NPASS Compound

Structure

NPC247639 OpenBabel07101718222D 47 52 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 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 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 -2.5981 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 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 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 6.9282 3.0000 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 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 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 7.7942 2.5000 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 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 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 8.6603 3.0000 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 1.7321 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 40 1 0 0 0 0 2 41 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 44 1 0 0 0 0 6 45 1 0 0 0 0 7 46 1 0 0 0 0 8 11 1 0 0 0 0 8 25 2 0 0 0 0 9 12 2 0 0 0 0 9 25 1 0 0 0 0 10 13 2 0 0 0 0 10 26 1 0 0 0 0 11 29 2 0 0 0 0 12 29 1 0 0 0 0 13 34 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 40 1 0 0 0 0 17 41 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 26 2 0 0 0 0 20 39 1 0 0 0 0 21 27 2 0 0 0 0 21 35 1 0 0 0 0 22 28 2 0 0 0 0 22 36 1 0 0 0 0 23 30 2 0 0 0 0 23 37 1 0 0 0 0 24 31 2 0 0 0 0 24 38 1 0 0 0 0 27 30 1 0 0 0 0 28 31 1 0 0 0 0 29 47 1 0 0 0 0 30 32 1 0 0 0 0 31 33 1 0 0 0 0 32 18 1 6 0 0 0 32 40 1 0 0 0 0 33 19 1 6 0 0 0 33 41 1 0 0 0 0 34 39 2 0 0 0 0 34 42 1 0 0 0 0 35 37 2 0 0 0 0 35 43 1 0 0 0 0 36 38 2 0 0 0 0 36 44 1 0 0 0 0 37 45 1 0 0 0 0 38 46 1 0 0 0 0 39 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.34
Volume:	674.859
LogP:	5.943
LogD:	4.182
LogS:	-4.706
# Rotatable Bonds:	11
TPSA:	61.86
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	3.541
Fsp3:	0.385
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:	-5.811
MDCK Permeability:	3.8331785617629066e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.47
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.72
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.526
Plasma Protein Binding (PPB):	85.44112396240234%
Volume Distribution (VD):	1.372
Pgp-substrate:	3.336388349533081%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.982
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.556
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.973
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.959

ADMET: Excretion

Clearance (CL):	9.19
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.988
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.252
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.191
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.494

Download Data

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

Natural Product: NPC247639

Natural Product ID:	NPC247639
*Common Name:**	O-Methyldauricine
IUPAC Name:	(1R)-1-[[4-[5-[[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-methoxyphenoxy]phenyl]methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Synonyms:	O-Methyldauricine
Standard InCHIKey:	UHYCXSGUNAWVBW-CZNDPXEESA-N
Standard InCHI:	InChI=1S/C39H46N2O6/c1-40-16-14-27-21-35(43-4)37(45-6)23-30(27)32(40)18-25-8-11-29(12-9-25)47-39-20-26(10-13-34(39)42-3)19-33-31-24-38(46-7)36(44-5)22-28(31)15-17-41(33)2/h8-13,20-24,32-33H,14-19H2,1-7H3/t32-,33-/m1/s1
SMILES:	COc1ccc(cc1Oc1ccc(cc1)C[C@H]1N(C)CCc2c1cc(OC)c(c2)OC)C[C@H]1N(C)CCc2c1cc(OC)c(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501861
PubChem CID:	200521
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO31148	Aristolochia gigantea	Species	Aristolochiaceae	Eukaryota	n.a.	stem	n.a.	PMID[21178901]
NPO31148	Aristolochia gigantea	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8676127]

☑ 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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	5800.0	nM	PMID[510605]
NPT2	Others	Unspecified		Ratio IC50	>	17.2	n.a.	PMID[510605]

☑ 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 NPC247639 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	350
0.1-0.2	1678
0.2-0.3	9766
0.3-0.4	8233
0.4-0.5	6859
0.5-0.6	11713
0.6-0.7	3241
0.7-0.8	530
0.8-0.85	157
0.85-0.9	134
0.9-0.95	26
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC25084
0.9669	High Similarity	NPC475393
0.9542	High Similarity	NPC256012
0.9542	High Similarity	NPC250846
0.9542	High Similarity	NPC240841
0.9542	High Similarity	NPC42549
0.9542	High Similarity	NPC317272
0.9542	High Similarity	NPC268503
0.9299	High Similarity	NPC276890
0.9299	High Similarity	NPC10908
0.9299	High Similarity	NPC76682
0.9299	High Similarity	NPC317145
0.9299	High Similarity	NPC63646
0.9299	High Similarity	NPC198498
0.9299	High Similarity	NPC115284
0.9299	High Similarity	NPC317439
0.9299	High Similarity	NPC227060
0.9241	High Similarity	NPC129518
0.9241	High Similarity	NPC12424
0.9241	High Similarity	NPC41376
0.9241	High Similarity	NPC251580
0.9178	High Similarity	NPC128019
0.9178	High Similarity	NPC476567
0.9178	High Similarity	NPC136860
0.9177	High Similarity	NPC108434
0.9177	High Similarity	NPC475215
0.9125	High Similarity	NPC293093
0.906	High Similarity	NPC106295
0.906	High Similarity	NPC51957
0.906	High Similarity	NPC16107
0.906	High Similarity	NPC476144
0.906	High Similarity	NPC210437
0.9041	High Similarity	NPC188163
0.9041	High Similarity	NPC474915
0.9041	High Similarity	NPC213206
0.9041	High Similarity	NPC328750
0.9012	High Similarity	NPC243454
0.9012	High Similarity	NPC475479
0.9	High Similarity	NPC7467
0.8973	High Similarity	NPC314682
0.8957	High Similarity	NPC239584
0.8957	High Similarity	NPC286119
0.894	High Similarity	NPC92541
0.8902	High Similarity	NPC182052
0.8902	High Similarity	NPC290582
0.8902	High Similarity	NPC185639
0.8902	High Similarity	NPC223690
0.8902	High Similarity	NPC54654
0.8902	High Similarity	NPC279228
0.8902	High Similarity	NPC285931
0.8902	High Similarity	NPC271013
0.8902	High Similarity	NPC8836
0.8902	High Similarity	NPC42663
0.8902	High Similarity	NPC258657
0.8902	High Similarity	NPC311973
0.8902	High Similarity	NPC30779
0.8902	High Similarity	NPC90998
0.8902	High Similarity	NPC181796
0.8902	High Similarity	NPC7715
0.8902	High Similarity	NPC217748
0.8902	High Similarity	NPC104196
0.8902	High Similarity	NPC222661
0.8902	High Similarity	NPC49075
0.8902	High Similarity	NPC229373
0.8902	High Similarity	NPC73492
0.8902	High Similarity	NPC239824
0.8902	High Similarity	NPC251735
0.8902	High Similarity	NPC15414
0.8902	High Similarity	NPC290005
0.8902	High Similarity	NPC299990
0.8902	High Similarity	NPC328155
0.8896	High Similarity	NPC80129
0.8896	High Similarity	NPC187022
0.8848	High Similarity	NPC302275
0.8848	High Similarity	NPC167116
0.8848	High Similarity	NPC274716
0.8848	High Similarity	NPC254441
0.8808	High Similarity	NPC144863
0.8795	High Similarity	NPC95426
0.8795	High Similarity	NPC302245
0.8795	High Similarity	NPC16357
0.8758	High Similarity	NPC151895
0.8758	High Similarity	NPC192768
0.8758	High Similarity	NPC88249
0.8758	High Similarity	NPC97221
0.8758	High Similarity	NPC220858
0.8743	High Similarity	NPC116465
0.8743	High Similarity	NPC139783
0.8743	High Similarity	NPC65312
0.8743	High Similarity	NPC212237
0.8727	High Similarity	NPC195538
0.8726	High Similarity	NPC216816
0.869	High Similarity	NPC275680
0.869	High Similarity	NPC22115
0.8683	High Similarity	NPC249996
0.8675	High Similarity	NPC476202
0.8675	High Similarity	NPC185838
0.8654	High Similarity	NPC216459
0.8654	High Similarity	NPC207757
0.8654	High Similarity	NPC278799
0.8654	High Similarity	NPC110416
0.8654	High Similarity	NPC249797
0.8654	High Similarity	NPC138487
0.8654	High Similarity	NPC172765
0.8654	High Similarity	NPC54379
0.8654	High Similarity	NPC41178
0.8654	High Similarity	NPC127674
0.8654	High Similarity	NPC204828
0.8654	High Similarity	NPC5238
0.8654	High Similarity	NPC2413
0.8654	High Similarity	NPC469817
0.8654	High Similarity	NPC39701
0.8654	High Similarity	NPC276588
0.8654	High Similarity	NPC295691
0.8654	High Similarity	NPC189266
0.8654	High Similarity	NPC193949
0.8654	High Similarity	NPC184026
0.8645	High Similarity	NPC233029
0.8645	High Similarity	NPC210148
0.8639	High Similarity	NPC274661
0.8639	High Similarity	NPC206900
0.8639	High Similarity	NPC11296
0.8639	High Similarity	NPC281581
0.8639	High Similarity	NPC175890
0.8639	High Similarity	NPC82457
0.8639	High Similarity	NPC48490
0.8631	High Similarity	NPC14507
0.8631	High Similarity	NPC47077
0.8627	High Similarity	NPC24233
0.8627	High Similarity	NPC147390
0.8627	High Similarity	NPC476571
0.8627	High Similarity	NPC246587
0.8627	High Similarity	NPC428
0.8627	High Similarity	NPC135538
0.8627	High Similarity	NPC475959
0.8599	High Similarity	NPC146288
0.8588	High Similarity	NPC191132
0.8588	High Similarity	NPC473716
0.8588	High Similarity	NPC60295
0.8588	High Similarity	NPC475597
0.8581	High Similarity	NPC326316
0.8581	High Similarity	NPC81733
0.8571	High Similarity	NPC219162
0.8562	High Similarity	NPC321505
0.8562	High Similarity	NPC179825
0.8562	High Similarity	NPC191376
0.8538	High Similarity	NPC478093
0.8538	High Similarity	NPC24260
0.8509	High Similarity	NPC4138
0.8509	High Similarity	NPC121275
0.8509	High Similarity	NPC284183
0.8506	High Similarity	NPC130941
0.8488	Intermediate Similarity	NPC478092
0.8488	Intermediate Similarity	NPC256124
0.8488	Intermediate Similarity	NPC30182
0.8488	Intermediate Similarity	NPC478091
0.8488	Intermediate Similarity	NPC473589
0.8481	Intermediate Similarity	NPC31311
0.8481	Intermediate Similarity	NPC234392
0.8462	Intermediate Similarity	NPC476579
0.8462	Intermediate Similarity	NPC476568
0.8442	Intermediate Similarity	NPC253883
0.8442	Intermediate Similarity	NPC90844
0.8442	Intermediate Similarity	NPC95075
0.8442	Intermediate Similarity	NPC476151
0.8428	Intermediate Similarity	NPC476572
0.8418	Intermediate Similarity	NPC325871
0.8418	Intermediate Similarity	NPC99659
0.8375	Intermediate Similarity	NPC111485
0.8375	Intermediate Similarity	NPC477080
0.8372	Intermediate Similarity	NPC41122
0.8372	Intermediate Similarity	NPC318805
0.8364	Intermediate Similarity	NPC10871
0.8356	Intermediate Similarity	NPC160193
0.8354	Intermediate Similarity	NPC66573
0.8333	Intermediate Similarity	NPC477565
0.8333	Intermediate Similarity	NPC207824
0.8333	Intermediate Similarity	NPC60538
0.8333	Intermediate Similarity	NPC103379
0.8312	Intermediate Similarity	NPC130926
0.8303	Intermediate Similarity	NPC109925
0.8302	Intermediate Similarity	NPC244112
0.8282	Intermediate Similarity	NPC276944
0.8282	Intermediate Similarity	NPC238530
0.8282	Intermediate Similarity	NPC169743
0.8282	Intermediate Similarity	NPC232514
0.8276	Intermediate Similarity	NPC85381
0.825	Intermediate Similarity	NPC126519
0.825	Intermediate Similarity	NPC203784
0.825	Intermediate Similarity	NPC170503
0.8249	Intermediate Similarity	NPC475654
0.8232	Intermediate Similarity	NPC264850
0.8232	Intermediate Similarity	NPC13916
0.8228	Intermediate Similarity	NPC277669
0.8228	Intermediate Similarity	NPC76213
0.8221	Intermediate Similarity	NPC233650
0.8219	Intermediate Similarity	NPC172403
0.8212	Intermediate Similarity	NPC253429
0.821	Intermediate Similarity	NPC166014
0.821	Intermediate Similarity	NPC306902

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 NPC247639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	782
0.2-0.3	1066
0.3-0.4	1733
0.4-0.5	2625
0.5-0.6	1791
0.6-0.7	709
0.7-0.8	200
0.8-0.85	25
0.85-0.9	11
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9299	High Similarity	NPD8099	Discontinued
0.9299	High Similarity	NPD8252	Approved
0.9299	High Similarity	NPD8251	Approved
0.9241	High Similarity	NPD8156	Discontinued
0.906	High Similarity	NPD4584	Approved
0.9041	High Similarity	NPD4664	Clinical (unspecified phase)
0.8902	High Similarity	NPD8053	Approved
0.8902	High Similarity	NPD8054	Approved
0.8896	High Similarity	NPD7298	Approved
0.859	High Similarity	NPD4773	Phase 2
0.859	High Similarity	NPD4772	Phase 2
0.8452	Intermediate Similarity	NPD6031	Approved
0.8452	Intermediate Similarity	NPD6030	Approved
0.8344	Intermediate Similarity	NPD4017	Approved
0.8333	Intermediate Similarity	NPD3640	Phase 3
0.8333	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3639	Approved
0.8333	Intermediate Similarity	NPD3641	Approved
0.8333	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7831	Phase 2
0.8323	Intermediate Similarity	NPD7833	Phase 2
0.8295	Intermediate Similarity	NPD8095	Phase 1
0.8282	Intermediate Similarity	NPD7802	Discontinued
0.8176	Intermediate Similarity	NPD5718	Phase 2
0.8171	Intermediate Similarity	NPD6107	Approved
0.8163	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6788	Approved
0.8025	Intermediate Similarity	NPD3124	Discontinued
0.8023	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD6895	Approved
0.7908	Intermediate Similarity	NPD6896	Approved
0.7898	Intermediate Similarity	NPD5241	Discontinued
0.7888	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5312	Approved
0.7882	Intermediate Similarity	NPD5313	Approved
0.7881	Intermediate Similarity	NPD4475	Approved
0.7881	Intermediate Similarity	NPD4474	Approved
0.7867	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6748	Discontinued
0.7799	Intermediate Similarity	NPD7598	Phase 2
0.7798	Intermediate Similarity	NPD6071	Discontinued
0.7798	Intermediate Similarity	NPD3051	Approved
0.7798	Intermediate Similarity	NPD4010	Discontinued
0.7798	Intermediate Similarity	NPD4166	Phase 2
0.775	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD4481	Phase 3
0.7701	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7291	Discontinued
0.7661	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2969	Approved
0.7647	Intermediate Similarity	NPD2970	Approved
0.7614	Intermediate Similarity	NPD6851	Approved
0.7614	Intermediate Similarity	NPD6853	Approved
0.7602	Intermediate Similarity	NPD27	Approved
0.7602	Intermediate Similarity	NPD2489	Approved
0.76	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3109	Approved
0.7597	Intermediate Similarity	NPD3110	Approved
0.7586	Intermediate Similarity	NPD6297	Approved
0.7584	Intermediate Similarity	NPD7906	Approved
0.7576	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7110	Phase 1
0.7562	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2560	Approved
0.7545	Intermediate Similarity	NPD2563	Approved
0.753	Intermediate Similarity	NPD5720	Discontinued
0.753	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7124	Phase 2
0.7516	Intermediate Similarity	NPD3845	Phase 1
0.7514	Intermediate Similarity	NPD6618	Phase 2
0.75	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2898	Approved
0.7485	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5677	Discontinued
0.7469	Intermediate Similarity	NPD2420	Approved
0.7469	Intermediate Similarity	NPD2421	Approved
0.7458	Intermediate Similarity	NPD7310	Approved
0.7458	Intermediate Similarity	NPD7312	Approved
0.7458	Intermediate Similarity	NPD7311	Approved
0.7458	Intermediate Similarity	NPD7313	Approved
0.7442	Intermediate Similarity	NPD6688	Approved
0.7442	Intermediate Similarity	NPD6687	Approved
0.744	Intermediate Similarity	NPD5977	Approved
0.744	Intermediate Similarity	NPD5978	Approved
0.7439	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4162	Approved
0.7434	Intermediate Similarity	NPD7905	Discontinued
0.7416	Intermediate Similarity	NPD7309	Approved
0.7368	Intermediate Similarity	NPD4098	Discontinued
0.736	Intermediate Similarity	NPD2971	Approved
0.736	Intermediate Similarity	NPD2968	Approved
0.7333	Intermediate Similarity	NPD2122	Discontinued
0.7329	Intermediate Similarity	NPD44	Approved
0.7329	Intermediate Similarity	NPD6364	Approved
0.7317	Intermediate Similarity	NPD1424	Approved
0.7317	Intermediate Similarity	NPD4123	Phase 3
0.7314	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6875	Approved
0.7305	Intermediate Similarity	NPD6876	Approved
0.7305	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7034	Discontinued
0.7278	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5772	Approved
0.7278	Intermediate Similarity	NPD5773	Approved
0.7267	Intermediate Similarity	NPD7037	Approved
0.7267	Intermediate Similarity	NPD7153	Discontinued
0.7263	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4577	Approved
0.7263	Intermediate Similarity	NPD4578	Approved
0.7246	Intermediate Similarity	NPD6357	Discontinued
0.7244	Intermediate Similarity	NPD7294	Phase 1
0.7239	Intermediate Similarity	NPD3692	Discontinued
0.7238	Intermediate Similarity	NPD4663	Approved
0.7222	Intermediate Similarity	NPD5177	Phase 3
0.7213	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3656	Approved
0.7197	Intermediate Similarity	NPD3532	Approved
0.7197	Intermediate Similarity	NPD3531	Approved
0.7197	Intermediate Similarity	NPD3530	Approved
0.7191	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6331	Phase 2
0.7178	Intermediate Similarity	NPD5754	Discontinued
0.7178	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2653	Approved
0.7169	Intermediate Similarity	NPD6090	Discontinued
0.7167	Intermediate Similarity	NPD7280	Phase 3
0.7167	Intermediate Similarity	NPD7281	Phase 3
0.716	Intermediate Similarity	NPD7438	Suspended
0.7159	Intermediate Similarity	NPD5938	Phase 3
0.7151	Intermediate Similarity	NPD4055	Discovery
0.7151	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3920	Phase 2
0.7135	Intermediate Similarity	NPD7479	Phase 2
0.7134	Intermediate Similarity	NPD5160	Discontinued
0.7133	Intermediate Similarity	NPD6382	Discontinued
0.7133	Intermediate Similarity	NPD2595	Approved
0.7133	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2594	Approved
0.7126	Intermediate Similarity	NPD5976	Discontinued
0.7125	Intermediate Similarity	NPD7119	Phase 2
0.712	Intermediate Similarity	NPD2490	Approved
0.712	Intermediate Similarity	NPD2488	Approved
0.7117	Intermediate Similarity	NPD4236	Phase 3
0.7117	Intermediate Similarity	NPD4237	Approved
0.7117	Intermediate Similarity	NPD3060	Approved
0.711	Intermediate Similarity	NPD8245	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7447	Phase 1
0.7101	Intermediate Similarity	NPD4678	Approved
0.7101	Intermediate Similarity	NPD4675	Approved
0.7097	Intermediate Similarity	NPD6584	Phase 3
0.7097	Intermediate Similarity	NPD7247	Discontinued
0.7089	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2674	Phase 3
0.7089	Intermediate Similarity	NPD7477	Discontinued
0.7083	Intermediate Similarity	NPD4210	Discontinued
0.7081	Intermediate Similarity	NPD3923	Approved
0.7081	Intermediate Similarity	NPD6380	Phase 1
0.7081	Intermediate Similarity	NPD3922	Approved
0.7081	Intermediate Similarity	NPD1753	Discontinued
0.7081	Intermediate Similarity	NPD3921	Approved
0.7081	Intermediate Similarity	NPD3924	Approved
0.7075	Intermediate Similarity	NPD5283	Phase 1
0.7074	Intermediate Similarity	NPD4420	Approved
0.7069	Intermediate Similarity	NPD6037	Discontinued
0.7067	Intermediate Similarity	NPD6581	Approved
0.7067	Intermediate Similarity	NPD6580	Approved
0.7066	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD52	Approved
0.7066	Intermediate Similarity	NPD7526	Approved
0.7063	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6385	Approved
0.7059	Intermediate Similarity	NPD6386	Approved
0.705	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4005	Discontinued
0.7039	Intermediate Similarity	NPD3885	Approved
0.7037	Intermediate Similarity	NPD2161	Phase 2
0.7037	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6063	Approved
0.7025	Intermediate Similarity	NPD5111	Phase 2
0.7025	Intermediate Similarity	NPD5109	Approved
0.7025	Intermediate Similarity	NPD5110	Phase 2
0.7024	Intermediate Similarity	NPD7427	Discontinued
0.7024	Intermediate Similarity	NPD4727	Phase 1
0.7022	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2975	Approved
0.7021	Intermediate Similarity	NPD2974	Approved
0.7021	Intermediate Similarity	NPD5564	Approved
0.7021	Intermediate Similarity	NPD2973	Approved
0.702	Intermediate Similarity	NPD8149	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