NPASS Compound

Structure

NPC120398 OpenBabel07101718192D 46 47 0 0 1 0 0 0 0 0999 V2000 8.0532 -7.9097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.7033 1.7043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7442 -6.9586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4134 -6.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3915 -6.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0606 -5.6803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0388 -5.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7079 -5.1450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7769 -0.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6904 0.0327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9678 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4994 -0.5551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6861 -5.3529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0543 -0.1930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4130 -0.1483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3552 -4.6098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2453 0.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2220 -0.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3333 -4.8177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3317 -0.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1355 -0.3294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0025 -4.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5227 0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9445 -0.9172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.9806 -4.2825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.9285 -1.7793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.3407 -0.9702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6671 -1.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 15.5987 0.7098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8581 -0.5104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 16.6497 -3.5393 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 16.3407 -2.5883 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.3897 -1.2793 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.5807 -0.6915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4077 0.1220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9626 0.4841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 17.6279 -3.7472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 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 14.6852 0.3030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.3897 -2.2793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 3 32 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 28 1 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 31 1 0 0 0 0 29 33 2 0 0 0 0 30 34 1 0 0 0 0 31 2 1 6 0 0 0 31 44 1 0 0 0 0 32 40 2 0 0 0 0 32 45 1 0 0 0 0 33 39 1 0 0 0 0 34 41 1 1 0 0 0 35 42 1 1 0 0 0 36 35 1 6 0 0 0 36 46 1 0 0 0 0 37 38 1 1 0 0 0 37 46 1 0 0 0 0 38 30 1 1 0 0 0 38 45 1 0 0 0 0 39 43 2 0 0 0 0 39 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	650.51
Volume:	719.609
LogP:	10.756
LogD:	5.095
LogS:	-6.546
# Rotatable Bonds:	30
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.058
Synthetic Accessibility Score:	4.435
Fsp3:	0.872
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.188
MDCK Permeability:	5.086577402835246e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.897
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	98.20985412597656%
Volume Distribution (VD):	1.762
Pgp-substrate:	1.8471630811691284%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.214
CYP3A4-substrate:	0.033

ADMET: Excretion

Clearance (CL):	3.383
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.679
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.671
Skin Sensitization:	0.976
Carcinogencity:	0.026
Eye Corrosion:	0.004
Eye Irritation:	0.058
Respiratory Toxicity:	0.367

Download Data

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

Natural Product: NPC120398

Natural Product ID:	NPC120398
*Common Name:**	Calamistrin B
IUPAC Name:	[(1R,3R)-3-hydroxy-1-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]-15-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]pentadecyl] acetate
Synonyms:
Standard InCHIKey:	FPQIHOHGIGXPEO-AZSLXLSQSA-N
Standard InCHI:	InChI=1S/C39H70O7/c1-4-5-6-7-8-9-14-17-20-23-26-35(42)36-27-28-37(46-36)38(45-32(3)40)30-34(41)25-22-19-16-13-11-10-12-15-18-21-24-33-29-31(2)44-39(33)43/h29,31,34-38,41-42H,4-28,30H2,1-3H3/t31-,34+,35-,36+,37+,38+/m0/s1
SMILES:	CCCCCCCCCCCC[C@@H]([C@H]1CC[C@@H](O1)[C@H](OC(=O)C)C[C@@H](CCCCCCCCCCCCC1=C[C@@H](OC1=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504679
PubChem CID:	10416831
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO210	Uvaria calamistrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075755]
NPO210	Uvaria calamistrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000019]
NPO210	Uvaria calamistrata	Species	Annonaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.1	ug.mL-1	PMID[449674]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	3.1	ug.mL-1	PMID[449674]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	0.022	ug.mL-1	PMID[449674]

☑ 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 NPC120398 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	179
0.1-0.2	1415
0.2-0.3	5597
0.3-0.4	13333
0.4-0.5	11399
0.5-0.6	7013
0.6-0.7	2939
0.7-0.8	625
0.8-0.85	24
0.85-0.9	21
0.9-0.95	105
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471567
0.9873	High Similarity	NPC163093
0.9873	High Similarity	NPC156804
0.975	High Similarity	NPC329615
0.975	High Similarity	NPC322529
0.975	High Similarity	NPC477014
0.975	High Similarity	NPC477013
0.975	High Similarity	NPC329838
0.9634	High Similarity	NPC48338
0.9634	High Similarity	NPC21208
0.9634	High Similarity	NPC40376
0.9634	High Similarity	NPC280621
0.9634	High Similarity	NPC233551
0.9634	High Similarity	NPC473905
0.9634	High Similarity	NPC20339
0.9634	High Similarity	NPC89001
0.9634	High Similarity	NPC320458
0.963	High Similarity	NPC107717
0.963	High Similarity	NPC232555
0.963	High Similarity	NPC171174
0.963	High Similarity	NPC241360
0.963	High Similarity	NPC475581
0.963	High Similarity	NPC231096
0.963	High Similarity	NPC62118
0.963	High Similarity	NPC114694
0.963	High Similarity	NPC477015
0.963	High Similarity	NPC142117
0.963	High Similarity	NPC293136
0.963	High Similarity	NPC132940
0.963	High Similarity	NPC240695
0.962	High Similarity	NPC11332
0.962	High Similarity	NPC131002
0.962	High Similarity	NPC329829
0.962	High Similarity	NPC65930
0.962	High Similarity	NPC473712
0.962	High Similarity	NPC73310
0.962	High Similarity	NPC145914
0.962	High Similarity	NPC473780
0.962	High Similarity	NPC180363
0.962	High Similarity	NPC475159
0.962	High Similarity	NPC94875
0.962	High Similarity	NPC473529
0.9518	High Similarity	NPC477017
0.9518	High Similarity	NPC477016
0.9512	High Similarity	NPC258068
0.9512	High Similarity	NPC20533
0.9512	High Similarity	NPC178215
0.9512	High Similarity	NPC476583
0.9506	High Similarity	NPC473478
0.9506	High Similarity	NPC292809
0.9506	High Similarity	NPC283085
0.9506	High Similarity	NPC103284
0.9506	High Similarity	NPC475268
0.9506	High Similarity	NPC202055
0.9506	High Similarity	NPC231009
0.9506	High Similarity	NPC39167
0.9506	High Similarity	NPC477018
0.9506	High Similarity	NPC100921
0.9506	High Similarity	NPC286338
0.9506	High Similarity	NPC223871
0.9506	High Similarity	NPC473651
0.9506	High Similarity	NPC39279
0.9506	High Similarity	NPC9678
0.9506	High Similarity	NPC473669
0.9506	High Similarity	NPC110710
0.9506	High Similarity	NPC66346
0.9506	High Similarity	NPC132496
0.9506	High Similarity	NPC235809
0.9506	High Similarity	NPC107986
0.9506	High Similarity	NPC319036
0.9506	High Similarity	NPC25764
0.9506	High Similarity	NPC473156
0.9506	High Similarity	NPC77871
0.9506	High Similarity	NPC470400
0.9506	High Similarity	NPC82795
0.9506	High Similarity	NPC473671
0.9506	High Similarity	NPC1083
0.95	High Similarity	NPC253801
0.95	High Similarity	NPC144415
0.9405	High Similarity	NPC239517
0.9398	High Similarity	NPC287164
0.9398	High Similarity	NPC61257
0.9398	High Similarity	NPC133730
0.9398	High Similarity	NPC169511
0.9398	High Similarity	NPC234077
0.9398	High Similarity	NPC172821
0.9398	High Similarity	NPC151403
0.9398	High Similarity	NPC171135
0.9398	High Similarity	NPC242364
0.9398	High Similarity	NPC39754
0.9398	High Similarity	NPC320569
0.9398	High Similarity	NPC81045
0.9398	High Similarity	NPC191929
0.9398	High Similarity	NPC274446
0.9398	High Similarity	NPC261952
0.9398	High Similarity	NPC100454
0.939	High Similarity	NPC309211
0.939	High Similarity	NPC219652
0.939	High Similarity	NPC210218
0.939	High Similarity	NPC69082
0.939	High Similarity	NPC103523
0.939	High Similarity	NPC25703
0.939	High Similarity	NPC477010
0.939	High Similarity	NPC134885
0.939	High Similarity	NPC308412
0.939	High Similarity	NPC473687
0.939	High Similarity	NPC204686
0.939	High Similarity	NPC134865
0.939	High Similarity	NPC134807
0.939	High Similarity	NPC473840
0.939	High Similarity	NPC282815
0.939	High Similarity	NPC279267
0.939	High Similarity	NPC219498
0.9286	High Similarity	NPC477011
0.9286	High Similarity	NPC473504
0.9286	High Similarity	NPC42598
0.9286	High Similarity	NPC93794
0.9286	High Similarity	NPC40066
0.9286	High Similarity	NPC318963
0.9286	High Similarity	NPC91067
0.9286	High Similarity	NPC81778
0.9286	High Similarity	NPC20621
0.9286	High Similarity	NPC280612
0.9277	High Similarity	NPC473995
0.9277	High Similarity	NPC470401
0.9277	High Similarity	NPC154097
0.9277	High Similarity	NPC159750
0.9277	High Similarity	NPC473649
0.9176	High Similarity	NPC473904
0.9157	High Similarity	NPC47937
0.9157	High Similarity	NPC112685
0.9059	High Similarity	NPC14901
0.9059	High Similarity	NPC130359
0.9059	High Similarity	NPC139418
0.9048	High Similarity	NPC477012
0.9036	High Similarity	NPC182383
0.8966	High Similarity	NPC473723
0.8966	High Similarity	NPC473663
0.8966	High Similarity	NPC473561
0.8966	High Similarity	NPC473520
0.8966	High Similarity	NPC475173
0.8851	High Similarity	NPC473707
0.875	High Similarity	NPC11456
0.8315	Intermediate Similarity	NPC473619
0.8315	Intermediate Similarity	NPC473448
0.8222	Intermediate Similarity	NPC184463
0.8222	Intermediate Similarity	NPC30515
0.8222	Intermediate Similarity	NPC473321
0.8152	Intermediate Similarity	NPC36954
0.8132	Intermediate Similarity	NPC475912
0.8132	Intermediate Similarity	NPC476300
0.8132	Intermediate Similarity	NPC81419
0.8132	Intermediate Similarity	NPC179746
0.8132	Intermediate Similarity	NPC273579
0.8132	Intermediate Similarity	NPC162205
0.8132	Intermediate Similarity	NPC295204
0.8132	Intermediate Similarity	NPC288240
0.8125	Intermediate Similarity	NPC84038
0.8111	Intermediate Similarity	NPC474761
0.8111	Intermediate Similarity	NPC476004
0.8111	Intermediate Similarity	NPC51004
0.8095	Intermediate Similarity	NPC470148
0.8095	Intermediate Similarity	NPC470149
0.8085	Intermediate Similarity	NPC187268
0.8085	Intermediate Similarity	NPC473326
0.8072	Intermediate Similarity	NPC475711
0.8068	Intermediate Similarity	NPC469483
0.8046	Intermediate Similarity	NPC288471
0.8025	Intermediate Similarity	NPC474705
0.8022	Intermediate Similarity	NPC12172
0.8022	Intermediate Similarity	NPC208886
0.8	Intermediate Similarity	NPC307411
0.8	Intermediate Similarity	NPC295312
0.8	Intermediate Similarity	NPC470147
0.8	Intermediate Similarity	NPC133226
0.8	Intermediate Similarity	NPC47653
0.7976	Intermediate Similarity	NPC248775
0.7957	Intermediate Similarity	NPC14961
0.7957	Intermediate Similarity	NPC270013
0.7955	Intermediate Similarity	NPC21469
0.7935	Intermediate Similarity	NPC212486
0.7931	Intermediate Similarity	NPC284472
0.7931	Intermediate Similarity	NPC286770
0.7931	Intermediate Similarity	NPC229799
0.7931	Intermediate Similarity	NPC475947
0.7889	Intermediate Similarity	NPC202672
0.7889	Intermediate Similarity	NPC473715
0.7882	Intermediate Similarity	NPC180725
0.7872	Intermediate Similarity	NPC477921
0.7872	Intermediate Similarity	NPC476315
0.7872	Intermediate Similarity	NPC279621
0.7865	Intermediate Similarity	NPC164393
0.7857	Intermediate Similarity	NPC474026
0.7849	Intermediate Similarity	NPC81386
0.7849	Intermediate Similarity	NPC474035
0.7835	Intermediate Similarity	NPC86077
0.7826	Intermediate Similarity	NPC327760
0.7816	Intermediate Similarity	NPC474959
0.7816	Intermediate Similarity	NPC11383
0.7816	Intermediate Similarity	NPC310450

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 NPC120398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2188
0.2-0.3	3833
0.3-0.4	2058
0.4-0.5	603
0.5-0.6	252
0.6-0.7	50
0.7-0.8	4
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
0.8111	Intermediate Similarity	NPD6698	Approved
0.8111	Intermediate Similarity	NPD46	Approved
0.7717	Intermediate Similarity	NPD7838	Discovery
0.77	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6686	Approved
0.7447	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD6371	Approved
0.7021	Intermediate Similarity	NPD4251	Approved
0.7021	Intermediate Similarity	NPD4250	Approved
0.7	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4249	Approved
0.6869	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3197	Phase 1
0.6774	Remote Similarity	NPD7154	Phase 3
0.6701	Remote Similarity	NPD1695	Approved
0.6699	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD4225	Approved
0.6633	Remote Similarity	NPD5785	Approved
0.6632	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5362	Discontinued
0.6574	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6053	Discontinued
0.6505	Remote Similarity	NPD7638	Approved
0.6489	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6435	Approved
0.6484	Remote Similarity	NPD4756	Discovery
0.6458	Remote Similarity	NPD5363	Approved
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6441	Remote Similarity	NPD7507	Approved
0.6413	Remote Similarity	NPD4271	Approved
0.6413	Remote Similarity	NPD4268	Approved
0.6395	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8516	Approved
0.6379	Remote Similarity	NPD8513	Phase 3
0.6379	Remote Similarity	NPD8517	Approved
0.6379	Remote Similarity	NPD8515	Approved
0.6354	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD5778	Approved
0.6329	Remote Similarity	NPD3728	Approved
0.6329	Remote Similarity	NPD3730	Approved
0.6311	Remote Similarity	NPD7839	Suspended
0.6286	Remote Similarity	NPD6648	Approved
0.6281	Remote Similarity	NPD7319	Approved
0.6277	Remote Similarity	NPD4819	Approved
0.6277	Remote Similarity	NPD4822	Approved
0.6277	Remote Similarity	NPD4821	Approved
0.6277	Remote Similarity	NPD4820	Approved
0.6277	Remote Similarity	NPD5368	Approved
0.6275	Remote Similarity	NPD5282	Discontinued
0.6271	Remote Similarity	NPD7829	Approved
0.6271	Remote Similarity	NPD7830	Approved
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD6110	Phase 1
0.6239	Remote Similarity	NPD6412	Phase 2
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7115	Discovery
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8294	Approved
0.6154	Remote Similarity	NPD8377	Approved
0.6146	Remote Similarity	NPD4269	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6146	Remote Similarity	NPD4270	Approved
0.6125	Remote Similarity	NPD4266	Approved
0.6125	Remote Similarity	NPD3194	Approved
0.6125	Remote Similarity	NPD3195	Phase 2
0.6125	Remote Similarity	NPD3196	Approved
0.6122	Remote Similarity	NPD1694	Approved
0.6121	Remote Similarity	NPD7327	Approved
0.6121	Remote Similarity	NPD7328	Approved
0.6116	Remote Similarity	NPD8074	Phase 3
0.6105	Remote Similarity	NPD4252	Approved
0.6102	Remote Similarity	NPD8033	Approved
0.6102	Remote Similarity	NPD8296	Approved
0.6102	Remote Similarity	NPD8380	Approved
0.6102	Remote Similarity	NPD8335	Approved
0.6102	Remote Similarity	NPD8379	Approved
0.6102	Remote Similarity	NPD8378	Approved
0.6082	Remote Similarity	NPD5332	Approved
0.6082	Remote Similarity	NPD5331	Approved
0.6068	Remote Similarity	NPD7516	Approved
0.6063	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5786	Approved
0.6042	Remote Similarity	NPD5369	Approved
0.6042	Remote Similarity	NPD4790	Discontinued
0.6024	Remote Similarity	NPD69	Approved
0.6024	Remote Similarity	NPD6109	Phase 1
0.6024	Remote Similarity	NPD9119	Approved
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD7642	Approved
0.5983	Remote Similarity	NPD7641	Discontinued
0.5966	Remote Similarity	NPD8444	Approved
0.5965	Remote Similarity	NPD8297	Approved
0.595	Remote Similarity	NPD7492	Approved
0.5949	Remote Similarity	NPD6927	Phase 3
0.5946	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7736	Approved
0.593	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6421	Discontinued
0.5922	Remote Similarity	NPD7637	Suspended
0.5913	Remote Similarity	NPD8133	Approved
0.5913	Remote Similarity	NPD4632	Approved
0.5909	Remote Similarity	NPD3704	Approved
0.5904	Remote Similarity	NPD9118	Approved
0.5902	Remote Similarity	NPD6616	Approved
0.5902	Remote Similarity	NPD8273	Phase 1
0.5882	Remote Similarity	NPD6101	Approved
0.5882	Remote Similarity	NPD6319	Approved
0.5882	Remote Similarity	NPD6054	Approved
0.5882	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD2204	Approved
0.5872	Remote Similarity	NPD7632	Discontinued
0.5854	Remote Similarity	NPD8293	Discontinued
0.5854	Remote Similarity	NPD7078	Approved
0.5833	Remote Similarity	NPD7503	Approved
0.581	Remote Similarity	NPD7748	Approved
0.5794	Remote Similarity	NPD6083	Phase 2
0.5794	Remote Similarity	NPD6084	Phase 2
0.5794	Remote Similarity	NPD7902	Approved
0.5785	Remote Similarity	NPD6370	Approved
0.5772	Remote Similarity	NPD8451	Approved
0.5769	Remote Similarity	NPD6411	Approved
0.5763	Remote Similarity	NPD7505	Discontinued
0.5763	Remote Similarity	NPD7500	Approved
0.5752	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6881	Approved
0.5752	Remote Similarity	NPD7320	Approved
0.5752	Remote Similarity	NPD6899	Approved
0.575	Remote Similarity	NPD6059	Approved
0.575	Remote Similarity	NPD29	Approved
0.575	Remote Similarity	NPD28	Approved
0.5739	Remote Similarity	NPD8130	Phase 1
0.5739	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8328	Phase 3
0.573	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.573	Remote Similarity	NPD7331	Phase 2
0.5728	Remote Similarity	NPD5370	Suspended
0.5726	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5702	Remote Similarity	NPD6015	Approved
0.5702	Remote Similarity	NPD6016	Approved
0.5702	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6647	Phase 2
0.5673	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD7260	Phase 2
0.5664	Remote Similarity	NPD5697	Approved
0.5656	Remote Similarity	NPD5988	Approved
0.5656	Remote Similarity	NPD8080	Discontinued
0.5652	Remote Similarity	NPD2067	Discontinued
0.5652	Remote Similarity	NPD7290	Approved
0.5652	Remote Similarity	NPD6883	Approved
0.5652	Remote Similarity	NPD7102	Approved
0.5631	Remote Similarity	NPD6903	Approved
0.563	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6009	Approved
0.5625	Remote Similarity	NPD6845	Suspended
0.5619	Remote Similarity	NPD7515	Phase 2
0.5619	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.561	Remote Similarity	NPD7604	Phase 2
0.5607	Remote Similarity	NPD5695	Phase 3
0.5603	Remote Similarity	NPD6650	Approved
0.5603	Remote Similarity	NPD6649	Approved
0.5603	Remote Similarity	NPD6617	Approved
0.5603	Remote Similarity	NPD6869	Approved
0.5603	Remote Similarity	NPD6847	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