NPASS Compound

Structure

NPC91288 OpenBabel07101719252D 31 34 0 0 1 0 0 0 0 0999 V2000 2.2272 -1.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 5.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4725 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6065 2.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4725 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7405 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6065 4.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8744 4.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0084 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5443 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8963 -0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7405 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 4.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4103 4.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5443 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4103 2.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2764 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -1.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 5.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 2.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4103 5.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 -0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1988 1.8917 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 13 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 11 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 25 2 0 0 0 0 13 29 1 0 0 0 0 15 18 1 0 0 0 0 15 26 2 0 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 19 2 0 0 0 0 17 30 1 0 0 0 0 18 21 2 0 0 0 0 19 21 1 0 0 0 0 20 19 1 6 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 29 1 1 0 0 0 23 30 1 6 0 0 0 23 31 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.15
Volume:	427.238
LogP:	3.734
LogD:	2.913
LogS:	-4.856
# Rotatable Bonds:	6
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	3.866
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.722
MDCK Permeability:	2.1849586119060405e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.214
Plasma Protein Binding (PPB):	95.50780487060547%
Volume Distribution (VD):	0.787
Pgp-substrate:	4.074899673461914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.391
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.244
CYP2C19-substrate:	0.415
CYP2C9-inhibitor:	0.799
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.669
CYP2D6-substrate:	0.312
CYP3A4-inhibitor:	0.627
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	1.602
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.28
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.491
Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.349
Carcinogencity:	0.51
Eye Corrosion:	0.003
Eye Irritation:	0.407
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC91288

Natural Product ID:	NPC91288
*Common Name:**	Tephropurpurin
IUPAC Name:	[(1R,3aS,8bR)-8-hydroxy-6-methoxy-2,2-dimethyl-7-[(E)-3-phenylprop-2-enoyl]-3a,8b-dihydro-1H-furo[2,3-b][1]benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	BICKLHZENLKHGI-LXEULODHSA-N
Standard InCHI:	InChI=1S/C24H24O7/c1-13(25)29-22-20-19-17(30-23(20)31-24(22,2)3)12-16(28-4)18(21(19)27)15(26)11-10-14-8-6-5-7-9-14/h5-12,20,22-23,27H,1-4H3/b11-10+/t20-,22-,23+/m1/s1
SMILES:	CC(=O)O[C@@H]1[C@H]2c3c(cc(c(C(=O)/C=C/c4ccccc4)c3O)OC)O[C@H]2OC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457943
PubChem CID:	10047971
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003542] Furanochalcones

*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
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10814365]
NPO22730	Indigofera spicata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23895019]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26476665]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322358]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22730	Indigofera spicata	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	2
Others	4

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.15	uM	PMID[468267]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13400.0	nM	PMID[468267]
NPT2	Others	Unspecified		Ratio	=	89.0	n.a.	PMID[468267]
NPT2	Others	Unspecified		Ratio	=	23.9	n.a.	PMID[468268]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18100.0	nM	PMID[468268]
NPT2	Others	Unspecified		CD	=	0.8	uM	PMID[468268]

☑ 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 NPC91288 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	347
0.1-0.2	1472
0.2-0.3	3112
0.3-0.4	7259
0.4-0.5	10999
0.5-0.6	4761
0.6-0.7	5467
0.7-0.8	6892
0.8-0.85	2006
0.85-0.9	373
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC471286
0.9551	High Similarity	NPC74749
0.9551	High Similarity	NPC43971
0.9551	High Similarity	NPC19554
0.9487	High Similarity	NPC50430
0.9351	High Similarity	NPC318424
0.9308	High Similarity	NPC310603
0.9308	High Similarity	NPC93215
0.9245	High Similarity	NPC92589
0.9236	High Similarity	NPC211482
0.9236	High Similarity	NPC476652
0.9161	High Similarity	NPC472421
0.9114	High Similarity	NPC469936
0.9114	High Similarity	NPC474609
0.9114	High Similarity	NPC129053
0.9114	High Similarity	NPC109967
0.9114	High Similarity	NPC321372
0.9114	High Similarity	NPC474738
0.9114	High Similarity	NPC78554
0.9114	High Similarity	NPC475797
0.9103	High Similarity	NPC474744
0.9103	High Similarity	NPC472423
0.9103	High Similarity	NPC474772
0.9057	High Similarity	NPC23817
0.9057	High Similarity	NPC43638
0.9051	High Similarity	NPC279218
0.9051	High Similarity	NPC108937
0.9045	High Similarity	NPC327269
0.9045	High Similarity	NPC31627
0.9045	High Similarity	NPC473996
0.9045	High Similarity	NPC476238
0.9	High Similarity	NPC470607
0.8994	High Similarity	NPC149368
0.8994	High Similarity	NPC265480
0.8994	High Similarity	NPC470625
0.8994	High Similarity	NPC127406
0.8981	High Similarity	NPC472580
0.8981	High Similarity	NPC471675
0.8981	High Similarity	NPC290671
0.8981	High Similarity	NPC472636
0.897	High Similarity	NPC120220
0.8968	High Similarity	NPC14875
0.8963	High Similarity	NPC320789
0.8944	High Similarity	NPC472320
0.8944	High Similarity	NPC271479
0.8944	High Similarity	NPC200708
0.8938	High Similarity	NPC470606
0.8931	High Similarity	NPC469934
0.8931	High Similarity	NPC99233
0.8924	High Similarity	NPC285623
0.8924	High Similarity	NPC477957
0.8917	High Similarity	NPC180351
0.8916	High Similarity	NPC472584
0.891	High Similarity	NPC168085
0.8896	High Similarity	NPC183672
0.8889	High Similarity	NPC94155
0.8882	High Similarity	NPC43761
0.8882	High Similarity	NPC308265
0.8882	High Similarity	NPC40583
0.8882	High Similarity	NPC73511
0.8875	High Similarity	NPC17521
0.8868	High Similarity	NPC168805
0.8868	High Similarity	NPC121910
0.8868	High Similarity	NPC106625
0.8862	High Similarity	NPC98776
0.8861	High Similarity	NPC23253
0.8861	High Similarity	NPC471676
0.8861	High Similarity	NPC244577
0.8861	High Similarity	NPC190217
0.8861	High Similarity	NPC472420
0.8861	High Similarity	NPC263384
0.8861	High Similarity	NPC472422
0.8855	High Similarity	NPC76047
0.8854	High Similarity	NPC317492
0.8848	High Similarity	NPC476459
0.8841	High Similarity	NPC475979
0.8841	High Similarity	NPC72016
0.8841	High Similarity	NPC294722
0.8834	High Similarity	NPC125991
0.8834	High Similarity	NPC259834
0.8834	High Similarity	NPC44947
0.8834	High Similarity	NPC131745
0.883	High Similarity	NPC106700
0.8827	High Similarity	NPC306978
0.8827	High Similarity	NPC220582
0.8827	High Similarity	NPC304839
0.882	High Similarity	NPC156457
0.882	High Similarity	NPC313163
0.882	High Similarity	NPC258035
0.882	High Similarity	NPC197896
0.882	High Similarity	NPC161650
0.882	High Similarity	NPC122809
0.882	High Similarity	NPC161749
0.8812	High Similarity	NPC470603
0.8812	High Similarity	NPC470604
0.8812	High Similarity	NPC474542
0.8812	High Similarity	NPC470605
0.8805	High Similarity	NPC259767
0.8805	High Similarity	NPC259182
0.8805	High Similarity	NPC256141
0.8805	High Similarity	NPC121001
0.8805	High Similarity	NPC88484
0.8802	High Similarity	NPC475825
0.8802	High Similarity	NPC223375
0.8797	High Similarity	NPC474735
0.8797	High Similarity	NPC476509
0.8797	High Similarity	NPC470908
0.8797	High Similarity	NPC327059
0.8797	High Similarity	NPC321896
0.8797	High Similarity	NPC321387
0.8797	High Similarity	NPC106025
0.8797	High Similarity	NPC214454
0.8797	High Similarity	NPC476185
0.8797	High Similarity	NPC477240
0.879	High Similarity	NPC39195
0.8788	High Similarity	NPC53640
0.8782	High Similarity	NPC316769
0.8782	High Similarity	NPC477955
0.878	High Similarity	NPC179198
0.878	High Similarity	NPC278419
0.878	High Similarity	NPC124155
0.878	High Similarity	NPC257566
0.878	High Similarity	NPC472582
0.878	High Similarity	NPC66087
0.8773	High Similarity	NPC175513
0.8773	High Similarity	NPC303913
0.8773	High Similarity	NPC47923
0.8773	High Similarity	NPC97812
0.8766	High Similarity	NPC171870
0.8765	High Similarity	NPC104677
0.8765	High Similarity	NPC311574
0.8765	High Similarity	NPC264932
0.8758	High Similarity	NPC170475
0.8758	High Similarity	NPC45165
0.8758	High Similarity	NPC206378
0.8757	High Similarity	NPC475233
0.8757	High Similarity	NPC324220
0.8757	High Similarity	NPC312630
0.875	High Similarity	NPC223701
0.875	High Similarity	NPC472583
0.875	High Similarity	NPC87304
0.875	High Similarity	NPC268950
0.875	High Similarity	NPC108706
0.875	High Similarity	NPC211158
0.875	High Similarity	NPC78021
0.875	High Similarity	NPC7989
0.8743	High Similarity	NPC477571
0.8743	High Similarity	NPC477572
0.8743	High Similarity	NPC477573
0.8743	High Similarity	NPC298778
0.8743	High Similarity	NPC212748
0.8742	High Similarity	NPC309512
0.8742	High Similarity	NPC471291
0.8742	High Similarity	NPC295650
0.8742	High Similarity	NPC148945
0.8742	High Similarity	NPC312549
0.8742	High Similarity	NPC204561
0.8742	High Similarity	NPC78835
0.8742	High Similarity	NPC317715
0.8742	High Similarity	NPC316960
0.8742	High Similarity	NPC209142
0.8742	High Similarity	NPC471677
0.8734	High Similarity	NPC164205
0.8734	High Similarity	NPC473016
0.8734	High Similarity	NPC104172
0.8734	High Similarity	NPC88886
0.8734	High Similarity	NPC104236
0.8728	High Similarity	NPC282636
0.8728	High Similarity	NPC294863
0.8727	High Similarity	NPC300053
0.8726	High Similarity	NPC47388
0.8726	High Similarity	NPC470670
0.8726	High Similarity	NPC308200
0.8726	High Similarity	NPC473133
0.8726	High Similarity	NPC202494
0.872	High Similarity	NPC472876
0.872	High Similarity	NPC190450
0.872	High Similarity	NPC150164
0.8718	High Similarity	NPC131568
0.8718	High Similarity	NPC209040
0.8718	High Similarity	NPC470857
0.8718	High Similarity	NPC473015
0.8718	High Similarity	NPC271288
0.8718	High Similarity	NPC316535
0.8718	High Similarity	NPC473013
0.8718	High Similarity	NPC469953
0.8718	High Similarity	NPC131579
0.8712	High Similarity	NPC114147
0.8712	High Similarity	NPC328102
0.8712	High Similarity	NPC172687
0.871	High Similarity	NPC472344
0.871	High Similarity	NPC130206
0.8704	High Similarity	NPC6985
0.8704	High Similarity	NPC288084
0.8704	High Similarity	NPC210048
0.8698	High Similarity	NPC474345
0.8698	High Similarity	NPC68381
0.8696	High Similarity	NPC169248
0.8696	High Similarity	NPC92395
0.8696	High Similarity	NPC72649

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 NPC91288 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	854
0.2-0.3	1735
0.3-0.4	2518
0.4-0.5	2096
0.5-0.6	1076
0.6-0.7	372
0.7-0.8	169
0.8-0.85	27
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.882	High Similarity	NPD4381	Clinical (unspecified phase)
0.8704	High Similarity	NPD7075	Discontinued
0.8639	High Similarity	NPD6559	Discontinued
0.8634	High Similarity	NPD7096	Clinical (unspecified phase)
0.8623	High Similarity	NPD3818	Discontinued
0.8571	High Similarity	NPD7804	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD6801	Discontinued
0.8447	Intermediate Similarity	NPD4380	Phase 2
0.8418	Intermediate Similarity	NPD6799	Approved
0.8405	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7819	Suspended
0.8395	Intermediate Similarity	NPD7411	Suspended
0.8354	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8304	Intermediate Similarity	NPD7074	Phase 3
0.8269	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD5494	Approved
0.825	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7054	Approved
0.8232	Intermediate Similarity	NPD1934	Approved
0.8205	Intermediate Similarity	NPD2796	Approved
0.8198	Intermediate Similarity	NPD7472	Approved
0.8193	Intermediate Similarity	NPD7768	Phase 2
0.8193	Intermediate Similarity	NPD3882	Suspended
0.8176	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6797	Phase 2
0.8148	Intermediate Similarity	NPD920	Approved
0.8144	Intermediate Similarity	NPD3749	Approved
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.8137	Intermediate Similarity	NPD2534	Approved
0.8137	Intermediate Similarity	NPD2533	Approved
0.8137	Intermediate Similarity	NPD2532	Approved
0.8117	Intermediate Similarity	NPD1240	Approved
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8057	Intermediate Similarity	NPD7808	Phase 3
0.805	Intermediate Similarity	NPD1243	Approved
0.805	Intermediate Similarity	NPD2800	Approved
0.805	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2799	Discontinued
0.8025	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD3817	Phase 2
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8013	Intermediate Similarity	NPD1607	Approved
0.8012	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6234	Discontinued
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD4965	Approved
0.7976	Intermediate Similarity	NPD4967	Phase 2
0.7976	Intermediate Similarity	NPD4966	Approved
0.7975	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD1551	Phase 2
0.7964	Intermediate Similarity	NPD2801	Approved
0.7953	Intermediate Similarity	NPD6232	Discontinued
0.7939	Intermediate Similarity	NPD7458	Discontinued
0.7931	Intermediate Similarity	NPD5844	Phase 1
0.7927	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD5403	Approved
0.791	Intermediate Similarity	NPD8312	Approved
0.791	Intermediate Similarity	NPD8313	Approved
0.7895	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD7199	Phase 2
0.7882	Intermediate Similarity	NPD919	Approved
0.7871	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6166	Phase 2
0.7861	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1511	Approved
0.7841	Intermediate Similarity	NPD5953	Discontinued
0.7829	Intermediate Similarity	NPD7286	Phase 2
0.7811	Intermediate Similarity	NPD5402	Approved
0.7805	Intermediate Similarity	NPD5401	Approved
0.7803	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD37	Approved
0.7771	Intermediate Similarity	NPD7228	Approved
0.7758	Intermediate Similarity	NPD1512	Approved
0.7753	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2344	Approved
0.7688	Intermediate Similarity	NPD3748	Approved
0.7647	Intermediate Similarity	NPD8455	Phase 2
0.7644	Intermediate Similarity	NPD7584	Approved
0.7643	Intermediate Similarity	NPD2313	Discontinued
0.7619	Intermediate Similarity	NPD3226	Approved
0.7593	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1247	Approved
0.7582	Intermediate Similarity	NPD8434	Phase 2
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7578	Intermediate Similarity	NPD7033	Discontinued
0.7562	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1203	Approved
0.7543	Intermediate Similarity	NPD5710	Approved
0.7543	Intermediate Similarity	NPD5711	Approved
0.7542	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.7515	Intermediate Similarity	NPD2309	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.7485	Intermediate Similarity	NPD6005	Phase 3
0.7485	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6002	Phase 3
0.7485	Intermediate Similarity	NPD2346	Discontinued
0.7485	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6004	Phase 3
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.7472	Intermediate Similarity	NPD3751	Discontinued
0.7447	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7229	Phase 3
0.7442	Intermediate Similarity	NPD1465	Phase 2
0.7427	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7585	Approved
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3268	Approved
0.7403	Intermediate Similarity	NPD7240	Approved
0.7398	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7783	Phase 2
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7697	Approved
0.7391	Intermediate Similarity	NPD5124	Phase 1
0.7391	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7930	Approved
0.7374	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7583	Approved
0.7358	Intermediate Similarity	NPD7870	Phase 2
0.7358	Intermediate Similarity	NPD7871	Phase 2
0.7355	Intermediate Similarity	NPD9717	Approved
0.7353	Intermediate Similarity	NPD1653	Approved
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7874	Approved
0.7345	Intermediate Similarity	NPD3787	Discontinued
0.734	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD4360	Phase 2
0.7325	Intermediate Similarity	NPD2797	Approved
0.7317	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD6099	Approved
0.7312	Intermediate Similarity	NPD3764	Approved
0.731	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4361	Phase 2
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.7284	Intermediate Similarity	NPD230	Phase 1
0.7284	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD447	Suspended
0.7268	Intermediate Similarity	NPD8320	Phase 1
0.7268	Intermediate Similarity	NPD8319	Approved
0.7263	Intermediate Similarity	NPD2403	Approved
0.7256	Intermediate Similarity	NPD4308	Phase 3
0.7256	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6823	Phase 2
0.7249	Intermediate Similarity	NPD6534	Approved
0.7249	Intermediate Similarity	NPD6535	Approved
0.7245	Intermediate Similarity	NPD7701	Phase 2
0.7244	Intermediate Similarity	NPD1608	Approved
0.7241	Intermediate Similarity	NPD5761	Phase 2
0.7241	Intermediate Similarity	NPD5760	Phase 2
0.7222	Intermediate Similarity	NPD7801	Approved
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD943	Approved
0.7219	Intermediate Similarity	NPD4287	Approved
0.7205	Intermediate Similarity	NPD6798	Discontinued
0.7204	Intermediate Similarity	NPD8150	Discontinued
0.7202	Intermediate Similarity	NPD3887	Approved
0.7198	Intermediate Similarity	NPD1729	Discontinued
0.7179	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD422	Phase 1
0.7151	Intermediate Similarity	NPD6808	Phase 2
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD9545	Approved
0.7135	Intermediate Similarity	NPD5049	Phase 3
0.7135	Intermediate Similarity	NPD6273	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7126	Intermediate Similarity	NPD2424	Discontinued
0.7118	Intermediate Similarity	NPD7390	Discontinued
0.7107	Intermediate Similarity	NPD1164	Approved
0.7107	Intermediate Similarity	NPD3267	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