NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	200.08
Volume:	218.053
LogP:	2.828
LogD:	2.891
LogS:	-2.282
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	1.639
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.62
MDCK Permeability:	2.180888805014547e-05
Pgp-inhibitor:	0.104
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.304

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	96.36385345458984%
Volume Distribution (VD):	0.77
Pgp-substrate:	3.811077356338501%

ADMET: Metabolism

CYP1A2-inhibitor:	0.705
CYP1A2-substrate:	0.274
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.668
CYP2C9-substrate:	0.857
CYP2D6-inhibitor:	0.904
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	16.439
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.34
AMES Toxicity:	0.368
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.904
Carcinogencity:	0.464
Eye Corrosion:	0.291
Eye Irritation:	0.986
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC128062

Natural Product ID:	NPC128062
*Common Name:**	2-[(4-Hydroxyphenyl)Methyl]Phenol
IUPAC Name:	2-[(4-hydroxyphenyl)methyl]phenol
Synonyms:
Standard InCHIKey:	LVLNPXCISNPHLE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H12O2/c14-12-7-5-10(6-8-12)9-11-3-1-2-4-13(11)15/h1-8,14-15H,9H2
SMILES:	Oc1ccc(cc1)Cc1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3187039
PubChem CID:	75576
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
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2494	Xanthium strumarium	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
Potency	33

Activity Type	# Activity
Individual Protein	6
Others	27

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	19742.1	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	61877.3	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	15486.4	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	24633.8	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	8818.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	62430	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4897.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9806.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6113.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	69427.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	11101.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24544.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	11003.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61877.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10963.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43805.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55640.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19496.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	111	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1949.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24633.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	39042	nM	PubChem BioAssay data set

☑ 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 NPC128062 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	439
0.1-0.2	2413
0.2-0.3	7922
0.3-0.4	11387
0.4-0.5	5554
0.5-0.6	9277
0.6-0.7	4392
0.7-0.8	1002
0.8-0.85	205
0.85-0.9	82
0.9-0.95	20
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC45040
0.9556	High Similarity	NPC151715
0.9451	High Similarity	NPC26244
0.9451	High Similarity	NPC274678
0.9444	High Similarity	NPC271440
0.9348	High Similarity	NPC473388
0.9263	High Similarity	NPC168829
0.9205	High Similarity	NPC155393
0.9167	High Similarity	NPC288411
0.9167	High Similarity	NPC119860
0.9149	High Similarity	NPC92730
0.9149	High Similarity	NPC51333
0.9149	High Similarity	NPC132078
0.9149	High Similarity	NPC216468
0.9149	High Similarity	NPC78119
0.914	High Similarity	NPC82664
0.914	High Similarity	NPC292730
0.914	High Similarity	NPC216520
0.914	High Similarity	NPC132271
0.9121	High Similarity	NPC204210
0.9111	High Similarity	NPC123273
0.9111	High Similarity	NPC258219
0.9111	High Similarity	NPC318325
0.9111	High Similarity	NPC242240
0.9101	High Similarity	NPC23167
0.9101	High Similarity	NPC307235
0.9101	High Similarity	NPC407
0.9091	High Similarity	NPC175313
0.9072	High Similarity	NPC474839
0.9072	High Similarity	NPC138942
0.9053	High Similarity	NPC213730
0.9043	High Similarity	NPC225464
0.9032	High Similarity	NPC8392
0.9011	High Similarity	NPC300017
0.9	High Similarity	NPC113460
0.9	High Similarity	NPC25493
0.8989	High Similarity	NPC197783
0.898	High Similarity	NPC248904
0.898	High Similarity	NPC54765
0.8977	High Similarity	NPC265146
0.8958	High Similarity	NPC91461
0.8958	High Similarity	NPC40258
0.8958	High Similarity	NPC7686
0.8958	High Similarity	NPC12221
0.8947	High Similarity	NPC128723
0.8925	High Similarity	NPC76938
0.8913	High Similarity	NPC304541
0.8913	High Similarity	NPC306074
0.8901	High Similarity	NPC177420
0.8901	High Similarity	NPC70436
0.8901	High Similarity	NPC280347
0.8876	High Similarity	NPC248817
0.8876	High Similarity	NPC286904
0.8866	High Similarity	NPC135784
0.8842	High Similarity	NPC32674
0.8842	High Similarity	NPC156313
0.8842	High Similarity	NPC77492
0.883	High Similarity	NPC32714
0.8817	High Similarity	NPC325292
0.8817	High Similarity	NPC138117
0.8804	High Similarity	NPC55561
0.88	High Similarity	NPC95344
0.88	High Similarity	NPC61885
0.88	High Similarity	NPC262365
0.88	High Similarity	NPC63698
0.8791	High Similarity	NPC104216
0.8788	High Similarity	NPC271274
0.8776	High Similarity	NPC120693
0.8776	High Similarity	NPC8931
0.8776	High Similarity	NPC102216
0.8776	High Similarity	NPC30506
0.8776	High Similarity	NPC471511
0.8776	High Similarity	NPC261573
0.8764	High Similarity	NPC124436
0.875	High Similarity	NPC80027
0.875	High Similarity	NPC252821
0.875	High Similarity	NPC122005
0.8723	High Similarity	NPC316301
0.8723	High Similarity	NPC152415
0.8723	High Similarity	NPC27323
0.871	High Similarity	NPC155908
0.8687	High Similarity	NPC219286
0.8687	High Similarity	NPC292452
0.8687	High Similarity	NPC233396
0.8687	High Similarity	NPC99557
0.8687	High Similarity	NPC154899
0.8687	High Similarity	NPC239291
0.8681	High Similarity	NPC184169
0.8673	High Similarity	NPC470202
0.8673	High Similarity	NPC168393
0.8673	High Similarity	NPC233827
0.866	High Similarity	NPC294741
0.866	High Similarity	NPC225506
0.8646	High Similarity	NPC201967
0.8632	High Similarity	NPC313650
0.8632	High Similarity	NPC144682
0.8627	High Similarity	NPC296683
0.8627	High Similarity	NPC475018
0.8627	High Similarity	NPC44732
0.8614	High Similarity	NPC233835
0.8602	High Similarity	NPC192
0.8602	High Similarity	NPC300478
0.8602	High Similarity	NPC47950
0.86	High Similarity	NPC188677
0.86	High Similarity	NPC135464
0.86	High Similarity	NPC113457
0.86	High Similarity	NPC92623
0.8587	High Similarity	NPC27974
0.8586	High Similarity	NPC327811
0.8586	High Similarity	NPC254965
0.8571	High Similarity	NPC51015
0.8571	High Similarity	NPC100340
0.8571	High Similarity	NPC143659
0.8557	High Similarity	NPC130193
0.8557	High Similarity	NPC275104
0.8544	High Similarity	NPC308689
0.8544	High Similarity	NPC225679
0.8544	High Similarity	NPC476632
0.8544	High Similarity	NPC95716
0.8544	High Similarity	NPC165770
0.8544	High Similarity	NPC4493
0.8542	High Similarity	NPC312132
0.8542	High Similarity	NPC259512
0.8529	High Similarity	NPC58865
0.8529	High Similarity	NPC314187
0.8529	High Similarity	NPC202647
0.8526	High Similarity	NPC245187
0.8526	High Similarity	NPC289769
0.8511	High Similarity	NPC270547
0.8511	High Similarity	NPC231150
0.85	High Similarity	NPC303141
0.8495	Intermediate Similarity	NPC98772
0.8469	Intermediate Similarity	NPC248573
0.8469	Intermediate Similarity	NPC72729
0.8469	Intermediate Similarity	NPC248396
0.8469	Intermediate Similarity	NPC275053
0.8469	Intermediate Similarity	NPC48730
0.8469	Intermediate Similarity	NPC129373
0.8469	Intermediate Similarity	NPC161571
0.8469	Intermediate Similarity	NPC223393
0.8469	Intermediate Similarity	NPC174911
0.8462	Intermediate Similarity	NPC286222
0.8462	Intermediate Similarity	NPC43525
0.8462	Intermediate Similarity	NPC46940
0.8462	Intermediate Similarity	NPC228988
0.8462	Intermediate Similarity	NPC166995
0.8454	Intermediate Similarity	NPC260000
0.8454	Intermediate Similarity	NPC109955
0.8454	Intermediate Similarity	NPC79241
0.8454	Intermediate Similarity	NPC6597
0.8454	Intermediate Similarity	NPC152097
0.8454	Intermediate Similarity	NPC107619
0.8438	Intermediate Similarity	NPC246679
0.8431	Intermediate Similarity	NPC471495
0.8431	Intermediate Similarity	NPC174981
0.8431	Intermediate Similarity	NPC75440
0.8431	Intermediate Similarity	NPC11554
0.8421	Intermediate Similarity	NPC147284
0.8421	Intermediate Similarity	NPC210497
0.8421	Intermediate Similarity	NPC55903
0.8421	Intermediate Similarity	NPC29373
0.8421	Intermediate Similarity	NPC162314
0.8421	Intermediate Similarity	NPC181709
0.8421	Intermediate Similarity	NPC306884
0.8421	Intermediate Similarity	NPC3358
0.8421	Intermediate Similarity	NPC94139
0.8416	Intermediate Similarity	NPC69332
0.8416	Intermediate Similarity	NPC70843
0.8416	Intermediate Similarity	NPC67250
0.8416	Intermediate Similarity	NPC95178
0.8416	Intermediate Similarity	NPC29989
0.84	Intermediate Similarity	NPC241891
0.84	Intermediate Similarity	NPC238696
0.84	Intermediate Similarity	NPC323810
0.8381	Intermediate Similarity	NPC141003
0.8381	Intermediate Similarity	NPC35344
0.8381	Intermediate Similarity	NPC117846
0.8367	Intermediate Similarity	NPC33675
0.8367	Intermediate Similarity	NPC280869
0.8367	Intermediate Similarity	NPC299762
0.8367	Intermediate Similarity	NPC260775
0.8367	Intermediate Similarity	NPC245561
0.8365	Intermediate Similarity	NPC151537
0.8351	Intermediate Similarity	NPC202986
0.8351	Intermediate Similarity	NPC283711
0.835	Intermediate Similarity	NPC33728
0.835	Intermediate Similarity	NPC88141
0.835	Intermediate Similarity	NPC306045
0.835	Intermediate Similarity	NPC62258
0.835	Intermediate Similarity	NPC473372
0.835	Intermediate Similarity	NPC254833
0.835	Intermediate Similarity	NPC265211
0.835	Intermediate Similarity	NPC228343
0.835	Intermediate Similarity	NPC55617
0.835	Intermediate Similarity	NPC19808
0.8333	Intermediate Similarity	NPC81010
0.8333	Intermediate Similarity	NPC151477
0.8333	Intermediate Similarity	NPC228737
0.8333	Intermediate Similarity	NPC141523
0.8333	Intermediate Similarity	NPC320439

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 NPC128062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	1066
0.2-0.3	1278
0.3-0.4	2888
0.4-0.5	1895
0.5-0.6	1077
0.6-0.7	426
0.7-0.8	73
0.8-0.85	12
0.85-0.9	2
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9451	High Similarity	NPD2860	Approved
0.9451	High Similarity	NPD2859	Approved
0.9341	High Similarity	NPD2934	Approved
0.9341	High Similarity	NPD2933	Approved
0.9149	High Similarity	NPD3020	Approved
0.8764	High Similarity	NPD111	Approved
0.8763	High Similarity	NPD940	Approved
0.8763	High Similarity	NPD846	Approved
0.8723	High Similarity	NPD1432	Clinical (unspecified phase)
0.8632	High Similarity	NPD1809	Phase 2
0.8632	High Similarity	NPD844	Approved
0.8617	High Similarity	NPD845	Approved
0.8542	High Similarity	NPD288	Approved
0.8469	Intermediate Similarity	NPD1242	Phase 1
0.8469	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.835	Intermediate Similarity	NPD3022	Approved
0.835	Intermediate Similarity	NPD3021	Approved
0.8155	Intermediate Similarity	NPD2342	Discontinued
0.81	Intermediate Similarity	NPD3028	Approved
0.7963	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7635	Approved
0.79	Intermediate Similarity	NPD9273	Approved
0.7885	Intermediate Similarity	NPD968	Approved
0.787	Intermediate Similarity	NPD2228	Approved
0.787	Intermediate Similarity	NPD2229	Approved
0.787	Intermediate Similarity	NPD2234	Approved
0.7864	Intermediate Similarity	NPD9610	Approved
0.7864	Intermediate Similarity	NPD9608	Approved
0.7838	Intermediate Similarity	NPD5304	Approved
0.7838	Intermediate Similarity	NPD1548	Phase 1
0.7838	Intermediate Similarity	NPD5303	Approved
0.783	Intermediate Similarity	NPD4750	Phase 3
0.7727	Intermediate Similarity	NPD9087	Approved
0.7719	Intermediate Similarity	NPD1610	Phase 2
0.7699	Intermediate Similarity	NPD4589	Approved
0.7685	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1792	Phase 2
0.7586	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD9088	Approved
0.7568	Intermediate Similarity	NPD6671	Approved
0.7547	Intermediate Similarity	NPD1445	Approved
0.7547	Intermediate Similarity	NPD1444	Approved
0.7545	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2286	Discontinued
0.7544	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD228	Approved
0.7522	Intermediate Similarity	NPD3091	Approved
0.75	Intermediate Similarity	NPD5451	Approved
0.7473	Intermediate Similarity	NPD9294	Approved
0.7458	Intermediate Similarity	NPD1164	Approved
0.7456	Intermediate Similarity	NPD4093	Discontinued
0.7455	Intermediate Similarity	NPD9379	Approved
0.7455	Intermediate Similarity	NPD9377	Approved
0.7414	Intermediate Similarity	NPD1201	Approved
0.7411	Intermediate Similarity	NPD255	Approved
0.7411	Intermediate Similarity	NPD256	Approved
0.7407	Intermediate Similarity	NPD2684	Approved
0.7391	Intermediate Similarity	NPD2932	Approved
0.7391	Intermediate Similarity	NPD4059	Approved
0.7391	Intermediate Similarity	NPD3019	Approved
0.7368	Intermediate Similarity	NPD7330	Discontinued
0.7345	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2861	Phase 2
0.7321	Intermediate Similarity	NPD497	Approved
0.7315	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD290	Approved
0.7297	Intermediate Similarity	NPD5535	Approved
0.7288	Intermediate Similarity	NPD6583	Phase 3
0.7288	Intermediate Similarity	NPD4659	Approved
0.7288	Intermediate Similarity	NPD6582	Phase 2
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD1535	Discovery
0.7265	Intermediate Similarity	NPD422	Phase 1
0.7265	Intermediate Similarity	NPD3092	Approved
0.7264	Intermediate Similarity	NPD9500	Approved
0.7263	Intermediate Similarity	NPD9089	Approved
0.7257	Intermediate Similarity	NPD709	Approved
0.7248	Intermediate Similarity	NPD9266	Approved
0.7248	Intermediate Similarity	NPD74	Approved
0.7241	Intermediate Similarity	NPD1751	Approved
0.7232	Intermediate Similarity	NPD496	Approved
0.7232	Intermediate Similarity	NPD5283	Phase 1
0.7232	Intermediate Similarity	NPD498	Approved
0.7232	Intermediate Similarity	NPD495	Approved
0.7217	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2562	Approved
0.7203	Intermediate Similarity	NPD1481	Phase 2
0.7203	Intermediate Similarity	NPD2561	Approved
0.7193	Intermediate Similarity	NPD9568	Approved
0.7193	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3847	Discontinued
0.7179	Intermediate Similarity	NPD3421	Phase 3
0.7168	Intermediate Similarity	NPD475	Phase 2
0.7167	Intermediate Similarity	NPD4103	Phase 2
0.7167	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1470	Approved
0.7167	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD9093	Approved
0.7156	Intermediate Similarity	NPD9267	Approved
0.7156	Intermediate Similarity	NPD9264	Approved
0.7156	Intermediate Similarity	NPD9263	Approved
0.7155	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD821	Approved
0.7143	Intermediate Similarity	NPD7843	Approved
0.713	Intermediate Similarity	NPD16	Approved
0.713	Intermediate Similarity	NPD856	Approved
0.713	Intermediate Similarity	NPD317	Approved
0.713	Intermediate Similarity	NPD318	Approved
0.7117	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6584	Phase 3
0.7097	Intermediate Similarity	NPD6407	Approved
0.7097	Intermediate Similarity	NPD6405	Approved
0.7094	Intermediate Similarity	NPD3095	Discontinued
0.7094	Intermediate Similarity	NPD2668	Approved
0.7094	Intermediate Similarity	NPD2667	Approved
0.7094	Intermediate Similarity	NPD5846	Approved
0.7094	Intermediate Similarity	NPD6516	Phase 2
0.7094	Intermediate Similarity	NPD4626	Approved
0.7083	Intermediate Similarity	NPD5310	Approved
0.7083	Intermediate Similarity	NPD5311	Approved
0.7075	Intermediate Similarity	NPD1616	Discontinued
0.7069	Intermediate Similarity	NPD1759	Phase 1
0.7069	Intermediate Similarity	NPD1894	Discontinued
0.7043	Intermediate Similarity	NPD9493	Approved
0.704	Intermediate Similarity	NPD943	Approved
0.704	Intermediate Similarity	NPD1240	Approved
0.704	Intermediate Similarity	NPD1613	Approved
0.704	Intermediate Similarity	NPD4060	Phase 1
0.704	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1237	Approved
0.7034	Intermediate Similarity	NPD3143	Discontinued
0.7034	Intermediate Similarity	NPD1983	Approved
0.7034	Intermediate Similarity	NPD1980	Approved
0.7034	Intermediate Similarity	NPD1981	Approved
0.7025	Intermediate Similarity	NPD1133	Approved
0.7025	Intermediate Similarity	NPD1131	Approved
0.7025	Intermediate Similarity	NPD3055	Approved
0.7025	Intermediate Similarity	NPD1129	Approved
0.7025	Intermediate Similarity	NPD1135	Approved
0.7025	Intermediate Similarity	NPD3094	Phase 2
0.7025	Intermediate Similarity	NPD3053	Approved
0.7025	Intermediate Similarity	NPD1134	Approved
0.7025	Intermediate Similarity	NPD2797	Approved
0.7018	Intermediate Similarity	NPD9618	Approved
0.7018	Intermediate Similarity	NPD9614	Approved
0.7018	Intermediate Similarity	NPD1793	Approved
0.7018	Intermediate Similarity	NPD1791	Approved
0.6983	Remote Similarity	NPD1758	Phase 1
0.6975	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9697	Approved
0.6967	Remote Similarity	NPD7451	Discontinued
0.6957	Remote Similarity	NPD7157	Approved
0.6957	Remote Similarity	NPD2557	Approved
0.6957	Remote Similarity	NPD6387	Discontinued
0.6949	Remote Similarity	NPD9381	Approved
0.6949	Remote Similarity	NPD9384	Approved
0.6944	Remote Similarity	NPD4658	Approved
0.6944	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4656	Approved
0.6942	Remote Similarity	NPD1283	Approved
0.6935	Remote Similarity	NPD2372	Approved
0.6935	Remote Similarity	NPD3027	Phase 3
0.6935	Remote Similarity	NPD4625	Phase 3
0.6931	Remote Similarity	NPD9295	Approved
0.6929	Remote Similarity	NPD1607	Approved
0.6923	Remote Similarity	NPD9545	Approved
0.6917	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3070	Discontinued
0.6917	Remote Similarity	NPD2230	Approved
0.6917	Remote Similarity	NPD2233	Approved
0.6917	Remote Similarity	NPD2232	Approved
0.6911	Remote Similarity	NPD5736	Approved
0.6905	Remote Similarity	NPD1555	Discontinued
0.6897	Remote Similarity	NPD7636	Approved
0.6897	Remote Similarity	NPD3596	Phase 2
0.6893	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1203	Approved
0.688	Remote Similarity	NPD6798	Discontinued
0.688	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.688	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD3552	Approved
0.6875	Remote Similarity	NPD3554	Approved
0.6875	Remote Similarity	NPD3555	Approved
0.6875	Remote Similarity	NPD3553	Approved
0.6869	Remote Similarity	NPD9073	Approved
0.6864	Remote Similarity	NPD1651	Approved
0.686	Remote Similarity	NPD4749	Approved
0.686	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1669	Approved
0.6852	Remote Similarity	NPD4817	Approved
0.6852	Remote Similarity	NPD4818	Approved
0.6842	Remote Similarity	NPD1138	Approved
0.6838	Remote Similarity	NPD9616	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