NPASS Compound

Structure

CID239775 OpenBabel06191716042D 27 30 0 0 1 0 0 0 0 0999 V2000 0.8691 -4.3525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0262 -2.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2318 -0.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2698 -0.7580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9688 0.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6875 -1.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 -2.8957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8261 -3.4005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4945 -3.4241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5303 -1.4728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6585 -2.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8443 -1.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6764 -1.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0118 -2.9110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3484 -2.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3663 -1.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0114 -1.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8385 -1.4556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -0.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8329 -0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8588 -3.3823 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6742 0.0142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1784 -3.4515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2140 -1.5072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6681 -0.0040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0054 0.9633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 22 1 0 0 0 0 8 11 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 8 1 6 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 18 20 2 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	371.17
Volume:	376.675
LogP:	2.316
LogD:	2.536
LogS:	-2.156
# Rotatable Bonds:	4
TPSA:	60.39
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.891
Synthetic Accessibility Score:	3.147
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.782
MDCK Permeability:	2.2898675524629653e-05
Pgp-inhibitor:	0.439
Pgp-substrate:	0.873
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	87.00955200195312%
Volume Distribution (VD):	1.474
Pgp-substrate:	11.509810447692871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.734
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	6.996
Half-life (T1/2):	0.596

ADMET: Toxicity

hERG Blockers:	0.204
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.366
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.174
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC239775

Natural Product ID:	NPC239775
*Common Name:**	Thalbaicalidine
IUPAC Name:	(6aR)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-3-ol
Synonyms:	Thalbaicalidine
Standard InCHIKey:	WHOVKGFICRPUBN-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C21H25NO5/c1-22-7-6-12-17-14(22)8-11-9-15(24-2)16(25-3)10-13(11)18(17)20(26-4)21(27-5)19(12)23/h9-10,14,23H,6-8H2,1-5H3/t14-/m1/s1
SMILES:	CN1CCc2c3[C@H]1Cc1cc(c(cc1-c3c(c(c2O)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518061
PubChem CID:	10384584
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[9599253]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868142]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11053	Annona purpurea	Species	Annonaceae	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
Others	6

Activity Type	# Activity
CELL-LINE	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	86.3	%	PMID[524105]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	4.2	%	PMID[524105]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	0.0	%	PMID[524105]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	73.6	%	PMID[524105]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	72.2	%	PMID[524105]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	82.2	%	PMID[524105]

☑ 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 NPC239775 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	333
0.1-0.2	1598
0.2-0.3	7655
0.3-0.4	10802
0.4-0.5	5185
0.5-0.6	9155
0.6-0.7	6273
0.7-0.8	1236
0.8-0.85	242
0.85-0.9	155
0.9-0.95	45
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.981	High Similarity	NPC168753
0.981	High Similarity	NPC118274
0.9682	High Similarity	NPC196447
0.9682	High Similarity	NPC477563
0.9682	High Similarity	NPC13504
0.9682	High Similarity	NPC306843
0.9682	High Similarity	NPC96603
0.9682	High Similarity	NPC253043
0.9682	High Similarity	NPC136508
0.9682	High Similarity	NPC78222
0.9682	High Similarity	NPC212794
0.9618	High Similarity	NPC324144
0.9571	High Similarity	NPC474507
0.956	High Similarity	NPC117188
0.956	High Similarity	NPC81218
0.956	High Similarity	NPC205421
0.956	High Similarity	NPC158376
0.956	High Similarity	NPC12053
0.956	High Similarity	NPC145832
0.956	High Similarity	NPC306555
0.956	High Similarity	NPC474931
0.9448	High Similarity	NPC173416
0.9448	High Similarity	NPC476577
0.9448	High Similarity	NPC148709
0.9371	High Similarity	NPC1229
0.9367	High Similarity	NPC166014
0.9367	High Similarity	NPC27410
0.9321	High Similarity	NPC69712
0.9321	High Similarity	NPC477562
0.9321	High Similarity	NPC26240
0.9313	High Similarity	NPC24465
0.929	High Similarity	NPC82763
0.9268	High Similarity	NPC128560
0.9268	High Similarity	NPC199465
0.9268	High Similarity	NPC229166
0.9255	High Similarity	NPC13916
0.9255	High Similarity	NPC264850
0.9236	High Similarity	NPC99659
0.9236	High Similarity	NPC325871
0.9231	High Similarity	NPC186546
0.9231	High Similarity	NPC476576
0.9207	High Similarity	NPC477020
0.9207	High Similarity	NPC66341
0.9207	High Similarity	NPC192135
0.9198	High Similarity	NPC204947
0.9181	High Similarity	NPC478093
0.9157	High Similarity	NPC320223
0.9157	High Similarity	NPC114364
0.9146	High Similarity	NPC19520
0.9146	High Similarity	NPC149090
0.9128	High Similarity	NPC30182
0.9128	High Similarity	NPC478092
0.9128	High Similarity	NPC478091
0.9128	High Similarity	NPC473589
0.9119	High Similarity	NPC476572
0.9068	High Similarity	NPC60186
0.9059	High Similarity	NPC57036
0.9024	High Similarity	NPC83198
0.9024	High Similarity	NPC204908
0.9018	High Similarity	NPC35627
0.9018	High Similarity	NPC476573
0.9018	High Similarity	NPC81247
0.9006	High Similarity	NPC271388
0.9006	High Similarity	NPC235143
0.9006	High Similarity	NPC119649
0.9006	High Similarity	NPC205255
0.9006	High Similarity	NPC230956
0.8994	High Similarity	NPC116284
0.8951	High Similarity	NPC80759
0.8951	High Similarity	NPC79402
0.8947	High Similarity	NPC214116
0.8944	High Similarity	NPC221864
0.8935	High Similarity	NPC476574
0.8935	High Similarity	NPC312918
0.8935	High Similarity	NPC477561
0.8935	High Similarity	NPC155442
0.8924	High Similarity	NPC326316
0.8924	High Similarity	NPC81733
0.8916	High Similarity	NPC231371
0.8895	High Similarity	NPC275680
0.8895	High Similarity	NPC22115
0.8862	High Similarity	NPC152680
0.8862	High Similarity	NPC232386
0.8862	High Similarity	NPC190783
0.8848	High Similarity	NPC298979
0.8841	High Similarity	NPC302527
0.8841	High Similarity	NPC167546
0.8841	High Similarity	NPC16805
0.883	High Similarity	NPC135772
0.8824	High Similarity	NPC286119
0.8788	High Similarity	NPC24264
0.8788	High Similarity	NPC476432
0.8779	High Similarity	NPC95426
0.8779	High Similarity	NPC302245
0.8779	High Similarity	NPC16357
0.8772	High Similarity	NPC182052
0.8772	High Similarity	NPC290005
0.8772	High Similarity	NPC311973
0.8772	High Similarity	NPC290582
0.8772	High Similarity	NPC30779
0.8772	High Similarity	NPC7715
0.8772	High Similarity	NPC328155
0.8772	High Similarity	NPC49075
0.8772	High Similarity	NPC217748
0.8772	High Similarity	NPC223690
0.8772	High Similarity	NPC90998
0.8772	High Similarity	NPC54654
0.8772	High Similarity	NPC104196
0.8772	High Similarity	NPC285931
0.8772	High Similarity	NPC271013
0.8772	High Similarity	NPC258657
0.8772	High Similarity	NPC251735
0.8772	High Similarity	NPC181796
0.8772	High Similarity	NPC239824
0.8772	High Similarity	NPC279228
0.8772	High Similarity	NPC8836
0.8772	High Similarity	NPC222661
0.8772	High Similarity	NPC185639
0.8772	High Similarity	NPC15414
0.8772	High Similarity	NPC42663
0.8772	High Similarity	NPC229373
0.8765	High Similarity	NPC470879
0.8765	High Similarity	NPC258695
0.8758	High Similarity	NPC249797
0.8758	High Similarity	NPC193949
0.8758	High Similarity	NPC184026
0.8758	High Similarity	NPC207757
0.8758	High Similarity	NPC278799
0.8758	High Similarity	NPC172765
0.8758	High Similarity	NPC127674
0.8758	High Similarity	NPC5238
0.8758	High Similarity	NPC110416
0.8758	High Similarity	NPC2413
0.8758	High Similarity	NPC39701
0.8758	High Similarity	NPC276588
0.8758	High Similarity	NPC204828
0.8758	High Similarity	NPC54379
0.8758	High Similarity	NPC189266
0.8758	High Similarity	NPC295691
0.8758	High Similarity	NPC469817
0.8742	High Similarity	NPC192768
0.8742	High Similarity	NPC88249
0.8742	High Similarity	NPC97221
0.8742	High Similarity	NPC220858
0.8742	High Similarity	NPC151895
0.8736	High Similarity	NPC206900
0.8735	High Similarity	NPC247389
0.8735	High Similarity	NPC210918
0.8734	High Similarity	NPC24233
0.8734	High Similarity	NPC147390
0.8734	High Similarity	NPC476571
0.8734	High Similarity	NPC135538
0.8734	High Similarity	NPC246587
0.8734	High Similarity	NPC428
0.8728	High Similarity	NPC139783
0.8728	High Similarity	NPC65312
0.8727	High Similarity	NPC225774
0.8721	High Similarity	NPC274716
0.8721	High Similarity	NPC254441
0.8721	High Similarity	NPC167116
0.8721	High Similarity	NPC302275
0.8713	High Similarity	NPC474506
0.8713	High Similarity	NPC32413
0.8706	High Similarity	NPC23219
0.8704	High Similarity	NPC186063
0.8679	High Similarity	NPC477565
0.8679	High Similarity	NPC103379
0.8675	High Similarity	NPC56887
0.8675	High Similarity	NPC68328
0.8675	High Similarity	NPC223077
0.8675	High Similarity	NPC193853
0.8675	High Similarity	NPC219341
0.8671	High Similarity	NPC179825
0.8671	High Similarity	NPC191376
0.8671	High Similarity	NPC321505
0.8663	High Similarity	NPC248642
0.8655	High Similarity	NPC126284
0.8647	High Similarity	NPC112575
0.8642	High Similarity	NPC123323
0.8636	High Similarity	NPC117717
0.8621	High Similarity	NPC47077
0.8621	High Similarity	NPC212237
0.8621	High Similarity	NPC320088
0.8621	High Similarity	NPC116465
0.8621	High Similarity	NPC14507
0.8614	High Similarity	NPC209377
0.8613	High Similarity	NPC156576
0.8589	High Similarity	NPC203784
0.8589	High Similarity	NPC170503
0.8589	High Similarity	NPC126519
0.8588	High Similarity	NPC477558
0.8588	High Similarity	NPC329969
0.8553	High Similarity	NPC476151
0.8547	High Similarity	NPC32154
0.8545	High Similarity	NPC477559
0.8545	High Similarity	NPC160298
0.8545	High Similarity	NPC306902
0.8545	High Similarity	NPC232924
0.8545	High Similarity	NPC266753
0.8544	High Similarity	NPC185838

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 NPC239775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	785
0.2-0.3	1144
0.3-0.4	2207
0.4-0.5	2491
0.5-0.6	1549
0.6-0.7	600
0.7-0.8	136
0.8-0.85	23
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8772	High Similarity	NPD8054	Approved
0.8772	High Similarity	NPD8053	Approved
0.8608	High Similarity	NPD2420	Approved
0.8608	High Similarity	NPD2421	Approved
0.8409	Intermediate Similarity	NPD7906	Approved
0.8363	Intermediate Similarity	NPD8251	Approved
0.8363	Intermediate Similarity	NPD8252	Approved
0.8363	Intermediate Similarity	NPD8099	Discontinued
0.8353	Intermediate Similarity	NPD2489	Approved
0.8353	Intermediate Similarity	NPD27	Approved
0.8343	Intermediate Similarity	NPD3051	Approved
0.8323	Intermediate Similarity	NPD4584	Approved
0.8314	Intermediate Similarity	NPD8156	Discontinued
0.8294	Intermediate Similarity	NPD2969	Approved
0.8294	Intermediate Similarity	NPD2970	Approved
0.8291	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD4578	Approved
0.8286	Intermediate Similarity	NPD4577	Approved
0.8263	Intermediate Similarity	NPD6788	Approved
0.8249	Intermediate Similarity	NPD4663	Approved
0.8182	Intermediate Similarity	NPD7313	Approved
0.8182	Intermediate Similarity	NPD7312	Approved
0.8182	Intermediate Similarity	NPD7310	Approved
0.8182	Intermediate Similarity	NPD7311	Approved
0.8136	Intermediate Similarity	NPD7309	Approved
0.8125	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD2898	Approved
0.8023	Intermediate Similarity	NPD4010	Discontinued
0.7929	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD5241	Discontinued
0.7907	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4055	Discovery
0.7866	Intermediate Similarity	NPD3845	Phase 1
0.7866	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4481	Phase 3
0.7819	Intermediate Similarity	NPD2493	Approved
0.7819	Intermediate Similarity	NPD3450	Approved
0.7819	Intermediate Similarity	NPD2494	Approved
0.7819	Intermediate Similarity	NPD3452	Approved
0.7814	Intermediate Similarity	NPD2488	Approved
0.7814	Intermediate Similarity	NPD2490	Approved
0.7798	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7833	Phase 2
0.7791	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7831	Phase 2
0.7778	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7298	Approved
0.7714	Intermediate Similarity	NPD6071	Discontinued
0.7706	Intermediate Similarity	NPD4773	Phase 2
0.7706	Intermediate Similarity	NPD4772	Phase 2
0.7697	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD4583	Approved
0.7696	Intermediate Similarity	NPD4582	Approved
0.7692	Intermediate Similarity	NPD4017	Approved
0.7692	Intermediate Similarity	NPD4005	Discontinued
0.7674	Intermediate Similarity	NPD2563	Approved
0.7674	Intermediate Similarity	NPD2560	Approved
0.7665	Intermediate Similarity	NPD1424	Approved
0.7665	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4004	Approved
0.7644	Intermediate Similarity	NPD4002	Approved
0.763	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2974	Approved
0.7606	Intermediate Similarity	NPD2975	Approved
0.7606	Intermediate Similarity	NPD2973	Approved
0.7574	Intermediate Similarity	NPD3640	Phase 3
0.7574	Intermediate Similarity	NPD3641	Approved
0.7574	Intermediate Similarity	NPD3639	Approved
0.7545	Intermediate Similarity	NPD7124	Phase 2
0.7541	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8095	Phase 1
0.7516	Intermediate Similarity	NPD3109	Approved
0.7516	Intermediate Similarity	NPD3110	Approved
0.7487	Intermediate Similarity	NPD7047	Phase 3
0.7487	Intermediate Similarity	NPD4580	Approved
0.7486	Intermediate Similarity	NPD2971	Approved
0.7486	Intermediate Similarity	NPD2968	Approved
0.7471	Intermediate Similarity	NPD6031	Approved
0.7471	Intermediate Similarity	NPD6030	Approved
0.747	Intermediate Similarity	NPD5177	Phase 3
0.746	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7447	Phase 1
0.7439	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6997	Phase 2
0.7424	Intermediate Similarity	NPD7827	Phase 1
0.7396	Intermediate Similarity	NPD7212	Phase 2
0.7396	Intermediate Similarity	NPD7213	Phase 3
0.7394	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4678	Approved
0.7341	Intermediate Similarity	NPD4675	Approved
0.7337	Intermediate Similarity	NPD7549	Discontinued
0.7329	Intermediate Similarity	NPD5155	Approved
0.7329	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5156	Approved
0.7322	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4585	Approved
0.731	Intermediate Similarity	NPD6090	Discontinued
0.7303	Intermediate Similarity	NPD5677	Discontinued
0.7299	Intermediate Similarity	NPD5090	Approved
0.7299	Intermediate Similarity	NPD5089	Approved
0.7293	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5718	Phase 2
0.7278	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2606	Approved
0.7267	Intermediate Similarity	NPD2605	Approved
0.7267	Intermediate Similarity	NPD3595	Approved
0.7267	Intermediate Similarity	NPD3594	Approved
0.7263	Intermediate Similarity	NPD7802	Discontinued
0.7262	Intermediate Similarity	NPD3060	Approved
0.7246	Intermediate Similarity	NPD4725	Approved
0.7246	Intermediate Similarity	NPD4721	Approved
0.7246	Intermediate Similarity	NPD4726	Approved
0.7245	Intermediate Similarity	NPD4040	Phase 1
0.7239	Intermediate Similarity	NPD2674	Phase 3
0.7231	Intermediate Similarity	NPD5005	Approved
0.7231	Intermediate Similarity	NPD5006	Approved
0.7229	Intermediate Similarity	NPD1753	Discontinued
0.7228	Intermediate Similarity	NPD6297	Approved
0.7222	Intermediate Similarity	NPD3027	Phase 3
0.7216	Intermediate Similarity	NPD2977	Approved
0.7216	Intermediate Similarity	NPD2978	Approved
0.7213	Intermediate Similarity	NPD42	Phase 2
0.7213	Intermediate Similarity	NPD6042	Phase 2
0.7205	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3635	Approved
0.7205	Intermediate Similarity	NPD3637	Approved
0.7205	Intermediate Similarity	NPD3636	Approved
0.72	Intermediate Similarity	NPD6072	Discontinued
0.7191	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6111	Discontinued
0.7167	Intermediate Similarity	NPD6107	Approved
0.7165	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3057	Approved
0.7143	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3448	Approved
0.7143	Intermediate Similarity	NPD2491	Approved
0.7136	Intermediate Similarity	NPD7907	Approved
0.7134	Intermediate Similarity	NPD4475	Approved
0.7134	Intermediate Similarity	NPD4474	Approved
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4625	Phase 3
0.7113	Intermediate Similarity	NPD4420	Approved
0.7112	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4666	Phase 3
0.7093	Intermediate Similarity	NPD3124	Discontinued
0.7091	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1613	Approved
0.7091	Intermediate Similarity	NPD2238	Phase 2
0.7074	Intermediate Similarity	NPD6853	Approved
0.7074	Intermediate Similarity	NPD6851	Approved
0.7073	Intermediate Similarity	NPD3144	Approved
0.7073	Intermediate Similarity	NPD3145	Approved
0.7073	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2200	Suspended
0.7066	Intermediate Similarity	NPD6895	Approved
0.7066	Intermediate Similarity	NPD6896	Approved
0.7059	Intermediate Similarity	NPD4236	Phase 3
0.7059	Intermediate Similarity	NPD4237	Approved
0.7056	Intermediate Similarity	NPD5709	Phase 3
0.7056	Intermediate Similarity	NPD3533	Approved
0.7056	Intermediate Similarity	NPD2972	Approved
0.7055	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4123	Phase 3
0.7042	Intermediate Similarity	NPD6723	Discontinued
0.7039	Intermediate Similarity	NPD4665	Approved
0.7039	Intermediate Similarity	NPD4111	Phase 1
0.7035	Intermediate Similarity	NPD6666	Approved
0.7035	Intermediate Similarity	NPD6667	Approved
0.7035	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4166	Phase 2
0.7018	Intermediate Similarity	NPD5754	Discontinued
0.7011	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4256	Phase 2
0.7	Intermediate Similarity	NPD4257	Approved
0.6995	Remote Similarity	NPD6687	Approved
0.6995	Remote Similarity	NPD6688	Approved
0.6994	Remote Similarity	NPD7598	Phase 2
0.6989	Remote Similarity	NPD7479	Phase 2
0.6989	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5160	Discontinued
0.6971	Remote Similarity	NPD5976	Discontinued
0.6971	Remote Similarity	NPD4727	Phase 1
0.6968	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4908	Phase 1
0.6947	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7048	Phase 3
0.694	Remote Similarity	NPD6747	Phase 1
0.6935	Remote Similarity	NPD5312	Approved
0.6935	Remote Similarity	NPD4873	Discontinued
0.6935	Remote Similarity	NPD5313	Approved
0.6927	Remote Similarity	NPD5772	Approved
0.6927	Remote Similarity	NPD5773	Approved
0.6919	Remote Similarity	NPD7466	Approved
0.6919	Remote Similarity	NPD6748	Discontinued
0.6914	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5604	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data