NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.1
Volume:	173.841
LogP:	3.304
LogD:	3.434
LogS:	-2.593
# Rotatable Bonds:	2
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	1.52
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.335
MDCK Permeability:	2.7168151063960977e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.401

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.587
Plasma Protein Binding (PPB):	81.57844543457031%
Volume Distribution (VD):	2.317
Pgp-substrate:	14.030134201049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.567
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.531
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.264
CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	15.42
Half-life (T1/2):	0.808

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.668
Carcinogencity:	0.336
Eye Corrosion:	0.937
Eye Irritation:	0.992
Respiratory Toxicity:	0.228

Download Data

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

Natural Product: NPC258219

Natural Product ID:	NPC258219
*Common Name:**	4-Isobutyl-Phenol
IUPAC Name:	4-(2-methylpropyl)phenol
Synonyms:	4-Isobutyl-Phenol
Standard InCHIKey:	GDEHXPCZWFXRKC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14O/c1-8(2)7-9-3-5-10(11)6-4-9/h3-6,8,11H,7H2,1-2H3
SMILES:	CC(Cc1ccc(cc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL108850
PubChem CID:	123212
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	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
Others	4

Activity Type	# Activity
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	302000.0	nM	PMID[491730]
NPT35	Others	n.a.		LogP	=	3.4	n.a.	PMID[491730]
NPT35	Others	n.a.		pKa	=	10.2	n.a.	PMID[491730]
NPT35	Others	n.a.		LogD	=	3.4	n.a.	PMID[491730]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Log 1/I50	=	3.52	1/M	PMID[491730]

☑ 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 NPC258219 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	247
0.1-0.2	2012
0.2-0.3	6247
0.3-0.4	12771
0.4-0.5	6900
0.5-0.6	9266
0.6-0.7	4015
0.7-0.8	922
0.8-0.85	203
0.85-0.9	63
0.9-0.95	38
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC304541
0.9765	High Similarity	NPC242240
0.9765	High Similarity	NPC123273
0.9765	High Similarity	NPC318325
0.9762	High Similarity	NPC23167
0.9647	High Similarity	NPC113460
0.9647	High Similarity	NPC25493
0.9643	High Similarity	NPC197783
0.9535	High Similarity	NPC280347
0.9535	High Similarity	NPC177420
0.9524	High Similarity	NPC248817
0.9524	High Similarity	NPC175313
0.9438	High Similarity	NPC8392
0.9425	High Similarity	NPC55561
0.9405	High Similarity	NPC265146
0.9405	High Similarity	NPC124436
0.9333	High Similarity	NPC473388
0.9326	High Similarity	NPC27323
0.9326	High Similarity	NPC316301
0.9318	High Similarity	NPC45040
0.9318	High Similarity	NPC155908
0.9318	High Similarity	NPC204210
0.9302	High Similarity	NPC407
0.9302	High Similarity	NPC307235
0.9302	High Similarity	NPC184169
0.9231	High Similarity	NPC77492
0.9222	High Similarity	NPC26244
0.9213	High Similarity	NPC138117
0.9213	High Similarity	NPC325292
0.9205	High Similarity	NPC300017
0.9195	High Similarity	NPC27974
0.9186	High Similarity	NPC155393
0.9111	High Similarity	NPC151715
0.9111	High Similarity	NPC128062
0.9101	High Similarity	NPC306074
0.9091	High Similarity	NPC70436
0.9091	High Similarity	NPC98772
0.907	High Similarity	NPC286904
0.9022	High Similarity	NPC225464
0.9011	High Similarity	NPC274678
0.9011	High Similarity	NPC313650
0.9	High Similarity	NPC55903
0.9	High Similarity	NPC147284
0.9	High Similarity	NPC306884
0.9	High Similarity	NPC162314
0.9	High Similarity	NPC210497
0.9	High Similarity	NPC3358
0.9	High Similarity	NPC94139
0.8989	High Similarity	NPC192
0.8977	High Similarity	NPC104216
0.8925	High Similarity	NPC252821
0.8925	High Similarity	NPC122005
0.8925	High Similarity	NPC92730
0.8925	High Similarity	NPC128723
0.8913	High Similarity	NPC132271
0.8913	High Similarity	NPC259512
0.8913	High Similarity	NPC82664
0.8913	High Similarity	NPC292730
0.8913	High Similarity	NPC216520
0.8913	High Similarity	NPC312132
0.8901	High Similarity	NPC152415
0.8889	High Similarity	NPC270547
0.8851	High Similarity	NPC150837
0.883	High Similarity	NPC225506
0.8817	High Similarity	NPC6597
0.8817	High Similarity	NPC260000
0.8817	High Similarity	NPC79241
0.8804	High Similarity	NPC144682
0.8791	High Similarity	NPC271440
0.8791	High Similarity	NPC181709
0.8778	High Similarity	NPC300478
0.8764	High Similarity	NPC19680
0.8723	High Similarity	NPC80027
0.8723	High Similarity	NPC132078
0.8723	High Similarity	NPC78119
0.8723	High Similarity	NPC51333
0.8723	High Similarity	NPC280869
0.8723	High Similarity	NPC216468
0.871	High Similarity	NPC202986
0.8696	High Similarity	NPC76938
0.8696	High Similarity	NPC245187
0.8696	High Similarity	NPC289769
0.8681	High Similarity	NPC231150
0.8632	High Similarity	NPC72729
0.8632	High Similarity	NPC213730
0.8632	High Similarity	NPC211885
0.8617	High Similarity	NPC32674
0.8617	High Similarity	NPC107619
0.8617	High Similarity	NPC474073
0.8617	High Similarity	NPC109955
0.8602	High Similarity	NPC222146
0.8602	High Similarity	NPC32714
0.8571	High Similarity	NPC271274
0.8557	High Similarity	NPC120719
0.8542	High Similarity	NPC91461
0.8542	High Similarity	NPC40258
0.8542	High Similarity	NPC7686
0.8526	High Similarity	NPC245561
0.8526	High Similarity	NPC299762
0.8526	High Similarity	NPC33675
0.8495	Intermediate Similarity	NPC81010
0.8495	Intermediate Similarity	NPC32977
0.8488	Intermediate Similarity	NPC133050
0.8485	Intermediate Similarity	NPC228737
0.8469	Intermediate Similarity	NPC239291
0.8469	Intermediate Similarity	NPC138942
0.8469	Intermediate Similarity	NPC303141
0.8469	Intermediate Similarity	NPC154899
0.8469	Intermediate Similarity	NPC233396
0.8454	Intermediate Similarity	NPC168829
0.8454	Intermediate Similarity	NPC235762
0.8454	Intermediate Similarity	NPC471228
0.8454	Intermediate Similarity	NPC196479
0.8454	Intermediate Similarity	NPC470202
0.8454	Intermediate Similarity	NPC135784
0.8438	Intermediate Similarity	NPC289381
0.8438	Intermediate Similarity	NPC129373
0.8438	Intermediate Similarity	NPC174911
0.8438	Intermediate Similarity	NPC52472
0.8438	Intermediate Similarity	NPC248396
0.8438	Intermediate Similarity	NPC48730
0.8438	Intermediate Similarity	NPC155847
0.8421	Intermediate Similarity	NPC152097
0.8404	Intermediate Similarity	NPC286006
0.8404	Intermediate Similarity	NPC107522
0.84	Intermediate Similarity	NPC11554
0.8387	Intermediate Similarity	NPC29373
0.8384	Intermediate Similarity	NPC135464
0.8384	Intermediate Similarity	NPC477814
0.8384	Intermediate Similarity	NPC113457
0.8384	Intermediate Similarity	NPC92623
0.8384	Intermediate Similarity	NPC21594
0.8384	Intermediate Similarity	NPC248904
0.837	Intermediate Similarity	NPC151764
0.837	Intermediate Similarity	NPC47950
0.837	Intermediate Similarity	NPC312304
0.8367	Intermediate Similarity	NPC475580
0.8367	Intermediate Similarity	NPC254965
0.8367	Intermediate Similarity	NPC8931
0.8367	Intermediate Similarity	NPC471511
0.8367	Intermediate Similarity	NPC327811
0.8367	Intermediate Similarity	NPC288411
0.8367	Intermediate Similarity	NPC30506
0.8367	Intermediate Similarity	NPC475225
0.8367	Intermediate Similarity	NPC119860
0.8367	Intermediate Similarity	NPC120693
0.8367	Intermediate Similarity	NPC261573
0.8351	Intermediate Similarity	NPC110764
0.8351	Intermediate Similarity	NPC472585
0.8351	Intermediate Similarity	NPC252105
0.8351	Intermediate Similarity	NPC101025
0.8351	Intermediate Similarity	NPC471578
0.8351	Intermediate Similarity	NPC12221
0.8351	Intermediate Similarity	NPC51015
0.8333	Intermediate Similarity	NPC100870
0.8333	Intermediate Similarity	NPC171843
0.8333	Intermediate Similarity	NPC125732
0.8333	Intermediate Similarity	NPC260775
0.8317	Intermediate Similarity	NPC254833
0.8317	Intermediate Similarity	NPC58865
0.8317	Intermediate Similarity	NPC228343
0.83	Intermediate Similarity	NPC151477
0.8283	Intermediate Similarity	NPC243677
0.8283	Intermediate Similarity	NPC474839
0.828	Intermediate Similarity	NPC321956
0.8265	Intermediate Similarity	NPC302219
0.8265	Intermediate Similarity	NPC71002
0.8265	Intermediate Similarity	NPC242342
0.8265	Intermediate Similarity	NPC94351
0.8265	Intermediate Similarity	NPC313030
0.8265	Intermediate Similarity	NPC249828
0.8265	Intermediate Similarity	NPC62351
0.8265	Intermediate Similarity	NPC108497
0.8265	Intermediate Similarity	NPC146798
0.8265	Intermediate Similarity	NPC53051
0.8265	Intermediate Similarity	NPC85479
0.8265	Intermediate Similarity	NPC178902
0.8265	Intermediate Similarity	NPC24404
0.8265	Intermediate Similarity	NPC106396
0.8265	Intermediate Similarity	NPC168303
0.8265	Intermediate Similarity	NPC222522
0.8247	Intermediate Similarity	NPC130756
0.8247	Intermediate Similarity	NPC294741
0.8247	Intermediate Similarity	NPC12931
0.8247	Intermediate Similarity	NPC10588
0.8247	Intermediate Similarity	NPC166761
0.8247	Intermediate Similarity	NPC253746
0.8247	Intermediate Similarity	NPC70677
0.8235	Intermediate Similarity	NPC296683
0.8235	Intermediate Similarity	NPC13482
0.8235	Intermediate Similarity	NPC474149
0.8229	Intermediate Similarity	NPC201967
0.8229	Intermediate Similarity	NPC475078
0.8229	Intermediate Similarity	NPC156313
0.8218	Intermediate Similarity	NPC61885
0.8218	Intermediate Similarity	NPC201959
0.8218	Intermediate Similarity	NPC63698
0.8218	Intermediate Similarity	NPC317305
0.8218	Intermediate Similarity	NPC75440
0.8211	Intermediate Similarity	NPC246679

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 NPC258219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	1082
0.2-0.3	1316
0.3-0.4	2908
0.4-0.5	1910
0.5-0.6	1115
0.6-0.7	443
0.7-0.8	73
0.8-0.85	9
0.85-0.9	4
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9405	High Similarity	NPD111	Approved
0.9326	High Similarity	NPD1432	Clinical (unspecified phase)
0.9222	High Similarity	NPD2859	Approved
0.9222	High Similarity	NPD2860	Approved
0.913	High Similarity	NPD3020	Approved
0.9111	High Similarity	NPD2933	Approved
0.9111	High Similarity	NPD2934	Approved
0.9	High Similarity	NPD845	Approved
0.8913	High Similarity	NPD288	Approved
0.8804	High Similarity	NPD844	Approved
0.8804	High Similarity	NPD1809	Phase 2
0.8737	High Similarity	NPD846	Approved
0.8737	High Similarity	NPD940	Approved
0.8438	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD9610	Approved
0.8367	Intermediate Similarity	NPD9608	Approved
0.8317	Intermediate Similarity	NPD3022	Approved
0.8317	Intermediate Similarity	NPD3021	Approved
0.82	Intermediate Similarity	NPD1445	Approved
0.82	Intermediate Similarity	NPD1444	Approved
0.8095	Intermediate Similarity	NPD9087	Approved
0.8061	Intermediate Similarity	NPD1242	Phase 1
0.8	Intermediate Similarity	NPD2234	Approved
0.8	Intermediate Similarity	NPD2228	Approved
0.8	Intermediate Similarity	NPD2229	Approved
0.7961	Intermediate Similarity	NPD1792	Phase 2
0.7879	Intermediate Similarity	NPD3028	Approved
0.7816	Intermediate Similarity	NPD9294	Approved
0.781	Intermediate Similarity	NPD228	Approved
0.7788	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4750	Phase 3
0.7727	Intermediate Similarity	NPD9088	Approved
0.7723	Intermediate Similarity	NPD9500	Approved
0.7692	Intermediate Similarity	NPD2684	Approved
0.7685	Intermediate Similarity	NPD255	Approved
0.7685	Intermediate Similarity	NPD256	Approved
0.7677	Intermediate Similarity	NPD9273	Approved
0.7642	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5303	Approved
0.7636	Intermediate Similarity	NPD5304	Approved
0.7636	Intermediate Similarity	NPD3091	Approved
0.7596	Intermediate Similarity	NPD2342	Discontinued
0.7593	Intermediate Similarity	NPD475	Phase 2
0.757	Intermediate Similarity	NPD9379	Approved
0.757	Intermediate Similarity	NPD7635	Approved
0.757	Intermediate Similarity	NPD9377	Approved
0.7568	Intermediate Similarity	NPD4093	Discontinued
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD1751	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4059	Approved
0.7431	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1791	Approved
0.7431	Intermediate Similarity	NPD1793	Approved
0.7429	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD821	Approved
0.7407	Intermediate Similarity	NPD7843	Approved
0.7391	Intermediate Similarity	NPD9089	Approved
0.7387	Intermediate Similarity	NPD317	Approved
0.7387	Intermediate Similarity	NPD318	Approved
0.7387	Intermediate Similarity	NPD856	Approved
0.7387	Intermediate Similarity	NPD16	Approved
0.7368	Intermediate Similarity	NPD3092	Approved
0.7364	Intermediate Similarity	NPD6671	Approved
0.7345	Intermediate Similarity	NPD4589	Approved
0.7297	Intermediate Similarity	NPD9568	Approved
0.729	Intermediate Similarity	NPD5451	Approved
0.7283	Intermediate Similarity	NPD9093	Approved
0.7273	Intermediate Similarity	NPD9614	Approved
0.7273	Intermediate Similarity	NPD9618	Approved
0.7264	Intermediate Similarity	NPD290	Approved
0.7241	Intermediate Similarity	NPD4659	Approved
0.7241	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1610	Phase 2
0.7216	Intermediate Similarity	NPD9295	Approved
0.7207	Intermediate Similarity	NPD7157	Approved
0.7193	Intermediate Similarity	NPD2668	Approved
0.7193	Intermediate Similarity	NPD3095	Discontinued
0.7193	Intermediate Similarity	NPD2286	Discontinued
0.7193	Intermediate Similarity	NPD2667	Approved
0.7182	Intermediate Similarity	NPD5283	Phase 1
0.717	Intermediate Similarity	NPD3134	Approved
0.7168	Intermediate Similarity	NPD9545	Approved
0.7168	Intermediate Similarity	NPD1548	Phase 1
0.7158	Intermediate Similarity	NPD9073	Approved
0.7119	Intermediate Similarity	NPD3094	Phase 2
0.7115	Intermediate Similarity	NPD4818	Approved
0.7115	Intermediate Similarity	NPD4817	Approved
0.7105	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6583	Phase 3
0.7094	Intermediate Similarity	NPD6582	Phase 2
0.7091	Intermediate Similarity	NPD5535	Approved
0.708	Intermediate Similarity	NPD9613	Approved
0.708	Intermediate Similarity	NPD9616	Approved
0.708	Intermediate Similarity	NPD9615	Approved
0.7069	Intermediate Similarity	NPD422	Phase 1
0.7069	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2195	Approved
0.7059	Intermediate Similarity	NPD2194	Approved
0.7048	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9381	Approved
0.7043	Intermediate Similarity	NPD4626	Approved
0.7043	Intermediate Similarity	NPD9384	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7019	Intermediate Similarity	NPD1616	Discontinued
0.7018	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD316	Approved
0.7009	Intermediate Similarity	NPD2561	Approved
0.7009	Intermediate Similarity	NPD2562	Approved
0.7	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3637	Approved
0.7	Intermediate Similarity	NPD3635	Approved
0.7	Intermediate Similarity	NPD3636	Approved
0.6991	Remote Similarity	NPD9493	Approved
0.6991	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.699	Remote Similarity	NPD9609	Approved
0.699	Remote Similarity	NPD9612	Approved
0.699	Remote Similarity	NPD9611	Approved
0.6983	Remote Similarity	NPD3847	Discontinued
0.6983	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3421	Phase 3
0.6983	Remote Similarity	NPD3143	Discontinued
0.6975	Remote Similarity	NPD1131	Approved
0.6975	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1134	Approved
0.6975	Remote Similarity	NPD1129	Approved
0.6975	Remote Similarity	NPD1135	Approved
0.6975	Remote Similarity	NPD1133	Approved
0.6975	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4103	Phase 2
0.6949	Remote Similarity	NPD3685	Discontinued
0.6949	Remote Similarity	NPD9622	Approved
0.6944	Remote Similarity	NPD1358	Approved
0.6944	Remote Similarity	NPD9267	Approved
0.6944	Remote Similarity	NPD9264	Approved
0.6944	Remote Similarity	NPD9263	Approved
0.6942	Remote Similarity	NPD2606	Approved
0.6942	Remote Similarity	NPD2605	Approved
0.6942	Remote Similarity	NPD4908	Phase 1
0.6939	Remote Similarity	NPD1101	Approved
0.6939	Remote Similarity	NPD9094	Approved
0.6937	Remote Similarity	NPD1138	Approved
0.6923	Remote Similarity	NPD1535	Discovery
0.6917	Remote Similarity	NPD6584	Phase 3
0.6917	Remote Similarity	NPD257	Approved
0.6917	Remote Similarity	NPD258	Approved
0.6891	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1283	Approved
0.6887	Remote Similarity	NPD4229	Approved
0.6887	Remote Similarity	NPD3680	Approved
0.6887	Remote Similarity	NPD3682	Approved
0.6887	Remote Similarity	NPD3683	Approved
0.6887	Remote Similarity	NPD4231	Approved
0.6887	Remote Similarity	NPD3681	Approved
0.6885	Remote Similarity	NPD5156	Approved
0.6885	Remote Similarity	NPD5155	Approved
0.6875	Remote Similarity	NPD1241	Discontinued
0.687	Remote Similarity	NPD7330	Discontinued
0.687	Remote Similarity	NPD1759	Phase 1
0.6869	Remote Similarity	NPD800	Approved
0.6864	Remote Similarity	NPD2232	Approved
0.6864	Remote Similarity	NPD2230	Approved
0.6864	Remote Similarity	NPD1481	Phase 2
0.6864	Remote Similarity	NPD3070	Discontinued
0.6864	Remote Similarity	NPD2233	Approved
0.6863	Remote Similarity	NPD9296	Approved
0.686	Remote Similarity	NPD2861	Phase 2
0.6847	Remote Similarity	NPD1139	Approved
0.6847	Remote Similarity	NPD1137	Approved
0.6842	Remote Similarity	NPD3596	Phase 2
0.6842	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3023	Approved
0.6838	Remote Similarity	NPD3026	Approved
0.6833	Remote Similarity	NPD3053	Approved
0.6833	Remote Similarity	NPD1164	Approved
0.6833	Remote Similarity	NPD3055	Approved
0.6833	Remote Similarity	NPD987	Approved
0.6829	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD9495	Approved
0.6822	Remote Similarity	NPD9244	Approved
0.6814	Remote Similarity	NPD497	Approved
0.681	Remote Similarity	NPD3024	Approved
0.681	Remote Similarity	NPD3025	Approved
0.681	Remote Similarity	NPD1357	Approved
0.6807	Remote Similarity	NPD4749	Approved
0.6807	Remote Similarity	NPD1755	Approved
0.6807	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3595	Approved
0.6803	Remote Similarity	NPD3594	Approved
0.68	Remote Similarity	NPD1086	Approved
0.68	Remote Similarity	NPD1090	Approved
0.68	Remote Similarity	NPD1089	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