NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	269.111
LogP:	3.627
LogD:	3.398
LogS:	-2.99
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.817
Synthetic Accessibility Score:	2.794
Fsp3:	0.6
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:	-4.385
MDCK Permeability:	1.6973246601992287e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.541
Plasma Protein Binding (PPB):	92.9470443725586%
Volume Distribution (VD):	3.425
Pgp-substrate:	10.183732032775879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.604
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.673
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.48
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.386
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.368
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	12.741
Half-life (T1/2):	0.422

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.616
Skin Sensitization:	0.248
Carcinogencity:	0.301
Eye Corrosion:	0.589
Eye Irritation:	0.973
Respiratory Toxicity:	0.307

Download Data

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

Natural Product: NPC72729

Natural Product ID:	NPC72729
*Common Name:**	(+)-Curcudiol
IUPAC Name:	2-[(2S)-6-hydroxy-6-methylheptan-2-yl]-5-methylphenol
Synonyms:	(+)-Curcudiol; (1S)-Curcudiol; (S)-(+)-Curcudiol
Standard InCHIKey:	TYUONEYWBLIYDF-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-11-7-8-13(14(16)10-11)12(2)6-5-9-15(3,4)17/h7-8,10,12,16-17H,5-6,9H2,1-4H3/t12-/m0/s1
SMILES:	Cc1ccc([C@@H](C)CCCC(C)(C)O)c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504569
PubChem CID:	184024
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
NPO26494	Didiscus oxeata	Species	Halichondriidae	Eukaryota	n.a.	Rio Bueno, Jamaica	n.a.	PMID[12444675]
NPO26494	Didiscus oxeata	Species	Halichondriidae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	250.0	ug.mL-1	PMID[524990]

☑ 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 NPC72729 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	251
0.1-0.2	1703
0.2-0.3	4102
0.3-0.4	13542
0.4-0.5	7014
0.5-0.6	10086
0.6-0.7	4559
0.7-0.8	1060
0.8-0.85	243
0.85-0.9	95
0.9-0.95	37
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9785	High Similarity	NPC79241
0.9785	High Similarity	NPC6597
0.9677	High Similarity	NPC259512
0.9677	High Similarity	NPC312132
0.9485	High Similarity	NPC475225
0.9474	High Similarity	NPC299762
0.9474	High Similarity	NPC33675
0.9394	High Similarity	NPC66834
0.9381	High Similarity	NPC235762
0.9381	High Similarity	NPC471228
0.9293	High Similarity	NPC53740
0.9293	High Similarity	NPC310456
0.9278	High Similarity	NPC252105
0.9247	High Similarity	NPC231150
0.9192	High Similarity	NPC47284
0.9175	High Similarity	NPC174911
0.9109	High Similarity	NPC306295
0.9082	High Similarity	NPC80800
0.9082	High Similarity	NPC477685
0.9053	High Similarity	NPC245187
0.9053	High Similarity	NPC152415
0.9	High Similarity	NPC117115
0.899	High Similarity	NPC108497
0.898	High Similarity	NPC248396
0.898	High Similarity	NPC48730
0.898	High Similarity	NPC129373
0.8969	High Similarity	NPC475078
0.8969	High Similarity	NPC77492
0.8969	High Similarity	NPC152097
0.8947	High Similarity	NPC162314
0.8947	High Similarity	NPC94139
0.8947	High Similarity	NPC210497
0.8947	High Similarity	NPC306884
0.8947	High Similarity	NPC147284
0.8947	High Similarity	NPC55903
0.8947	High Similarity	NPC3358
0.8942	High Similarity	NPC228452
0.8936	High Similarity	NPC192
0.8925	High Similarity	NPC27974
0.8922	High Similarity	NPC64586
0.8911	High Similarity	NPC21594
0.89	High Similarity	NPC272029
0.89	High Similarity	NPC227458
0.89	High Similarity	NPC218879
0.89	High Similarity	NPC475580
0.89	High Similarity	NPC244513
0.8889	High Similarity	NPC12221
0.8878	High Similarity	NPC260775
0.8846	High Similarity	NPC224527
0.8846	High Similarity	NPC54373
0.8846	High Similarity	NPC469912
0.8842	High Similarity	NPC306074
0.8842	High Similarity	NPC304541
0.8835	High Similarity	NPC58865
0.8835	High Similarity	NPC186385
0.8835	High Similarity	NPC299568
0.8824	High Similarity	NPC151477
0.8824	High Similarity	NPC320439
0.8824	High Similarity	NPC158253
0.8824	High Similarity	NPC204901
0.8824	High Similarity	NPC232523
0.8817	High Similarity	NPC307235
0.8817	High Similarity	NPC407
0.8812	High Similarity	NPC37802
0.88	High Similarity	NPC269212
0.8788	High Similarity	NPC130756
0.8788	High Similarity	NPC12931
0.8788	High Similarity	NPC70677
0.8776	High Similarity	NPC474073
0.8763	High Similarity	NPC222146
0.8763	High Similarity	NPC8392
0.875	High Similarity	NPC132720
0.875	High Similarity	NPC29373
0.8738	High Similarity	NPC174981
0.8725	High Similarity	NPC99836
0.8725	High Similarity	NPC12640
0.8725	High Similarity	NPC469913
0.8725	High Similarity	NPC201662
0.8713	High Similarity	NPC238696
0.871	High Similarity	NPC155393
0.8687	High Similarity	NPC252821
0.8687	High Similarity	NPC122005
0.8667	High Similarity	NPC77772
0.8667	High Similarity	NPC151537
0.8667	High Similarity	NPC266937
0.8667	High Similarity	NPC470770
0.866	High Similarity	NPC76938
0.866	High Similarity	NPC316301
0.866	High Similarity	NPC27323
0.866	High Similarity	NPC289769
0.8654	High Similarity	NPC19808
0.8654	High Similarity	NPC33728
0.8641	High Similarity	NPC474352
0.8632	High Similarity	NPC123273
0.8632	High Similarity	NPC242240
0.8632	High Similarity	NPC258219
0.8632	High Similarity	NPC318325
0.8602	High Similarity	NPC474211
0.8602	High Similarity	NPC286904
0.8602	High Similarity	NPC150837
0.86	High Similarity	NPC225506
0.8586	High Similarity	NPC156313
0.8585	High Similarity	NPC302371
0.8585	High Similarity	NPC26615
0.8585	High Similarity	NPC62867
0.8585	High Similarity	NPC46940
0.8585	High Similarity	NPC177962
0.8585	High Similarity	NPC250323
0.8571	High Similarity	NPC32714
0.8571	High Similarity	NPC274678
0.8558	High Similarity	NPC11554
0.8557	High Similarity	NPC271440
0.8544	High Similarity	NPC155072
0.8529	High Similarity	NPC323810
0.8526	High Similarity	NPC113460
0.8526	High Similarity	NPC19680
0.8526	High Similarity	NPC25493
0.8519	High Similarity	NPC469719
0.8519	High Similarity	NPC246760
0.8519	High Similarity	NPC84999
0.8505	High Similarity	NPC23804
0.8505	High Similarity	NPC190212
0.8505	High Similarity	NPC319803
0.8505	High Similarity	NPC715
0.85	High Similarity	NPC128723
0.85	High Similarity	NPC92730
0.8495	Intermediate Similarity	NPC474354
0.8491	Intermediate Similarity	NPC95716
0.8491	Intermediate Similarity	NPC176279
0.8491	Intermediate Similarity	NPC260323
0.8485	Intermediate Similarity	NPC292730
0.8485	Intermediate Similarity	NPC82664
0.8485	Intermediate Similarity	NPC473388
0.8485	Intermediate Similarity	NPC132271
0.8485	Intermediate Similarity	NPC216520
0.8476	Intermediate Similarity	NPC473524
0.8469	Intermediate Similarity	NPC128062
0.8454	Intermediate Similarity	NPC204210
0.8454	Intermediate Similarity	NPC155908
0.8447	Intermediate Similarity	NPC471350
0.8447	Intermediate Similarity	NPC138942
0.844	Intermediate Similarity	NPC471668
0.844	Intermediate Similarity	NPC141001
0.8438	Intermediate Similarity	NPC280347
0.8438	Intermediate Similarity	NPC177420
0.8431	Intermediate Similarity	NPC24404
0.8431	Intermediate Similarity	NPC168829
0.8431	Intermediate Similarity	NPC313030
0.8431	Intermediate Similarity	NPC106396
0.8431	Intermediate Similarity	NPC168393
0.8431	Intermediate Similarity	NPC242342
0.8431	Intermediate Similarity	NPC24327
0.8431	Intermediate Similarity	NPC71002
0.8431	Intermediate Similarity	NPC302219
0.8431	Intermediate Similarity	NPC222522
0.8431	Intermediate Similarity	NPC249828
0.8431	Intermediate Similarity	NPC85479
0.8431	Intermediate Similarity	NPC12870
0.8431	Intermediate Similarity	NPC146798
0.8431	Intermediate Similarity	NPC53051
0.8431	Intermediate Similarity	NPC94351
0.8431	Intermediate Similarity	NPC168303
0.8431	Intermediate Similarity	NPC233827
0.8426	Intermediate Similarity	NPC195922
0.8426	Intermediate Similarity	NPC471534
0.8421	Intermediate Similarity	NPC23167
0.8416	Intermediate Similarity	NPC10588
0.8416	Intermediate Similarity	NPC211885
0.8416	Intermediate Similarity	NPC294741
0.8416	Intermediate Similarity	NPC130103
0.8416	Intermediate Similarity	NPC166761
0.8411	Intermediate Similarity	NPC471179
0.8411	Intermediate Similarity	NPC166995
0.84	Intermediate Similarity	NPC225464
0.8396	Intermediate Similarity	NPC296683
0.8396	Intermediate Similarity	NPC141782
0.8396	Intermediate Similarity	NPC13482
0.8396	Intermediate Similarity	NPC224870
0.8387	Intermediate Similarity	NPC168855
0.8384	Intermediate Similarity	NPC144682
0.8384	Intermediate Similarity	NPC26244
0.8378	Intermediate Similarity	NPC160235
0.8378	Intermediate Similarity	NPC151197
0.8365	Intermediate Similarity	NPC271274
0.8365	Intermediate Similarity	NPC477814
0.8365	Intermediate Similarity	NPC54765
0.8364	Intermediate Similarity	NPC320864
0.8364	Intermediate Similarity	NPC477136
0.8351	Intermediate Similarity	NPC55561
0.8351	Intermediate Similarity	NPC312304
0.835	Intermediate Similarity	NPC102216
0.835	Intermediate Similarity	NPC120719
0.835	Intermediate Similarity	NPC288411
0.8349	Intermediate Similarity	NPC35797
0.8349	Intermediate Similarity	NPC192948
0.8333	Intermediate Similarity	NPC192032
0.8333	Intermediate Similarity	NPC1793
0.8333	Intermediate Similarity	NPC137415
0.8333	Intermediate Similarity	NPC166313
0.8333	Intermediate Similarity	NPC284011

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 NPC72729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	1061
0.2-0.3	1312
0.3-0.4	2908
0.4-0.5	1921
0.5-0.6	1157
0.6-0.7	444
0.7-0.8	76
0.8-0.85	13
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9677	High Similarity	NPD288	Approved
0.957	High Similarity	NPD844	Approved
0.898	High Similarity	NPD289	Clinical (unspecified phase)
0.8947	High Similarity	NPD845	Approved
0.8835	High Similarity	NPD4750	Phase 3
0.8687	High Similarity	NPD3020	Approved
0.866	High Similarity	NPD1432	Clinical (unspecified phase)
0.8585	High Similarity	NPD7635	Approved
0.8384	Intermediate Similarity	NPD2859	Approved
0.8384	Intermediate Similarity	NPD2860	Approved
0.8384	Intermediate Similarity	NPD1809	Phase 2
0.8365	Intermediate Similarity	NPD1445	Approved
0.8365	Intermediate Similarity	NPD1444	Approved
0.8333	Intermediate Similarity	NPD940	Approved
0.8333	Intermediate Similarity	NPD846	Approved
0.8302	Intermediate Similarity	NPD3022	Approved
0.8302	Intermediate Similarity	NPD3021	Approved
0.8286	Intermediate Similarity	NPD2342	Discontinued
0.8283	Intermediate Similarity	NPD2933	Approved
0.8283	Intermediate Similarity	NPD2934	Approved
0.8131	Intermediate Similarity	NPD1792	Phase 2
0.8105	Intermediate Similarity	NPD111	Approved
0.8018	Intermediate Similarity	NPD6671	Approved
0.7863	Intermediate Similarity	NPD4749	Approved
0.7838	Intermediate Similarity	NPD2228	Approved
0.7838	Intermediate Similarity	NPD2234	Approved
0.7838	Intermediate Similarity	NPD2229	Approved
0.7826	Intermediate Similarity	NPD4059	Approved
0.7807	Intermediate Similarity	NPD3091	Approved
0.7714	Intermediate Similarity	NPD1242	Phase 1
0.7672	Intermediate Similarity	NPD4626	Approved
0.7672	Intermediate Similarity	NPD2932	Approved
0.7672	Intermediate Similarity	NPD3019	Approved
0.7632	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD1791	Approved
0.7611	Intermediate Similarity	NPD497	Approved
0.7611	Intermediate Similarity	NPD1793	Approved
0.757	Intermediate Similarity	NPD9500	Approved
0.7563	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3092	Approved
0.7524	Intermediate Similarity	NPD9273	Approved
0.7522	Intermediate Similarity	NPD495	Approved
0.7522	Intermediate Similarity	NPD1398	Phase 1
0.7522	Intermediate Similarity	NPD498	Approved
0.7522	Intermediate Similarity	NPD496	Approved
0.7521	Intermediate Similarity	NPD1751	Approved
0.75	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD6696	Suspended
0.75	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD4625	Phase 3
0.7479	Intermediate Similarity	NPD2232	Approved
0.7479	Intermediate Similarity	NPD2230	Approved
0.7479	Intermediate Similarity	NPD2233	Approved
0.7478	Intermediate Similarity	NPD7340	Approved
0.7456	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4093	Discontinued
0.7419	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD1201	Approved
0.7395	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2286	Discontinued
0.7373	Intermediate Similarity	NPD3095	Discontinued
0.7368	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5304	Approved
0.735	Intermediate Similarity	NPD5303	Approved
0.7339	Intermediate Similarity	NPD9610	Approved
0.7339	Intermediate Similarity	NPD9608	Approved
0.7328	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD9087	Approved
0.7304	Intermediate Similarity	NPD9614	Approved
0.7304	Intermediate Similarity	NPD9618	Approved
0.7295	Intermediate Similarity	NPD3094	Phase 2
0.7288	Intermediate Similarity	NPD5691	Approved
0.7281	Intermediate Similarity	NPD9379	Approved
0.7281	Intermediate Similarity	NPD9377	Approved
0.7248	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD709	Approved
0.7227	Intermediate Similarity	NPD1778	Approved
0.7227	Intermediate Similarity	NPD4589	Approved
0.7222	Intermediate Similarity	NPD1616	Discontinued
0.7222	Intermediate Similarity	NPD3028	Approved
0.7217	Intermediate Similarity	NPD5283	Phase 1
0.7188	Intermediate Similarity	NPD9088	Approved
0.7177	Intermediate Similarity	NPD2861	Phase 2
0.7177	Intermediate Similarity	NPD5736	Approved
0.7167	Intermediate Similarity	NPD1980	Approved
0.7167	Intermediate Similarity	NPD1981	Approved
0.7167	Intermediate Similarity	NPD1983	Approved
0.7157	Intermediate Similarity	NPD1101	Approved
0.7155	Intermediate Similarity	NPD475	Phase 2
0.7154	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD290	Approved
0.7131	Intermediate Similarity	NPD1755	Approved
0.713	Intermediate Similarity	NPD1138	Approved
0.7119	Intermediate Similarity	NPD9615	Approved
0.7119	Intermediate Similarity	NPD9616	Approved
0.7119	Intermediate Similarity	NPD9613	Approved
0.7107	Intermediate Similarity	NPD1610	Phase 2
0.7097	Intermediate Similarity	NPD4624	Approved
0.7097	Intermediate Similarity	NPD2194	Approved
0.7097	Intermediate Similarity	NPD2195	Approved
0.7083	Intermediate Similarity	NPD2667	Approved
0.7083	Intermediate Similarity	NPD9294	Approved
0.7083	Intermediate Similarity	NPD2668	Approved
0.708	Intermediate Similarity	NPD2684	Approved
0.7073	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD316	Approved
0.7059	Intermediate Similarity	NPD7330	Discontinued
0.7054	Intermediate Similarity	NPD4097	Suspended
0.7054	Intermediate Similarity	NPD968	Approved
0.7043	Intermediate Similarity	NPD1139	Approved
0.7043	Intermediate Similarity	NPD1137	Approved
0.704	Intermediate Similarity	NPD1712	Approved
0.704	Intermediate Similarity	NPD3636	Approved
0.704	Intermediate Similarity	NPD3635	Approved
0.704	Intermediate Similarity	NPD3637	Approved
0.7031	Intermediate Similarity	NPD4060	Phase 1
0.7025	Intermediate Similarity	NPD3496	Discontinued
0.7025	Intermediate Similarity	NPD3023	Approved
0.7025	Intermediate Similarity	NPD3026	Approved
0.7023	Intermediate Similarity	NPD6100	Approved
0.7023	Intermediate Similarity	NPD6099	Approved
0.7019	Intermediate Similarity	NPD1090	Approved
0.7019	Intermediate Similarity	NPD1086	Approved
0.7019	Intermediate Similarity	NPD1089	Approved
0.7018	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3024	Approved
0.7	Intermediate Similarity	NPD3025	Approved
0.7	Intermediate Similarity	NPD4817	Approved
0.7	Intermediate Similarity	NPD4818	Approved
0.6984	Remote Similarity	NPD2606	Approved
0.6984	Remote Similarity	NPD4908	Phase 1
0.6984	Remote Similarity	NPD2605	Approved
0.6967	Remote Similarity	NPD1611	Approved
0.6957	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6663	Approved
0.6949	Remote Similarity	NPD255	Approved
0.6949	Remote Similarity	NPD256	Approved
0.6949	Remote Similarity	NPD7157	Approved
0.6947	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.693	Remote Similarity	NPD9266	Approved
0.693	Remote Similarity	NPD74	Approved
0.6929	Remote Similarity	NPD5156	Approved
0.6929	Remote Similarity	NPD5155	Approved
0.6923	Remote Similarity	NPD800	Approved
0.6917	Remote Similarity	NPD1759	Phase 1
0.6916	Remote Similarity	NPD1693	Approved
0.6911	Remote Similarity	NPD1608	Approved
0.69	Remote Similarity	NPD9089	Approved
0.6899	Remote Similarity	NPD2238	Phase 2
0.6891	Remote Similarity	NPD9493	Approved
0.6891	Remote Similarity	NPD7636	Approved
0.6887	Remote Similarity	NPD1088	Approved
0.6885	Remote Similarity	NPD3143	Discontinued
0.688	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3594	Approved
0.685	Remote Similarity	NPD3595	Approved
0.6842	Remote Similarity	NPD9267	Approved
0.6842	Remote Similarity	NPD9263	Approved
0.6842	Remote Similarity	NPD9264	Approved
0.6838	Remote Similarity	NPD821	Approved
0.6838	Remote Similarity	NPD7843	Approved
0.6833	Remote Similarity	NPD16	Approved
0.6833	Remote Similarity	NPD856	Approved
0.6833	Remote Similarity	NPD1758	Phase 1
0.6829	Remote Similarity	NPD1281	Approved
0.6825	Remote Similarity	NPD6584	Phase 3
0.6822	Remote Similarity	NPD1409	Phase 3
0.6815	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6387	Discontinued
0.6803	Remote Similarity	NPD9381	Approved
0.6803	Remote Similarity	NPD9384	Approved
0.68	Remote Similarity	NPD9093	Approved
0.6791	Remote Similarity	NPD4257	Approved
0.6791	Remote Similarity	NPD4256	Phase 2
0.6786	Remote Similarity	NPD3682	Approved
0.6786	Remote Similarity	NPD3681	Approved
0.6786	Remote Similarity	NPD3683	Approved
0.6786	Remote Similarity	NPD4231	Approved
0.6786	Remote Similarity	NPD4229	Approved
0.6786	Remote Similarity	NPD3680	Approved
0.678	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1548	Phase 1
0.6774	Remote Similarity	NPD2235	Phase 2
0.6774	Remote Similarity	NPD3070	Discontinued
0.6774	Remote Similarity	NPD2231	Phase 2
0.6772	Remote Similarity	NPD2237	Approved
0.6769	Remote Similarity	NPD6346	Approved
0.6769	Remote Similarity	NPD3620	Phase 2
0.6769	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD9295	Approved
0.6748	Remote Similarity	NPD2688	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