NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.17
Volume:	248.582
LogP:	1.808
LogD:	2.202
LogS:	-2.242
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	4.63
Fsp3:	0.846
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.74
MDCK Permeability:	0.00012562905612867326
Pgp-inhibitor:	0.0
Pgp-substrate:	0.067
Human Intestinal Absorption (HIA):	0.816
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.607

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	80.0923843383789%
Volume Distribution (VD):	1.092
Pgp-substrate:	17.591123580932617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.556
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.343
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	5.864
Half-life (T1/2):	0.565

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.638
Maximum Recommended Daily Dose:	0.664
Skin Sensitization:	0.122
Carcinogencity:	0.299
Eye Corrosion:	0.006
Eye Irritation:	0.053
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC471268

Natural Product ID:	NPC471268
*Common Name:**	Wilsonol E
IUPAC Name:	(1S,2S,3S,4S)-4-[(E)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohexane-1,2-diol
Synonyms:
Standard InCHIKey:	PWZNHPDBFAQVDX-OAQVEFGHSA-N
Standard InCHI:	InChI=1S/C13H24O3/c1-8(14)5-6-10-9(2)12(16)11(15)7-13(10,3)4/h5-6,8-12,14-16H,7H2,1-4H3/b6-5+/t8?,9-,10-,11-,12-/m0/s1
SMILES:	CC(/C=C/[C@H]1[C@H](C)[C@H](O)[C@H](CC1(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2407695
PubChem CID:	73346006
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
NPO32875	cinnamomum wilsonii	Species	Lauraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23822611]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[569209]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[569209]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[569209]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[569209]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[569209]

☑ 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 NPC471268 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	160
0.1-0.2	1412
0.2-0.3	5745
0.3-0.4	15677
0.4-0.5	10356
0.5-0.6	6508
0.6-0.7	2289
0.7-0.8	491
0.8-0.85	45
0.85-0.9	10
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471271
0.9254	High Similarity	NPC471238
0.913	High Similarity	NPC471272
0.8919	High Similarity	NPC95124
0.8919	High Similarity	NPC471266
0.8857	High Similarity	NPC477792
0.88	High Similarity	NPC471270
0.8667	High Similarity	NPC236707
0.8571	High Similarity	NPC185605
0.8429	Intermediate Similarity	NPC96484
0.84	Intermediate Similarity	NPC83351
0.84	Intermediate Similarity	NPC167891
0.84	Intermediate Similarity	NPC11908
0.8378	Intermediate Similarity	NPC253190
0.8378	Intermediate Similarity	NPC265588
0.8356	Intermediate Similarity	NPC201048
0.8356	Intermediate Similarity	NPC306727
0.8356	Intermediate Similarity	NPC476366
0.8333	Intermediate Similarity	NPC23954
0.8333	Intermediate Similarity	NPC242992
0.8267	Intermediate Similarity	NPC470758
0.8267	Intermediate Similarity	NPC91594
0.8267	Intermediate Similarity	NPC470711
0.8267	Intermediate Similarity	NPC85105
0.8267	Intermediate Similarity	NPC149550
0.8261	Intermediate Similarity	NPC287339
0.8243	Intermediate Similarity	NPC66566
0.8243	Intermediate Similarity	NPC477923
0.8219	Intermediate Similarity	NPC265485
0.8219	Intermediate Similarity	NPC220939
0.8194	Intermediate Similarity	NPC92801
0.8194	Intermediate Similarity	NPC34834
0.8182	Intermediate Similarity	NPC96362
0.8182	Intermediate Similarity	NPC287749
0.8169	Intermediate Similarity	NPC244790
0.8143	Intermediate Similarity	NPC267027
0.8143	Intermediate Similarity	NPC326310
0.8133	Intermediate Similarity	NPC470749
0.8125	Intermediate Similarity	NPC471267
0.8116	Intermediate Similarity	NPC225415
0.8108	Intermediate Similarity	NPC477138
0.8108	Intermediate Similarity	NPC91858
0.8108	Intermediate Similarity	NPC243342
0.8101	Intermediate Similarity	NPC317458
0.8082	Intermediate Similarity	NPC167706
0.8082	Intermediate Similarity	NPC164022
0.8077	Intermediate Similarity	NPC249423
0.8077	Intermediate Similarity	NPC476646
0.8056	Intermediate Similarity	NPC9942
0.8056	Intermediate Similarity	NPC473893
0.8056	Intermediate Similarity	NPC474248
0.8056	Intermediate Similarity	NPC471560
0.8049	Intermediate Similarity	NPC133588
0.8028	Intermediate Similarity	NPC68703
0.8028	Intermediate Similarity	NPC69649
0.8026	Intermediate Similarity	NPC477924
0.8025	Intermediate Similarity	NPC175145
0.8025	Intermediate Similarity	NPC475069
0.8	Intermediate Similarity	NPC291503
0.8	Intermediate Similarity	NPC32832
0.7975	Intermediate Similarity	NPC471408
0.7975	Intermediate Similarity	NPC218616
0.7975	Intermediate Similarity	NPC87489
0.7975	Intermediate Similarity	NPC296701
0.7973	Intermediate Similarity	NPC68443
0.7973	Intermediate Similarity	NPC182717
0.7949	Intermediate Similarity	NPC281880
0.7949	Intermediate Similarity	NPC236112
0.7949	Intermediate Similarity	NPC295131
0.7927	Intermediate Similarity	NPC470620
0.7927	Intermediate Similarity	NPC476948
0.7922	Intermediate Similarity	NPC476314
0.7895	Intermediate Similarity	NPC274079
0.7895	Intermediate Similarity	NPC477925
0.7887	Intermediate Similarity	NPC202017
0.7875	Intermediate Similarity	NPC82623
0.7875	Intermediate Similarity	NPC79945
0.7857	Intermediate Similarity	NPC96793
0.7857	Intermediate Similarity	NPC68656
0.7857	Intermediate Similarity	NPC323424
0.7857	Intermediate Similarity	NPC144650
0.7848	Intermediate Similarity	NPC159148
0.7848	Intermediate Similarity	NPC474531
0.7838	Intermediate Similarity	NPC110799
0.7838	Intermediate Similarity	NPC242001
0.7821	Intermediate Similarity	NPC30986
0.7821	Intermediate Similarity	NPC209430
0.7792	Intermediate Similarity	NPC471798
0.7792	Intermediate Similarity	NPC130136
0.7778	Intermediate Similarity	NPC114651
0.7778	Intermediate Similarity	NPC476650
0.7778	Intermediate Similarity	NPC185568
0.7778	Intermediate Similarity	NPC15534
0.7778	Intermediate Similarity	NPC231310
0.7778	Intermediate Similarity	NPC171225
0.7765	Intermediate Similarity	NPC275671
0.7763	Intermediate Similarity	NPC313179
0.7763	Intermediate Similarity	NPC171148
0.7763	Intermediate Similarity	NPC313185
0.7763	Intermediate Similarity	NPC69383
0.7763	Intermediate Similarity	NPC133580
0.775	Intermediate Similarity	NPC47763
0.775	Intermediate Similarity	NPC202389
0.775	Intermediate Similarity	NPC155521
0.775	Intermediate Similarity	NPC49964
0.775	Intermediate Similarity	NPC259858
0.7746	Intermediate Similarity	NPC258595
0.7738	Intermediate Similarity	NPC187785
0.7738	Intermediate Similarity	NPC259875
0.7738	Intermediate Similarity	NPC115607
0.7733	Intermediate Similarity	NPC95165
0.7733	Intermediate Similarity	NPC471799
0.7722	Intermediate Similarity	NPC474592
0.7722	Intermediate Similarity	NPC234193
0.7722	Intermediate Similarity	NPC104120
0.7722	Intermediate Similarity	NPC148685
0.7722	Intermediate Similarity	NPC206062
0.7722	Intermediate Similarity	NPC157895
0.7722	Intermediate Similarity	NPC13554
0.7714	Intermediate Similarity	NPC83200
0.7714	Intermediate Similarity	NPC81615
0.7703	Intermediate Similarity	NPC189745
0.7703	Intermediate Similarity	NPC145498
0.7683	Intermediate Similarity	NPC470360
0.7683	Intermediate Similarity	NPC109528
0.7681	Intermediate Similarity	NPC240506
0.7671	Intermediate Similarity	NPC276616
0.7671	Intermediate Similarity	NPC245795
0.7671	Intermediate Similarity	NPC208999
0.7662	Intermediate Similarity	NPC1973
0.7662	Intermediate Similarity	NPC106432
0.7662	Intermediate Similarity	NPC167873
0.7654	Intermediate Similarity	NPC159168
0.7654	Intermediate Similarity	NPC169941
0.7654	Intermediate Similarity	NPC253402
0.7654	Intermediate Similarity	NPC134481
0.7654	Intermediate Similarity	NPC470558
0.7654	Intermediate Similarity	NPC471987
0.7654	Intermediate Similarity	NPC474634
0.7654	Intermediate Similarity	NPC207013
0.7654	Intermediate Similarity	NPC251475
0.7647	Intermediate Similarity	NPC3345
0.7647	Intermediate Similarity	NPC11216
0.7647	Intermediate Similarity	NPC329596
0.7647	Intermediate Similarity	NPC80561
0.7647	Intermediate Similarity	NPC204188
0.7647	Intermediate Similarity	NPC291484
0.7639	Intermediate Similarity	NPC476406
0.7639	Intermediate Similarity	NPC475897
0.7639	Intermediate Similarity	NPC250977
0.7632	Intermediate Similarity	NPC469593
0.7632	Intermediate Similarity	NPC309178
0.7632	Intermediate Similarity	NPC469534
0.7632	Intermediate Similarity	NPC471797
0.7632	Intermediate Similarity	NPC469533
0.7632	Intermediate Similarity	NPC100334
0.7625	Intermediate Similarity	NPC264245
0.7619	Intermediate Similarity	NPC474668
0.7619	Intermediate Similarity	NPC280556
0.7619	Intermediate Similarity	NPC67872
0.7606	Intermediate Similarity	NPC290367
0.7606	Intermediate Similarity	NPC101128
0.7606	Intermediate Similarity	NPC300593
0.7606	Intermediate Similarity	NPC107540
0.7595	Intermediate Similarity	NPC308038
0.7595	Intermediate Similarity	NPC233295
0.7595	Intermediate Similarity	NPC109546
0.7595	Intermediate Similarity	NPC84694
0.7595	Intermediate Similarity	NPC143182
0.7595	Intermediate Similarity	NPC28862
0.7595	Intermediate Similarity	NPC81306
0.7595	Intermediate Similarity	NPC47982
0.759	Intermediate Similarity	NPC255143
0.759	Intermediate Similarity	NPC261266
0.759	Intermediate Similarity	NPC299068
0.759	Intermediate Similarity	NPC139724
0.7568	Intermediate Similarity	NPC210323
0.7564	Intermediate Similarity	NPC90979
0.7564	Intermediate Similarity	NPC214570
0.7564	Intermediate Similarity	NPC477426
0.7564	Intermediate Similarity	NPC203403
0.7564	Intermediate Similarity	NPC477425
0.7564	Intermediate Similarity	NPC74995
0.7564	Intermediate Similarity	NPC157996
0.7564	Intermediate Similarity	NPC474826
0.7564	Intermediate Similarity	NPC470428
0.7564	Intermediate Similarity	NPC472805
0.7564	Intermediate Similarity	NPC101475
0.7564	Intermediate Similarity	NPC40394
0.7564	Intermediate Similarity	NPC34177
0.7564	Intermediate Similarity	NPC477427
0.7561	Intermediate Similarity	NPC470077
0.7561	Intermediate Similarity	NPC205845
0.7561	Intermediate Similarity	NPC238485
0.7561	Intermediate Similarity	NPC83702
0.7561	Intermediate Similarity	NPC238992
0.7558	Intermediate Similarity	NPC41554
0.7558	Intermediate Similarity	NPC97404
0.7534	Intermediate Similarity	NPC269077
0.7534	Intermediate Similarity	NPC185874

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 NPC471268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1926
0.2-0.3	4009
0.3-0.4	2141
0.4-0.5	600
0.5-0.6	257
0.6-0.7	65
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
0.7763	Intermediate Similarity	NPD8264	Approved
0.7375	Intermediate Similarity	NPD7645	Phase 2
0.7324	Intermediate Similarity	NPD368	Approved
0.7284	Intermediate Similarity	NPD7525	Registered
0.7215	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6933	Approved
0.7089	Intermediate Similarity	NPD6942	Approved
0.7089	Intermediate Similarity	NPD7339	Approved
0.7037	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6926	Approved
0.6962	Remote Similarity	NPD6924	Approved
0.6957	Remote Similarity	NPD342	Phase 1
0.6951	Remote Similarity	NPD6929	Approved
0.6923	Remote Similarity	NPD7151	Approved
0.6923	Remote Similarity	NPD7150	Approved
0.6923	Remote Similarity	NPD7152	Approved
0.6897	Remote Similarity	NPD7524	Approved
0.6897	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4225	Approved
0.6867	Remote Similarity	NPD6931	Approved
0.6867	Remote Similarity	NPD7332	Phase 2
0.6867	Remote Similarity	NPD6930	Phase 2
0.6867	Remote Similarity	NPD7514	Phase 3
0.6829	Remote Similarity	NPD7145	Approved
0.6795	Remote Similarity	NPD7143	Approved
0.6795	Remote Similarity	NPD7144	Approved
0.6786	Remote Similarity	NPD6902	Approved
0.6782	Remote Similarity	NPD3618	Phase 1
0.6707	Remote Similarity	NPD5776	Phase 2
0.6707	Remote Similarity	NPD6925	Approved
0.6706	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6628	Remote Similarity	NPD6695	Phase 3
0.662	Remote Similarity	NPD4219	Approved
0.6593	Remote Similarity	NPD6079	Approved
0.6562	Remote Similarity	NPD5344	Discontinued
0.6556	Remote Similarity	NPD5328	Approved
0.6552	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4786	Approved
0.6506	Remote Similarity	NPD6932	Approved
0.6477	Remote Similarity	NPD6893	Approved
0.6471	Remote Similarity	NPD4748	Discontinued
0.6458	Remote Similarity	NPD7639	Approved
0.6458	Remote Similarity	NPD7640	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4732	Discontinued
0.6413	Remote Similarity	NPD7515	Phase 2
0.6395	Remote Similarity	NPD6898	Phase 1
0.6364	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6354	Remote Similarity	NPD7638	Approved
0.6344	Remote Similarity	NPD4202	Approved
0.6341	Remote Similarity	NPD4784	Approved
0.6341	Remote Similarity	NPD4785	Approved
0.6333	Remote Similarity	NPD7750	Discontinued
0.6327	Remote Similarity	NPD5211	Phase 2
0.6316	Remote Similarity	NPD5222	Approved
0.6316	Remote Similarity	NPD5221	Approved
0.6316	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4243	Approved
0.6292	Remote Similarity	NPD1696	Phase 3
0.6269	Remote Similarity	NPD385	Approved
0.6269	Remote Similarity	NPD384	Approved
0.625	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4159	Approved
0.6222	Remote Similarity	NPD4519	Discontinued
0.6222	Remote Similarity	NPD4623	Approved
0.6222	Remote Similarity	NPD5279	Phase 3
0.62	Remote Similarity	NPD5141	Approved
0.6186	Remote Similarity	NPD5290	Discontinued
0.6163	Remote Similarity	NPD4195	Approved
0.6163	Remote Similarity	NPD6683	Phase 2
0.6146	Remote Similarity	NPD4697	Phase 3
0.6122	Remote Similarity	NPD4696	Approved
0.6122	Remote Similarity	NPD6648	Approved
0.6122	Remote Similarity	NPD5286	Approved
0.6122	Remote Similarity	NPD5285	Approved
0.6111	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7748	Approved
0.6092	Remote Similarity	NPD4820	Approved
0.6092	Remote Similarity	NPD4822	Approved
0.6092	Remote Similarity	NPD4819	Approved
0.6092	Remote Similarity	NPD4821	Approved
0.6082	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD5275	Approved
0.6071	Remote Similarity	NPD4190	Phase 3
0.6064	Remote Similarity	NPD7087	Discontinued
0.6064	Remote Similarity	NPD7637	Suspended
0.6061	Remote Similarity	NPD5223	Approved
0.6047	Remote Similarity	NPD4271	Approved
0.6047	Remote Similarity	NPD4268	Approved
0.6026	Remote Similarity	NPD371	Approved
0.6019	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD5224	Approved
0.596	Remote Similarity	NPD4700	Approved
0.5957	Remote Similarity	NPD7136	Phase 2
0.5957	Remote Similarity	NPD3168	Discontinued
0.5955	Remote Similarity	NPD4269	Approved
0.5955	Remote Similarity	NPD4270	Approved
0.5941	Remote Similarity	NPD5175	Approved
0.5941	Remote Similarity	NPD5174	Approved
0.5934	Remote Similarity	NPD1694	Approved
0.5918	Remote Similarity	NPD7902	Approved
0.5909	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4695	Discontinued
0.5909	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4634	Approved
0.5895	Remote Similarity	NPD6411	Approved
0.5889	Remote Similarity	NPD5332	Approved
0.5889	Remote Similarity	NPD5362	Discontinued
0.5889	Remote Similarity	NPD5331	Approved
0.5857	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4753	Phase 2
0.5843	Remote Similarity	NPD4790	Discontinued
0.5842	Remote Similarity	NPD7632	Discontinued
0.5833	Remote Similarity	NPD6399	Phase 3
0.5816	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5785	Approved
0.5784	Remote Similarity	NPD4754	Approved
0.5778	Remote Similarity	NPD4221	Approved
0.5778	Remote Similarity	NPD4223	Phase 3
0.5778	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4194	Approved
0.5769	Remote Similarity	NPD4193	Approved
0.5769	Remote Similarity	NPD5697	Approved
0.5769	Remote Similarity	NPD4191	Approved
0.5769	Remote Similarity	NPD4192	Approved
0.5766	Remote Similarity	NPD7516	Approved
0.5761	Remote Similarity	NPD5363	Approved
0.5741	Remote Similarity	NPD4632	Approved
0.573	Remote Similarity	NPD4252	Approved
0.5714	Remote Similarity	NPD6110	Phase 1
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD5168	Approved
0.5714	Remote Similarity	NPD6686	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4730	Approved
0.5714	Remote Similarity	NPD6881	Approved
0.5699	Remote Similarity	NPD5786	Approved
0.5699	Remote Similarity	NPD5690	Phase 2
0.5699	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD6051	Approved
0.5684	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD6101	Approved
0.5676	Remote Similarity	NPD7328	Approved
0.5676	Remote Similarity	NPD7327	Approved
0.5673	Remote Similarity	NPD7128	Approved
0.5673	Remote Similarity	NPD6402	Approved
0.5673	Remote Similarity	NPD6675	Approved
0.5673	Remote Similarity	NPD4767	Approved
0.5673	Remote Similarity	NPD6640	Phase 3
0.5673	Remote Similarity	NPD5739	Approved
0.5673	Remote Similarity	NPD4768	Approved
0.5663	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD6013	Approved
0.566	Remote Similarity	NPD6012	Approved
0.5652	Remote Similarity	NPD4265	Approved
0.5652	Remote Similarity	NPD4197	Approved
0.5652	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD8297	Approved
0.5641	Remote Similarity	NPD1145	Discontinued
0.5641	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD3573	Approved
0.5625	Remote Similarity	NPD3197	Phase 1
0.5625	Remote Similarity	NPD7838	Discovery
0.5619	Remote Similarity	NPD5701	Approved
0.5612	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7900	Approved
0.5607	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7102	Approved
0.5607	Remote Similarity	NPD6883	Approved
0.5607	Remote Similarity	NPD5251	Approved
0.5607	Remote Similarity	NPD5247	Approved
0.5607	Remote Similarity	NPD5135	Approved
0.5607	Remote Similarity	NPD5249	Phase 3
0.5607	Remote Similarity	NPD5169	Approved
0.5607	Remote Similarity	NPD5250	Approved
0.5607	Remote Similarity	NPD7290	Approved
0.5607	Remote Similarity	NPD5248	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