NPASS Compound

Structure

CID22101 OpenBabel06191715352D 25 24 0 0 1 0 0 0 0 0999 V2000 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 23 1 6 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.28
Volume:	399.024
LogP:	3.891
LogD:	3.366
LogS:	-3.6
# Rotatable Bonds:	18
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	2.973
Fsp3:	0.762
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.073
MDCK Permeability:	7.464653754141182e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	97.3576431274414%
Volume Distribution (VD):	1.077
Pgp-substrate:	1.717670202255249%

ADMET: Metabolism

CYP1A2-inhibitor:	0.441
CYP1A2-substrate:	0.221
CYP2C19-inhibitor:	0.297
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.406
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.155
CYP2D6-substrate:	0.476
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	6.7
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.236
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.36
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.46
Skin Sensitization:	0.953
Carcinogencity:	0.339
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.496

Download Data

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

Natural Product: NPC22101

Natural Product ID:	NPC22101
*Common Name:**	[(2R)-2,3-Dihydroxypropyl] (9Z,12Z)-Octadeca-9,12-Dienoate
IUPAC Name:	[(2R)-2,3-dihydroxypropyl] (9Z,12Z)-octadeca-9,12-dienoate
Synonyms:
Standard InCHIKey:	WECGLUPZRHILCT-KKFOGOCZSA-N
Standard InCHI:	InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-/t20-/m1/s1
SMILES:	CCCCC/C=CC/C=CCCCCCCCC(=O)OC[C@@H](CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL188186
PubChem CID:	40489139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

*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
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	52000.0	nM	PMID[573541]

☑ 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 NPC22101 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	171
0.1-0.2	1913
0.2-0.3	7396
0.3-0.4	17107
0.4-0.5	8660
0.5-0.6	5789
0.6-0.7	1288
0.7-0.8	312
0.8-0.85	24
0.85-0.9	15
0.9-0.95	7
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271921
1.0	High Similarity	NPC148192
1.0	High Similarity	NPC127091
1.0	High Similarity	NPC104537
1.0	High Similarity	NPC330426
0.9841	High Similarity	NPC48218
0.9841	High Similarity	NPC141481
0.9841	High Similarity	NPC473559
0.9841	High Similarity	NPC324981
0.9683	High Similarity	NPC475443
0.9683	High Similarity	NPC473829
0.9538	High Similarity	NPC476660
0.9385	High Similarity	NPC473772
0.9242	High Similarity	NPC42526
0.9118	High Similarity	NPC474321
0.9062	High Similarity	NPC476657
0.9062	High Similarity	NPC476654
0.9062	High Similarity	NPC476655
0.9048	High Similarity	NPC54925
0.9032	High Similarity	NPC81896
0.9032	High Similarity	NPC321919
0.8923	High Similarity	NPC476659
0.8923	High Similarity	NPC476656
0.8889	High Similarity	NPC321838
0.8889	High Similarity	NPC201939
0.8788	High Similarity	NPC26500
0.8788	High Similarity	NPC99619
0.873	High Similarity	NPC243532
0.8657	High Similarity	NPC273508
0.8657	High Similarity	NPC209327
0.8615	High Similarity	NPC476658
0.8615	High Similarity	NPC68343
0.8615	High Similarity	NPC328089
0.8485	Intermediate Similarity	NPC296436
0.8485	Intermediate Similarity	NPC176215
0.8358	Intermediate Similarity	NPC83965
0.8356	Intermediate Similarity	NPC11796
0.8356	Intermediate Similarity	NPC218817
0.8333	Intermediate Similarity	NPC49392
0.8333	Intermediate Similarity	NPC190400
0.8308	Intermediate Similarity	NPC320305
0.8308	Intermediate Similarity	NPC328776
0.8267	Intermediate Similarity	NPC236649
0.8267	Intermediate Similarity	NPC21693
0.8254	Intermediate Similarity	NPC323436
0.8235	Intermediate Similarity	NPC25298
0.8226	Intermediate Similarity	NPC128061
0.8226	Intermediate Similarity	NPC223677
0.8226	Intermediate Similarity	NPC28779
0.8226	Intermediate Similarity	NPC10316
0.8226	Intermediate Similarity	NPC200845
0.8209	Intermediate Similarity	NPC245947
0.8209	Intermediate Similarity	NPC136164
0.8209	Intermediate Similarity	NPC318420
0.8209	Intermediate Similarity	NPC326268
0.8209	Intermediate Similarity	NPC255863
0.8169	Intermediate Similarity	NPC470435
0.8095	Intermediate Similarity	NPC477201
0.8065	Intermediate Similarity	NPC261831
0.8065	Intermediate Similarity	NPC87564
0.8065	Intermediate Similarity	NPC469937
0.8065	Intermediate Similarity	NPC6095
0.8065	Intermediate Similarity	NPC320588
0.8065	Intermediate Similarity	NPC23155
0.8065	Intermediate Similarity	NPC32467
0.8065	Intermediate Similarity	NPC25417
0.8065	Intermediate Similarity	NPC281972
0.8065	Intermediate Similarity	NPC424
0.8065	Intermediate Similarity	NPC85813
0.8065	Intermediate Similarity	NPC154245
0.8065	Intermediate Similarity	NPC53463
0.8065	Intermediate Similarity	NPC290563
0.8065	Intermediate Similarity	NPC88966
0.806	Intermediate Similarity	NPC470320
0.8052	Intermediate Similarity	NPC473500
0.8052	Intermediate Similarity	NPC470313
0.8052	Intermediate Similarity	NPC38295
0.8052	Intermediate Similarity	NPC156089
0.8	Intermediate Similarity	NPC130618
0.8	Intermediate Similarity	NPC317583
0.8	Intermediate Similarity	NPC469747
0.8	Intermediate Similarity	NPC470436
0.8	Intermediate Similarity	NPC263574
0.7971	Intermediate Similarity	NPC473357
0.7971	Intermediate Similarity	NPC193029
0.7971	Intermediate Similarity	NPC478100
0.7937	Intermediate Similarity	NPC52264
0.7917	Intermediate Similarity	NPC325627
0.7903	Intermediate Similarity	NPC39633
0.7903	Intermediate Similarity	NPC309606
0.7903	Intermediate Similarity	NPC139029
0.7903	Intermediate Similarity	NPC36061
0.7903	Intermediate Similarity	NPC294548
0.7903	Intermediate Similarity	NPC70387
0.7903	Intermediate Similarity	NPC321062
0.7903	Intermediate Similarity	NPC1813
0.7903	Intermediate Similarity	NPC139545
0.7903	Intermediate Similarity	NPC71761
0.7895	Intermediate Similarity	NPC103634
0.7895	Intermediate Similarity	NPC200446
0.7879	Intermediate Similarity	NPC229252
0.7879	Intermediate Similarity	NPC143857
0.7838	Intermediate Similarity	NPC470899
0.7826	Intermediate Similarity	NPC478101
0.7821	Intermediate Similarity	NPC253801
0.7821	Intermediate Similarity	NPC178758
0.7821	Intermediate Similarity	NPC196102
0.7812	Intermediate Similarity	NPC18951
0.7794	Intermediate Similarity	NPC226592
0.7778	Intermediate Similarity	NPC137538
0.7778	Intermediate Similarity	NPC320119
0.7763	Intermediate Similarity	NPC209995
0.7761	Intermediate Similarity	NPC113293
0.7746	Intermediate Similarity	NPC143396
0.7742	Intermediate Similarity	NPC281245
0.7742	Intermediate Similarity	NPC92114
0.7733	Intermediate Similarity	NPC110813
0.7727	Intermediate Similarity	NPC274927
0.7727	Intermediate Similarity	NPC106851
0.7722	Intermediate Similarity	NPC163093
0.7714	Intermediate Similarity	NPC478097
0.7692	Intermediate Similarity	NPC211752
0.7692	Intermediate Similarity	NPC473780
0.7692	Intermediate Similarity	NPC323597
0.7692	Intermediate Similarity	NPC323498
0.7692	Intermediate Similarity	NPC65930
0.7692	Intermediate Similarity	NPC180363
0.7692	Intermediate Similarity	NPC145914
0.7692	Intermediate Similarity	NPC473529
0.7692	Intermediate Similarity	NPC94875
0.7692	Intermediate Similarity	NPC474252
0.7692	Intermediate Similarity	NPC131002
0.7692	Intermediate Similarity	NPC11332
0.7692	Intermediate Similarity	NPC73310
0.7692	Intermediate Similarity	NPC475159
0.7692	Intermediate Similarity	NPC329829
0.7692	Intermediate Similarity	NPC473712
0.7671	Intermediate Similarity	NPC326024
0.7656	Intermediate Similarity	NPC228473
0.7647	Intermediate Similarity	NPC29697
0.7632	Intermediate Similarity	NPC133377
0.7632	Intermediate Similarity	NPC469495
0.7625	Intermediate Similarity	NPC477014
0.7625	Intermediate Similarity	NPC120398
0.7625	Intermediate Similarity	NPC475206
0.7625	Intermediate Similarity	NPC471567
0.7625	Intermediate Similarity	NPC322529
0.7625	Intermediate Similarity	NPC477013
0.7612	Intermediate Similarity	NPC327112
0.7612	Intermediate Similarity	NPC328311
0.7595	Intermediate Similarity	NPC144415
0.7581	Intermediate Similarity	NPC262968
0.7568	Intermediate Similarity	NPC227396
0.7538	Intermediate Similarity	NPC187777
0.7538	Intermediate Similarity	NPC327388
0.7538	Intermediate Similarity	NPC179764
0.7531	Intermediate Similarity	NPC279267
0.7531	Intermediate Similarity	NPC69082
0.7531	Intermediate Similarity	NPC477015
0.7531	Intermediate Similarity	NPC309211
0.75	Intermediate Similarity	NPC325929
0.75	Intermediate Similarity	NPC9868
0.75	Intermediate Similarity	NPC477829
0.75	Intermediate Similarity	NPC156804
0.75	Intermediate Similarity	NPC66460
0.75	Intermediate Similarity	NPC40082
0.75	Intermediate Similarity	NPC271282
0.747	Intermediate Similarity	NPC39290
0.747	Intermediate Similarity	NPC159369
0.7467	Intermediate Similarity	NPC473948
0.7463	Intermediate Similarity	NPC470363
0.7439	Intermediate Similarity	NPC178215
0.7436	Intermediate Similarity	NPC47653
0.7429	Intermediate Similarity	NPC478099
0.7429	Intermediate Similarity	NPC478098
0.7424	Intermediate Similarity	NPC225929
0.7419	Intermediate Similarity	NPC59051
0.7419	Intermediate Similarity	NPC224227
0.7407	Intermediate Similarity	NPC329615
0.7407	Intermediate Similarity	NPC235809
0.7407	Intermediate Similarity	NPC319036
0.7407	Intermediate Similarity	NPC82795
0.7407	Intermediate Similarity	NPC107986
0.7407	Intermediate Similarity	NPC283085
0.7407	Intermediate Similarity	NPC1083
0.7407	Intermediate Similarity	NPC473669
0.7407	Intermediate Similarity	NPC110710
0.7407	Intermediate Similarity	NPC473671
0.7407	Intermediate Similarity	NPC39167
0.7407	Intermediate Similarity	NPC286338
0.7407	Intermediate Similarity	NPC475268
0.7407	Intermediate Similarity	NPC473156
0.7407	Intermediate Similarity	NPC103284
0.7407	Intermediate Similarity	NPC39279
0.7407	Intermediate Similarity	NPC25764
0.7407	Intermediate Similarity	NPC223871
0.7407	Intermediate Similarity	NPC77871
0.7407	Intermediate Similarity	NPC66346
0.7407	Intermediate Similarity	NPC202055
0.7407	Intermediate Similarity	NPC329838

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 NPC22101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	2709
0.2-0.3	3702
0.3-0.4	1745
0.4-0.5	624
0.5-0.6	175
0.6-0.7	41
0.7-0.8	18
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD3197	Phase 1
0.8065	Intermediate Similarity	NPD3195	Phase 2
0.8065	Intermediate Similarity	NPD3194	Approved
0.8065	Intermediate Similarity	NPD3196	Approved
0.8065	Intermediate Similarity	NPD3730	Approved
0.8065	Intermediate Similarity	NPD4266	Approved
0.8065	Intermediate Similarity	NPD3728	Approved
0.7903	Intermediate Similarity	NPD3172	Approved
0.7846	Intermediate Similarity	NPD6109	Phase 1
0.7612	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD28	Approved
0.7581	Intermediate Similarity	NPD29	Approved
0.7468	Intermediate Similarity	NPD6435	Approved
0.7375	Intermediate Similarity	NPD7154	Phase 3
0.7294	Intermediate Similarity	NPD7983	Approved
0.7258	Intermediate Similarity	NPD3173	Approved
0.7222	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5368	Approved
0.7176	Intermediate Similarity	NPD6698	Approved
0.7176	Intermediate Similarity	NPD46	Approved
0.7125	Intermediate Similarity	NPD5369	Approved
0.7097	Intermediate Similarity	NPD622	Approved
0.7097	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5343	Approved
0.6962	Remote Similarity	NPD4268	Approved
0.6962	Remote Similarity	NPD4271	Approved
0.6962	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5362	Discontinued
0.686	Remote Similarity	NPD6101	Approved
0.686	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4269	Approved
0.6829	Remote Similarity	NPD4270	Approved
0.679	Remote Similarity	NPD4821	Approved
0.679	Remote Similarity	NPD4819	Approved
0.679	Remote Similarity	NPD4822	Approved
0.679	Remote Similarity	NPD4820	Approved
0.679	Remote Similarity	NPD4252	Approved
0.6774	Remote Similarity	NPD4222	Approved
0.6774	Remote Similarity	NPD39	Approved
0.6774	Remote Similarity	NPD3174	Discontinued
0.675	Remote Similarity	NPD3732	Approved
0.6706	Remote Similarity	NPD5786	Approved
0.6705	Remote Similarity	NPD6411	Approved
0.6629	Remote Similarity	NPD5779	Approved
0.6629	Remote Similarity	NPD5778	Approved
0.6628	Remote Similarity	NPD4251	Approved
0.6628	Remote Similarity	NPD4250	Approved
0.6613	Remote Similarity	NPD6097	Approved
0.6613	Remote Similarity	NPD2699	Approved
0.6613	Remote Similarity	NPD6096	Approved
0.6591	Remote Similarity	NPD7838	Discovery
0.6588	Remote Similarity	NPD5363	Approved
0.6512	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5326	Phase 3
0.642	Remote Similarity	NPD4756	Discovery
0.6413	Remote Similarity	NPD7839	Suspended
0.6404	Remote Similarity	NPD5785	Approved
0.64	Remote Similarity	NPD3704	Approved
0.6375	Remote Similarity	NPD8039	Approved
0.6353	Remote Similarity	NPD5332	Approved
0.6353	Remote Similarity	NPD5331	Approved
0.6322	Remote Similarity	NPD6422	Discontinued
0.631	Remote Similarity	NPD4790	Discontinued
0.6296	Remote Similarity	NPD818	Approved
0.6296	Remote Similarity	NPD819	Approved
0.6292	Remote Similarity	NPD5370	Suspended
0.6216	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7331	Phase 2
0.6184	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7909	Approved
0.6129	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2270	Approved
0.6111	Remote Similarity	NPD585	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6686	Approved
0.6087	Remote Similarity	NPD6399	Phase 3
0.6078	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6927	Phase 3
0.6023	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.598	Remote Similarity	NPD6371	Approved
0.598	Remote Similarity	NPD6421	Discontinued
0.5978	Remote Similarity	NPD7515	Phase 2
0.5978	Remote Similarity	NPD7637	Suspended
0.5938	Remote Similarity	NPD4225	Approved
0.5938	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD8297	Approved
0.5846	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6412	Phase 2
0.5833	Remote Similarity	NPD7902	Approved
0.5816	Remote Similarity	NPD5344	Discontinued
0.5814	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD3198	Approved
0.5806	Remote Similarity	NPD9448	Phase 2
0.5806	Remote Similarity	NPD633	Phase 3
0.5806	Remote Similarity	NPD9655	Approved
0.5795	Remote Similarity	NPD6110	Phase 1
0.5794	Remote Similarity	NPD6935	Phase 3
0.5794	Remote Similarity	NPD7115	Discovery
0.5794	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5695	Phase 3
0.5784	Remote Similarity	NPD6881	Approved
0.5784	Remote Similarity	NPD6899	Approved
0.5778	Remote Similarity	NPD7521	Approved
0.5778	Remote Similarity	NPD6684	Approved
0.5778	Remote Similarity	NPD7334	Approved
0.5778	Remote Similarity	NPD7146	Approved
0.5778	Remote Similarity	NPD6409	Approved
0.5778	Remote Similarity	NPD5330	Approved
0.575	Remote Similarity	NPD8277	Approved
0.5743	Remote Similarity	NPD6675	Approved
0.5743	Remote Similarity	NPD6402	Approved
0.5743	Remote Similarity	NPD5739	Approved
0.5743	Remote Similarity	NPD7128	Approved
0.5741	Remote Similarity	NPD6918	Phase 1
0.5741	Remote Similarity	NPD7641	Discontinued
0.573	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.573	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD7536	Approved
0.5714	Remote Similarity	NPD7798	Approved
0.5699	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5697	Approved
0.5684	Remote Similarity	NPD5282	Discontinued
0.5682	Remote Similarity	NPD3667	Approved
0.5682	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD5209	Approved
0.5673	Remote Similarity	NPD6883	Approved
0.5673	Remote Similarity	NPD7102	Approved
0.5673	Remote Similarity	NPD7290	Approved
0.5652	Remote Similarity	NPD6903	Approved
0.5652	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6672	Approved
0.5652	Remote Similarity	NPD5737	Approved
0.5645	Remote Similarity	NPD3206	Approved
0.5641	Remote Similarity	NPD7341	Phase 2
0.5631	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7320	Approved
0.5625	Remote Similarity	NPD8278	Approved
0.5619	Remote Similarity	NPD8130	Phase 1
0.5619	Remote Similarity	NPD6650	Approved
0.5619	Remote Similarity	NPD6869	Approved
0.5619	Remote Similarity	NPD6847	Approved
0.5619	Remote Similarity	NPD6617	Approved
0.5619	Remote Similarity	NPD6649	Approved
0.5616	Remote Similarity	NPD73	Approved
0.5612	Remote Similarity	NPD5696	Approved
0.5612	Remote Similarity	NPD7638	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