NPASS Compound

Structure

CID182383 OpenBabel06191715562D 42 43 0 0 1 0 0 0 0 0999 V2000 -23.5993 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -22.7333 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -21.8673 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -21.0013 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.1352 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.2692 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.4032 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.5372 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.6711 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.8051 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.9391 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7429 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6090 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1449 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8769 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4750 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0731 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4750 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4750 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0109 1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8147 1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.3410 1.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.3410 4.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.2070 4.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.3410 2.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0109 0.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 0.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2070 1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3410 5.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 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 -13.2070 3.2024 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 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 18 29 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 23 24 1 0 0 0 0 23 32 1 0 0 0 0 24 34 1 0 0 0 0 25 27 1 0 0 0 0 25 28 2 0 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 27 2 1 6 0 0 0 27 41 1 0 0 0 0 28 35 1 0 0 0 0 29 36 1 1 0 0 0 30 37 1 6 0 0 0 31 38 1 1 0 0 0 32 33 1 0 0 0 0 32 39 1 6 0 0 0 33 22 1 6 0 0 0 33 42 1 0 0 0 0 34 31 1 6 0 0 0 34 42 1 0 0 0 0 35 40 2 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.47
Volume:	653.062
LogP:	7.939
LogD:	4.413
LogS:	-6.486
# Rotatable Bonds:	25
TPSA:	123.52
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.073
Synthetic Accessibility Score:	4.493
Fsp3:	0.886
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:	-5.403
MDCK Permeability:	1.5453770174644887e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.765

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	98.23302459716797%
Volume Distribution (VD):	0.656
Pgp-substrate:	2.7573471069335938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.231
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.977
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	6.111
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.969
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.298

Download Data

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

Natural Product: NPC182383

Natural Product ID:	NPC182383
*Common Name:**	Pyranicin
IUPAC Name:	(2S)-4-[(2R,8R,13R)-13-[(2R,5R,6R)-6-dodecyl-5-hydroxyoxan-2-yl]-2,8,13-trihydroxytridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Pyranicin
Standard InCHIKey:	DKEKHIOBJJTNIY-CGWDHHCXSA-N
Standard InCHI:	InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-22-33-32(39)23-24-34(42-33)31(38)21-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1
SMILES:	CCCCCCCCCCCC[C@H]1O[C@H](CC[C@H]1O)[C@@H](CCCC[C@@H](CCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455650
PubChem CID:	10326192
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
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7202	Goniothalamus giganteus	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
ED50	6
Others	1

Activity Type	# Activity
Cell Line	6
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	4.1	10'-1 ug/ml	PMID[447488]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	=	1.3	10'-3 ug/ml	PMID[447488]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.8	10'-1 ug/ml	PMID[447488]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.9	10'-1 ug/ml	PMID[447488]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.2	ug ml-1	PMID[447488]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	1.8	10'-1 ug/ml	PMID[447488]
NPT140	Organism	Artemia	Artemia	LC50	=	0.3	ug.mL-1	PMID[447488]

☑ 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 NPC182383 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	169
0.1-0.2	1213
0.2-0.3	5003
0.3-0.4	10575
0.4-0.5	13590
0.5-0.6	7657
0.6-0.7	3674
0.7-0.8	643
0.8-0.85	79
0.85-0.9	76
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC47937
0.9506	High Similarity	NPC473478
0.9506	High Similarity	NPC107986
0.9506	High Similarity	NPC283085
0.9506	High Similarity	NPC103284
0.9506	High Similarity	NPC82795
0.9506	High Similarity	NPC473669
0.9506	High Similarity	NPC231009
0.9506	High Similarity	NPC286338
0.9506	High Similarity	NPC223871
0.9506	High Similarity	NPC473651
0.9506	High Similarity	NPC110710
0.9506	High Similarity	NPC66346
0.9506	High Similarity	NPC132496
0.9506	High Similarity	NPC1083
0.939	High Similarity	NPC62118
0.939	High Similarity	NPC114694
0.939	High Similarity	NPC69082
0.939	High Similarity	NPC142117
0.939	High Similarity	NPC103523
0.939	High Similarity	NPC210218
0.939	High Similarity	NPC134885
0.939	High Similarity	NPC473687
0.939	High Similarity	NPC240695
0.939	High Similarity	NPC171174
0.939	High Similarity	NPC204686
0.939	High Similarity	NPC232555
0.939	High Similarity	NPC134865
0.939	High Similarity	NPC107717
0.939	High Similarity	NPC134807
0.939	High Similarity	NPC231096
0.939	High Similarity	NPC475581
0.939	High Similarity	NPC308412
0.939	High Similarity	NPC279267
0.939	High Similarity	NPC219498
0.9277	High Similarity	NPC178215
0.9167	High Similarity	NPC151403
0.9167	High Similarity	NPC280621
0.9167	High Similarity	NPC81045
0.9167	High Similarity	NPC133730
0.9167	High Similarity	NPC61257
0.9167	High Similarity	NPC169511
0.9167	High Similarity	NPC233551
0.9167	High Similarity	NPC172821
0.9167	High Similarity	NPC191929
0.9167	High Similarity	NPC274446
0.9167	High Similarity	NPC20339
0.9167	High Similarity	NPC21208
0.9167	High Similarity	NPC39754
0.9167	High Similarity	NPC261952
0.9167	High Similarity	NPC242364
0.9167	High Similarity	NPC171135
0.9167	High Similarity	NPC40376
0.9167	High Similarity	NPC100454
0.9167	High Similarity	NPC287164
0.9167	High Similarity	NPC48338
0.9167	High Similarity	NPC320569
0.9167	High Similarity	NPC234077
0.9157	High Similarity	NPC112685
0.9146	High Similarity	NPC163093
0.9146	High Similarity	NPC156804
0.9136	High Similarity	NPC180363
0.9136	High Similarity	NPC473780
0.9136	High Similarity	NPC11332
0.9136	High Similarity	NPC473529
0.9136	High Similarity	NPC73310
0.9136	High Similarity	NPC145914
0.9136	High Similarity	NPC329829
0.9136	High Similarity	NPC65930
0.9136	High Similarity	NPC131002
0.9136	High Similarity	NPC473712
0.9136	High Similarity	NPC475159
0.9136	High Similarity	NPC94875
0.9059	High Similarity	NPC14901
0.9059	High Similarity	NPC93794
0.9059	High Similarity	NPC318963
0.9059	High Similarity	NPC91067
0.9059	High Similarity	NPC20621
0.9059	High Similarity	NPC40066
0.9059	High Similarity	NPC473504
0.9059	High Similarity	NPC81778
0.9059	High Similarity	NPC477011
0.9059	High Similarity	NPC130359
0.9059	High Similarity	NPC139418
0.9059	High Similarity	NPC42598
0.9048	High Similarity	NPC473995
0.9036	High Similarity	NPC471567
0.9036	High Similarity	NPC329615
0.9036	High Similarity	NPC477014
0.9036	High Similarity	NPC329838
0.9036	High Similarity	NPC322529
0.9036	High Similarity	NPC477013
0.9036	High Similarity	NPC120398
0.9024	High Similarity	NPC144415
0.9024	High Similarity	NPC253801
0.8953	High Similarity	NPC473904
0.8953	High Similarity	NPC239517
0.8929	High Similarity	NPC477015
0.8929	High Similarity	NPC293136
0.8929	High Similarity	NPC241360
0.8929	High Similarity	NPC132940
0.8837	High Similarity	NPC280612
0.8824	High Similarity	NPC476583
0.8824	High Similarity	NPC20533
0.8824	High Similarity	NPC258068
0.881	High Similarity	NPC477018
0.881	High Similarity	NPC100921
0.881	High Similarity	NPC235809
0.881	High Similarity	NPC77871
0.881	High Similarity	NPC473156
0.881	High Similarity	NPC25764
0.881	High Similarity	NPC9678
0.881	High Similarity	NPC475268
0.881	High Similarity	NPC470400
0.881	High Similarity	NPC39279
0.881	High Similarity	NPC319036
0.881	High Similarity	NPC292809
0.881	High Similarity	NPC202055
0.881	High Similarity	NPC39167
0.881	High Similarity	NPC473671
0.875	High Similarity	NPC473561
0.875	High Similarity	NPC473723
0.875	High Similarity	NPC473663
0.875	High Similarity	NPC475173
0.875	High Similarity	NPC11456
0.8721	High Similarity	NPC320458
0.8721	High Similarity	NPC89001
0.8721	High Similarity	NPC473905
0.8706	High Similarity	NPC473840
0.8706	High Similarity	NPC477010
0.8706	High Similarity	NPC25703
0.8706	High Similarity	NPC282815
0.8706	High Similarity	NPC219652
0.8706	High Similarity	NPC309211
0.8636	High Similarity	NPC473707
0.8621	High Similarity	NPC477017
0.8621	High Similarity	NPC477016
0.8605	High Similarity	NPC159750
0.8605	High Similarity	NPC477012
0.8605	High Similarity	NPC473649
0.8605	High Similarity	NPC470401
0.8605	High Similarity	NPC154097
0.8333	Intermediate Similarity	NPC473520
0.8293	Intermediate Similarity	NPC475711
0.8222	Intermediate Similarity	NPC30515
0.8161	Intermediate Similarity	NPC21469
0.8132	Intermediate Similarity	NPC273579
0.8132	Intermediate Similarity	NPC162205
0.8132	Intermediate Similarity	NPC295204
0.8132	Intermediate Similarity	NPC288240
0.8111	Intermediate Similarity	NPC473448
0.8111	Intermediate Similarity	NPC473619
0.8111	Intermediate Similarity	NPC51004
0.8095	Intermediate Similarity	NPC470148
0.8095	Intermediate Similarity	NPC470149
0.8068	Intermediate Similarity	NPC469483
0.8046	Intermediate Similarity	NPC474251
0.8022	Intermediate Similarity	NPC327760
0.8022	Intermediate Similarity	NPC184463
0.8022	Intermediate Similarity	NPC473321
0.8	Intermediate Similarity	NPC470147
0.8	Intermediate Similarity	NPC307411
0.8	Intermediate Similarity	NPC133226
0.8	Intermediate Similarity	NPC47653
0.7976	Intermediate Similarity	NPC248775
0.7957	Intermediate Similarity	NPC36954
0.7952	Intermediate Similarity	NPC190400
0.7952	Intermediate Similarity	NPC49392
0.7935	Intermediate Similarity	NPC475912
0.7935	Intermediate Similarity	NPC476300
0.7935	Intermediate Similarity	NPC81419
0.7935	Intermediate Similarity	NPC179746
0.7931	Intermediate Similarity	NPC284472
0.7931	Intermediate Similarity	NPC229799
0.7931	Intermediate Similarity	NPC286770
0.7912	Intermediate Similarity	NPC474761
0.7912	Intermediate Similarity	NPC476004
0.7901	Intermediate Similarity	NPC84038
0.7889	Intermediate Similarity	NPC202672
0.7882	Intermediate Similarity	NPC180725
0.7872	Intermediate Similarity	NPC306041
0.7857	Intermediate Similarity	NPC474026
0.7849	Intermediate Similarity	NPC81386
0.7849	Intermediate Similarity	NPC474035
0.7849	Intermediate Similarity	NPC71589
0.7841	Intermediate Similarity	NPC288471
0.7841	Intermediate Similarity	NPC9868
0.7841	Intermediate Similarity	NPC243618
0.7841	Intermediate Similarity	NPC70424
0.7826	Intermediate Similarity	NPC303230
0.7826	Intermediate Similarity	NPC208886
0.7826	Intermediate Similarity	NPC6099
0.7826	Intermediate Similarity	NPC12172
0.7826	Intermediate Similarity	NPC114345
0.7816	Intermediate Similarity	NPC474959
0.7816	Intermediate Similarity	NPC11383
0.7816	Intermediate Similarity	NPC310450
0.7816	Intermediate Similarity	NPC475046
0.7805	Intermediate Similarity	NPC474705
0.7802	Intermediate Similarity	NPC295312

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 NPC182383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1739
0.2-0.3	3771
0.3-0.4	2347
0.4-0.5	800
0.5-0.6	296
0.6-0.7	52
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8315	Intermediate Similarity	NPD6698	Approved
0.8315	Intermediate Similarity	NPD46	Approved
0.7527	Intermediate Similarity	NPD7838	Discovery
0.7526	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6686	Approved
0.7353	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD6371	Approved
0.7075	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5785	Approved
0.6854	Remote Similarity	NPD4756	Discovery
0.6832	Remote Similarity	NPD4225	Approved
0.6829	Remote Similarity	NPD3197	Phase 1
0.6809	Remote Similarity	NPD5363	Approved
0.6809	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7154	Phase 3
0.67	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7839	Suspended
0.6632	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5362	Discontinued
0.6588	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8517	Approved
0.6522	Remote Similarity	NPD8516	Approved
0.6522	Remote Similarity	NPD8515	Approved
0.6522	Remote Similarity	NPD8513	Phase 3
0.6505	Remote Similarity	NPD7638	Approved
0.65	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD5779	Approved
0.6495	Remote Similarity	NPD4250	Approved
0.6495	Remote Similarity	NPD4251	Approved
0.6489	Remote Similarity	NPD4270	Approved
0.6489	Remote Similarity	NPD4269	Approved
0.646	Remote Similarity	NPD7115	Discovery
0.6452	Remote Similarity	NPD4252	Approved
0.6444	Remote Similarity	NPD8039	Approved
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6422	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6110	Phase 1
0.6413	Remote Similarity	NPD4271	Approved
0.6413	Remote Similarity	NPD4268	Approved
0.641	Remote Similarity	NPD7829	Approved
0.641	Remote Similarity	NPD7830	Approved
0.6396	Remote Similarity	NPD6053	Discontinued
0.6392	Remote Similarity	NPD4249	Approved
0.6392	Remote Similarity	NPD5786	Approved
0.6383	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD1695	Approved
0.6316	Remote Similarity	NPD6435	Approved
0.631	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7507	Approved
0.6289	Remote Similarity	NPD1694	Approved
0.6286	Remote Similarity	NPD6648	Approved
0.6279	Remote Similarity	NPD3704	Approved
0.6277	Remote Similarity	NPD4819	Approved
0.6277	Remote Similarity	NPD4821	Approved
0.6277	Remote Similarity	NPD4822	Approved
0.6277	Remote Similarity	NPD4820	Approved
0.6275	Remote Similarity	NPD5282	Discontinued
0.6271	Remote Similarity	NPD7642	Approved
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7641	Discontinued
0.625	Remote Similarity	NPD8074	Phase 3
0.6239	Remote Similarity	NPD6412	Phase 2
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6101	Approved
0.6176	Remote Similarity	NPD6399	Phase 3
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7319	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6125	Remote Similarity	NPD4266	Approved
0.6125	Remote Similarity	NPD3728	Approved
0.6125	Remote Similarity	NPD3730	Approved
0.6125	Remote Similarity	NPD3194	Approved
0.6125	Remote Similarity	NPD3195	Phase 2
0.6125	Remote Similarity	NPD3196	Approved
0.6105	Remote Similarity	NPD5368	Approved
0.6102	Remote Similarity	NPD8033	Approved
0.6102	Remote Similarity	NPD8444	Approved
0.6095	Remote Similarity	NPD7902	Approved
0.6092	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5332	Approved
0.6082	Remote Similarity	NPD5331	Approved
0.6078	Remote Similarity	NPD6411	Approved
0.6078	Remote Similarity	NPD7637	Suspended
0.6078	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2067	Discontinued
0.6063	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6422	Discontinued
0.6048	Remote Similarity	NPD7260	Phase 2
0.6042	Remote Similarity	NPD4790	Discontinued
0.604	Remote Similarity	NPD5370	Suspended
0.6033	Remote Similarity	NPD8451	Approved
0.6033	Remote Similarity	NPD8273	Phase 1
0.6024	Remote Similarity	NPD69	Approved
0.6024	Remote Similarity	NPD6109	Phase 1
0.6024	Remote Similarity	NPD9119	Approved
0.6018	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD8294	Approved
0.6017	Remote Similarity	NPD8377	Approved
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8448	Approved
0.5983	Remote Similarity	NPD7328	Approved
0.5983	Remote Similarity	NPD7327	Approved
0.5966	Remote Similarity	NPD8335	Approved
0.5966	Remote Similarity	NPD8296	Approved
0.5966	Remote Similarity	NPD8380	Approved
0.5966	Remote Similarity	NPD8379	Approved
0.5966	Remote Similarity	NPD8378	Approved
0.5965	Remote Similarity	NPD8297	Approved
0.5962	Remote Similarity	NPD7748	Approved
0.5949	Remote Similarity	NPD6927	Phase 3
0.5946	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7516	Approved
0.5929	Remote Similarity	NPD6421	Discontinued
0.5913	Remote Similarity	NPD4632	Approved
0.5913	Remote Similarity	NPD8133	Approved
0.5909	Remote Similarity	NPD7331	Phase 2
0.5904	Remote Similarity	NPD9118	Approved
0.5897	Remote Similarity	NPD7500	Approved
0.5897	Remote Similarity	NPD7505	Discontinued
0.5893	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7632	Discontinued
0.5868	Remote Similarity	NPD8328	Phase 3
0.5841	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8390	Approved
0.584	Remote Similarity	NPD8392	Approved
0.584	Remote Similarity	NPD8391	Approved
0.5833	Remote Similarity	NPD7503	Approved
0.582	Remote Similarity	NPD8340	Approved
0.582	Remote Similarity	NPD8341	Approved
0.582	Remote Similarity	NPD8299	Approved
0.582	Remote Similarity	NPD8342	Approved
0.5818	Remote Similarity	NPD6647	Phase 2
0.581	Remote Similarity	NPD7900	Approved
0.581	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6083	Phase 2
0.5794	Remote Similarity	NPD6084	Phase 2
0.5785	Remote Similarity	NPD8080	Discontinued
0.5773	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7515	Phase 2
0.5763	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6899	Approved
0.5752	Remote Similarity	NPD6881	Approved
0.575	Remote Similarity	NPD28	Approved
0.575	Remote Similarity	NPD29	Approved
0.575	Remote Similarity	NPD6319	Approved
0.5748	Remote Similarity	NPD6845	Suspended
0.5743	Remote Similarity	NPD7521	Approved
0.5743	Remote Similarity	NPD5330	Approved
0.5743	Remote Similarity	NPD7146	Approved
0.5743	Remote Similarity	NPD7334	Approved
0.5743	Remote Similarity	NPD6409	Approved
0.5743	Remote Similarity	NPD6684	Approved
0.5739	Remote Similarity	NPD6650	Approved
0.5739	Remote Similarity	NPD8130	Phase 1
0.5739	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD4211	Phase 1
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5702	Remote Similarity	NPD6372	Approved
0.5702	Remote Similarity	NPD6373	Approved
0.5686	Remote Similarity	NPD7524	Approved
0.5676	Remote Similarity	NPD2258	Approved
0.5676	Remote Similarity	NPD2259	Approved
0.5673	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5697	Approved
0.5652	Remote Similarity	NPD7290	Approved
0.5652	Remote Similarity	NPD6883	Approved
0.5652	Remote Similarity	NPD7102	Approved
0.5631	Remote Similarity	NPD5737	Approved
0.5631	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6903	Approved
0.5631	Remote Similarity	NPD6672	Approved
0.563	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6009	Approved
0.562	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD8034	Phase 2
0.5619	Remote Similarity	NPD8035	Phase 2
0.5614	Remote Similarity	NPD7320	Approved
0.5614	Remote Similarity	NPD6011	Approved
0.561	Remote Similarity	NPD7604	Phase 2
0.5607	Remote Similarity	NPD5695	Phase 3
0.5603	Remote Similarity	NPD2204	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