NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	198.16
Volume:	228.416
LogP:	4.286
LogD:	3.559
LogS:	-4.285
# Rotatable Bonds:	10
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	1.937
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.562
MDCK Permeability:	2.585617585282307e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.677

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999
Plasma Protein Binding (PPB):	90.26639556884766%
Volume Distribution (VD):	0.729
Pgp-substrate:	11.801236152648926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.557
CYP2C19-inhibitor:	0.729
CYP2C19-substrate:	0.497
CYP2C9-inhibitor:	0.508
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.328
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	7.471
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.955
Carcinogencity:	0.539
Eye Corrosion:	0.962
Eye Irritation:	0.978
Respiratory Toxicity:	0.831

Download Data

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

Natural Product: NPC216130

Natural Product ID:	NPC216130
*Common Name:**	Methyl Undec-10-Enoate
IUPAC Name:	methyl undec-10-enoate
Synonyms:
Standard InCHIKey:	KISVAASFGZJBCY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H22O2/c1-3-4-5-6-7-8-9-10-11-12(13)14-2/h3H,1,4-11H2,2H3
SMILES:	C=CCCCCCCCCC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1591973
PubChem CID:	8138
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters [CHEMONTID:0003417] Fatty acid methyl 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]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	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]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
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]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
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	Leaf Essent. Oil	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	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]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13879	Humulus lupulus	Species	Cannabaceae	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	10
Others	1
Potency	3

Activity Type	# Activity
Individual Protein	2
Others	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	1258.9	nM	PMID[523489]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[523489]
NPT2	Others	Unspecified		Activity	=	96.0	%	PMID[523490]
NPT2	Others	Unspecified		IC50	n.a.	20000.0	nM	PMID[523491]
NPT2	Others	Unspecified		IC50	n.a.	10000.0	nM	PMID[523491]
NPT2	Others	Unspecified		Potency	n.a.	33491.5	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 NPC216130 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	160
0.1-0.2	4823
0.2-0.3	19978
0.3-0.4	10743
0.4-0.5	5303
0.5-0.6	1331
0.6-0.7	239
0.7-0.8	84
0.8-0.85	23
0.85-0.9	8
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC161366
0.898	High Similarity	NPC309606
0.898	High Similarity	NPC39633
0.898	High Similarity	NPC139545
0.875	High Similarity	NPC224227
0.8723	High Similarity	NPC180534
0.8627	High Similarity	NPC28779
0.8627	High Similarity	NPC223677
0.8627	High Similarity	NPC128061
0.8627	High Similarity	NPC228473
0.8627	High Similarity	NPC200845
0.8627	High Similarity	NPC10316
0.86	High Similarity	NPC71761
0.8571	High Similarity	NPC262968
0.84	Intermediate Similarity	NPC281245
0.8235	Intermediate Similarity	NPC1813
0.8235	Intermediate Similarity	NPC294548
0.8235	Intermediate Similarity	NPC139029
0.8235	Intermediate Similarity	NPC36061
0.8163	Intermediate Similarity	NPC250919
0.8077	Intermediate Similarity	NPC88966
0.8077	Intermediate Similarity	NPC281972
0.8077	Intermediate Similarity	NPC32467
0.8077	Intermediate Similarity	NPC424
0.8077	Intermediate Similarity	NPC87564
0.8077	Intermediate Similarity	NPC6095
0.8077	Intermediate Similarity	NPC25417
0.8077	Intermediate Similarity	NPC85813
0.8077	Intermediate Similarity	NPC154245
0.8077	Intermediate Similarity	NPC261831
0.8077	Intermediate Similarity	NPC290563
0.8039	Intermediate Similarity	NPC310746
0.8039	Intermediate Similarity	NPC18357
0.7955	Intermediate Similarity	NPC201622
0.7955	Intermediate Similarity	NPC22903
0.7955	Intermediate Similarity	NPC54980
0.7955	Intermediate Similarity	NPC305660
0.7885	Intermediate Similarity	NPC70387
0.7885	Intermediate Similarity	NPC321062
0.7857	Intermediate Similarity	NPC45097
0.7857	Intermediate Similarity	NPC143857
0.7857	Intermediate Similarity	NPC229252
0.7843	Intermediate Similarity	NPC470410
0.7843	Intermediate Similarity	NPC470412
0.78	Intermediate Similarity	NPC163345
0.78	Intermediate Similarity	NPC207815
0.7778	Intermediate Similarity	NPC477201
0.7778	Intermediate Similarity	NPC187777
0.7778	Intermediate Similarity	NPC18951
0.7778	Intermediate Similarity	NPC179764
0.7778	Intermediate Similarity	NPC219536
0.7778	Intermediate Similarity	NPC31551
0.7719	Intermediate Similarity	NPC201939
0.7692	Intermediate Similarity	NPC92114
0.7636	Intermediate Similarity	NPC225929
0.7609	Intermediate Similarity	NPC149299
0.7609	Intermediate Similarity	NPC250028
0.7609	Intermediate Similarity	NPC40597
0.7609	Intermediate Similarity	NPC161097
0.7609	Intermediate Similarity	NPC28598
0.7609	Intermediate Similarity	NPC256163
0.7593	Intermediate Similarity	NPC473863
0.7593	Intermediate Similarity	NPC274290
0.7593	Intermediate Similarity	NPC54766
0.7593	Intermediate Similarity	NPC52264
0.7586	Intermediate Similarity	NPC54925
0.7551	Intermediate Similarity	NPC172042
0.7544	Intermediate Similarity	NPC243532
0.7458	Intermediate Similarity	NPC328089
0.7458	Intermediate Similarity	NPC68343
0.7451	Intermediate Similarity	NPC149821
0.7451	Intermediate Similarity	NPC5413
0.7447	Intermediate Similarity	NPC53541
0.7407	Intermediate Similarity	NPC137538
0.7391	Intermediate Similarity	NPC223249
0.7391	Intermediate Similarity	NPC80234
0.7368	Intermediate Similarity	NPC106851
0.7368	Intermediate Similarity	NPC274927
0.7358	Intermediate Similarity	NPC216407
0.7308	Intermediate Similarity	NPC59051
0.7292	Intermediate Similarity	NPC236579
0.7292	Intermediate Similarity	NPC203531
0.7273	Intermediate Similarity	NPC156630
0.7273	Intermediate Similarity	NPC474672
0.7255	Intermediate Similarity	NPC207292
0.7241	Intermediate Similarity	NPC235242
0.7241	Intermediate Similarity	NPC174447
0.7241	Intermediate Similarity	NPC251042
0.7241	Intermediate Similarity	NPC122521
0.7234	Intermediate Similarity	NPC48930
0.7234	Intermediate Similarity	NPC12156
0.7234	Intermediate Similarity	NPC165533
0.7213	Intermediate Similarity	NPC154728
0.7213	Intermediate Similarity	NPC126899
0.7213	Intermediate Similarity	NPC304665
0.7193	Intermediate Similarity	NPC34416
0.717	Intermediate Similarity	NPC28205
0.7167	Intermediate Similarity	NPC470320
0.7119	Intermediate Similarity	NPC40082
0.7119	Intermediate Similarity	NPC328776
0.7119	Intermediate Similarity	NPC320305
0.7097	Intermediate Similarity	NPC330426
0.7097	Intermediate Similarity	NPC148192
0.7097	Intermediate Similarity	NPC475443
0.7097	Intermediate Similarity	NPC22101
0.7097	Intermediate Similarity	NPC473829
0.7097	Intermediate Similarity	NPC104537
0.7097	Intermediate Similarity	NPC127091
0.7097	Intermediate Similarity	NPC271921
0.7049	Intermediate Similarity	NPC136164
0.7049	Intermediate Similarity	NPC326268
0.7049	Intermediate Similarity	NPC318420
0.7049	Intermediate Similarity	NPC245947
0.7049	Intermediate Similarity	NPC255863
0.7021	Intermediate Similarity	NPC201844
0.7021	Intermediate Similarity	NPC279026
0.7021	Intermediate Similarity	NPC14227
0.7021	Intermediate Similarity	NPC154186
0.7021	Intermediate Similarity	NPC301585
0.7021	Intermediate Similarity	NPC113928
0.7021	Intermediate Similarity	NPC301696
0.7021	Intermediate Similarity	NPC261080
0.7	Intermediate Similarity	NPC47363
0.7	Intermediate Similarity	NPC287231
0.6984	Remote Similarity	NPC141481
0.6984	Remote Similarity	NPC218477
0.6984	Remote Similarity	NPC48218
0.6984	Remote Similarity	NPC473559
0.6984	Remote Similarity	NPC324981
0.6981	Remote Similarity	NPC142103
0.6923	Remote Similarity	NPC91495
0.6897	Remote Similarity	NPC267817
0.6885	Remote Similarity	NPC226592
0.6875	Remote Similarity	NPC317583
0.6875	Remote Similarity	NPC473772
0.6875	Remote Similarity	NPC199557
0.6863	Remote Similarity	NPC105329
0.6863	Remote Similarity	NPC117572
0.6863	Remote Similarity	NPC63182
0.6863	Remote Similarity	NPC30195
0.6863	Remote Similarity	NPC145045
0.6863	Remote Similarity	NPC239754
0.6863	Remote Similarity	NPC52700
0.6863	Remote Similarity	NPC12438
0.6852	Remote Similarity	NPC284212
0.6852	Remote Similarity	NPC470411
0.6833	Remote Similarity	NPC125312
0.6833	Remote Similarity	NPC321838
0.6833	Remote Similarity	NPC174560
0.6825	Remote Similarity	NPC26500
0.6825	Remote Similarity	NPC99619
0.68	Remote Similarity	NPC317128
0.6786	Remote Similarity	NPC87394
0.6769	Remote Similarity	NPC476660
0.6769	Remote Similarity	NPC42526
0.6739	Remote Similarity	NPC80396
0.6739	Remote Similarity	NPC80641
0.6739	Remote Similarity	NPC154642
0.6735	Remote Similarity	NPC216630
0.6735	Remote Similarity	NPC196924
0.6735	Remote Similarity	NPC171736
0.6735	Remote Similarity	NPC209970
0.6735	Remote Similarity	NPC307783
0.6735	Remote Similarity	NPC149184
0.6731	Remote Similarity	NPC110234
0.6731	Remote Similarity	NPC163751
0.6731	Remote Similarity	NPC326957
0.6731	Remote Similarity	NPC44363
0.6727	Remote Similarity	NPC170167
0.6667	Remote Similarity	NPC320119
0.6667	Remote Similarity	NPC214610
0.6667	Remote Similarity	NPC273545
0.6667	Remote Similarity	NPC477984
0.6667	Remote Similarity	NPC294085
0.6667	Remote Similarity	NPC183424
0.6667	Remote Similarity	NPC57499
0.6667	Remote Similarity	NPC118968
0.6615	Remote Similarity	NPC143396
0.6615	Remote Similarity	NPC296522
0.6615	Remote Similarity	NPC144511
0.6613	Remote Similarity	NPC234767
0.661	Remote Similarity	NPC469373
0.6604	Remote Similarity	NPC106872
0.6604	Remote Similarity	NPC68577
0.66	Remote Similarity	NPC67462
0.6567	Remote Similarity	NPC470237
0.6567	Remote Similarity	NPC326024
0.6567	Remote Similarity	NPC167145
0.6567	Remote Similarity	NPC474705
0.6562	Remote Similarity	NPC60120
0.6557	Remote Similarity	NPC477829
0.6557	Remote Similarity	NPC113293
0.6552	Remote Similarity	NPC327388
0.6552	Remote Similarity	NPC325977
0.6545	Remote Similarity	NPC244452
0.6545	Remote Similarity	NPC48162
0.6522	Remote Similarity	NPC86545
0.6522	Remote Similarity	NPC196442
0.6522	Remote Similarity	NPC301398
0.6522	Remote Similarity	NPC223374

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 NPC216130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	4312
0.2-0.3	3301
0.3-0.4	1056
0.4-0.5	244
0.5-0.6	54
0.6-0.7	18
0.7-0.8	5
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8723	High Similarity	NPD622	Approved
0.8571	High Similarity	NPD29	Approved
0.8571	High Similarity	NPD28	Approved
0.8235	Intermediate Similarity	NPD3172	Approved
0.8077	Intermediate Similarity	NPD3196	Approved
0.8077	Intermediate Similarity	NPD3194	Approved
0.8077	Intermediate Similarity	NPD4266	Approved
0.8077	Intermediate Similarity	NPD3195	Phase 2
0.7917	Intermediate Similarity	NPD3174	Discontinued
0.7451	Intermediate Similarity	NPD3173	Approved
0.7255	Intermediate Similarity	NPD5343	Approved
0.7174	Intermediate Similarity	NPD3206	Approved
0.7167	Intermediate Similarity	NPD3197	Phase 1
0.7021	Intermediate Similarity	NPD633	Phase 3
0.7021	Intermediate Similarity	NPD9448	Phase 2
0.7	Intermediate Similarity	NPD2699	Approved
0.6863	Remote Similarity	NPD4222	Approved
0.6735	Remote Similarity	NPD2270	Approved
0.6667	Remote Similarity	NPD6096	Approved
0.6667	Remote Similarity	NPD9655	Approved
0.6667	Remote Similarity	NPD6097	Approved
0.66	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD39	Approved
0.6406	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD8039	Approved
0.6346	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD634	Phase 3
0.6154	Remote Similarity	NPD5326	Phase 3
0.5972	Remote Similarity	NPD4756	Discovery
0.5965	Remote Similarity	NPD6927	Phase 3
0.5932	Remote Similarity	NPD3728	Approved
0.5932	Remote Similarity	NPD3730	Approved
0.5918	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.589	Remote Similarity	NPD3732	Approved
0.5867	Remote Similarity	NPD5369	Approved
0.5821	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6109	Phase 1
0.5789	Remote Similarity	NPD6435	Approved
0.5733	Remote Similarity	NPD5368	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD5362	Discontinued
0.5692	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD7331	Phase 2
0.5667	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD9431	Approved
0.5636	Remote Similarity	NPD9430	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