NPASS Compound

Structure

CID39167 OpenBabel06191715372D 43 45 0 0 1 0 0 0 0 0999 V2000 18.4410 -5.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 -1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.1320 -4.1912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1538 -3.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4847 -4.7264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5065 -4.5185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8374 -5.2616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3431 0.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3212 0.5888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6740 0.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9904 1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6958 0.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8593 -5.0537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9685 1.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0267 -0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1901 -5.7969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6376 1.8671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 -0.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2120 -5.5890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6158 1.6592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5428 -6.3321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9248 0.7082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3046 -4.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5158 -1.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3046 -3.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5158 -2.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 2 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 10.5647 -6.1242 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2557 -0.0350 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2557 -5.1731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5647 -0.9860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2557 -3.5551 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5647 -2.6041 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8956 -6.8673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2775 0.1729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 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 10.8435 -4.3641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9769 -1.7950 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 13 1 0 0 0 0 8 9 1 0 0 0 0 8 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 30 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 26 1 0 0 0 0 24 33 1 0 0 0 0 25 27 1 0 0 0 0 25 34 1 0 0 0 0 28 29 1 0 0 0 0 28 30 2 0 0 0 0 29 2 1 1 0 0 0 29 41 1 0 0 0 0 30 37 1 0 0 0 0 31 38 1 6 0 0 0 32 39 1 6 0 0 0 33 31 1 1 0 0 0 33 42 1 0 0 0 0 34 32 1 1 0 0 0 34 43 1 0 0 0 0 35 26 1 6 0 0 0 35 36 1 0 0 0 0 35 42 1 0 0 0 0 36 27 1 6 0 0 0 36 43 1 0 0 0 0 37 40 2 0 0 0 0 37 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.49
Volume:	670.307
LogP:	10.584
LogD:	5.333
LogS:	-6.849
# Rotatable Bonds:	25
TPSA:	92.29
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.096
Synthetic Accessibility Score:	4.476
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:	-5.25
MDCK Permeability:	8.225775673054159e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.517
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.25774383544922%
Volume Distribution (VD):	1.511
Pgp-substrate:	2.3073837757110596%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	3.404
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.445
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.362
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.197
Skin Sensitization:	0.972
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.307

Download Data

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

Natural Product: NPC39167

Natural Product ID:	NPC39167
*Common Name:**	Isodesacetyluvaricin
IUPAC Name:	(2R)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Isodesacetyluvaricin
Standard InCHIKey:	URLVCROWVOSNPT-JOZNLICQSA-N
Standard InCHI:	InChI=1S/C37H66O6/c1-3-4-5-6-7-13-16-19-22-31(38)33-24-26-35(42-33)36-27-25-34(43-36)32(39)23-20-17-14-11-9-8-10-12-15-18-21-30-28-29(2)41-37(30)40/h28-29,31-36,38-39H,3-27H2,1-2H3/t29-,31+,32-,33-,34-,35-,36-/m1/s1
SMILES:	CCCCCCCCCC[C@@H]([C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@@H](CCCCCCCCCCCCC1=C[C@H](OC1=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484529
PubChem CID:	44591854
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
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643056]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25214	Uvaria narum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25214	Uvaria narum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20295	Eclipta prostrata	Species	Asteraceae	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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	13.0	nM	PMID[480828]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	=	84.0	nM	PMID[480828]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	21.0	nM	PMID[480828]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	80000.0	nM	PMID[480829]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16.0	nM	PMID[480828]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	160.0	nM	PMID[480828]

☑ 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 NPC39167 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	182
0.1-0.2	1429
0.2-0.3	6117
0.3-0.4	15459
0.4-0.5	10186
0.5-0.6	6616
0.6-0.7	2212
0.7-0.8	316
0.8-0.85	20
0.85-0.9	42
0.9-0.95	62
0.95-1	56

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235809
1.0	High Similarity	NPC292809
1.0	High Similarity	NPC77871
1.0	High Similarity	NPC473156
1.0	High Similarity	NPC39279
1.0	High Similarity	NPC9678
1.0	High Similarity	NPC473671
1.0	High Similarity	NPC25764
1.0	High Similarity	NPC202055
1.0	High Similarity	NPC475268
1.0	High Similarity	NPC319036
1.0	High Similarity	NPC470400
0.9875	High Similarity	NPC293136
0.9875	High Similarity	NPC282815
0.9875	High Similarity	NPC132940
0.9875	High Similarity	NPC25703
0.9875	High Similarity	NPC219652
0.9875	High Similarity	NPC241360
0.9875	High Similarity	NPC473840
0.9753	High Similarity	NPC470401
0.9753	High Similarity	NPC159750
0.9753	High Similarity	NPC258068
0.9753	High Similarity	NPC476583
0.9753	High Similarity	NPC473995
0.9753	High Similarity	NPC20533
0.9753	High Similarity	NPC473649
0.9753	High Similarity	NPC154097
0.9634	High Similarity	NPC81045
0.9634	High Similarity	NPC274446
0.9634	High Similarity	NPC191929
0.9634	High Similarity	NPC171135
0.9634	High Similarity	NPC39754
0.9634	High Similarity	NPC100454
0.9634	High Similarity	NPC320569
0.9634	High Similarity	NPC169511
0.9634	High Similarity	NPC473905
0.9634	High Similarity	NPC133730
0.9634	High Similarity	NPC234077
0.9634	High Similarity	NPC242364
0.9634	High Similarity	NPC172821
0.9634	High Similarity	NPC261952
0.9634	High Similarity	NPC320458
0.9634	High Similarity	NPC61257
0.9634	High Similarity	NPC151403
0.9634	High Similarity	NPC287164
0.9625	High Similarity	NPC156804
0.962	High Similarity	NPC11332
0.962	High Similarity	NPC475159
0.962	High Similarity	NPC65930
0.962	High Similarity	NPC473780
0.962	High Similarity	NPC145914
0.962	High Similarity	NPC94875
0.962	High Similarity	NPC473712
0.962	High Similarity	NPC180363
0.962	High Similarity	NPC131002
0.962	High Similarity	NPC329829
0.962	High Similarity	NPC473529
0.962	High Similarity	NPC73310
0.9518	High Similarity	NPC91067
0.9518	High Similarity	NPC20621
0.9518	High Similarity	NPC81778
0.9518	High Similarity	NPC40066
0.9518	High Similarity	NPC42598
0.9518	High Similarity	NPC93794
0.9518	High Similarity	NPC473504
0.9518	High Similarity	NPC318963
0.9506	High Similarity	NPC322529
0.9506	High Similarity	NPC329838
0.9506	High Similarity	NPC329615
0.9506	High Similarity	NPC471567
0.9506	High Similarity	NPC100921
0.9506	High Similarity	NPC477018
0.9506	High Similarity	NPC120398
0.95	High Similarity	NPC253801
0.95	High Similarity	NPC144415
0.9405	High Similarity	NPC239517
0.939	High Similarity	NPC231096
0.939	High Similarity	NPC240695
0.939	High Similarity	NPC142117
0.939	High Similarity	NPC232555
0.939	High Similarity	NPC62118
0.939	High Similarity	NPC309211
0.939	High Similarity	NPC475581
0.939	High Similarity	NPC171174
0.939	High Similarity	NPC107717
0.939	High Similarity	NPC477010
0.939	High Similarity	NPC114694
0.9383	High Similarity	NPC163093
0.9268	High Similarity	NPC477014
0.9268	High Similarity	NPC66346
0.9268	High Similarity	NPC473669
0.9268	High Similarity	NPC107986
0.9268	High Similarity	NPC110710
0.9268	High Similarity	NPC82795
0.9268	High Similarity	NPC473478
0.9268	High Similarity	NPC286338
0.9268	High Similarity	NPC132496
0.9268	High Similarity	NPC1083
0.9268	High Similarity	NPC103284
0.9268	High Similarity	NPC283085
0.9268	High Similarity	NPC223871
0.9268	High Similarity	NPC231009
0.9268	High Similarity	NPC477013
0.9268	High Similarity	NPC473651
0.9186	High Similarity	NPC473520
0.9167	High Similarity	NPC20339
0.9167	High Similarity	NPC21208
0.9167	High Similarity	NPC89001
0.9167	High Similarity	NPC233551
0.9167	High Similarity	NPC40376
0.9167	High Similarity	NPC280621
0.9167	High Similarity	NPC48338
0.9157	High Similarity	NPC134807
0.9157	High Similarity	NPC473687
0.9157	High Similarity	NPC210218
0.9157	High Similarity	NPC103523
0.9157	High Similarity	NPC477015
0.9157	High Similarity	NPC204686
0.9157	High Similarity	NPC219498
0.9157	High Similarity	NPC279267
0.9157	High Similarity	NPC134865
0.9157	High Similarity	NPC134885
0.9157	High Similarity	NPC308412
0.9157	High Similarity	NPC69082
0.9059	High Similarity	NPC477011
0.9059	High Similarity	NPC477016
0.9059	High Similarity	NPC477017
0.9048	High Similarity	NPC178215
0.9048	High Similarity	NPC477012
0.8953	High Similarity	NPC473904
0.8929	High Similarity	NPC112685
0.8929	High Similarity	NPC47937
0.8837	High Similarity	NPC280612
0.8837	High Similarity	NPC14901
0.8837	High Similarity	NPC139418
0.8837	High Similarity	NPC130359
0.881	High Similarity	NPC182383
0.875	High Similarity	NPC473561
0.875	High Similarity	NPC473663
0.875	High Similarity	NPC475173
0.875	High Similarity	NPC473723
0.8636	High Similarity	NPC473707
0.8539	High Similarity	NPC11456
0.8132	Intermediate Similarity	NPC81419
0.8132	Intermediate Similarity	NPC179746
0.8125	Intermediate Similarity	NPC84038
0.8111	Intermediate Similarity	NPC474761
0.8111	Intermediate Similarity	NPC476004
0.8025	Intermediate Similarity	NPC474705
0.8022	Intermediate Similarity	NPC208886
0.8022	Intermediate Similarity	NPC12172
0.8022	Intermediate Similarity	NPC30515
0.8	Intermediate Similarity	NPC295312
0.7955	Intermediate Similarity	NPC21469
0.7912	Intermediate Similarity	NPC473448
0.7912	Intermediate Similarity	NPC51004
0.7912	Intermediate Similarity	NPC473619
0.7895	Intermediate Similarity	NPC187268
0.7865	Intermediate Similarity	NPC164393
0.7857	Intermediate Similarity	NPC475711
0.7835	Intermediate Similarity	NPC86077
0.7826	Intermediate Similarity	NPC473321
0.7826	Intermediate Similarity	NPC184463
0.7802	Intermediate Similarity	NPC307411
0.7802	Intermediate Similarity	NPC473564
0.7802	Intermediate Similarity	NPC474032
0.7791	Intermediate Similarity	NPC47653
0.7778	Intermediate Similarity	NPC248602
0.7778	Intermediate Similarity	NPC160138
0.7766	Intermediate Similarity	NPC36954
0.7753	Intermediate Similarity	NPC137033
0.775	Intermediate Similarity	NPC218477
0.7742	Intermediate Similarity	NPC475912
0.7742	Intermediate Similarity	NPC273579
0.7742	Intermediate Similarity	NPC476300
0.7742	Intermediate Similarity	NPC288240
0.7742	Intermediate Similarity	NPC162205
0.7742	Intermediate Similarity	NPC295204
0.7727	Intermediate Similarity	NPC11620
0.7727	Intermediate Similarity	NPC475947
0.7717	Intermediate Similarity	NPC478004
0.7717	Intermediate Similarity	NPC158388
0.7717	Intermediate Similarity	NPC478003
0.7708	Intermediate Similarity	NPC473326
0.7692	Intermediate Similarity	NPC202672
0.7692	Intermediate Similarity	NPC153805
0.7692	Intermediate Similarity	NPC474471
0.7692	Intermediate Similarity	NPC58219
0.7692	Intermediate Similarity	NPC177629
0.7692	Intermediate Similarity	NPC227379
0.7674	Intermediate Similarity	NPC470149
0.7674	Intermediate Similarity	NPC470148
0.7667	Intermediate Similarity	NPC284902
0.7667	Intermediate Similarity	NPC469483
0.766	Intermediate Similarity	NPC474035
0.766	Intermediate Similarity	NPC81386
0.764	Intermediate Similarity	NPC474780
0.764	Intermediate Similarity	NPC474251
0.764	Intermediate Similarity	NPC288471
0.7614	Intermediate Similarity	NPC474291

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 NPC39167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	2232
0.2-0.3	3997
0.3-0.4	1953
0.4-0.5	561
0.5-0.6	195
0.6-0.7	37
0.7-0.8	1
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
0.7717	Intermediate Similarity	NPD46	Approved
0.7717	Intermediate Similarity	NPD6698	Approved
0.7353	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7838	Discovery
0.7115	Intermediate Similarity	NPD6686	Approved
0.7083	Intermediate Similarity	NPD7983	Approved
0.6832	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3197	Phase 1
0.6822	Remote Similarity	NPD6371	Approved
0.6809	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6633	Remote Similarity	NPD5785	Approved
0.6606	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5362	Discontinued
0.6596	Remote Similarity	NPD7154	Phase 3
0.6562	Remote Similarity	NPD4249	Approved
0.6535	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7638	Approved
0.6505	Remote Similarity	NPD4225	Approved
0.6489	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4756	Discovery
0.6458	Remote Similarity	NPD5363	Approved
0.6458	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6395	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD1695	Approved
0.6277	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD6053	Discontinued
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4790	Discontinued
0.6186	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5778	Approved
0.6176	Remote Similarity	NPD5779	Approved
0.6167	Remote Similarity	NPD7507	Approved
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7839	Suspended
0.6146	Remote Similarity	NPD5209	Approved
0.6146	Remote Similarity	NPD4270	Approved
0.6146	Remote Similarity	NPD6435	Approved
0.6146	Remote Similarity	NPD4269	Approved
0.6125	Remote Similarity	NPD3728	Approved
0.6125	Remote Similarity	NPD3730	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
0.6105	Remote Similarity	NPD4252	Approved
0.6102	Remote Similarity	NPD8513	Phase 3
0.6102	Remote Similarity	NPD8515	Approved
0.6102	Remote Similarity	NPD8516	Approved
0.6102	Remote Similarity	NPD8517	Approved
0.6082	Remote Similarity	NPD5332	Approved
0.6082	Remote Similarity	NPD5331	Approved
0.6064	Remote Similarity	NPD4271	Approved
0.6064	Remote Similarity	NPD4268	Approved
0.6061	Remote Similarity	NPD5786	Approved
0.6042	Remote Similarity	NPD5369	Approved
0.6034	Remote Similarity	NPD7115	Discovery
0.6024	Remote Similarity	NPD6109	Phase 1
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD7830	Approved
0.5981	Remote Similarity	NPD6648	Approved
0.5962	Remote Similarity	NPD5282	Discontinued
0.5949	Remote Similarity	NPD6927	Phase 3
0.5946	Remote Similarity	NPD6412	Phase 2
0.5938	Remote Similarity	NPD4819	Approved
0.5938	Remote Similarity	NPD5368	Approved
0.5938	Remote Similarity	NPD4821	Approved
0.5938	Remote Similarity	NPD4820	Approved
0.5938	Remote Similarity	NPD4822	Approved
0.593	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD3704	Approved
0.5882	Remote Similarity	NPD8294	Approved
0.5882	Remote Similarity	NPD8377	Approved
0.5872	Remote Similarity	NPD7632	Discontinued
0.5854	Remote Similarity	NPD8074	Phase 3
0.5847	Remote Similarity	NPD7328	Approved
0.5847	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD8380	Approved
0.5833	Remote Similarity	NPD8379	Approved
0.5833	Remote Similarity	NPD8378	Approved
0.5833	Remote Similarity	NPD8033	Approved
0.5833	Remote Similarity	NPD8296	Approved
0.5833	Remote Similarity	NPD8335	Approved
0.5814	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7748	Approved
0.5798	Remote Similarity	NPD7516	Approved
0.5776	Remote Similarity	NPD4632	Approved
0.5769	Remote Similarity	NPD7637	Suspended
0.575	Remote Similarity	NPD28	Approved
0.575	Remote Similarity	NPD29	Approved
0.5739	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7642	Approved
0.573	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.573	Remote Similarity	NPD7331	Phase 2
0.5728	Remote Similarity	NPD5370	Suspended
0.5728	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6101	Approved
0.5726	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD7641	Discontinued
0.5702	Remote Similarity	NPD8444	Approved
0.5701	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7492	Approved
0.569	Remote Similarity	NPD8297	Approved
0.568	Remote Similarity	NPD7736	Approved
0.5676	Remote Similarity	NPD6647	Phase 2
0.5664	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6421	Discontinued
0.5648	Remote Similarity	NPD6083	Phase 2
0.5648	Remote Similarity	NPD6084	Phase 2
0.5648	Remote Similarity	NPD7902	Approved
0.5647	Remote Similarity	NPD9119	Approved
0.5647	Remote Similarity	NPD69	Approved
0.5645	Remote Similarity	NPD6616	Approved
0.5645	Remote Similarity	NPD8273	Phase 1
0.5641	Remote Similarity	NPD8133	Approved
0.5631	Remote Similarity	NPD6903	Approved
0.563	Remote Similarity	NPD7500	Approved
0.562	Remote Similarity	NPD6054	Approved
0.562	Remote Similarity	NPD6319	Approved
0.5619	Remote Similarity	NPD7515	Phase 2
0.5619	Remote Similarity	NPD6411	Approved
0.5619	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD2204	Approved
0.56	Remote Similarity	NPD8293	Discontinued

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