NPASS Compound

Structure

CID241704 OpenBabel06191716042D 32 36 0 0 1 0 0 0 0 0999 V2000 -5.8301 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7624 2.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6072 2.2233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2016 1.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2678 3.9922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1125 4.1520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8911 1.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8339 0.3592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4855 0.9200 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7642 3.5912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3303 0.7601 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.6808 3.9911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4659 0.6072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8301 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8301 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 17 1 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 23 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 16 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 14 24 1 0 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 17 27 1 6 0 0 0 18 12 1 1 0 0 0 18 32 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 2 0 0 0 0 22 27 1 6 0 0 0 23 28 1 0 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 26 29 2 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	435.2
Volume:	449.326
LogP:	4.689
LogD:	3.819
LogS:	-4.914
# Rotatable Bonds:	2
TPSA:	68.23
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	5.37
Fsp3:	0.423
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	7.47640006011352e-05
Pgp-inhibitor:	0.081
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.209

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.702
Plasma Protein Binding (PPB):	95.7818603515625%
Volume Distribution (VD):	1.581
Pgp-substrate:	4.633122444152832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.206
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.294
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.905
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.545
CYP3A4-substrate:	0.8

ADMET: Excretion

Clearance (CL):	9.25
Half-life (T1/2):	0.233

ADMET: Toxicity

hERG Blockers:	0.748
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.807
Rat Oral Acute Toxicity:	0.229
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.944
Carcinogencity:	0.156
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC241704

Natural Product ID:	NPC241704
*Common Name:**	Vertine
IUPAC Name:	n.a.
Synonyms:	Vertine
Standard InCHIKey:	WCZWUYYJZVBKDZ-VMSBZHFZSA-N
Standard InCHI:	InChI=1S/C26H29NO5/c1-30-24-14-19-20(15-25(24)31-2)22-13-18(12-17-5-3-4-10-27(17)22)32-26(29)9-7-16-6-8-23(28)21(19)11-16/h6-9,11,14-15,17-18,22,28H,3-5,10,12-13H2,1-2H3/p+1/b9-7-/t17-,18+,22+/m1/s1
SMILES:	COc1cc2-c3cc(ccc3O)/C=CC(=O)O[C@H]3C[C@H]4CCCC[NH+]4[C@@H](C3)c2cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173218
PubChem CID:	5315204
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000221] Quinolizidines

*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
NPO12007	Pseudowintera axillaris	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16417306]
NPO26661	Heimia salicifolia	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO18183	Cucumaria japonica	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8984150]
NPO549	Musa X paradisiaca	Strain	Musaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO549	Musa X paradisiaca	Strain	Musaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17697	Galium glaucum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21320	Artabotrys venustus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO549	Musa X paradisiaca	Strain	Musaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17697	Galium glaucum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21320	Artabotrys venustus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18183	Cucumaria japonica	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20520	Arenaria filicaulis	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26661	Heimia salicifolia	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO549	Musa X paradisiaca	Strain	Musaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20372	Ganophyllum giganteum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21320	Artabotrys venustus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17697	Galium glaucum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18335	Vernonia stipulacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14432	Catunaregam nilotica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12007	Pseudowintera axillaris	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20785	Lindsaea ensifolia	Species	Lindsaeaceae	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.76	ug.mL-1	PMID[476198]

☑ 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 NPC241704 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	258
0.1-0.2	1222
0.2-0.3	3689
0.3-0.4	10908
0.4-0.5	7124
0.5-0.6	8649
0.6-0.7	9776
0.7-0.8	817
0.8-0.85	250
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC32154
0.8827	High Similarity	NPC54379
0.8827	High Similarity	NPC249797
0.8827	High Similarity	NPC127674
0.8827	High Similarity	NPC110416
0.8827	High Similarity	NPC207757
0.8827	High Similarity	NPC184026
0.8827	High Similarity	NPC5238
0.8827	High Similarity	NPC469817
0.8827	High Similarity	NPC204828
0.8827	High Similarity	NPC276588
0.8827	High Similarity	NPC172765
0.8827	High Similarity	NPC189266
0.8827	High Similarity	NPC295691
0.8827	High Similarity	NPC193949
0.8827	High Similarity	NPC2413
0.8827	High Similarity	NPC278799
0.8827	High Similarity	NPC39701
0.8743	High Similarity	NPC13916
0.8743	High Similarity	NPC264850
0.8706	High Similarity	NPC2314
0.869	High Similarity	NPC12053
0.869	High Similarity	NPC145832
0.869	High Similarity	NPC81218
0.869	High Similarity	NPC306555
0.869	High Similarity	NPC474931
0.869	High Similarity	NPC117188
0.869	High Similarity	NPC205421
0.869	High Similarity	NPC158376
0.8683	High Similarity	NPC196447
0.8683	High Similarity	NPC136508
0.8683	High Similarity	NPC306843
0.8683	High Similarity	NPC96603
0.8683	High Similarity	NPC78222
0.8683	High Similarity	NPC253043
0.8683	High Similarity	NPC477563
0.8683	High Similarity	NPC212794
0.8683	High Similarity	NPC24465
0.8683	High Similarity	NPC13504
0.8675	High Similarity	NPC60186
0.8625	High Similarity	NPC476151
0.8625	High Similarity	NPC476144
0.8625	High Similarity	NPC106295
0.8625	High Similarity	NPC16107
0.8625	High Similarity	NPC51957
0.8625	High Similarity	NPC210437
0.8623	High Similarity	NPC324144
0.8613	High Similarity	NPC220961
0.858	High Similarity	NPC88249
0.858	High Similarity	NPC220858
0.858	High Similarity	NPC192768
0.858	High Similarity	NPC151895
0.858	High Similarity	NPC97221
0.8571	High Similarity	NPC7467
0.8571	High Similarity	NPC232514
0.8571	High Similarity	NPC276944
0.8571	High Similarity	NPC169743
0.8571	High Similarity	NPC238530
0.8523	High Similarity	NPC95426
0.8523	High Similarity	NPC302245
0.8523	High Similarity	NPC16357
0.8519	High Similarity	NPC103379
0.8519	High Similarity	NPC477565
0.8512	High Similarity	NPC1229
0.8503	High Similarity	NPC27410
0.8503	High Similarity	NPC166014
0.85	High Similarity	NPC185838
0.8494	Intermediate Similarity	NPC476572
0.8485	Intermediate Similarity	NPC99659
0.8485	Intermediate Similarity	NPC325871
0.8475	Intermediate Similarity	NPC65312
0.8475	Intermediate Similarity	NPC139783
0.8471	Intermediate Similarity	NPC150879
0.8457	Intermediate Similarity	NPC428
0.8457	Intermediate Similarity	NPC476571
0.8457	Intermediate Similarity	NPC24233
0.8457	Intermediate Similarity	NPC147390
0.8457	Intermediate Similarity	NPC246587
0.8457	Intermediate Similarity	NPC135538
0.8448	Intermediate Similarity	NPC114364
0.8448	Intermediate Similarity	NPC320223
0.8439	Intermediate Similarity	NPC229166
0.8439	Intermediate Similarity	NPC128560
0.8439	Intermediate Similarity	NPC199465
0.843	Intermediate Similarity	NPC239775
0.8427	Intermediate Similarity	NPC275680
0.8427	Intermediate Similarity	NPC22115
0.8421	Intermediate Similarity	NPC83198
0.8421	Intermediate Similarity	NPC204908
0.8409	Intermediate Similarity	NPC248642
0.8409	Intermediate Similarity	NPC116284
0.84	Intermediate Similarity	NPC126284
0.8395	Intermediate Similarity	NPC321505
0.8395	Intermediate Similarity	NPC191376
0.8395	Intermediate Similarity	NPC179825
0.8391	Intermediate Similarity	NPC237044
0.8382	Intermediate Similarity	NPC66341
0.8382	Intermediate Similarity	NPC192135
0.8382	Intermediate Similarity	NPC477020
0.838	Intermediate Similarity	NPC206900
0.8375	Intermediate Similarity	NPC128019
0.8375	Intermediate Similarity	NPC136860
0.8375	Intermediate Similarity	NPC476567
0.8373	Intermediate Similarity	NPC138487
0.8373	Intermediate Similarity	NPC216459
0.8373	Intermediate Similarity	NPC41178
0.8372	Intermediate Similarity	NPC477562
0.8372	Intermediate Similarity	NPC118274
0.8372	Intermediate Similarity	NPC168753
0.8372	Intermediate Similarity	NPC26240
0.8372	Intermediate Similarity	NPC69712
0.8363	Intermediate Similarity	NPC298979
0.8362	Intermediate Similarity	NPC156576
0.8353	Intermediate Similarity	NPC134858
0.8343	Intermediate Similarity	NPC474325
0.8343	Intermediate Similarity	NPC118633
0.8343	Intermediate Similarity	NPC148693
0.8343	Intermediate Similarity	NPC294790
0.8333	Intermediate Similarity	NPC111485
0.8333	Intermediate Similarity	NPC304675
0.8324	Intermediate Similarity	NPC237579
0.8323	Intermediate Similarity	NPC146288
0.8314	Intermediate Similarity	NPC470324
0.8305	Intermediate Similarity	NPC279228
0.8305	Intermediate Similarity	NPC222661
0.8305	Intermediate Similarity	NPC328155
0.8305	Intermediate Similarity	NPC182052
0.8305	Intermediate Similarity	NPC42663
0.8305	Intermediate Similarity	NPC311973
0.8305	Intermediate Similarity	NPC290582
0.8305	Intermediate Similarity	NPC258657
0.8305	Intermediate Similarity	NPC223690
0.8305	Intermediate Similarity	NPC217748
0.8305	Intermediate Similarity	NPC185639
0.8305	Intermediate Similarity	NPC54654
0.8305	Intermediate Similarity	NPC181796
0.8305	Intermediate Similarity	NPC290005
0.8305	Intermediate Similarity	NPC285931
0.8305	Intermediate Similarity	NPC8836
0.8305	Intermediate Similarity	NPC229373
0.8305	Intermediate Similarity	NPC15414
0.8305	Intermediate Similarity	NPC239824
0.8305	Intermediate Similarity	NPC251735
0.8305	Intermediate Similarity	NPC7715
0.8305	Intermediate Similarity	NPC104196
0.8305	Intermediate Similarity	NPC271013
0.8305	Intermediate Similarity	NPC49075
0.8305	Intermediate Similarity	NPC90998
0.8304	Intermediate Similarity	NPC476432
0.8304	Intermediate Similarity	NPC124657
0.8304	Intermediate Similarity	NPC24264
0.8303	Intermediate Similarity	NPC326316
0.8303	Intermediate Similarity	NPC476579
0.8303	Intermediate Similarity	NPC81733
0.8295	Intermediate Similarity	NPC474745
0.8294	Intermediate Similarity	NPC233650
0.8286	Intermediate Similarity	NPC474470
0.8284	Intermediate Similarity	NPC230956
0.8284	Intermediate Similarity	NPC205167
0.8284	Intermediate Similarity	NPC249274
0.8284	Intermediate Similarity	NPC271388
0.8284	Intermediate Similarity	NPC205255
0.8284	Intermediate Similarity	NPC119649
0.8284	Intermediate Similarity	NPC235143
0.8276	Intermediate Similarity	NPC152680
0.8276	Intermediate Similarity	NPC232386
0.8276	Intermediate Similarity	NPC190783
0.8263	Intermediate Similarity	NPC244112
0.8258	Intermediate Similarity	NPC254441
0.8258	Intermediate Similarity	NPC274716
0.8258	Intermediate Similarity	NPC167116
0.8256	Intermediate Similarity	NPC474324
0.8256	Intermediate Similarity	NPC57812
0.8256	Intermediate Similarity	NPC247389
0.8256	Intermediate Similarity	NPC210140
0.825	Intermediate Similarity	NPC474915
0.825	Intermediate Similarity	NPC328750
0.825	Intermediate Similarity	NPC213206
0.825	Intermediate Similarity	NPC188163
0.8249	Intermediate Similarity	NPC286119
0.8246	Intermediate Similarity	NPC167546
0.8246	Intermediate Similarity	NPC3375
0.8246	Intermediate Similarity	NPC225774
0.8246	Intermediate Similarity	NPC302527
0.8246	Intermediate Similarity	NPC255607
0.8246	Intermediate Similarity	NPC16805
0.8242	Intermediate Similarity	NPC256124
0.8235	Intermediate Similarity	NPC79402
0.8235	Intermediate Similarity	NPC80759
0.8225	Intermediate Similarity	NPC221864
0.8225	Intermediate Similarity	NPC59028
0.8225	Intermediate Similarity	NPC92191
0.8214	Intermediate Similarity	NPC234392
0.8214	Intermediate Similarity	NPC31311
0.8208	Intermediate Similarity	NPC475845
0.8204	Intermediate Similarity	NPC477564
0.8204	Intermediate Similarity	NPC2295
0.8202	Intermediate Similarity	NPC30779
0.8198	Intermediate Similarity	NPC250846
0.8198	Intermediate Similarity	NPC42549

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 NPC241704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	643
0.2-0.3	922
0.3-0.4	1984
0.4-0.5	2534
0.5-0.6	1828
0.6-0.7	872
0.7-0.8	182
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8625	High Similarity	NPD4584	Approved
0.8314	Intermediate Similarity	NPD2898	Approved
0.8305	Intermediate Similarity	NPD8054	Approved
0.8305	Intermediate Similarity	NPD8053	Approved
0.825	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD4481	Phase 3
0.8204	Intermediate Similarity	NPD4772	Phase 2
0.8204	Intermediate Similarity	NPD4773	Phase 2
0.8171	Intermediate Similarity	NPD8156	Discontinued
0.814	Intermediate Similarity	NPD6107	Approved
0.8114	Intermediate Similarity	NPD8252	Approved
0.8114	Intermediate Similarity	NPD8251	Approved
0.8114	Intermediate Similarity	NPD8099	Discontinued
0.8046	Intermediate Similarity	NPD2970	Approved
0.8046	Intermediate Similarity	NPD2969	Approved
0.8	Intermediate Similarity	NPD2489	Approved
0.8	Intermediate Similarity	NPD27	Approved
0.8	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD3051	Approved
0.7886	Intermediate Similarity	NPD6071	Discontinued
0.7865	Intermediate Similarity	NPD5313	Approved
0.7865	Intermediate Similarity	NPD5312	Approved
0.7857	Intermediate Similarity	NPD3641	Approved
0.7857	Intermediate Similarity	NPD3639	Approved
0.7857	Intermediate Similarity	NPD3640	Phase 3
0.7849	Intermediate Similarity	NPD2560	Approved
0.7849	Intermediate Similarity	NPD2563	Approved
0.7836	Intermediate Similarity	NPD7298	Approved
0.7819	Intermediate Similarity	NPD4420	Approved
0.779	Intermediate Similarity	NPD7549	Discontinued
0.7784	Intermediate Similarity	NPD2421	Approved
0.7784	Intermediate Similarity	NPD2420	Approved
0.7772	Intermediate Similarity	NPD7906	Approved
0.7771	Intermediate Similarity	NPD5241	Discontinued
0.7759	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7831	Phase 2
0.7759	Intermediate Similarity	NPD7833	Phase 2
0.7749	Intermediate Similarity	NPD5006	Approved
0.7749	Intermediate Similarity	NPD5005	Approved
0.7747	Intermediate Similarity	NPD7311	Approved
0.7747	Intermediate Similarity	NPD7310	Approved
0.7747	Intermediate Similarity	NPD7313	Approved
0.7747	Intermediate Similarity	NPD7312	Approved
0.7738	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6666	Approved
0.7725	Intermediate Similarity	NPD6667	Approved
0.7714	Intermediate Similarity	NPD5709	Phase 3
0.7705	Intermediate Similarity	NPD7309	Approved
0.7705	Intermediate Similarity	NPD6851	Approved
0.7705	Intermediate Similarity	NPD6853	Approved
0.7701	Intermediate Similarity	NPD6788	Approved
0.7684	Intermediate Similarity	NPD4010	Discontinued
0.768	Intermediate Similarity	NPD6297	Approved
0.767	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4666	Phase 3
0.7661	Intermediate Similarity	NPD4017	Approved
0.765	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD4578	Approved
0.765	Intermediate Similarity	NPD4577	Approved
0.7647	Intermediate Similarity	NPD6030	Approved
0.7647	Intermediate Similarity	NPD6031	Approved
0.7622	Intermediate Similarity	NPD4663	Approved
0.7596	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD2490	Approved
0.7594	Intermediate Similarity	NPD2488	Approved
0.7572	Intermediate Similarity	NPD6385	Approved
0.7572	Intermediate Similarity	NPD6386	Approved
0.7515	Intermediate Similarity	NPD3845	Phase 1
0.7461	Intermediate Similarity	NPD4107	Approved
0.7459	Intermediate Similarity	NPD2968	Approved
0.7459	Intermediate Similarity	NPD2971	Approved
0.744	Intermediate Similarity	NPD4237	Approved
0.744	Intermediate Similarity	NPD4236	Phase 3
0.744	Intermediate Similarity	NPD3060	Approved
0.744	Intermediate Similarity	NPD5177	Phase 3
0.7423	Intermediate Similarity	NPD3450	Approved
0.7423	Intermediate Similarity	NPD2494	Approved
0.7423	Intermediate Similarity	NPD2493	Approved
0.7423	Intermediate Similarity	NPD3452	Approved
0.7418	Intermediate Similarity	NPD7177	Discontinued
0.7407	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2974	Approved
0.7396	Intermediate Similarity	NPD2975	Approved
0.7396	Intermediate Similarity	NPD2973	Approved
0.7385	Intermediate Similarity	NPD3057	Approved
0.7384	Intermediate Similarity	NPD6090	Discontinued
0.7384	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD42	Phase 2
0.7377	Intermediate Similarity	NPD6042	Phase 2
0.7376	Intermediate Similarity	NPD7047	Phase 3
0.7374	Intermediate Similarity	NPD5677	Discontinued
0.736	Intermediate Similarity	NPD4055	Discovery
0.7353	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7038	Approved
0.7351	Intermediate Similarity	NPD7039	Approved
0.7348	Intermediate Similarity	NPD5242	Approved
0.7345	Intermediate Similarity	NPD5977	Approved
0.7345	Intermediate Similarity	NPD5978	Approved
0.7341	Intermediate Similarity	NPD1914	Approved
0.7341	Intermediate Similarity	NPD7427	Discontinued
0.7333	Intermediate Similarity	NPD4482	Phase 3
0.733	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6997	Phase 2
0.732	Intermediate Similarity	NPD8095	Phase 1
0.7317	Intermediate Similarity	NPD4474	Approved
0.7317	Intermediate Similarity	NPD4475	Approved
0.7316	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4583	Approved
0.731	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4582	Approved
0.7305	Intermediate Similarity	NPD1753	Discontinued
0.7302	Intermediate Similarity	NPD7291	Discontinued
0.7299	Intermediate Similarity	NPD3686	Approved
0.7299	Intermediate Similarity	NPD3687	Approved
0.7296	Intermediate Similarity	NPD3448	Approved
0.7296	Intermediate Similarity	NPD3533	Approved
0.7296	Intermediate Similarity	NPD2972	Approved
0.7296	Intermediate Similarity	NPD2491	Approved
0.7293	Intermediate Similarity	NPD4166	Phase 2
0.7288	Intermediate Similarity	NPD2978	Approved
0.7288	Intermediate Similarity	NPD5772	Approved
0.7288	Intermediate Similarity	NPD5773	Approved
0.7288	Intermediate Similarity	NPD2977	Approved
0.7282	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4580	Approved
0.7273	Intermediate Similarity	NPD7280	Phase 3
0.7273	Intermediate Similarity	NPD7281	Phase 3
0.7267	Intermediate Similarity	NPD3124	Discontinued
0.7264	Intermediate Similarity	NPD5676	Approved
0.7263	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4004	Approved
0.7259	Intermediate Similarity	NPD4002	Approved
0.7256	Intermediate Similarity	NPD5718	Phase 2
0.7251	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2122	Discontinued
0.7239	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6618	Phase 2
0.7234	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4433	Discontinued
0.7225	Intermediate Similarity	NPD4123	Phase 3
0.7225	Intermediate Similarity	NPD1424	Approved
0.7219	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3656	Approved
0.7209	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4210	Discontinued
0.7198	Intermediate Similarity	NPD6747	Phase 1
0.7195	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4585	Approved
0.7186	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD2904	Discontinued
0.7175	Intermediate Similarity	NPD5090	Approved
0.7175	Intermediate Similarity	NPD5089	Approved
0.7175	Intermediate Similarity	NPD6873	Phase 2
0.7174	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2238	Phase 2
0.7168	Intermediate Similarity	NPD7598	Phase 2
0.7165	Intermediate Similarity	NPD5582	Discontinued
0.7159	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4005	Discontinued
0.7158	Intermediate Similarity	NPD2388	Discontinued
0.7143	Intermediate Similarity	NPD5976	Discontinued
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7802	Discontinued
0.7136	Intermediate Similarity	NPD4040	Phase 1
0.7135	Intermediate Similarity	NPD4162	Approved
0.7129	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7400	Phase 3
0.7126	Intermediate Similarity	NPD3536	Discontinued
0.7119	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5844	Phase 1
0.7093	Intermediate Similarity	NPD6748	Discontinued
0.7093	Intermediate Similarity	NPD6331	Phase 2
0.7085	Intermediate Similarity	NPD7497	Discontinued
0.7083	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6072	Discontinued
0.7069	Intermediate Similarity	NPD7213	Phase 3
0.7069	Intermediate Similarity	NPD7212	Phase 2
0.7066	Intermediate Similarity	NPD4060	Phase 1
0.7062	Intermediate Similarity	NPD824	Approved
0.7062	Intermediate Similarity	NPD3455	Phase 2
0.7059	Intermediate Similarity	NPD6032	Approved
0.7059	Intermediate Similarity	NPD4476	Approved
0.7059	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4477	Approved
0.7056	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2677	Approved
0.7052	Intermediate Similarity	NPD3692	Discontinued
0.7041	Intermediate Similarity	NPD6896	Approved
0.7041	Intermediate Similarity	NPD6895	Approved
0.7041	Intermediate Similarity	NPD5564	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