NPASS Compound

Structure

NPC24465 OpenBabel07101718292D 27 30 0 0 1 0 0 0 0 0999 V2000 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 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 -0.8660 -1.5000 0.0000 C 0 0 0 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 22 1 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 15 19 1 0 0 0 0 15 22 1 1 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 21 2 0 0 0 0 18 26 1 0 0 0 0 19 20 2 0 0 0 0 20 21 1 0 0 0 0 20 23 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:	2.299
LogD:	2.817
LogS:	-2.479
# 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:	3.002
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.994
MDCK Permeability:	2.486939229129348e-05
Pgp-inhibitor:	0.64
Pgp-substrate:	0.942
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.079
30% Bioavailability (F30%):	0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	71.71305084228516%
Volume Distribution (VD):	0.966
Pgp-substrate:	23.081823348999023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.665
CYP2D6-inhibitor:	0.365
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	13.059
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.529
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.54
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.525
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC24465

Natural Product ID:	NPC24465
*Common Name:**	(-)-Tetrahydrostephabine
IUPAC Name:	(13aS)-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-1-ol
Synonyms:	(-)-Tetrahydrostephabine
Standard InCHIKey:	ONWMFADVKAKDCA-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C21H25NO5/c1-24-16-9-13-7-15-19-12(8-18(26-3)21(27-4)20(19)23)5-6-22(15)11-14(13)10-17(16)25-2/h8-10,15,23H,5-7,11H2,1-4H3/t15-/m0/s1
SMILES:	COc1cc2C[C@H]3c4c(CCN3Cc2cc1OC)cc(c(c4O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516695
PubChem CID:	44584402
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids 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
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	PMID[8254346]
NPO22151	Stephania pierrei	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
ED50	2
Others	2

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	2230.0	ng/ml	PMID[464146]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	1940.0	ng/ml	PMID[464146]
NPT2	Others	Unspecified		Ratio ED50	>	9.0	n.a.	PMID[464146]
NPT2	Others	Unspecified		Ratio ED50	>	10.0	n.a.	PMID[464146]

☑ 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 NPC24465 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	317
0.1-0.2	1549
0.2-0.3	7928
0.3-0.4	10473
0.4-0.5	5263
0.5-0.6	8805
0.6-0.7	6485
0.7-0.8	1434
0.8-0.85	207
0.85-0.9	151
0.9-0.95	80
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC264850
0.9935	High Similarity	NPC13916
0.943	High Similarity	NPC83198
0.943	High Similarity	NPC204908
0.9412	High Similarity	NPC469817
0.9412	High Similarity	NPC276588
0.9412	High Similarity	NPC127674
0.9412	High Similarity	NPC2413
0.9412	High Similarity	NPC249797
0.9412	High Similarity	NPC5238
0.9412	High Similarity	NPC39701
0.9412	High Similarity	NPC189266
0.9412	High Similarity	NPC172765
0.9412	High Similarity	NPC278799
0.9412	High Similarity	NPC193949
0.9412	High Similarity	NPC184026
0.9412	High Similarity	NPC54379
0.9412	High Similarity	NPC204828
0.9412	High Similarity	NPC207757
0.9412	High Similarity	NPC110416
0.9412	High Similarity	NPC295691
0.9313	High Similarity	NPC239775
0.9276	High Similarity	NPC220858
0.9276	High Similarity	NPC88249
0.9276	High Similarity	NPC192768
0.9276	High Similarity	NPC97221
0.9276	High Similarity	NPC151895
0.9268	High Similarity	NPC223690
0.9268	High Similarity	NPC251735
0.9268	High Similarity	NPC217748
0.9268	High Similarity	NPC90998
0.9268	High Similarity	NPC290005
0.9268	High Similarity	NPC328155
0.9268	High Similarity	NPC271013
0.9268	High Similarity	NPC285931
0.9268	High Similarity	NPC185639
0.9268	High Similarity	NPC49075
0.9268	High Similarity	NPC258657
0.9268	High Similarity	NPC181796
0.9268	High Similarity	NPC239824
0.9268	High Similarity	NPC279228
0.9268	High Similarity	NPC290582
0.9268	High Similarity	NPC54654
0.9268	High Similarity	NPC182052
0.9268	High Similarity	NPC104196
0.9268	High Similarity	NPC15414
0.9268	High Similarity	NPC229373
0.9268	High Similarity	NPC7715
0.9268	High Similarity	NPC8836
0.9268	High Similarity	NPC222661
0.9268	High Similarity	NPC42663
0.9268	High Similarity	NPC311973
0.9255	High Similarity	NPC190783
0.9255	High Similarity	NPC232386
0.9255	High Similarity	NPC152680
0.9212	High Similarity	NPC254441
0.9212	High Similarity	NPC274716
0.9212	High Similarity	NPC167116
0.9207	High Similarity	NPC286119
0.9152	High Similarity	NPC30779
0.913	High Similarity	NPC168753
0.913	High Similarity	NPC118274
0.9102	High Similarity	NPC212237
0.9102	High Similarity	NPC116465
0.9085	High Similarity	NPC477565
0.9085	High Similarity	NPC103379
0.9048	High Similarity	NPC22115
0.9048	High Similarity	NPC275680
0.902	High Similarity	NPC428
0.902	High Similarity	NPC135538
0.902	High Similarity	NPC246587
0.902	High Similarity	NPC24233
0.902	High Similarity	NPC476571
0.902	High Similarity	NPC147390
0.9	High Similarity	NPC238530
0.9	High Similarity	NPC276944
0.9	High Similarity	NPC477563
0.9	High Similarity	NPC253043
0.9	High Similarity	NPC306843
0.9	High Similarity	NPC196447
0.9	High Similarity	NPC136508
0.9	High Similarity	NPC13504
0.9	High Similarity	NPC96603
0.9	High Similarity	NPC78222
0.9	High Similarity	NPC232514
0.9	High Similarity	NPC212794
0.8994	High Similarity	NPC206900
0.8994	High Similarity	NPC175890
0.8994	High Similarity	NPC11296
0.8994	High Similarity	NPC274661
0.8994	High Similarity	NPC82457
0.8994	High Similarity	NPC48490
0.8954	High Similarity	NPC321505
0.8954	High Similarity	NPC476144
0.8954	High Similarity	NPC476151
0.8954	High Similarity	NPC179825
0.8954	High Similarity	NPC51957
0.8954	High Similarity	NPC191376
0.8954	High Similarity	NPC106295
0.8954	High Similarity	NPC210437
0.8954	High Similarity	NPC16107
0.8941	High Similarity	NPC60295
0.8941	High Similarity	NPC191132
0.8938	High Similarity	NPC324144
0.8929	High Similarity	NPC302245
0.8929	High Similarity	NPC16357
0.8929	High Similarity	NPC95426
0.8916	High Similarity	NPC474507
0.8896	High Similarity	NPC7467
0.8889	High Similarity	NPC24260
0.8889	High Similarity	NPC145832
0.8889	High Similarity	NPC474931
0.8889	High Similarity	NPC81218
0.8889	High Similarity	NPC306555
0.8889	High Similarity	NPC158376
0.8889	High Similarity	NPC12053
0.8889	High Similarity	NPC117188
0.8889	High Similarity	NPC205421
0.8876	High Similarity	NPC139783
0.8876	High Similarity	NPC65312
0.8875	High Similarity	NPC60186
0.8868	High Similarity	NPC111485
0.8841	High Similarity	NPC198498
0.8841	High Similarity	NPC317145
0.8841	High Similarity	NPC317439
0.8841	High Similarity	NPC63646
0.8841	High Similarity	NPC115284
0.8841	High Similarity	NPC76682
0.8841	High Similarity	NPC227060
0.8841	High Similarity	NPC10908
0.8841	High Similarity	NPC276890
0.8824	High Similarity	NPC185838
0.8816	High Similarity	NPC128019
0.8816	High Similarity	NPC476567
0.8816	High Similarity	NPC136860
0.8812	High Similarity	NPC119649
0.8812	High Similarity	NPC205255
0.8812	High Similarity	NPC235143
0.8812	High Similarity	NPC230956
0.8812	High Similarity	NPC271388
0.8802	High Similarity	NPC32154
0.8795	High Similarity	NPC173416
0.8795	High Similarity	NPC476577
0.8795	High Similarity	NPC148709
0.8788	High Similarity	NPC12424
0.8788	High Similarity	NPC41376
0.8788	High Similarity	NPC129518
0.8788	High Similarity	NPC251580
0.8779	High Similarity	NPC478093
0.8758	High Similarity	NPC79402
0.8758	High Similarity	NPC80759
0.875	High Similarity	NPC329837
0.875	High Similarity	NPC221864
0.8734	High Similarity	NPC477564
0.8734	High Similarity	NPC2295
0.8728	High Similarity	NPC473589
0.8728	High Similarity	NPC85381
0.8728	High Similarity	NPC478092
0.8728	High Similarity	NPC478091
0.8728	High Similarity	NPC30182
0.8704	High Similarity	NPC1229
0.8696	High Similarity	NPC166014
0.8696	High Similarity	NPC27410
0.8683	High Similarity	NPC293093
0.8683	High Similarity	NPC241704
0.8675	High Similarity	NPC2314
0.8671	High Similarity	NPC37272
0.8667	High Similarity	NPC477562
0.8667	High Similarity	NPC109925
0.8667	High Similarity	NPC69712
0.8667	High Similarity	NPC26240
0.8663	High Similarity	NPC82763
0.865	High Similarity	NPC121275
0.865	High Similarity	NPC284183
0.865	High Similarity	NPC4138
0.8623	High Similarity	NPC199465
0.8623	High Similarity	NPC229166
0.8623	High Similarity	NPC128560
0.8621	High Similarity	NPC256124
0.8613	High Similarity	NPC318805
0.8613	High Similarity	NPC41122
0.8608	High Similarity	NPC277669
0.8608	High Similarity	NPC76213
0.8605	High Similarity	NPC476576
0.8605	High Similarity	NPC186546
0.8598	High Similarity	NPC268503
0.8598	High Similarity	NPC256012
0.8598	High Similarity	NPC317272
0.8598	High Similarity	NPC240841
0.8598	High Similarity	NPC42549
0.8598	High Similarity	NPC250846
0.8588	High Similarity	NPC475654
0.858	High Similarity	NPC475479
0.858	High Similarity	NPC205167
0.858	High Similarity	NPC249274
0.858	High Similarity	NPC243454
0.8563	High Similarity	NPC66341
0.8563	High Similarity	NPC477020
0.8563	High Similarity	NPC192135
0.8562	High Similarity	NPC325871

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 NPC24465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	746
0.2-0.3	1161
0.3-0.4	2140
0.4-0.5	2512
0.5-0.6	1537
0.6-0.7	693
0.7-0.8	142
0.8-0.85	12
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9268	High Similarity	NPD8054	Approved
0.9268	High Similarity	NPD8053	Approved
0.8954	High Similarity	NPD4584	Approved
0.8841	High Similarity	NPD8099	Discontinued
0.8841	High Similarity	NPD8251	Approved
0.8841	High Similarity	NPD8252	Approved
0.8788	High Similarity	NPD8156	Discontinued
0.8562	High Similarity	NPD4664	Clinical (unspecified phase)
0.8519	High Similarity	NPD6788	Approved
0.8272	Intermediate Similarity	NPD4773	Phase 2
0.8272	Intermediate Similarity	NPD4772	Phase 2
0.8263	Intermediate Similarity	NPD4010	Discontinued
0.8221	Intermediate Similarity	NPD7298	Approved
0.815	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD27	Approved
0.8059	Intermediate Similarity	NPD2489	Approved
0.8059	Intermediate Similarity	NPD2898	Approved
0.8025	Intermediate Similarity	NPD3639	Approved
0.8025	Intermediate Similarity	NPD3640	Phase 3
0.8025	Intermediate Similarity	NPD3641	Approved
0.8024	Intermediate Similarity	NPD4055	Discovery
0.8023	Intermediate Similarity	NPD7906	Approved
0.8012	Intermediate Similarity	NPD1424	Approved
0.8012	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2970	Approved
0.8	Intermediate Similarity	NPD2969	Approved
0.795	Intermediate Similarity	NPD2421	Approved
0.795	Intermediate Similarity	NPD2420	Approved
0.7941	Intermediate Similarity	NPD6071	Discontinued
0.7941	Intermediate Similarity	NPD3051	Approved
0.7937	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4017	Approved
0.7927	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4005	Discontinued
0.7923	Intermediate Similarity	NPD8095	Phase 1
0.7904	Intermediate Similarity	NPD2563	Approved
0.7904	Intermediate Similarity	NPD2560	Approved
0.7898	Intermediate Similarity	NPD7310	Approved
0.7898	Intermediate Similarity	NPD7313	Approved
0.7898	Intermediate Similarity	NPD7312	Approved
0.7898	Intermediate Similarity	NPD4578	Approved
0.7898	Intermediate Similarity	NPD7311	Approved
0.7898	Intermediate Similarity	NPD4577	Approved
0.7865	Intermediate Similarity	NPD4663	Approved
0.7853	Intermediate Similarity	NPD7309	Approved
0.7826	Intermediate Similarity	NPD5241	Discontinued
0.7785	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7124	Phase 2
0.7736	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7831	Phase 2
0.7706	Intermediate Similarity	NPD7833	Phase 2
0.7706	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5177	Phase 3
0.7697	Intermediate Similarity	NPD6030	Approved
0.7697	Intermediate Similarity	NPD6031	Approved
0.7674	Intermediate Similarity	NPD6107	Approved
0.7669	Intermediate Similarity	NPD3845	Phase 1
0.7576	Intermediate Similarity	NPD7447	Phase 1
0.7568	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4675	Approved
0.756	Intermediate Similarity	NPD4678	Approved
0.7543	Intermediate Similarity	NPD4481	Phase 3
0.7542	Intermediate Similarity	NPD7549	Discontinued
0.7529	Intermediate Similarity	NPD4585	Approved
0.7516	Intermediate Similarity	NPD5718	Phase 2
0.7515	Intermediate Similarity	NPD7212	Phase 2
0.7515	Intermediate Similarity	NPD5090	Approved
0.7515	Intermediate Similarity	NPD3124	Discontinued
0.7515	Intermediate Similarity	NPD7213	Phase 3
0.7515	Intermediate Similarity	NPD5089	Approved
0.7514	Intermediate Similarity	NPD5677	Discontinued
0.7513	Intermediate Similarity	NPD5005	Approved
0.7513	Intermediate Similarity	NPD5006	Approved
0.75	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3060	Approved
0.7468	Intermediate Similarity	NPD2674	Phase 3
0.746	Intermediate Similarity	NPD2493	Approved
0.746	Intermediate Similarity	NPD3452	Approved
0.746	Intermediate Similarity	NPD2494	Approved
0.746	Intermediate Similarity	NPD3450	Approved
0.7459	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3027	Phase 3
0.7446	Intermediate Similarity	NPD2490	Approved
0.7446	Intermediate Similarity	NPD2488	Approved
0.7436	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD6297	Approved
0.7429	Intermediate Similarity	NPD4166	Phase 2
0.7427	Intermediate Similarity	NPD2978	Approved
0.7427	Intermediate Similarity	NPD2977	Approved
0.7421	Intermediate Similarity	NPD2238	Phase 2
0.7416	Intermediate Similarity	NPD5313	Approved
0.7416	Intermediate Similarity	NPD5312	Approved
0.7401	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6111	Discontinued
0.7391	Intermediate Similarity	NPD2200	Suspended
0.7389	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4236	Phase 3
0.7378	Intermediate Similarity	NPD4237	Approved
0.7371	Intermediate Similarity	NPD7802	Discontinued
0.7362	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4582	Approved
0.7344	Intermediate Similarity	NPD4583	Approved
0.7341	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6090	Discontinued
0.7312	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1613	Approved
0.7302	Intermediate Similarity	NPD4420	Approved
0.7296	Intermediate Similarity	NPD3145	Approved
0.7296	Intermediate Similarity	NPD3144	Approved
0.7292	Intermediate Similarity	NPD4004	Approved
0.7292	Intermediate Similarity	NPD4002	Approved
0.7289	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6896	Approved
0.7284	Intermediate Similarity	NPD6895	Approved
0.7278	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2122	Discontinued
0.7268	Intermediate Similarity	NPD6851	Approved
0.7268	Intermediate Similarity	NPD6853	Approved
0.7263	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4123	Phase 3
0.725	Intermediate Similarity	NPD4475	Approved
0.725	Intermediate Similarity	NPD4474	Approved
0.7249	Intermediate Similarity	NPD2973	Approved
0.7249	Intermediate Similarity	NPD2975	Approved
0.7249	Intermediate Similarity	NPD2974	Approved
0.7239	Intermediate Similarity	NPD1753	Discontinued
0.7225	Intermediate Similarity	NPD5773	Approved
0.7225	Intermediate Similarity	NPD5772	Approved
0.7209	Intermediate Similarity	NPD6072	Discontinued
0.7202	Intermediate Similarity	NPD7598	Phase 2
0.7172	Intermediate Similarity	NPD7827	Phase 1
0.7169	Intermediate Similarity	NPD4162	Approved
0.715	Intermediate Similarity	NPD7047	Phase 3
0.7143	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4580	Approved
0.7135	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6748	Discontinued
0.712	Intermediate Similarity	NPD2968	Approved
0.712	Intermediate Similarity	NPD2971	Approved
0.7115	Intermediate Similarity	NPD2233	Approved
0.7115	Intermediate Similarity	NPD2232	Approved
0.7115	Intermediate Similarity	NPD2230	Approved
0.7108	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6997	Phase 2
0.7102	Intermediate Similarity	NPD5604	Discontinued
0.7099	Intermediate Similarity	NPD3109	Approved
0.7099	Intermediate Similarity	NPD3110	Approved
0.7095	Intermediate Similarity	NPD5242	Approved
0.7089	Intermediate Similarity	NPD3053	Approved
0.7089	Intermediate Similarity	NPD3055	Approved
0.7086	Intermediate Similarity	NPD5977	Approved
0.7086	Intermediate Similarity	NPD5978	Approved
0.7083	Intermediate Similarity	NPD3692	Discontinued
0.7083	Intermediate Similarity	NPD2677	Approved
0.7063	Intermediate Similarity	NPD4908	Phase 1
0.7059	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2899	Discontinued
0.7041	Intermediate Similarity	NPD6666	Approved
0.7041	Intermediate Similarity	NPD6667	Approved
0.7032	Intermediate Similarity	NPD2668	Approved
0.7032	Intermediate Similarity	NPD2667	Approved
0.7027	Intermediate Similarity	NPD7280	Phase 3
0.7027	Intermediate Similarity	NPD7281	Phase 3
0.7024	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7466	Approved
0.7022	Intermediate Similarity	NPD4666	Phase 3
0.7018	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD823	Approved
0.7012	Intermediate Similarity	NPD2568	Approved
0.7012	Intermediate Similarity	NPD817	Approved
0.7011	Intermediate Similarity	NPD7110	Phase 1
0.7011	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5297	Approved
0.7	Intermediate Similarity	NPD6688	Approved
0.7	Intermediate Similarity	NPD6687	Approved
0.6994	Remote Similarity	NPD824	Approved
0.699	Remote Similarity	NPD4040	Phase 1
0.6989	Remote Similarity	NPD6618	Phase 2
0.6982	Remote Similarity	NPD2219	Phase 1
0.6982	Remote Similarity	NPD5160	Discontinued
0.6981	Remote Similarity	NPD4103	Phase 2
0.6981	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5976	Discontinued
0.6975	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6841	Approved
0.6968	Remote Similarity	NPD6843	Phase 3
0.6968	Remote Similarity	NPD6842	Approved
0.6966	Remote Similarity	NPD5709	Phase 3

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