NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	383.07
Volume:	354.976
LogP:	5.43
LogD:	3.719
LogS:	-4.331
# Rotatable Bonds:	5
TPSA:	66.84
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	3.995
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.643
MDCK Permeability:	2.499336733308155e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.708
Plasma Protein Binding (PPB):	93.5519027709961%
Volume Distribution (VD):	0.642
Pgp-substrate:	8.165051460266113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.902
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.386
CYP3A4-inhibitor:	0.738
CYP3A4-substrate:	0.743

ADMET: Excretion

Clearance (CL):	4.703
Half-life (T1/2):	0.335

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.827
Rat Oral Acute Toxicity:	0.642
Maximum Recommended Daily Dose:	0.24
Skin Sensitization:	0.551
Carcinogencity:	0.866
Eye Corrosion:	0.004
Eye Irritation:	0.048
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC223374

Natural Product ID:	NPC223374
*Common Name:**	Nonylacetate
IUPAC Name:	nonyl acetate
Synonyms:
Standard InCHIKey:	GJQIMXVRFNLMTB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H22O2/c1-3-4-5-6-7-8-9-10-13-11(2)12/h3-10H2,1-2H3
SMILES:	CCCCCCCCCOC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2228457
PubChem CID:	8918
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001722] Fatty alcohol esters

*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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80°N and longitude 4°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8952	Craibiodendron yunnanese	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8952	Craibiodendron yunnanese	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17024	Vitis vinifera	Species	Vitaceae	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
Others	1
Potency	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	mortality	=	3.1	%	PMID[544265]
NPT2	Others	Unspecified		Potency	n.a.	173.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	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 NPC223374 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	1141
0.1-0.2	19091
0.2-0.3	14174
0.3-0.4	6832
0.4-0.5	1056
0.5-0.6	204
0.6-0.7	134
0.7-0.8	41
0.8-0.85	9
0.85-0.9	7
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86545
1.0	High Similarity	NPC196442
1.0	High Similarity	NPC301398
0.9688	High Similarity	NPC286498
0.9412	High Similarity	NPC128996
0.9118	High Similarity	NPC80641
0.9062	High Similarity	NPC40965
0.8788	High Similarity	NPC322892
0.8649	High Similarity	NPC149299
0.8649	High Similarity	NPC40597
0.8649	High Similarity	NPC250028
0.8649	High Similarity	NPC256163
0.8529	High Similarity	NPC154396
0.8421	Intermediate Similarity	NPC53541
0.8378	Intermediate Similarity	NPC223249
0.8378	Intermediate Similarity	NPC80234
0.8286	Intermediate Similarity	NPC155872
0.8235	Intermediate Similarity	NPC147054
0.8205	Intermediate Similarity	NPC203531
0.8205	Intermediate Similarity	NPC236579
0.8158	Intermediate Similarity	NPC165533
0.8108	Intermediate Similarity	NPC201622
0.8108	Intermediate Similarity	NPC54980
0.8108	Intermediate Similarity	NPC305660
0.8108	Intermediate Similarity	NPC316546
0.8108	Intermediate Similarity	NPC22903
0.8056	Intermediate Similarity	NPC154642
0.8056	Intermediate Similarity	NPC80396
0.7941	Intermediate Similarity	NPC12904
0.7895	Intermediate Similarity	NPC31551
0.7895	Intermediate Similarity	NPC219536
0.7838	Intermediate Similarity	NPC14608
0.7812	Intermediate Similarity	NPC248233
0.7805	Intermediate Similarity	NPC287231
0.7805	Intermediate Similarity	NPC47363
0.7714	Intermediate Similarity	NPC286695
0.7692	Intermediate Similarity	NPC28598
0.7692	Intermediate Similarity	NPC161097
0.7692	Intermediate Similarity	NPC12156
0.7619	Intermediate Similarity	NPC145045
0.7619	Intermediate Similarity	NPC63182
0.7619	Intermediate Similarity	NPC52700
0.7619	Intermediate Similarity	NPC105329
0.7442	Intermediate Similarity	NPC326957
0.7436	Intermediate Similarity	NPC81263
0.7381	Intermediate Similarity	NPC273545
0.7297	Intermediate Similarity	NPC156630
0.7273	Intermediate Similarity	NPC68577
0.7209	Intermediate Similarity	NPC12438
0.7209	Intermediate Similarity	NPC30195
0.7188	Intermediate Similarity	NPC3693
0.7143	Intermediate Similarity	NPC317128
0.7111	Intermediate Similarity	NPC207815
0.7111	Intermediate Similarity	NPC223675
0.7111	Intermediate Similarity	NPC26253
0.7059	Intermediate Similarity	NPC159398
0.7045	Intermediate Similarity	NPC249754
0.7027	Intermediate Similarity	NPC57499
0.7	Intermediate Similarity	NPC113928
0.7	Intermediate Similarity	NPC301585
0.7	Intermediate Similarity	NPC279026
0.7	Intermediate Similarity	NPC225963
0.7	Intermediate Similarity	NPC301696
0.7	Intermediate Similarity	NPC474205
0.7	Intermediate Similarity	NPC201844
0.7	Intermediate Similarity	NPC14227
0.7	Intermediate Similarity	NPC261080
0.7	Intermediate Similarity	NPC154186
0.697	Remote Similarity	NPC166804
0.6957	Remote Similarity	NPC55678
0.6957	Remote Similarity	NPC305182
0.6957	Remote Similarity	NPC142103
0.6944	Remote Similarity	NPC272426
0.6905	Remote Similarity	NPC176500
0.6889	Remote Similarity	NPC106872
0.6875	Remote Similarity	NPC110107
0.6857	Remote Similarity	NPC127696
0.6842	Remote Similarity	NPC289344
0.6818	Remote Similarity	NPC282440
0.6818	Remote Similarity	NPC308301
0.6809	Remote Similarity	NPC291724
0.6809	Remote Similarity	NPC287811
0.6809	Remote Similarity	NPC314084
0.6809	Remote Similarity	NPC274261
0.6765	Remote Similarity	NPC143211
0.6757	Remote Similarity	NPC168714
0.6757	Remote Similarity	NPC35371
0.6757	Remote Similarity	NPC178643
0.6757	Remote Similarity	NPC41007
0.675	Remote Similarity	NPC197039
0.6739	Remote Similarity	NPC250919
0.6667	Remote Similarity	NPC310746
0.6667	Remote Similarity	NPC236797
0.6667	Remote Similarity	NPC171736
0.6667	Remote Similarity	NPC324004
0.6667	Remote Similarity	NPC147096
0.6667	Remote Similarity	NPC163556
0.6667	Remote Similarity	NPC307783
0.6667	Remote Similarity	NPC32280
0.6667	Remote Similarity	NPC185041
0.6667	Remote Similarity	NPC41485
0.6667	Remote Similarity	NPC225783
0.6667	Remote Similarity	NPC149184
0.6667	Remote Similarity	NPC196924
0.6667	Remote Similarity	NPC216630
0.6667	Remote Similarity	NPC209970
0.6667	Remote Similarity	NPC112242
0.6667	Remote Similarity	NPC24506
0.6667	Remote Similarity	NPC328497
0.6591	Remote Similarity	NPC312547
0.6585	Remote Similarity	NPC294085
0.6585	Remote Similarity	NPC94368
0.6585	Remote Similarity	NPC183424
0.6585	Remote Similarity	NPC118968
0.6585	Remote Similarity	NPC214610
0.6579	Remote Similarity	NPC140229
0.6579	Remote Similarity	NPC139569
0.6579	Remote Similarity	NPC474089
0.6579	Remote Similarity	NPC474120
0.6571	Remote Similarity	NPC317739
0.6571	Remote Similarity	NPC281943
0.6562	Remote Similarity	NPC23508
0.6522	Remote Similarity	NPC200618
0.6522	Remote Similarity	NPC216130
0.6522	Remote Similarity	NPC131770
0.6512	Remote Similarity	NPC144829
0.6512	Remote Similarity	NPC67462
0.65	Remote Similarity	NPC74352
0.6486	Remote Similarity	NPC126915
0.6471	Remote Similarity	NPC127134
0.6471	Remote Similarity	NPC201132
0.6444	Remote Similarity	NPC172042
0.6429	Remote Similarity	NPC152008
0.64	Remote Similarity	NPC320588
0.64	Remote Similarity	NPC469937
0.64	Remote Similarity	NPC23155
0.64	Remote Similarity	NPC53463
0.64	Remote Similarity	NPC289979
0.6383	Remote Similarity	NPC304162
0.6364	Remote Similarity	NPC19305
0.6364	Remote Similarity	NPC255837
0.6364	Remote Similarity	NPC74845
0.6341	Remote Similarity	NPC268826
0.6316	Remote Similarity	NPC108238
0.6316	Remote Similarity	NPC12231
0.6316	Remote Similarity	NPC205141
0.6316	Remote Similarity	NPC193062
0.6316	Remote Similarity	NPC272998
0.6316	Remote Similarity	NPC319034
0.6316	Remote Similarity	NPC152759
0.6316	Remote Similarity	NPC181516
0.6316	Remote Similarity	NPC185538
0.6316	Remote Similarity	NPC139131
0.6316	Remote Similarity	NPC66124
0.6316	Remote Similarity	NPC99700
0.6316	Remote Similarity	NPC72324
0.6316	Remote Similarity	NPC291158
0.6316	Remote Similarity	NPC1748
0.6279	Remote Similarity	NPC103286
0.6279	Remote Similarity	NPC163746
0.6275	Remote Similarity	NPC223677
0.6275	Remote Similarity	NPC200845
0.6275	Remote Similarity	NPC10316
0.6275	Remote Similarity	NPC128061
0.6275	Remote Similarity	NPC28779
0.625	Remote Similarity	NPC474914
0.625	Remote Similarity	NPC155263
0.625	Remote Similarity	NPC321699
0.625	Remote Similarity	NPC90904
0.625	Remote Similarity	NPC474392
0.6222	Remote Similarity	NPC8219
0.6222	Remote Similarity	NPC55023
0.6216	Remote Similarity	NPC21374
0.62	Remote Similarity	NPC71761
0.6176	Remote Similarity	NPC28246
0.6136	Remote Similarity	NPC301528
0.6136	Remote Similarity	NPC129972
0.6136	Remote Similarity	NPC325102
0.6136	Remote Similarity	NPC71317
0.6111	Remote Similarity	NPC88135
0.6111	Remote Similarity	NPC279895
0.6087	Remote Similarity	NPC314679
0.6061	Remote Similarity	NPC8187
0.6061	Remote Similarity	NPC203105
0.6053	Remote Similarity	NPC122962
0.6053	Remote Similarity	NPC267243
0.6053	Remote Similarity	NPC281883
0.6042	Remote Similarity	NPC163345
0.6	Remote Similarity	NPC97967
0.6	Remote Similarity	NPC317203
0.6	Remote Similarity	NPC161366
0.6	Remote Similarity	NPC211250
0.6	Remote Similarity	NPC76051
0.5962	Remote Similarity	NPC52264
0.5957	Remote Similarity	NPC21844
0.5952	Remote Similarity	NPC73245
0.5938	Remote Similarity	NPC61373
0.5926	Remote Similarity	NPC469373
0.5926	Remote Similarity	NPC240206
0.5918	Remote Similarity	NPC289388

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 NPC223374 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1523
0.1-0.2	5491
0.2-0.3	1480
0.3-0.4	465
0.4-0.5	134
0.5-0.6	36
0.6-0.7	20
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7805	Intermediate Similarity	NPD2699	Approved
0.7179	Intermediate Similarity	NPD3206	Approved
0.7	Intermediate Similarity	NPD9448	Phase 2
0.7	Intermediate Similarity	NPD633	Phase 3
0.6944	Remote Similarity	NPD908	Approved
0.6944	Remote Similarity	NPD1461	Approved
0.6944	Remote Similarity	NPD907	Approved
0.6889	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2270	Approved
0.6667	Remote Similarity	NPD370	Phase 3
0.6585	Remote Similarity	NPD9655	Approved
0.6579	Remote Similarity	NPD900	Approved
0.6512	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8989	Approved
0.6429	Remote Similarity	NPD7536	Approved
0.64	Remote Similarity	NPD3730	Approved
0.64	Remote Similarity	NPD3728	Approved
0.6316	Remote Similarity	NPD5383	Approved
0.6316	Remote Similarity	NPD2272	Approved
0.6222	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.617	Remote Similarity	NPD2266	Phase 2
0.6098	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD634	Phase 3
0.6053	Remote Similarity	NPD9636	Phase 2
0.6	Remote Similarity	NPD9447	Approved
0.5814	Remote Similarity	NPD9450	Approved
0.5814	Remote Similarity	NPD5799	Discontinued
0.5814	Remote Similarity	NPD77	Approved
0.58	Remote Similarity	NPD1399	Approved
0.58	Remote Similarity	NPD1400	Approved
0.5789	Remote Similarity	NPD8856	Phase 2
0.5769	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD1460	Approved
0.5614	Remote Similarity	NPD3205	Discontinued

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