NPASS Compound

Structure

CID85381 OpenBabel06191715422D 41 48 0 0 1 0 0 0 0 0999 V2000 2.2870 -3.2254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2870 2.7746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6389 -3.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3566 -2.3597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1652 -2.3161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0972 -3.5265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4266 -2.7293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1322 -3.2048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4654 0.1957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1530 -0.7254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7422 -0.2778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1530 -1.7254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2002 -1.5256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3387 -2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9737 -2.6853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4047 0.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2870 0.7746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1745 -0.1300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0682 -2.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1837 -2.1244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9226 0.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2870 -0.2254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4981 -3.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6667 -0.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0214 -0.9539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4210 -1.7254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3461 -3.6206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5929 -3.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6309 0.7177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5981 0.0330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4210 1.2746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4210 -0.7254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5550 0.7746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5550 -0.2254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5446 -0.7894 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2870 -2.2254 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3090 -4.6199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4210 2.2746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0826 -3.4614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0544 1.0885 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 36 1 0 0 0 0 2 38 1 0 0 0 0 3 6 1 0 0 0 0 3 19 2 0 0 0 0 4 7 2 0 0 0 0 4 19 1 0 0 0 0 5 8 2 0 0 0 0 5 20 1 0 0 0 0 6 23 2 0 0 0 0 7 23 1 0 0 0 0 8 27 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 35 1 0 0 0 0 12 36 1 0 0 0 0 13 20 1 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 28 1 0 0 0 0 16 21 2 0 0 0 0 16 29 1 0 0 0 0 17 22 2 0 0 0 0 17 31 1 0 0 0 0 18 24 2 0 0 0 0 18 30 1 0 0 0 0 21 24 1 0 0 0 0 22 32 1 0 0 0 0 23 39 1 0 0 0 0 24 25 1 0 0 0 0 25 35 2 0 0 0 0 26 14 1 1 0 0 0 26 32 1 0 0 0 0 26 36 1 0 0 0 0 27 28 2 0 0 0 0 27 37 1 0 0 0 0 28 39 1 0 0 0 0 29 30 2 0 0 0 0 29 40 1 0 0 0 0 30 41 1 0 0 0 0 31 33 2 0 0 0 0 31 38 1 0 0 0 0 32 34 2 0 0 0 0 33 34 1 0 0 0 0 33 40 1 0 0 0 0 34 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.22
Volume:	559.839
LogP:	6.804
LogD:	3.701
LogS:	-8.64
# Rotatable Bonds:	1
TPSA:	72.75
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.25
Synthetic Accessibility Score:	5.765
Fsp3:	0.265
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.819
MDCK Permeability:	1.8820968762156554e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.34
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	92.3938217163086%
Volume Distribution (VD):	0.64
Pgp-substrate:	3.7707247734069824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.148
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.554
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.938

ADMET: Excretion

Clearance (CL):	8.331
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.911
Human Hepatotoxicity (H-HT):	0.015
Drug-inuced Liver Injury (DILI):	0.648
AMES Toxicity:	0.231
Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.921
Carcinogencity:	0.084
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.586

Download Data

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

Natural Product: NPC85381

Natural Product ID:	NPC85381
*Common Name:**	Dehydroapateline
IUPAC Name:	n.a.
Synonyms:	Dehydroapateline
Standard InCHIKey:	HUUXXMNWOPUALW-SANMLTNESA-N
Standard InCHI:	InChI=1S/C34H30N2O5/c1-36-12-10-22-17-31(38-2)33-34-32(22)26(36)14-19-3-6-23(7-4-19)39-28-15-20(5-8-27(28)37)13-25-24-18-30(41-34)29(40-33)16-21(24)9-11-35-25/h3-8,15-18,26,37H,9-14H2,1-2H3/t26-/m0/s1
SMILES:	COc1cc2CCN([C@@H]3c2c2c1Oc1cc4CCN=C(c4cc1O2)Cc1ccc(c(Oc2ccc(C3)cc2)c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390616
PubChem CID:	44559250
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO23690	Cocculus orbiculatus	Species	Menispermaceae	Eukaryota	n.a.	Formosan	n.a.	PMID[16038548]
NPO19551	Cocculus pendulus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19551	Cocculus pendulus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19551	Cocculus pendulus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23690	Cocculus orbiculatus	Species	Menispermaceae	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	4
Others	4

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2477	Cell Line	NUGC-3	Homo sapiens	Inhibition	=	0.0	%	PMID[470450]
NPT2477	Cell Line	NUGC-3	Homo sapiens	Inhibition	=	98.0	%	PMID[470450]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	4.71	ug.mL-1	PMID[470450]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16.3	ug.mL-1	PMID[470450]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	3.61	ug.mL-1	PMID[470450]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.0	%	PMID[470450]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	98.0	%	PMID[470450]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.82	ug.mL-1	PMID[470450]

☑ 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 NPC85381 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	387
0.1-0.2	1955
0.2-0.3	9968
0.3-0.4	7928
0.4-0.5	6424
0.5-0.6	10294
0.6-0.7	4785
0.7-0.8	750
0.8-0.85	95
0.85-0.9	41
0.9-0.95	36
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9769	High Similarity	NPC41122
0.9769	High Similarity	NPC318805
0.9659	High Similarity	NPC234318
0.9538	High Similarity	NPC249996
0.9422	High Similarity	NPC476202
0.9364	High Similarity	NPC195538
0.931	High Similarity	NPC42663
0.931	High Similarity	NPC290582
0.931	High Similarity	NPC222661
0.931	High Similarity	NPC285931
0.931	High Similarity	NPC258657
0.931	High Similarity	NPC229373
0.931	High Similarity	NPC311973
0.931	High Similarity	NPC49075
0.931	High Similarity	NPC328155
0.931	High Similarity	NPC15414
0.931	High Similarity	NPC290005
0.931	High Similarity	NPC54654
0.931	High Similarity	NPC185639
0.931	High Similarity	NPC7715
0.931	High Similarity	NPC90998
0.931	High Similarity	NPC251735
0.931	High Similarity	NPC104196
0.931	High Similarity	NPC8836
0.931	High Similarity	NPC181796
0.931	High Similarity	NPC182052
0.931	High Similarity	NPC223690
0.931	High Similarity	NPC279228
0.931	High Similarity	NPC271013
0.931	High Similarity	NPC217748
0.931	High Similarity	NPC239824
0.9257	High Similarity	NPC274716
0.9257	High Similarity	NPC254441
0.9257	High Similarity	NPC167116
0.9253	High Similarity	NPC286119
0.92	High Similarity	NPC30779
0.9153	High Similarity	NPC116465
0.9153	High Similarity	NPC212237
0.9101	High Similarity	NPC275680
0.9101	High Similarity	NPC22115
0.905	High Similarity	NPC82457
0.905	High Similarity	NPC48490
0.905	High Similarity	NPC206900
0.905	High Similarity	NPC11296
0.905	High Similarity	NPC175890
0.905	High Similarity	NPC274661
0.9	High Similarity	NPC191132
0.9	High Similarity	NPC60295
0.8989	High Similarity	NPC95426
0.8989	High Similarity	NPC16357
0.8989	High Similarity	NPC302245
0.895	High Similarity	NPC24260
0.8939	High Similarity	NPC139783
0.8939	High Similarity	NPC65312
0.8908	High Similarity	NPC317145
0.8908	High Similarity	NPC115284
0.8908	High Similarity	NPC317439
0.8908	High Similarity	NPC76682
0.8908	High Similarity	NPC10908
0.8908	High Similarity	NPC63646
0.8908	High Similarity	NPC276890
0.8908	High Similarity	NPC198498
0.8908	High Similarity	NPC227060
0.8857	High Similarity	NPC12424
0.8857	High Similarity	NPC129518
0.8857	High Similarity	NPC251580
0.8857	High Similarity	NPC41376
0.8846	High Similarity	NPC478093
0.8798	High Similarity	NPC478091
0.8798	High Similarity	NPC30182
0.8798	High Similarity	NPC478092
0.8798	High Similarity	NPC473589
0.8793	High Similarity	NPC83198
0.8793	High Similarity	NPC204908
0.8786	High Similarity	NPC264850
0.8786	High Similarity	NPC13916
0.8757	High Similarity	NPC293093
0.8728	High Similarity	NPC24465
0.8696	High Similarity	NPC256124
0.8686	High Similarity	NPC66573
0.8678	High Similarity	NPC317272
0.8678	High Similarity	NPC250846
0.8678	High Similarity	NPC42549
0.8678	High Similarity	NPC256012
0.8678	High Similarity	NPC268503
0.8678	High Similarity	NPC240841
0.8663	High Similarity	NPC475654
0.8659	High Similarity	NPC243454
0.8659	High Similarity	NPC475479
0.8644	High Similarity	NPC152680
0.8644	High Similarity	NPC190783
0.8644	High Similarity	NPC232386
0.8611	High Similarity	NPC239584
0.8564	High Similarity	NPC73492
0.8564	High Similarity	NPC299990
0.8441	Intermediate Similarity	NPC476565
0.8415	Intermediate Similarity	NPC302275
0.8387	Intermediate Similarity	NPC259350
0.8387	Intermediate Similarity	NPC223236
0.838	Intermediate Similarity	NPC239775
0.838	Intermediate Similarity	NPC108434
0.838	Intermediate Similarity	NPC475215
0.8333	Intermediate Similarity	NPC254581
0.8333	Intermediate Similarity	NPC281581
0.8324	Intermediate Similarity	NPC276588
0.8324	Intermediate Similarity	NPC193949
0.8324	Intermediate Similarity	NPC207757
0.8324	Intermediate Similarity	NPC5238
0.8324	Intermediate Similarity	NPC469817
0.8324	Intermediate Similarity	NPC39701
0.8324	Intermediate Similarity	NPC172765
0.8324	Intermediate Similarity	NPC110416
0.8324	Intermediate Similarity	NPC189266
0.8324	Intermediate Similarity	NPC184026
0.8324	Intermediate Similarity	NPC54379
0.8324	Intermediate Similarity	NPC2413
0.8324	Intermediate Similarity	NPC204828
0.8324	Intermediate Similarity	NPC168753
0.8324	Intermediate Similarity	NPC278799
0.8324	Intermediate Similarity	NPC127674
0.8324	Intermediate Similarity	NPC118274
0.8324	Intermediate Similarity	NPC249797
0.8324	Intermediate Similarity	NPC295691
0.8298	Intermediate Similarity	NPC471113
0.8289	Intermediate Similarity	NPC473716
0.8289	Intermediate Similarity	NPC475597
0.8286	Intermediate Similarity	NPC329837
0.8286	Intermediate Similarity	NPC216816
0.8278	Intermediate Similarity	NPC231371
0.8276	Intermediate Similarity	NPC25084
0.8276	Intermediate Similarity	NPC247639
0.8252	Intermediate Similarity	NPC201508
0.8226	Intermediate Similarity	NPC14507
0.8226	Intermediate Similarity	NPC47077
0.8218	Intermediate Similarity	NPC107602
0.8192	Intermediate Similarity	NPC60186
0.8173	Intermediate Similarity	NPC96584
0.8173	Intermediate Similarity	NPC255800
0.8152	Intermediate Similarity	NPC474507
0.814	Intermediate Similarity	NPC103379
0.814	Intermediate Similarity	NPC477565
0.8136	Intermediate Similarity	NPC230956
0.8136	Intermediate Similarity	NPC271388
0.8136	Intermediate Similarity	NPC119649
0.8136	Intermediate Similarity	NPC205255
0.8136	Intermediate Similarity	NPC235143
0.8111	Intermediate Similarity	NPC158376
0.8111	Intermediate Similarity	NPC12053
0.8111	Intermediate Similarity	NPC205421
0.8111	Intermediate Similarity	NPC306555
0.8111	Intermediate Similarity	NPC145832
0.8111	Intermediate Similarity	NPC474931
0.8111	Intermediate Similarity	NPC117188
0.8111	Intermediate Similarity	NPC81218
0.8101	Intermediate Similarity	NPC253043
0.8101	Intermediate Similarity	NPC78222
0.8101	Intermediate Similarity	NPC196447
0.8101	Intermediate Similarity	NPC212794
0.8101	Intermediate Similarity	NPC96603
0.8101	Intermediate Similarity	NPC13504
0.8101	Intermediate Similarity	NPC306843
0.8101	Intermediate Similarity	NPC136508
0.8101	Intermediate Similarity	NPC477563
0.8092	Intermediate Similarity	NPC220858
0.8092	Intermediate Similarity	NPC151895
0.8092	Intermediate Similarity	NPC97221
0.8092	Intermediate Similarity	NPC192768
0.8092	Intermediate Similarity	NPC88249
0.809	Intermediate Similarity	NPC79402
0.809	Intermediate Similarity	NPC50380
0.809	Intermediate Similarity	NPC179250
0.809	Intermediate Similarity	NPC80759
0.8081	Intermediate Similarity	NPC135538
0.8081	Intermediate Similarity	NPC246587
0.8081	Intermediate Similarity	NPC428
0.8081	Intermediate Similarity	NPC24233
0.8081	Intermediate Similarity	NPC476571
0.8081	Intermediate Similarity	NPC147390
0.8079	Intermediate Similarity	NPC221864
0.8077	Intermediate Similarity	NPC10871
0.8056	Intermediate Similarity	NPC68328
0.8046	Intermediate Similarity	NPC476568
0.8046	Intermediate Similarity	NPC127402
0.8045	Intermediate Similarity	NPC475393
0.8045	Intermediate Similarity	NPC324144
0.8043	Intermediate Similarity	NPC173416
0.8043	Intermediate Similarity	NPC476577
0.8043	Intermediate Similarity	NPC148709
0.8023	Intermediate Similarity	NPC179825
0.8023	Intermediate Similarity	NPC191376
0.8023	Intermediate Similarity	NPC476151
0.8023	Intermediate Similarity	NPC321505
0.8	Intermediate Similarity	NPC238530
0.8	Intermediate Similarity	NPC276944
0.8	Intermediate Similarity	NPC232514
0.798	Intermediate Similarity	NPC82056
0.7957	Intermediate Similarity	NPC32154
0.7944	Intermediate Similarity	NPC1229
0.7933	Intermediate Similarity	NPC27410
0.7933	Intermediate Similarity	NPC166014

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 NPC85381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	723
0.2-0.3	1110
0.3-0.4	1981
0.4-0.5	2631
0.5-0.6	1774
0.6-0.7	635
0.7-0.8	88
0.8-0.85	1
0.85-0.9	1
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.931	High Similarity	NPD8053	Approved
0.931	High Similarity	NPD8054	Approved
0.8908	High Similarity	NPD8251	Approved
0.8908	High Similarity	NPD8252	Approved
0.8908	High Similarity	NPD8099	Discontinued
0.8857	High Similarity	NPD8156	Discontinued
0.8031	Intermediate Similarity	NPD8095	Phase 1
0.7978	Intermediate Similarity	NPD6788	Approved
0.7944	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4005	Discontinued
0.7919	Intermediate Similarity	NPD4584	Approved
0.7861	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD4675	Approved
0.7797	Intermediate Similarity	NPD4678	Approved
0.7749	Intermediate Similarity	NPD7906	Approved
0.773	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4055	Discovery
0.7581	Intermediate Similarity	NPD27	Approved
0.7581	Intermediate Similarity	NPD2489	Approved
0.7569	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3051	Approved
0.7568	Intermediate Similarity	NPD6071	Discontinued
0.7556	Intermediate Similarity	NPD4773	Phase 2
0.7556	Intermediate Similarity	NPD4772	Phase 2
0.7541	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7833	Phase 2
0.7541	Intermediate Similarity	NPD7831	Phase 2
0.7539	Intermediate Similarity	NPD7311	Approved
0.7539	Intermediate Similarity	NPD7310	Approved
0.7539	Intermediate Similarity	NPD4577	Approved
0.7539	Intermediate Similarity	NPD7312	Approved
0.7539	Intermediate Similarity	NPD7313	Approved
0.7539	Intermediate Similarity	NPD4578	Approved
0.7527	Intermediate Similarity	NPD2969	Approved
0.7527	Intermediate Similarity	NPD2970	Approved
0.7514	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4123	Phase 3
0.7514	Intermediate Similarity	NPD7447	Phase 1
0.7513	Intermediate Similarity	NPD4663	Approved
0.75	Intermediate Similarity	NPD7309	Approved
0.7487	Intermediate Similarity	NPD7549	Discontinued
0.7486	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7213	Phase 3
0.7458	Intermediate Similarity	NPD7212	Phase 2
0.7444	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2560	Approved
0.7432	Intermediate Similarity	NPD2563	Approved
0.743	Intermediate Similarity	NPD2122	Discontinued
0.7418	Intermediate Similarity	NPD7298	Approved
0.7385	Intermediate Similarity	NPD7291	Discontinued
0.738	Intermediate Similarity	NPD4010	Discontinued
0.7377	Intermediate Similarity	NPD5773	Approved
0.7377	Intermediate Similarity	NPD5772	Approved
0.7351	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3692	Discontinued
0.7318	Intermediate Similarity	NPD1424	Approved
0.7306	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2898	Approved
0.7299	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2420	Approved
0.7263	Intermediate Similarity	NPD2421	Approved
0.7253	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6031	Approved
0.7238	Intermediate Similarity	NPD6030	Approved
0.7228	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2674	Phase 3
0.7181	Intermediate Similarity	NPD5677	Discontinued
0.7174	Intermediate Similarity	NPD6072	Discontinued
0.7158	Intermediate Similarity	NPD4017	Approved
0.7157	Intermediate Similarity	NPD3452	Approved
0.7157	Intermediate Similarity	NPD3450	Approved
0.7157	Intermediate Similarity	NPD2494	Approved
0.7157	Intermediate Similarity	NPD2493	Approved
0.7151	Intermediate Similarity	NPD5241	Discontinued
0.7143	Intermediate Similarity	NPD7827	Phase 1
0.7136	Intermediate Similarity	NPD2488	Approved
0.7136	Intermediate Similarity	NPD2490	Approved
0.7135	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7034	Discontinued
0.712	Intermediate Similarity	NPD4481	Phase 3
0.7112	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3845	Phase 1
0.7111	Intermediate Similarity	NPD7124	Phase 2
0.7097	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6331	Phase 2
0.7083	Intermediate Similarity	NPD6997	Phase 2
0.7081	Intermediate Similarity	NPD5089	Approved
0.7081	Intermediate Similarity	NPD5090	Approved
0.7074	Intermediate Similarity	NPD5604	Discontinued
0.7067	Intermediate Similarity	NPD7263	Phase 2
0.7059	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4583	Approved
0.7053	Intermediate Similarity	NPD7802	Discontinued
0.7053	Intermediate Similarity	NPD4582	Approved
0.7052	Intermediate Similarity	NPD3145	Approved
0.7052	Intermediate Similarity	NPD3144	Approved
0.7049	Intermediate Similarity	NPD3639	Approved
0.7049	Intermediate Similarity	NPD3641	Approved
0.7049	Intermediate Similarity	NPD3640	Phase 3
0.7011	Intermediate Similarity	NPD4474	Approved
0.7011	Intermediate Similarity	NPD4475	Approved
0.7005	Intermediate Similarity	NPD4002	Approved
0.7005	Intermediate Similarity	NPD4004	Approved
0.7	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6748	Discontinued
0.6995	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8070	Approved
0.697	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7047	Phase 3
0.6963	Remote Similarity	NPD6107	Approved
0.6961	Remote Similarity	NPD2973	Approved
0.6961	Remote Similarity	NPD2975	Approved
0.6961	Remote Similarity	NPD2974	Approved
0.6957	Remote Similarity	NPD5006	Approved
0.6957	Remote Similarity	NPD5005	Approved
0.6949	Remote Similarity	NPD2200	Suspended
0.6944	Remote Similarity	NPD5177	Phase 3
0.6936	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7773	Phase 2
0.6927	Remote Similarity	NPD3656	Approved
0.6923	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7477	Discontinued
0.6907	Remote Similarity	NPD3489	Phase 3
0.6902	Remote Similarity	NPD52	Approved
0.6902	Remote Similarity	NPD7526	Approved
0.6902	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7169	Suspended
0.6891	Remote Similarity	NPD4083	Discontinued
0.6889	Remote Similarity	NPD7153	Discontinued
0.6888	Remote Similarity	NPD3920	Phase 2
0.6882	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4604	Approved
0.6878	Remote Similarity	NPD4605	Approved
0.6875	Remote Similarity	NPD1613	Approved
0.6875	Remote Similarity	NPD6494	Phase 2
0.6875	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2219	Phase 1
0.6866	Remote Similarity	NPD6842	Approved
0.6866	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6841	Approved
0.6866	Remote Similarity	NPD6843	Phase 3
0.686	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4580	Approved
0.6857	Remote Similarity	NPD5718	Phase 2
0.6853	Remote Similarity	NPD8153	Approved
0.6853	Remote Similarity	NPD6297	Approved
0.6853	Remote Similarity	NPD8152	Approved
0.6847	Remote Similarity	NPD3924	Approved
0.6847	Remote Similarity	NPD3921	Approved
0.6847	Remote Similarity	NPD3922	Approved
0.6847	Remote Similarity	NPD3923	Approved
0.6845	Remote Similarity	NPD3296	Phase 1
0.6839	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4908	Phase 1
0.6834	Remote Similarity	NPD2971	Approved
0.6834	Remote Similarity	NPD2968	Approved
0.6834	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2843	Phase 2
0.6832	Remote Similarity	NPD2845	Phase 2
0.6813	Remote Similarity	NPD7466	Approved
0.6812	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6090	Discontinued
0.681	Remote Similarity	NPD4040	Phase 1
0.6809	Remote Similarity	NPD3778	Approved
0.6809	Remote Similarity	NPD7438	Suspended
0.6806	Remote Similarity	NPD8149	Discontinued
0.68	Remote Similarity	NPD6853	Approved
0.68	Remote Similarity	NPD6851	Approved
0.6798	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3124	Discontinued
0.6793	Remote Similarity	NPD7598	Phase 2
0.6789	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2161	Phase 2
0.6774	Remote Similarity	NPD3033	Phase 2
0.6772	Remote Similarity	NPD5722	Discontinued
0.6768	Remote Similarity	NPD7007	Discovery
0.6763	Remote Similarity	NPD4420	Approved
0.6761	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4162	Approved
0.6758	Remote Similarity	NPD3060	Approved
0.6758	Remote Similarity	NPD4237	Approved
0.6758	Remote Similarity	NPD4236	Phase 3
0.6757	Remote Similarity	NPD7019	Approved
0.6757	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7020	Approved
0.6755	Remote Similarity	NPD6502	Phase 2
0.6753	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD5313	Approved
0.6751	Remote Similarity	NPD42	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