NPASS Compound

Structure

CID109533 OpenBabel06191715462D 26 29 0 0 1 0 0 0 0 0999 V2000 -3.6371 5.1540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3658 3.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8414 2.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5674 5.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7426 3.6846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5235 0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6821 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0470 2.9123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0467 1.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6829 2.9132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8403 1.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5244 3.3987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2073 4.3687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5238 1.4564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2070 3.3982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3653 1.9419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6826 1.9424 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8409 0.4855 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8406 0.4860 0.0000 C 0 0 1 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 -3.3655 2.9128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8412 1.4569 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1724 4.4699 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7068 -0.0138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 7 1 0 0 0 0 7 19 1 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 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 1 1 1 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 6 1 1 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 22 1 6 0 0 0 17 22 1 6 0 0 0 18 23 1 6 0 0 0 19 21 1 0 0 0 0 19 23 1 6 0 0 0 20 21 1 0 0 0 0 20 25 1 6 0 0 0 21 26 1 1 0 0 0 22 2 1 6 0 0 0 23 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	363.31
Volume:	400.715
LogP:	4.278
LogD:	4.483
LogS:	-3.475
# Rotatable Bonds:	2
TPSA:	43.7
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	4.486
Fsp3:	1.0
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:	-4.771
MDCK Permeability:	1.0092965567309875e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.836
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.388
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.322
Plasma Protein Binding (PPB):	66.5351333618164%
Volume Distribution (VD):	1.578
Pgp-substrate:	18.668790817260742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.187
CYP1A2-substrate:	0.377
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.967
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.396
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.658

ADMET: Excretion

Clearance (CL):	16.241
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.366
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.403
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.617
Maximum Recommended Daily Dose:	0.058
Skin Sensitization:	0.944
Carcinogencity:	0.46
Eye Corrosion:	0.993
Eye Irritation:	0.137
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC109533

Natural Product ID:	NPC109533
*Common Name:**	Terminaline
IUPAC Name:	(3S,4S,5R,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol
Synonyms:	terminaline
Standard InCHIKey:	QTNGLMWAVBOBLJ-RCFZRFIHSA-N
Standard InCHI:	InChI=1S/C23H41NO2/c1-14(24(4)5)16-8-9-17-15-6-7-19-21(26)20(25)11-13-23(19,3)18(15)10-12-22(16,17)2/h14-21,25-26H,6-13H2,1-5H3/t14-,15-,16+,17-,18-,19-,20-,21-,22+,23+/m0/s1
SMILES:	O[C@H]1CC[C@]2([C@H]([C@@H]1O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](N(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087212
PubChem CID:	177562
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins and derivatives

*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
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22804108]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18213	Strychnos variabilis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10911	Euphorbia peplis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13128	Crotalaria rosenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2332	Plantago serraria	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9527	Dendrodoa grossularia	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4160	Cephalosporium polyaleurum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11838	Euphorbia regis-jubae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7351	Uncaria pteropoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	360.0	nM	PMID[564096]

☑ 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 NPC109533 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	119
0.1-0.2	2849
0.2-0.3	18671
0.3-0.4	10462
0.4-0.5	5869
0.5-0.6	3718
0.6-0.7	816
0.7-0.8	187
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8068	Intermediate Similarity	NPC312637
0.7949	Intermediate Similarity	NPC231945
0.7857	Intermediate Similarity	NPC192456
0.7821	Intermediate Similarity	NPC107919
0.7821	Intermediate Similarity	NPC470830
0.7821	Intermediate Similarity	NPC241085
0.7821	Intermediate Similarity	NPC299948
0.7742	Intermediate Similarity	NPC140300
0.7733	Intermediate Similarity	NPC114891
0.7684	Intermediate Similarity	NPC475518
0.7662	Intermediate Similarity	NPC142712
0.7654	Intermediate Similarity	NPC228994
0.7654	Intermediate Similarity	NPC192501
0.7654	Intermediate Similarity	NPC10476
0.7634	Intermediate Similarity	NPC289140
0.76	Intermediate Similarity	NPC71460
0.76	Intermediate Similarity	NPC218585
0.76	Intermediate Similarity	NPC148174
0.7564	Intermediate Similarity	NPC63190
0.7564	Intermediate Similarity	NPC48079
0.7564	Intermediate Similarity	NPC475884
0.7564	Intermediate Similarity	NPC473230
0.7561	Intermediate Similarity	NPC196136
0.7561	Intermediate Similarity	NPC158208
0.7561	Intermediate Similarity	NPC243027
0.7553	Intermediate Similarity	NPC473537
0.7553	Intermediate Similarity	NPC292819
0.7532	Intermediate Similarity	NPC474380
0.7532	Intermediate Similarity	NPC473276
0.7532	Intermediate Similarity	NPC41577
0.7531	Intermediate Similarity	NPC473238
0.7531	Intermediate Similarity	NPC472341
0.7531	Intermediate Similarity	NPC470610
0.7531	Intermediate Similarity	NPC153719
0.7528	Intermediate Similarity	NPC21035
0.7527	Intermediate Similarity	NPC174117
0.7474	Intermediate Similarity	NPC475249
0.7474	Intermediate Similarity	NPC252564
0.7474	Intermediate Similarity	NPC220111
0.747	Intermediate Similarity	NPC477602
0.747	Intermediate Similarity	NPC163597
0.747	Intermediate Similarity	NPC473916
0.747	Intermediate Similarity	NPC477601
0.7468	Intermediate Similarity	NPC472741
0.7439	Intermediate Similarity	NPC48795
0.7436	Intermediate Similarity	NPC44122
0.7407	Intermediate Similarity	NPC157777
0.7407	Intermediate Similarity	NPC131506
0.7403	Intermediate Similarity	NPC167995
0.7403	Intermediate Similarity	NPC69149
0.7403	Intermediate Similarity	NPC159654
0.7403	Intermediate Similarity	NPC118937
0.7403	Intermediate Similarity	NPC281540
0.7396	Intermediate Similarity	NPC201712
0.7386	Intermediate Similarity	NPC175419
0.7381	Intermediate Similarity	NPC302578
0.7381	Intermediate Similarity	NPC128951
0.7381	Intermediate Similarity	NPC477227
0.7381	Intermediate Similarity	NPC192046
0.7381	Intermediate Similarity	NPC105208
0.7375	Intermediate Similarity	NPC254037
0.7375	Intermediate Similarity	NPC477820
0.7375	Intermediate Similarity	NPC66407
0.7375	Intermediate Similarity	NPC129829
0.7349	Intermediate Similarity	NPC270306
0.7349	Intermediate Similarity	NPC91387
0.7349	Intermediate Similarity	NPC231680
0.7349	Intermediate Similarity	NPC317242
0.7342	Intermediate Similarity	NPC204233
0.734	Intermediate Similarity	NPC155985
0.7308	Intermediate Similarity	NPC243469
0.7308	Intermediate Similarity	NPC190827
0.7308	Intermediate Similarity	NPC260116
0.7308	Intermediate Similarity	NPC475943
0.7294	Intermediate Similarity	NPC102708
0.7294	Intermediate Similarity	NPC147993
0.7294	Intermediate Similarity	NPC67657
0.7294	Intermediate Similarity	NPC18857
0.7284	Intermediate Similarity	NPC282454
0.7284	Intermediate Similarity	NPC232925
0.7284	Intermediate Similarity	NPC251201
0.7284	Intermediate Similarity	NPC192192
0.7284	Intermediate Similarity	NPC63588
0.7273	Intermediate Similarity	NPC323180
0.7263	Intermediate Similarity	NPC476903
0.7262	Intermediate Similarity	NPC91573
0.7262	Intermediate Similarity	NPC470145
0.725	Intermediate Similarity	NPC475893
0.7222	Intermediate Similarity	NPC171698
0.7222	Intermediate Similarity	NPC270957
0.7222	Intermediate Similarity	NPC321340
0.7222	Intermediate Similarity	NPC119633
0.72	Intermediate Similarity	NPC476735
0.7195	Intermediate Similarity	NPC195530
0.7195	Intermediate Similarity	NPC109457
0.7195	Intermediate Similarity	NPC157422
0.7195	Intermediate Similarity	NPC470071
0.7195	Intermediate Similarity	NPC187471
0.7195	Intermediate Similarity	NPC127094
0.7195	Intermediate Similarity	NPC100586
0.7195	Intermediate Similarity	NPC8004
0.7195	Intermediate Similarity	NPC478103
0.7195	Intermediate Similarity	NPC252182
0.7195	Intermediate Similarity	NPC1340
0.7195	Intermediate Similarity	NPC127283
0.7195	Intermediate Similarity	NPC473279
0.7176	Intermediate Similarity	NPC11907
0.7176	Intermediate Similarity	NPC133596
0.7176	Intermediate Similarity	NPC474574
0.7176	Intermediate Similarity	NPC64081
0.7176	Intermediate Similarity	NPC185915
0.716	Intermediate Similarity	NPC470833
0.716	Intermediate Similarity	NPC124384
0.716	Intermediate Similarity	NPC99264
0.7129	Intermediate Similarity	NPC48127
0.7129	Intermediate Similarity	NPC83047
0.7129	Intermediate Similarity	NPC8009
0.7129	Intermediate Similarity	NPC267217
0.7126	Intermediate Similarity	NPC16449
0.7111	Intermediate Similarity	NPC75810
0.7108	Intermediate Similarity	NPC232112
0.71	Intermediate Similarity	NPC470596
0.7089	Intermediate Similarity	NPC472946
0.7075	Intermediate Similarity	NPC476502
0.7065	Intermediate Similarity	NPC283751
0.7024	Intermediate Similarity	NPC304499
0.7024	Intermediate Similarity	NPC478130
0.7024	Intermediate Similarity	NPC477508
0.7011	Intermediate Similarity	NPC477282
0.7011	Intermediate Similarity	NPC287452
0.7011	Intermediate Similarity	NPC81074
0.7	Intermediate Similarity	NPC241879
0.6988	Remote Similarity	NPC111234
0.6988	Remote Similarity	NPC58057
0.6988	Remote Similarity	NPC151018
0.6988	Remote Similarity	NPC156277
0.6988	Remote Similarity	NPC320549
0.6966	Remote Similarity	NPC154043
0.6966	Remote Similarity	NPC202688
0.6966	Remote Similarity	NPC477599
0.6966	Remote Similarity	NPC121121
0.6966	Remote Similarity	NPC60018
0.6961	Remote Similarity	NPC46981
0.6957	Remote Similarity	NPC320478
0.6951	Remote Similarity	NPC245223
0.6941	Remote Similarity	NPC70982
0.6941	Remote Similarity	NPC104387
0.6941	Remote Similarity	NPC178383
0.6941	Remote Similarity	NPC212733
0.6941	Remote Similarity	NPC185536
0.6941	Remote Similarity	NPC174964
0.6941	Remote Similarity	NPC230704
0.6941	Remote Similarity	NPC3403
0.6941	Remote Similarity	NPC212879
0.6941	Remote Similarity	NPC231256
0.6941	Remote Similarity	NPC273366
0.6941	Remote Similarity	NPC97534
0.6941	Remote Similarity	NPC240235
0.6941	Remote Similarity	NPC195155
0.6939	Remote Similarity	NPC91604
0.6932	Remote Similarity	NPC236112
0.6932	Remote Similarity	NPC13554
0.6931	Remote Similarity	NPC475239
0.6923	Remote Similarity	NPC139778
0.6915	Remote Similarity	NPC159390
0.6915	Remote Similarity	NPC247891
0.6915	Remote Similarity	NPC133995
0.6914	Remote Similarity	NPC475172
0.69	Remote Similarity	NPC50815
0.69	Remote Similarity	NPC471083
0.69	Remote Similarity	NPC476755
0.69	Remote Similarity	NPC470592
0.6893	Remote Similarity	NPC470595
0.6889	Remote Similarity	NPC478054
0.6889	Remote Similarity	NPC211135
0.6889	Remote Similarity	NPC216420
0.6889	Remote Similarity	NPC246956
0.6889	Remote Similarity	NPC207013
0.6889	Remote Similarity	NPC85095
0.6887	Remote Similarity	NPC28224
0.6875	Remote Similarity	NPC80463
0.6867	Remote Similarity	NPC45296
0.6863	Remote Similarity	NPC55462
0.686	Remote Similarity	NPC5767
0.686	Remote Similarity	NPC278091
0.686	Remote Similarity	NPC86305
0.686	Remote Similarity	NPC14112
0.686	Remote Similarity	NPC78067
0.686	Remote Similarity	NPC93662
0.686	Remote Similarity	NPC4209
0.686	Remote Similarity	NPC475742
0.686	Remote Similarity	NPC472486
0.686	Remote Similarity	NPC472487
0.6854	Remote Similarity	NPC474531
0.6854	Remote Similarity	NPC12933
0.6848	Remote Similarity	NPC323958
0.6842	Remote Similarity	NPC135438
0.6837	Remote Similarity	NPC474164
0.6835	Remote Similarity	NPC209686
0.6835	Remote Similarity	NPC249078

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 NPC109533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	1736
0.2-0.3	4920
0.3-0.4	1667
0.4-0.5	504
0.5-0.6	174
0.6-0.7	46
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7821	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7920	Phase 3
0.7553	Intermediate Similarity	NPD7919	Phase 3
0.7474	Intermediate Similarity	NPD8088	Phase 1
0.7222	Intermediate Similarity	NPD8308	Discontinued
0.7073	Intermediate Similarity	NPD4787	Phase 1
0.7041	Intermediate Similarity	NPD8418	Phase 2
0.703	Intermediate Similarity	NPD6920	Discontinued
0.6988	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6700	Approved
0.6893	Remote Similarity	NPD6415	Discontinued
0.686	Remote Similarity	NPD6117	Approved
0.6842	Remote Similarity	NPD6702	Approved
0.6842	Remote Similarity	NPD6703	Approved
0.6829	Remote Similarity	NPD6705	Phase 1
0.6824	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7991	Discontinued
0.6796	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6116	Phase 1
0.6747	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8298	Phase 2
0.6705	Remote Similarity	NPD6115	Approved
0.6705	Remote Similarity	NPD6118	Approved
0.6705	Remote Similarity	NPD6114	Approved
0.6705	Remote Similarity	NPD6697	Approved
0.6556	Remote Similarity	NPD7525	Registered
0.6552	Remote Similarity	NPD3703	Phase 2
0.6471	Remote Similarity	NPD4789	Approved
0.6471	Remote Similarity	NPD4245	Approved
0.6471	Remote Similarity	NPD4244	Approved
0.6429	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5360	Phase 3
0.6374	Remote Similarity	NPD6928	Phase 2
0.6353	Remote Similarity	NPD3698	Phase 2
0.6346	Remote Similarity	NPD7912	Approved
0.6346	Remote Similarity	NPD7986	Approved
0.6346	Remote Similarity	NPD7987	Approved
0.6346	Remote Similarity	NPD7911	Approved
0.6306	Remote Similarity	NPD7754	Approved
0.6306	Remote Similarity	NPD7755	Approved
0.6265	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8174	Phase 2
0.6226	Remote Similarity	NPD8040	Discontinued
0.6211	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7339	Approved
0.618	Remote Similarity	NPD6942	Approved
0.6168	Remote Similarity	NPD7989	Approved
0.6168	Remote Similarity	NPD7990	Approved
0.6154	Remote Similarity	NPD3671	Phase 1
0.6044	Remote Similarity	NPD8144	Approved
0.6044	Remote Similarity	NPD8143	Approved
0.6023	Remote Similarity	NPD4758	Discontinued
0.6023	Remote Similarity	NPD3187	Discontinued
0.5941	Remote Similarity	NPD8171	Discontinued
0.5934	Remote Similarity	NPD6933	Approved
0.5934	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7645	Phase 2
0.5893	Remote Similarity	NPD8077	Approved
0.5893	Remote Similarity	NPD8078	Approved
0.5882	Remote Similarity	NPD5771	Approved
0.5851	Remote Similarity	NPD4748	Discontinued
0.5849	Remote Similarity	NPD4159	Approved
0.5843	Remote Similarity	NPD6081	Approved
0.5814	Remote Similarity	NPD4224	Phase 2
0.5806	Remote Similarity	NPD5364	Discontinued
0.58	Remote Similarity	NPD5328	Approved
0.5773	Remote Similarity	NPD4786	Approved
0.5765	Remote Similarity	NPD371	Approved
0.5745	Remote Similarity	NPD7155	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6940	Discontinued
0.5733	Remote Similarity	NPD384	Approved
0.5733	Remote Similarity	NPD385	Approved
0.5714	Remote Similarity	NPD6926	Approved
0.5714	Remote Similarity	NPD6924	Approved
0.5686	Remote Similarity	NPD6079	Approved
0.5686	Remote Similarity	NPD8034	Phase 2
0.5686	Remote Similarity	NPD8035	Phase 2
0.567	Remote Similarity	NPD4788	Approved
0.5667	Remote Similarity	NPD5777	Approved
0.5657	Remote Similarity	NPD3618	Phase 1
0.5652	Remote Similarity	NPD3702	Approved
0.5636	Remote Similarity	NPD7333	Discontinued
0.5619	Remote Similarity	NPD5349	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