NPASS Compound

Structure

NPC475393 OpenBabel07101718202D 46 51 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 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 -11.2583 1.5000 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 -9.5263 -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 -5.1962 1.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -8.6603 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 -7.7942 4.5000 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 -6.0622 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 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 -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 -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 -6.0622 1.5000 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 -8.6603 3.0000 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 -6.0622 -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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 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 -9.5263 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 -8.6603 1.0000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 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 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 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 -8.6603 -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 -6.0622 -1.5000 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 10 1 0 0 0 0 7 24 2 0 0 0 0 8 11 2 0 0 0 0 8 24 1 0 0 0 0 9 12 2 0 0 0 0 9 25 1 0 0 0 0 10 28 2 0 0 0 0 11 28 1 0 0 0 0 12 33 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 39 1 0 0 0 0 16 40 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 25 2 0 0 0 0 19 38 1 0 0 0 0 20 26 2 0 0 0 0 20 34 1 0 0 0 0 21 27 2 0 0 0 0 21 35 1 0 0 0 0 22 29 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 26 29 1 0 0 0 0 27 30 1 0 0 0 0 28 46 1 0 0 0 0 29 31 1 0 0 0 0 30 32 1 0 0 0 0 31 17 1 6 0 0 0 31 39 1 0 0 0 0 32 18 1 6 0 0 0 32 40 1 0 0 0 0 33 38 2 0 0 0 0 33 41 1 0 0 0 0 34 36 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 44 1 0 0 0 0 37 45 1 0 0 0 0 38 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.32
Volume:	657.563
LogP:	5.664
LogD:	3.99
LogS:	-4.605
# Rotatable Bonds:	11
TPSA:	70.65
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	3.56
Fsp3:	0.368
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:	-5.899
MDCK Permeability:	3.4433531254762784e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.651
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.152
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	87.72624969482422%
Volume Distribution (VD):	0.88
Pgp-substrate:	2.480311393737793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.128
CYP2C19-substrate:	0.968
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.511
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.971
CYP3A4-inhibitor:	0.261
CYP3A4-substrate:	0.954

ADMET: Excretion

Clearance (CL):	6.878
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.971
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.293
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.28
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.495

Download Data

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

Natural Product: NPC475393

Natural Product ID:	NPC475393
*Common Name:**	Pampulhamine
IUPAC Name:	(1R)-1-[[3-[4-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenoxy]-4-methoxyphenyl]methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Synonyms:	Pampulhamine
Standard InCHIKey:	IUALMDJBFWMRDF-ROJLCIKYSA-N
Standard InCHI:	InChI=1S/C38H44N2O6/c1-40-16-14-27-21-35(43-4)37(45-6)23-30(27)32(40)18-25-9-12-33(41-2)38(19-25)46-28-10-7-24(8-11-28)17-31-29-22-36(44-5)34(42-3)20-26(29)13-15-39-31/h7-12,19-23,31-32,39H,13-18H2,1-6H3/t31-,32-/m1/s1
SMILES:	COc1ccc(cc1Oc1ccc(cc1)C[C@H]1NCCc2c1cc(OC)c(c2)OC)C[C@H]1N(C)CCc2c1cc(OC)c(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504801
PubChem CID:	13992155
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	=	84200.0	nM	PMID[505303]
NPT2	Others	Unspecified		Ratio IC50	>	1.2	n.a.	PMID[505303]

☑ 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 NPC475393 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	341
0.1-0.2	1757
0.2-0.3	11019
0.3-0.4	6838
0.4-0.5	8191
0.5-0.6	11273
0.6-0.7	2490
0.7-0.8	524
0.8-0.85	177
0.85-0.9	70
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC247639
0.9669	High Similarity	NPC25084
0.9494	High Similarity	NPC108434
0.9494	High Similarity	NPC475215
0.9321	High Similarity	NPC475479
0.9321	High Similarity	NPC243454
0.9264	High Similarity	NPC239584
0.9241	High Similarity	NPC268503
0.9241	High Similarity	NPC42549
0.9241	High Similarity	NPC256012
0.9241	High Similarity	NPC240841
0.9241	High Similarity	NPC317272
0.9241	High Similarity	NPC250846
0.9221	High Similarity	NPC187022
0.9221	High Similarity	NPC80129
0.9012	High Similarity	NPC317145
0.9012	High Similarity	NPC317439
0.9012	High Similarity	NPC115284
0.9012	High Similarity	NPC76682
0.9012	High Similarity	NPC276890
0.9012	High Similarity	NPC10908
0.9012	High Similarity	NPC198498
0.9012	High Similarity	NPC227060
0.9012	High Similarity	NPC63646
0.8957	High Similarity	NPC251580
0.8957	High Similarity	NPC41376
0.8957	High Similarity	NPC129518
0.8957	High Similarity	NPC12424
0.8935	High Similarity	NPC175890
0.8935	High Similarity	NPC11296
0.8935	High Similarity	NPC82457
0.8935	High Similarity	NPC48490
0.8935	High Similarity	NPC274661
0.8935	High Similarity	NPC281581
0.8882	High Similarity	NPC60295
0.8882	High Similarity	NPC191132
0.8874	High Similarity	NPC476567
0.8874	High Similarity	NPC128019
0.8874	High Similarity	NPC136860
0.8848	High Similarity	NPC293093
0.882	High Similarity	NPC284183
0.882	High Similarity	NPC121275
0.882	High Similarity	NPC4138
0.8779	High Similarity	NPC256124
0.8766	High Similarity	NPC106295
0.8766	High Similarity	NPC476144
0.8766	High Similarity	NPC51957
0.8766	High Similarity	NPC210437
0.8766	High Similarity	NPC16107
0.8742	High Similarity	NPC474915
0.8742	High Similarity	NPC328750
0.8742	High Similarity	NPC188163
0.8742	High Similarity	NPC213206
0.871	High Similarity	NPC7467
0.869	High Similarity	NPC286119
0.8675	High Similarity	NPC314682
0.8654	High Similarity	NPC60538
0.8654	High Similarity	NPC92541
0.8654	High Similarity	NPC207824
0.8639	High Similarity	NPC285931
0.8639	High Similarity	NPC229373
0.8639	High Similarity	NPC73492
0.8639	High Similarity	NPC54654
0.8639	High Similarity	NPC258657
0.8639	High Similarity	NPC299990
0.8639	High Similarity	NPC328155
0.8639	High Similarity	NPC182052
0.8639	High Similarity	NPC49075
0.8639	High Similarity	NPC217748
0.8639	High Similarity	NPC271013
0.8639	High Similarity	NPC251735
0.8639	High Similarity	NPC311973
0.8639	High Similarity	NPC42663
0.8639	High Similarity	NPC8836
0.8639	High Similarity	NPC290582
0.8639	High Similarity	NPC30779
0.8639	High Similarity	NPC181796
0.8639	High Similarity	NPC239824
0.8639	High Similarity	NPC90998
0.8639	High Similarity	NPC15414
0.8639	High Similarity	NPC290005
0.8639	High Similarity	NPC104196
0.8639	High Similarity	NPC223690
0.8639	High Similarity	NPC185639
0.8639	High Similarity	NPC7715
0.8639	High Similarity	NPC279228
0.8639	High Similarity	NPC222661
0.8606	High Similarity	NPC109925
0.8588	High Similarity	NPC254441
0.8588	High Similarity	NPC302275
0.8588	High Similarity	NPC167116
0.8588	High Similarity	NPC274716
0.8562	High Similarity	NPC170503
0.8562	High Similarity	NPC126519
0.8562	High Similarity	NPC203784
0.8544	High Similarity	NPC76213
0.8544	High Similarity	NPC277669
0.8543	High Similarity	NPC253429
0.8538	High Similarity	NPC95426
0.8538	High Similarity	NPC16357
0.8538	High Similarity	NPC302245
0.8526	High Similarity	NPC144863
0.8488	Intermediate Similarity	NPC65312
0.8488	Intermediate Similarity	NPC212237
0.8488	Intermediate Similarity	NPC116465
0.8488	Intermediate Similarity	NPC139783
0.8481	Intermediate Similarity	NPC97221
0.8481	Intermediate Similarity	NPC88249
0.8481	Intermediate Similarity	NPC220858
0.8481	Intermediate Similarity	NPC192768
0.8481	Intermediate Similarity	NPC151895
0.8471	Intermediate Similarity	NPC195538
0.8457	Intermediate Similarity	NPC216816
0.8439	Intermediate Similarity	NPC22115
0.8439	Intermediate Similarity	NPC275680
0.843	Intermediate Similarity	NPC249996
0.8421	Intermediate Similarity	NPC476202
0.8397	Intermediate Similarity	NPC185838
0.8391	Intermediate Similarity	NPC206900
0.8385	Intermediate Similarity	NPC184026
0.8385	Intermediate Similarity	NPC295691
0.8385	Intermediate Similarity	NPC127674
0.8385	Intermediate Similarity	NPC278799
0.8385	Intermediate Similarity	NPC41178
0.8385	Intermediate Similarity	NPC5238
0.8385	Intermediate Similarity	NPC2413
0.8385	Intermediate Similarity	NPC216459
0.8385	Intermediate Similarity	NPC276588
0.8385	Intermediate Similarity	NPC172765
0.8385	Intermediate Similarity	NPC204828
0.8385	Intermediate Similarity	NPC193949
0.8385	Intermediate Similarity	NPC138487
0.8385	Intermediate Similarity	NPC39701
0.8385	Intermediate Similarity	NPC249797
0.8385	Intermediate Similarity	NPC189266
0.8385	Intermediate Similarity	NPC110416
0.8385	Intermediate Similarity	NPC469817
0.8385	Intermediate Similarity	NPC207757
0.8385	Intermediate Similarity	NPC54379
0.8382	Intermediate Similarity	NPC47077
0.8382	Intermediate Similarity	NPC14507
0.8375	Intermediate Similarity	NPC233029
0.8375	Intermediate Similarity	NPC210148
0.8354	Intermediate Similarity	NPC135538
0.8354	Intermediate Similarity	NPC428
0.8354	Intermediate Similarity	NPC475959
0.8354	Intermediate Similarity	NPC246587
0.8354	Intermediate Similarity	NPC24233
0.8354	Intermediate Similarity	NPC147390
0.8354	Intermediate Similarity	NPC476571
0.8343	Intermediate Similarity	NPC473716
0.8343	Intermediate Similarity	NPC475597
0.8333	Intermediate Similarity	NPC146288
0.8323	Intermediate Similarity	NPC477564
0.8323	Intermediate Similarity	NPC2295
0.8313	Intermediate Similarity	NPC81733
0.8313	Intermediate Similarity	NPC326316
0.8302	Intermediate Similarity	NPC219162
0.8295	Intermediate Similarity	NPC478093
0.8295	Intermediate Similarity	NPC24260
0.8291	Intermediate Similarity	NPC191376
0.8291	Intermediate Similarity	NPC179825
0.8291	Intermediate Similarity	NPC321505
0.8278	Intermediate Similarity	NPC160692
0.8249	Intermediate Similarity	NPC30182
0.8249	Intermediate Similarity	NPC478091
0.8249	Intermediate Similarity	NPC478092
0.8249	Intermediate Similarity	NPC473589
0.8239	Intermediate Similarity	NPC130941
0.8221	Intermediate Similarity	NPC234392
0.8221	Intermediate Similarity	NPC31311
0.8204	Intermediate Similarity	NPC81247
0.8204	Intermediate Similarity	NPC476573
0.8204	Intermediate Similarity	NPC304659
0.8204	Intermediate Similarity	NPC86144
0.8204	Intermediate Similarity	NPC35627
0.8199	Intermediate Similarity	NPC476568
0.8199	Intermediate Similarity	NPC476579
0.8176	Intermediate Similarity	NPC476151
0.8176	Intermediate Similarity	NPC90844
0.8176	Intermediate Similarity	NPC95075
0.8176	Intermediate Similarity	NPC253883
0.8171	Intermediate Similarity	NPC476572
0.816	Intermediate Similarity	NPC99659
0.816	Intermediate Similarity	NPC325871
0.8155	Intermediate Similarity	NPC204947
0.8136	Intermediate Similarity	NPC318805
0.8136	Intermediate Similarity	NPC41122
0.8121	Intermediate Similarity	NPC111485
0.8121	Intermediate Similarity	NPC477080
0.8118	Intermediate Similarity	NPC10871
0.8107	Intermediate Similarity	NPC66573
0.8101	Intermediate Similarity	NPC294249
0.8084	Intermediate Similarity	NPC189470
0.8079	Intermediate Similarity	NPC160193
0.8075	Intermediate Similarity	NPC477565
0.8075	Intermediate Similarity	NPC103379
0.807	Intermediate Similarity	NPC477020
0.807	Intermediate Similarity	NPC66341
0.807	Intermediate Similarity	NPC192135

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 NPC475393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	726
0.2-0.3	1119
0.3-0.4	1676
0.4-0.5	2698
0.5-0.6	1803
0.6-0.7	717
0.7-0.8	198
0.8-0.85	11
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9221	High Similarity	NPD7298	Approved
0.9012	High Similarity	NPD8099	Discontinued
0.9012	High Similarity	NPD8251	Approved
0.9012	High Similarity	NPD8252	Approved
0.8957	High Similarity	NPD8156	Discontinued
0.8774	High Similarity	NPD6030	Approved
0.8774	High Similarity	NPD6031	Approved
0.8766	High Similarity	NPD4584	Approved
0.8742	High Similarity	NPD4664	Clinical (unspecified phase)
0.8639	High Similarity	NPD8053	Approved
0.8639	High Similarity	NPD8054	Approved
0.8364	Intermediate Similarity	NPD6107	Approved
0.8323	Intermediate Similarity	NPD4772	Phase 2
0.8323	Intermediate Similarity	NPD4773	Phase 2
0.8113	Intermediate Similarity	NPD7598	Phase 2
0.8086	Intermediate Similarity	NPD4017	Approved
0.8084	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD3640	Phase 3
0.8075	Intermediate Similarity	NPD3641	Approved
0.8075	Intermediate Similarity	NPD3639	Approved
0.8072	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7833	Phase 2
0.8072	Intermediate Similarity	NPD7831	Phase 2
0.8066	Intermediate Similarity	NPD8095	Phase 1
0.8065	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7802	Discontinued
0.8025	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4166	Phase 2
0.7908	Intermediate Similarity	NPD5718	Phase 2
0.7898	Intermediate Similarity	NPD6851	Approved
0.7898	Intermediate Similarity	NPD6853	Approved
0.7895	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6297	Approved
0.7826	Intermediate Similarity	NPD3845	Phase 1
0.7802	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6788	Approved
0.7797	Intermediate Similarity	NPD6618	Phase 2
0.7791	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3124	Discontinued
0.775	Intermediate Similarity	NPD4162	Approved
0.7725	Intermediate Similarity	NPD5720	Discontinued
0.7658	Intermediate Similarity	NPD6895	Approved
0.7658	Intermediate Similarity	NPD6896	Approved
0.7657	Intermediate Similarity	NPD5312	Approved
0.7657	Intermediate Similarity	NPD5313	Approved
0.7654	Intermediate Similarity	NPD5241	Discontinued
0.7651	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4475	Approved
0.7628	Intermediate Similarity	NPD4474	Approved
0.7622	Intermediate Similarity	NPD1424	Approved
0.7613	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6748	Discontinued
0.7572	Intermediate Similarity	NPD3051	Approved
0.7572	Intermediate Similarity	NPD6071	Discontinued
0.7572	Intermediate Similarity	NPD4010	Discontinued
0.7556	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3531	Approved
0.7516	Intermediate Similarity	NPD3532	Approved
0.7516	Intermediate Similarity	NPD3530	Approved
0.7515	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4481	Phase 3
0.7485	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2653	Approved
0.7473	Intermediate Similarity	NPD7291	Discontinued
0.7469	Intermediate Similarity	NPD7153	Discontinued
0.7452	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5160	Discontinued
0.7429	Intermediate Similarity	NPD2970	Approved
0.7429	Intermediate Similarity	NPD2969	Approved
0.7425	Intermediate Similarity	NPD5976	Discontinued
0.7423	Intermediate Similarity	NPD3060	Approved
0.7416	Intermediate Similarity	NPD7479	Phase 2
0.7405	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2489	Approved
0.7386	Intermediate Similarity	NPD27	Approved
0.738	Intermediate Similarity	NPD7034	Discontinued
0.7377	Intermediate Similarity	NPD7906	Approved
0.7358	Intermediate Similarity	NPD3110	Approved
0.7358	Intermediate Similarity	NPD3109	Approved
0.7353	Intermediate Similarity	NPD7110	Phase 1
0.7353	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2560	Approved
0.7326	Intermediate Similarity	NPD2563	Approved
0.7321	Intermediate Similarity	NPD4727	Phase 1
0.7317	Intermediate Similarity	NPD2459	Approved
0.7317	Intermediate Similarity	NPD2458	Approved
0.7317	Intermediate Similarity	NPD2460	Phase 3
0.731	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2874	Phase 2
0.7303	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7124	Phase 2
0.7288	Intermediate Similarity	NPD2898	Approved
0.7284	Intermediate Similarity	NPD7425	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD42	Phase 2
0.7263	Intermediate Similarity	NPD6042	Phase 2
0.7262	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD52	Approved
0.7262	Intermediate Similarity	NPD7526	Approved
0.7257	Intermediate Similarity	NPD5677	Discontinued
0.7253	Intermediate Similarity	NPD7312	Approved
0.7253	Intermediate Similarity	NPD7311	Approved
0.7253	Intermediate Similarity	NPD7310	Approved
0.7253	Intermediate Similarity	NPD7313	Approved
0.7246	Intermediate Similarity	NPD2420	Approved
0.7246	Intermediate Similarity	NPD2421	Approved
0.7239	Intermediate Similarity	NPD3156	Discontinued
0.7232	Intermediate Similarity	NPD6687	Approved
0.7232	Intermediate Similarity	NPD6688	Approved
0.7225	Intermediate Similarity	NPD5978	Approved
0.7225	Intermediate Similarity	NPD5977	Approved
0.7219	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7309	Approved
0.7209	Intermediate Similarity	NPD1769	Discontinued
0.7209	Intermediate Similarity	NPD5722	Discontinued
0.7204	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7905	Discontinued
0.7186	Intermediate Similarity	NPD8149	Discontinued
0.7186	Intermediate Similarity	NPD2120	Phase 2
0.7178	Intermediate Similarity	NPD2156	Approved
0.7178	Intermediate Similarity	NPD2154	Approved
0.7178	Intermediate Similarity	NPD2155	Approved
0.7168	Intermediate Similarity	NPD2978	Approved
0.7168	Intermediate Similarity	NPD2977	Approved
0.7164	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2986	Phase 2
0.716	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2989	Phase 2
0.7158	Intermediate Similarity	NPD2971	Approved
0.7158	Intermediate Similarity	NPD2968	Approved
0.7152	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4083	Discontinued
0.7134	Intermediate Similarity	NPD4098	Discontinued
0.7118	Intermediate Similarity	NPD2122	Discontinued
0.7111	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD44	Approved
0.7108	Intermediate Similarity	NPD6364	Approved
0.7101	Intermediate Similarity	NPD4123	Phase 3
0.7093	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4180	Approved
0.7093	Intermediate Similarity	NPD6875	Approved
0.7093	Intermediate Similarity	NPD4179	Approved
0.7093	Intermediate Similarity	NPD6876	Approved
0.7083	Intermediate Similarity	NPD6612	Phase 2
0.7083	Intermediate Similarity	NPD5457	Discontinued
0.7081	Intermediate Similarity	NPD2245	Discovery
0.7073	Intermediate Similarity	NPD6380	Phase 1
0.7072	Intermediate Similarity	NPD5096	Phase 3
0.7072	Intermediate Similarity	NPD5095	Phase 3
0.7069	Intermediate Similarity	NPD5772	Approved
0.7069	Intermediate Similarity	NPD5773	Approved
0.7069	Intermediate Similarity	NPD4585	Approved
0.7065	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4577	Approved
0.7065	Intermediate Similarity	NPD4578	Approved
0.7062	Intermediate Similarity	NPD6037	Discontinued
0.7048	Intermediate Similarity	NPD7037	Approved
0.7043	Intermediate Similarity	NPD4663	Approved
0.7035	Intermediate Similarity	NPD6357	Discontinued
0.7025	Intermediate Similarity	NPD3055	Approved
0.7025	Intermediate Similarity	NPD3053	Approved
0.7024	Intermediate Similarity	NPD3692	Discontinued
0.7024	Intermediate Similarity	NPD2677	Approved
0.7019	Intermediate Similarity	NPD7294	Phase 1
0.7019	Intermediate Similarity	NPD1336	Approved
0.7013	Intermediate Similarity	NPD3049	Approved
0.7011	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5061	Approved
0.7006	Intermediate Similarity	NPD5062	Approved
0.7006	Intermediate Similarity	NPD5177	Phase 3
0.7006	Intermediate Similarity	NPD5709	Phase 3
0.7	Intermediate Similarity	NPD7019	Approved
0.7	Intermediate Similarity	NPD7020	Approved
0.6995	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3656	Approved
0.6978	Remote Similarity	NPD3933	Discontinued
0.6978	Remote Similarity	NPD4873	Discontinued
0.6977	Remote Similarity	NPD3686	Approved
0.6977	Remote Similarity	NPD3687	Approved
0.6973	Remote Similarity	NPD7280	Phase 3
0.6973	Remote Similarity	NPD7281	Phase 3
0.6966	Remote Similarity	NPD4666	Phase 3
0.6964	Remote Similarity	NPD6331	Phase 2
0.6964	Remote Similarity	NPD5754	Discontinued
0.6962	Remote Similarity	NPD5310	Approved

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