NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.2
Volume:	274.434
LogP:	4.501
LogD:	2.176
LogS:	-3.775
# Rotatable Bonds:	12
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	2.344
Fsp3:	0.929
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.991
MDCK Permeability:	4.2030700569739565e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.144
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.877
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.845
Plasma Protein Binding (PPB):	95.03404998779297%
Volume Distribution (VD):	0.357
Pgp-substrate:	2.9973387718200684%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.273
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.397
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.036

ADMET: Excretion

Clearance (CL):	5.363
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.681
Skin Sensitization:	0.802
Carcinogencity:	0.184
Eye Corrosion:	0.963
Eye Irritation:	0.989
Respiratory Toxicity:	0.741

Download Data

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

Natural Product: NPC200618

Natural Product ID:	NPC200618
*Common Name:**	3-Hydroxymyristic Acid
IUPAC Name:	(3R)-3-hydroxytetradecanoic acid
Synonyms:	3-Hydroxymyristic Acid
Standard InCHIKey:	ATRNZOYKSNPPBF-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1
SMILES:	CCCCCCCCCCC[C@H](CC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1232858
PubChem CID:	5288266
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1078/0176-1617-00195]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757735]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14735439]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	callus	n.a.	PMID[15715262]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28445039]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30024167]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	2
Ki	1
MIC	7
Others	2

Activity Type	# Activity
Organism	5
Others	2
SINGLE PROTEIN	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown		MIC	=	10.0	ug.mL-1	PMID[493390]
NPT772	Organism	Pichia anomala	Wickerhamomyces anomalus	MIC	=	10.0	ug.mL-1	PMID[493390]
NPT3153	Organism	Kluyveromyces marxianus	Kluyveromyces marxianus	MIC	=	10.0	ug.mL-1	PMID[493390]
NPT4521	Organism	Penicillium roqueforti	Penicillium roqueforti	MIC	=	10.0	ug.mL-1	PMID[493390]
NPT925	Organism	Emericella nidulans	Emericella nidulans	MIC	=	10.0	ug.mL-1	PMID[493390]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	10.0	ug.mL-1	PMID[493390]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	Ki	=	472.0	nM	PMID[493391]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	EC50	=	1750.0	nM	PMID[493391]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	Emax	=	91.0	%	PMID[493391]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	EC50	=	452.0	nM	PMID[493391]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	Emax	=	77.0	%	PMID[493391]

☑ 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 NPC200618 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	779
0.1-0.2	7999
0.2-0.3	18033
0.3-0.4	10098
0.4-0.5	4718
0.5-0.6	788
0.6-0.7	182
0.7-0.8	70
0.8-0.85	18
0.85-0.9	5
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC131770
0.9565	High Similarity	NPC90904
0.8913	High Similarity	NPC324004
0.8913	High Similarity	NPC328497
0.8723	High Similarity	NPC106872
0.8667	High Similarity	NPC76051
0.8542	High Similarity	NPC304162
0.8298	Intermediate Similarity	NPC30195
0.8298	Intermediate Similarity	NPC12438
0.8182	Intermediate Similarity	NPC14227
0.8182	Intermediate Similarity	NPC154186
0.8182	Intermediate Similarity	NPC301696
0.8182	Intermediate Similarity	NPC201844
0.8182	Intermediate Similarity	NPC301585
0.8182	Intermediate Similarity	NPC279026
0.8182	Intermediate Similarity	NPC261080
0.8182	Intermediate Similarity	NPC113928
0.8085	Intermediate Similarity	NPC469781
0.8077	Intermediate Similarity	NPC23155
0.8077	Intermediate Similarity	NPC469937
0.8077	Intermediate Similarity	NPC53463
0.8077	Intermediate Similarity	NPC320588
0.8	Intermediate Similarity	NPC17935
0.7872	Intermediate Similarity	NPC74845
0.7843	Intermediate Similarity	NPC100096
0.7826	Intermediate Similarity	NPC171736
0.7826	Intermediate Similarity	NPC216630
0.7826	Intermediate Similarity	NPC307783
0.7826	Intermediate Similarity	NPC149184
0.7826	Intermediate Similarity	NPC209970
0.7826	Intermediate Similarity	NPC196924
0.7778	Intermediate Similarity	NPC183424
0.7778	Intermediate Similarity	NPC294085
0.7778	Intermediate Similarity	NPC214610
0.7778	Intermediate Similarity	NPC118968
0.7708	Intermediate Similarity	NPC47363
0.7708	Intermediate Similarity	NPC287231
0.7679	Intermediate Similarity	NPC475821
0.766	Intermediate Similarity	NPC67462
0.7609	Intermediate Similarity	NPC149299
0.7609	Intermediate Similarity	NPC40597
0.7609	Intermediate Similarity	NPC250028
0.7609	Intermediate Similarity	NPC256163
0.7556	Intermediate Similarity	NPC268826
0.7556	Intermediate Similarity	NPC201622
0.7556	Intermediate Similarity	NPC54980
0.7556	Intermediate Similarity	NPC22903
0.7556	Intermediate Similarity	NPC305660
0.7551	Intermediate Similarity	NPC52700
0.7551	Intermediate Similarity	NPC105329
0.7551	Intermediate Similarity	NPC145045
0.7551	Intermediate Similarity	NPC63182
0.75	Intermediate Similarity	NPC255837
0.75	Intermediate Similarity	NPC19305
0.75	Intermediate Similarity	NPC155263
0.7458	Intermediate Similarity	NPC314103
0.7451	Intermediate Similarity	NPC26253
0.7447	Intermediate Similarity	NPC53541
0.74	Intermediate Similarity	NPC326957
0.7391	Intermediate Similarity	NPC223249
0.7391	Intermediate Similarity	NPC80234
0.7391	Intermediate Similarity	NPC31551
0.7391	Intermediate Similarity	NPC219536
0.7368	Intermediate Similarity	NPC470363
0.7347	Intermediate Similarity	NPC273545
0.7347	Intermediate Similarity	NPC8219
0.7347	Intermediate Similarity	NPC55023
0.7333	Intermediate Similarity	NPC476330
0.7308	Intermediate Similarity	NPC55678
0.7292	Intermediate Similarity	NPC236579
0.7292	Intermediate Similarity	NPC203531
0.7288	Intermediate Similarity	NPC474552
0.7273	Intermediate Similarity	NPC191084
0.7273	Intermediate Similarity	NPC250870
0.7273	Intermediate Similarity	NPC317203
0.7273	Intermediate Similarity	NPC168052
0.7273	Intermediate Similarity	NPC156630
0.7234	Intermediate Similarity	NPC161097
0.7234	Intermediate Similarity	NPC28598
0.7234	Intermediate Similarity	NPC165533
0.72	Intermediate Similarity	NPC314679
0.7111	Intermediate Similarity	NPC134782
0.7097	Intermediate Similarity	NPC469925
0.7083	Intermediate Similarity	NPC163746
0.7083	Intermediate Similarity	NPC103286
0.7083	Intermediate Similarity	NPC474361
0.7059	Intermediate Similarity	NPC21844
0.6949	Remote Similarity	NPC243532
0.6939	Remote Similarity	NPC301528
0.6939	Remote Similarity	NPC176500
0.6939	Remote Similarity	NPC289686
0.6939	Remote Similarity	NPC71317
0.6939	Remote Similarity	NPC129972
0.6923	Remote Similarity	NPC477878
0.6923	Remote Similarity	NPC324793
0.6875	Remote Similarity	NPC12156
0.6852	Remote Similarity	NPC314084
0.6852	Remote Similarity	NPC287811
0.6852	Remote Similarity	NPC470411
0.6833	Remote Similarity	NPC201939
0.6833	Remote Similarity	NPC469923
0.6818	Remote Similarity	NPC175342
0.6818	Remote Similarity	NPC193062
0.6818	Remote Similarity	NPC66124
0.6818	Remote Similarity	NPC1748
0.6818	Remote Similarity	NPC319034
0.6818	Remote Similarity	NPC72324
0.6809	Remote Similarity	NPC73245
0.68	Remote Similarity	NPC317128
0.678	Remote Similarity	NPC472019
0.678	Remote Similarity	NPC472020
0.678	Remote Similarity	NPC469924
0.678	Remote Similarity	NPC226602
0.6739	Remote Similarity	NPC474392
0.6739	Remote Similarity	NPC80396
0.6739	Remote Similarity	NPC154642
0.6739	Remote Similarity	NPC474914
0.6739	Remote Similarity	NPC80641
0.6735	Remote Similarity	NPC325452
0.6735	Remote Similarity	NPC248763
0.6727	Remote Similarity	NPC277878
0.6721	Remote Similarity	NPC325773
0.6719	Remote Similarity	NPC319007
0.6667	Remote Similarity	NPC320119
0.6667	Remote Similarity	NPC469921
0.6667	Remote Similarity	NPC472021
0.6613	Remote Similarity	NPC226592
0.6613	Remote Similarity	NPC470320
0.6607	Remote Similarity	NPC196612
0.6604	Remote Similarity	NPC180534
0.6596	Remote Similarity	NPC109026
0.6591	Remote Similarity	NPC122962
0.6591	Remote Similarity	NPC267243
0.6567	Remote Similarity	NPC326024
0.6562	Remote Similarity	NPC206601
0.6562	Remote Similarity	NPC104537
0.6562	Remote Similarity	NPC330426
0.6562	Remote Similarity	NPC271921
0.6562	Remote Similarity	NPC148192
0.6562	Remote Similarity	NPC22101
0.6562	Remote Similarity	NPC127091
0.6545	Remote Similarity	NPC470410
0.6545	Remote Similarity	NPC470412
0.6538	Remote Similarity	NPC166287
0.6522	Remote Similarity	NPC86545
0.6522	Remote Similarity	NPC301398
0.6522	Remote Similarity	NPC196442
0.6522	Remote Similarity	NPC223374
0.6522	Remote Similarity	NPC97967
0.6515	Remote Similarity	NPC42526
0.6508	Remote Similarity	NPC245947
0.6508	Remote Similarity	NPC255863
0.6508	Remote Similarity	NPC136164
0.6491	Remote Similarity	NPC289979
0.6462	Remote Similarity	NPC48218
0.6462	Remote Similarity	NPC324981
0.6462	Remote Similarity	NPC141481
0.6462	Remote Similarity	NPC473559
0.6452	Remote Similarity	NPC235788
0.6444	Remote Similarity	NPC18224
0.6444	Remote Similarity	NPC328710
0.6429	Remote Similarity	NPC281245
0.6418	Remote Similarity	NPC474590
0.6379	Remote Similarity	NPC52264
0.6377	Remote Similarity	NPC228411
0.6377	Remote Similarity	NPC179922
0.6364	Remote Similarity	NPC24506
0.6364	Remote Similarity	NPC163556
0.6364	Remote Similarity	NPC225783
0.6364	Remote Similarity	NPC305182
0.6364	Remote Similarity	NPC236797
0.6364	Remote Similarity	NPC50457
0.6364	Remote Similarity	NPC185041
0.6364	Remote Similarity	NPC241265
0.6364	Remote Similarity	NPC147096
0.6364	Remote Similarity	NPC285003
0.6364	Remote Similarity	NPC112242
0.6349	Remote Similarity	NPC328089
0.6349	Remote Similarity	NPC68343
0.6327	Remote Similarity	NPC81263
0.6327	Remote Similarity	NPC3531
0.6327	Remote Similarity	NPC94368
0.6324	Remote Similarity	NPC144419
0.6316	Remote Similarity	NPC72722
0.6316	Remote Similarity	NPC1813
0.6316	Remote Similarity	NPC36061
0.6316	Remote Similarity	NPC139029
0.6316	Remote Similarity	NPC294548
0.6308	Remote Similarity	NPC26500
0.6308	Remote Similarity	NPC475443
0.6308	Remote Similarity	NPC473829
0.6308	Remote Similarity	NPC99619
0.6304	Remote Similarity	NPC57499
0.6304	Remote Similarity	NPC286498
0.6304	Remote Similarity	NPC154396
0.6296	Remote Similarity	NPC216130
0.629	Remote Similarity	NPC321838
0.6286	Remote Similarity	NPC474020
0.6286	Remote Similarity	NPC49392
0.6286	Remote Similarity	NPC190400

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 NPC200618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1197
0.1-0.2	4758
0.2-0.3	2002
0.3-0.4	795
0.4-0.5	260
0.5-0.6	98
0.6-0.7	27
0.7-0.8	10
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD9448	Phase 2
0.8182	Intermediate Similarity	NPD633	Phase 3
0.8077	Intermediate Similarity	NPD3730	Approved
0.8077	Intermediate Similarity	NPD3728	Approved
0.7826	Intermediate Similarity	NPD2270	Approved
0.7778	Intermediate Similarity	NPD9655	Approved
0.7736	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2699	Approved
0.7347	Intermediate Similarity	NPD3199	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD634	Phase 3
0.7174	Intermediate Similarity	NPD3206	Approved
0.7143	Intermediate Similarity	NPD73	Approved
0.7069	Intermediate Similarity	NPD3198	Approved
0.6852	Remote Similarity	NPD9638	Phase 2
0.6727	Remote Similarity	NPD9007	Approved
0.6727	Remote Similarity	NPD9011	Approved
0.6727	Remote Similarity	NPD64	Approved
0.6727	Remote Similarity	NPD9009	Approved
0.6727	Remote Similarity	NPD72	Approved
0.6727	Remote Similarity	NPD9010	Approved
0.6727	Remote Similarity	NPD8960	Approved
0.6727	Remote Similarity	NPD65	Approved
0.6727	Remote Similarity	NPD66	Approved
0.6727	Remote Similarity	NPD9008	Approved
0.6613	Remote Similarity	NPD3197	Phase 1
0.6613	Remote Similarity	NPD7909	Approved
0.6604	Remote Similarity	NPD622	Approved
0.66	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD9430	Approved
0.6538	Remote Similarity	NPD9431	Approved
0.6491	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3186	Phase 1
0.6327	Remote Similarity	NPD9450	Approved
0.6327	Remote Similarity	NPD77	Approved
0.6316	Remote Similarity	NPD3172	Approved
0.6296	Remote Similarity	NPD2266	Phase 2
0.6207	Remote Similarity	NPD4266	Approved
0.6207	Remote Similarity	NPD3195	Phase 2
0.6207	Remote Similarity	NPD3194	Approved
0.6207	Remote Similarity	NPD3196	Approved
0.6182	Remote Similarity	NPD8964	Approved
0.6167	Remote Similarity	NPD8959	Approved
0.6122	Remote Similarity	NPD9513	Phase 1
0.6087	Remote Similarity	NPD2272	Approved
0.6087	Remote Similarity	NPD5383	Approved
0.6	Remote Similarity	NPD9003	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9005	Phase 3
0.6	Remote Similarity	NPD9004	Approved
0.5965	Remote Similarity	NPD9002	Approved
0.5965	Remote Similarity	NPD9001	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD8857	Approved
0.5942	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.589	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.589	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD896	Approved
0.5821	Remote Similarity	NPD897	Approved
0.5821	Remote Similarity	NPD898	Approved
0.5781	Remote Similarity	NPD4283	Discontinued
0.5775	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD8603	Approved
0.5769	Remote Similarity	NPD8604	Approved
0.5769	Remote Similarity	NPD8601	Approved
0.5769	Remote Similarity	NPD8600	Approved
0.5769	Remote Similarity	NPD8599	Approved
0.5769	Remote Similarity	NPD8605	Approved
0.5769	Remote Similarity	NPD8602	Approved
0.5769	Remote Similarity	NPD8598	Approved
0.5758	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD229	Approved
0.5692	Remote Similarity	NPD8961	Approved
0.569	Remote Similarity	NPD29	Approved
0.569	Remote Similarity	NPD28	Approved
0.5676	Remote Similarity	NPD4802	Phase 2
0.5676	Remote Similarity	NPD3732	Approved
0.5676	Remote Similarity	NPD4238	Approved
0.5658	Remote Similarity	NPD5369	Approved
0.5652	Remote Similarity	NPD8590	Approved
0.5652	Remote Similarity	NPD8618	Approved
0.5652	Remote Similarity	NPD8277	Approved
0.5616	Remote Similarity	NPD6117	Approved
0.5614	Remote Similarity	NPD8624	Approved
0.5614	Remote Similarity	NPD3173	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