NPASS Compound

Structure

CID293803 OpenBabel06191716102D 31 35 0 0 1 0 0 0 0 0999 V2000 5.7003 0.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1706 0.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4389 1.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9480 0.5688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4598 -2.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0242 1.9073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8680 -1.4481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6391 0.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8193 1.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0977 -1.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6382 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6396 2.8380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2793 -1.8914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8201 2.3655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8190 -0.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6399 -1.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8201 -1.4189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7661 0.1970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0975 -0.4721 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6394 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6385 0.9460 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9465 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4586 2.3645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4592 -0.4725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4580 1.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4595 -1.4184 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8195 1.4195 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8198 -0.4730 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 -3.3083 2.8545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 29 1 1 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 2 0 0 0 0 25 27 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.35
Volume:	485.535
LogP:	6.668
LogD:	5.665
LogS:	-6.569
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	4.814
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.165
MDCK Permeability:	1.8253867892781273e-05
Pgp-inhibitor:	0.54
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	96.97722625732422%
Volume Distribution (VD):	1.238
Pgp-substrate:	2.345863103866577%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.773
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.966
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.622
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.853
CYP3A4-substrate:	0.857

ADMET: Excretion

Clearance (CL):	3.281
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.338
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.949
Carcinogencity:	0.013
Eye Corrosion:	0.97
Eye Irritation:	0.844
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC293803

Natural Product ID:	NPC293803
*Common Name:**	Glochidone
IUPAC Name:	(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aS,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms:	Glochidone
Standard InCHIKey:	FWBYBHVDDGVPDF-IAFKSKRFSA-N
Standard InCHI:	InChI=1S/C30H46O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h13,15,20-23,25H,1,9-12,14,16-18H2,2-8H3/t20-,21-,22-,23+,25+,27+,28-,29+,30+/m0/s1
SMILES:	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)C=CC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469628
PubChem CID:	44559199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713421]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738378]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[19122328]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark	Urubamba, Cusco, Peru	n.a.	PMID[25927586]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30106289]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15526	Glochidion zeylanicum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15526	Glochidion zeylanicum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15526	Glochidion zeylanicum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1333	Maytenus chiapensis	Species	Celastraceae	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	3
Others	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[532744]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[532744]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	10.0	ug.mL-1	PMID[532744]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[532745]

☑ 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 NPC293803 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	222
0.1-0.2	2143
0.2-0.3	11879
0.3-0.4	13110
0.4-0.5	7282
0.5-0.6	5459
0.6-0.7	2160
0.7-0.8	360
0.8-0.85	42
0.85-0.9	22
0.9-0.95	17
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.971	High Similarity	NPC251705
0.9565	High Similarity	NPC234707
0.9565	High Similarity	NPC115023
0.9429	High Similarity	NPC474228
0.9429	High Similarity	NPC470044
0.9429	High Similarity	NPC303613
0.9429	High Similarity	NPC470045
0.942	High Similarity	NPC282593
0.942	High Similarity	NPC159577
0.942	High Similarity	NPC35734
0.9324	High Similarity	NPC474509
0.9306	High Similarity	NPC69408
0.9296	High Similarity	NPC309852
0.9286	High Similarity	NPC54123
0.9286	High Similarity	NPC305501
0.9275	High Similarity	NPC182815
0.9167	High Similarity	NPC255650
0.9143	High Similarity	NPC2634
0.9143	High Similarity	NPC265782
0.9143	High Similarity	NPC307176
0.9143	High Similarity	NPC251929
0.913	High Similarity	NPC20610
0.9028	High Similarity	NPC255021
0.9014	High Similarity	NPC225467
0.9014	High Similarity	NPC470078
0.9	High Similarity	NPC139397
0.8986	High Similarity	NPC176107
0.8873	High Similarity	NPC477856
0.8873	High Similarity	NPC214770
0.8873	High Similarity	NPC260040
0.8873	High Similarity	NPC40574
0.8841	High Similarity	NPC92327
0.8841	High Similarity	NPC323005
0.8767	High Similarity	NPC329866
0.8767	High Similarity	NPC474796
0.8767	High Similarity	NPC474797
0.875	High Similarity	NPC190035
0.8649	High Similarity	NPC473171
0.8592	High Similarity	NPC296697
0.8592	High Similarity	NPC142754
0.8592	High Similarity	NPC82477
0.8592	High Similarity	NPC188292
0.8592	High Similarity	NPC39157
0.8592	High Similarity	NPC260474
0.8571	High Similarity	NPC43300
0.8551	High Similarity	NPC469662
0.8519	High Similarity	NPC93778
0.8493	Intermediate Similarity	NPC5701
0.8472	Intermediate Similarity	NPC477857
0.8472	Intermediate Similarity	NPC256846
0.8472	Intermediate Similarity	NPC286814
0.8451	Intermediate Similarity	NPC220210
0.8451	Intermediate Similarity	NPC20181
0.8442	Intermediate Similarity	NPC90965
0.8442	Intermediate Similarity	NPC170793
0.8421	Intermediate Similarity	NPC91665
0.8406	Intermediate Similarity	NPC202118
0.8406	Intermediate Similarity	NPC165695
0.8406	Intermediate Similarity	NPC197238
0.8354	Intermediate Similarity	NPC472239
0.8333	Intermediate Similarity	NPC87141
0.8333	Intermediate Similarity	NPC310992
0.8312	Intermediate Similarity	NPC82635
0.8312	Intermediate Similarity	NPC470052
0.8312	Intermediate Similarity	NPC115515
0.831	Intermediate Similarity	NPC96812
0.831	Intermediate Similarity	NPC189917
0.831	Intermediate Similarity	NPC168824
0.831	Intermediate Similarity	NPC107704
0.831	Intermediate Similarity	NPC39462
0.831	Intermediate Similarity	NPC176171
0.8289	Intermediate Similarity	NPC469796
0.8289	Intermediate Similarity	NPC474463
0.8289	Intermediate Similarity	NPC469793
0.8286	Intermediate Similarity	NPC212210
0.8272	Intermediate Similarity	NPC29447
0.8267	Intermediate Similarity	NPC211641
0.8267	Intermediate Similarity	NPC159497
0.8261	Intermediate Similarity	NPC213152
0.8243	Intermediate Similarity	NPC181204
0.8243	Intermediate Similarity	NPC223187
0.8182	Intermediate Similarity	NPC470557
0.8169	Intermediate Similarity	NPC251118
0.8148	Intermediate Similarity	NPC16287
0.8148	Intermediate Similarity	NPC178025
0.8148	Intermediate Similarity	NPC181743
0.8133	Intermediate Similarity	NPC474488
0.8125	Intermediate Similarity	NPC320514
0.8125	Intermediate Similarity	NPC472867
0.8125	Intermediate Similarity	NPC3511
0.8125	Intermediate Similarity	NPC142253
0.8125	Intermediate Similarity	NPC100297
0.8118	Intermediate Similarity	NPC272746
0.8116	Intermediate Similarity	NPC25853
0.8116	Intermediate Similarity	NPC127582
0.8077	Intermediate Similarity	NPC469996
0.8072	Intermediate Similarity	NPC476293
0.8049	Intermediate Similarity	NPC60350
0.8028	Intermediate Similarity	NPC475124
0.8028	Intermediate Similarity	NPC285371
0.8026	Intermediate Similarity	NPC128346
0.8026	Intermediate Similarity	NPC219232
0.7975	Intermediate Similarity	NPC215843
0.7975	Intermediate Similarity	NPC190211
0.7971	Intermediate Similarity	NPC276764
0.7971	Intermediate Similarity	NPC472304
0.7945	Intermediate Similarity	NPC475523
0.7927	Intermediate Similarity	NPC87552
0.7927	Intermediate Similarity	NPC214043
0.7927	Intermediate Similarity	NPC85774
0.7907	Intermediate Similarity	NPC218301
0.7901	Intermediate Similarity	NPC469804
0.7901	Intermediate Similarity	NPC193347
0.7901	Intermediate Similarity	NPC469805
0.7887	Intermediate Similarity	NPC472306
0.7887	Intermediate Similarity	NPC288253
0.7882	Intermediate Similarity	NPC262043
0.7875	Intermediate Similarity	NPC472478
0.7857	Intermediate Similarity	NPC58063
0.7848	Intermediate Similarity	NPC105197
0.7848	Intermediate Similarity	NPC228911
0.7838	Intermediate Similarity	NPC155198
0.7831	Intermediate Similarity	NPC8571
0.7831	Intermediate Similarity	NPC469948
0.7831	Intermediate Similarity	NPC474537
0.7826	Intermediate Similarity	NPC56905
0.7826	Intermediate Similarity	NPC94991
0.7826	Intermediate Similarity	NPC266295
0.7826	Intermediate Similarity	NPC30215
0.7826	Intermediate Similarity	NPC60772
0.7826	Intermediate Similarity	NPC27610
0.7821	Intermediate Similarity	NPC1254
0.7805	Intermediate Similarity	NPC41539
0.7805	Intermediate Similarity	NPC474976
0.7805	Intermediate Similarity	NPC279639
0.7805	Intermediate Similarity	NPC3856
0.7805	Intermediate Similarity	NPC474790
0.7791	Intermediate Similarity	NPC85173
0.7778	Intermediate Similarity	NPC147066
0.7778	Intermediate Similarity	NPC471898
0.7778	Intermediate Similarity	NPC477372
0.7746	Intermediate Similarity	NPC60565
0.7738	Intermediate Similarity	NPC475022
0.7738	Intermediate Similarity	NPC31564
0.7738	Intermediate Similarity	NPC474732
0.7738	Intermediate Similarity	NPC474778
0.7738	Intermediate Similarity	NPC222613
0.7738	Intermediate Similarity	NPC474733
0.7738	Intermediate Similarity	NPC118648
0.7738	Intermediate Similarity	NPC145879
0.7714	Intermediate Similarity	NPC259261
0.7711	Intermediate Similarity	NPC144258
0.7711	Intermediate Similarity	NPC237712
0.7711	Intermediate Similarity	NPC473246
0.7692	Intermediate Similarity	NPC476346
0.7683	Intermediate Similarity	NPC321289
0.7683	Intermediate Similarity	NPC469806
0.7683	Intermediate Similarity	NPC469799
0.7683	Intermediate Similarity	NPC327969
0.7681	Intermediate Similarity	NPC230823
0.7681	Intermediate Similarity	NPC115385
0.7681	Intermediate Similarity	NPC55004
0.7681	Intermediate Similarity	NPC267626
0.7681	Intermediate Similarity	NPC49575
0.7674	Intermediate Similarity	NPC249312
0.7654	Intermediate Similarity	NPC287063
0.7654	Intermediate Similarity	NPC469797
0.7654	Intermediate Similarity	NPC476809
0.7654	Intermediate Similarity	NPC469798
0.7647	Intermediate Similarity	NPC163016
0.7647	Intermediate Similarity	NPC75315
0.7647	Intermediate Similarity	NPC475740
0.7647	Intermediate Similarity	NPC136948
0.7639	Intermediate Similarity	NPC32285
0.7619	Intermediate Similarity	NPC137493
0.7619	Intermediate Similarity	NPC472931
0.7619	Intermediate Similarity	NPC469993
0.7619	Intermediate Similarity	NPC311769
0.7619	Intermediate Similarity	NPC472940
0.7619	Intermediate Similarity	NPC182106
0.7619	Intermediate Similarity	NPC11711
0.7614	Intermediate Similarity	NPC474807
0.7614	Intermediate Similarity	NPC474736
0.7606	Intermediate Similarity	NPC270042
0.759	Intermediate Similarity	NPC470046
0.759	Intermediate Similarity	NPC53733
0.759	Intermediate Similarity	NPC21667
0.759	Intermediate Similarity	NPC470047
0.759	Intermediate Similarity	NPC168188
0.759	Intermediate Similarity	NPC470015
0.7586	Intermediate Similarity	NPC126993
0.7571	Intermediate Similarity	NPC311852
0.7561	Intermediate Similarity	NPC278459
0.7561	Intermediate Similarity	NPC475863
0.7561	Intermediate Similarity	NPC4166
0.7561	Intermediate Similarity	NPC473217
0.7561	Intermediate Similarity	NPC201912
0.7561	Intermediate Similarity	NPC38350
0.7556	Intermediate Similarity	NPC111684
0.7556	Intermediate Similarity	NPC58052

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 NPC293803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	2096
0.2-0.3	4556
0.3-0.4	1633
0.4-0.5	302
0.5-0.6	128
0.6-0.7	158
0.7-0.8	54
0.8-0.85	3
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9143	High Similarity	NPD4747	Approved
0.9143	High Similarity	NPD4691	Approved
0.9028	High Similarity	NPD4058	Approved
0.9	High Similarity	NPD4137	Phase 3
0.8767	High Similarity	NPD4687	Approved
0.8767	High Similarity	NPD5733	Approved
0.8592	High Similarity	NPD3621	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD5276	Approved
0.7901	Intermediate Similarity	NPD4221	Approved
0.7901	Intermediate Similarity	NPD4223	Phase 3
0.7831	Intermediate Similarity	NPD5329	Approved
0.7805	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8028	Phase 2
0.7765	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD5690	Phase 2
0.7711	Intermediate Similarity	NPD4197	Approved
0.7701	Intermediate Similarity	NPD6079	Approved
0.7558	Intermediate Similarity	NPD6672	Approved
0.7558	Intermediate Similarity	NPD5737	Approved
0.7531	Intermediate Similarity	NPD4195	Approved
0.7529	Intermediate Similarity	NPD7334	Approved
0.7529	Intermediate Similarity	NPD5330	Approved
0.7529	Intermediate Similarity	NPD4693	Phase 3
0.7529	Intermediate Similarity	NPD6684	Approved
0.7529	Intermediate Similarity	NPD6409	Approved
0.7529	Intermediate Similarity	NPD5205	Approved
0.7529	Intermediate Similarity	NPD7521	Approved
0.7529	Intermediate Similarity	NPD4688	Approved
0.7529	Intermediate Similarity	NPD7146	Approved
0.7529	Intermediate Similarity	NPD4690	Approved
0.7529	Intermediate Similarity	NPD4138	Approved
0.7529	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD4786	Approved
0.7471	Intermediate Similarity	NPD6673	Approved
0.7471	Intermediate Similarity	NPD6080	Approved
0.7471	Intermediate Similarity	NPD5328	Approved
0.7471	Intermediate Similarity	NPD6904	Approved
0.7407	Intermediate Similarity	NPD3617	Approved
0.7356	Intermediate Similarity	NPD6903	Approved
0.7356	Intermediate Similarity	NPD5208	Approved
0.7326	Intermediate Similarity	NPD3618	Phase 1
0.7326	Intermediate Similarity	NPD6098	Approved
0.7326	Intermediate Similarity	NPD4694	Approved
0.7326	Intermediate Similarity	NPD5280	Approved
0.7326	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD287	Approved
0.7273	Intermediate Similarity	NPD4753	Phase 2
0.7262	Intermediate Similarity	NPD3667	Approved
0.7253	Intermediate Similarity	NPD5210	Approved
0.7253	Intermediate Similarity	NPD4629	Approved
0.7241	Intermediate Similarity	NPD3573	Approved
0.7229	Intermediate Similarity	NPD4695	Discontinued
0.7191	Intermediate Similarity	NPD5207	Approved
0.7176	Intermediate Similarity	NPD4788	Approved
0.7174	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5222	Approved
0.7174	Intermediate Similarity	NPD5221	Approved
0.7126	Intermediate Similarity	NPD4623	Approved
0.7126	Intermediate Similarity	NPD5279	Phase 3
0.7126	Intermediate Similarity	NPD4519	Discontinued
0.7111	Intermediate Similarity	NPD5281	Approved
0.7111	Intermediate Similarity	NPD5694	Approved
0.7111	Intermediate Similarity	NPD5693	Phase 1
0.7111	Intermediate Similarity	NPD6050	Approved
0.7111	Intermediate Similarity	NPD5284	Approved
0.7097	Intermediate Similarity	NPD5173	Approved
0.7093	Intermediate Similarity	NPD3668	Phase 3
0.7065	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD5692	Phase 3
0.6957	Remote Similarity	NPD6001	Approved
0.6947	Remote Similarity	NPD4696	Approved
0.6947	Remote Similarity	NPD5286	Approved
0.6947	Remote Similarity	NPD5285	Approved
0.6923	Remote Similarity	NPD7515	Phase 2
0.6915	Remote Similarity	NPD6083	Phase 2
0.6915	Remote Similarity	NPD6084	Phase 2
0.6914	Remote Similarity	NPD4784	Approved
0.6914	Remote Similarity	NPD4785	Approved
0.6889	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD4243	Approved
0.6848	Remote Similarity	NPD6399	Phase 3
0.6813	Remote Similarity	NPD4096	Approved
0.6809	Remote Similarity	NPD4697	Phase 3
0.6804	Remote Similarity	NPD4633	Approved
0.6804	Remote Similarity	NPD5226	Approved
0.6804	Remote Similarity	NPD5211	Phase 2
0.6804	Remote Similarity	NPD5225	Approved
0.6804	Remote Similarity	NPD5091	Approved
0.6804	Remote Similarity	NPD5224	Approved
0.6778	Remote Similarity	NPD4518	Approved
0.6774	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7900	Approved
0.6774	Remote Similarity	NPD7748	Approved
0.6744	Remote Similarity	NPD4139	Approved
0.6744	Remote Similarity	NPD4692	Approved
0.6737	Remote Similarity	NPD4755	Approved
0.6735	Remote Similarity	NPD5174	Approved
0.6735	Remote Similarity	NPD5175	Approved
0.6702	Remote Similarity	NPD5695	Phase 3
0.67	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD5133	Approved
0.6634	Remote Similarity	NPD6881	Approved
0.6634	Remote Similarity	NPD6899	Approved
0.6632	Remote Similarity	NPD7732	Phase 3
0.6632	Remote Similarity	NPD7614	Phase 1
0.6629	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6942	Approved
0.6627	Remote Similarity	NPD7339	Approved
0.6598	Remote Similarity	NPD4700	Approved
0.6566	Remote Similarity	NPD6052	Approved
0.6562	Remote Similarity	NPD7902	Approved
0.6535	Remote Similarity	NPD5697	Approved
0.6526	Remote Similarity	NPD5654	Approved
0.6505	Remote Similarity	NPD7290	Approved
0.6505	Remote Similarity	NPD6883	Approved
0.6505	Remote Similarity	NPD7102	Approved
0.6477	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4730	Approved
0.6471	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD5168	Approved
0.6471	Remote Similarity	NPD4729	Approved
0.6442	Remote Similarity	NPD6649	Approved
0.6442	Remote Similarity	NPD6869	Approved
0.6442	Remote Similarity	NPD6650	Approved
0.6442	Remote Similarity	NPD8130	Phase 1
0.6442	Remote Similarity	NPD6847	Approved
0.6442	Remote Similarity	NPD6617	Approved
0.6436	Remote Similarity	NPD6402	Approved
0.6436	Remote Similarity	NPD5739	Approved
0.6436	Remote Similarity	NPD7128	Approved
0.6436	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD4190	Phase 3
0.6429	Remote Similarity	NPD5275	Approved
0.6429	Remote Similarity	NPD6404	Discontinued
0.6421	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6012	Approved
0.6408	Remote Similarity	NPD6014	Approved
0.6408	Remote Similarity	NPD6013	Approved
0.64	Remote Similarity	NPD4754	Approved
0.6392	Remote Similarity	NPD3495	Discontinued
0.6392	Remote Similarity	NPD5959	Approved
0.6381	Remote Similarity	NPD8297	Approved
0.6381	Remote Similarity	NPD6882	Approved
0.6373	Remote Similarity	NPD6412	Phase 2
0.6346	Remote Similarity	NPD5249	Phase 3
0.6346	Remote Similarity	NPD5247	Approved
0.6346	Remote Similarity	NPD5250	Approved
0.6346	Remote Similarity	NPD5251	Approved
0.6346	Remote Similarity	NPD4634	Approved
0.6346	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5248	Approved
0.6346	Remote Similarity	NPD5169	Approved
0.6346	Remote Similarity	NPD5135	Approved
0.6341	Remote Similarity	NPD6939	Phase 2
0.6341	Remote Similarity	NPD7144	Approved
0.6341	Remote Similarity	NPD7143	Approved
0.6341	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7094	Approved
0.6321	Remote Similarity	NPD6858	Approved
0.6311	Remote Similarity	NPD7320	Approved
0.6311	Remote Similarity	NPD5128	Approved
0.6296	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5360	Phase 3
0.6296	Remote Similarity	NPD7115	Discovery
0.6286	Remote Similarity	NPD5216	Approved
0.6286	Remote Similarity	NPD5127	Approved
0.6286	Remote Similarity	NPD5217	Approved
0.6286	Remote Similarity	NPD5215	Approved
0.6275	Remote Similarity	NPD4767	Approved
0.6275	Remote Similarity	NPD4768	Approved
0.6275	Remote Similarity	NPD6008	Approved
0.6265	Remote Similarity	NPD7150	Approved
0.6265	Remote Similarity	NPD7152	Approved
0.6265	Remote Similarity	NPD7151	Approved
0.6264	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD7525	Registered
0.625	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD7331	Phase 2
0.622	Remote Similarity	NPD6923	Approved
0.622	Remote Similarity	NPD6922	Approved
0.6214	Remote Similarity	NPD5701	Approved
0.6211	Remote Similarity	NPD8035	Phase 2
0.6211	Remote Similarity	NPD8034	Phase 2
0.6207	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6868	Approved
0.6182	Remote Similarity	NPD7610	Discontinued
0.6176	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4632	Approved
0.6163	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7638	Approved
0.6146	Remote Similarity	NPD7631	Approved
0.6145	Remote Similarity	NPD4789	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