NPASS Compound

Structure

CID108434 OpenBabel06191715462D 42 47 0 0 1 0 0 0 0 0999 V2000 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 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 6.5000 0.0000 C 0 0 0 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 6.0622 1.5000 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 5.1962 2.0000 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 6.0622 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 1.7321 5.0000 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 3.5000 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 5.0000 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 2.0000 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 6.0000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 6.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 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 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 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 9.5263 1.5000 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 2.5981 6.5000 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 6 1 0 0 0 0 3 20 2 0 0 0 0 4 7 2 0 0 0 0 4 20 1 0 0 0 0 5 8 2 0 0 0 0 5 21 1 0 0 0 0 6 24 2 0 0 0 0 7 24 1 0 0 0 0 8 29 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 35 1 0 0 0 0 12 36 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 21 2 0 0 0 0 15 34 1 0 0 0 0 16 22 2 0 0 0 0 16 32 1 0 0 0 0 17 23 2 0 0 0 0 17 33 1 0 0 0 0 18 25 2 0 0 0 0 18 30 1 0 0 0 0 19 26 2 0 0 0 0 19 31 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 42 1 0 0 0 0 25 27 1 0 0 0 0 26 28 1 0 0 0 0 27 13 1 1 0 0 0 27 35 1 0 0 0 0 28 14 1 1 0 0 0 28 36 1 0 0 0 0 29 34 2 0 0 0 0 29 37 1 0 0 0 0 30 32 2 0 0 0 0 30 38 1 0 0 0 0 31 33 2 0 0 0 0 31 39 1 0 0 0 0 32 40 1 0 0 0 0 33 41 1 0 0 0 0 34 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.26
Volume:	588.379
LogP:	3.666
LogD:	3.572
LogS:	-2.617
# Rotatable Bonds:	8
TPSA:	112.44
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	3.675
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.919
MDCK Permeability:	1.1974320841545705e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.094
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	82.05520629882812%
Volume Distribution (VD):	0.905
Pgp-substrate:	13.013900756835938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.13
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.249
CYP2C19-substrate:	0.356
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.397
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.959
CYP3A4-inhibitor:	0.103
CYP3A4-substrate:	0.928

ADMET: Excretion

Clearance (CL):	9.433
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.931
Human Hepatotoxicity (H-HT):	0.416
Drug-inuced Liver Injury (DILI):	0.464
AMES Toxicity:	0.173
Rat Oral Acute Toxicity:	0.212
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.953
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.436

Download Data

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

Natural Product: NPC108434

Natural Product ID:	NPC108434
*Common Name:**	(1S)-1-[[4-[2-Hydroxy-5-[[(1S)-7-Hydroxy-6-Methoxy-1,2,3,4-Tetrahydroisoquinolin-1-Yl]Methyl]Phenoxy]Phenyl]Methyl]-6-Methoxy-1,2,3,4-Tetrahydroisoquinolin-7-Ol
IUPAC Name:	(1S)-1-[[4-[2-hydroxy-5-[[(1S)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenoxy]phenyl]methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Synonyms:
Standard InCHIKey:	DUBVXSGAOWUPMY-NSOVKSMOSA-N
Standard InCHI:	InChI=1S/C34H36N2O6/c1-40-32-16-22-9-11-35-27(25(22)18-30(32)38)13-20-3-6-24(7-4-20)42-34-15-21(5-8-29(34)37)14-28-26-19-31(39)33(41-2)17-23(26)10-12-36-28/h3-8,15-19,27-28,35-39H,9-14H2,1-2H3/t27-,28-/m0/s1
SMILES:	COc1cc2CCN[C@H](c2cc1O)Cc1ccc(cc1)Oc1cc(ccc1O)C[C@@H]1NCCc2c1cc(O)c(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1375576
PubChem CID:	11957300
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
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2204	Lindera megaphylla	Species	Lauraceae	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
EC50	1
IC50	2
Potency	16

Activity Type	# Activity
Individual Protein	12
Organism	2
Others	4
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[456996]
NPT1038	Individual Protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	28183.8	nM	PMID[456996]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	22387.2	nM	PMID[456996]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[456996]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PMID[456996]
NPT52	Individual Protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	Potency	=	10000.0	nM	PMID[456996]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	35481.3	nM	PMID[456996]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	15811.4	nM	PMID[456996]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[456996]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[456996]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[456996]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[456996]
NPT2	Others	Unspecified		IC50	=	64040.0	nM	PMID[456996]
NPT2	Others	Unspecified		EC50	=	48310.0	nM	PMID[456996]
NPT2	Others	Unspecified		IC50	=	56896.0	nM	PMID[456996]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	414.7	nM	PMID[456996]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	737.5	nM	PMID[456996]
NPT2	Others	Unspecified		Potency	n.a.	366.3	nM	PMID[456996]

☑ 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 NPC108434 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	288
0.1-0.2	1566
0.2-0.3	8847
0.3-0.4	9232
0.4-0.5	6522
0.5-0.6	11535
0.6-0.7	3805
0.7-0.8	583
0.8-0.85	185
0.85-0.9	105
0.9-0.95	20
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475215
0.962	High Similarity	NPC240841
0.962	High Similarity	NPC256012
0.962	High Similarity	NPC42549
0.962	High Similarity	NPC250846
0.962	High Similarity	NPC317272
0.962	High Similarity	NPC268503
0.9494	High Similarity	NPC475393
0.929	High Similarity	NPC48490
0.929	High Similarity	NPC82457
0.929	High Similarity	NPC11296
0.929	High Similarity	NPC175890
0.929	High Similarity	NPC274661
0.9235	High Similarity	NPC191132
0.9235	High Similarity	NPC60295
0.9193	High Similarity	NPC121275
0.9193	High Similarity	NPC284183
0.9193	High Similarity	NPC4138
0.9177	High Similarity	NPC25084
0.9177	High Similarity	NPC247639
0.9048	High Similarity	NPC286119
0.9045	High Similarity	NPC277669
0.9045	High Similarity	NPC76213
0.8994	High Similarity	NPC271013
0.8994	High Similarity	NPC104196
0.8994	High Similarity	NPC229373
0.8994	High Similarity	NPC222661
0.8994	High Similarity	NPC258657
0.8994	High Similarity	NPC311973
0.8994	High Similarity	NPC90998
0.8994	High Similarity	NPC30779
0.8994	High Similarity	NPC290005
0.8994	High Similarity	NPC223690
0.8994	High Similarity	NPC7715
0.8994	High Similarity	NPC182052
0.8994	High Similarity	NPC49075
0.8994	High Similarity	NPC251735
0.8994	High Similarity	NPC15414
0.8994	High Similarity	NPC239824
0.8994	High Similarity	NPC290582
0.8994	High Similarity	NPC185639
0.8994	High Similarity	NPC279228
0.8994	High Similarity	NPC285931
0.8994	High Similarity	NPC328155
0.8994	High Similarity	NPC181796
0.8994	High Similarity	NPC42663
0.8994	High Similarity	NPC54654
0.8994	High Similarity	NPC217748
0.8994	High Similarity	NPC8836
0.897	High Similarity	NPC109925
0.8941	High Similarity	NPC167116
0.8941	High Similarity	NPC254441
0.8941	High Similarity	NPC274716
0.8917	High Similarity	NPC207824
0.8917	High Similarity	NPC60538
0.8908	High Similarity	NPC256124
0.8876	High Similarity	NPC475479
0.8876	High Similarity	NPC243454
0.8861	High Similarity	NPC88249
0.8861	High Similarity	NPC151895
0.8861	High Similarity	NPC97221
0.8861	High Similarity	NPC192768
0.8861	High Similarity	NPC220858
0.8837	High Similarity	NPC116465
0.8837	High Similarity	NPC212237
0.8824	High Similarity	NPC239584
0.8812	High Similarity	NPC477564
0.8812	High Similarity	NPC2295
0.8786	High Similarity	NPC275680
0.8786	High Similarity	NPC22115
0.8758	High Similarity	NPC249797
0.8758	High Similarity	NPC193949
0.8758	High Similarity	NPC184026
0.8758	High Similarity	NPC207757
0.8758	High Similarity	NPC278799
0.8758	High Similarity	NPC172765
0.8758	High Similarity	NPC127674
0.8758	High Similarity	NPC54379
0.8758	High Similarity	NPC5238
0.8758	High Similarity	NPC110416
0.8758	High Similarity	NPC2413
0.8758	High Similarity	NPC469817
0.8758	High Similarity	NPC39701
0.8758	High Similarity	NPC276588
0.8758	High Similarity	NPC204828
0.8758	High Similarity	NPC189266
0.8758	High Similarity	NPC295691
0.8758	High Similarity	NPC187022
0.8758	High Similarity	NPC80129
0.8736	High Similarity	NPC206900
0.8734	High Similarity	NPC24233
0.8734	High Similarity	NPC476571
0.8734	High Similarity	NPC135538
0.8734	High Similarity	NPC147390
0.8734	High Similarity	NPC246587
0.8734	High Similarity	NPC428
0.8675	High Similarity	NPC476573
0.8675	High Similarity	NPC35627
0.8675	High Similarity	NPC81247
0.8671	High Similarity	NPC95426
0.8671	High Similarity	NPC302245
0.8671	High Similarity	NPC179825
0.8671	High Similarity	NPC191376
0.8671	High Similarity	NPC321505
0.8671	High Similarity	NPC16357
0.8636	High Similarity	NPC478093
0.8636	High Similarity	NPC24260
0.8621	High Similarity	NPC65312
0.8621	High Similarity	NPC139783
0.8599	High Similarity	NPC294249
0.8588	High Similarity	NPC478092
0.8588	High Similarity	NPC30182
0.8588	High Similarity	NPC473589
0.8588	High Similarity	NPC478091
0.858	High Similarity	NPC317145
0.858	High Similarity	NPC76682
0.858	High Similarity	NPC276890
0.858	High Similarity	NPC10908
0.858	High Similarity	NPC115284
0.858	High Similarity	NPC63646
0.858	High Similarity	NPC317439
0.858	High Similarity	NPC198498
0.858	High Similarity	NPC227060
0.8544	High Similarity	NPC185838
0.8529	High Similarity	NPC41376
0.8529	High Similarity	NPC477020
0.8529	High Similarity	NPC12424
0.8529	High Similarity	NPC251580
0.8529	High Similarity	NPC192135
0.8529	High Similarity	NPC129518
0.8529	High Similarity	NPC66341
0.8523	High Similarity	NPC281581
0.8521	High Similarity	NPC26240
0.8521	High Similarity	NPC69712
0.8521	High Similarity	NPC477562
0.8485	Intermediate Similarity	NPC111485
0.8475	Intermediate Similarity	NPC318805
0.8475	Intermediate Similarity	NPC41122
0.8462	Intermediate Similarity	NPC66573
0.8447	Intermediate Similarity	NPC103379
0.8447	Intermediate Similarity	NPC477565
0.843	Intermediate Similarity	NPC293093
0.8418	Intermediate Similarity	NPC476567
0.8418	Intermediate Similarity	NPC136860
0.8418	Intermediate Similarity	NPC128019
0.8393	Intermediate Similarity	NPC232514
0.8393	Intermediate Similarity	NPC276944
0.8393	Intermediate Similarity	NPC238530
0.838	Intermediate Similarity	NPC85381
0.8352	Intermediate Similarity	NPC475654
0.8344	Intermediate Similarity	NPC323123
0.8343	Intermediate Similarity	NPC13916
0.8343	Intermediate Similarity	NPC264850
0.8333	Intermediate Similarity	NPC474507
0.8323	Intermediate Similarity	NPC16107
0.8323	Intermediate Similarity	NPC166014
0.8323	Intermediate Similarity	NPC51957
0.8323	Intermediate Similarity	NPC27410
0.8323	Intermediate Similarity	NPC476151
0.8323	Intermediate Similarity	NPC106295
0.8323	Intermediate Similarity	NPC210437
0.8323	Intermediate Similarity	NPC476144
0.8293	Intermediate Similarity	NPC37272
0.8291	Intermediate Similarity	NPC474915
0.8291	Intermediate Similarity	NPC213206
0.8291	Intermediate Similarity	NPC328750
0.8291	Intermediate Similarity	NPC188163
0.8287	Intermediate Similarity	NPC234318
0.8284	Intermediate Similarity	NPC24465
0.828	Intermediate Similarity	NPC211468
0.828	Intermediate Similarity	NPC219233
0.828	Intermediate Similarity	NPC170170
0.8272	Intermediate Similarity	NPC7467
0.8253	Intermediate Similarity	NPC186063
0.8253	Intermediate Similarity	NPC126519
0.8253	Intermediate Similarity	NPC170503
0.8253	Intermediate Similarity	NPC203784
0.8246	Intermediate Similarity	NPC204908
0.8246	Intermediate Similarity	NPC83198
0.8239	Intermediate Similarity	NPC73492
0.8239	Intermediate Similarity	NPC299990
0.8229	Intermediate Similarity	NPC119068
0.8229	Intermediate Similarity	NPC40496
0.8228	Intermediate Similarity	NPC314682
0.8225	Intermediate Similarity	NPC324144
0.8221	Intermediate Similarity	NPC92541
0.8218	Intermediate Similarity	NPC476577
0.8218	Intermediate Similarity	NPC148709
0.8218	Intermediate Similarity	NPC173416
0.8217	Intermediate Similarity	NPC253429
0.8192	Intermediate Similarity	NPC135772
0.8192	Intermediate Similarity	NPC302275
0.8187	Intermediate Similarity	NPC474931
0.8187	Intermediate Similarity	NPC306555
0.8187	Intermediate Similarity	NPC81218
0.8187	Intermediate Similarity	NPC158376
0.8187	Intermediate Similarity	NPC145832
0.8187	Intermediate Similarity	NPC210140
0.8187	Intermediate Similarity	NPC117188
0.8187	Intermediate Similarity	NPC205421

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 NPC108434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	705
0.2-0.3	1112
0.3-0.4	1786
0.4-0.5	2611
0.5-0.6	1816
0.6-0.7	729
0.7-0.8	196
0.8-0.85	17
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8994	High Similarity	NPD8053	Approved
0.8994	High Similarity	NPD8054	Approved
0.8758	High Similarity	NPD7298	Approved
0.858	High Similarity	NPD8099	Discontinued
0.858	High Similarity	NPD8252	Approved
0.858	High Similarity	NPD8251	Approved
0.8529	High Similarity	NPD8156	Discontinued
0.8447	Intermediate Similarity	NPD6031	Approved
0.8447	Intermediate Similarity	NPD6030	Approved
0.8323	Intermediate Similarity	NPD4584	Approved
0.8313	Intermediate Similarity	NPD3845	Phase 1
0.8291	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD4773	Phase 2
0.8242	Intermediate Similarity	NPD4772	Phase 2
0.8229	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7833	Phase 2
0.8214	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7831	Phase 2
0.8086	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6107	Approved
0.7941	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4010	Discontinued
0.7879	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD6851	Approved
0.7833	Intermediate Similarity	NPD6853	Approved
0.7826	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD6297	Approved
0.7791	Intermediate Similarity	NPD4162	Approved
0.7742	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD27	Approved
0.7727	Intermediate Similarity	NPD2489	Approved
0.7713	Intermediate Similarity	NPD8095	Phase 1
0.7711	Intermediate Similarity	NPD7598	Phase 2
0.7705	Intermediate Similarity	NPD7906	Approved
0.7697	Intermediate Similarity	NPD5241	Discontinued
0.7692	Intermediate Similarity	NPD4017	Approved
0.7683	Intermediate Similarity	NPD3060	Approved
0.7679	Intermediate Similarity	NPD3639	Approved
0.7679	Intermediate Similarity	NPD3640	Phase 3
0.7679	Intermediate Similarity	NPD3641	Approved
0.7657	Intermediate Similarity	NPD7802	Discontinued
0.7654	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD2898	Approved
0.7622	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2978	Approved
0.7616	Intermediate Similarity	NPD2977	Approved
0.7614	Intermediate Similarity	NPD3051	Approved
0.7614	Intermediate Similarity	NPD6071	Discontinued
0.7614	Intermediate Similarity	NPD4166	Phase 2
0.7605	Intermediate Similarity	NPD2420	Approved
0.7605	Intermediate Similarity	NPD2421	Approved
0.7582	Intermediate Similarity	NPD7313	Approved
0.7582	Intermediate Similarity	NPD7312	Approved
0.7582	Intermediate Similarity	NPD7311	Approved
0.7582	Intermediate Similarity	NPD7310	Approved
0.7571	Intermediate Similarity	NPD2970	Approved
0.7571	Intermediate Similarity	NPD2969	Approved
0.7556	Intermediate Similarity	NPD7479	Phase 2
0.7541	Intermediate Similarity	NPD7309	Approved
0.7516	Intermediate Similarity	NPD3055	Approved
0.7516	Intermediate Similarity	NPD3053	Approved
0.7515	Intermediate Similarity	NPD7153	Discontinued
0.7515	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5718	Phase 2
0.7485	Intermediate Similarity	NPD5160	Discontinued
0.7484	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5720	Discontinued
0.7452	Intermediate Similarity	NPD5310	Approved
0.7452	Intermediate Similarity	NPD5311	Approved
0.7446	Intermediate Similarity	NPD6618	Phase 2
0.7429	Intermediate Similarity	NPD6788	Approved
0.7403	Intermediate Similarity	NPD4873	Discontinued
0.7403	Intermediate Similarity	NPD6042	Phase 2
0.7403	Intermediate Similarity	NPD42	Phase 2
0.7396	Intermediate Similarity	NPD3124	Discontinued
0.7391	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4578	Approved
0.7391	Intermediate Similarity	NPD4577	Approved
0.7371	Intermediate Similarity	NPD2560	Approved
0.7371	Intermediate Similarity	NPD2563	Approved
0.7366	Intermediate Similarity	NPD4663	Approved
0.7365	Intermediate Similarity	NPD2460	Phase 3
0.7365	Intermediate Similarity	NPD2458	Approved
0.7365	Intermediate Similarity	NPD2459	Approved
0.7353	Intermediate Similarity	NPD2874	Phase 2
0.7346	Intermediate Similarity	NPD2674	Phase 3
0.7337	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD52	Approved
0.731	Intermediate Similarity	NPD7526	Approved
0.731	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5313	Approved
0.7308	Intermediate Similarity	NPD5312	Approved
0.7303	Intermediate Similarity	NPD4666	Phase 3
0.7293	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4083	Discontinued
0.7273	Intermediate Similarity	NPD6895	Approved
0.7273	Intermediate Similarity	NPD6896	Approved
0.7257	Intermediate Similarity	NPD5722	Discontinued
0.7257	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1424	Approved
0.7251	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD2488	Approved
0.7249	Intermediate Similarity	NPD2490	Approved
0.7247	Intermediate Similarity	NPD5709	Phase 3
0.7246	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3530	Approved
0.7239	Intermediate Similarity	NPD3532	Approved
0.7239	Intermediate Similarity	NPD4475	Approved
0.7239	Intermediate Similarity	NPD3531	Approved
0.7239	Intermediate Similarity	NPD4474	Approved
0.7235	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2156	Approved
0.7229	Intermediate Similarity	NPD2154	Approved
0.7229	Intermediate Similarity	NPD2155	Approved
0.7222	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6748	Discontinued
0.7219	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5095	Phase 3
0.7213	Intermediate Similarity	NPD5096	Phase 3
0.7213	Intermediate Similarity	NPD3933	Discontinued
0.7212	Intermediate Similarity	NPD5314	Approved
0.7212	Intermediate Similarity	NPD3054	Approved
0.7212	Intermediate Similarity	NPD3052	Approved
0.7212	Intermediate Similarity	NPD823	Approved
0.7212	Intermediate Similarity	NPD817	Approved
0.7212	Intermediate Similarity	NPD2653	Approved
0.7209	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7037	Approved
0.7184	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3145	Approved
0.7178	Intermediate Similarity	NPD3144	Approved
0.7176	Intermediate Similarity	NPD2677	Approved
0.7168	Intermediate Similarity	NPD2122	Discontinued
0.7168	Intermediate Similarity	NPD5976	Discontinued
0.716	Intermediate Similarity	NPD5061	Approved
0.716	Intermediate Similarity	NPD5062	Approved
0.7158	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3536	Discontinued
0.7151	Intermediate Similarity	NPD4123	Phase 3
0.7143	Intermediate Similarity	NPD8149	Discontinued
0.7143	Intermediate Similarity	NPD7291	Discontinued
0.7143	Intermediate Similarity	NPD4481	Phase 3
0.7134	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3686	Approved
0.7126	Intermediate Similarity	NPD3687	Approved
0.7122	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5773	Approved
0.7119	Intermediate Similarity	NPD5772	Approved
0.7112	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6090	Discontinued
0.7105	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7038	Approved
0.7097	Intermediate Similarity	NPD7039	Approved
0.7091	Intermediate Similarity	NPD3061	Approved
0.7091	Intermediate Similarity	NPD3059	Approved
0.7091	Intermediate Similarity	NPD3062	Approved
0.7083	Intermediate Similarity	NPD3156	Discontinued
0.7079	Intermediate Similarity	NPD7827	Phase 1
0.7076	Intermediate Similarity	NPD3692	Discontinued
0.7073	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4040	Phase 1
0.7069	Intermediate Similarity	NPD4727	Phase 1
0.7065	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7034	Discontinued
0.7059	Intermediate Similarity	NPD5177	Phase 3
0.7052	Intermediate Similarity	NPD7447	Phase 1
0.7039	Intermediate Similarity	NPD7773	Phase 2
0.7037	Intermediate Similarity	NPD6584	Phase 3
0.703	Intermediate Similarity	NPD1132	Approved
0.703	Intermediate Similarity	NPD1136	Approved
0.703	Intermediate Similarity	NPD1130	Approved
0.7024	Intermediate Similarity	NPD7425	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1753	Discontinued
0.7019	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6331	Phase 2
0.7006	Intermediate Similarity	NPD7110	Phase 1
0.7006	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6072	Discontinued
0.7006	Intermediate Similarity	NPD7438	Suspended
0.7005	Intermediate Similarity	NPD2494	Approved
0.7005	Intermediate Similarity	NPD2493	Approved
0.7005	Intermediate Similarity	NPD3452	Approved
0.7005	Intermediate Similarity	NPD3450	Approved
0.7	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1774	Approved
0.6994	Remote Similarity	NPD6087	Phase 1
0.6988	Remote Similarity	NPD3109	Approved
0.6988	Remote Similarity	NPD3110	Approved
0.6977	Remote Similarity	NPD8131	Suspended
0.6977	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5084	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