932	Approved
0.7458	Intermediate Similarity	NPD3019	Approved
0.7458	Intermediate Similarity	NPD4059	Approved
0.7453	Intermediate Similarity	NPD9273	Approved
0.7436	Intermediate Similarity	NPD5304	Approved
0.7436	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5303	Approved
0.7417	Intermediate Similarity	NPD2233	Approved
0.7417	Intermediate Similarity	NPD2232	Approved
0.7417	Intermediate Similarity	NPD2230	Approved
0.7414	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD1470	Approved
0.7339	Intermediate Similarity	NPD9500	Approved
0.7333	Intermediate Similarity	NPD1611	Approved
0.7333	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3092	Approved
0.7315	Intermediate Similarity	NPD3028	Approved
0.7311	Intermediate Similarity	NPD4589	Approved
0.7311	Intermediate Similarity	NPD1751	Approved
0.7304	Intermediate Similarity	NPD1398	Phase 1
0.7304	Intermediate Similarity	NPD5283	Phase 1
0.7281	Intermediate Similarity	NPD228	Approved
0.7265	Intermediate Similarity	NPD7340	Approved
0.7241	Intermediate Similarity	NPD1793	Approved
0.7241	Intermediate Similarity	NPD9618	Approved
0.7241	Intermediate Similarity	NPD1791	Approved
0.7241	Intermediate Similarity	NPD9614	Approved
0.7236	Intermediate Similarity	NPD3094	Phase 2
0.7234	Intermediate Similarity	NPD9087	Approved
0.7217	Intermediate Similarity	NPD9379	Approved
0.7217	Intermediate Similarity	NPD9377	Approved
0.7213	Intermediate Similarity	NPD4749	Approved
0.72	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3095	Discontinued
0.7154	Intermediate Similarity	NPD6696	Suspended
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD7330	Discontinued
0.7131	Intermediate Similarity	NPD1608	Approved
0.713	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9610	Approved
0.7117	Intermediate Similarity	NPD9608	Approved
0.7109	Intermediate Similarity	NPD4060	Phase 1
0.7107	Intermediate Similarity	NPD3496	Discontinued
0.7107	Intermediate Similarity	NPD1983	Approved
0.7107	Intermediate Similarity	NPD1980	Approved
0.7107	Intermediate Similarity	NPD1981	Approved
0.7097	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1164	Approved
0.7063	Intermediate Similarity	NPD4908	Phase 1
0.7059	Intermediate Similarity	NPD9613	Approved
0.7059	Intermediate Similarity	NPD9616	Approved
0.7059	Intermediate Similarity	NPD9615	Approved
0.7049	Intermediate Similarity	NPD1535	Discovery
0.7043	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4626	Approved
0.7019	Intermediate Similarity	NPD9295	Approved
0.7016	Intermediate Similarity	NPD1283	Approved
0.701	Intermediate Similarity	NPD9294	Approved
0.7009	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD316	Approved
0.7	Intermediate Similarity	NPD1616	Discontinued
0.6992	Remote Similarity	NPD2231	Phase 2
0.6992	Remote Similarity	NPD2235	Phase 2
0.6992	Remote Similarity	NPD1481	Phase 2
0.6984	Remote Similarity	NPD5736	Approved
0.6977	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1613	Approved
0.697	Remote Similarity	NPD2935	Discontinued
0.696	Remote Similarity	NPD2797	Approved
0.6957	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD475	Phase 2
0.6935	Remote Similarity	NPD1755	Approved
0.693	Remote Similarity	NPD290	Approved
0.6905	Remote Similarity	NPD2194	Approved
0.6905	Remote Similarity	NPD2195	Approved
0.6905	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6584	Phase 3
0.6891	Remote Similarity	NPD6387	Discontinued
0.6885	Remote Similarity	NPD17	Approved
0.6885	Remote Similarity	NPD9381	Approved
0.6885	Remote Similarity	NPD2667	Approved
0.6885	Remote Similarity	NPD9384	Approved
0.6885	Remote Similarity	NPD2668	Approved
0.688	Remote Similarity	NPD5311	Approved
0.688	Remote Similarity	NPD5310	Approved
0.6875	Remote Similarity	NPD5155	Approved
0.6875	Remote Similarity	NPD5156	Approved
0.6875	Remote Similarity	NPD3027	Phase 3
0.687	Remote Similarity	NPD9266	Approved
0.687	Remote Similarity	NPD74	Approved
0.685	Remote Similarity	NPD3637	Approved
0.685	Remote Similarity	NPD3635	Approved
0.685	Remote Similarity	NPD3636	Approved
0.6846	Remote Similarity	NPD6346	Approved
0.6846	Remote Similarity	NPD943	Approved
0.6846	Remote Similarity	NPD2238	Phase 2
0.6842	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD9089	Approved
0.6829	Remote Similarity	NPD3026	Approved
0.6829	Remote Similarity	NPD3023	Approved
0.6825	Remote Similarity	NPD3055	Approved
0.6825	Remote Similarity	NPD3053	Approved
0.6822	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5451	Approved
0.6803	Remote Similarity	NPD5585	Approved
0.6803	Remote Similarity	NPD3025	Approved
0.6803	Remote Similarity	NPD1651	Approved
0.6803	Remote Similarity	NPD3024	Approved
0.68	Remote Similarity	NPD4659	Approved
0.68	Remote Similarity	NPD1669	Approved
0.6797	Remote Similarity	NPD3595	Approved
0.6797	Remote Similarity	NPD2605	Approved
0.6797	Remote Similarity	NPD2606	Approved
0.6797	Remote Similarity	NPD3594	Approved
0.6797	Remote Similarity	NPD600	Approved
0.6797	Remote Similarity	NPD596	Approved
0.6791	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4817	Approved
0.6786	Remote Similarity	NPD4818	Approved
0.6783	Remote Similarity	NPD9267	Approved
0.6783	Remote Similarity	NPD9264	Approved
0.6783	Remote Similarity	NPD9263	Approved
0.678	Remote Similarity	NPD1138	Approved
0.6774	Remote Similarity	NPD1281	Approved
0.6772	Remote Similarity	NPD2798	Approved
0.6772	Remote Similarity	NPD4624	Approved
0.6769	Remote Similarity	NPD6663	Approved
0.6767	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.675	Remote Similarity	NPD255	Approved
0.675	Remote Similarity	NPD256	Approved
0.6742	Remote Similarity	NPD4097	Suspended
0.6733	Remote Similarity	NPD9093	Approved
0.6726	Remote Similarity	NPD4658	Approved
0.6726	Remote Similarity	NPD4229	Approved
0.6726	Remote Similarity	NPD3682	Approved
0.6726	Remote Similarity	NPD4656	Approved
0.6726	Remote Similarity	NPD3680	Approved
0.6726	Remote Similarity	NPD4231	Approved
0.6724	Remote Similarity	NPD2684	Approved
0.6723	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1759	Phase 1
0.6721	Remote Similarity	NPD1182	Approved
0.672	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1840	Phase 2
0.6719	Remote Similarity	NPD1712	Approved
0.6695	Remote Similarity	NPD1139	Approved
0.6695	Remote Similarity	NPD1137	Approved
0.6694	Remote Similarity	NPD9493	Approved
0.6694	Remote Similarity	NPD7636	Approved
0.6693	Remote Similarity	NPD4104	Clinical (unspecified phase)

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