NPASS Compound

Structure

NPC119326 OpenBabel07101718182D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 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 4.3301 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 19 2 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 29 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 1 0 0 0 22 26 1 0 0 0 0 22 27 2 0 0 0 0 23 26 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 31 2 0 0 0 0 25 28 1 1 0 0 0 25 29 1 0 0 0 0 26 32 2 0 0 0 0 27 33 1 0 0 0 0 28 3 1 6 0 0 0 29 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	447.28
Volume:	492.19
LogP:	6.011
LogD:	4.425
LogS:	-4.812
# Rotatable Bonds:	5
TPSA:	73.05
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	4.428
Fsp3:	0.483
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.971
MDCK Permeability:	1.8995689970324747e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	99.55208587646484%
Volume Distribution (VD):	3.25
Pgp-substrate:	0.9472679495811462%

ADMET: Metabolism

CYP1A2-inhibitor:	0.221
CYP1A2-substrate:	0.402
CYP2C19-inhibitor:	0.306
CYP2C19-substrate:	0.282
CYP2C9-inhibitor:	0.176
CYP2C9-substrate:	0.661
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.268
CYP3A4-substrate:	0.464

ADMET: Excretion

Clearance (CL):	6.79
Half-life (T1/2):	0.398

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.591
Skin Sensitization:	0.97
Carcinogencity:	0.269
Eye Corrosion:	0.004
Eye Irritation:	0.899
Respiratory Toxicity:	0.845

Download Data

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

Natural Product: NPC119326

Natural Product ID:	NPC119326
*Common Name:**	ZRZRJHAYWIOCML-DAORKYKSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZRZRJHAYWIOCML-DAORKYKSSA-N
Standard InCHI:	InChI=1S/C29H37NO3/c1-19-9-8-12-25-28(19,3)15-13-20(2)29(25,4)18-22-26(32)23(17-24(31)27(22)33)30-16-14-21-10-6-5-7-11-21/h5-7,9-11,17,20,25,30,33H,8,12-16,18H2,1-4H3/t20-,25+,28-,29+/m0/s1
SMILES:	CC1=CCC[C@@H]2[C@@]1(C)CC[C@H](C)[C@@]2(C)CC1=C(C(=O)C=C(C1=O)NCCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109399
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO13603	Dactylospongia metachromia	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479418]
NPO13603	Dactylospongia metachromia	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[33387695]
NPO13603	Dactylospongia metachromia	Species	Thorectidae	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
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	1100.0	nM	PMID[453538]

☑ 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 NPC119326 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	149
0.1-0.2	1020
0.2-0.3	4124
0.3-0.4	13098
0.4-0.5	20139
0.5-0.6	3873
0.6-0.7	275
0.7-0.8	15
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8613	High Similarity	NPC2672
0.7881	Intermediate Similarity	NPC34193
0.75	Intermediate Similarity	NPC24596
0.7479	Intermediate Similarity	NPC472788
0.7394	Intermediate Similarity	NPC153007
0.7381	Intermediate Similarity	NPC72688
0.7339	Intermediate Similarity	NPC185929
0.7154	Intermediate Similarity	NPC176336
0.7143	Intermediate Similarity	NPC126458
0.7099	Intermediate Similarity	NPC472164
0.7071	Intermediate Similarity	NPC179224
0.6957	Remote Similarity	NPC192533
0.6941	Remote Similarity	NPC47190
0.6929	Remote Similarity	NPC167336
0.6894	Remote Similarity	NPC126676
0.6894	Remote Similarity	NPC469671
0.6879	Remote Similarity	NPC40488
0.6875	Remote Similarity	NPC474473
0.687	Remote Similarity	NPC275410
0.6821	Remote Similarity	NPC246412
0.6818	Remote Similarity	NPC143768
0.6803	Remote Similarity	NPC246757
0.6803	Remote Similarity	NPC291070
0.6797	Remote Similarity	NPC67043
0.6791	Remote Similarity	NPC473573
0.6786	Remote Similarity	NPC79698
0.6781	Remote Similarity	NPC478140
0.6774	Remote Similarity	NPC239185
0.6761	Remote Similarity	NPC116057
0.6755	Remote Similarity	NPC119569
0.6746	Remote Similarity	NPC476993
0.6742	Remote Similarity	NPC218855
0.6741	Remote Similarity	NPC469843
0.672	Remote Similarity	NPC134882
0.672	Remote Similarity	NPC75724
0.6716	Remote Similarity	NPC113099
0.6692	Remote Similarity	NPC470253
0.6692	Remote Similarity	NPC471481
0.6689	Remote Similarity	NPC473804
0.6667	Remote Similarity	NPC472165
0.6644	Remote Similarity	NPC315051
0.6644	Remote Similarity	NPC150712
0.6643	Remote Similarity	NPC472413
0.6642	Remote Similarity	NPC234637
0.6642	Remote Similarity	NPC130591
0.6641	Remote Similarity	NPC475939
0.6641	Remote Similarity	NPC472691
0.6641	Remote Similarity	NPC471829
0.6641	Remote Similarity	NPC474866
0.664	Remote Similarity	NPC265220
0.6619	Remote Similarity	NPC71684
0.6614	Remote Similarity	NPC109514
0.6613	Remote Similarity	NPC260233
0.6593	Remote Similarity	NPC246904
0.6585	Remote Similarity	NPC1682
0.6585	Remote Similarity	NPC188844
0.6585	Remote Similarity	NPC59677
0.6569	Remote Similarity	NPC80605
0.6569	Remote Similarity	NPC323440
0.6569	Remote Similarity	NPC222968
0.656	Remote Similarity	NPC185208
0.656	Remote Similarity	NPC219573
0.6557	Remote Similarity	NPC67585
0.6557	Remote Similarity	NPC303967
0.6557	Remote Similarity	NPC110420
0.6554	Remote Similarity	NPC208725
0.6552	Remote Similarity	NPC183722
0.6549	Remote Similarity	NPC477248
0.6549	Remote Similarity	NPC477249
0.6538	Remote Similarity	NPC473418
0.6525	Remote Similarity	NPC472415
0.6519	Remote Similarity	NPC294458
0.6519	Remote Similarity	NPC326664
0.6515	Remote Similarity	NPC175585
0.6512	Remote Similarity	NPC274443
0.6508	Remote Similarity	NPC240042
0.6507	Remote Similarity	NPC473962
0.6504	Remote Similarity	NPC284475
0.6503	Remote Similarity	NPC477937
0.65	Remote Similarity	NPC103292
0.6493	Remote Similarity	NPC186128
0.6493	Remote Similarity	NPC292834
0.6489	Remote Similarity	NPC473498
0.6489	Remote Similarity	NPC100767
0.6479	Remote Similarity	NPC328107
0.6479	Remote Similarity	NPC285394
0.6475	Remote Similarity	NPC298115
0.6471	Remote Similarity	NPC93181
0.6463	Remote Similarity	NPC473484
0.6457	Remote Similarity	NPC49994
0.6452	Remote Similarity	NPC153885
0.6452	Remote Similarity	NPC323420
0.6447	Remote Similarity	NPC472241
0.6444	Remote Similarity	NPC474584
0.6439	Remote Similarity	NPC470007
0.6434	Remote Similarity	NPC244427
0.6434	Remote Similarity	NPC222390
0.6429	Remote Similarity	NPC179605
0.6429	Remote Similarity	NPC279385
0.642	Remote Similarity	NPC472121
0.6418	Remote Similarity	NPC265513
0.6418	Remote Similarity	NPC319579
0.6414	Remote Similarity	NPC71271
0.6412	Remote Similarity	NPC134120
0.6412	Remote Similarity	NPC172483
0.6412	Remote Similarity	NPC471186
0.6403	Remote Similarity	NPC220698
0.6403	Remote Similarity	NPC318173
0.64	Remote Similarity	NPC34243
0.64	Remote Similarity	NPC238219
0.6397	Remote Similarity	NPC471721
0.6395	Remote Similarity	NPC53044
0.6391	Remote Similarity	NPC470252
0.6387	Remote Similarity	NPC470579
0.6385	Remote Similarity	NPC247976
0.6385	Remote Similarity	NPC202613
0.6378	Remote Similarity	NPC122493
0.6378	Remote Similarity	NPC10781
0.6378	Remote Similarity	NPC293628
0.6376	Remote Similarity	NPC470441
0.6371	Remote Similarity	NPC133461
0.637	Remote Similarity	NPC471189
0.6364	Remote Similarity	NPC472700
0.6364	Remote Similarity	NPC472699
0.6351	Remote Similarity	NPC313663
0.6351	Remote Similarity	NPC149379
0.6338	Remote Similarity	NPC268534
0.6336	Remote Similarity	NPC275467
0.6336	Remote Similarity	NPC329282
0.6335	Remote Similarity	NPC222029
0.6328	Remote Similarity	NPC145052
0.6324	Remote Similarity	NPC93287
0.6323	Remote Similarity	NPC472242
0.632	Remote Similarity	NPC155232
0.6319	Remote Similarity	NPC472414
0.6316	Remote Similarity	NPC472683
0.6316	Remote Similarity	NPC472695
0.6316	Remote Similarity	NPC472701
0.6316	Remote Similarity	NPC472696
0.6312	Remote Similarity	NPC161956
0.6312	Remote Similarity	NPC112373
0.6312	Remote Similarity	NPC27833
0.6312	Remote Similarity	NPC258531
0.6311	Remote Similarity	NPC60408
0.6308	Remote Similarity	NPC58200
0.6304	Remote Similarity	NPC260886
0.6301	Remote Similarity	NPC478162
0.6301	Remote Similarity	NPC209389
0.6301	Remote Similarity	NPC478165
0.6296	Remote Similarity	NPC36495
0.6289	Remote Similarity	NPC473002
0.6284	Remote Similarity	NPC42423
0.6279	Remote Similarity	NPC54647
0.6276	Remote Similarity	NPC322433
0.6273	Remote Similarity	NPC93343
0.6268	Remote Similarity	NPC257490
0.626	Remote Similarity	NPC471317
0.626	Remote Similarity	NPC157778
0.6259	Remote Similarity	NPC472245
0.6258	Remote Similarity	NPC315368
0.625	Remote Similarity	NPC324569
0.625	Remote Similarity	NPC469903
0.625	Remote Similarity	NPC318067
0.625	Remote Similarity	NPC133135
0.625	Remote Similarity	NPC222466
0.625	Remote Similarity	NPC251579
0.6241	Remote Similarity	NPC85560
0.6241	Remote Similarity	NPC291962
0.6241	Remote Similarity	NPC177684
0.6241	Remote Similarity	NPC204784
0.6241	Remote Similarity	NPC327481
0.6241	Remote Similarity	NPC476645
0.6241	Remote Similarity	NPC226143
0.6241	Remote Similarity	NPC244933
0.6235	Remote Similarity	NPC104345
0.6232	Remote Similarity	NPC215419
0.6231	Remote Similarity	NPC128248
0.6231	Remote Similarity	NPC225079
0.6231	Remote Similarity	NPC136810
0.6231	Remote Similarity	NPC264728
0.6231	Remote Similarity	NPC474582
0.6231	Remote Similarity	NPC133809
0.6224	Remote Similarity	NPC39818
0.6222	Remote Similarity	NPC163867
0.622	Remote Similarity	NPC256452
0.622	Remote Similarity	NPC329430
0.622	Remote Similarity	NPC472880
0.6216	Remote Similarity	NPC316746
0.6216	Remote Similarity	NPC471832
0.6214	Remote Similarity	NPC268930
0.6209	Remote Similarity	NPC238108
0.6209	Remote Similarity	NPC472243
0.6207	Remote Similarity	NPC101719
0.6207	Remote Similarity	NPC470343
0.6207	Remote Similarity	NPC472244
0.6207	Remote Similarity	NPC295664
0.6204	Remote Similarity	NPC469547
0.6204	Remote Similarity	NPC477475
0.6204	Remote Similarity	NPC477476
0.6202	Remote Similarity	NPC322598

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 NPC119326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	126
0.1-0.2	548
0.2-0.3	832
0.3-0.4	2002
0.4-0.5	3771
0.5-0.6	1637
0.6-0.7	232
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
0.7192	Intermediate Similarity	NPD7082	Approved
0.7037	Intermediate Similarity	NPD5836	Discontinued
0.6985	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2319	Discontinued
0.696	Remote Similarity	NPD6024	Approved
0.696	Remote Similarity	NPD6027	Approved
0.6929	Remote Similarity	NPD2197	Approved
0.6929	Remote Similarity	NPD2192	Approved
0.6913	Remote Similarity	NPD7259	Approved
0.6911	Remote Similarity	NPD1100	Approved
0.6911	Remote Similarity	NPD4655	Approved
0.6911	Remote Similarity	NPD1099	Approved
0.6911	Remote Similarity	NPD4657	Approved
0.6885	Remote Similarity	NPD4094	Approved
0.6867	Remote Similarity	NPD7295	Approved
0.6866	Remote Similarity	NPD5162	Approved
0.6825	Remote Similarity	NPD2193	Phase 2
0.6825	Remote Similarity	NPD2648	Phase 3
0.6803	Remote Similarity	NPD2878	Approved
0.6803	Remote Similarity	NPD3980	Approved
0.6803	Remote Similarity	NPD3982	Approved
0.6786	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2754	Discontinued
0.6774	Remote Similarity	NPD3495	Discontinued
0.6763	Remote Similarity	NPD1077	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1073	Approved
0.6716	Remote Similarity	NPD1074	Approved
0.6716	Remote Similarity	NPD1075	Approved
0.6711	Remote Similarity	NPD7720	Phase 2
0.6693	Remote Similarity	NPD2196	Discontinued
0.6667	Remote Similarity	NPD1763	Approved
0.6667	Remote Similarity	NPD7478	Approved
0.6667	Remote Similarity	NPD7088	Discontinued
0.6667	Remote Similarity	NPD2056	Discontinued
0.6667	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1767	Approved
0.6667	Remote Similarity	NPD1766	Approved
0.6667	Remote Similarity	NPD1765	Approved
0.6667	Remote Similarity	NPD1761	Approved
0.6645	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1370	Approved
0.6642	Remote Similarity	NPD1374	Approved
0.6642	Remote Similarity	NPD1371	Approved
0.6642	Remote Similarity	NPD1373	Approved
0.6622	Remote Similarity	NPD6342	Discontinued
0.6596	Remote Similarity	NPD4677	Discontinued
0.6594	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1021	Approved
0.6593	Remote Similarity	NPD1023	Approved
0.6593	Remote Similarity	NPD1022	Approved
0.6593	Remote Similarity	NPD1020	Approved
0.6585	Remote Similarity	NPD7631	Approved
0.6579	Remote Similarity	NPD7487	Discontinued
0.6575	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4803	Discontinued
0.6562	Remote Similarity	NPD2171	Approved
0.6557	Remote Similarity	NPD5915	Approved
0.6554	Remote Similarity	NPD8125	Discontinued
0.6554	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3643	Approved
0.6541	Remote Similarity	NPD3642	Approved
0.6541	Remote Similarity	NPD3644	Approved
0.6538	Remote Similarity	NPD7606	Phase 3
0.6522	Remote Similarity	NPD5511	Discontinued
0.6512	Remote Similarity	NPD3357	Discontinued
0.6507	Remote Similarity	NPD5581	Approved
0.6504	Remote Similarity	NPD7609	Phase 3
0.649	Remote Similarity	NPD4461	Discontinued
0.6479	Remote Similarity	NPD2371	Approved
0.6479	Remote Similarity	NPD5157	Phase 1
0.6479	Remote Similarity	NPD5159	Phase 2
0.6479	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3551	Approved
0.6471	Remote Similarity	NPD747	Discontinued
0.6462	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD253	Approved
0.6446	Remote Similarity	NPD4145	Approved
0.6446	Remote Similarity	NPD4146	Approved
0.6443	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4733	Approved
0.6412	Remote Similarity	NPD1677	Discontinued
0.6412	Remote Similarity	NPD5717	Approved
0.6408	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD5466	Approved
0.6406	Remote Similarity	NPD2066	Phase 3
0.6403	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD7009	Phase 2
0.64	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6565	Approved
0.6389	Remote Similarity	NPD6563	Approved
0.6389	Remote Similarity	NPD6564	Approved
0.6387	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3881	Discontinued
0.6382	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD9566	Approved
0.6376	Remote Similarity	NPD2331	Discontinued
0.6371	Remote Similarity	NPD4543	Discontinued
0.637	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6994	Approved
0.6357	Remote Similarity	NPD6993	Approved
0.6357	Remote Similarity	NPD5630	Phase 1
0.6352	Remote Similarity	NPD5086	Approved
0.6351	Remote Similarity	NPD7713	Phase 3
0.6351	Remote Similarity	NPD7715	Approved
0.6351	Remote Similarity	NPD7714	Approved
0.6351	Remote Similarity	NPD1527	Phase 2
0.6349	Remote Similarity	NPD5554	Approved
0.6345	Remote Similarity	NPD4980	Approved
0.6331	Remote Similarity	NPD7610	Discontinued
0.6331	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD2607	Approved
0.6316	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD4416	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3426	Approved
0.6311	Remote Similarity	NPD3428	Approved
0.631	Remote Similarity	NPD5033	Approved
0.6309	Remote Similarity	NPD5182	Approved
0.6309	Remote Similarity	NPD5184	Approved
0.6309	Remote Similarity	NPD6623	Phase 3
0.6309	Remote Similarity	NPD5185	Approved
0.6308	Remote Similarity	NPD4119	Approved
0.6304	Remote Similarity	NPD4031	Approved
0.6304	Remote Similarity	NPD1323	Discontinued
0.6304	Remote Similarity	NPD4032	Approved
0.6301	Remote Similarity	NPD7084	Phase 3
0.6299	Remote Similarity	NPD2005	Discontinued
0.6296	Remote Similarity	NPD5927	Discontinued
0.6294	Remote Similarity	NPD6637	Approved
0.6291	Remote Similarity	NPD6295	Approved
0.6291	Remote Similarity	NPD6294	Approved
0.6286	Remote Similarity	NPD6835	Approved
0.6286	Remote Similarity	NPD6343	Approved
0.6286	Remote Similarity	NPD6345	Approved
0.6277	Remote Similarity	NPD3598	Phase 3
0.6276	Remote Similarity	NPD9540	Approved
0.6275	Remote Similarity	NPD2010	Phase 3
0.6273	Remote Similarity	NPD7091	Discontinued
0.627	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD4879	Approved
0.6259	Remote Similarity	NPD5263	Approved
0.6258	Remote Similarity	NPD5918	Discontinued
0.625	Remote Similarity	NPD7254	Discontinued
0.625	Remote Similarity	NPD3547	Approved
0.625	Remote Similarity	NPD2790	Discontinued
0.625	Remote Similarity	NPD3549	Approved
0.625	Remote Similarity	NPD182	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD7130	Phase 3
0.6241	Remote Similarity	NPD1710	Approved
0.6232	Remote Similarity	NPD2508	Discontinued
0.6232	Remote Similarity	NPD851	Approved
0.6232	Remote Similarity	NPD853	Approved
0.6225	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8131	Suspended
0.6215	Remote Similarity	NPD7283	Approved
0.6214	Remote Similarity	NPD5990	Approved
0.6214	Remote Similarity	NPD5991	Approved
0.621	Remote Similarity	NPD771	Phase 3
0.6207	Remote Similarity	NPD2199	Approved
0.6207	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5578	Approved
0.6207	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2198	Approved
0.6207	Remote Similarity	NPD6792	Phase 3
0.6204	Remote Similarity	NPD7094	Approved
0.6204	Remote Similarity	NPD6858	Approved
0.62	Remote Similarity	NPD3373	Approved
0.6199	Remote Similarity	NPD4956	Approved
0.6194	Remote Similarity	NPD2820	Phase 3
0.619	Remote Similarity	NPD1781	Discontinued
0.619	Remote Similarity	NPD4549	Discontinued
0.6185	Remote Similarity	NPD7962	Phase 2
0.6184	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7541	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD6852	Discontinued
0.6184	Remote Similarity	NPD6358	Phase 2
0.6183	Remote Similarity	NPD813	Approved
0.6183	Remote Similarity	NPD4817	Approved
0.6183	Remote Similarity	NPD4719	Phase 2
0.6183	Remote Similarity	NPD5716	Approved
0.6183	Remote Similarity	NPD4818	Approved
0.6181	Remote Similarity	NPD3071	Approved
0.6181	Remote Similarity	NPD3073	Approved
0.6181	Remote Similarity	NPD3072	Approved
0.6179	Remote Similarity	NPD2002	Discontinued
0.6179	Remote Similarity	NPD650	Approved
0.6172	Remote Similarity	NPD2895	Discontinued
0.6154	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1124	Approved
0.6154	Remote Similarity	NPD742	Approved
0.6154	Remote Similarity	NPD1123	Approved
0.6149	Remote Similarity	NPD5202	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