NPASS Compound

Structure

NPC286229 OpenBabel07101719252D 27 28 0 0 1 0 0 0 0 0999 V2000 2.2112 -3.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6507 -3.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4655 2.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7911 -1.6991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8023 -1.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4511 1.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2473 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2999 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0316 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2473 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -2.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0316 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1676 -2.4809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8134 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2999 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8134 -1.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5329 -3.4118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5953 2.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5181 -2.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1788 -2.3318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 21 1 0 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 15 18 1 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 22 1 6 0 0 0 20 27 1 0 0 0 0 21 5 1 1 0 0 0 21 26 1 0 0 0 0 22 6 1 6 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	402.724
LogP:	3.567
LogD:	3.024
LogS:	-4.307
# Rotatable Bonds:	2
TPSA:	72.97
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	4.847
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.711
MDCK Permeability:	2.0416389816091396e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.844
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305
Plasma Protein Binding (PPB):	80.91143798828125%
Volume Distribution (VD):	1.133
Pgp-substrate:	20.320688247680664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.247
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.378
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.467
CYP3A4-substrate:	0.509

ADMET: Excretion

Clearance (CL):	6.006
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.403
AMES Toxicity:	0.135
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.488
Skin Sensitization:	0.944
Carcinogencity:	0.52
Eye Corrosion:	0.025
Eye Irritation:	0.029
Respiratory Toxicity:	0.668

Download Data

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

Natural Product: NPC286229

Natural Product ID:	NPC286229
*Common Name:**	Chandonanone C
IUPAC Name:	[(1R,6R,10E,14S)-6,10,14-trimethyl-2,9-dioxo-3-propan-2-ylidene-15-oxabicyclo[12.1.0]pentadec-10-en-6-yl] acetate
Synonyms:
Standard InCHIKey:	JNFYTEVLFJWCJH-VUWNFVCTSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-14(2)17-9-12-21(5,26-16(4)23)13-10-18(24)15(3)8-7-11-22(6)20(27-22)19(17)25/h8,20H,7,9-13H2,1-6H3/b15-8+/t20-,21+,22-/m0/s1
SMILES:	CC(=C1CC[C@](C)(CCC(=O)/C(=C/CC[C@@]2(C)[C@H](C1=O)O2)/C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109415
PubChem CID:	76310268
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32786	chandonanthus birmensis	Species	Anastrophyllaceae	Eukaryota	n.a.	Chinese liverworts	n.a.	PMID[24491225]
NPO11601	Chandonanthus hirtellus	Species	Anastrophyllaceae	Eukaryota	n.a.	Chinese liverworts	n.a.	PMID[24491225]
NPO11601	Chandonanthus hirtellus	Species	Anastrophyllaceae	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	7

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	=	40300.0	nM	PMID[530558]
NPT2452	Cell Line	NCI-H292		IC50	=	48700.0	nM	PMID[530558]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[530558]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	50000.0	nM	PMID[530558]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[530558]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37300.0	nM	PMID[530558]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40600.0	nM	PMID[530558]

☑ 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 NPC286229 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	230
0.1-0.2	1989
0.2-0.3	8494
0.3-0.4	14287
0.4-0.5	9726
0.5-0.6	5841
0.6-0.7	1815
0.7-0.8	292
0.8-0.85	15
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC471740
0.9221	High Similarity	NPC276647
0.9221	High Similarity	NPC622
0.8795	High Similarity	NPC471738
0.8795	High Similarity	NPC471739
0.8471	Intermediate Similarity	NPC475902
0.8391	Intermediate Similarity	NPC20713
0.8289	Intermediate Similarity	NPC477448
0.8289	Intermediate Similarity	NPC477449
0.8222	Intermediate Similarity	NPC476275
0.814	Intermediate Similarity	NPC197333
0.809	Intermediate Similarity	NPC202824
0.809	Intermediate Similarity	NPC477361
0.8068	Intermediate Similarity	NPC329857
0.8068	Intermediate Similarity	NPC469718
0.8046	Intermediate Similarity	NPC469628
0.8046	Intermediate Similarity	NPC471047
0.8046	Intermediate Similarity	NPC469653
0.8046	Intermediate Similarity	NPC475906
0.8046	Intermediate Similarity	NPC469631
0.8023	Intermediate Similarity	NPC279859
0.8023	Intermediate Similarity	NPC38576
0.8022	Intermediate Similarity	NPC477354
0.7952	Intermediate Similarity	NPC223904
0.7949	Intermediate Similarity	NPC475310
0.7889	Intermediate Similarity	NPC165383
0.7882	Intermediate Similarity	NPC170377
0.7821	Intermediate Similarity	NPC261398
0.7791	Intermediate Similarity	NPC32565
0.7791	Intermediate Similarity	NPC120726
0.7766	Intermediate Similarity	NPC469551
0.7742	Intermediate Similarity	NPC87090
0.7738	Intermediate Similarity	NPC304795
0.7727	Intermediate Similarity	NPC72513
0.7727	Intermediate Similarity	NPC266957
0.7727	Intermediate Similarity	NPC475703
0.7717	Intermediate Similarity	NPC474947
0.7717	Intermediate Similarity	NPC474490
0.7701	Intermediate Similarity	NPC96621
0.7701	Intermediate Similarity	NPC474547
0.7684	Intermediate Similarity	NPC477356
0.7684	Intermediate Similarity	NPC477511
0.7684	Intermediate Similarity	NPC264477
0.7683	Intermediate Similarity	NPC474527
0.7683	Intermediate Similarity	NPC471726
0.7674	Intermediate Similarity	NPC474703
0.7674	Intermediate Similarity	NPC1761
0.7674	Intermediate Similarity	NPC475989
0.7674	Intermediate Similarity	NPC272814
0.7674	Intermediate Similarity	NPC53867
0.7674	Intermediate Similarity	NPC475622
0.7674	Intermediate Similarity	NPC52609
0.7674	Intermediate Similarity	NPC108045
0.766	Intermediate Similarity	NPC477355
0.7653	Intermediate Similarity	NPC474716
0.7647	Intermediate Similarity	NPC475481
0.7647	Intermediate Similarity	NPC471325
0.7647	Intermediate Similarity	NPC79277
0.7647	Intermediate Similarity	NPC141810
0.764	Intermediate Similarity	NPC472008
0.7634	Intermediate Similarity	NPC17585
0.7619	Intermediate Similarity	NPC617
0.7614	Intermediate Similarity	NPC261721
0.7609	Intermediate Similarity	NPC469632
0.7609	Intermediate Similarity	NPC140543
0.7609	Intermediate Similarity	NPC148463
0.7586	Intermediate Similarity	NPC475796
0.7561	Intermediate Similarity	NPC475861
0.7558	Intermediate Similarity	NPC221231
0.7558	Intermediate Similarity	NPC173609
0.7558	Intermediate Similarity	NPC471326
0.7558	Intermediate Similarity	NPC85772
0.7556	Intermediate Similarity	NPC166919
0.7556	Intermediate Similarity	NPC83423
0.7529	Intermediate Similarity	NPC474510
0.7528	Intermediate Similarity	NPC231889
0.7528	Intermediate Similarity	NPC179659
0.7528	Intermediate Similarity	NPC472007
0.75	Intermediate Similarity	NPC290329
0.75	Intermediate Similarity	NPC110443
0.75	Intermediate Similarity	NPC128276
0.75	Intermediate Similarity	NPC128733
0.75	Intermediate Similarity	NPC474056
0.75	Intermediate Similarity	NPC185141
0.75	Intermediate Similarity	NPC133907
0.75	Intermediate Similarity	NPC164598
0.75	Intermediate Similarity	NPC474339
0.75	Intermediate Similarity	NPC201718
0.75	Intermediate Similarity	NPC476270
0.75	Intermediate Similarity	NPC46998
0.75	Intermediate Similarity	NPC472686
0.7474	Intermediate Similarity	NPC54843
0.7473	Intermediate Similarity	NPC475748
0.7473	Intermediate Similarity	NPC49342
0.7473	Intermediate Similarity	NPC251385
0.7473	Intermediate Similarity	NPC62815
0.7473	Intermediate Similarity	NPC471818
0.7471	Intermediate Similarity	NPC475947
0.7471	Intermediate Similarity	NPC318468
0.747	Intermediate Similarity	NPC472959
0.747	Intermediate Similarity	NPC266119
0.7468	Intermediate Similarity	NPC134385
0.7449	Intermediate Similarity	NPC477510
0.7449	Intermediate Similarity	NPC471143
0.7449	Intermediate Similarity	NPC474741
0.7447	Intermediate Similarity	NPC121036
0.7447	Intermediate Similarity	NPC473291
0.7447	Intermediate Similarity	NPC472674
0.7442	Intermediate Similarity	NPC474353
0.7439	Intermediate Similarity	NPC140287
0.7439	Intermediate Similarity	NPC476355
0.7439	Intermediate Similarity	NPC474551
0.7423	Intermediate Similarity	NPC118405
0.7423	Intermediate Similarity	NPC39996
0.7419	Intermediate Similarity	NPC471147
0.7419	Intermediate Similarity	NPC476267
0.7419	Intermediate Similarity	NPC121825
0.7416	Intermediate Similarity	NPC475491
0.7416	Intermediate Similarity	NPC469676
0.7416	Intermediate Similarity	NPC469626
0.7416	Intermediate Similarity	NPC104961
0.7416	Intermediate Similarity	NPC70422
0.7416	Intermediate Similarity	NPC472009
0.7416	Intermediate Similarity	NPC70555
0.7416	Intermediate Similarity	NPC122502
0.7412	Intermediate Similarity	NPC178277
0.7412	Intermediate Similarity	NPC469620
0.7412	Intermediate Similarity	NPC469690
0.7396	Intermediate Similarity	NPC477512
0.7391	Intermediate Similarity	NPC70595
0.7391	Intermediate Similarity	NPC111114
0.7391	Intermediate Similarity	NPC150978
0.7391	Intermediate Similarity	NPC219874
0.7391	Intermediate Similarity	NPC261607
0.7391	Intermediate Similarity	NPC74103
0.7391	Intermediate Similarity	NPC123177
0.7391	Intermediate Similarity	NPC300312
0.7386	Intermediate Similarity	NPC72464
0.7381	Intermediate Similarity	NPC476264
0.7381	Intermediate Similarity	NPC476325
0.7381	Intermediate Similarity	NPC470240
0.7381	Intermediate Similarity	NPC180290
0.7381	Intermediate Similarity	NPC57744
0.7381	Intermediate Similarity	NPC476794
0.7368	Intermediate Similarity	NPC471140
0.7363	Intermediate Similarity	NPC475971
0.7363	Intermediate Similarity	NPC78008
0.7363	Intermediate Similarity	NPC151770
0.7356	Intermediate Similarity	NPC475690
0.7353	Intermediate Similarity	NPC475495
0.7349	Intermediate Similarity	NPC226669
0.7349	Intermediate Similarity	NPC138408
0.7349	Intermediate Similarity	NPC155587
0.7349	Intermediate Similarity	NPC324762
0.7349	Intermediate Similarity	NPC193351
0.7349	Intermediate Similarity	NPC244166
0.7347	Intermediate Similarity	NPC472755
0.734	Intermediate Similarity	NPC470974
0.734	Intermediate Similarity	NPC475659
0.734	Intermediate Similarity	NPC470978
0.734	Intermediate Similarity	NPC31021
0.732	Intermediate Similarity	NPC474742
0.732	Intermediate Similarity	NPC472753
0.732	Intermediate Similarity	NPC47880
0.7317	Intermediate Similarity	NPC472956
0.7317	Intermediate Similarity	NPC474543
0.7317	Intermediate Similarity	NPC167145
0.7317	Intermediate Similarity	NPC238425
0.7317	Intermediate Similarity	NPC472018
0.7312	Intermediate Similarity	NPC248193
0.7312	Intermediate Similarity	NPC469645
0.7312	Intermediate Similarity	NPC469692
0.7312	Intermediate Similarity	NPC475302
0.7303	Intermediate Similarity	NPC319795
0.7303	Intermediate Similarity	NPC125290
0.7303	Intermediate Similarity	NPC50362
0.7303	Intermediate Similarity	NPC261380
0.7303	Intermediate Similarity	NPC99395
0.7303	Intermediate Similarity	NPC197903
0.7303	Intermediate Similarity	NPC38468
0.73	Intermediate Similarity	NPC477513
0.73	Intermediate Similarity	NPC469558
0.7294	Intermediate Similarity	NPC474341
0.7294	Intermediate Similarity	NPC472960
0.7292	Intermediate Similarity	NPC264378
0.7292	Intermediate Similarity	NPC161855
0.7284	Intermediate Similarity	NPC469660
0.7284	Intermediate Similarity	NPC69462
0.7284	Intermediate Similarity	NPC472955
0.7283	Intermediate Similarity	NPC265856
0.7283	Intermediate Similarity	NPC316228
0.7283	Intermediate Similarity	NPC166554
0.7283	Intermediate Similarity	NPC253144
0.7283	Intermediate Similarity	NPC477684
0.7283	Intermediate Similarity	NPC51653
0.7282	Intermediate Similarity	NPC475277
0.7282	Intermediate Similarity	NPC477093
0.7282	Intermediate Similarity	NPC473522
0.7273	Intermediate Similarity	NPC477784
0.7273	Intermediate Similarity	NPC477786

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 NPC286229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	2520
0.2-0.3	3896
0.3-0.4	1720
0.4-0.5	514
0.5-0.6	227
0.6-0.7	40
0.7-0.8	2
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
0.7303	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5369	Approved
0.7111	Intermediate Similarity	NPD5363	Approved
0.7089	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD7331	Phase 2
0.7	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5785	Approved
0.6882	Remote Similarity	NPD6672	Approved
0.6882	Remote Similarity	NPD5737	Approved
0.6809	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6101	Approved
0.6782	Remote Similarity	NPD4756	Discovery
0.6778	Remote Similarity	NPD5209	Approved
0.6778	Remote Similarity	NPD4269	Approved
0.6778	Remote Similarity	NPD4270	Approved
0.6778	Remote Similarity	NPD6435	Approved
0.6737	Remote Similarity	NPD46	Approved
0.6737	Remote Similarity	NPD6698	Approved
0.6701	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6635	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6673	Approved
0.6632	Remote Similarity	NPD6080	Approved
0.6632	Remote Similarity	NPD6904	Approved
0.6632	Remote Similarity	NPD1695	Approved
0.6598	Remote Similarity	NPD5778	Approved
0.6598	Remote Similarity	NPD5779	Approved
0.6571	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6881	Approved
0.6556	Remote Similarity	NPD4252	Approved
0.6556	Remote Similarity	NPD5368	Approved
0.6542	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD6649	Approved
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD6008	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6522	Remote Similarity	NPD7154	Phase 3
0.6509	Remote Similarity	NPD6372	Approved
0.6509	Remote Similarity	NPD6373	Approved
0.65	Remote Similarity	NPD6083	Phase 2
0.65	Remote Similarity	NPD6084	Phase 2
0.6495	Remote Similarity	NPD6050	Approved
0.6489	Remote Similarity	NPD7521	Approved
0.6489	Remote Similarity	NPD7334	Approved
0.6489	Remote Similarity	NPD5330	Approved
0.6489	Remote Similarity	NPD6684	Approved
0.6489	Remote Similarity	NPD6409	Approved
0.6489	Remote Similarity	NPD6422	Discontinued
0.6489	Remote Similarity	NPD7146	Approved
0.6476	Remote Similarity	NPD5697	Approved
0.6465	Remote Similarity	NPD5695	Phase 3
0.6463	Remote Similarity	NPD7341	Phase 2
0.6449	Remote Similarity	NPD6371	Approved
0.6449	Remote Similarity	NPD7290	Approved
0.6449	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD7102	Approved
0.6436	Remote Similarity	NPD5696	Approved
0.6421	Remote Similarity	NPD3573	Approved
0.642	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6011	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6413	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7839	Suspended
0.6392	Remote Similarity	NPD5692	Phase 3
0.6389	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD8130	Phase 1
0.6389	Remote Similarity	NPD6617	Approved
0.6389	Remote Similarity	NPD6847	Approved
0.6386	Remote Similarity	NPD3704	Approved
0.6383	Remote Similarity	NPD1694	Approved
0.6364	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8039	Approved
0.6364	Remote Similarity	NPD7900	Approved
0.6355	Remote Similarity	NPD6014	Approved
0.6355	Remote Similarity	NPD6013	Approved
0.6355	Remote Similarity	NPD6012	Approved
0.6354	Remote Similarity	NPD6903	Approved
0.6354	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD5362	Discontinued
0.6341	Remote Similarity	NPD3197	Phase 1
0.633	Remote Similarity	NPD6882	Approved
0.633	Remote Similarity	NPD8297	Approved
0.6327	Remote Similarity	NPD5693	Phase 1
0.6327	Remote Similarity	NPD5694	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD6098	Approved
0.63	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD7115	Discovery
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7838	Discovery
0.62	Remote Similarity	NPD7748	Approved
0.6196	Remote Similarity	NPD4695	Discontinued
0.6196	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5370	Suspended
0.6087	Remote Similarity	NPD6319	Approved
0.6053	Remote Similarity	NPD6335	Approved
0.6053	Remote Similarity	NPD29	Approved
0.6053	Remote Similarity	NPD28	Approved
0.6022	Remote Similarity	NPD4819	Approved
0.6022	Remote Similarity	NPD4821	Approved
0.6022	Remote Similarity	NPD4820	Approved
0.6022	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4822	Approved
0.6019	Remote Similarity	NPD6614	Approved
0.6019	Remote Similarity	NPD5959	Approved
0.6018	Remote Similarity	NPD6868	Approved
0.6018	Remote Similarity	NPD6274	Approved
0.6017	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD8779	Phase 3
0.6	Remote Similarity	NPD6110	Phase 1
0.598	Remote Similarity	NPD5654	Approved
0.5966	Remote Similarity	NPD6616	Approved
0.5965	Remote Similarity	NPD6317	Approved
0.5962	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4225	Approved
0.596	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6054	Approved
0.5932	Remote Similarity	NPD8328	Phase 3
0.5932	Remote Similarity	NPD7642	Approved
0.5932	Remote Similarity	NPD7604	Phase 2
0.5922	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5222	Approved
0.5922	Remote Similarity	NPD4697	Phase 3
0.5922	Remote Similarity	NPD5221	Approved
0.5917	Remote Similarity	NPD7078	Approved
0.5913	Remote Similarity	NPD6314	Approved
0.5913	Remote Similarity	NPD6313	Approved
0.5905	Remote Similarity	NPD5285	Approved
0.5905	Remote Similarity	NPD5286	Approved
0.5905	Remote Similarity	NPD4696	Approved
0.59	Remote Similarity	NPD5207	Approved
0.5882	Remote Similarity	NPD6001	Approved
0.5876	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1696	Phase 3
0.5868	Remote Similarity	NPD7736	Approved
0.5865	Remote Similarity	NPD4755	Approved
0.5865	Remote Similarity	NPD5173	Approved
0.5859	Remote Similarity	NPD5208	Approved
0.5856	Remote Similarity	NPD2067	Discontinued
0.5849	Remote Similarity	NPD5223	Approved
0.5847	Remote Similarity	NPD6370	Approved
0.5842	Remote Similarity	NPD6079	Approved
0.5841	Remote Similarity	NPD4632	Approved
0.5833	Remote Similarity	NPD5332	Approved
0.5833	Remote Similarity	NPD5331	Approved
0.5826	Remote Similarity	NPD6009	Approved
0.5825	Remote Similarity	NPD4629	Approved
0.5825	Remote Similarity	NPD5210	Approved
0.5823	Remote Similarity	NPD3194	Approved
0.5823	Remote Similarity	NPD3195	Phase 2
0.5823	Remote Similarity	NPD3196	Approved
0.5823	Remote Similarity	NPD4266	Approved
0.5816	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5279	Phase 3
0.5812	Remote Similarity	NPD6059	Approved
0.5806	Remote Similarity	NPD4271	Approved
0.5806	Remote Similarity	NPD3732	Approved
0.5806	Remote Similarity	NPD4268	Approved
0.58	Remote Similarity	NPD4753	Phase 2
0.58	Remote Similarity	NPD5328	Approved
0.5794	Remote Similarity	NPD5224	Approved
0.5794	Remote Similarity	NPD5225	Approved
0.5794	Remote Similarity	NPD5226	Approved
0.5794	Remote Similarity	NPD5211	Phase 2
0.5794	Remote Similarity	NPD4633	Approved
0.5789	Remote Similarity	NPD4790	Discontinued
0.5785	Remote Similarity	NPD8293	Discontinued
0.5776	Remote Similarity	NPD7641	Discontinued
0.5769	Remote Similarity	NPD7732	Phase 3
0.5763	Remote Similarity	NPD6908	Approved
0.5763	Remote Similarity	NPD6015	Approved
0.5763	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6909	Approved
0.5763	Remote Similarity	NPD5983	Phase 2
0.5763	Remote Similarity	NPD6016	Approved
0.5755	Remote Similarity	NPD4700	Approved
0.5755	Remote Similarity	NPD6648	Approved
0.5752	Remote Similarity	NPD6053	Discontinued
0.5747	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5174	Approved
0.5741	Remote Similarity	NPD5175	Approved
0.5732	Remote Similarity	NPD6109	Phase 1
0.5714	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD5329	Approved
0.5714	Remote Similarity	NPD8080	Discontinued
0.5714	Remote Similarity	NPD4634	Approved
0.5702	Remote Similarity	NPD6336	Discontinued

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