NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.19
Volume:	315.726
LogP:	3.372
LogD:	3.472
LogS:	-3.734
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.875
Synthetic Accessibility Score:	3.126
Fsp3:	0.444
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:	-4.425
MDCK Permeability:	1.5025695574877318e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874
Plasma Protein Binding (PPB):	87.8036880493164%
Volume Distribution (VD):	0.671
Pgp-substrate:	20.910755157470703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.573
CYP1A2-substrate:	0.549
CYP2C19-inhibitor:	0.452
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.319
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.645
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.5

ADMET: Excretion

Clearance (CL):	9.172
Half-life (T1/2):	0.283

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.512
Drug-inuced Liver Injury (DILI):	0.321
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.129
Carcinogencity:	0.915
Eye Corrosion:	0.037
Eye Irritation:	0.991
Respiratory Toxicity:	0.003

Download Data

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

Natural Product: NPC242628

Natural Product ID:	NPC242628
*Common Name:**	(3E,3'e)-4,4'-(3,6-Dimethyl-1,2-Phenylene)Bis(2-Methylbut-3-En-2-Ol)
IUPAC Name:	(E)-4-[2-[(E)-3-hydroxy-3-methylbut-1-enyl]-3,6-dimethylphenyl]-2-methylbut-3-en-2-ol
Synonyms:
Standard InCHIKey:	HMHFCIOLAIQIJJ-WGDLNXRISA-N
Standard InCHI:	InChI=1S/C18H26O2/c1-13-7-8-14(2)16(10-12-18(5,6)20)15(13)9-11-17(3,4)19/h7-12,19-20H,1-6H3/b11-9+,12-10+
SMILES:	CC(/C=C/c1c(C)ccc(c1/C=C/C(O)(C)C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2376609
PubChem CID:	71600584
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002754] Cinnamyl alcohols

*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
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23548547]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25497963]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	4

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>=	100000.0	nM	PMID[564882]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>=	100000.0	nM	PMID[564882]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC80	>=	64.0	ug.mL-1	PMID[564882]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC80	=	64.0	ug.mL-1	PMID[564882]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC80	=	64.0	ug.mL-1	PMID[564882]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC80	=	64.0	ug.mL-1	PMID[564882]

☑ 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 NPC242628 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	170
0.1-0.2	2089
0.2-0.3	5761
0.3-0.4	16865
0.4-0.5	13136
0.5-0.6	3609
0.6-0.7	901
0.7-0.8	151
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8488	Intermediate Similarity	NPC26224
0.8434	Intermediate Similarity	NPC267704
0.8267	Intermediate Similarity	NPC6107
0.8235	Intermediate Similarity	NPC474211
0.8205	Intermediate Similarity	NPC54269
0.8133	Intermediate Similarity	NPC113837
0.8133	Intermediate Similarity	NPC289915
0.8118	Intermediate Similarity	NPC474354
0.8	Intermediate Similarity	NPC168855
0.7955	Intermediate Similarity	NPC1793
0.7895	Intermediate Similarity	NPC19856
0.7889	Intermediate Similarity	NPC314690
0.7872	Intermediate Similarity	NPC469481
0.7857	Intermediate Similarity	NPC133050
0.7848	Intermediate Similarity	NPC135433
0.7848	Intermediate Similarity	NPC1008
0.7848	Intermediate Similarity	NPC226999
0.7848	Intermediate Similarity	NPC87099
0.7848	Intermediate Similarity	NPC158028
0.7848	Intermediate Similarity	NPC280135
0.7848	Intermediate Similarity	NPC39799
0.7848	Intermediate Similarity	NPC193578
0.7831	Intermediate Similarity	NPC469894
0.7816	Intermediate Similarity	NPC243166
0.7812	Intermediate Similarity	NPC472222
0.7812	Intermediate Similarity	NPC472221
0.7805	Intermediate Similarity	NPC249018
0.7805	Intermediate Similarity	NPC3190
0.7763	Intermediate Similarity	NPC32312
0.7763	Intermediate Similarity	NPC155172
0.7763	Intermediate Similarity	NPC198023
0.7738	Intermediate Similarity	NPC328178
0.7732	Intermediate Similarity	NPC471133
0.7711	Intermediate Similarity	NPC50192
0.7701	Intermediate Similarity	NPC3210
0.7692	Intermediate Similarity	NPC78954
0.7692	Intermediate Similarity	NPC239931
0.7692	Intermediate Similarity	NPC82770
0.7662	Intermediate Similarity	NPC178527
0.7632	Intermediate Similarity	NPC88566
0.7632	Intermediate Similarity	NPC45756
0.7629	Intermediate Similarity	NPC315794
0.7619	Intermediate Similarity	NPC159661
0.76	Intermediate Similarity	NPC150196
0.76	Intermediate Similarity	NPC310758
0.76	Intermediate Similarity	NPC54368
0.76	Intermediate Similarity	NPC238023
0.76	Intermediate Similarity	NPC210849
0.76	Intermediate Similarity	NPC248705
0.7595	Intermediate Similarity	NPC139416
0.7595	Intermediate Similarity	NPC213570
0.7595	Intermediate Similarity	NPC246822
0.7586	Intermediate Similarity	NPC95429
0.7582	Intermediate Similarity	NPC220596
0.7576	Intermediate Similarity	NPC27252
0.7576	Intermediate Similarity	NPC472980
0.7576	Intermediate Similarity	NPC472979
0.7561	Intermediate Similarity	NPC307195
0.7561	Intermediate Similarity	NPC189371
0.7556	Intermediate Similarity	NPC298115
0.7529	Intermediate Similarity	NPC315216
0.75	Intermediate Similarity	NPC153885
0.75	Intermediate Similarity	NPC289117
0.75	Intermediate Similarity	NPC99482
0.75	Intermediate Similarity	NPC103488
0.75	Intermediate Similarity	NPC155232
0.75	Intermediate Similarity	NPC225079
0.75	Intermediate Similarity	NPC128645
0.7471	Intermediate Similarity	NPC172984
0.7471	Intermediate Similarity	NPC477770
0.747	Intermediate Similarity	NPC110264
0.7467	Intermediate Similarity	NPC147062
0.7439	Intermediate Similarity	NPC96835
0.7439	Intermediate Similarity	NPC258492
0.7419	Intermediate Similarity	NPC238219
0.7416	Intermediate Similarity	NPC160339
0.7416	Intermediate Similarity	NPC307
0.7416	Intermediate Similarity	NPC93843
0.7391	Intermediate Similarity	NPC133461
0.7386	Intermediate Similarity	NPC304538
0.7374	Intermediate Similarity	NPC243601
0.7368	Intermediate Similarity	NPC135924
0.7368	Intermediate Similarity	NPC251579
0.7368	Intermediate Similarity	NPC133135
0.7368	Intermediate Similarity	NPC324602
0.7363	Intermediate Similarity	NPC199567
0.7356	Intermediate Similarity	NPC475199
0.7356	Intermediate Similarity	NPC14326
0.7356	Intermediate Similarity	NPC283012
0.7353	Intermediate Similarity	NPC95126
0.7353	Intermediate Similarity	NPC133308
0.7353	Intermediate Similarity	NPC475002
0.7349	Intermediate Similarity	NPC32203
0.7349	Intermediate Similarity	NPC206800
0.7347	Intermediate Similarity	NPC247976
0.7342	Intermediate Similarity	NPC267443
0.734	Intermediate Similarity	NPC260233
0.7333	Intermediate Similarity	NPC8235
0.7333	Intermediate Similarity	NPC64270
0.7327	Intermediate Similarity	NPC472982
0.7327	Intermediate Similarity	NPC149455
0.7327	Intermediate Similarity	NPC64642
0.7326	Intermediate Similarity	NPC285716
0.7326	Intermediate Similarity	NPC17408
0.7303	Intermediate Similarity	NPC123476
0.7294	Intermediate Similarity	NPC245896
0.7294	Intermediate Similarity	NPC66270
0.7284	Intermediate Similarity	NPC72670
0.7284	Intermediate Similarity	NPC251490
0.7283	Intermediate Similarity	NPC173413
0.7273	Intermediate Similarity	NPC71009
0.7273	Intermediate Similarity	NPC29680
0.7273	Intermediate Similarity	NPC66517
0.7204	Intermediate Similarity	NPC79917
0.7204	Intermediate Similarity	NPC125226
0.7204	Intermediate Similarity	NPC475023
0.7204	Intermediate Similarity	NPC284475
0.7204	Intermediate Similarity	NPC475059
0.72	Intermediate Similarity	NPC300345
0.72	Intermediate Similarity	NPC120441
0.72	Intermediate Similarity	NPC212114
0.72	Intermediate Similarity	NPC65873
0.72	Intermediate Similarity	NPC117115
0.7188	Intermediate Similarity	NPC239185
0.7184	Intermediate Similarity	NPC474057
0.7179	Intermediate Similarity	NPC21211
0.7159	Intermediate Similarity	NPC99394
0.7159	Intermediate Similarity	NPC103326
0.7159	Intermediate Similarity	NPC329319
0.7159	Intermediate Similarity	NPC73637
0.7159	Intermediate Similarity	NPC87299
0.7159	Intermediate Similarity	NPC121478
0.7158	Intermediate Similarity	NPC289769
0.7143	Intermediate Similarity	NPC136810
0.7143	Intermediate Similarity	NPC133809
0.7143	Intermediate Similarity	NPC72729
0.7143	Intermediate Similarity	NPC128248
0.7129	Intermediate Similarity	NPC100767
0.7128	Intermediate Similarity	NPC475057
0.7128	Intermediate Similarity	NPC188844
0.7128	Intermediate Similarity	NPC59677
0.7128	Intermediate Similarity	NPC1682
0.7128	Intermediate Similarity	NPC323420
0.7126	Intermediate Similarity	NPC184030
0.7126	Intermediate Similarity	NPC164449
0.7126	Intermediate Similarity	NPC157055
0.7126	Intermediate Similarity	NPC50063
0.7115	Intermediate Similarity	NPC469912
0.7115	Intermediate Similarity	NPC471188
0.7115	Intermediate Similarity	NPC111108
0.7113	Intermediate Similarity	NPC134882
0.7113	Intermediate Similarity	NPC75724
0.7113	Intermediate Similarity	NPC49994
0.7108	Intermediate Similarity	NPC1901
0.71	Intermediate Similarity	NPC238696
0.71	Intermediate Similarity	NPC272029
0.7097	Intermediate Similarity	NPC277277
0.7093	Intermediate Similarity	NPC224544
0.7089	Intermediate Similarity	NPC291066
0.7083	Intermediate Similarity	NPC185208
0.7083	Intermediate Similarity	NPC219573
0.7075	Intermediate Similarity	NPC93181
0.7067	Intermediate Similarity	NPC269586
0.7067	Intermediate Similarity	NPC198841
0.7065	Intermediate Similarity	NPC153308
0.7065	Intermediate Similarity	NPC157778
0.7059	Intermediate Similarity	NPC151477
0.7053	Intermediate Similarity	NPC289883
0.7051	Intermediate Similarity	NPC22786
0.7048	Intermediate Similarity	NPC302371
0.7048	Intermediate Similarity	NPC46940
0.7045	Intermediate Similarity	NPC117180
0.7037	Intermediate Similarity	NPC311343
0.7033	Intermediate Similarity	NPC164526
0.703	Intermediate Similarity	NPC471186
0.7019	Intermediate Similarity	NPC132720
0.7011	Intermediate Similarity	NPC272260
0.701	Intermediate Similarity	NPC265220
0.701	Intermediate Similarity	NPC226041
0.7009	Intermediate Similarity	NPC469719
0.7	Intermediate Similarity	NPC108497
0.699	Remote Similarity	NPC475006
0.699	Remote Similarity	NPC11554
0.6988	Remote Similarity	NPC208302
0.6988	Remote Similarity	NPC155429
0.6988	Remote Similarity	NPC74458
0.6977	Remote Similarity	NPC9796
0.697	Remote Similarity	NPC225506
0.697	Remote Similarity	NPC211885
0.697	Remote Similarity	NPC109514
0.697	Remote Similarity	NPC476993
0.6966	Remote Similarity	NPC230068
0.6962	Remote Similarity	NPC113670
0.6961	Remote Similarity	NPC21594
0.6961	Remote Similarity	NPC53740
0.6957	Remote Similarity	NPC60408
0.6957	Remote Similarity	NPC194326
0.6957	Remote Similarity	NPC69057
0.6957	Remote Similarity	NPC473031
0.6957	Remote Similarity	NPC43945

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 NPC242628 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1228
0.2-0.3	1633
0.3-0.4	3334
0.4-0.5	1845
0.5-0.6	788
0.6-0.7	145
0.7-0.8	7
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8118	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD6049	Phase 2
0.8095	Intermediate Similarity	NPD3971	Phase 1
0.7526	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD9716	Approved
0.7234	Intermediate Similarity	NPD845	Approved
0.7204	Intermediate Similarity	NPD7609	Phase 3
0.7188	Intermediate Similarity	NPD3495	Discontinued
0.7128	Intermediate Similarity	NPD7631	Approved
0.7065	Intermediate Similarity	NPD1101	Approved
0.7048	Intermediate Similarity	NPD7635	Approved
0.6962	Remote Similarity	NPD675	Discontinued
0.6957	Remote Similarity	NPD650	Approved
0.6915	Remote Similarity	NPD1086	Approved
0.6915	Remote Similarity	NPD1089	Approved
0.6915	Remote Similarity	NPD1090	Approved
0.6907	Remote Similarity	NPD3093	Approved
0.6907	Remote Similarity	NPD1809	Phase 2
0.6907	Remote Similarity	NPD2859	Approved
0.6907	Remote Similarity	NPD2860	Approved
0.6907	Remote Similarity	NPD844	Approved
0.6893	Remote Similarity	NPD2342	Discontinued
0.6869	Remote Similarity	NPD3020	Approved
0.6857	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3099	Discontinued
0.6837	Remote Similarity	NPD288	Approved
0.6822	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4544	Approved
0.6809	Remote Similarity	NPD800	Approved
0.6804	Remote Similarity	NPD2933	Approved
0.6804	Remote Similarity	NPD1693	Approved
0.6804	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4814	Discontinued
0.6804	Remote Similarity	NPD2934	Approved
0.68	Remote Similarity	NPD1616	Discontinued
0.6782	Remote Similarity	NPD9294	Approved
0.6774	Remote Similarity	NPD1087	Approved
0.6771	Remote Similarity	NPD1088	Approved
0.6759	Remote Similarity	NPD5951	Approved
0.6742	Remote Similarity	NPD3979	Approved
0.6742	Remote Similarity	NPD3903	Approved
0.6742	Remote Similarity	NPD3981	Approved
0.6742	Remote Similarity	NPD3904	Approved
0.6735	Remote Similarity	NPD2895	Discontinued
0.6733	Remote Similarity	NPD4818	Approved
0.6733	Remote Similarity	NPD4817	Approved
0.6701	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3719	Approved
0.6701	Remote Similarity	NPD1409	Phase 3
0.6701	Remote Similarity	NPD3718	Approved
0.67	Remote Similarity	NPD2066	Phase 3
0.6667	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5346	Phase 2
0.6632	Remote Similarity	NPD5347	Phase 2
0.6602	Remote Similarity	NPD5909	Discontinued
0.6602	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4793	Discontinued
0.6559	Remote Similarity	NPD111	Approved
0.6549	Remote Similarity	NPD4626	Approved
0.6548	Remote Similarity	NPD1673	Approved
0.6545	Remote Similarity	NPD3317	Approved
0.6522	Remote Similarity	NPD4635	Approved
0.6518	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3680	Approved
0.6505	Remote Similarity	NPD4229	Approved
0.6505	Remote Similarity	NPD3681	Approved
0.6505	Remote Similarity	NPD4658	Approved
0.6505	Remote Similarity	NPD3682	Approved
0.6505	Remote Similarity	NPD4656	Approved
0.6505	Remote Similarity	NPD6647	Phase 2
0.6505	Remote Similarity	NPD4231	Approved
0.6505	Remote Similarity	NPD3683	Approved
0.6495	Remote Similarity	NPD1239	Approved
0.6484	Remote Similarity	NPD226	Approved
0.6471	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6354	Discontinued
0.6463	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3429	Approved
0.6452	Remote Similarity	NPD3427	Approved
0.6449	Remote Similarity	NPD4750	Phase 3
0.6408	Remote Similarity	NPD846	Approved
0.6408	Remote Similarity	NPD940	Approved
0.6404	Remote Similarity	NPD4059	Approved
0.6404	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5126	Approved
0.6404	Remote Similarity	NPD5125	Phase 3
0.64	Remote Similarity	NPD1989	Approved
0.6395	Remote Similarity	NPD292	Approved
0.6395	Remote Similarity	NPD294	Approved
0.6392	Remote Similarity	NPD3673	Approved
0.6392	Remote Similarity	NPD3672	Approved
0.6381	Remote Similarity	NPD5048	Discontinued
0.6374	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7741	Discontinued
0.6372	Remote Similarity	NPD3091	Approved
0.6364	Remote Similarity	NPD6010	Discontinued
0.6354	Remote Similarity	NPD531	Approved
0.6346	Remote Similarity	NPD1929	Approved
0.6346	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5103	Approved
0.6346	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1930	Approved
0.6344	Remote Similarity	NPD4000	Phase 3
0.6344	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD9491	Approved
0.6337	Remote Similarity	NPD1565	Approved
0.6337	Remote Similarity	NPD5597	Approved
0.6337	Remote Similarity	NPD1564	Approved
0.6337	Remote Similarity	NPD5598	Approved
0.6337	Remote Similarity	NPD1566	Phase 3
0.6333	Remote Similarity	NPD225	Approved
0.6333	Remote Similarity	NPD227	Approved
0.633	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD530	Approved
0.6316	Remote Similarity	NPD1710	Approved
0.6316	Remote Similarity	NPD4406	Approved
0.6316	Remote Similarity	NPD4409	Approved
0.6306	Remote Similarity	NPD497	Approved
0.6304	Remote Similarity	NPD942	Approved
0.6304	Remote Similarity	NPD3035	Approved
0.63	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3021	Approved
0.6296	Remote Similarity	NPD3022	Approved
0.6289	Remote Similarity	NPD689	Discontinued
0.6286	Remote Similarity	NPD3046	Approved
0.6286	Remote Similarity	NPD3047	Approved
0.6286	Remote Similarity	NPD3048	Approved
0.6275	Remote Similarity	NPD4813	Approved
0.6275	Remote Similarity	NPD4263	Approved
0.6263	Remote Similarity	NPD4405	Approved
0.6263	Remote Similarity	NPD4408	Approved
0.6263	Remote Similarity	NPD1508	Approved
0.6263	Remote Similarity	NPD752	Approved
0.6263	Remote Similarity	NPD4407	Approved
0.6262	Remote Similarity	NPD6406	Approved
0.6261	Remote Similarity	NPD3019	Approved
0.6261	Remote Similarity	NPD2932	Approved
0.6261	Remote Similarity	NPD2286	Discontinued
0.625	Remote Similarity	NPD1282	Approved
0.625	Remote Similarity	NPD3428	Approved
0.625	Remote Similarity	NPD3426	Approved
0.625	Remote Similarity	NPD1932	Approved
0.625	Remote Similarity	NPD4198	Discontinued
0.6239	Remote Similarity	NPD4254	Approved
0.6239	Remote Similarity	NPD4253	Approved
0.6238	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4170	Approved
0.6237	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4169	Approved
0.6222	Remote Similarity	NPD4144	Approved
0.6222	Remote Similarity	NPD4147	Approved
0.6216	Remote Similarity	NPD2234	Approved
0.6216	Remote Similarity	NPD495	Approved
0.6216	Remote Similarity	NPD2229	Approved
0.6216	Remote Similarity	NPD498	Approved
0.6216	Remote Similarity	NPD496	Approved
0.6216	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2228	Approved
0.6204	Remote Similarity	NPD4720	Approved
0.6204	Remote Similarity	NPD4718	Approved
0.6204	Remote Similarity	NPD4717	Approved
0.62	Remote Similarity	NPD1563	Approved
0.62	Remote Similarity	NPD720	Approved
0.62	Remote Similarity	NPD3980	Approved
0.62	Remote Similarity	NPD2878	Approved
0.62	Remote Similarity	NPD4542	Approved
0.62	Remote Similarity	NPD719	Approved
0.62	Remote Similarity	NPD4545	Approved
0.62	Remote Similarity	NPD3982	Approved
0.6186	Remote Similarity	NPD3345	Approved
0.6182	Remote Similarity	NPD2499	Approved
0.6182	Remote Similarity	NPD2500	Approved
0.6174	Remote Similarity	NPD5691	Approved
0.617	Remote Similarity	NPD2001	Discontinued
0.6168	Remote Similarity	NPD1444	Approved
0.6168	Remote Similarity	NPD1445	Approved
0.6154	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3092	Approved
0.6154	Remote Similarity	NPD3028	Approved
0.6148	Remote Similarity	NPD4625	Phase 3
0.6147	Remote Similarity	NPD1792	Phase 2
0.614	Remote Similarity	NPD7610	Discontinued
0.6139	Remote Similarity	NPD4094	Approved
0.6134	Remote Similarity	NPD6696	Suspended
0.6129	Remote Similarity	NPD4027	Approved
0.6129	Remote Similarity	NPD4026	Approved
0.6129	Remote Similarity	NPD9250	Approved
0.6122	Remote Similarity	NPD1629	Approved
0.6122	Remote Similarity	NPD1628	Approved
0.6121	Remote Similarity	NPD3095	Discontinued
0.6121	Remote Similarity	NPD7725	Approved
0.6117	Remote Similarity	NPD9611	Approved
0.6117	Remote Similarity	NPD5832	Phase 3
0.6117	Remote Similarity	NPD9495	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