NPASS Compound

Structure

NPC264850 OpenBabel07101718322D 27 30 0 0 1 0 0 0 0 0999 V2000 -6.9282 4.0000 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 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -4.3301 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 2 0 0 0 0 5 12 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 15 2 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 6 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 23 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:	2.245
LogD:	2.632
LogS:	-2.2
# 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:	3.104
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:	-4.981
MDCK Permeability:	2.2929241822566837e-05
Pgp-inhibitor:	0.557
Pgp-substrate:	0.881
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	80.22008514404297%
Volume Distribution (VD):	0.994
Pgp-substrate:	21.405439376831055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.766
CYP2D6-inhibitor:	0.4
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	13.459
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.374
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.535
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC264850

Natural Product ID:	NPC264850
*Common Name:**	(-)-Thaicanine
IUPAC Name:	(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-4-ol
Synonyms:	(-)-Thaicanine
Standard InCHIKey:	CKDHRRPIIGEUGN-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C21H25NO5/c1-24-17-6-5-12-9-16-14-10-18(25-2)21(27-4)19(23)13(14)7-8-22(16)11-15(12)20(17)26-3/h5-6,10,16,23H,7-9,11H2,1-4H3/t16-/m0/s1
SMILES:	COc1c(OC)ccc2c1CN1CCc3c([C@@H]1C2)cc(c(c3O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465823
PubChem CID:	14412741
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	=	1610.0	ng/ml	PMID[515184]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	550.0	ng/ml	PMID[515184]
NPT2	Others	Unspecified		Ratio ED50	>	12.0	n.a.	PMID[515184]
NPT2	Others	Unspecified		Ratio ED50	>	36.0	n.a.	PMID[515184]

☑ 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 NPC264850 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	320
0.1-0.2	1541
0.2-0.3	7914
0.3-0.4	10363
0.4-0.5	5160
0.5-0.6	8689
0.6-0.7	6721
0.7-0.8	1529
0.8-0.85	214
0.85-0.9	145
0.9-0.95	96
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC13916
0.9935	High Similarity	NPC24465
0.9494	High Similarity	NPC83198
0.9494	High Similarity	NPC204908
0.9477	High Similarity	NPC469817
0.9477	High Similarity	NPC2413
0.9477	High Similarity	NPC278799
0.9477	High Similarity	NPC39701
0.9477	High Similarity	NPC127674
0.9477	High Similarity	NPC5238
0.9477	High Similarity	NPC189266
0.9477	High Similarity	NPC193949
0.9477	High Similarity	NPC184026
0.9477	High Similarity	NPC207757
0.9477	High Similarity	NPC249797
0.9477	High Similarity	NPC276588
0.9477	High Similarity	NPC204828
0.9477	High Similarity	NPC172765
0.9477	High Similarity	NPC54379
0.9477	High Similarity	NPC295691
0.9477	High Similarity	NPC110416
0.9329	High Similarity	NPC229373
0.9329	High Similarity	NPC251735
0.9329	High Similarity	NPC223690
0.9329	High Similarity	NPC328155
0.9329	High Similarity	NPC42663
0.9329	High Similarity	NPC222661
0.9329	High Similarity	NPC49075
0.9329	High Similarity	NPC311973
0.9329	High Similarity	NPC7715
0.9329	High Similarity	NPC258657
0.9329	High Similarity	NPC90998
0.9329	High Similarity	NPC15414
0.9329	High Similarity	NPC285931
0.9329	High Similarity	NPC54654
0.9329	High Similarity	NPC290005
0.9329	High Similarity	NPC239824
0.9329	High Similarity	NPC290582
0.9329	High Similarity	NPC104196
0.9329	High Similarity	NPC185639
0.9329	High Similarity	NPC181796
0.9329	High Similarity	NPC279228
0.9329	High Similarity	NPC217748
0.9329	High Similarity	NPC271013
0.9329	High Similarity	NPC8836
0.9329	High Similarity	NPC182052
0.9317	High Similarity	NPC152680
0.9317	High Similarity	NPC190783
0.9317	High Similarity	NPC232386
0.9273	High Similarity	NPC274716
0.9273	High Similarity	NPC254441
0.9273	High Similarity	NPC167116
0.9268	High Similarity	NPC286119
0.9255	High Similarity	NPC239775
0.9216	High Similarity	NPC220858
0.9216	High Similarity	NPC192768
0.9216	High Similarity	NPC88249
0.9216	High Similarity	NPC97221
0.9216	High Similarity	NPC151895
0.9212	High Similarity	NPC30779
0.9193	High Similarity	NPC168753
0.9193	High Similarity	NPC118274
0.9162	High Similarity	NPC212237
0.9162	High Similarity	NPC116465
0.915	High Similarity	NPC477565
0.915	High Similarity	NPC103379
0.9107	High Similarity	NPC22115
0.9107	High Similarity	NPC275680
0.9085	High Similarity	NPC147390
0.9085	High Similarity	NPC246587
0.9085	High Similarity	NPC428
0.9085	High Similarity	NPC24233
0.9085	High Similarity	NPC476571
0.9085	High Similarity	NPC135538
0.9062	High Similarity	NPC238530
0.9062	High Similarity	NPC232514
0.9062	High Similarity	NPC276944
0.9053	High Similarity	NPC274661
0.9053	High Similarity	NPC206900
0.9053	High Similarity	NPC175890
0.9053	High Similarity	NPC48490
0.9053	High Similarity	NPC11296
0.9053	High Similarity	NPC82457
0.902	High Similarity	NPC476151
0.902	High Similarity	NPC51957
0.902	High Similarity	NPC16107
0.902	High Similarity	NPC476144
0.902	High Similarity	NPC191376
0.902	High Similarity	NPC210437
0.902	High Similarity	NPC179825
0.902	High Similarity	NPC106295
0.902	High Similarity	NPC321505
0.9	High Similarity	NPC191132
0.9	High Similarity	NPC60295
0.8988	High Similarity	NPC95426
0.8988	High Similarity	NPC16357
0.8988	High Similarity	NPC302245
0.8976	High Similarity	NPC474507
0.8961	High Similarity	NPC7467
0.8951	High Similarity	NPC145832
0.8951	High Similarity	NPC205421
0.8951	High Similarity	NPC474931
0.8951	High Similarity	NPC306555
0.8951	High Similarity	NPC12053
0.8951	High Similarity	NPC81218
0.8951	High Similarity	NPC117188
0.8951	High Similarity	NPC158376
0.8947	High Similarity	NPC24260
0.8944	High Similarity	NPC136508
0.8944	High Similarity	NPC196447
0.8944	High Similarity	NPC477563
0.8944	High Similarity	NPC96603
0.8944	High Similarity	NPC212794
0.8944	High Similarity	NPC306843
0.8944	High Similarity	NPC78222
0.8944	High Similarity	NPC13504
0.8944	High Similarity	NPC253043
0.8938	High Similarity	NPC60186
0.8935	High Similarity	NPC139783
0.8935	High Similarity	NPC65312
0.8902	High Similarity	NPC63646
0.8902	High Similarity	NPC76682
0.8902	High Similarity	NPC317145
0.8902	High Similarity	NPC115284
0.8902	High Similarity	NPC317439
0.8902	High Similarity	NPC10908
0.8902	High Similarity	NPC276890
0.8902	High Similarity	NPC198498
0.8902	High Similarity	NPC227060
0.8889	High Similarity	NPC185838
0.8882	High Similarity	NPC324144
0.8875	High Similarity	NPC205255
0.8875	High Similarity	NPC235143
0.8875	High Similarity	NPC230956
0.8875	High Similarity	NPC119649
0.8875	High Similarity	NPC271388
0.8862	High Similarity	NPC32154
0.8855	High Similarity	NPC476577
0.8855	High Similarity	NPC148709
0.8855	High Similarity	NPC173416
0.8848	High Similarity	NPC41376
0.8848	High Similarity	NPC12424
0.8848	High Similarity	NPC129518
0.8848	High Similarity	NPC251580
0.8837	High Similarity	NPC478093
0.882	High Similarity	NPC79402
0.882	High Similarity	NPC80759
0.8812	High Similarity	NPC221864
0.8812	High Similarity	NPC111485
0.8812	High Similarity	NPC329837
0.8797	High Similarity	NPC2295
0.8797	High Similarity	NPC477564
0.8786	High Similarity	NPC85381
0.8786	High Similarity	NPC473589
0.8786	High Similarity	NPC478091
0.8786	High Similarity	NPC30182
0.8786	High Similarity	NPC478092
0.8765	High Similarity	NPC1229
0.8758	High Similarity	NPC136860
0.8758	High Similarity	NPC166014
0.8758	High Similarity	NPC476567
0.8758	High Similarity	NPC27410
0.8758	High Similarity	NPC128019
0.8743	High Similarity	NPC241704
0.8743	High Similarity	NPC293093
0.8735	High Similarity	NPC2314
0.8678	High Similarity	NPC256124
0.8671	High Similarity	NPC41122
0.8671	High Similarity	NPC277669
0.8671	High Similarity	NPC318805
0.8671	High Similarity	NPC76213
0.8659	High Similarity	NPC256012
0.8659	High Similarity	NPC250846
0.8659	High Similarity	NPC42549
0.8659	High Similarity	NPC268503
0.8659	High Similarity	NPC240841
0.8659	High Similarity	NPC317272
0.8644	High Similarity	NPC475654
0.8639	High Similarity	NPC243454
0.8639	High Similarity	NPC475479
0.8627	High Similarity	NPC328750
0.8627	High Similarity	NPC213206
0.8627	High Similarity	NPC188163
0.8627	High Similarity	NPC474915
0.8625	High Similarity	NPC216459
0.8625	High Similarity	NPC138487
0.8625	High Similarity	NPC41178
0.8623	High Similarity	NPC192135
0.8623	High Similarity	NPC477020
0.8623	High Similarity	NPC66341
0.8616	High Similarity	NPC37272
0.8614	High Similarity	NPC69712
0.8614	High Similarity	NPC26240
0.8614	High Similarity	NPC477562
0.8614	High Similarity	NPC109925
0.8613	High Similarity	NPC82763
0.8598	High Similarity	NPC121275
0.8598	High Similarity	NPC4138
0.8598	High Similarity	NPC284183
0.8588	High Similarity	NPC239584

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 NPC264850 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	751
0.2-0.3	1123
0.3-0.4	2035
0.4-0.5	2571
0.5-0.6	1574
0.6-0.7	719
0.7-0.8	154
0.8-0.85	16
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9329	High Similarity	NPD8054	Approved
0.9329	High Similarity	NPD8053	Approved
0.902	High Similarity	NPD4584	Approved
0.8902	High Similarity	NPD8251	Approved
0.8902	High Similarity	NPD8252	Approved
0.8902	High Similarity	NPD8099	Discontinued
0.8848	High Similarity	NPD8156	Discontinued
0.8627	High Similarity	NPD4664	Clinical (unspecified phase)
0.858	High Similarity	NPD6788	Approved
0.8221	Intermediate Similarity	NPD4773	Phase 2
0.8221	Intermediate Similarity	NPD4772	Phase 2
0.8214	Intermediate Similarity	NPD4010	Discontinued
0.8171	Intermediate Similarity	NPD7298	Approved
0.8121	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD2489	Approved
0.8118	Intermediate Similarity	NPD27	Approved
0.8118	Intermediate Similarity	NPD2898	Approved
0.8103	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD4055	Discovery
0.8079	Intermediate Similarity	NPD7906	Approved
0.8075	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1424	Approved
0.8059	Intermediate Similarity	NPD2970	Approved
0.8059	Intermediate Similarity	NPD2969	Approved
0.8012	Intermediate Similarity	NPD2421	Approved
0.8012	Intermediate Similarity	NPD2420	Approved
0.8	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6071	Discontinued
0.8	Intermediate Similarity	NPD3051	Approved
0.7988	Intermediate Similarity	NPD4017	Approved
0.7988	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD8095	Phase 1
0.7975	Intermediate Similarity	NPD3640	Phase 3
0.7975	Intermediate Similarity	NPD3641	Approved
0.7975	Intermediate Similarity	NPD3639	Approved
0.7964	Intermediate Similarity	NPD2563	Approved
0.7964	Intermediate Similarity	NPD2560	Approved
0.7955	Intermediate Similarity	NPD7313	Approved
0.7955	Intermediate Similarity	NPD4577	Approved
0.7955	Intermediate Similarity	NPD7312	Approved
0.7955	Intermediate Similarity	NPD7311	Approved
0.7955	Intermediate Similarity	NPD7310	Approved
0.7955	Intermediate Similarity	NPD4578	Approved
0.7921	Intermediate Similarity	NPD4663	Approved
0.791	Intermediate Similarity	NPD7309	Approved
0.7888	Intermediate Similarity	NPD5241	Discontinued
0.7879	Intermediate Similarity	NPD4005	Discontinued
0.7848	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7124	Phase 2
0.7799	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7831	Phase 2
0.7765	Intermediate Similarity	NPD7833	Phase 2
0.7764	Intermediate Similarity	NPD5177	Phase 3
0.7758	Intermediate Similarity	NPD6030	Approved
0.7758	Intermediate Similarity	NPD6031	Approved
0.773	Intermediate Similarity	NPD3845	Phase 1
0.7636	Intermediate Similarity	NPD7447	Phase 1
0.763	Intermediate Similarity	NPD6107	Approved
0.7622	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4678	Approved
0.7619	Intermediate Similarity	NPD4675	Approved
0.76	Intermediate Similarity	NPD4481	Phase 3
0.7598	Intermediate Similarity	NPD7549	Discontinued
0.758	Intermediate Similarity	NPD5718	Phase 2
0.7576	Intermediate Similarity	NPD7213	Phase 3
0.7576	Intermediate Similarity	NPD3124	Discontinued
0.7576	Intermediate Similarity	NPD7212	Phase 2
0.7572	Intermediate Similarity	NPD5677	Discontinued
0.7566	Intermediate Similarity	NPD5006	Approved
0.7566	Intermediate Similarity	NPD5005	Approved
0.7556	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3060	Approved
0.7532	Intermediate Similarity	NPD2674	Phase 3
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD3452	Approved
0.7513	Intermediate Similarity	NPD3450	Approved
0.7513	Intermediate Similarity	NPD2494	Approved
0.7513	Intermediate Similarity	NPD2493	Approved
0.75	Intermediate Similarity	NPD2488	Approved
0.75	Intermediate Similarity	NPD2490	Approved
0.7486	Intermediate Similarity	NPD6297	Approved
0.7485	Intermediate Similarity	NPD2978	Approved
0.7485	Intermediate Similarity	NPD4585	Approved
0.7485	Intermediate Similarity	NPD2977	Approved
0.7484	Intermediate Similarity	NPD2238	Phase 2
0.7471	Intermediate Similarity	NPD5090	Approved
0.7471	Intermediate Similarity	NPD5089	Approved
0.7458	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2200	Suspended
0.7452	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4237	Approved
0.7439	Intermediate Similarity	NPD4236	Phase 3
0.7429	Intermediate Similarity	NPD7802	Discontinued
0.7423	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4583	Approved
0.7396	Intermediate Similarity	NPD4582	Approved
0.7389	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4166	Phase 2
0.7375	Intermediate Similarity	NPD1613	Approved
0.7375	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5313	Approved
0.7374	Intermediate Similarity	NPD5312	Approved
0.7358	Intermediate Similarity	NPD3145	Approved
0.7358	Intermediate Similarity	NPD3144	Approved
0.7354	Intermediate Similarity	NPD4420	Approved
0.7349	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6896	Approved
0.7346	Intermediate Similarity	NPD6111	Discontinued
0.7346	Intermediate Similarity	NPD6895	Approved
0.7344	Intermediate Similarity	NPD4002	Approved
0.7344	Intermediate Similarity	NPD4004	Approved
0.7342	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2122	Discontinued
0.7322	Intermediate Similarity	NPD6853	Approved
0.7322	Intermediate Similarity	NPD6851	Approved
0.7321	Intermediate Similarity	NPD4123	Phase 3
0.7312	Intermediate Similarity	NPD4474	Approved
0.7312	Intermediate Similarity	NPD4475	Approved
0.7302	Intermediate Similarity	NPD2973	Approved
0.7302	Intermediate Similarity	NPD2975	Approved
0.7302	Intermediate Similarity	NPD2974	Approved
0.7301	Intermediate Similarity	NPD1753	Discontinued
0.7283	Intermediate Similarity	NPD5772	Approved
0.7283	Intermediate Similarity	NPD5773	Approved
0.7278	Intermediate Similarity	NPD6090	Discontinued
0.7267	Intermediate Similarity	NPD6072	Discontinued
0.7262	Intermediate Similarity	NPD7598	Phase 2
0.7229	Intermediate Similarity	NPD4162	Approved
0.7225	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7047	Phase 3
0.7188	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4580	Approved
0.7186	Intermediate Similarity	NPD6748	Discontinued
0.7179	Intermediate Similarity	NPD2232	Approved
0.7179	Intermediate Similarity	NPD2233	Approved
0.7179	Intermediate Similarity	NPD2230	Approved
0.7174	Intermediate Similarity	NPD2971	Approved
0.7174	Intermediate Similarity	NPD2968	Approved
0.7169	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3110	Approved
0.716	Intermediate Similarity	NPD3109	Approved
0.7159	Intermediate Similarity	NPD5604	Discontinued
0.7157	Intermediate Similarity	NPD6997	Phase 2
0.7152	Intermediate Similarity	NPD3055	Approved
0.7152	Intermediate Similarity	NPD3053	Approved
0.7151	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD5977	Approved
0.7143	Intermediate Similarity	NPD5978	Approved
0.7143	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD3692	Discontinued
0.7136	Intermediate Similarity	NPD7827	Phase 1
0.7125	Intermediate Similarity	NPD4908	Phase 1
0.7118	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6667	Approved
0.7101	Intermediate Similarity	NPD6666	Approved
0.7097	Intermediate Similarity	NPD2668	Approved
0.7097	Intermediate Similarity	NPD2667	Approved
0.7094	Intermediate Similarity	NPD2899	Discontinued
0.7083	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7466	Approved
0.7081	Intermediate Similarity	NPD7281	Phase 3
0.7081	Intermediate Similarity	NPD7280	Phase 3
0.7079	Intermediate Similarity	NPD4666	Phase 3
0.7076	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD817	Approved
0.7073	Intermediate Similarity	NPD2568	Approved
0.7073	Intermediate Similarity	NPD823	Approved
0.7069	Intermediate Similarity	NPD7110	Phase 1
0.7069	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5297	Approved
0.7052	Intermediate Similarity	NPD824	Approved
0.7044	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4103	Phase 2
0.7043	Intermediate Similarity	NPD6618	Phase 2
0.7041	Intermediate Similarity	NPD5160	Discontinued
0.7041	Intermediate Similarity	NPD4040	Phase 1
0.7037	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5976	Discontinued
0.7031	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5709	Phase 3
0.7	Intermediate Similarity	NPD3122	Phase 3
0.6995	Remote Similarity	NPD4873	Discontinued
0.6995	Remote Similarity	NPD42	Phase 2
0.6995	Remote Similarity	NPD6042	Phase 2
0.6989	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6658	Clinical (unspecified phase)

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