NPASS Compound

Structure

CID103527 OpenBabel06191715452D 24 25 0 0 1 0 0 0 0 0999 V2000 -2.5981 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 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 1.0000 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 -2.5981 4.5000 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 1.7321 0.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 1.8660 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 1 7 1 0 0 0 0 2 13 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 6 19 1 0 0 0 0 7 13 2 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 21 2 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 19 1 1 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 18 5 1 6 0 0 0 18 23 1 0 0 0 0 19 20 1 6 0 0 0 20 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	367.251
LogP:	2.06
LogD:	1.993
LogS:	-3.73
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	4.795
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.598
MDCK Permeability:	2.2414482373278588e-05
Pgp-inhibitor:	0.434
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.315
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.484
Plasma Protein Binding (PPB):	77.98995208740234%
Volume Distribution (VD):	0.742
Pgp-substrate:	28.676897048950195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.6
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	6.141
Half-life (T1/2):	0.661

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.315
Skin Sensitization:	0.472
Carcinogencity:	0.842
Eye Corrosion:	0.019
Eye Irritation:	0.067
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC103527

Natural Product ID:	NPC103527
*Common Name:**	WPMWSYYVAMDDNR-URNWNBMOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WPMWSYYVAMDDNR-URNWNBMOSA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-7-13(2)14(21)12-15-18(5,23)10-11-20(24)17(3,4)9-8-16(22)19(15,20)6/h7,15-16,22-24H,8-12H2,1-6H3/b13-7+/t15-,16-,18+,19-,20+/m0/s1
SMILES:	C/C=C(C)/C(=O)C[C@H]1[C@@](C)(CC[C@]2(C(C)(C)CC[C@@H]([C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3600945
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0003131] Alpha,beta-unsaturated carbonyl compounds [CHEMONTID:0003672] Alpha,beta-unsaturated ketones [CHEMONTID:0003674] Alpha-branched alpha,beta-unsaturated ketones

*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
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(98)00208-8]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[22122667]
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22122667]
NPO40342	Scapania irrigua	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26252628]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26575	Scapania undulata	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO937	Limnodynastes terraereginae	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26818	Euphorbia kaleniczenkii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26178	Guarea glabra	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26390	Triphasia trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26519	Acanthodoris nanaimoensis	Species	Onchidorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26872	Piper betle	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25939	Lupinus macounii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26360	Methysticodendron amesianum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4408	Alstonia rostrata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25961	Liatris graminifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10837	Matthiola incana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26275	Dactynotus rudbeckiae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7055	Lychnophora hakeaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26575	Scapania undulata	Species	Scapaniaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[542953]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[542953]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[542953]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[542953]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[542953]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	10000.0	nM	PMID[542953]

☑ 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 NPC103527 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	200
0.1-0.2	1353
0.2-0.3	4733
0.3-0.4	8595
0.4-0.5	13076
0.5-0.6	7101
0.6-0.7	5393
0.7-0.8	2137
0.8-0.85	94
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC251170
0.8913	High Similarity	NPC258674
0.8791	High Similarity	NPC128672
0.8791	High Similarity	NPC134321
0.8723	High Similarity	NPC61369
0.8723	High Similarity	NPC469545
0.8723	High Similarity	NPC5532
0.8696	High Similarity	NPC472978
0.8636	High Similarity	NPC64600
0.8511	High Similarity	NPC471207
0.8511	High Similarity	NPC196227
0.8478	Intermediate Similarity	NPC472973
0.8438	Intermediate Similarity	NPC273269
0.8421	Intermediate Similarity	NPC473170
0.8421	Intermediate Similarity	NPC476245
0.8421	Intermediate Similarity	NPC272617
0.8421	Intermediate Similarity	NPC266899
0.8317	Intermediate Similarity	NPC83744
0.8317	Intermediate Similarity	NPC477916
0.8316	Intermediate Similarity	NPC472977
0.8316	Intermediate Similarity	NPC111015
0.8316	Intermediate Similarity	NPC472976
0.8298	Intermediate Similarity	NPC472975
0.8298	Intermediate Similarity	NPC116726
0.8298	Intermediate Similarity	NPC131872
0.8283	Intermediate Similarity	NPC162973
0.8283	Intermediate Similarity	NPC476081
0.828	Intermediate Similarity	NPC472983
0.8265	Intermediate Similarity	NPC154072
0.8265	Intermediate Similarity	NPC144956
0.8261	Intermediate Similarity	NPC153604
0.8247	Intermediate Similarity	NPC18509
0.8247	Intermediate Similarity	NPC272451
0.8235	Intermediate Similarity	NPC217201
0.8235	Intermediate Similarity	NPC65941
0.8235	Intermediate Similarity	NPC329417
0.8229	Intermediate Similarity	NPC84018
0.8229	Intermediate Similarity	NPC138245
0.8229	Intermediate Similarity	NPC231060
0.8229	Intermediate Similarity	NPC180950
0.8229	Intermediate Similarity	NPC316215
0.8229	Intermediate Similarity	NPC271195
0.8229	Intermediate Similarity	NPC139570
0.8218	Intermediate Similarity	NPC48733
0.8218	Intermediate Similarity	NPC202167
0.8218	Intermediate Similarity	NPC319077
0.8218	Intermediate Similarity	NPC296945
0.8218	Intermediate Similarity	NPC97202
0.8218	Intermediate Similarity	NPC49958
0.8218	Intermediate Similarity	NPC214264
0.8218	Intermediate Similarity	NPC302607
0.8218	Intermediate Similarity	NPC150531
0.8218	Intermediate Similarity	NPC50692
0.8218	Intermediate Similarity	NPC260268
0.8218	Intermediate Similarity	NPC476027
0.8218	Intermediate Similarity	NPC152695
0.8218	Intermediate Similarity	NPC85829
0.8218	Intermediate Similarity	NPC171137
0.8202	Intermediate Similarity	NPC473217
0.82	Intermediate Similarity	NPC282233
0.82	Intermediate Similarity	NPC312900
0.82	Intermediate Similarity	NPC478057
0.82	Intermediate Similarity	NPC249187
0.82	Intermediate Similarity	NPC95585
0.82	Intermediate Similarity	NPC247957
0.819	Intermediate Similarity	NPC73300
0.819	Intermediate Similarity	NPC108721
0.8182	Intermediate Similarity	NPC471412
0.8182	Intermediate Similarity	NPC118964
0.8172	Intermediate Similarity	NPC474925
0.8172	Intermediate Similarity	NPC292491
0.8172	Intermediate Similarity	NPC158778
0.8172	Intermediate Similarity	NPC193360
0.8172	Intermediate Similarity	NPC328539
0.8172	Intermediate Similarity	NPC310752
0.8172	Intermediate Similarity	NPC472802
0.8172	Intermediate Similarity	NPC104560
0.8163	Intermediate Similarity	NPC20479
0.8163	Intermediate Similarity	NPC114274
0.8163	Intermediate Similarity	NPC38471
0.8163	Intermediate Similarity	NPC162459
0.8163	Intermediate Similarity	NPC98837
0.8163	Intermediate Similarity	NPC28864
0.8163	Intermediate Similarity	NPC38296
0.8163	Intermediate Similarity	NPC191565
0.8155	Intermediate Similarity	NPC11710
0.8152	Intermediate Similarity	NPC472986
0.8152	Intermediate Similarity	NPC179591
0.8152	Intermediate Similarity	NPC472985
0.8144	Intermediate Similarity	NPC49371
0.8144	Intermediate Similarity	NPC91439
0.8144	Intermediate Similarity	NPC473158
0.8144	Intermediate Similarity	NPC476327
0.8144	Intermediate Similarity	NPC476318
0.8137	Intermediate Similarity	NPC475060
0.8137	Intermediate Similarity	NPC220229
0.8132	Intermediate Similarity	NPC470812
0.8125	Intermediate Similarity	NPC245972
0.8125	Intermediate Similarity	NPC261333
0.8125	Intermediate Similarity	NPC292374
0.8125	Intermediate Similarity	NPC215271
0.8125	Intermediate Similarity	NPC293086
0.8125	Intermediate Similarity	NPC29247
0.8125	Intermediate Similarity	NPC299100
0.8125	Intermediate Similarity	NPC196485
0.8125	Intermediate Similarity	NPC129004
0.8125	Intermediate Similarity	NPC101233
0.8125	Intermediate Similarity	NPC289539
0.8125	Intermediate Similarity	NPC191094
0.8125	Intermediate Similarity	NPC104371
0.8125	Intermediate Similarity	NPC209662
0.8125	Intermediate Similarity	NPC153775
0.8125	Intermediate Similarity	NPC302008
0.8125	Intermediate Similarity	NPC111524
0.8125	Intermediate Similarity	NPC91772
0.8119	Intermediate Similarity	NPC474281
0.8119	Intermediate Similarity	NPC209502
0.8119	Intermediate Similarity	NPC72255
0.8119	Intermediate Similarity	NPC204833
0.8105	Intermediate Similarity	NPC185936
0.8105	Intermediate Similarity	NPC99380
0.8105	Intermediate Similarity	NPC168027
0.8085	Intermediate Similarity	NPC31985
0.8085	Intermediate Similarity	NPC86319
0.8085	Intermediate Similarity	NPC186688
0.8085	Intermediate Similarity	NPC1015
0.8085	Intermediate Similarity	NPC119416
0.8085	Intermediate Similarity	NPC275740
0.8081	Intermediate Similarity	NPC293866
0.8081	Intermediate Similarity	NPC474720
0.8081	Intermediate Similarity	NPC46761
0.8081	Intermediate Similarity	NPC127408
0.8081	Intermediate Similarity	NPC471727
0.8081	Intermediate Similarity	NPC291785
0.8081	Intermediate Similarity	NPC471413
0.8081	Intermediate Similarity	NPC470074
0.8065	Intermediate Similarity	NPC298904
0.8065	Intermediate Similarity	NPC174619
0.8065	Intermediate Similarity	NPC141292
0.8061	Intermediate Similarity	NPC111187
0.8061	Intermediate Similarity	NPC108078
0.8061	Intermediate Similarity	NPC190080
0.8061	Intermediate Similarity	NPC472851
0.8061	Intermediate Similarity	NPC190554
0.8061	Intermediate Similarity	NPC10864
0.8058	Intermediate Similarity	NPC102843
0.8046	Intermediate Similarity	NPC1973
0.8046	Intermediate Similarity	NPC167873
0.8043	Intermediate Similarity	NPC470574
0.8041	Intermediate Similarity	NPC41070
0.8041	Intermediate Similarity	NPC98639
0.8041	Intermediate Similarity	NPC473240
0.8039	Intermediate Similarity	NPC149047
0.8039	Intermediate Similarity	NPC34768
0.8039	Intermediate Similarity	NPC257353
0.8039	Intermediate Similarity	NPC128828
0.8021	Intermediate Similarity	NPC477435
0.8021	Intermediate Similarity	NPC144739
0.8021	Intermediate Similarity	NPC475255
0.8021	Intermediate Similarity	NPC59170
0.8021	Intermediate Similarity	NPC181594
0.8021	Intermediate Similarity	NPC477436
0.8021	Intermediate Similarity	NPC118490
0.8021	Intermediate Similarity	NPC474807
0.802	Intermediate Similarity	NPC120321
0.802	Intermediate Similarity	NPC191892
0.8	Intermediate Similarity	NPC46848
0.8	Intermediate Similarity	NPC470184
0.8	Intermediate Similarity	NPC256247
0.8	Intermediate Similarity	NPC171888
0.8	Intermediate Similarity	NPC126993
0.8	Intermediate Similarity	NPC85173
0.8	Intermediate Similarity	NPC146945
0.8	Intermediate Similarity	NPC80401
0.8	Intermediate Similarity	NPC46758
0.8	Intermediate Similarity	NPC473099
0.7981	Intermediate Similarity	NPC163004
0.7981	Intermediate Similarity	NPC310546
0.798	Intermediate Similarity	NPC89099
0.798	Intermediate Similarity	NPC103051
0.7979	Intermediate Similarity	NPC131470
0.7979	Intermediate Similarity	NPC474677
0.7979	Intermediate Similarity	NPC206060
0.7979	Intermediate Similarity	NPC473229
0.7979	Intermediate Similarity	NPC143767
0.7961	Intermediate Similarity	NPC67321
0.7961	Intermediate Similarity	NPC187435
0.7959	Intermediate Similarity	NPC200054
0.7959	Intermediate Similarity	NPC264979
0.7959	Intermediate Similarity	NPC249954
0.7959	Intermediate Similarity	NPC472806
0.7959	Intermediate Similarity	NPC29410
0.7959	Intermediate Similarity	NPC192428
0.7959	Intermediate Similarity	NPC135548
0.7959	Intermediate Similarity	NPC167193
0.7957	Intermediate Similarity	NPC213412
0.7957	Intermediate Similarity	NPC73038
0.7957	Intermediate Similarity	NPC475862
0.7957	Intermediate Similarity	NPC94666
0.7957	Intermediate Similarity	NPC74363

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 NPC103527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1762
0.2-0.3	3878
0.3-0.4	2204
0.4-0.5	674
0.5-0.6	189
0.6-0.7	152
0.7-0.8	95
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8298	Intermediate Similarity	NPD6079	Approved
0.828	Intermediate Similarity	NPD5328	Approved
0.8265	Intermediate Similarity	NPD4696	Approved
0.8265	Intermediate Similarity	NPD5286	Approved
0.8265	Intermediate Similarity	NPD5285	Approved
0.8247	Intermediate Similarity	NPD4755	Approved
0.8152	Intermediate Similarity	NPD3618	Phase 1
0.81	Intermediate Similarity	NPD4633	Approved
0.81	Intermediate Similarity	NPD5225	Approved
0.81	Intermediate Similarity	NPD5224	Approved
0.81	Intermediate Similarity	NPD5226	Approved
0.81	Intermediate Similarity	NPD5211	Phase 2
0.8081	Intermediate Similarity	NPD4700	Approved
0.802	Intermediate Similarity	NPD5175	Approved
0.802	Intermediate Similarity	NPD5174	Approved
0.8	Intermediate Similarity	NPD5223	Approved
0.7959	Intermediate Similarity	NPD4697	Phase 3
0.7959	Intermediate Similarity	NPD5221	Approved
0.7959	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5222	Approved
0.7941	Intermediate Similarity	NPD5141	Approved
0.7917	Intermediate Similarity	NPD7515	Phase 2
0.7905	Intermediate Similarity	NPD4634	Approved
0.7885	Intermediate Similarity	NPD6899	Approved
0.7885	Intermediate Similarity	NPD6881	Approved
0.7879	Intermediate Similarity	NPD5173	Approved
0.7864	Intermediate Similarity	NPD6675	Approved
0.7864	Intermediate Similarity	NPD6402	Approved
0.7864	Intermediate Similarity	NPD7128	Approved
0.7864	Intermediate Similarity	NPD5739	Approved
0.7835	Intermediate Similarity	NPD4202	Approved
0.783	Intermediate Similarity	NPD6650	Approved
0.783	Intermediate Similarity	NPD6649	Approved
0.781	Intermediate Similarity	NPD6373	Approved
0.781	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD5697	Approved
0.7736	Intermediate Similarity	NPD7102	Approved
0.7736	Intermediate Similarity	NPD6883	Approved
0.7736	Intermediate Similarity	NPD7290	Approved
0.7714	Intermediate Similarity	NPD4730	Approved
0.7714	Intermediate Similarity	NPD4729	Approved
0.7714	Intermediate Similarity	NPD5128	Approved
0.7714	Intermediate Similarity	NPD7320	Approved
0.77	Intermediate Similarity	NPD7902	Approved
0.7692	Intermediate Similarity	NPD4768	Approved
0.7692	Intermediate Similarity	NPD4767	Approved
0.767	Intermediate Similarity	NPD4754	Approved
0.7664	Intermediate Similarity	NPD6847	Approved
0.7664	Intermediate Similarity	NPD6617	Approved
0.7664	Intermediate Similarity	NPD8130	Phase 1
0.7664	Intermediate Similarity	NPD6869	Approved
0.7642	Intermediate Similarity	NPD6012	Approved
0.7642	Intermediate Similarity	NPD6014	Approved
0.7642	Intermediate Similarity	NPD6013	Approved
0.7619	Intermediate Similarity	NPD5701	Approved
0.7593	Intermediate Similarity	NPD6882	Approved
0.7593	Intermediate Similarity	NPD8297	Approved
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7748	Approved
0.757	Intermediate Similarity	NPD5251	Approved
0.757	Intermediate Similarity	NPD5250	Approved
0.757	Intermediate Similarity	NPD5247	Approved
0.757	Intermediate Similarity	NPD5248	Approved
0.757	Intermediate Similarity	NPD5249	Phase 3
0.7553	Intermediate Similarity	NPD4786	Approved
0.7553	Intermediate Similarity	NPD3665	Phase 1
0.7553	Intermediate Similarity	NPD3666	Approved
0.7553	Intermediate Similarity	NPD3133	Approved
0.7547	Intermediate Similarity	NPD6011	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7526	Intermediate Similarity	NPD4753	Phase 2
0.7523	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD5217	Approved
0.75	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.7434	Intermediate Similarity	NPD6054	Approved
0.7407	Intermediate Similarity	NPD5135	Approved
0.7407	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5169	Approved
0.74	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7900	Approved
0.7383	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6008	Approved
0.7339	Intermediate Similarity	NPD5127	Approved
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6009	Approved
0.732	Intermediate Similarity	NPD3573	Approved
0.7312	Intermediate Similarity	NPD7525	Registered
0.7312	Intermediate Similarity	NPD4695	Discontinued
0.7304	Intermediate Similarity	NPD6370	Approved
0.73	Intermediate Similarity	NPD6399	Phase 3
0.7282	Intermediate Similarity	NPD7638	Approved
0.7281	Intermediate Similarity	NPD6319	Approved
0.7281	Intermediate Similarity	NPD6059	Approved
0.7232	Intermediate Similarity	NPD6274	Approved
0.7222	Intermediate Similarity	NPD5168	Approved
0.7217	Intermediate Similarity	NPD6016	Approved
0.7217	Intermediate Similarity	NPD6015	Approved
0.7212	Intermediate Similarity	NPD7639	Approved
0.7212	Intermediate Similarity	NPD7640	Approved
0.7193	Intermediate Similarity	NPD7101	Approved
0.7193	Intermediate Similarity	NPD7100	Approved
0.7184	Intermediate Similarity	NPD6083	Phase 2
0.7184	Intermediate Similarity	NPD6084	Phase 2
0.7179	Intermediate Similarity	NPD7492	Approved
0.7158	Intermediate Similarity	NPD4221	Approved
0.7158	Intermediate Similarity	NPD4223	Phase 3
0.7156	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD5167	Approved
0.713	Intermediate Similarity	NPD6412	Phase 2
0.7119	Intermediate Similarity	NPD6616	Approved
0.7113	Intermediate Similarity	NPD5329	Approved
0.7105	Intermediate Similarity	NPD6335	Approved
0.7094	Intermediate Similarity	NPD8328	Phase 3
0.7094	Intermediate Similarity	NPD7604	Phase 2
0.7091	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4788	Approved
0.7069	Intermediate Similarity	NPD5983	Phase 2
0.7059	Intermediate Similarity	NPD7078	Approved
0.7041	Intermediate Similarity	NPD5279	Phase 3
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7018	Intermediate Similarity	NPD6317	Approved
0.7018	Intermediate Similarity	NPD7115	Discovery
0.701	Intermediate Similarity	NPD3668	Phase 3
0.701	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD7736	Approved
0.6975	Remote Similarity	NPD6336	Discontinued
0.6957	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD3703	Phase 2
0.6957	Remote Similarity	NPD6314	Approved
0.6952	Remote Similarity	NPD4225	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6939	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6908	Approved
0.6923	Remote Similarity	NPD6909	Approved
0.6917	Remote Similarity	NPD8293	Discontinued
0.6909	Remote Similarity	NPD6686	Approved
0.6893	Remote Similarity	NPD5282	Discontinued
0.6869	Remote Similarity	NPD4623	Approved
0.6869	Remote Similarity	NPD7146	Approved
0.6869	Remote Similarity	NPD6684	Approved
0.6869	Remote Similarity	NPD4690	Approved
0.6869	Remote Similarity	NPD4519	Discontinued
0.6869	Remote Similarity	NPD4693	Phase 3
0.6869	Remote Similarity	NPD7334	Approved
0.6869	Remote Similarity	NPD4138	Approved
0.6869	Remote Similarity	NPD6409	Approved
0.6869	Remote Similarity	NPD5330	Approved
0.6869	Remote Similarity	NPD7521	Approved
0.6869	Remote Similarity	NPD5690	Phase 2
0.6869	Remote Similarity	NPD4689	Approved
0.6869	Remote Similarity	NPD5205	Approved
0.6869	Remote Similarity	NPD4688	Approved
0.6863	Remote Similarity	NPD6411	Approved
0.6863	Remote Similarity	NPD8034	Phase 2
0.6863	Remote Similarity	NPD5281	Approved
0.6863	Remote Similarity	NPD5284	Approved
0.6863	Remote Similarity	NPD8035	Phase 2
0.6847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7507	Approved
0.6827	Remote Similarity	NPD5695	Phase 3
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7331	Phase 2
0.6818	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7319	Approved
0.6796	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD5778	Approved
0.6771	Remote Similarity	NPD6931	Approved
0.6771	Remote Similarity	NPD6930	Phase 2
0.6771	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3617	Approved
0.6735	Remote Similarity	NPD6695	Phase 3
0.6733	Remote Similarity	NPD5737	Approved
0.6733	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6903	Approved
0.6733	Remote Similarity	NPD6672	Approved
0.6721	Remote Similarity	NPD6033	Approved
0.6705	Remote Similarity	NPD7341	Phase 2
0.67	Remote Similarity	NPD5280	Approved
0.67	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6639	Remote Similarity	NPD6921	Approved
0.6633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6932	Approved
0.661	Remote Similarity	NPD4522	Approved
0.6606	Remote Similarity	NPD7632	Discontinued
0.6604	Remote Similarity	NPD7614	Phase 1
0.66	Remote Similarity	NPD1696	Phase 3

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