NPASS Compound

Structure

CID269058 OpenBabel06191716072D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.1302 6.4293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5246 5.9081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4273 3.1272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8450 -2.4710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7175 -1.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 2.4699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 -0.5207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7320 4.5753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7787 4.7782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0329 3.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 -1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 -0.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2239 1.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2236 0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6904 1.9501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8453 1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4778 5.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3806 2.9243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3803 1.9496 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6899 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6887 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6890 -0.9751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8442 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8448 -1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5352 1.4621 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5349 0.4871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8451 0.4876 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 2.5546 0.5006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5552 -1.4747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8439 1.4880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 29 1 0 0 0 0 19 3 1 1 0 0 0 19 20 1 0 0 0 0 20 27 1 6 0 0 0 21 26 1 0 0 0 0 21 30 1 6 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 24 26 1 0 0 0 0 24 32 1 1 0 0 0 25 30 1 1 0 0 0 25 33 1 0 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	508.388
LogP:	7.24
LogD:	5.294
LogS:	-4.677
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	5.839
Fsp3:	0.933
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:	-4.898
MDCK Permeability:	1.0200740689469967e-05
Pgp-inhibitor:	0.741
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.138
Plasma Protein Binding (PPB):	92.44123077392578%
Volume Distribution (VD):	1.203
Pgp-substrate:	2.1758804321289062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.172
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.683
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	10.477
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.433
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.815
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.887
Carcinogencity:	0.296
Eye Corrosion:	0.042
Eye Irritation:	0.02
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC269058

Natural Product ID:	NPC269058
*Common Name:**	DATCMCBQCCLKRF-HMSDPZTLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DATCMCBQCCLKRF-HMSDPZTLSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-18(2)9-8-10-19(3)20-13-14-28(7)22-12-11-21-26(4,5)24(32)23(31)25(33)30(21)17-29(22,30)16-15-27(20,28)6/h9,19-25,31-33H,8,10-17H2,1-7H3/t19-,20-,21+,22+,23+,24-,25+,27-,28+,29+,30-/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H]([C@@H]([C@@H]([C@]54C[C@@]35CC[C@]12C)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL258445
PubChem CID:	24770660
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	roots	northern Saudi desert	n.a.	PMID[10924184]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18177010]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5284	Ramalina hierrensis	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1586	Gorgonocephalus chilensis	Species	Gorgonocephalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5886	Fossombronia alaskana	Species	Fossombroniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8810	Pinus austriaca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29336	Corynandra chelidonii	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9036	Dipteryx lacunifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10085	Aspergillus varians	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2328	Lagochilus setulosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4463	Cytisus canariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9639	Prunus puddum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25831	Siphonoglossa sessilis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3693	Calpurnia aurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9883	Allium giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6022	Cytisus supinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8985	Gazania rigens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24891	Elmerina caryae	Species	Aporpiaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	50000.0	nM	PMID[526282]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[526282]

☑ 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 NPC269058 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	194
0.1-0.2	1682
0.2-0.3	6485
0.3-0.4	15760
0.4-0.5	7681
0.5-0.6	4986
0.6-0.7	4502
0.7-0.8	1224
0.8-0.85	123
0.85-0.9	52
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC71520
0.9625	High Similarity	NPC113978
0.9277	High Similarity	NPC94462
0.9186	High Similarity	NPC275671
0.9012	High Similarity	NPC13554
0.9012	High Similarity	NPC236112
0.9	High Similarity	NPC85346
0.9	High Similarity	NPC302041
0.9	High Similarity	NPC65897
0.8953	High Similarity	NPC109744
0.8941	High Similarity	NPC474657
0.8941	High Similarity	NPC186145
0.8916	High Similarity	NPC211135
0.8916	High Similarity	NPC216420
0.8916	High Similarity	NPC207013
0.8916	High Similarity	NPC85095
0.8902	High Similarity	NPC474531
0.8902	High Similarity	NPC470383
0.8851	High Similarity	NPC473956
0.8851	High Similarity	NPC475751
0.8837	High Similarity	NPC475664
0.8837	High Similarity	NPC67872
0.8824	High Similarity	NPC201273
0.8795	High Similarity	NPC30166
0.8791	High Similarity	NPC300179
0.8791	High Similarity	NPC102426
0.8765	High Similarity	NPC31828
0.8765	High Similarity	NPC244385
0.8765	High Similarity	NPC138621
0.8765	High Similarity	NPC312328
0.8765	High Similarity	NPC167037
0.8765	High Similarity	NPC6978
0.8765	High Similarity	NPC285761
0.875	High Similarity	NPC237460
0.8736	High Similarity	NPC470361
0.8736	High Similarity	NPC105495
0.869	High Similarity	NPC110778
0.869	High Similarity	NPC477818
0.8659	High Similarity	NPC472742
0.8659	High Similarity	NPC116119
0.8659	High Similarity	NPC273410
0.8659	High Similarity	NPC475727
0.8659	High Similarity	NPC80530
0.8659	High Similarity	NPC472463
0.8659	High Similarity	NPC80297
0.8636	High Similarity	NPC80561
0.8636	High Similarity	NPC329596
0.8636	High Similarity	NPC11216
0.8636	High Similarity	NPC204188
0.8636	High Similarity	NPC291484
0.8636	High Similarity	NPC3345
0.8625	High Similarity	NPC70982
0.8625	High Similarity	NPC230704
0.8621	High Similarity	NPC133588
0.8605	High Similarity	NPC125399
0.8605	High Similarity	NPC121981
0.8605	High Similarity	NPC6605
0.8602	High Similarity	NPC289670
0.8588	High Similarity	NPC209802
0.8588	High Similarity	NPC255882
0.8571	High Similarity	NPC248886
0.8554	High Similarity	NPC102253
0.8554	High Similarity	NPC475679
0.8554	High Similarity	NPC236237
0.8554	High Similarity	NPC322313
0.8539	High Similarity	NPC97404
0.8539	High Similarity	NPC41554
0.8537	High Similarity	NPC102708
0.8537	High Similarity	NPC87604
0.8519	High Similarity	NPC91573
0.8519	High Similarity	NPC189883
0.8506	High Similarity	NPC477600
0.8506	High Similarity	NPC470620
0.85	High Similarity	NPC308440
0.85	High Similarity	NPC196358
0.85	High Similarity	NPC254509
0.85	High Similarity	NPC49168
0.85	High Similarity	NPC5046
0.85	High Similarity	NPC472503
0.85	High Similarity	NPC145552
0.8488	Intermediate Similarity	NPC470360
0.8478	Intermediate Similarity	NPC476040
0.8478	Intermediate Similarity	NPC474994
0.8478	Intermediate Similarity	NPC476021
0.8471	Intermediate Similarity	NPC134481
0.8471	Intermediate Similarity	NPC193870
0.8471	Intermediate Similarity	NPC317458
0.8471	Intermediate Similarity	NPC82623
0.8471	Intermediate Similarity	NPC141941
0.8452	Intermediate Similarity	NPC242350
0.8444	Intermediate Similarity	NPC307776
0.8434	Intermediate Similarity	NPC328714
0.8434	Intermediate Similarity	NPC1319
0.8415	Intermediate Similarity	NPC202540
0.8415	Intermediate Similarity	NPC331618
0.8415	Intermediate Similarity	NPC257191
0.8415	Intermediate Similarity	NPC34019
0.8415	Intermediate Similarity	NPC130136
0.8415	Intermediate Similarity	NPC214570
0.8409	Intermediate Similarity	NPC474668
0.8409	Intermediate Similarity	NPC473436
0.8395	Intermediate Similarity	NPC200243
0.8395	Intermediate Similarity	NPC103822
0.8395	Intermediate Similarity	NPC471723
0.8395	Intermediate Similarity	NPC141071
0.8395	Intermediate Similarity	NPC257347
0.8391	Intermediate Similarity	NPC237344
0.8391	Intermediate Similarity	NPC24277
0.8391	Intermediate Similarity	NPC299068
0.8391	Intermediate Similarity	NPC6391
0.8375	Intermediate Similarity	NPC195489
0.8372	Intermediate Similarity	NPC475798
0.8372	Intermediate Similarity	NPC474493
0.8372	Intermediate Similarity	NPC185568
0.8372	Intermediate Similarity	NPC127606
0.8372	Intermediate Similarity	NPC86238
0.8372	Intermediate Similarity	NPC124172
0.837	Intermediate Similarity	NPC471903
0.8353	Intermediate Similarity	NPC296701
0.8353	Intermediate Similarity	NPC47763
0.8353	Intermediate Similarity	NPC218616
0.8353	Intermediate Similarity	NPC7988
0.8352	Intermediate Similarity	NPC477605
0.8352	Intermediate Similarity	NPC65402
0.8352	Intermediate Similarity	NPC127718
0.8333	Intermediate Similarity	NPC287749
0.8333	Intermediate Similarity	NPC210268
0.8333	Intermediate Similarity	NPC26117
0.8315	Intermediate Similarity	NPC101886
0.8315	Intermediate Similarity	NPC187785
0.8315	Intermediate Similarity	NPC138974
0.8315	Intermediate Similarity	NPC259875
0.8313	Intermediate Similarity	NPC148977
0.8313	Intermediate Similarity	NPC275910
0.8313	Intermediate Similarity	NPC477817
0.8313	Intermediate Similarity	NPC472342
0.8313	Intermediate Similarity	NPC477819
0.8295	Intermediate Similarity	NPC89747
0.8295	Intermediate Similarity	NPC475313
0.8293	Intermediate Similarity	NPC240604
0.8293	Intermediate Similarity	NPC321016
0.8293	Intermediate Similarity	NPC321381
0.8293	Intermediate Similarity	NPC202642
0.8293	Intermediate Similarity	NPC78067
0.8293	Intermediate Similarity	NPC46160
0.8293	Intermediate Similarity	NPC107059
0.8293	Intermediate Similarity	NPC129165
0.8293	Intermediate Similarity	NPC93662
0.8293	Intermediate Similarity	NPC300324
0.8293	Intermediate Similarity	NPC278091
0.8293	Intermediate Similarity	NPC134330
0.8293	Intermediate Similarity	NPC73875
0.828	Intermediate Similarity	NPC477226
0.828	Intermediate Similarity	NPC316604
0.8276	Intermediate Similarity	NPC22133
0.8261	Intermediate Similarity	NPC8774
0.8256	Intermediate Similarity	NPC232023
0.8256	Intermediate Similarity	NPC470929
0.8256	Intermediate Similarity	NPC159168
0.8256	Intermediate Similarity	NPC253402
0.825	Intermediate Similarity	NPC111234
0.8242	Intermediate Similarity	NPC310013
0.8235	Intermediate Similarity	NPC6707
0.8235	Intermediate Similarity	NPC209620
0.8235	Intermediate Similarity	NPC23852
0.8235	Intermediate Similarity	NPC70927
0.8214	Intermediate Similarity	NPC476316
0.8214	Intermediate Similarity	NPC30986
0.8214	Intermediate Similarity	NPC209430
0.8202	Intermediate Similarity	NPC280556
0.8202	Intermediate Similarity	NPC193360
0.8202	Intermediate Similarity	NPC212596
0.8202	Intermediate Similarity	NPC4574
0.8193	Intermediate Similarity	NPC198968
0.8193	Intermediate Similarity	NPC318495
0.8193	Intermediate Similarity	NPC471798
0.8193	Intermediate Similarity	NPC155986
0.8193	Intermediate Similarity	NPC477924
0.8182	Intermediate Similarity	NPC478094
0.8182	Intermediate Similarity	NPC261266
0.8182	Intermediate Similarity	NPC139724
0.8182	Intermediate Similarity	NPC477604
0.8172	Intermediate Similarity	NPC227583
0.8172	Intermediate Similarity	NPC98457
0.8172	Intermediate Similarity	NPC288970
0.8172	Intermediate Similarity	NPC210717
0.8172	Intermediate Similarity	NPC103165
0.8172	Intermediate Similarity	NPC12103
0.8171	Intermediate Similarity	NPC230301
0.8171	Intermediate Similarity	NPC178383
0.8171	Intermediate Similarity	NPC212879
0.8171	Intermediate Similarity	NPC22105
0.8171	Intermediate Similarity	NPC322353
0.8171	Intermediate Similarity	NPC185536
0.8171	Intermediate Similarity	NPC104387
0.8171	Intermediate Similarity	NPC477923
0.8171	Intermediate Similarity	NPC288035
0.8171	Intermediate Similarity	NPC66566
0.8171	Intermediate Similarity	NPC285893
0.8171	Intermediate Similarity	NPC304309

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 NPC269058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1883
0.2-0.3	4499
0.3-0.4	1835
0.4-0.5	370
0.5-0.6	151
0.6-0.7	182
0.7-0.8	42
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8554	High Similarity	NPD7525	Registered
0.8171	Intermediate Similarity	NPD7339	Approved
0.8171	Intermediate Similarity	NPD6942	Approved
0.8	Intermediate Similarity	NPD7645	Phase 2
0.8	Intermediate Similarity	NPD6929	Approved
0.7907	Intermediate Similarity	NPD6930	Phase 2
0.7907	Intermediate Similarity	NPD6931	Approved
0.7889	Intermediate Similarity	NPD7524	Approved
0.7857	Intermediate Similarity	NPD6933	Approved
0.7857	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6902	Approved
0.7765	Intermediate Similarity	NPD5776	Phase 2
0.7765	Intermediate Similarity	NPD6932	Approved
0.7765	Intermediate Similarity	NPD6925	Approved
0.7674	Intermediate Similarity	NPD7145	Approved
0.764	Intermediate Similarity	NPD6695	Phase 3
0.7619	Intermediate Similarity	NPD6924	Approved
0.7619	Intermediate Similarity	NPD6926	Approved
0.7586	Intermediate Similarity	NPD6683	Phase 2
0.7561	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4786	Approved
0.7556	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD7514	Phase 3
0.75	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6893	Approved
0.7391	Intermediate Similarity	NPD3618	Phase 1
0.7381	Intermediate Similarity	NPD7152	Approved
0.7381	Intermediate Similarity	NPD4243	Approved
0.7381	Intermediate Similarity	NPD7151	Approved
0.7381	Intermediate Similarity	NPD7150	Approved
0.7368	Intermediate Similarity	NPD6079	Approved
0.7349	Intermediate Similarity	NPD6922	Approved
0.7349	Intermediate Similarity	NPD6923	Approved
0.7333	Intermediate Similarity	NPD3667	Approved
0.7312	Intermediate Similarity	NPD7750	Discontinued
0.7303	Intermediate Similarity	NPD7332	Phase 2
0.7283	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7638	Approved
0.7262	Intermediate Similarity	NPD7143	Approved
0.7262	Intermediate Similarity	NPD7144	Approved
0.7222	Intermediate Similarity	NPD6898	Phase 1
0.7209	Intermediate Similarity	NPD4784	Approved
0.7209	Intermediate Similarity	NPD4785	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.72	Intermediate Similarity	NPD7640	Approved
0.7113	Intermediate Similarity	NPD4202	Approved
0.7111	Intermediate Similarity	NPD4748	Discontinued
0.7111	Intermediate Similarity	NPD7509	Discontinued
0.7027	Intermediate Similarity	NPD7516	Approved
0.701	Intermediate Similarity	NPD7087	Discontinued
0.7	Intermediate Similarity	NPD4755	Approved
0.6989	Remote Similarity	NPD3133	Approved
0.6989	Remote Similarity	NPD3666	Approved
0.6989	Remote Similarity	NPD3665	Phase 1
0.6961	Remote Similarity	NPD4159	Approved
0.6937	Remote Similarity	NPD7327	Approved
0.6937	Remote Similarity	NPD7328	Approved
0.6932	Remote Similarity	NPD5275	Approved
0.6932	Remote Similarity	NPD4190	Phase 3
0.6916	Remote Similarity	NPD4634	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD4697	Phase 3
0.6863	Remote Similarity	NPD4700	Approved
0.6863	Remote Similarity	NPD4696	Approved
0.6863	Remote Similarity	NPD5285	Approved
0.6863	Remote Similarity	NPD5286	Approved
0.6837	Remote Similarity	NPD7515	Phase 2
0.6832	Remote Similarity	NPD5173	Approved
0.6813	Remote Similarity	NPD4195	Approved
0.6804	Remote Similarity	NPD4753	Phase 2
0.6768	Remote Similarity	NPD6399	Phase 3
0.6754	Remote Similarity	NPD8380	Approved
0.6754	Remote Similarity	NPD8378	Approved
0.6754	Remote Similarity	NPD8296	Approved
0.6754	Remote Similarity	NPD8335	Approved
0.6754	Remote Similarity	NPD8379	Approved
0.6731	Remote Similarity	NPD5226	Approved
0.6731	Remote Similarity	NPD5224	Approved
0.6731	Remote Similarity	NPD5225	Approved
0.6731	Remote Similarity	NPD4633	Approved
0.6731	Remote Similarity	NPD5211	Phase 2
0.6703	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6118	Approved
0.6703	Remote Similarity	NPD6115	Approved
0.6703	Remote Similarity	NPD6114	Approved
0.6703	Remote Similarity	NPD6697	Approved
0.6702	Remote Similarity	NPD4788	Approved
0.6698	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD7128	Approved
0.6698	Remote Similarity	NPD6402	Approved
0.6698	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD3668	Phase 3
0.6609	Remote Similarity	NPD8033	Approved
0.6604	Remote Similarity	NPD5141	Approved
0.6602	Remote Similarity	NPD5290	Discontinued
0.6596	Remote Similarity	NPD4221	Approved
0.6596	Remote Similarity	NPD4223	Phase 3
0.6591	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4632	Approved
0.6574	Remote Similarity	NPD6899	Approved
0.6574	Remote Similarity	NPD7320	Approved
0.6574	Remote Similarity	NPD6881	Approved
0.6571	Remote Similarity	NPD7632	Discontinued
0.6566	Remote Similarity	NPD7136	Phase 2
0.6562	Remote Similarity	NPD5329	Approved
0.6556	Remote Similarity	NPD8264	Approved
0.6556	Remote Similarity	NPD3703	Phase 2
0.6549	Remote Similarity	NPD7115	Discovery
0.6542	Remote Similarity	NPD4768	Approved
0.6542	Remote Similarity	NPD4767	Approved
0.6535	Remote Similarity	NPD7748	Approved
0.6514	Remote Similarity	NPD6373	Approved
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6372	Approved
0.6509	Remote Similarity	NPD4754	Approved
0.6505	Remote Similarity	NPD6083	Phase 2
0.6505	Remote Similarity	NPD6084	Phase 2
0.6486	Remote Similarity	NPD8297	Approved
0.6484	Remote Similarity	NPD6117	Approved
0.6481	Remote Similarity	NPD5697	Approved
0.6481	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD4629	Approved
0.6458	Remote Similarity	NPD4197	Approved
0.6455	Remote Similarity	NPD6883	Approved
0.6455	Remote Similarity	NPD7102	Approved
0.6455	Remote Similarity	NPD7290	Approved
0.6444	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4225	Approved
0.6422	Remote Similarity	NPD4729	Approved
0.6422	Remote Similarity	NPD4730	Approved
0.6422	Remote Similarity	NPD5128	Approved
0.6413	Remote Similarity	NPD6116	Phase 1
0.6396	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD8130	Phase 1
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6649	Approved
0.6396	Remote Similarity	NPD6847	Approved
0.6396	Remote Similarity	NPD6869	Approved
0.6387	Remote Similarity	NPD7507	Approved
0.6383	Remote Similarity	NPD6928	Phase 2
0.6379	Remote Similarity	NPD6054	Approved
0.6379	Remote Similarity	NPD6059	Approved
0.6379	Remote Similarity	NPD6319	Approved
0.6364	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7604	Phase 2
0.6346	Remote Similarity	NPD7902	Approved
0.6339	Remote Similarity	NPD6882	Approved
0.6327	Remote Similarity	NPD7521	Approved
0.6327	Remote Similarity	NPD4688	Approved
0.6327	Remote Similarity	NPD5330	Approved
0.6327	Remote Similarity	NPD7334	Approved
0.6327	Remote Similarity	NPD7146	Approved
0.6327	Remote Similarity	NPD5205	Approved
0.6327	Remote Similarity	NPD6409	Approved
0.6327	Remote Similarity	NPD4690	Approved
0.6327	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4693	Phase 3
0.6327	Remote Similarity	NPD4138	Approved
0.6327	Remote Similarity	NPD4689	Approved
0.6327	Remote Similarity	NPD6684	Approved
0.6325	Remote Similarity	NPD7503	Approved
0.6321	Remote Similarity	NPD5344	Discontinued
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5251	Approved
0.6306	Remote Similarity	NPD5250	Approved
0.6306	Remote Similarity	NPD5248	Approved
0.6306	Remote Similarity	NPD5247	Approved
0.6306	Remote Similarity	NPD5249	Phase 3
0.63	Remote Similarity	NPD6051	Approved
0.6273	Remote Similarity	NPD6011	Approved
0.6273	Remote Similarity	NPD5168	Approved
0.6271	Remote Similarity	NPD6370	Approved
0.6261	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD5217	Approved
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5215	Approved
0.625	Remote Similarity	NPD5216	Approved
0.6239	Remote Similarity	NPD6640	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