NPASS Compound

Structure

NPC282598 OpenBabel07101718292D 21 22 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 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 0.8660 -0.5000 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 -0.0000 1.0000 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 -0.8660 0.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 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 -0.8660 -2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 1 10 1 0 0 0 0 2 11 2 0 0 0 0 3 12 1 0 0 0 0 4 16 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 11 17 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 1 0 0 0 15 16 1 0 0 0 0 15 18 1 1 0 0 0 16 17 1 0 0 0 0 17 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.06
Volume:	329.641
LogP:	5.012
LogD:	3.964
LogS:	-5.635
# Rotatable Bonds:	2
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	5.06
Fsp3:	0.706
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.599
MDCK Permeability:	2.308743387402501e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.413
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	94.1611557006836%
Volume Distribution (VD):	3.259
Pgp-substrate:	6.412034511566162%

ADMET: Metabolism

CYP1A2-inhibitor:	0.305
CYP1A2-substrate:	0.27
CYP2C19-inhibitor:	0.861
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.781
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.401
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.849

ADMET: Excretion

Clearance (CL):	3.06
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.377
Drug-inuced Liver Injury (DILI):	0.74
AMES Toxicity:	0.254
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.114
Carcinogencity:	0.717
Eye Corrosion:	0.947
Eye Irritation:	0.673
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC282598

Natural Product ID:	NPC282598
*Common Name:**	Acetylelatol
IUPAC Name:	[(3S,4R,6R)-4-bromo-10-chloro-5,5,9-trimethyl-1-methylidenespiro[5.5]undec-9-en-3-yl] acetate
Synonyms:	Acetylelatol
Standard InCHIKey:	GQCHYEJJCOTYBA-YQQAZPJKSA-N
Standard InCHI:	InChI=1S/C17H24BrClO2/c1-10-6-7-17(9-13(10)19)11(2)8-14(21-12(3)20)15(18)16(17,4)5/h14-15H,2,6-9H2,1,3-5H3/t14-,15-,17+/m0/s1
SMILES:	CC(=O)O[C@H]1CC(=C)[C@@]2(C([C@H]1Br)(C)C)CCC(=C(C2)Cl)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449240
PubChem CID:	11588882
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002517] Chamigranes

*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
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	tenerife	n.a.	PMID[10924166]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309323]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22220686]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24279991]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	50300.0	nM	PMID[494607]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	13700.0	nM	PMID[494607]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	28000.0	nM	PMID[494607]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	22400.0	nM	PMID[494607]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	53000.0	nM	PMID[494607]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	44600.0	nM	PMID[494607]

☑ 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 NPC282598 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	203
0.1-0.2	1890
0.2-0.3	10549
0.3-0.4	16168
0.4-0.5	8597
0.5-0.6	4906
0.6-0.7	366
0.7-0.8	14
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9241	High Similarity	NPC15714
0.8605	High Similarity	NPC76909
0.8415	Intermediate Similarity	NPC31330
0.7711	Intermediate Similarity	NPC474946
0.7711	Intermediate Similarity	NPC35397
0.7558	Intermediate Similarity	NPC83436
0.7273	Intermediate Similarity	NPC113024
0.7241	Intermediate Similarity	NPC215307
0.7241	Intermediate Similarity	NPC274750
0.7222	Intermediate Similarity	NPC97491
0.7222	Intermediate Similarity	NPC273356
0.7191	Intermediate Similarity	NPC311891
0.7159	Intermediate Similarity	NPC44083
0.7159	Intermediate Similarity	NPC153987
0.7126	Intermediate Similarity	NPC283619
0.7097	Intermediate Similarity	NPC109900
0.7033	Intermediate Similarity	NPC132386
0.7	Intermediate Similarity	NPC195334
0.7	Intermediate Similarity	NPC25554
0.7	Intermediate Similarity	NPC142163
0.7	Intermediate Similarity	NPC290495
0.7	Intermediate Similarity	NPC108476
0.6966	Remote Similarity	NPC100906
0.6923	Remote Similarity	NPC286786
0.6923	Remote Similarity	NPC256112
0.6923	Remote Similarity	NPC471218
0.6889	Remote Similarity	NPC269791
0.6882	Remote Similarity	NPC469570
0.6882	Remote Similarity	NPC48210
0.6854	Remote Similarity	NPC35574
0.6818	Remote Similarity	NPC30575
0.6818	Remote Similarity	NPC469581
0.6813	Remote Similarity	NPC473420
0.6809	Remote Similarity	NPC102996
0.6809	Remote Similarity	NPC474970
0.6782	Remote Similarity	NPC277993
0.6782	Remote Similarity	NPC33876
0.6782	Remote Similarity	NPC77724
0.6778	Remote Similarity	NPC242767
0.6778	Remote Similarity	NPC476603
0.6742	Remote Similarity	NPC189206
0.6737	Remote Similarity	NPC102640
0.6703	Remote Similarity	NPC233332
0.6703	Remote Similarity	NPC469802
0.6702	Remote Similarity	NPC191965
0.6702	Remote Similarity	NPC35933
0.6667	Remote Similarity	NPC139206
0.6667	Remote Similarity	NPC474789
0.6667	Remote Similarity	NPC188896
0.6667	Remote Similarity	NPC69713
0.6667	Remote Similarity	NPC52108
0.6632	Remote Similarity	NPC264127
0.6632	Remote Similarity	NPC137306
0.6632	Remote Similarity	NPC9892
0.6632	Remote Similarity	NPC91525
0.6632	Remote Similarity	NPC325594
0.6632	Remote Similarity	NPC6979
0.6632	Remote Similarity	NPC329943
0.6632	Remote Similarity	NPC286153
0.6632	Remote Similarity	NPC10005
0.6632	Remote Similarity	NPC84121
0.663	Remote Similarity	NPC170303
0.6627	Remote Similarity	NPC474768
0.6598	Remote Similarity	NPC246028
0.6598	Remote Similarity	NPC261320
0.6596	Remote Similarity	NPC306951
0.6596	Remote Similarity	NPC96055
0.6596	Remote Similarity	NPC139566
0.6593	Remote Similarity	NPC158565
0.6591	Remote Similarity	NPC71152
0.6562	Remote Similarity	NPC478104
0.6562	Remote Similarity	NPC162107
0.6562	Remote Similarity	NPC46912
0.6562	Remote Similarity	NPC280810
0.6559	Remote Similarity	NPC73882
0.6556	Remote Similarity	NPC84868
0.6531	Remote Similarity	NPC474728
0.6531	Remote Similarity	NPC220216
0.6531	Remote Similarity	NPC48732
0.6526	Remote Similarity	NPC474013
0.6526	Remote Similarity	NPC476602
0.6522	Remote Similarity	NPC268827
0.6522	Remote Similarity	NPC469580
0.6505	Remote Similarity	NPC110897
0.65	Remote Similarity	NPC240206
0.6495	Remote Similarity	NPC472220
0.6495	Remote Similarity	NPC470613
0.6495	Remote Similarity	NPC224145
0.6495	Remote Similarity	NPC97884
0.6495	Remote Similarity	NPC473879
0.6495	Remote Similarity	NPC477128
0.6495	Remote Similarity	NPC470612
0.6489	Remote Similarity	NPC470948
0.6489	Remote Similarity	NPC476927
0.6489	Remote Similarity	NPC222358
0.6484	Remote Similarity	NPC4827
0.6484	Remote Similarity	NPC184737
0.6465	Remote Similarity	NPC77099
0.6465	Remote Similarity	NPC124374
0.6465	Remote Similarity	NPC60755
0.6465	Remote Similarity	NPC470590
0.6465	Remote Similarity	NPC49420
0.6465	Remote Similarity	NPC285184
0.6465	Remote Similarity	NPC26888
0.6458	Remote Similarity	NPC329692
0.6458	Remote Similarity	NPC73038
0.6458	Remote Similarity	NPC473226
0.6458	Remote Similarity	NPC471219
0.6452	Remote Similarity	NPC475665
0.6452	Remote Similarity	NPC159148
0.6452	Remote Similarity	NPC476101
0.6452	Remote Similarity	NPC327002
0.6444	Remote Similarity	NPC41017
0.6444	Remote Similarity	NPC92489
0.6444	Remote Similarity	NPC476607
0.6437	Remote Similarity	NPC92801
0.6436	Remote Similarity	NPC257510
0.6436	Remote Similarity	NPC299714
0.6429	Remote Similarity	NPC470588
0.6429	Remote Similarity	NPC224552
0.6429	Remote Similarity	NPC475049
0.6429	Remote Similarity	NPC474889
0.6429	Remote Similarity	NPC73995
0.6429	Remote Similarity	NPC473647
0.6429	Remote Similarity	NPC239453
0.6421	Remote Similarity	NPC100391
0.6421	Remote Similarity	NPC312660
0.6421	Remote Similarity	NPC102048
0.6413	Remote Similarity	NPC305835
0.6413	Remote Similarity	NPC327674
0.6413	Remote Similarity	NPC47808
0.64	Remote Similarity	NPC473678
0.64	Remote Similarity	NPC99653
0.6395	Remote Similarity	NPC208999
0.6392	Remote Similarity	NPC174273
0.6392	Remote Similarity	NPC471779
0.6392	Remote Similarity	NPC473097
0.6392	Remote Similarity	NPC166857
0.6392	Remote Similarity	NPC131329
0.6392	Remote Similarity	NPC245004
0.6383	Remote Similarity	NPC178676
0.6374	Remote Similarity	NPC472300
0.6364	Remote Similarity	NPC113989
0.6364	Remote Similarity	NPC148414
0.6364	Remote Similarity	NPC471896
0.6364	Remote Similarity	NPC152467
0.6364	Remote Similarity	NPC175628
0.6364	Remote Similarity	NPC280149
0.6364	Remote Similarity	NPC120840
0.6364	Remote Similarity	NPC78973
0.6364	Remote Similarity	NPC221111
0.6364	Remote Similarity	NPC111585
0.6364	Remote Similarity	NPC44240
0.6364	Remote Similarity	NPC328141
0.6354	Remote Similarity	NPC323765
0.6354	Remote Similarity	NPC109528
0.6344	Remote Similarity	NPC473685
0.6344	Remote Similarity	NPC281880
0.6344	Remote Similarity	NPC195424
0.6344	Remote Similarity	NPC304194
0.6344	Remote Similarity	NPC206735
0.6344	Remote Similarity	NPC474978
0.6337	Remote Similarity	NPC472416
0.6337	Remote Similarity	NPC470697
0.6337	Remote Similarity	NPC472360
0.6337	Remote Similarity	NPC38830
0.6337	Remote Similarity	NPC474922
0.6327	Remote Similarity	NPC290690
0.6327	Remote Similarity	NPC131453
0.6327	Remote Similarity	NPC242864
0.6327	Remote Similarity	NPC246708
0.6327	Remote Similarity	NPC277771
0.6327	Remote Similarity	NPC473242
0.6327	Remote Similarity	NPC474845
0.6327	Remote Similarity	NPC473229
0.6327	Remote Similarity	NPC181225
0.6327	Remote Similarity	NPC215831
0.6327	Remote Similarity	NPC474512
0.6327	Remote Similarity	NPC17733
0.6327	Remote Similarity	NPC93411
0.6327	Remote Similarity	NPC470629
0.6327	Remote Similarity	NPC40552
0.6322	Remote Similarity	NPC22301
0.6316	Remote Similarity	NPC57370
0.6316	Remote Similarity	NPC23748
0.6316	Remote Similarity	NPC474193
0.6316	Remote Similarity	NPC49208
0.6316	Remote Similarity	NPC193198
0.6316	Remote Similarity	NPC12283
0.6304	Remote Similarity	NPC321514
0.63	Remote Similarity	NPC477574
0.63	Remote Similarity	NPC177641
0.63	Remote Similarity	NPC234335
0.63	Remote Similarity	NPC186363
0.63	Remote Similarity	NPC233345
0.6292	Remote Similarity	NPC476609
0.6292	Remote Similarity	NPC471799
0.6289	Remote Similarity	NPC131813
0.6289	Remote Similarity	NPC195640
0.6289	Remote Similarity	NPC55309

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 NPC282598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	2253
0.2-0.3	4487
0.3-0.4	1699
0.4-0.5	363
0.5-0.6	165
0.6-0.7	1
0.7-0.8	0
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
0.6289	Remote Similarity	NPD7146	Approved
0.6289	Remote Similarity	NPD7521	Approved
0.6289	Remote Similarity	NPD6409	Approved
0.6289	Remote Similarity	NPD7334	Approved
0.6289	Remote Similarity	NPD6684	Approved
0.6289	Remote Similarity	NPD5330	Approved
0.6238	Remote Similarity	NPD6399	Phase 3
0.6176	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7900	Approved
0.6176	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6903	Approved
0.61	Remote Similarity	NPD6051	Approved
0.6087	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7632	Discontinued
0.6064	Remote Similarity	NPD7645	Phase 2
0.6061	Remote Similarity	NPD3573	Approved
0.6042	Remote Similarity	NPD3667	Approved
0.602	Remote Similarity	NPD1694	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD5737	Approved
0.598	Remote Similarity	NPD6411	Approved
0.598	Remote Similarity	NPD7515	Phase 2
0.5978	Remote Similarity	NPD7339	Approved
0.5978	Remote Similarity	NPD6942	Approved
0.5962	Remote Similarity	NPD5654	Approved
0.5918	Remote Similarity	NPD3668	Phase 3
0.5918	Remote Similarity	NPD4786	Approved
0.5876	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6274	Approved
0.5862	Remote Similarity	NPD6868	Approved
0.5849	Remote Similarity	NPD5959	Approved
0.5806	Remote Similarity	NPD8039	Approved
0.58	Remote Similarity	NPD3618	Phase 1
0.58	Remote Similarity	NPD6098	Approved
0.5794	Remote Similarity	NPD4225	Approved
0.5794	Remote Similarity	NPD7638	Approved
0.5784	Remote Similarity	NPD6101	Approved
0.5784	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6008	Approved
0.5763	Remote Similarity	NPD6313	Approved
0.5763	Remote Similarity	NPD6314	Approved
0.5763	Remote Similarity	NPD6335	Approved
0.5747	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7640	Approved
0.5741	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD7101	Approved
0.5714	Remote Similarity	NPD7100	Approved
0.57	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6924	Approved
0.5699	Remote Similarity	NPD6926	Approved
0.5686	Remote Similarity	NPD5208	Approved
0.5682	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD8035	Phase 2
0.5673	Remote Similarity	NPD8034	Phase 2
0.567	Remote Similarity	NPD7525	Registered
0.567	Remote Similarity	NPD4748	Discontinued
0.566	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5695	Phase 3
0.5638	Remote Similarity	NPD8264	Approved
0.5631	Remote Similarity	NPD5328	Approved
0.5631	Remote Similarity	NPD6673	Approved
0.5631	Remote Similarity	NPD6080	Approved
0.5631	Remote Similarity	NPD6904	Approved
0.5625	Remote Similarity	NPD6402	Approved
0.5625	Remote Similarity	NPD6675	Approved
0.5625	Remote Similarity	NPD5739	Approved
0.5625	Remote Similarity	NPD7128	Approved
0.5619	Remote Similarity	NPD5778	Approved
0.5619	Remote Similarity	NPD5779	Approved
0.56	Remote Similarity	NPD3665	Phase 1
0.56	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.56	Remote Similarity	NPD3666	Approved
0.56	Remote Similarity	NPD3133	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