NPASS Compound

Structure

NPC469675 OpenBabel07101719242D 24 27 0 0 1 0 0 0 0 0999 V2000 6.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5622 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8301 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 0.1340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 10 2 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 11 17 2 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 9 1 6 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 18 15 1 1 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	331.087
LogP:	4.008
LogD:	3.06
LogS:	-5.373
# Rotatable Bonds:	5
TPSA:	64.5
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.02
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.777
MDCK Permeability:	1.686096584307961e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.462

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	87.34282684326172%
Volume Distribution (VD):	1.49
Pgp-substrate:	9.30477523803711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.301
CYP1A2-substrate:	0.785
CYP2C19-inhibitor:	0.295
CYP2C19-substrate:	0.475
CYP2C9-inhibitor:	0.398
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.368
CYP2D6-substrate:	0.71
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.387

ADMET: Excretion

Clearance (CL):	6.307
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.694
Rat Oral Acute Toxicity:	0.143
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.133
Carcinogencity:	0.549
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.539

Download Data

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

Natural Product: NPC469675

Natural Product ID:	NPC469675
*Common Name:**	7-[[(2R)-3,3-Dimethyloxiran-2-Yl]Methoxy]-8-[(2R,3R)-3-Prop-1-En-2-Yloxiran-2-Yl]Chromen-2-One
IUPAC Name:	7-[[(2R)-3,3-dimethyloxiran-2-yl]methoxy]-8-[(2R,3R)-3-prop-1-en-2-yloxiran-2-yl]chromen-2-one
Synonyms:
Standard InCHIKey:	UGERORSNMILQIE-MZMPZRCHSA-N
Standard InCHI:	InChI=1S/C19H20O5/c1-10(2)16-18(23-16)15-12(21-9-13-19(3,4)24-13)7-5-11-6-8-14(20)22-17(11)15/h5-8,13,16,18H,1,9H2,2-4H3/t13-,16-,18-/m1/s1
SMILES:	CC(=C)C1C(O1)C2=C(C=CC3=C2OC(=O)C=C3)OCC4C(O4)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098139
PubChem CID:	46831976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO5744	Galipea panamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20423106]
NPO5744	Galipea panamensis	Species	Rutaceae	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	CC50	=	9.7	ug.mL-1	PMID[568437]
NPT3632	Organism	Leishmania panamensis	Leishmania panamensis	EC50	=	10.0	ug.mL-1	PMID[568437]
NPT2	Others	Unspecified		Selectivity Index	=	1.0	n.a.	PMID[568437]

☑ 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 NPC469675 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	455
0.1-0.2	1810
0.2-0.3	4779
0.3-0.4	10425
0.4-0.5	8039
0.5-0.6	4568
0.6-0.7	6001
0.7-0.8	5625
0.8-0.85	729
0.85-0.9	209
0.9-0.95	56
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9609	High Similarity	NPC80170
0.9538	High Similarity	NPC133956
0.9538	High Similarity	NPC471910
0.9538	High Similarity	NPC296624
0.9538	High Similarity	NPC207002
0.9538	High Similarity	NPC318400
0.9538	High Similarity	NPC167111
0.9466	High Similarity	NPC287182
0.9466	High Similarity	NPC267412
0.9466	High Similarity	NPC195343
0.9466	High Similarity	NPC74655
0.9466	High Similarity	NPC198381
0.9466	High Similarity	NPC319859
0.9466	High Similarity	NPC47163
0.9466	High Similarity	NPC166672
0.9466	High Similarity	NPC18804
0.9466	High Similarity	NPC260265
0.9466	High Similarity	NPC164269
0.9466	High Similarity	NPC127888
0.9466	High Similarity	NPC55149
0.9466	High Similarity	NPC100986
0.9466	High Similarity	NPC307412
0.9466	High Similarity	NPC84894
0.9462	High Similarity	NPC14248
0.9453	High Similarity	NPC199204
0.9394	High Similarity	NPC471909
0.9394	High Similarity	NPC471625
0.9394	High Similarity	NPC472424
0.9394	High Similarity	NPC281241
0.9394	High Similarity	NPC86892
0.9389	High Similarity	NPC222036
0.9389	High Similarity	NPC7526
0.9323	High Similarity	NPC128529
0.9323	High Similarity	NPC283019
0.9323	High Similarity	NPC471630
0.9323	High Similarity	NPC55615
0.9323	High Similarity	NPC476455
0.9323	High Similarity	NPC160727
0.9323	High Similarity	NPC149320
0.9323	High Similarity	NPC177281
0.9254	High Similarity	NPC155963
0.9248	High Similarity	NPC472525
0.9231	High Similarity	NPC168710
0.9197	High Similarity	NPC183646
0.9197	High Similarity	NPC119640
0.9185	High Similarity	NPC211110
0.9185	High Similarity	NPC279573
0.9185	High Similarity	NPC151946
0.9179	High Similarity	NPC38099
0.9179	High Similarity	NPC26954
0.9179	High Similarity	NPC283331
0.9173	High Similarity	NPC180716
0.9173	High Similarity	NPC62366
0.9173	High Similarity	NPC213173
0.9173	High Similarity	NPC224475
0.9141	High Similarity	NPC201667
0.9141	High Similarity	NPC73413
0.913	High Similarity	NPC476457
0.9118	High Similarity	NPC312881
0.9111	High Similarity	NPC153818
0.9111	High Similarity	NPC232246
0.9104	High Similarity	NPC33986
0.9098	High Similarity	NPC31849
0.907	High Similarity	NPC471828
0.907	High Similarity	NPC471827
0.9062	High Similarity	NPC472518
0.9062	High Similarity	NPC109675
0.9062	High Similarity	NPC273772
0.9051	High Similarity	NPC287286
0.9051	High Similarity	NPC195357
0.9051	High Similarity	NPC152771
0.9037	High Similarity	NPC188380
0.9037	High Similarity	NPC224543
0.9037	High Similarity	NPC78746
0.903	High Similarity	NPC98179
0.903	High Similarity	NPC204353
0.903	High Similarity	NPC253574
0.903	High Similarity	NPC50896
0.903	High Similarity	NPC326600
0.9008	High Similarity	NPC472519
0.9008	High Similarity	NPC185066
0.9	High Similarity	NPC471826
0.9	High Similarity	NPC234109
0.9	High Similarity	NPC188327
0.8992	High Similarity	NPC27671
0.8984	High Similarity	NPC96286
0.8984	High Similarity	NPC248429
0.8971	High Similarity	NPC225106
0.8971	High Similarity	NPC294456
0.8971	High Similarity	NPC281014
0.8971	High Similarity	NPC212124
0.8971	High Similarity	NPC184861
0.8947	High Similarity	NPC29734
0.8881	High Similarity	NPC194277
0.8872	High Similarity	NPC113098
0.8857	High Similarity	NPC471824
0.8846	High Similarity	NPC111347
0.8846	High Similarity	NPC291899
0.8828	High Similarity	NPC235190
0.8828	High Similarity	NPC180006
0.8828	High Similarity	NPC163200
0.8815	High Similarity	NPC163557
0.8815	High Similarity	NPC469449
0.8806	High Similarity	NPC267336
0.8806	High Similarity	NPC272650
0.8794	High Similarity	NPC85624
0.8794	High Similarity	NPC469701
0.8794	High Similarity	NPC76657
0.8769	High Similarity	NPC50720
0.8769	High Similarity	NPC290605
0.8769	High Similarity	NPC154176
0.8769	High Similarity	NPC173350
0.8768	High Similarity	NPC270256
0.876	High Similarity	NPC144418
0.8741	High Similarity	NPC19157
0.8741	High Similarity	NPC469956
0.8732	High Similarity	NPC205361
0.8731	High Similarity	NPC19242
0.8722	High Similarity	NPC293642
0.8722	High Similarity	NPC139595
0.8722	High Similarity	NPC60704
0.8696	High Similarity	NPC471069
0.8696	High Similarity	NPC14697
0.8696	High Similarity	NPC471068
0.8692	High Similarity	NPC150214
0.8692	High Similarity	NPC257188
0.8692	High Similarity	NPC13007
0.8676	High Similarity	NPC469955
0.8676	High Similarity	NPC472522
0.8676	High Similarity	NPC241341
0.8676	High Similarity	NPC233018
0.8676	High Similarity	NPC469952
0.8676	High Similarity	NPC36437
0.8672	High Similarity	NPC298796
0.8672	High Similarity	NPC281356
0.8671	High Similarity	NPC471764
0.8671	High Similarity	NPC296377
0.8671	High Similarity	NPC87950
0.8647	High Similarity	NPC121740
0.8647	High Similarity	NPC258567
0.8647	High Similarity	NPC243688
0.8647	High Similarity	NPC224774
0.8647	High Similarity	NPC289316
0.8633	High Similarity	NPC471071
0.8633	High Similarity	NPC471072
0.8633	High Similarity	NPC471070
0.8626	High Similarity	NPC315807
0.8623	High Similarity	NPC167517
0.8611	High Similarity	NPC169510
0.8603	High Similarity	NPC123954
0.8603	High Similarity	NPC319969
0.8603	High Similarity	NPC137669
0.8594	High Similarity	NPC152306
0.8594	High Similarity	NPC265547
0.8594	High Similarity	NPC96705
0.8592	High Similarity	NPC471763
0.8582	High Similarity	NPC157212
0.8582	High Similarity	NPC469453
0.8571	High Similarity	NPC163248
0.8571	High Similarity	NPC101894
0.8561	High Similarity	NPC306365
0.854	High Similarity	NPC54503
0.854	High Similarity	NPC55147
0.8521	High Similarity	NPC138212
0.8511	High Similarity	NPC300611
0.8511	High Similarity	NPC279851
0.8511	High Similarity	NPC472520
0.8496	Intermediate Similarity	NPC232692
0.8496	Intermediate Similarity	NPC244495
0.8496	Intermediate Similarity	NPC202594
0.8496	Intermediate Similarity	NPC93219
0.8489	Intermediate Similarity	NPC286843
0.8485	Intermediate Similarity	NPC143725
0.8478	Intermediate Similarity	NPC309953
0.8478	Intermediate Similarity	NPC131950
0.8478	Intermediate Similarity	NPC147030
0.8472	Intermediate Similarity	NPC171656
0.8467	Intermediate Similarity	NPC175159
0.8456	Intermediate Similarity	NPC240722
0.8456	Intermediate Similarity	NPC244799
0.8456	Intermediate Similarity	NPC476399
0.8456	Intermediate Similarity	NPC32463
0.8438	Intermediate Similarity	NPC128633
0.8433	Intermediate Similarity	NPC329272
0.8429	Intermediate Similarity	NPC131198
0.8417	Intermediate Similarity	NPC224941
0.8417	Intermediate Similarity	NPC311430
0.8417	Intermediate Similarity	NPC229128
0.8417	Intermediate Similarity	NPC472521
0.8417	Intermediate Similarity	NPC234865
0.8406	Intermediate Similarity	NPC241165
0.8406	Intermediate Similarity	NPC1220
0.8406	Intermediate Similarity	NPC142563
0.8406	Intermediate Similarity	NPC141822
0.8406	Intermediate Similarity	NPC291551
0.8406	Intermediate Similarity	NPC2363
0.8406	Intermediate Similarity	NPC469965
0.8406	Intermediate Similarity	NPC205797
0.8394	Intermediate Similarity	NPC472517
0.8382	Intermediate Similarity	NPC27239

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 NPC469675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	990
0.2-0.3	1988
0.3-0.4	2701
0.4-0.5	1775
0.5-0.6	891
0.6-0.7	285
0.7-0.8	107
0.8-0.85	18
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8406	Intermediate Similarity	NPD5124	Phase 1
0.8406	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD422	Phase 1
0.8163	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1652	Phase 2
0.7914	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1296	Phase 2
0.7793	Intermediate Similarity	NPD2796	Approved
0.7792	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD920	Approved
0.7734	Intermediate Similarity	NPD1358	Approved
0.7727	Intermediate Similarity	NPD6801	Discontinued
0.7724	Intermediate Similarity	NPD3748	Approved
0.7704	Intermediate Similarity	NPD5691	Approved
0.7697	Intermediate Similarity	NPD1653	Approved
0.7676	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6799	Approved
0.7643	Intermediate Similarity	NPD7075	Discontinued
0.7635	Intermediate Similarity	NPD1243	Approved
0.7616	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD9697	Approved
0.7576	Intermediate Similarity	NPD5535	Approved
0.7568	Intermediate Similarity	NPD2424	Discontinued
0.7535	Intermediate Similarity	NPD4908	Phase 1
0.7519	Intermediate Similarity	NPD3134	Approved
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1548	Phase 1
0.7484	Intermediate Similarity	NPD919	Approved
0.7484	Intermediate Similarity	NPD6599	Discontinued
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7467	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3750	Approved
0.7464	Intermediate Similarity	NPD3496	Discontinued
0.7452	Intermediate Similarity	NPD7819	Suspended
0.7448	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1613	Approved
0.7448	Intermediate Similarity	NPD4060	Phase 1
0.7439	Intermediate Similarity	NPD5844	Phase 1
0.7436	Intermediate Similarity	NPD7411	Suspended
0.7436	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6832	Phase 2
0.741	Intermediate Similarity	NPD1610	Phase 2
0.7405	Intermediate Similarity	NPD3817	Phase 2
0.7403	Intermediate Similarity	NPD5403	Approved
0.74	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4626	Approved
0.7386	Intermediate Similarity	NPD5401	Approved
0.7376	Intermediate Similarity	NPD8651	Approved
0.7361	Intermediate Similarity	NPD3027	Phase 3
0.7358	Intermediate Similarity	NPD7768	Phase 2
0.7358	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4628	Phase 3
0.7342	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5494	Approved
0.7329	Intermediate Similarity	NPD4307	Phase 2
0.7324	Intermediate Similarity	NPD3267	Approved
0.7324	Intermediate Similarity	NPD2797	Approved
0.7324	Intermediate Similarity	NPD3266	Approved
0.7312	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6798	Discontinued
0.7308	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7097	Phase 1
0.7296	Intermediate Similarity	NPD5402	Approved
0.7292	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1611	Approved
0.7286	Intermediate Similarity	NPD1091	Approved
0.7279	Intermediate Similarity	NPD4340	Discontinued
0.7279	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD2684	Approved
0.7273	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3225	Approved
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7241	Intermediate Similarity	NPD4625	Phase 3
0.7226	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1549	Phase 2
0.72	Intermediate Similarity	NPD1551	Phase 2
0.72	Intermediate Similarity	NPD2935	Discontinued
0.7192	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3268	Approved
0.7185	Intermediate Similarity	NPD7843	Approved
0.7183	Intermediate Similarity	NPD4749	Approved
0.717	Intermediate Similarity	NPD1934	Approved
0.7162	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7549	Discontinued
0.7153	Intermediate Similarity	NPD7157	Approved
0.7153	Intermediate Similarity	NPD1019	Discontinued
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD5763	Approved
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7152	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD4308	Phase 3
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7133	Intermediate Similarity	NPD1510	Phase 2
0.7132	Intermediate Similarity	NPD1241	Discontinued
0.7126	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3018	Phase 2
0.7101	Intermediate Similarity	NPD6559	Discontinued
0.7081	Intermediate Similarity	NPD2415	Discontinued
0.7081	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2313	Discontinued
0.7073	Intermediate Similarity	NPD1247	Approved
0.7071	Intermediate Similarity	NPD5585	Approved
0.707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD290	Approved
0.7067	Intermediate Similarity	NPD4538	Approved
0.7067	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4536	Approved
0.7059	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2532	Approved
0.7051	Intermediate Similarity	NPD2534	Approved
0.7051	Intermediate Similarity	NPD2533	Approved
0.7048	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5058	Phase 3
0.7032	Intermediate Similarity	NPD6666	Approved
0.7032	Intermediate Similarity	NPD6667	Approved
0.7021	Intermediate Similarity	NPD1778	Approved
0.702	Intermediate Similarity	NPD5960	Phase 3
0.7019	Intermediate Similarity	NPD2801	Approved
0.7019	Intermediate Similarity	NPD8455	Phase 2
0.7007	Intermediate Similarity	NPD7095	Approved
0.6993	Remote Similarity	NPD2981	Phase 2
0.6993	Remote Similarity	NPD9717	Approved
0.6987	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2861	Phase 2
0.698	Remote Similarity	NPD1240	Approved
0.698	Remote Similarity	NPD4140	Approved
0.6974	Remote Similarity	NPD6032	Approved
0.6974	Remote Similarity	NPD2438	Suspended
0.6968	Remote Similarity	NPD3887	Approved
0.6964	Remote Similarity	NPD3751	Discontinued
0.6964	Remote Similarity	NPD3818	Discontinued
0.6957	Remote Similarity	NPD37	Approved
0.6944	Remote Similarity	NPD2983	Phase 2
0.6944	Remote Similarity	NPD2982	Phase 2
0.6933	Remote Similarity	NPD1933	Approved
0.6933	Remote Similarity	NPD4967	Phase 2
0.6933	Remote Similarity	NPD3882	Suspended
0.6933	Remote Similarity	NPD447	Suspended
0.6933	Remote Similarity	NPD4966	Approved
0.6933	Remote Similarity	NPD4965	Approved
0.6929	Remote Similarity	NPD5536	Phase 2
0.6929	Remote Similarity	NPD7644	Approved
0.6928	Remote Similarity	NPD6232	Discontinued
0.6928	Remote Similarity	NPD3787	Discontinued
0.6928	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD3705	Approved
0.6918	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4062	Phase 3
0.6908	Remote Similarity	NPD5588	Approved
0.6906	Remote Similarity	NPD6671	Approved
0.6903	Remote Similarity	NPD7466	Approved
0.6901	Remote Similarity	NPD17	Approved
0.689	Remote Similarity	NPD3749	Approved
0.6887	Remote Similarity	NPD1607	Approved
0.6884	Remote Similarity	NPD5283	Phase 1
0.6879	Remote Similarity	NPD7212	Phase 2
0.6879	Remote Similarity	NPD1511	Approved
0.6879	Remote Similarity	NPD7213	Phase 3
0.6871	Remote Similarity	NPD5353	Approved
0.6871	Remote Similarity	NPD2237	Approved
0.6871	Remote Similarity	NPD4288	Approved
0.6867	Remote Similarity	NPD8127	Discontinued
0.6867	Remote Similarity	NPD2979	Phase 3
0.6867	Remote Similarity	NPD7199	Phase 2
0.6863	Remote Similarity	NPD4476	Approved
0.6863	Remote Similarity	NPD4477	Approved
0.6852	Remote Similarity	NPD4433	Discontinued
0.6849	Remote Similarity	NPD1203	Approved
0.6849	Remote Similarity	NPD987	Approved
0.6848	Remote Similarity	NPD6234	Discontinued
0.6846	Remote Similarity	NPD1048	Approved
0.6846	Remote Similarity	NPD7985	Registered
0.6846	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6166	Phase 2
0.6842	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5953	Discontinued
0.6839	Remote Similarity	NPD2800	Approved
0.6835	Remote Similarity	NPD7447	Phase 1
0.6828	Remote Similarity	NPD4359	Approved
0.6824	Remote Similarity	NPD7286	Phase 2
0.6824	Remote Similarity	NPD7054	Approved
0.6821	Remote Similarity	NPD230	Phase 1
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7266	Discontinued
0.6815	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1465	Phase 2

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