NPASS Compound

Structure

NPC139683 OpenBabel07101719512D 56 62 0 0 1 0 0 0 0 0999 V2000 -7.4075 -3.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6754 -3.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5231 6.6837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1054 5.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7848 -3.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5023 -4.7462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8191 3.3620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5414 -2.1531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7041 4.9611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8624 -3.0520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1738 3.3109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4075 -1.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2919 4.1521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5534 -2.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4307 2.6418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4075 1.3469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2735 0.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3328 2.0238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0717 1.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5608 0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8094 -0.1531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5414 -3.1531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1109 5.8747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1933 -3.7951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1249 3.0019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4075 -0.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8852 3.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2226 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5414 0.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0662 1.5160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4839 2.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8094 0.8469 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2735 -0.1531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5897 1.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8698 -0.8226 0.0000 C 0 0 0 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 -2.8907 3.1341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2007 -1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4894 2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5414 -0.1531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4730 2.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6754 1.3469 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1395 -0.6531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7976 0.3765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 -1.0305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3029 3.9431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5097 -2.5168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9016 2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8681 3.6710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6754 -0.6531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4675 2.3250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 53 1 0 0 0 0 8 12 1 0 0 0 0 8 22 2 0 0 0 0 9 13 1 0 0 0 0 9 23 2 0 0 0 0 10 14 1 0 0 0 0 10 24 2 0 0 0 0 11 15 2 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 27 1 0 0 0 0 16 17 2 0 0 0 0 16 30 1 0 0 0 0 17 35 1 0 0 0 0 18 25 2 0 0 0 0 18 36 1 0 0 0 0 19 31 2 0 0 0 0 19 33 1 0 0 0 0 20 32 1 0 0 0 0 20 37 2 0 0 0 0 21 54 1 0 0 0 0 25 53 1 0 0 0 0 26 35 2 0 0 0 0 26 42 1 0 0 0 0 27 36 2 0 0 0 0 27 46 1 0 0 0 0 28 39 1 0 0 0 0 28 43 2 0 0 0 0 29 40 2 0 0 0 0 29 44 1 0 0 0 0 30 42 2 0 0 0 0 31 34 1 0 0 0 0 31 43 1 0 0 0 0 32 38 1 0 0 0 0 32 44 2 0 0 0 0 33 39 2 0 0 0 0 33 41 1 0 0 0 0 34 21 1 6 0 0 0 34 45 1 0 0 0 0 35 47 1 0 0 0 0 36 48 1 0 0 0 0 37 40 1 0 0 0 0 37 49 1 0 0 0 0 38 41 1 0 0 0 0 38 46 2 0 0 0 0 39 50 1 0 0 0 0 40 51 1 0 0 0 0 41 52 2 0 0 0 0 42 54 1 0 0 0 0 43 55 1 0 0 0 0 44 56 1 0 0 0 0 45 30 1 6 0 0 0 45 55 1 0 0 0 0 46 56 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	758.31
Volume:	787.359
LogP:	10.399
LogD:	4.977
LogS:	-2.532
# Rotatable Bonds:	10
TPSA:	159.05
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.053
Synthetic Accessibility Score:	4.777
Fsp3:	0.283
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.844
MDCK Permeability:	1.104154307540739e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.4
Human Intestinal Absorption (HIA):	0.439
20% Bioavailability (F20%):	0.556
30% Bioavailability (F30%):	0.406

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	104.71707153320312%
Volume Distribution (VD):	0.317
Pgp-substrate:	12.119709968566895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.273
CYP2C19-inhibitor:	0.839
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.665
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	8.098
Half-life (T1/2):	0.011

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.563
Rat Oral Acute Toxicity:	0.919
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.926
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.835
Respiratory Toxicity:	0.083

Download Data

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

Natural Product: NPC139683

Natural Product ID:	NPC139683
*Common Name:**	Lespeflorin J2
IUPAC Name:	[(6aR,11aR)-3,9-dihydroxy-4,10-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-8-yl]-[5,6-dihydroxy-2-(2-hydroxy-4-methoxyphenyl)-7-(3-methylbut-2-enyl)-1-benzofuran-3-yl]methanone
Synonyms:	Lespeflorin J2
Standard InCHIKey:	PVSGPDNIJGJLPD-LEEIDUJMSA-N
Standard InCHI:	InChI=1S/C46H46O10/c1-22(2)8-12-26-35(47)17-16-30-42(26)54-21-34-31-19-33(39(50)28(13-9-23(3)4)43(31)55-45(30)34)41(52)38-32-20-37(49)40(51)29(14-10-24(5)6)44(32)56-46(38)27-15-11-25(53-7)18-36(27)48/h8-11,15-20,34,45,47-51H,12-14,21H2,1-7H3/t34-,45-/m0/s1
SMILES:	CC(=CCc1c(ccc2c1OC[C@H]1c3cc(c(c(CC=C(C)C)c3O[C@@H]21)O)C(=O)c1c2cc(c(c(CC=C(C)C)c2oc1c1ccc(cc1O)OC)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL556752
PubChem CID:	25243077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	52800.0	nM	PMID[494666]

☑ 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 NPC139683 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	470
0.1-0.2	1674
0.2-0.3	3611
0.3-0.4	9666
0.4-0.5	9186
0.5-0.6	3946
0.6-0.7	5448
0.7-0.8	5241
0.8-0.85	2444
0.85-0.9	965
0.9-0.95	42
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC73929
1.0	High Similarity	NPC47905
0.9941	High Similarity	NPC304322
0.9235	High Similarity	NPC50394
0.9186	High Similarity	NPC248593
0.9186	High Similarity	NPC28589
0.9186	High Similarity	NPC174700
0.9176	High Similarity	NPC277480
0.9148	High Similarity	NPC150977
0.9118	High Similarity	NPC37183
0.9086	High Similarity	NPC475783
0.907	High Similarity	NPC53252
0.9064	High Similarity	NPC224851
0.9064	High Similarity	NPC320741
0.9064	High Similarity	NPC171985
0.9059	High Similarity	NPC38591
0.9034	High Similarity	NPC185275
0.9034	High Similarity	NPC324742
0.9023	High Similarity	NPC261471
0.9023	High Similarity	NPC310794
0.9023	High Similarity	NPC473834
0.9	High Similarity	NPC473012
0.8977	High Similarity	NPC471789
0.8977	High Similarity	NPC265380
0.8971	High Similarity	NPC300657
0.896	High Similarity	NPC107627
0.8953	High Similarity	NPC251336
0.8947	High Similarity	NPC473009
0.8941	High Similarity	NPC312273
0.8941	High Similarity	NPC301256
0.892	High Similarity	NPC164384
0.892	High Similarity	NPC156955
0.8914	High Similarity	NPC37606
0.8908	High Similarity	NPC131866
0.8908	High Similarity	NPC218533
0.8908	High Similarity	NPC78830
0.8902	High Similarity	NPC247973
0.8902	High Similarity	NPC286230
0.8902	High Similarity	NPC253730
0.8895	High Similarity	NPC259757
0.8895	High Similarity	NPC473010
0.8895	High Similarity	NPC291110
0.8857	High Similarity	NPC472454
0.8857	High Similarity	NPC257667
0.8857	High Similarity	NPC186847
0.8851	High Similarity	NPC300307
0.8851	High Similarity	NPC475212
0.8844	High Similarity	NPC272560
0.8837	High Similarity	NPC473313
0.8837	High Similarity	NPC472278
0.8837	High Similarity	NPC329669
0.8824	High Similarity	NPC40583
0.8814	High Similarity	NPC8127
0.8814	High Similarity	NPC49667
0.8807	High Similarity	NPC149846
0.88	High Similarity	NPC476365
0.88	High Similarity	NPC102277
0.88	High Similarity	NPC180768
0.88	High Similarity	NPC279209
0.8793	High Similarity	NPC243877
0.8793	High Similarity	NPC14662
0.8793	High Similarity	NPC86477
0.8786	High Similarity	NPC300053
0.8786	High Similarity	NPC477840
0.8786	High Similarity	NPC169471
0.8779	High Similarity	NPC312056
0.8779	High Similarity	NPC84515
0.8771	High Similarity	NPC97523
0.8757	High Similarity	NPC99591
0.8757	High Similarity	NPC287243
0.875	High Similarity	NPC289396
0.875	High Similarity	NPC81332
0.875	High Similarity	NPC4200
0.875	High Similarity	NPC212038
0.875	High Similarity	NPC271848
0.875	High Similarity	NPC262580
0.8736	High Similarity	NPC473618
0.8736	High Similarity	NPC119589
0.8736	High Similarity	NPC173292
0.8736	High Similarity	NPC128293
0.8736	High Similarity	NPC53640
0.8728	High Similarity	NPC273959
0.8721	High Similarity	NPC142252
0.8721	High Similarity	NPC472275
0.8721	High Similarity	NPC188486
0.8721	High Similarity	NPC266314
0.8713	High Similarity	NPC15815
0.8708	High Similarity	NPC101991
0.8708	High Similarity	NPC216307
0.8701	High Similarity	NPC216842
0.8701	High Similarity	NPC82217
0.8701	High Similarity	NPC476640
0.8701	High Similarity	NPC117450
0.8701	High Similarity	NPC98583
0.8701	High Similarity	NPC65885
0.8693	High Similarity	NPC472276
0.8693	High Similarity	NPC103307
0.8693	High Similarity	NPC120220
0.8686	High Similarity	NPC476459
0.8686	High Similarity	NPC260266
0.8681	High Similarity	NPC179947
0.8678	High Similarity	NPC473286
0.8678	High Similarity	NPC39306
0.8678	High Similarity	NPC326520
0.8678	High Similarity	NPC472277
0.8678	High Similarity	NPC29411
0.8674	High Similarity	NPC154527
0.8671	High Similarity	NPC220912
0.8671	High Similarity	NPC476247
0.8671	High Similarity	NPC477841
0.8671	High Similarity	NPC473011
0.8671	High Similarity	NPC219927
0.8671	High Similarity	NPC81679
0.8667	High Similarity	NPC47883
0.8663	High Similarity	NPC98023
0.8663	High Similarity	NPC195136
0.8663	High Similarity	NPC304839
0.8663	High Similarity	NPC220582
0.8663	High Similarity	NPC188967
0.8663	High Similarity	NPC226462
0.8655	High Similarity	NPC257166
0.8655	High Similarity	NPC1796
0.8655	High Similarity	NPC287789
0.8655	High Similarity	NPC271741
0.8652	High Similarity	NPC227906
0.8647	High Similarity	NPC37253
0.8647	High Similarity	NPC79375
0.8647	High Similarity	NPC113906
0.8644	High Similarity	NPC477529
0.8644	High Similarity	NPC230619
0.8644	High Similarity	NPC472584
0.8644	High Similarity	NPC54098
0.8644	High Similarity	NPC100251
0.8644	High Similarity	NPC121333
0.8644	High Similarity	NPC307286
0.8641	High Similarity	NPC264302
0.8636	High Similarity	NPC152477
0.8636	High Similarity	NPC288813
0.8636	High Similarity	NPC242395
0.8629	High Similarity	NPC170245
0.8629	High Similarity	NPC82330
0.8629	High Similarity	NPC235610
0.8629	High Similarity	NPC43065
0.8629	High Similarity	NPC120593
0.8626	High Similarity	NPC226725
0.8621	High Similarity	NPC124038
0.8621	High Similarity	NPC472281
0.8621	High Similarity	NPC18100
0.8621	High Similarity	NPC133065
0.8621	High Similarity	NPC159508
0.8621	High Similarity	NPC205265
0.8621	High Similarity	NPC272064
0.8619	High Similarity	NPC132111
0.8619	High Similarity	NPC471842
0.8619	High Similarity	NPC321916
0.8613	High Similarity	NPC74854
0.8613	High Similarity	NPC45124
0.8613	High Similarity	NPC30655
0.8613	High Similarity	NPC231758
0.8613	High Similarity	NPC228383
0.8613	High Similarity	NPC158188
0.8611	High Similarity	NPC473785
0.8611	High Similarity	NPC121888
0.8611	High Similarity	NPC183843
0.8605	High Similarity	NPC190487
0.8605	High Similarity	NPC185258
0.8605	High Similarity	NPC196879
0.8605	High Similarity	NPC154304
0.8605	High Similarity	NPC51247
0.8605	High Similarity	NPC210459
0.8605	High Similarity	NPC16935
0.8605	High Similarity	NPC95936
0.8605	High Similarity	NPC250214
0.8605	High Similarity	NPC105584
0.8605	High Similarity	NPC469658
0.8605	High Similarity	NPC172770
0.8603	High Similarity	NPC471841
0.8603	High Similarity	NPC478050
0.8596	High Similarity	NPC59491
0.8596	High Similarity	NPC198489
0.8596	High Similarity	NPC32867
0.8596	High Similarity	NPC24748
0.8596	High Similarity	NPC309648
0.8596	High Similarity	NPC61112
0.8596	High Similarity	NPC69531
0.8588	High Similarity	NPC121568
0.8588	High Similarity	NPC1477
0.8588	High Similarity	NPC298692
0.8588	High Similarity	NPC213896
0.8588	High Similarity	NPC213608
0.8588	High Similarity	NPC190351
0.8588	High Similarity	NPC192083
0.8588	High Similarity	NPC476641
0.858	High Similarity	NPC295082
0.858	High Similarity	NPC470704
0.8571	High Similarity	NPC474591
0.8571	High Similarity	NPC45449
0.8571	High Similarity	NPC38914
0.8571	High Similarity	NPC108433
0.8571	High Similarity	NPC318119

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 NPC139683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	931
0.2-0.3	1814
0.3-0.4	2708
0.4-0.5	1863
0.5-0.6	932
0.6-0.7	330
0.7-0.8	125
0.8-0.85	37
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD2393	Clinical (unspecified phase)
0.8555	High Similarity	NPD5494	Approved
0.8466	Intermediate Similarity	NPD6166	Phase 2
0.8466	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6959	Discontinued
0.8314	Intermediate Similarity	NPD1934	Approved
0.8276	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD2801	Approved
0.8258	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD7473	Discontinued
0.8177	Intermediate Similarity	NPD7074	Phase 3
0.8172	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3882	Suspended
0.8167	Intermediate Similarity	NPD3818	Discontinued
0.8122	Intermediate Similarity	NPD5844	Phase 1
0.8122	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD4380	Phase 2
0.8087	Intermediate Similarity	NPD6559	Discontinued
0.8077	Intermediate Similarity	NPD7472	Approved
0.8068	Intermediate Similarity	NPD7768	Phase 2
0.8057	Intermediate Similarity	NPD7819	Suspended
0.8045	Intermediate Similarity	NPD6232	Discontinued
0.8023	Intermediate Similarity	NPD3749	Approved
0.8023	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD3926	Phase 2
0.7989	Intermediate Similarity	NPD7251	Discontinued
0.7953	Intermediate Similarity	NPD1511	Approved
0.7946	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD7808	Phase 3
0.7943	Intermediate Similarity	NPD7411	Suspended
0.7935	Intermediate Similarity	NPD6797	Phase 2
0.7923	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD1247	Approved
0.7861	Intermediate Similarity	NPD1512	Approved
0.7853	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD8313	Approved
0.7807	Intermediate Similarity	NPD8312	Approved
0.7803	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD1549	Phase 2
0.7709	Intermediate Similarity	NPD3817	Phase 2
0.7706	Intermediate Similarity	NPD2344	Approved
0.7706	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7611	Intermediate Similarity	NPD5402	Approved
0.7598	Intermediate Similarity	NPD6801	Discontinued
0.7592	Intermediate Similarity	NPD8434	Phase 2
0.7582	Intermediate Similarity	NPD6234	Discontinued
0.7582	Intermediate Similarity	NPD919	Approved
0.7574	Intermediate Similarity	NPD8151	Discontinued
0.7544	Intermediate Similarity	NPD2796	Approved
0.7543	Intermediate Similarity	NPD7390	Discontinued
0.7529	Intermediate Similarity	NPD2309	Approved
0.7514	Intermediate Similarity	NPD2800	Approved
0.7514	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD1510	Phase 2
0.7463	Intermediate Similarity	NPD7870	Phase 2
0.7463	Intermediate Similarity	NPD7871	Phase 2
0.7437	Intermediate Similarity	NPD6779	Approved
0.7437	Intermediate Similarity	NPD6780	Approved
0.7437	Intermediate Similarity	NPD6781	Approved
0.7437	Intermediate Similarity	NPD6782	Approved
0.7437	Intermediate Similarity	NPD6776	Approved
0.7437	Intermediate Similarity	NPD6777	Approved
0.7437	Intermediate Similarity	NPD6778	Approved
0.7413	Intermediate Similarity	NPD7697	Approved
0.7413	Intermediate Similarity	NPD7696	Phase 3
0.7413	Intermediate Similarity	NPD7698	Approved
0.7413	Intermediate Similarity	NPD7435	Discontinued
0.7409	Intermediate Similarity	NPD8150	Discontinued
0.7405	Intermediate Similarity	NPD7199	Phase 2
0.7401	Intermediate Similarity	NPD2533	Approved
0.7401	Intermediate Similarity	NPD2534	Approved
0.7401	Intermediate Similarity	NPD2532	Approved
0.7401	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD4965	Approved
0.7377	Intermediate Similarity	NPD4966	Approved
0.7377	Intermediate Similarity	NPD4967	Phase 2
0.7366	Intermediate Similarity	NPD3787	Discontinued
0.7363	Intermediate Similarity	NPD8455	Phase 2
0.7353	Intermediate Similarity	NPD1240	Approved
0.7353	Intermediate Similarity	NPD943	Approved
0.7353	Intermediate Similarity	NPD7701	Phase 2
0.7345	Intermediate Similarity	NPD6799	Approved
0.7341	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD3226	Approved
0.733	Intermediate Similarity	NPD7783	Phase 2
0.733	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7801	Approved
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD1243	Approved
0.7314	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6599	Discontinued
0.7288	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7267	Intermediate Similarity	NPD1607	Approved
0.7264	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7700	Phase 2
0.725	Intermediate Similarity	NPD7699	Phase 2
0.724	Intermediate Similarity	NPD7685	Pre-registration
0.724	Intermediate Similarity	NPD7240	Approved
0.7235	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5403	Approved
0.7213	Intermediate Similarity	NPD37	Approved
0.7207	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6823	Phase 2
0.7188	Intermediate Similarity	NPD5953	Discontinued
0.7186	Intermediate Similarity	NPD6534	Approved
0.7186	Intermediate Similarity	NPD6535	Approved
0.7184	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3750	Approved
0.7174	Intermediate Similarity	NPD5761	Phase 2
0.7174	Intermediate Similarity	NPD5760	Phase 2
0.7168	Intermediate Similarity	NPD6651	Approved
0.7159	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7680	Approved
0.7157	Intermediate Similarity	NPD4287	Approved
0.7151	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4908	Phase 1
0.7111	Intermediate Similarity	NPD5401	Approved
0.711	Intermediate Similarity	NPD230	Phase 1
0.7086	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD7286	Phase 2
0.7056	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD6099	Approved
0.7045	Intermediate Similarity	NPD6100	Approved
0.7043	Intermediate Similarity	NPD2296	Approved
0.7039	Intermediate Similarity	NPD8320	Phase 1
0.7039	Intermediate Similarity	NPD8319	Approved
0.7039	Intermediate Similarity	NPD6190	Approved
0.7037	Intermediate Similarity	NPD8127	Discontinued
0.7023	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7907	Approved
0.7018	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4360	Phase 2
0.7015	Intermediate Similarity	NPD4363	Phase 3
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD5711	Approved
0.6995	Remote Similarity	NPD1653	Approved
0.6989	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4628	Phase 3
0.6983	Remote Similarity	NPD8166	Discontinued
0.6965	Remote Similarity	NPD6213	Phase 3
0.6965	Remote Similarity	NPD6212	Phase 3
0.6965	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5404	Approved
0.6949	Remote Similarity	NPD5405	Approved
0.6949	Remote Similarity	NPD5406	Approved
0.6949	Remote Similarity	NPD1551	Phase 2
0.6949	Remote Similarity	NPD5408	Approved
0.6936	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6844	Discontinued
0.6935	Remote Similarity	NPD6279	Approved
0.6935	Remote Similarity	NPD6280	Approved
0.6931	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6808	Phase 2
0.691	Remote Similarity	NPD1471	Phase 3
0.6893	Remote Similarity	NPD3748	Approved
0.689	Remote Similarity	NPD7584	Approved
0.6889	Remote Similarity	NPD7003	Approved
0.6889	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3027	Phase 3
0.6864	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8059	Phase 3
0.686	Remote Similarity	NPD2861	Phase 2
0.6856	Remote Similarity	NPD7177	Discontinued
0.6853	Remote Similarity	NPD7549	Discontinued
0.6852	Remote Similarity	NPD4665	Approved
0.6852	Remote Similarity	NPD4111	Phase 1
0.6839	Remote Similarity	NPD2313	Discontinued
0.6818	Remote Similarity	NPD447	Suspended
0.6814	Remote Similarity	NPD4361	Phase 2
0.6814	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8285	Discontinued
0.6793	Remote Similarity	NPD6273	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