NPASS Compound

Structure

NPC163093 OpenBabel07101718322D 43 44 0 0 1 0 0 0 0 0999 V2000 6.7661 -6.7507 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 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 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 1 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 14.5807 -0.6915 0.0000 C 0 0 2 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 0.7431 0.6691 0.0000 C 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 14.6852 0.3030 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 15.3897 -2.2793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 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 1 0 0 0 0 7 8 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 14 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 31 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 27 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 30 1 0 0 0 0 28 31 2 0 0 0 0 29 32 1 0 0 0 0 29 34 1 0 0 0 0 30 2 1 6 0 0 0 30 42 1 0 0 0 0 31 37 1 0 0 0 0 32 38 1 6 0 0 0 33 39 1 1 0 0 0 34 40 1 1 0 0 0 35 33 1 6 0 0 0 35 43 1 0 0 0 0 36 34 1 1 0 0 0 36 43 1 0 0 0 0 37 41 2 0 0 0 0 37 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.5
Volume:	678.863
LogP:	10.355
LogD:	5.109
LogS:	-5.828
# Rotatable Bonds:	28
TPSA:	103.29
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.071
Synthetic Accessibility Score:	4.322
Fsp3:	0.892
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:	-5.268
MDCK Permeability:	7.450153134413995e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	98.05079650878906%
Volume Distribution (VD):	1.709
Pgp-substrate:	1.8595678806304932%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	4.91
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.395
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.975
Carcinogencity:	0.023
Eye Corrosion:	0.005
Eye Irritation:	0.085
Respiratory Toxicity:	0.627

Download Data

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

Natural Product: NPC163093

Natural Product ID:	NPC163093
*Common Name:**	Calamistrin A
IUPAC Name:	(2S)-4-[(13S,15R)-13,15-dihydroxy-15-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-2-methyl-2H-furan-5-one
Synonyms:
Standard InCHIKey:	ADPAPZVYVYEBGS-WJTSKZNASA-N
Standard InCHI:	InChI=1S/C37H68O6/c1-3-4-5-6-7-8-13-16-19-22-25-33(39)35-26-27-36(43-35)34(40)29-32(38)24-21-18-15-12-10-9-11-14-17-20-23-31-28-30(2)42-37(31)41/h28,30,32-36,38-40H,3-27,29H2,1-2H3/t30-,32-,33-,34+,35+,36+/m0/s1
SMILES:	CCCCCCCCCCCC[C@@H]([C@H]1CC[C@@H](O1)[C@@H](C[C@H](CCCCCCCCCCCCC1=C[C@@H](OC1=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506094
PubChem CID:	9986162
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	=	2.0	ug.mL-1	PMID[530439]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1.4	ug.mL-1	PMID[530439]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	0.37	ug.mL-1	PMID[530439]

☑ 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 NPC163093 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	174
0.1-0.2	1388
0.2-0.3	5600
0.3-0.4	14069
0.4-0.5	10809
0.5-0.6	7016
0.6-0.7	2843
0.7-0.8	609
0.8-0.85	16
0.85-0.9	32
0.9-0.95	91
0.95-1	50

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC477014
0.9873	High Similarity	NPC471567
0.9873	High Similarity	NPC120398
0.9873	High Similarity	NPC477013
0.975	High Similarity	NPC477015
0.9747	High Similarity	NPC156804
0.9744	High Similarity	NPC473529
0.9744	High Similarity	NPC329829
0.9744	High Similarity	NPC94875
0.9744	High Similarity	NPC473780
0.9744	High Similarity	NPC475159
0.9744	High Similarity	NPC11332
0.9744	High Similarity	NPC180363
0.9744	High Similarity	NPC131002
0.9744	High Similarity	NPC473712
0.9744	High Similarity	NPC145914
0.9744	High Similarity	NPC73310
0.9744	High Similarity	NPC65930
0.963	High Similarity	NPC178215
0.9625	High Similarity	NPC473651
0.9625	High Similarity	NPC82795
0.9625	High Similarity	NPC223871
0.9625	High Similarity	NPC329615
0.9625	High Similarity	NPC132496
0.9625	High Similarity	NPC107986
0.9625	High Similarity	NPC329838
0.9625	High Similarity	NPC103284
0.9625	High Similarity	NPC231009
0.9625	High Similarity	NPC286338
0.9625	High Similarity	NPC322529
0.9625	High Similarity	NPC473478
0.9625	High Similarity	NPC283085
0.9625	High Similarity	NPC66346
0.9625	High Similarity	NPC110710
0.9625	High Similarity	NPC1083
0.9625	High Similarity	NPC473669
0.962	High Similarity	NPC144415
0.962	High Similarity	NPC253801
0.9512	High Similarity	NPC40376
0.9512	High Similarity	NPC20339
0.9512	High Similarity	NPC320458
0.9512	High Similarity	NPC89001
0.9512	High Similarity	NPC473905
0.9512	High Similarity	NPC233551
0.9512	High Similarity	NPC21208
0.9512	High Similarity	NPC280621
0.9512	High Similarity	NPC48338
0.9506	High Similarity	NPC107717
0.9506	High Similarity	NPC232555
0.9506	High Similarity	NPC171174
0.9506	High Similarity	NPC308412
0.9506	High Similarity	NPC204686
0.9506	High Similarity	NPC134865
0.9506	High Similarity	NPC473687
0.9506	High Similarity	NPC114694
0.9506	High Similarity	NPC240695
0.9506	High Similarity	NPC134807
0.9506	High Similarity	NPC279267
0.9506	High Similarity	NPC210218
0.9506	High Similarity	NPC293136
0.9506	High Similarity	NPC62118
0.9506	High Similarity	NPC134885
0.9506	High Similarity	NPC241360
0.9506	High Similarity	NPC69082
0.9506	High Similarity	NPC231096
0.9506	High Similarity	NPC103523
0.9506	High Similarity	NPC219498
0.9506	High Similarity	NPC132940
0.9506	High Similarity	NPC142117
0.9506	High Similarity	NPC475581
0.9398	High Similarity	NPC280612
0.9398	High Similarity	NPC477016
0.9398	High Similarity	NPC477017
0.939	High Similarity	NPC476583
0.939	High Similarity	NPC258068
0.939	High Similarity	NPC20533
0.9383	High Similarity	NPC25764
0.9383	High Similarity	NPC477018
0.9383	High Similarity	NPC100921
0.9383	High Similarity	NPC470400
0.9383	High Similarity	NPC475268
0.9383	High Similarity	NPC319036
0.9383	High Similarity	NPC9678
0.9383	High Similarity	NPC292809
0.9383	High Similarity	NPC473156
0.9383	High Similarity	NPC77871
0.9383	High Similarity	NPC202055
0.9383	High Similarity	NPC39279
0.9383	High Similarity	NPC39167
0.9383	High Similarity	NPC235809
0.9383	High Similarity	NPC473671
0.9286	High Similarity	NPC239517
0.9277	High Similarity	NPC100454
0.9277	High Similarity	NPC261952
0.9277	High Similarity	NPC234077
0.9277	High Similarity	NPC171135
0.9277	High Similarity	NPC81045
0.9277	High Similarity	NPC39754
0.9277	High Similarity	NPC169511
0.9277	High Similarity	NPC242364
0.9277	High Similarity	NPC320569
0.9277	High Similarity	NPC133730
0.9277	High Similarity	NPC172821
0.9277	High Similarity	NPC151403
0.9277	High Similarity	NPC61257
0.9277	High Similarity	NPC287164
0.9277	High Similarity	NPC191929
0.9277	High Similarity	NPC274446
0.9268	High Similarity	NPC309211
0.9268	High Similarity	NPC25703
0.9268	High Similarity	NPC219652
0.9268	High Similarity	NPC473840
0.9268	High Similarity	NPC282815
0.9268	High Similarity	NPC477010
0.9268	High Similarity	NPC112685
0.9167	High Similarity	NPC40066
0.9167	High Similarity	NPC473504
0.9167	High Similarity	NPC20621
0.9167	High Similarity	NPC81778
0.9167	High Similarity	NPC130359
0.9167	High Similarity	NPC139418
0.9167	High Similarity	NPC14901
0.9167	High Similarity	NPC91067
0.9167	High Similarity	NPC477011
0.9167	High Similarity	NPC93794
0.9167	High Similarity	NPC318963
0.9167	High Similarity	NPC42598
0.9157	High Similarity	NPC473649
0.9157	High Similarity	NPC159750
0.9157	High Similarity	NPC470401
0.9157	High Similarity	NPC154097
0.9157	High Similarity	NPC477012
0.9157	High Similarity	NPC473995
0.9146	High Similarity	NPC182383
0.9059	High Similarity	NPC473904
0.9036	High Similarity	NPC47937
0.8851	High Similarity	NPC473561
0.8851	High Similarity	NPC473663
0.8851	High Similarity	NPC11456
0.8851	High Similarity	NPC475173
0.8851	High Similarity	NPC473723
0.8851	High Similarity	NPC473520
0.8736	High Similarity	NPC473707
0.8409	Intermediate Similarity	NPC473448
0.8228	Intermediate Similarity	NPC84038
0.8222	Intermediate Similarity	NPC295204
0.8222	Intermediate Similarity	NPC288240
0.8222	Intermediate Similarity	NPC162205
0.8222	Intermediate Similarity	NPC273579
0.8202	Intermediate Similarity	NPC473619
0.8161	Intermediate Similarity	NPC469483
0.8125	Intermediate Similarity	NPC474705
0.8111	Intermediate Similarity	NPC473321
0.8111	Intermediate Similarity	NPC30515
0.8111	Intermediate Similarity	NPC184463
0.8095	Intermediate Similarity	NPC47653
0.8046	Intermediate Similarity	NPC21469
0.8043	Intermediate Similarity	NPC36954
0.8023	Intermediate Similarity	NPC475947
0.8023	Intermediate Similarity	NPC284472
0.8023	Intermediate Similarity	NPC229799
0.8023	Intermediate Similarity	NPC286770
0.8022	Intermediate Similarity	NPC179746
0.8022	Intermediate Similarity	NPC476300
0.8022	Intermediate Similarity	NPC81419
0.8022	Intermediate Similarity	NPC475912
0.8	Intermediate Similarity	NPC474761
0.8	Intermediate Similarity	NPC51004
0.8	Intermediate Similarity	NPC476004
0.7979	Intermediate Similarity	NPC473326
0.7979	Intermediate Similarity	NPC187268
0.7976	Intermediate Similarity	NPC470149
0.7976	Intermediate Similarity	NPC470148
0.7952	Intermediate Similarity	NPC475711
0.7931	Intermediate Similarity	NPC288471
0.7912	Intermediate Similarity	NPC12172
0.7912	Intermediate Similarity	NPC208886
0.7907	Intermediate Similarity	NPC11383
0.7907	Intermediate Similarity	NPC474959
0.7907	Intermediate Similarity	NPC475046
0.7907	Intermediate Similarity	NPC310450
0.7901	Intermediate Similarity	NPC144419
0.7889	Intermediate Similarity	NPC307411
0.7889	Intermediate Similarity	NPC295312
0.7882	Intermediate Similarity	NPC470147
0.7882	Intermediate Similarity	NPC133226
0.7857	Intermediate Similarity	NPC221095
0.7857	Intermediate Similarity	NPC248775
0.7857	Intermediate Similarity	NPC279214
0.7849	Intermediate Similarity	NPC270013
0.7849	Intermediate Similarity	NPC14961
0.7848	Intermediate Similarity	NPC48218
0.7848	Intermediate Similarity	NPC324981
0.7848	Intermediate Similarity	NPC218477
0.7848	Intermediate Similarity	NPC141481
0.7848	Intermediate Similarity	NPC473559
0.7826	Intermediate Similarity	NPC212486
0.7816	Intermediate Similarity	NPC40746
0.7816	Intermediate Similarity	NPC116543
0.7816	Intermediate Similarity	NPC169575

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 NPC163093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	2148
0.2-0.3	3861
0.3-0.4	2076
0.4-0.5	599
0.5-0.6	255
0.6-0.7	52
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
0.8	Intermediate Similarity	NPD6698	Approved
0.8	Intermediate Similarity	NPD46	Approved
0.7609	Intermediate Similarity	NPD7838	Discovery
0.76	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6686	Approved
0.734	Intermediate Similarity	NPD7983	Approved
0.7048	Intermediate Similarity	NPD6371	Approved
0.6939	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4251	Approved
0.6915	Remote Similarity	NPD4250	Approved
0.6914	Remote Similarity	NPD3197	Phase 1
0.69	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7154	Phase 3
0.6822	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4249	Approved
0.6733	Remote Similarity	NPD4225	Approved
0.6703	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6602	Remote Similarity	NPD5344	Discontinued
0.6598	Remote Similarity	NPD1695	Approved
0.6559	Remote Similarity	NPD6435	Approved
0.6559	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4756	Discovery
0.6526	Remote Similarity	NPD5363	Approved
0.6484	Remote Similarity	NPD4271	Approved
0.6484	Remote Similarity	NPD4268	Approved
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6053	Discontinued
0.6421	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3730	Approved
0.641	Remote Similarity	NPD3728	Approved
0.6408	Remote Similarity	NPD7638	Approved
0.64	Remote Similarity	NPD5778	Approved
0.64	Remote Similarity	NPD5779	Approved
0.6373	Remote Similarity	NPD7839	Suspended
0.6356	Remote Similarity	NPD7507	Approved
0.6346	Remote Similarity	NPD7639	Approved
0.6346	Remote Similarity	NPD7640	Approved
0.6344	Remote Similarity	NPD4822	Approved
0.6344	Remote Similarity	NPD4819	Approved
0.6344	Remote Similarity	NPD4821	Approved
0.6344	Remote Similarity	NPD5368	Approved
0.6344	Remote Similarity	NPD4820	Approved
0.6341	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8039	Approved
0.6304	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8515	Approved
0.6293	Remote Similarity	NPD8513	Phase 3
0.6293	Remote Similarity	NPD8516	Approved
0.6293	Remote Similarity	NPD8517	Approved
0.6235	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7115	Discovery
0.6211	Remote Similarity	NPD4269	Approved
0.6211	Remote Similarity	NPD4270	Approved
0.6211	Remote Similarity	NPD5209	Approved
0.6203	Remote Similarity	NPD4266	Approved
0.6203	Remote Similarity	NPD3195	Phase 2
0.6203	Remote Similarity	NPD3196	Approved
0.6203	Remote Similarity	NPD3194	Approved
0.6198	Remote Similarity	NPD7319	Approved
0.619	Remote Similarity	NPD6648	Approved
0.6186	Remote Similarity	NPD7830	Approved
0.6186	Remote Similarity	NPD7829	Approved
0.6186	Remote Similarity	NPD1694	Approved
0.6176	Remote Similarity	NPD5282	Discontinued
0.617	Remote Similarity	NPD4252	Approved
0.6147	Remote Similarity	NPD6412	Phase 2
0.6146	Remote Similarity	NPD5332	Approved
0.6146	Remote Similarity	NPD6110	Phase 1
0.6146	Remote Similarity	NPD5331	Approved
0.6126	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5786	Approved
0.6105	Remote Similarity	NPD4790	Discontinued
0.6105	Remote Similarity	NPD5369	Approved
0.6098	Remote Similarity	NPD9119	Approved
0.6098	Remote Similarity	NPD6109	Phase 1
0.6098	Remote Similarity	NPD69	Approved
0.6076	Remote Similarity	NPD3172	Approved
0.6068	Remote Similarity	NPD8377	Approved
0.6068	Remote Similarity	NPD8294	Approved
0.6034	Remote Similarity	NPD7327	Approved
0.6034	Remote Similarity	NPD7328	Approved
0.6033	Remote Similarity	NPD8074	Phase 3
0.6026	Remote Similarity	NPD6927	Phase 3
0.6018	Remote Similarity	NPD8297	Approved
0.6017	Remote Similarity	NPD8296	Approved
0.6017	Remote Similarity	NPD8379	Approved
0.6017	Remote Similarity	NPD8380	Approved
0.6017	Remote Similarity	NPD8033	Approved
0.6017	Remote Similarity	NPD8335	Approved
0.6017	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7516	Approved
0.598	Remote Similarity	NPD7637	Suspended
0.5977	Remote Similarity	NPD3704	Approved
0.5976	Remote Similarity	NPD9118	Approved
0.5941	Remote Similarity	NPD6101	Approved
0.5941	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7642	Approved
0.5897	Remote Similarity	NPD7641	Discontinued
0.5882	Remote Similarity	NPD8444	Approved
0.5868	Remote Similarity	NPD7492	Approved
0.5865	Remote Similarity	NPD7748	Approved
0.5856	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7736	Approved
0.5849	Remote Similarity	NPD6084	Phase 2
0.5849	Remote Similarity	NPD7902	Approved
0.5849	Remote Similarity	NPD6083	Phase 2
0.5841	Remote Similarity	NPD6421	Discontinued
0.5826	Remote Similarity	NPD8133	Approved
0.5826	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD6411	Approved
0.5823	Remote Similarity	NPD29	Approved
0.5823	Remote Similarity	NPD28	Approved
0.582	Remote Similarity	NPD6616	Approved
0.582	Remote Similarity	NPD8273	Phase 1
0.5812	Remote Similarity	NPD7505	Discontinued
0.5804	Remote Similarity	NPD7320	Approved
0.5804	Remote Similarity	NPD6881	Approved
0.5804	Remote Similarity	NPD6899	Approved
0.5798	Remote Similarity	NPD6319	Approved
0.5798	Remote Similarity	NPD6054	Approved
0.5795	Remote Similarity	NPD7331	Phase 2
0.5795	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD2204	Approved
0.5789	Remote Similarity	NPD8130	Phase 1
0.5784	Remote Similarity	NPD5370	Suspended
0.578	Remote Similarity	NPD7632	Discontinued
0.5772	Remote Similarity	NPD8293	Discontinued
0.5772	Remote Similarity	NPD7078	Approved
0.5769	Remote Similarity	NPD6399	Phase 3
0.5766	Remote Similarity	NPD7128	Approved
0.5766	Remote Similarity	NPD5739	Approved
0.5766	Remote Similarity	NPD6402	Approved
0.5766	Remote Similarity	NPD6675	Approved
0.5755	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7503	Approved
0.5727	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD5697	Approved
0.5702	Remote Similarity	NPD6883	Approved
0.5702	Remote Similarity	NPD6370	Approved
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD2067	Discontinued
0.5702	Remote Similarity	NPD7102	Approved
0.5691	Remote Similarity	NPD8451	Approved
0.5686	Remote Similarity	NPD6903	Approved
0.5678	Remote Similarity	NPD7500	Approved
0.5673	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD7515	Phase 2
0.5667	Remote Similarity	NPD6059	Approved
0.5664	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5695	Phase 3
0.5656	Remote Similarity	NPD8328	Phase 3
0.5652	Remote Similarity	NPD6869	Approved
0.5652	Remote Similarity	NPD6847	Approved
0.5652	Remote Similarity	NPD6617	Approved
0.5652	Remote Similarity	NPD6649	Approved
0.5652	Remote Similarity	NPD6650	Approved
0.5645	Remote Similarity	NPD8448	Approved
0.5644	Remote Similarity	NPD7334	Approved
0.5644	Remote Similarity	NPD6684	Approved
0.5644	Remote Similarity	NPD6409	Approved
0.5644	Remote Similarity	NPD7521	Approved
0.5644	Remote Similarity	NPD6422	Discontinued
0.5644	Remote Similarity	NPD5330	Approved
0.5644	Remote Similarity	NPD7146	Approved
0.5641	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4211	Phase 1
0.5625	Remote Similarity	NPD3732	Approved
0.562	Remote Similarity	NPD6016	Approved
0.562	Remote Similarity	NPD6015	Approved
0.5614	Remote Similarity	NPD6014	Approved
0.5614	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6012	Approved
0.5614	Remote Similarity	NPD6373	Approved
0.5614	Remote Similarity	NPD6372	Approved
0.5614	Remote Similarity	NPD6013	Approved
0.5603	Remote Similarity	NPD6882	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